The Salary Story

Look at the rate the salary changes:

• Years 1-2: Trickle up. You're still learning, the firm is testing fit.
• Years 3-5: Acceleration. Firms have invested in you, and you can walk away with portable skills. So they pay up to keep that investment.
• Years 6-8: Plateau. You're entrenched. Moving firms means rebuilding relationships, proving partnership potential from scratch, and competing against internal candidates. Firms know this, and compensation slows because of reduced leverage.

Peak Leverage

Charting salary reveals a hidden message: your strongest position to improve fit, negotiate a bonus, or redirect your career is between years 3-5.

The problem is that many associates wait too long to evaluate their options. By the time they realize they're not on the right track, inertia has set in. If you're considering a move, understanding why working with multiple recruiters backfires can help you navigate the process more effectively.

You Have Control

The chart tells a story you don't hear much as a biglaw associate: you have control.

Your window of maximum leverage is finite. Years 3-5 represent the sweet spot where your skills are portable, your options are open, and firms are willing to pay to keep you. Don't let that window close without at least evaluating what's out there.

The associates who thrive are the ones who take an active role in shaping their careers during this critical period.

If you're a mid-level associate wondering about your options, now is the time to start the conversation.

In this conversation, we dig into the skill set of "seeing around the corner" in an era where enforcement priorities are being telegraphed faster than ever: reading executive orders as leading indicators of DOJ policy, watching AAG social media accounts for enforcement signals, and synthesizing those data points into predictive counseling that actually gives general counsel something new to bring to their C-suite. We also get into the 360° view that comes from having been both a civil rights defense lawyer and a national security prosecutor, why the hustle of an immigrant cab driver's kid doesn't turn off when you land at a top-tier firm, and why the first thing he added to his weekly calendar was "Thursday: reach out to someone in the network."

Keep reading below for the full episode and the complete transcript of our conversation.

Top Insights

Below are the highlights of our conversation:

• Seeing Around the Corner: This administration is unusually transparent about where it's heading. Alamdar's predictive framework: read the executive orders (day-one EOs tend to become DOJ policy in days, not months), watch what the AAGs post on X and LinkedIn, follow what SDNY and EDNY are charging, and look at the policy releases. The alpha is synthesizing those data points fast enough to give a client time to move before the subpoena hits.
• The 360° View From Both Sides: Alamdar represented Muslim, South Asian, and Arab clients post-9/11 as a civil rights defense lawyer, then spent 17 years prosecuting national security cases at DOJ. That combination means when he counsels a client now, he can simultaneously map the holes in the prosecutor's case, the prosecutor's likely strategic framing, and how a jury will see it. Clients who only hire ex-prosecutors or only hire ex-defense lawyers are missing half the picture.
• Reporting Up + Predicting = Business Development: As U.S. Attorney, his job was to report up to the DAG and AG and predict what would happen next. As a partner, his job is to do the same for in-house counsel, so they can do the same for the C-suite. Same skill, same discipline. Young associates who learn to "report up and predict" early are practicing the exact muscle senior partners use to counsel clients.
• Self-Disclosure Is a Ticking Clock: With cartels now designated as foreign terrorist organizations, companies with even tangential third-party connections (a security vendor in Mexico affiliated with a cartel) can face material-support-of-terrorism exposure. Once a subpoena hits, the self-disclosure credit window has largely closed. The counsel's job is to pressure-test disclosure before that happens.
• Humility Is the Operating System: Son of a London cab driver, sold newspapers door-to-door at 13 in a British accent nobody could parse. The rejections never stopped being instructive. Returning phone calls from every cold outreach now isn't just courtesy, it's the same discipline that made him the U.S. Attorney, and it's the one thing he believes any leader has to practice daily.

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Full Transcript

Khurram Naik: Alamdar, I am very glad to have you back on the podcast.

Alamdar Hamdani: Yeah, it's good to be back. It's good to be talking to you again, in a different role. It seems like yesterday when I was sitting in the U.S. Attorney's chair and was privileged to get to know you and talk about my journey. It's nice to be back, and to see where I'm at, to see where I've come. What I'm going to do, Khurram, if you do me the favor of checking in on me every couple of years, is I will go back and listen to these podcasts as my own personal diary.

Khurram Naik: We're going to add to the diary of Alamdar Hamdani, as well as you, Khurram, because the last time we spoke I think you had one kid, and now you have two. The last time we spoke, it was just you on your own, and now you have a business partner, who, from what I understand, is probably the real reason of your success. For those who don't know, Khurram is in business with his wife, which, frankly, I think is awesome, and many of us could be so lucky.

Khurram Naik: Well, we're risking making this episode about me. There's a metaphor of thinking of a business like a baby. A one-year-old business is like having a one-year-old, a two-year-old business like a two-year-old. You're still in your infant days again. Every time I've looked back on diaries of key experiences, I am surprised by things that were prescient. I'm reminded of things I couldn't even remember I was thinking about. This is going to be a really interesting counterpoint to your previous episode, because you were so in your senior days of that chapter. Now you're in junior days of the next chapter. What an interesting transition.

Alamdar Hamdani: Yes, I agree. In a couple of years.

Khurram Naik: Let's start talking about what that transition is like. Any number of people look at a U.S. Attorney returning from government and think, that lawyer's got it made, unbelievable experience and relationships, knows the DOJ inside out, they're going to crush it in private practice, it's playing on easy mode. Tell me what that attitude gets wrong.

Alamdar Hamdani: Look, there are some truths to it. When I was at the Department of Justice, I worked in three different offices. I worked in the Eastern District of Kentucky, a small office in a smaller district. Then I moved to Main Justice, where I spent five years chasing Al-Qaeda, Iran, and ISIS in the National Security Division as a trial lawyer, working with some of the best federal prosecutors in the country, SDNY, EDNY, SDTX. Then I became an AUSA in the Southern District of Texas, where I looked at national security and public corruption. I got to try some very important cases, look at some large investigations. And then I got to be the United States Attorney and build a new skill set as a leader within the DOJ, even got to be a part of the Attorney General's Advisory Committee, which was 11 U.S. Attorneys chosen by the AG to meet every six weeks and be part of the policymaking structure of the DOJ.

Alamdar Hamdani: Describing me as somebody who's had this incredible experience and knows the DOJ inside out is not an exaggeration. All of us former U.S. Attorneys who've had a long career at DOJ can describe what the halls of DOJ look and smell like, what AUSAs fret over, what FBI agents and ICE agents and HSI agents and ATF care about. That doesn't exactly mean I'm going to make a million dollars a day. It doesn't mean I'm going to get all the business on day one. I knew that when I left the Department. When firms hire people like me as partners coming in, they understand that as well. They're taking a bet. Bracewell takes a bet on me, and for all the other former U.S. Attorneys in private practice. The firms invest in us and say, we believe you can take that skill set, that experience, and translate it into business. The best firms are the ones that will say, we know it's going to take you a little time to get it. That patience, the patience that's being shown by Bracewell toward me, is comforting, but only so far, because guys and women like me are driven. As you know, Khurram, I'm the son of a cab driver. I'm a migrant. The only way you get to be the U.S. Attorney from that background is that you are driven and you are a hustler. You don't take what's been given to you for granted. My mother used to say this: if you laugh too much, you're going to cry. What an awful thing to say. If you're so happy, something you're going to be sad. But there's a little bit of migrant attitude: don't count on right now, because tomorrow may bring something bad, so let's prepare for that. I'm constantly thinking, it's great I'm being given this runway and this time, but I've got to make sure I get this. I've got to make sure that I'm able to be a productive member of the firm today.

Khurram Naik: Can you paint a picture of what it's like to leave the office? You have one of the most powerful, high-stakes roles in law, and then a week or two after that, you're no longer in the role. What was the first concrete moment you really felt, okay, I am no longer U.S. Attorney for the Southern District of Texas?

Alamdar Hamdani: The good thing is, and it's because I have a family that keeps me grounded, a wife who I don't think has ever been impressed by anything I've ever accomplished career-wise, and is more impressed when I remember to clean the house or mow the lawn. What that means is my identity, for the most part, wasn't wrapped into being the U.S. Attorney. Did I take pride in being the U.S. Attorney? Absolutely. Did my mother take pride? Of course. She took my LinkedIn profile picture when I was U.S. Attorney, blew it up, and put it on the wall. Classic Indian mother.

Alamdar Hamdani: When November 6th happened, that's when Trump became president-elect, I was prepared to leave. As a political appointee, I served at the pleasure of the president. History has told me, especially with Trump, that he will get rid of U.S. Attorneys from prior administrations fairly rapidly. And he's right to. I was already preparing. On November 6th I told my office, I'm going to transition out, I'm going to leave prior to the new administration. I made a promise to my office that I will be your U.S. Attorney, and I will believe I'm going to be your U.S. Attorney, until election day. That meant I'm not going to look for a job, I'm not going to have one foot out the door until the election tells me I should. On November 6th I was prepared to transition out. I spent the next few months looking for a place to land, and I was blessed to have many opportunities. As a recruiter you know, it is often difficult for somebody coming out of government to find a landing spot. It helped that I was the former U.S. Attorney. So when did I really believe I would no longer be the U.S. Attorney? January 20th. I was okay with it because I'd come to terms with it. On January 20th I also realized I'm now going to have to be in a different mode. Build a book of business from scratch.

Khurram Naik: There are a few components I'm interested in. One is the substantive practice, what changes from U.S. Attorney to private practice. Another is business development, because there's no business development as a U.S. Attorney. You've been in private practice before, but now in returning, I'm curious what's been the difference in how you think through legal issues as a prosecutor versus private practice, and what has surprised you?

Alamdar Hamdani: I was in private practice before, and I had my own law firm for a few years before. I took on some national security cases as a criminal defense lawyer. I took on a bunch of pro bono civil rights cases post-9/11. That's important, because I had already learned how to have a client who is a defendant, how to talk to that client, how to understand and appreciate what they were going through. That was important, and it became a very important part of my time as a federal prosecutor, because of that experience. I was in a room as a very young lawyer right after 9/11, representing Muslims, South Asians, and Arabs. A person sitting next to me is a person from Pakistan who is scared. On the other side are two federal agents. That experience, that empathy, that curiosity, drove me as a prosecutor. When we were building national security cases where many of the folks on the other side were like the people I used to represent, it gave me a critical view of how things were being built. I could talk to an agent and explain, this is how it's going to happen, this is what it's going to look like on the other side.

Alamdar Hamdani: The wonderful thing about being a prosecutor and a defense lawyer, and now being a defense lawyer again, is I have been given the gift of analyzing issues on both sides. If somebody's been accused of wire fraud, I'll talk to the client, understand what happened, understand where the facts are. I can quickly look at the elements of the crime and understand where the holes are. But I may also counsel the client and say, these may be holes, but here's what I think the prosecutor is going to focus on, here's what the prosecutor thinks is the strength of his or her case, and here's what I think they think is the weakness. When we go to a jury, this is what it's going to look like. I can take all of that and say, this is in my opinion the best way to approach the prosecutor, do you really want to try this case because of this issue, or is it our time to plead the case. Because I have an understanding of both sides, I also have an understanding of how the client feels but also how the prosecutor feels. When I use AI to walk me through issues, the prompts I give are the prompts of somebody who's been both a criminal defense lawyer and a prosecutor. I get to look at it from a 360-degree view.

Alamdar's 360° view, seeing the case from the prosecutor's chair and the defense chair at the same time, is the same diversification argument Louis Tompros made in his episode about doing both plaintiff and defense work, both trial and appellate, patent and copyright. Adjacent experience sharpens the core. Listen to my conversation with Louis Tompros.

Khurram Naik: Is there something different about how you approach the substantive aspects of analyzing a case now that you did previously?

Alamdar Hamdani: Yes, because I didn't have the view of a prosecutor. Prior to joining the Department, I didn't know what a prosecutor goes through and thinks about. I'll give you a story. When I interviewed for the U.S. Attorney job, one of the senators asked me, Alamdar Hamdani, ACLU board, civil rights lawyer, prior to joining the government, and then Alamdar Hamdani, national security prosecutor, how have you changed? I said, the big difference between the Alamdar Hamdani sitting in front of you now, a national security prosecutor, as opposed to the Alamdar Hamdani who was just doing civil rights work, is this Alamdar Hamdani has a security clearance. I now know what's behind the curtain. I now know what the national security picture looks like. Before joining the government, I used to debate the U.S. Attorney's Office, I used to debate the DOJ, but I had debated out of a lack of understanding of what, for example, made a national security case. Now I approach a crime with the understanding of both a prosecutor and defense lawyer.

Khurram Naik: Let's add the dimension of business development. That's the biggest difference between private practice and government practice.

Alamdar Hamdani: Some things did not change. You had mentioned business development isn't in government practice. I will take issue with that. When you're a prosecutor, especially doing national security work, everything you do is above the fold, going after ISIS, Chinese and Iranian spies, Russian hackers. The cases don't fall into your lap. You have to hustle to get them. I had to work with agents and build not only a good body of work, but it meant hustling to get some of those cases, making sure agents understand that if we do good work in the Southern District of Texas, you don't have to go down to the Southern District of New York and have those guys prosecute it. Or if SDNY and EDNY are wanting to take my case, I'm going to fight my heart out to keep it in the Southern District of Texas. Often when I had a national security case, it would get briefed up quickly to leadership and FBI, so part of it is working with those agents and with Main Justice and FBI leadership and marketing to them. I will argue that kind of hustle, that kind of business development, is part of what you do as an AUSA.

Alamdar Hamdani: As the U.S. Attorney, I did a lot of social media interaction with the community, not only the legal community but the community in general. I wanted to demystify what we did in the office, but I also wanted to make sure the community knew to come to the U.S. Attorney's Office. I also wanted other parts of the DOJ to know that what we did in the office was important. I take all of that now into my business development role in private practice. I'm using social media. I'm using those contacts and that network to build my practice. A great example is a network of former FBI special agents in charge, former AUSAs, former DOJ folks, a network of former United States Attorneys I got to know over the past couple of years, that I built strong relationships with and kept in contact with, to help build my practice. Business development isn't just something that happened on January 20th, it's something that's been learned over 27 years of practice.

Alamdar's framing of business development as a long-run relationship play, networks built over decades that pay off years later, is exactly what Mani Walia described in his episode about the 2012 lunch with a struggling colleague that became one of the biggest litigation-funding deals of 2023. Intangibles become tangibles, with a decade's patience. Listen to my conversation with Mani Walia.

Khurram Naik: Steve Martin used to say, you'll use everything you ever knew. Something interesting you said is about the development of cases. Earning agents' attention so they come to you proactively, that's like being in-house, an open line of communication. Are there any analogues in private practice? My guess is when you're developing a case as a prosecutor, there's a tradeoff, you could lose the opportunity to prosecute. By way of analogy, in private practice, maybe we do something to service a client, even if we think we're on the verge of developing something deeper.

Alamdar Hamdani: There is. It's the constant calculus being analyzed by in-house counsel as it relates to the Department of Justice, specifically voluntary self-disclosure. Do you disclose to the government if you find wrongdoing within the organization? That calculus is one that in-house counsel, hopefully with good outside counsel who understand DOJ, can make. For example, this administration is focused on prosecution of cartels. Cartels have now been designated as foreign terrorist organizations. What that means is, to build a case against a cartel in the old days required having some sort of drug nexus. That doesn't need to happen anymore. Companies in Mexico hire security companies to provide security. That security company is owned by or affiliated with the cartels. Now the company that's hired the security firm can be accused of providing material support to terrorism, which can lead to 10x, 100x fines, or the amount of revenues it has in a particular year. If I'm a company and I discover that I've got a third-party contractor that may have a connection with a cartel, I'm going to ask, do I self-disclose? The DOJ may give me credit if I self-disclose. The DOJ will certainly ask me questions and now may probe into my company. What else will they find? Will I get a declination? Will it lead to some admission of guilt? Companies right now are really trying to decide whether it's ready. The great thing about being in this role as counselor: AI can replace some of the root legal work, but AI can't replace the human relationships and connections former DOJ people have created. AI can't take away the judgment of somebody like us when counseling clients on issues with hundreds of millions of dollars of ramifications. AI can't take away the ability to say, now is not the time. Let's do some more investigation. Once a subpoena hits, it may be too late to come forward and self-disclose. There's that ticking clock.

Khurram Naik: You probably had ideas in the office about the ways your skills would be useful in private practice. Now that you're a little more than a year out, maybe you have some changed opinions from experience. What has been unexpected that has turned out to be really helpful to clients?

Alamdar Hamdani: Let me talk about how I counsel, going back to what I observed growing up. My father was a cab driver. Sometimes as a kid he'd let me sit in the well of the cab and I would watch him. He had a black cab in England, which was a badge of honor, because to get a black cab, you had to drive all the routes, know all the streets, pass these tests. He was really proud of his black cab. We didn't have a car, just the black cab that stood outside our semi-detached house. I'd hide in the well of the passenger compartment and watch my father. He would pick up a passenger, take them from point A to point B, but more importantly, my father would learn why somebody went from A to B, because my father was a chatty cabbie. He talked in this wonderful Indian accent laced with British, and he really tried to accentuate the British part of his accent. He'd really make them feel comfortable, and they would tell my father, a stranger, a skinny brown stranger, about why they went from point A to point B, what was going on in their world. That was a skill born from empathy, from curiosity, grounded in service to that person, and with patience, because he listened. And then he'd try to tell some joke in a British Indian accent and make them laugh. To this day I tell the best dad jokes.

Alamdar Hamdani: With clients I am empathetic. I really want to know what happened. Just because the prosecutor has accused a client of something, or just because it looks like the client may have committed wire fraud, I'm going to listen. I'm curious. I've got to keep an open mind. At the end of the day, I'm going to give you advice based upon my service to you, and I'm going to be patient in how I give that advice. It's going to take me time. I'm not just going to give you an answer in the meeting. I'm going to want to listen first. Our calls are going to be long initially, because I want to know what's going on. Clients have responded well. It's created a very good attorney-client relationship, one built from trust, one built from understanding, both ways. It works for me. Others may be more strident, get to the chase. I'm not that guy.

Khurram Naik: In building a practice, there's this assumption about white collar and government enforcement, but maybe you can talk about the mix of work you've put yourself in. You could do civil litigation, criminal, white collar. What are the pros and cons of a practice driven by one of these, and how are you thinking about the mixture?

Alamdar Hamdani: Because I did commercial litigation before I joined the Department, I'm comfortable doing both civil and criminal litigation. Because I ran one of the largest civil divisions of a U.S. Attorney's Office, I'm also comfortable doing civil work as it relates to DOJ enforcement, as opposed to only white collar criminal. I'm trying to develop all parts of my practice. What makes my approach unique is my network consists of former DOJ attorneys, former U.S. Attorneys, and folks I knew when I was doing civil work before joining the Department. The network I created to become U.S. Attorney, a big, brown, South Asian network, is also important. One thing about me: when I reach out to a former U.S. Attorney or a South Asian attorney, I often get back a phone call, which is not always the case in this world. I miss that when I was the U.S. Attorney, folks would always return my phone calls. That's not always the case now. You've got to get over it. It is often a hit to your ego. I will always return somebody else's call. Even if someone cold-calls me, I will listen and be respectful, because that happened to me as an AUSA. Certain AUSAs in other offices would treat me like crap. I never forgot. When I was U.S. Attorney, I always told my AUSAs to treat DOJ lawyers with the utmost respect. If somebody calls me and asks to meet, I'm not going to ignore their phone calls, I'm not going to be a jerk.

Khurram Naik: Can you talk about the pros and cons of niching hard right now versus building broadly?

Alamdar Hamdani: Niching is good. For me right now it's government enforcement and investigations, that's my real sweet spot, both civil and criminal. The benefit is you can market the area you'll be good at. At the same time, I'm building a practice from scratch, so I've got to use my skill set from my prior life as a commercial litigator. I've brought in commercial litigation matters that draw upon that experience. For example, a commercial litigation matter that required advocacy in front of a public entity, or one where Fifth Amendment issues were at stake for a client. I can marry both worlds. My sweet spot is 17 years as a trial lawyer. One thing I bring that other commercial litigators may not always have is having tried cases, having tried a bunch. I've given speeches in front of massive crowds as U.S. Attorney. I've given press conferences as U.S. Attorney. Those skills are transferable. I feel comfortable understanding both the press issues as well as the legal issues for a client, because I was in there. I understand what makes a U.S. Attorney tick, including what he or she thinks about when thinking press strategy for their office.

Alamdar Hamdani: Every day I look at the X accounts of people like Harmeet Dhillon, the AAG for civil rights. She puts out content which makes me constantly think, how is this going to affect my client? She'll put out content that relates to issues I don't know about, that I'm going to learn real quick so I can advise clients in that space. Looking at the social media accounts of DOJ officials, or those this administration cares about, is something I'm trying to develop as a new skill.

Khurram Naik: I want to pick up on predictive counseling. You're starting to mine different types of data, different types of insights that other people wouldn't have a clue would be relevant. Can you talk about predictive counseling?

Alamdar Hamdani: Helping a client see around the corner is really a big part of what I do as a government investigations partner. That is to help a client look around the corner by leveraging all of my skills. Taking the different data points out there: the one thing about this administration, whether you agree with it or not, is it is incredibly transparent about what it's going to do. You can take an executive order the president has signed and pretty much understand that within a short order, because of the way this administration is set up, the White House and the DOJ will be aligned, that executive order will probably become DOJ policy pretty fast. Unlike other administrations, where DOJ policy sometimes took months, if not years, to develop. That's your first data point.

Alamdar Hamdani: Second, look at what the DOJ is saying. They're very transparent. Look at social media. Leadership is quite active, whether it's Todd Blanche or Pam Bondi, whether it's AAGs for the Criminal Division, Civil Division, Civil Rights Division, all in varying degrees on different platforms, X being one, LinkedIn being another. Look at what they're highlighting. Look at what the U.S. Attorney's Office is highlighting. I did it when I was U.S. Attorney. I would talk about cases that were important to me. It's probably going to be important to the office, probably important to leadership at DOJ. Policies are coming out every day. Look at what's being charged out of SDNY and EDNY on fraud, understand that's going to be a priority. A great example: the Southern District of Texas along the border had the most prosecutions, a lot driven by immigration. As former U.S. Attorney, I understand what HSI and ICE care about. You're going to see an increase in enforcement by HSI and ICE. What does that mean for businesses that do business in the Southern District of Texas?

Khurram Naik: How exactly are you communicating to clients, building that relationship, sharing insights?

Alamdar Hamdani: First of all, getting smart on the issue, from my own experience, researching it, understanding it, and talking to experts within my firm. I don't have to be an expert on everything. Tapping into the expertise within Bracewell. Stress-testing before I approach a client. You don't want to approach a potential client with a half-baked idea. That could backfire. Then approaching the potential client with, look, this is what I'm seeing, I want you to know about it. Having that initial phone call. Not a massive write-up. This is what I'm seeing, let's talk about it. Then having that discussion. You've got to know the issue pretty well, because the in-house counsel at an oil and gas firm is going to know oil and gas issues better than you. But what the in-house counsel doesn't know for the most part is what's going on at DOJ, what you think about DOJ, what you think is about to be enforced. That's the additional insight you bring. Now you've given your client something new to think about, something to talk to the C-suite about, or to the compliance team. That's a value add.

Alamdar Hamdani: I do a lot of AI research. AI has become incredibly powerful. I don't have the time to do a bunch of Google searches. I have powerful AI tools within the firm that I am using constantly, to refine my idea and refine how I speak about it. I will take memos I've written, speeches I've given, things I've done, and put them as part of what the AI tool will look at. They will also look at what I've done within the firm, so I can be smart about what I talk about.

Khurram Naik: Part of what you're talking about is packaging things to help your counterparts look smart with the team they roll up to, the C-suite. You're arming them with tools to approach the C-suite. How well do the incentives of a U.S. Attorney map onto a CEO?

Alamdar Hamdani: I've never been a CEO, but I have led an organization of 400 employees and 200 federal prosecutors, answerable to the Deputy Attorney General and the Attorney General on a semi-regular basis. One thing you learn as an AUSA, but really have to use as U.S. Attorney, is the ability to report up and predict. I was constantly doing that. Reporting up a massive issue I think is happening in the Southern District of Texas, or reporting up a big case, and giving them, this is what I think is going to happen as a result. I take that same view as to the role of in-house counsel or general counsel. Their job is to protect the company just as it is the C-suite's. Their job is to protect the interests of shareholders. They do that by reporting up to the C-suite, just as they have people reporting up to them. They're reporting up and predicting what's going to happen. Same skills I'm using when counseling clients. I'm reporting up what's happening and predicting what's going to happen as a result. You don't have to be the U.S. Attorney or CEO or CLO to understand that skill. Young associates at a law firm are constantly reporting up to their partners, if they're doing it right. When they report up, they don't just report up, they report up and go, and this is what I think is going to happen. That's a skill learned when they're a young associate. It's what we're all doing at smaller levels on much more impactful levels.

Alamdar's predictive-counseling framework is a close cousin of what Tim Yoo described in his episode: elite performers use deliberate preparation and decision trees so they're not reactive under pressure. Alamdar's version is reading executive orders and AAG posts as leading indicators, so clients aren't reactive when the subpoena shows up. Listen to my conversation with Tim Yoo.

Khurram Naik: Is there a piece of work you're most proud of in the past six months?

Alamdar Hamdani: Trump had issued an executive order on day one relating to DEI, which was a sea change from how the Biden administration did it. I understood that things were changing in that realm, not only for companies using DEI in the workplace, but how this administration would take that issue and use it within its enforcement structure, i.e., how the DOJ would take that particular statement in an EO and use it to enforce the behavior of private companies or public institutions. I figured it would, and I reached out to a public institution and said, I think this is going to happen. And it did. Because of that, I was able to help that institution get ahead of the curve. DEI, according to this administration, maps onto the Supreme Court case SFFA v. Harvard. They've extrapolated that case to mean companies that receive federal funds cannot have certain policies that would discriminate against not only African Americans but all races. If you receive federal funds, you're a federal contractor, and now you are subject to this administration's interpretation of that Supreme Court case. That has led to an enforcement mechanism by this DOJ that wasn't there before. That wasn't part of the Biden administration or the Trump one administration when it came to enforcement. It's a whole new enforcement mechanism.

Khurram Naik: What is one persistent misperception the private bar has about how enforcement attention forms?

Alamdar Hamdani: Why does an AUSA walk into a grand jury room and seek an indictment? That is the ultimate form of enforcement. Oftentimes they will think it's because the AUSA is driven by what the president has said, the political atmosphere, the political ethos. I would say for the most part, that's not the case. An AUSA is driven by the facts and the law, by what an agent has put in front of them based on an investigation. AUSAs for the most part do a good job of ignoring the noise of Washington, D.C., and focus on whether the case follows the facts and whether the case is one that deserves federal attention as opposed to maybe going to the state. Often private bar attorneys or people in general believe a prosecution is brought because of the political proclivities of a particular AUSA. That's not the case. As U.S. Attorney, I didn't know what the political leanings were of the people I led, nor did I care. AUSAs are apolitical animals. Whether this administration changes that perception, I'll leave for others to predict.

Khurram Naik: You talked about phone calls you can't always get returned. That's a big change from U.S. Attorney. What does this chapter taught you about resilience, setback, rejection?

Alamdar Hamdani: Let me go back to my father and leadership, and things I learned by watching. I learned about empathy, curiosity, service, patience. I also learned from my father, a man who had to raise a family, work two jobs, couldn't get past living paycheck to paycheck, finally was able to buy a house. I'll never forget when he had to pay his mosque dues every month, he couldn't afford it. You learn humility, you have to have humility. At 13 years old I sold newspapers door-to-door, spoke with a British accent, spoke too fast, and got rejected a lot. I learned to be humble, I learned to eat that, I learned I wasn't going to make much money. In college I sold New York Telephone subscriptions and Sesame Street books over the telephone, telephone sales. That teaches you humility. Along the way, I've learned to be humble.

Alamdar Hamdani: When I led the Southern District of Texas, I was humbled by my mistakes, and I made a lot. I sat down a couple of AUSAs and I apologized to them for an action I took, not expecting them to accept my apology. When you apologize, if you truly apologize, it's not about them accepting your apology, it's about them understanding you apologized and saying the words. Part of building a book of business from scratch, and not getting a return phone call, is understanding you are not on top of everybody's mind. That's part of being humbled. I don't think any of us can be effective leaders if we don't have humility as part of our daily makeup.

Khurram Naik: Was there any sense in you of, I did hard things to get here, why should I have to work hard again, why should I have to be rejected again, I've already done the hard stuff?

Alamdar Hamdani: No. Never felt that. I've never believed that I'm entitled to a damn thing. The one thing that makes this the greatest nation in the history of mankind is because those who come to this country, or those who are raised and born here, all believe at some point in their lives they can accomplish anything. They've got to strive. The ethos of the United States is who we are. I knew when I left that I was going to get rejected by some folks. Do I believe being the former U.S. Attorney might open some doors? Yes. But I never expected any door would open because I was a former U.S. I knew I had to open that door myself. I still feel that. I'll probably always feel that way. That's the one thing I try to instill in my children: nothing is ever going to be given to you.

Khurram Naik: Talk to me about the structure you've used in this building phase. How is that helping you resolve anxieties and the open-ended nature of this phase?

Alamdar Hamdani: For the past 15 or 16 years, I'm somebody who religiously exercises. Before I was a marathoner, got injured, and became a person who swims with a masters group every morning, five o'clock in the morning. When I was in law school, I wasn't healthy. Folks in law school ask me for one piece of advice: take care of your body and be healthy in law school. I learned that later in life. That's a big part of my routine. The other part is, I am present for my family. One of the gifts of being in the Department was you could be, you didn't make a lot of money, but you could be, and I thought I was a much better father and husband because of the Department. Then I am constantly working my list of contacts, building my network. Every day I see what's being pumped out from the Department, from the president, from different issues, trying to predict. How does the war in Iran manifest into issues in Houston? Into issues in the oil and gas industry?

Alamdar Hamdani: One thing I'd like to be better at is having a daily routine on that score. I've just added into my routine: every Thursday, I'm going to reach out to a part of my network and check up, make sure I keep that connection. Going to different offices in Washington, New York, Dallas, within Austin. Networking from outside, also networking within, building those friendships and relationships. Some of the best pieces of work I've had over the past year or so have been from partners within the firm who have been kind enough to give me work and draw upon my expertise. That takes a lot of trust for a partner to say, I want you to do this piece of work for me, be part of my team, and be client-facing. That tells you they have a lot of trust in you. One reason I joined Bracewell was I saw in the leadership the same leadership I had running the Southern District of Texas. I talked about in the prior podcast the mom-or-how-I-believe people should treat each other within the firm as they were their own mother, that same respect, that same sense of family. I get that here. Recently when I was in New York, I met with a partner and we spent two hours together just getting to know each other. That was incredibly impactful. I saw in him a version of myself.

Khurram Naik: For my final question, do some predictive counseling for Alamdar Hamdani. What do you see for yourself a year or two from now?

Alamdar Hamdani: A year or two from now, the overriding thing I'll still be doing is hustling. That's part of my upbringing since 13 years old. I'm 54 now. It's in my DNA. When we talk in a couple of years, I'll still be hustling. I'll still be taking care of myself, athletically, body-wise, spiritually. I'll also be doing predictive analysis. It's what I did at the Department. It's what I do now. It's what I enjoy. If I'm doing all those things, I'm hoping my book of business is growing. A few years from now, that book of business will be much larger, much more consistent, benefits Bracewell, benefits me, benefits my family. Along the way, I'm hopeful I will learn some new arrows in my quiver. Technology will be different a couple of years from now. I'm hopeful I'm constantly upgrading my skills. And I'm hopeful my network is larger, one that is constantly growing, not stagnant. I've had villages take care of me all along the way, and I'm going to need that village to constantly take care of me and for me to take care of.

Khurram Naik: Bonus question. You mentioned network. What role does network have that's different from an approach driven just by substance and analysis?

Alamdar Hamdani: As I sit here, there are those who build, there are those who are really just thought leaders, smart at what they do. There are those who are service partners. You can be all three. I'm hopeful I'll be all three. But each has a network. None of us doesn't have a network. We all have one. Even if you're a service partner and all you do is service other partners, that's a network you rely on. I can't see any lawyer, or any human, who doesn't have a network. So maybe the question is, do you tap into your network? I tap into mine. Do you want to grow your network? I want to grow mine. That's the real question.

Khurram Naik: I think we've got a good timestamp to revisit two years from now, to see how your predictions have borne out and what about your practice remains the same or has changed. Alamdar, thanks for sharing about this stage in your career. It's not often you get to talk to a U.S. Attorney who is returning to private practice and building. I appreciate you taking the time.

Alamdar Hamdani: Thank you, Khurram. It's always a joy, special to talk to you. I really enjoy our conversations, whether on a podcast or just on a phone call. Not only, of course, have you made this a good podcast, but you have devoted to making into a good friend. I appreciate it.

In this conversation, we dig into what actually compounds across those chapters: the trust-building craft he learned representing indigent defendants and now applies to C-suite clients in mediation, the process-as-substance framework he developed as a magistrate judge managing discovery in the most complex patent cases in the country, the "when you have the last word, don't say the last word" discipline that shaped how he wrote every opinion, and the top-three-priorities test he uses to filter every opportunity against what actually matters.

Keep reading below for the full episode and the complete transcript of our conversation.

Top Insights

Below are the highlights of our conversation:

• Non-Linear Compounds: Shashi's career keeps looping back to the same skill: drawing truth out of people who have a reason not to tell it. He built that skill first as an AUSA, then refined it representing indigent defendants under the CJA, and now uses the exact same muscle on C-suite clients in mediation who are comfortable with silence and have practiced not answering questions.
• CJA Work Is a Training Ground: Big firms that avoid CJA panels are missing one of the best places to train junior lawyers on client counseling. Indigent clients are available to talk. They want to talk. They teach you how to ask questions, how to sit in silence, and how to handle clients who do not trust you by default.
• Process Is Substance on the Bench: The judge's job isn't just to rule; it's to anticipate the choke points in how a case will move and build guardrails in early. Setting a "substantial production" date, adopting Eastern District of Texas-style deposition objection rules, deciding between standardization and customization, those process calls shape the merits just as much as any ruling.
• Marry Credibility to Directness: From the bench, the advocates who stood out answered the question first and explained second. A lot of "well, it depends" is fine if you then walk the judge down the flowchart. Burying the answer or refusing to concede a harmful fact destroys credibility faster than anything else.
• Your Job Is Not Your Identity: Shashi deliberately had his clerks call him by his first name outside chambers, reminded himself the judgeship was a "temp position," and wrote opinions that were measured even when the other side lied. The discipline of suppressing ego on the bench is the same discipline that now helps him empower opposing counsel to close deals in mediation.

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Full Transcript

Khurram Naik: Shashi, I am glad to have you on the podcast. I saw you in action recently on a panel at a conference that a friend curated, and I enjoyed seeing you on the panel. Separately, I interviewed Neel Chatterjee recently and he mentioned, apropos of nothing, that you'd be great on the podcast. So this is a confluence that's bringing you here.

Shashi Kewalramani: Glad to be here. Thank you for thinking of me.

Khurram Naik: Something that's pretty clear from your career is that you've worn a number of hats. You've been in private practice in a range of areas, IP litigation, white collar, criminal defense work. You've been at a large-ish firm, you've had your own practice, you've been an assistant U.S. attorney, you've been a magistrate judge, and you've done these in different jurisdictions. The word you used for this was non-linear. At some point your career was linear, you clerked, you joined a firm, that's linear. Did you prospectively expect to have a non-linear career?

Shashi Kewalramani: Let me go back and correct something in my background. I was never the U.S. Attorney. I was always an assistant U.S. attorney. It's a big difference. One is senatorially approved. One is not. Have I always had a thought of a non-linear path? I would say my first non-linear move was after undergrad, to law school. I never expected to be a lawyer. In the South Asian community at the time, there weren't many lawyers who had matriculated through the U.S. system as lawyers. There may have been some folks who came from countries in Southeast Asia or South Asia who had been lawyers there and then became lawyers here. I had always thought I was going to go to engineering school, go work for a company, and potentially move up the ranks within that company, just as my father did, just as a lot of other folks in my family did. The closest thing to any entrepreneurial spirit I had in my family was folks who were physicians who had to open their own practice. So I don't think I had thoughts about what my future was going to be, whether linear or non-linear. It was just an openness to different paths that came along when I wasn't feeling particularly satisfied with the path I thought I had wanted.

Khurram Naik: You would use the word non-linear to characterize your career. Is that something different than openness?

Shashi Kewalramani: I think they go hand in hand. Linear is what people have in mind. My own linear thought was, get an engineering degree, go to a company, work through the system, move around within the industry, and then retire. Have a good and fulfilling life that way. I now understand, for me and my personality, that I had to be open to different opportunities that came along. When some people pushed back at it like, are you sure you want to do that, the safe path is to stay at the firm, make partner, and then bliss will follow, I didn't think that bliss would follow. When I say non-linear, it's probably more non-linear to other people. There are definitely risk aspects within my own life that are non-linear. For example, leaving a senior associate position at a law firm when you're not far away from partnership to join the U.S. Attorney's Office in another state and taking a 75% pay cut. A lot of people would consider that non-linear. I was leaving the safety of firm life. When I left the court to join JAMS after one term as a magistrate judge, I recognized I was leaving the cocoon, the safety of the federal judiciary, to go out and be an entrepreneur. I'm a little more comfortable with risk-taking. A lot of that is because of circumstances I've been fortunate to be in where I can take those risks. My wife works, so that helps me to allow to take some risks.

Khurram Naik: You mentioned as an associate you didn't see a path in bliss and partnership. Why is that?

Shashi Kewalramani: At least the path I was on, I was an associate, I'd been on trial teams. What I was looking at for people who made that jump to become the lead trial lawyer or lead person at the firm who gets clients, you had to distinguish yourself. The system started changing where there were fewer and fewer trials happening at any big law firm. So the experience wasn't going to be there. I wanted trial experience. I had also been intrigued by moving out of Houston and exploring opportunities outside Texas. That's why I joined and picked the U.S. Attorney's Office. Some folks could have said, I'll join the DA's office to get trial experience. I wanted to do it in a different manner. I was always comfortable in the federal system because of my clerkship and the practice area I was in. I wanted to do more white collar work, document-intensive work, rather than what would be violent crime or narcotics.

Khurram Naik: Did you feel the federal system is more meritocratic? Even in private practice, as a new entry trying to navigate a state court system or a federal court system, did you feel like one would give you a clearer path of success?

Shashi Kewalramani: The federal system is much more rules-based. There is always some level of vagueness in any system, but my feeling was, the judicial officers I had come in contact with as a clerk and practicing, because it is much more rules-based, I did feel I knew the rules of the game. There wasn't like, oh well, so-and-so goes to lunch with so-and-so, so they're going to get a good ruling in state court, not that it is like that. But I knew that was not, or at least perceived it was not, the case in the federal system.

Khurram Naik: You mentioned leaving Texas. What was the significance of leaving Texas for California?

Shashi Kewalramani: A couple of things. The offers I got at the U.S. Attorney's Office: I had interviewed in the Northern District of California, which is in the Bay Area, and the Central District of California. I was about to get an interview there when I accepted the offer in the Northern District. Applying for an assistant U.S. attorney's position is similar to a clerkship. You throw out a bunch of darts and see where you can get in. I had picked five or six jurisdictions that did a lot of white collar work and were places I also wanted to live. I had lived overseas as a child, but after high school I pretty much spent my whole career in Texas. I would come out to California with some frequency and I really liked it. I liked the feel of the place, I liked the opportunities out here, and I was lucky enough to get an offer.

Khurram Naik: Why were you interested in moving into white collar work?

Shashi Kewalramani: It was closer to the type of work I was doing, which was commercial litigation and IP litigation. So it's looking through a lot of documents. It also has, perception-wise, more transferability back to the private sector. I had never intended to be an assistant U.S. attorney for my career. It was a period of time. I was planning to go to a good U.S. Attorney's Office, get trial experience, do white collar work where you were also against attorneys usually at big firms, and then go back into private practice in big law.

Shashi's decision to leave a near-partnership track for a 75% pay cut at the U.S. Attorney's Office is the same class of decision Manisha Sheth walked through in her episode, leaving a partnership to serve in government and bet on herself. Listen to my conversation with Manisha Sheth.

Khurram Naik: Why is it that you had some early skepticism over institutions that attachment to them?

Shashi Kewalramani: I wouldn't say it's an issue with institutions. I would say it was something I didn't see myself at that time with the knowledge I had being a lifetime prosecutor. I thought it would be a four-to-seven-year term, which was very common in some of these U.S. Attorney's Offices, particularly in the Northern District of California, Central District, Eastern District of New York, Southern District of New York. It was very common to do five to seven years, get good experience, work really hard, and then go back into private practice. Versus some other offices around the country where people joined the office and stayed there until they retire.

Khurram Naik: Heading into that tenure, what did you in fact get that you thought you'd get, and what surprised you?

Shashi Kewalramani: The biggest surprise was the number and type of people I came in contact with at the U.S. Attorney's Office and interacting with Main Justice in the 2003–2004 time period. I really enjoyed the breadth of experiences people had. At the law firm, people had a pretty common route: undergrad, law school, clerkship, firm. It was very common. There weren't a lot of folks who had, let's say, gone undergrad, then taught for a period of time or done Teach for America, or joined the military and then gone back to law school and then clerked and then come to the firm. The firm I was working at was much more staid. At the U.S. Attorney's Office people had a lot of varied paths to the law. People taught, people worked overseas, people were in government at some point and decided to go back to law school and join the U.S. Attorney's Office. That was really refreshing, to see that there was not a single path to any career goal. I had been exposed to, there are steps and you follow those steps and it leads to an outcome. But sometimes what we perceive as linear steps don't necessarily lead to the goal. In fact they do, because they expose you to different ideas that tell you what you're going to enjoy and what you may be good at.

Khurram Naik: What's another instance in your career where you experienced an analogous insight?

Shashi Kewalramani: I saw that at the court too, where the people who had been selected for judicial positions hadn't necessarily just gone through what you would consider the steps of big law then getting on the bench. There were people who came from varied walks of life, legal defense funds, public interest entities, government entities, non-government entities, but still succeeded by getting nominated and appointed as a district judge or an appellate judge.

Khurram Naik: Can you point to any specific takeaways from people who walked down different paths?

Shashi Kewalramani: They learned a lot about the world, and I think it made them better people and also better professionals, because they weren't thinking in the way somebody who had just gone through school. They had experienced the world. They brought insight that sometimes I wouldn't think of, and they had unique experiences that gave them some flexibility and insight on how to deal with things. I remember somebody from the U.S. Attorney's Office who had been in the military before they joined, then went to law school. We were dealing with a case and he told me the defense attorney was taking positions that weren't probably beneficial to his client. I was having a hard time reconciling, why are you not doing things in the best interest of your client? I was naive. He explained to me certain things about the real world and how he grew up, the distrust that was probably there between the client and the counsel because of the counsel's relationship with the U.S. Attorney's Office, and that we had to recognize the client and counsel probably had internal friction we had to account for and give some grace to.

Khurram Naik: Did that impact how you took on criminal defense matters through the CJA after you left the bench? Did that impact how you approached your practice?

Shashi Kewalramani: 100%. Because I appreciated that not only being a court-appointed attorney may put me in a certain light with my client, but also I'd been a former assistant U.S. attorney. I would recognize that folks who have been through the criminal justice system, often rightfully so, had hesitancy of disclosing facts to me because they didn't fully trust me. I had to build up that trust over time. That taught me I had to give people space to trust me. I also had to take actions that would allow them to trust me. It couldn't just be words. I had to act in ways that showed I cared about their case and that I was going to fight for them.

Khurram Naik: What specifically didn't they trust?

Shashi Kewalramani: One of the things they don't trust: certain clients of mine couldn't afford an attorney. Under the CJA system, the court appoints you and the court pays for it. They are viewing it as, you're just part of, you and the judge are aligned, and judges in the past have done me wrong, therefore you will do me wrong. Oftentimes the first step in a criminal case is a bail hearing, and oftentimes people wouldn't fight for bail. I always believe the law requires bail except for extraordinary circumstances, and I would voice that position aggressively. The first time they meet me, I'm going to fight for you from day one.

Khurram Naik: What did you do to facilitate trust?

Shashi Kewalramani: Give the folks time. You have to fight for them right from the get-go and be fully transparent with your client and explain why you're doing what you're doing. Full transparency is a big thing in every aspect of garnering trust, both as an attorney and as a judge. In my opinions I wanted to put in everything I was thinking about as a basis for why I came to a decision. You'd see certain rulings that say "I find there's a fact issue, period." Okay, you've got to give me something more than that. Giving time, giving transparency. I would often meet with my clients for hours. I would go meet them in jail if they were in custody for hours, to talk and learn about them and give them the opportunity to speak freely. The fact that I was willing to come into the jail for eight hours in one day and be there as long as they wanted showed I mean what I say. I'm going to treat you just like the $700-an-hour client. Even though you technically aren't paying for me, you're going to get the service that all my clients get.

Khurram Naik: Someone trying to build a practice might say, I could use my time on the $700 client. What mistake are those lawyers making?

Shashi Kewalramani: I was warned about that by other attorneys: you need to stop doing CJA cases because it's taking away from your other cases and your other marketing. My sense is there's a public duty obligation. In the Northern District of California, big law firms would be on CJA panels not only as a way to get court contact with clients, but also to train younger associates on interacting with clients. Rather than them sitting at a deposition and watching, you could take younger attorneys to the jail cell or the meeting room and meet with clients. You have a lot more freedom and time speaking with a client in that setting who wants to talk to you, versus private clients who may not want to talk: give me a deliverable in two weeks, we'll talk then. CJA clients are amenable to strategizing, and it gives you great insight into thought processes. Big firms should do this not only as part of being at the bar but as a great training opportunity. As a former federal magistrate judge, I could say I appreciated when I saw somebody from a big or medium or small firm in my courtroom taking on a CJA case. My level of respect for them went up, and that transfers to other practices and other cases they may have.

Khurram Naik: What's the tangible benefit of that respect?

Shashi Kewalramani: Attorneys representing indigent defendants are in court more frequently. When I see an attorney more frequently, I feel they're less likely to play games with me, because they're going to be in front of me in another case. When they're making arguments, they know if I catch them in a lie, not a lie but a misrepresentation or a misleading thing, it's going to transfer to their other client. Human nature is not to say, I'll do this for the benefit of one and then lose my reputation for all my other cases. It's one more opportunity to build a good reputation with the judiciary.

Khurram Naik: How can skills from indigent-client work transfer to a big business client?

Shashi Kewalramani: One skill transfer is learning how to obtain information that's relevant to the case. Learning how to be patient. Learning to let people speak and tell you what they want to tell you. Practice makes you better. It makes you better at getting information out of whether it's the engineer who gave the specification for the patent or somebody who is not trying to tell you the whole truth about something else. Often the hardest thing to do representing a client is getting the truth out of your own client, letting them tell you where the bad issues are. Sometimes you have to sit back and listen. Some people are uncomfortable with silence. I have found the higher up the C-suite, people are very comfortable with silence. They're smart. They don't want to say more than they have to. Sometimes you have to know how to ask those questions and see the tactics that are taken to divert you from giving an answer. Folks who have, especially indigent, not "criminals," people who have done a bad thing, one of the best lines I've heard was, just because somebody did a bad thing doesn't mean they're a bad person. Sometimes these folks are very smart. They've had to get by in society with wits and intelligence, and you learn things through that process that are transferable to speaking with your own clients. Often your own clients at big companies are amateurs compared to what folks on the streets have had to do to get by.

Khurram Naik: Is there a moment that comes to mind, someone particularly sophisticated you represented in the CJA context, where you learned a technique that struck you?

Shashi Kewalramani: The biggest tell was when somebody wouldn't answer the question in a conference room when it's just you and them. That's the biggest tell. That's something I learned to deal with with my other clients. Sometimes people just need the space and grace to get to that point in their head to tell you the bad thing. Sometimes people need to be pushed. I can't tell you when one approach is appropriate versus the other. I've done it so many times you have a sense of, if I push here, is this going to rupture the relationship, or is this what this particular person needs?

Khurram Naik: Has there been a moment where you've taken something that was objectively a bad fact and inverted that into something beneficial or at least neutral?

Shashi Kewalramani: In certain white collar cases and civil matters, and particularly in mediation, one of the mechanisms to really understand whether a bad fact can be neutralized or at least diminished is, give me the context of this document. That allows folks to then discuss, no, this document isn't as bad as you think, and tell you why. Being able to just sit there sometimes for five minutes in silence while that person is talking, you do this for five minutes, it sounds like a long time, but just sitting there and letting folks speak, sometimes they give you the answer that actually does neutralize it. Or in their explanation they come to realize, yeah, this is a bad one. They internalize the aspect of the document that's going to be harmful, without me having to tell them.

Khurram Naik: You mentioned the CJA panels were much more active in the Northern District than the Central. You've been a prosecutor, magistrate judge, in private practice across two jurisdictions. What's your vantage point on how different districts actually are?

Shashi Kewalramani: The Northern District of California is a lot more tech-heavy, down Silicon Valley. San Francisco has historically been a financial center. There's a tradition of a lot of financial businesses as well as tech businesses in Northern California. It also had an SEC office, as does the Central District. San Francisco has an antitrust division office; the Central District does not. As a result of certain offices with priorities in particular jurisdictions, the practices have morphed to accommodate those enforcement areas. San Francisco has a lot more private antitrust cases than the Central District. Another district that has a lot of antitrust cases is the Eastern District of Pennsylvania. Those formed over years for multiple reasons.

Shashi Kewalramani: Central District of California is just massive, 19 million people. There are a fair number of historically narcotics and violent crime prosecutions at larger scale in the Central District than the Northern District. You had differences in practices of the prosecutors and investigators who would come to these jurisdictions. From the judiciary standpoint, you would see different types of cases, because ultimately we are the client, the attorneys are our clients. In the Northern District you would get a lot more IP, antitrust, and SEC, though there would be some guns and drugs and violent crime. It wasn't nearly as much as the judges in the Central District have to deal with. In the Central District there's a lot of contract cases. There's a lot of commerce, not only related to contracts but also in the entertainment industry, which is big in the LA courthouse. In the Orange County courthouse, a lot of real estate and IP. Riverside has a lot of contract commercial matters and civil rights investigations just because of the nature of the population. Even within the districts, the divisions have a different focus because of the types of cases generated within the counties that comprise the division.

Khurram Naik: What's the impact on the judiciary? What changes for judges as a product of these pockets of expertise?

Shashi Kewalramani: I can speak to myself. There's different ways you manage the case based on the nature of the case. If it's a PI case involving a trucking accident, different discovery, different timeline to get to trial, versus an IP case which may have international components, different motions, different discovery aspects. The more you see of a particular type of case, the more you can anticipate what problems are going to arise and how to put in safeguards in the management of the case. In a home construction contract case versus an IP case, you have to be mindful of what's the scope of discovery and how is that going to impact the deadlines you're setting. Should you put in an end-of-discovery date, or should you put in a date before that called a "substantial production of discovery" deadline, because there may be lingering things that happen. Working with a client in a different country that has different privacy laws. Whereas a two-party contract case has a pretty finite amount of material.

Khurram Naik: Do you think there's a benefit to codifying that in some way, so that sets the norm for peers on the bench?

Shashi Kewalramani: Certain courts have local rules for patent cases. Northern District does, Eastern District of Texas does. Central District of California, there's been talk about it for decades and they have not been adopted. What happens sometimes is the parties will agree, we'd like to use the Northern District of California rules for patent cases in this matter. Some people like that it codifies it. Some people believe it takes away the bespoke handling of every particular case. You have voices on either side. Fundamentally, you can't make judges do something they don't want to do.

Khurram Naik: This impact of procedure and process has been a running theme in this podcast. Judge Kennelly raised it in his episode, talking about the centrality of process for the administration of justice. Judge Chhabria picked up the same theme. It seems to me an underrated theme from the judiciary is the role of process in the administration of justice. The other thing I'm noticing is this tradeoff between standardization and customization for a particular matter. That's a canonical tradeoff judges consider. Are there other canonical tradeoffs?

Shashi's framing of process as substance, the set of discovery and pretrial calls that shape the merits just as much as any ruling, is exactly what Judge Vince Chhabria described in his episode as the core work of the bench. Listen to my conversation with Judge Vince Chhabria.

Shashi Kewalramani: Because I was a magistrate judge I had a lot of discovery matters. There are certain viewpoints that, look, the attorneys will deal with it, and when they have a problem they'll bring it to you. Versus putting in procedures to avoid those issues being brought to you. For example, depositions. If a party had consented to me, I could control a lot of the discovery issues at the beginning of the case. I would adopt the rules with respect to objections at depositions from the Eastern District of Texas, which were, you can only object to form, or you can only tell your client not to answer based on attorney-client privilege or work product doctrine, or you could submit the objection of non-responsive. That does away with speaking objections. In California state court they are supposed to do that. I had enough issues come up before me with speaking objections that were taking depositions beyond the seven-hour time limit that I thought it would be helpful to say, here are the rules, you're going to have these are the only objections you're going to have, and then I don't want to hear, I think you have less of a leg to stand on saying we didn't get all the information we needed in the seven hours allowed under the federal rules and we need more time. There is an involvement in the process that I thought would be beneficial to what I viewed as my clients, the attorneys. Other folks said, look, we're just refs, until we see a foul we just sit back.

Khurram Naik: My experience with magistrate judges is they're feeling so much of the discovery issues across jurisdictions. Article III judges are obviously the flashy role. What do you think people are missing from the opportunity of being on the bench as a magistrate judge, practicing before a magistrate judge, or clerking for one?

Shashi Kewalramani: The role is changing. A lot of districts now have consent programs. The Northern District of California has historically had one. When a case is assigned, in a civil case, if it got assigned to a magistrate judge, a lot of parties will consent. That's becoming more common in the Central District and is very common in the Northern District. So the role is changing. I thought it was a great opportunity. You're in the federal system, you're getting a lot of consent, you are dealing with a lot of the nitty-gritty stuff that happens in cases that actually can help move the process along efficiently. I thought it was a great opportunity for me to learn also how to think like a judge and what is really going on behind closed doors. Even beyond clerking. I clerked for a district judge, so when I became a magistrate judge I had a sense of what happened, but not really. You don't know it until you do it.

Shashi Kewalramani: In the Central District of California, the magistrate judges and district judges interact fairly regularly. In certain courthouses, for the vast majority, there was no distinction. You would not hear a district judge say, "This is Magistrate Judge So-and-So, I'm District Judge So-and-So." You just didn't hear that. You get a lot of insight into the whole process. As far as clerking for a magistrate judge, I just got off the phone with a former clerk yesterday who was arguing with his law firm because somebody wanted to go off and clerk for a magistrate judge. The biggest thing: they will become a better writer because of the product we have to get through. Especially in the busy districts, how many motions we have to decide. It really trains you to become a better, more efficient writer who gets to the point of what you're trying to convey. You get to see a lot of argument by attorneys. You can pop into a courtroom and say, oh, we hear so-and-so is giving a closing, go check it out.

Khurram Naik: What surprised you the most about how judges work, either in opinions or in the administration of cases?

Shashi Kewalramani: The volume of cases we have to deal with and the number of complex motions we have to address in a timely fashion in order to really deliver justice to the parties. You hear, oh, we have this many cases, but until you're there seeing the flood and the type of cases: social security appeals, bankruptcy matters. The most complex issues were often in pro se matters, particularly pro se 1983 cases, because a party would use some loosey-goosey language and we would have to ferret out, what's the constitutional basis for this? As a magistrate judge, we would have to screen these 1983 complaints from often prisoners and pro se folks, which have gotten better with AI. I remember handing a complaint to my law clerk: here's a new con law exam, what are Gideon and Gideon v. Wainwright, right? A pro se person raising these complex constitutional ideas in the most mundane and surprising ways.

Khurram Naik: From the bench, it's not about dollar value, it's about legal issues. That reminds me of a previous episode with Louis Tompros, in a very different context. He identified an opportunity to look at pro se patent application filings and look for ones that raised interesting legal issues, then argued one at the Federal Circuit. It's called In re Klein. It involved the doctrine of obviousness in the wake of the KSR Supreme Court decision and got a precedential opinion and changed the patent office's examination policies. These seemingly minor matters can have a big impact.

Khurram is right that Louis Tompros and I just talked about exactly that discipline: scanning for overlooked cases with big legal upside and stepping in pro bono. It's the same instinct Shashi describes from the bench, treating pro se matters as serious legal work. Listen to my conversation with Louis Tompros.

Khurram Naik: From the bench, you mentioned you're like a gym rat. In the gym there are different theories for what's effective. Sometimes you hear about certain advocates, such and such in the Supreme Court, they can get away with that because of their name. Maybe it's extremely personality-driven, or there are perfect approaches. What have you learned about advocacy techniques from the bench? Are there archetypes?

Shashi Kewalramani: Let's split it into two: advocacy to the bench in a legal matter, versus advocacy to a jury. With the bench, the common theme I saw across every advocate was, they answered the question first thing out of the box. They didn't preface it with a bunch of stuff. They answered the question, then gave the explanation. That was really appreciated and set somebody head and shoulders above the next person. The answer could be, "well, it depends," the most lawyerly of all answers, and then anticipate the next question. If we're going to go down this flowchart, let's create the flowchart. The best advocates would take you down that flowchart. The people who weren't that good would not. All of that is wrapped up with credibility. Within, say, four attorneys, two on either side, the attorney I could trust the most was the one who gave me that direct answer quickly with supporting basis, either legal or factual. It all comes down to credibility. Who am I going to trust when I don't have everything in front of me? Folks would first answer the question, be succinct, not necessarily succinct as in not giving requisite detail, but would sometimes give you the answer that's harmful to them, "well, no, we don't have that," and that again builds credibility, which is the cornerstone of everything. If you lose credibility, you're pretty much done arguing before a court.

Shashi Kewalramani: In front of a jury, what I found was there is no archetypal manner. People you would think were prototypically "smooth" are not necessarily winning. People who aren't prototypically smooth are winning day in, day out. That comes from genuineness and authenticity. Big thing is not being a jerk. Juries pick up on that, judges pick up on that. You can fight for your client hard without being a jerk. I don't know if there's a single type. With juries, if you get caught misleading or misrepresenting something, particularly a document, it's hard to come back from that.

Khurram Naik: What was it like when you first got on the bench? Was there an early moment when you went from doing the work of a judge to feeling like a judge?

Shashi Kewalramani: This was important to me. I never wanted to get wrapped up feeling like a judge. There's a story of Roman emperors who would have somebody whispering in their ear, and I'm not saying a judge is a Roman emperor, but there is such a thing as robe-itis. People start to believe, oh, I am funny, people laugh at my jokes, oh, I am smart. I would affirmatively take steps. My clerks outside the presence of other judges and not at bar events, I asked them to call me by my first name. I'd say it's a security issue. If we're going to lunch someplace, I don't want you to call me "judge," just call me Shashi. Those are little steps. I went through my whole career with some level of imposter syndrome of, thank you God, there are other people who could do this. You get comfortable with it, I can handle this job just as well as anybody else. But I always kept in mind that my job as a judge was a temp position I was holding. If I retired or if I passed, my chambers would go on to somebody else and I would be forgotten maybe a year later tops. That's just the ephemeral nature of the world. I was mindful I was a public servant. My job was to continue to serve my clients, which are the bar. I would remind all our clerks, we are not special, we are all replaceable, we have a job to do.

Khurram Naik: Is there something about your decision-making process from your time on the bench?

Shashi Kewalramani: As an advocate, you know what your position is and you're forwarding that position with a larger strategy in mind. As a judge, one thing you would try to separate is the effect of your ruling, oh, I don't like this person, or I like this person, and you had to separate that from the ruling. It was very much a chips-fall-where-they-may attitude. Michael Lewis did a podcast series about judges. He talked about how we have changed as a culture of attacking the ref. It permeates through society when a judge makes a ruling, oh, you're doing it for some nefarious reason, you suck, we don't have to follow it. I was mindful I'm not the player, I have a role: I make my ruling and the chips fall where they may. You're going to displease somebody.

Shashi Kewalramani: One thing in writing: I would write very, very dry, because you don't want to give any indication it was based on personal animus. There's this Parsi approach to life: "say kind words, think good thoughts, do good deeds." The hardest thing is think good thoughts. You start by acting and doing good things, and then hopefully it ingrains and you start thinking good thoughts. So the performative leads to the substantive. Saying things kindly, being polite, being measured, then you start thinking that way. You have clerks saying, "your honor, this guy just lied about the facts." I would rewrite that as "counsel does not provide proof for this statement. However, looking at the evidence…" You move on. You don't need to comment on what somebody did when you have the power to make the ruling. There was an NBA ref whose dad was a Chicago PD officer, and he said, "when you have the last word, don't say the last word." I don't need to be snarky. It is what it is.

Khurram Naik: Is there a decision you're most proud of?

Shashi Kewalramani: I don't think there's a decision. I'm most proud that in criminal matters, when folks were before me in detention and bail hearings, I heard comments from attorneys saying, even though you detained my client, he really appreciated you listening to him. The fact that I tried to give everybody the respect they were due, and actively suppress any ego, I think has helped me not only as a judicial officer but in private practice now, and has made me a better person at home. You have to internalize suppressing your ego. I didn't view myself as the most important person in the courtroom. It was the client's courtroom. We just happen to be there to facilitate resolution.

Khurram Naik: Were there experiences before a judge that helped you get reps in suppressing ego?

Shashi Kewalramani: Certain judges I would model myself after. In the Northern District in particular, Judge D. Lowell Jensen was a prince of a man. He would say my name correctly, which was nice. "Shashi Kewalramani." He took the time to learn how to pronounce it. He had been the former district attorney of Alameda County, then an assistant attorney general under Ed Meese and Ronald Reagan, even though I believe he was a registered Democrat, and then got back on the bench. I was at a mall with my one-year-old daughter and I hear "Shashi!" He was just that type of a guy. No ego. I was like, "oh, Judge," and he said, "no, no, it's Lowell." Everybody would clamor to get in his courtroom. Not that it was going to be easy, but it was going to be fair. There were certain judicial officers I would see who were just very kind, and it would let you know, yeah, they were credentialed, they had experience, but there was an aspect of serendipity to where they are, and that was a recognition I really tried to internalize.

Khurram Naik: Let's talk about your transition to mediation. Mediation is different from the bench. You mentioned this concept of taking a client-centric approach. What are the skills that transfer, and what is the biggest departure?

Shashi Kewalramani: What transfers: being trained to listen. Some people have it innately. I had to work on mine, and I got much better at it as a judge, and before that as a criminal defense attorney. Recognizing, in a criminal defense or a civil case setting on the bench, I would be very mindful of anything I said about counsel, especially in front of their client and in any written opinion. If a criminal defense attorney is making a bad argument, I can't use the word "ridiculous." I would be mindful of making any comment because it could harm the attorney-client relationship. Similarly in a civil case, if I said counsel misled me, that order might go to in-house counsel, who might read into it and say, this judge doesn't like this attorney, maybe I need to find new counsel. My words had ramifications beyond what was said in the courtroom. I trained on that. It really became internalized. If I was thinking something, just keep it to yourself. Often upon reflection, the attorney's argument wasn't ridiculous, I hear where they're coming from. It trained me to be a little more mindful of my own prejudices and biases and tamp those down. That has transferred well into private practice, both arbitrations, where I'm essentially in court, and mediations. In a mediation I have to empower counsel. When I'm in the other room, he or she is in the jury room with the client trying to say, what the judge said kind of makes sense. I need to empower somebody and give them the ammo to persuade their client.

Khurram Naik: What's been hard? What's been surprisingly easy?

Shashi Kewalramani: Hard: I'm still surprised at how certain attorneys don't respond to emails or texts in a timely fashion. I have a theory that has been borne out: the most successful attorneys, the biggest names, are actually the most responsive. There's a direct correlation between successful and responsive. When I sent an email from the bench, I'd get a response back fairly quickly. Now, people just don't respond. Easy: because of my involvement in a lot of bar activities before I was on the bench, reaching out to networks I had been part of has been relatively easy. I'm not as introverted as I thought I was. Reaching out to folks I did mediations for on the court and getting such a positive response. I tell them, I could have been the biggest jerk, you saw what I was in a mediation and I wasn't, so what do you think I'm going to be in private practice? I'm going to be forceful, but always polite. People sometimes like that in a settlement conference. They don't want a notecarrier. "Suzy thinks they're cute, well, Tom thinks they're cute too." There's no value add to that. I'll make a call. I think this argument's strong, I think this argument's weak. They may disagree with me, but you've got to make a call. That's a value-add and a deliverable attorneys can take back to their clients.

Khurram Naik: How are you thinking about positioning yourself given there are a number of other judges at JAMS? What's your core differentiation?

Shashi Kewalramani: There's showing versus saying. In every mediation, I prepare a lot. People see that when I know the details of the case. There's a huge bell curve in the mediation business. A big middle, smaller tails on either side. I want to be on the smaller tail on the good side. My background in IP, complex commercial cases, securities work, and a very good understanding of federal statutes positions me more as a commercial and federal person rather than, I'm not your best person for a car wreck case and evaluation of soft injuries. My rate is going to dictate that as well. My sweet spot is commercial, IP, securities, trade secrets.

Khurram Naik: Do you have a preliminary view on niching versus broader-based approach? Chasing whales versus mid-market matters?

Shashi Kewalramani: In the commercial world, contracts, securities, IP, trade secrets, there's a lot of those cases out there. The dollar amounts don't have to be that high to warrant retaining someone like me. Let's say damages above $2 million, there's a lot of cases like that in the commercial realm. The practice picks you. I have resolved cases for particular law firms and now they're coming to me with slightly adjacent subject matters to the ones I helped them on. The response is, we just want somebody who's well prepared and will dig into the details, and the dollar amount meets what we can tell our client he's worth for the day. Even though I'm hired for the day in mediations, it's on average about 20 hours per mediation in prep, the mediation, and post-prep to get the deal done.

Khurram Naik: How do you think about the trade-offs of a roster of clients? 80% from three firms versus diversified?

Shashi Kewalramani: I want as broad a roster as possible. I'm not just focusing on big firms. I have a lot of colleagues and cases at smaller firms on the plaintiff side. Where business comes from is just like any marketing: you don't know where it's going to come from, you just need to put as many seeds out there. I am mindful I'm not just catering to big firms. I would be hesitant to agree to, hey, we want you for X number of cases to the exclusion of others, for two reasons. One, I don't want to be beholden in that regard. Two, it creates an impression of not being impartial. Especially as a mediator or arbitrator, I don't want to be known as beholden to certain firms.

Khurram Naik: Is there a differentiating point of view you have about how mediation or arbitration is conducted?

Shashi Kewalramani: I can tell you what I've heard from attorneys who have hired me. What they appreciate is the prep and the deliverable in the sense of a mediator's proposal that isn't just a paragraph like, you should settle for X. Everybody needs to know the why. If you're settling a case for over $2 million and you've got to go to in-house counsel, they need to know why they should pay or accept this money. I always try to explain why I'm making a particular recommendation. That's an extension of my job as a judge, where I would write sometimes a little more extensively than I needed to, because I felt the parties needed to have insight into the thinking, into how I came to a conclusion. That allows the parties to have a meaningful discussion after the mediation is ended, while I'm still involved. I try to provide an extensive deliverable the parties can rely on if they don't resolve it then.

Khurram Naik: Two questions to wrap up, both recurring themes. One interesting frame: strategy versus opportunism. You've talked about strategy to decision-making in your career, but I'm also hearing opportunistic movement. Do you identify with one more than the other?

Shashi Kewalramani: Your strategy has to change as your life changes. There's a difference between a 27-year-old with no kids and no spouse who can take more risks, versus having other responsibilities. You also learn about yourself as you grow. As a lawyer, performance is table stakes. You have to win, you have to be responsive. Those are all baseline. How do you differentiate yourself? You have to take a look at your own strengths and weaknesses and find where you could maximize your abilities. Going back to the gym rat thing, I'm not six-three, I can't dunk, I'm not going to play forward. Where do you fit, intellectually, geographically, on your platform? Where do you see a successful career five years down the road? One of the hardest things to do is predict where you're going to be more than five years from now. Life changes. You should have a general plan and then it gets hazier. Then you have to be open-minded. One of the hardest things is to identify the three most important things to you in life. I'm borrowing this from Stephen Covey. You write down the three or four most important things, and then how does every decision go to those things? The hard part is identifying those three things and then how every opportunity fits within that decision. I've tried to do that from time to time. Sit down and write: what are the three most important things to me, and how does my decision professionally impact those three things personally and professionally?

Khurram Naik: That's an interesting observation. It's exactly how my wife, who's my business partner as well, approaches ourselves. We share the same three priorities around work, family, and business. That means to the exclusion of things like travel, friendship, creativity, which is not to say we don't experience any of those, but they have to align with those first three. What I'll add is, I think what's hard, I don't think we had a hard time identifying those, I think we found it really hard to apply those. That involves trade-offs.

Khurram Naik: My other question: you proposed this concept, non-linearity. You've been around the block. What do you see as prospectively the value of this experience for something else?

Shashi Kewalramani: Prospectively, based on my life stage with our kids and family, I'm 54. I continue to keep an open mind. You never know what opportunities are going to come down the road. If the right opportunity came along, for example, would I pivot from being a mediator and arbitrator at JAMS? Yeah, I would have to think about it. I'm not wedded to, this is who I am, I am a former judge who is a mediator. It is not part of my identity. Work is separate and apart from my identity of who I am. That takes time and confidence to be comfortable with, because in our society people ask you, what do you do, as if that is who you are. You have to be comfortable saying, what I do is X, but that's not who I am. I continue to remain open-minded. When I say non-linear, I compare it to a lot of my peers who haven't done plaintiff-side work, haven't done defense-side work, haven't worked at a big firm, haven't worked at the U.S. Attorney's Office, haven't been a judge, haven't gone out to the mediation world. It's non-linear in the sense that it's not common. Is there a through line? Probably. We can always draw a through line through everything, that's just statistics. I continue to remain open-minded to opportunities. This is not who I am. This is what I'm doing now to fulfill those top three goals in my life.

Khurram Naik: I'm looking forward to what you do with this chapter and what the next chapter brings.

Shashi Kewalramani: I appreciate that. Thank you so much for your time.

When a partner reads your representative matters, they should come away with two conclusions:

1. You understand the client's ultimate objectives.
2. You show high agency in achieving them.

The Approach

Here's the approach we use:

• Situation. This isn't just procedural posture. Was the firm brought in three months from trial? Did it involve a mission-critical product? Was there business risk beyond the litigation itself?
• Impact. This is not just the disposition of the matter. Did the client avoid a major disruption? Did the client send more work to the firm as a result? That benefits both client and firm.
• Role. This is the bridge between Situation and Impact. It reflects judgment, ownership, and contribution under pressure.

Foundation Building

The representative matters lay the foundation for interviews. They're case studies for how you'll be helpful to the firm. Establishing that you are helpful to the firm creates the conditions for an offer.

When you use this approach, the representative matters transforms from a list of tasks to a guide that creates offers. This is especially important when you're actively interviewing with multiple firms and need to stand out.

Key Takeaways

Stop treating representative matters as a task list. Instead, frame each matter around Situation, Impact, and Role. Show partners you understand client objectives and demonstrate high agency in achieving them.

Your representative matters aren't just a record of what you did. They're your proof of how you think and what you'll bring to a new firm. And understanding why working with multiple recruiters backfires can help you present these matters more strategically during your search.

Use this framework to turn your experience into offers.

The Beginning

I started the podcast in October 2020 with a loose goal: talk to interesting people about the ideas and decisions that shaped their careers.

My network reshaped the podcast. The podcast guests pointed me to other lawyers I should interview. Sometimes these were their friends. Other times they suggested people they admired but didn't know.

The Evolution

That iterative process led to the podcast's mission today: deep dives with lawyers about the principles behind their careers and the patterns across lawyers for success.

It's the same process that pulled me into recruiting: not by deciding to "start a recruiting business," but by becoming useful to lawyers in my network through conversations, ideas, and relationships.

The Lesson

A relationship-first approach does more than grow an audience. It reveals where you are useful. And if you keep following that thread, it often creates the next opportunity before you can conceive it.

This is why working with multiple recruiters backfires for many lawyers. The best opportunities come from deep relationships, not scattered connections.

Start with conversations. Follow the thread. The business will reveal itself.

In this conversation, Louis, a partner at WilmerHale, Harvard Law lecturer, and one of the country's most versatile IP litigators, walks us through what he's learned building a career on bounded adjacent bets: the trademark mock trial he did as a favor that turned into a real trial he won, the Pepe the Frog copyright litigation that positioned him for the AI copyright wave, and the teaching work that made him a sharper trial lawyer. We get into his three-audience theory of trial, the "marry the judge" rule, and why "when it stops being fun, I'll stop doing it" is the best piece of career advice he has ever given a new partner.

Keep reading below for the full episode and the complete transcript of our conversation.

Top Insights

Below are the highlights of our conversation:

• Create Your Own Reps: Louis didn't wait for a Federal Circuit argument to be handed down. He watched the docket for pro se inventor appeals until he found one, Arnold Klein's hummingbird-nectar patent, where the analogous-art doctrine was squarely teed up post-KSR. He offered to take it pro bono, won the argument, and the Federal Circuit issued a presidential opinion. That one move reframed his career as an opportunist rather than a passenger.
• Bounded Adjacent Bets: Louis believes getting laser-focused creates blind spots. Patent plus copyright, trial plus appellate, plaintiff plus defense, each pair makes the other sharper. He credits his copyright experience with spotting a disgorgement-of-profits theory that the other side was smuggling into a patent damages case, which the Federal Circuit ultimately rejected.
• The Three Audiences (and a Fourth): Every trial is a simultaneous performance for the judge, the jury, and the court of appeals. Same words, same slides, same witnesses. The appellate piece gets forgotten in the thick of trial and costs cases. The fourth audience is the client, and sometimes you can win on the merits and still miss what the client actually needed.
• Marry the Judge: Juries arrive distrusting lawyers and overwhelmed by technology. The only person in the room they trust is the judge. So your job is to create the impression that the judge is on your side. That means not piling on objections to preserve the record, projecting calm, and letting the other side draw the judge's visible irritation.
• When It Stops Being Fun, Stop Doing It: Louis's favorite New Yorker cartoon shows an ant pushing a boulder up a hill, captioned, "When it stops being fun, I'll stop doing it." It's his baseline career advice. Partnership at a top firm opens many doors, and there are too many opportunities to spend years in a rut. The unhappy lawyer's biggest mistake is to keep doing the thing.

Listen Now

Catch the full episode on your favorite podcast platform.

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Full Transcript

Khurram Naik: Louis, I'm really happy to have you here. In many ways this episode is about 13 years in the making. If I knew I was going to have a podcast 13 years ago, this is one of the ones I thought I was going to do. So I'm excited to have you on.

Louis Tompros: I really appreciate being here. Thanks so much.

Khurram Naik: How I met you 13 years ago was, I was part of an advocacy challenge for an event at the Linn Inn in Chicago as a 3L. Judge Linn was part of an en banc panel where we as advocates argued an issue, and then we all retreated afterwards to talk about it. Judge Linn asked me about my career plans and I told him I was looking to be a patent litigator at a large law firm and working my way into that. He said, well, the entrepreneurial approach you're taking reminds me of one of my former clerks, Louis Tompros, and some of the things he did. One in particular was that he ended up arguing a matter at the Federal Circuit and the Federal Circuit issued a presidential opinion. But how he did that was through a very entrepreneurial route. So I wonder if you can talk about In re Klein.

Louis Tompros: Sure. This was before I was a partner. I was a counsel here at WilmerHale, very interested in Federal Circuit cases. I'd gotten a chance to do a lot of Federal Circuit briefing and second-chair some of those, and obviously clerked there. I started following the Federal Circuit docket. At the time you could see case filings as they hit using various tools. I was kind of mostly curious to see what was going on. Then it occurred to me that there were a number of cases getting filed pro se by inventors, or by small companies that are essentially a single person, to bring the case. The Federal Circuit has a policy that every case where there's representation, where there's a lawyer, automatically gets oral argument. I thought, I wonder if any of these have issues interesting enough where I could get an oral argument out of going in to represent, just on a pro bono basis, one of these inventors.

Louis Tompros: I just kept track of it. It probably took four, five, maybe six months of reading the opening briefs folks would file in these cases pro se, until I found this one by a guy named Arnold Klein, an individual inventor. He had this hummingbird-related business. Out of his backyard, he was making hummingbird nectar mixers. He had been denied his patent on this. He worked with an attorney to try to get a patent on the design of this particular nectar mixer with this dividable structure. It had been rejected in part because of some old inventions on old card-catalog dividers. This was pretty soon after the Federal Circuit had decided the cases that followed the Supreme Court's decision in KSR on obviousness. One of the big open questions was whether this old Federal Circuit doctrine called the analogous art doctrine still applied after KSR. I was reading the opening brief Mr. Klein had filed, and it occurred to me that he had a pretty good argument that if the analogous art doctrine were still the law, the patent office made a huge mistake in rejecting his application.

Louis Tompros: I called him and we chatted for a bit. He was really interested in having me help with the case. He was willing to hand this over to this young lawyer who hadn't argued one of these before, but seemed to know what he was talking about and didn't have the money to pay for WilmerHale rates. I talked to some of the folks on our department management and they thought this was a great opportunity and were willing to let me do it on a pro bono basis. I worked with him. I argued the appeal. We reaffirmed the judgment in a presidential opinion from the Federal Circuit, reaffirming that the analogous art doctrine remained viable. The patent office ended up having to issue updated rules. It was pretty cool. Years later, I talked to Arnold Klein's wife right after he had passed away. She sent me his obituary, and in it there's a whole section about how this was such an important part of his life, having the opportunity to be part of a challenge that really helped individual inventors and to take that all the way to the court of appeals. I thought that was super cool to be part of.

Khurram Naik: What I was so struck with about that approach is that you'd gone to Harvard Law, you had clerked at the Federal Circuit, you were counsel at one of the strongest firms in patent litigation. I think any number of the lawyers in those circumstances, and I know this because these are people I know and talk to regularly, would have just waited for an opportunity. It's something I hear a lot from people of that seniority: oh, well, the partners are the ones who argue things in court, and I haven't had that opportunity yet. I'm so struck with someone of your credentials. You could have just let the work come to you, but you chose to go to the work. That's really remarkable. Where did that drive come from? Have you observed that in others?

Louis Tompros: It may be a little bit of a personality thing, but I definitely have always looked for interesting opportunities. I'm attracted perhaps naturally to new and interesting things. Maybe I get bored too easily. Maybe I don't sort of like the safe path. I feel incredibly lucky and incredibly privileged to have gone to Harvard Law School and to work at a fantastic and very prestigious firm. When things present themselves, when there's an opportunity to go after, I do feel like it's often worth a shot to go after those kinds of things. The drive for me comes a little bit out of always being interested in the next new thing. Always looking for ways to challenge myself and do something different and new. I like to get good at things, and then I very quickly like to find the next interesting thing to get good at.

Louis Tompros: I didn't take the Klein case with an end goal in mind of, oh, I'm going to argue a Federal Circuit appeal and therefore this thing is going to happen. It was really, I think I can do this. As you said, most firms, including mine, it's mostly partners arguing those appeals. There are some good times to try to make opportunities for junior people, but it's rare. So if I wanted to do this, I was going to have to try to find a way to get it myself. It looked interesting, it looked fun, I wanted to do it, and so I did it. It's a little bit of motivation by way of being continually interested in learning and doing new stuff.

Khurram Naik: On that note, I'd also like you to share your adventures in patent prosecution.

Louis Tompros: I am not a patent prosecutor. Hilariously, I am right now in the process of coaching a team of my students in the national patent drafting competition. Every time I meet with them, I have to remind them, I am not a patent prosecutor. This is not what I do. I'm not a member of the patent bar. I've read a lot of patents. I've read a lot of patent prosecution. I teach patent law. But I'm going to give you my advice, but this is not my day job.

Louis Tompros: I did, however, at one point, decide that I wanted to understand it and try it. As I mentioned, I clerked for Judge Linn at the Federal Circuit. I actually went to go clerk after being at the firm for roughly four years. I'd been doing law firm life practice, working very hard, long hours, incredibly interesting work, but at a law firm pace. Then I went to go clerk for Judge Linn. The work was incredibly interesting, but candidly, I went from law firm pace to appellate court pace. It was different. It was slower, more deliberate. We had a lot of time to think about things. As a result, I had probably more free time than I was used to. My wife and I had just had our second child when I was clerking. He was a baby. We were in this tiny little apartment in DC, trying to figure out how to manage him in this tiny little space. We ended up coming up with this weird combination swaddle hook thing, where we could bundle him up and then, frankly, hang him on stuff, mostly on this hook I'd installed on the wall. He would very happily sit there and we'd hang him on the hook. It was probably not the smartest or safest thing to be doing with a baby, but it was interesting.

Louis Tompros: I decided, I've never prosecuted a patent, I wonder if I could do it. We've got this invention of this baby hanging from the wall invention, why don't I give it a shot? In my free time, I wrote up a patent application. I did all the drawings myself using a very old 3D drawing program. I read the parts of the manual of patent examining procedure, the MPEP, that I needed to. I filed the application. It was ultimately unsuccessful. The examiner issued a four-reference combination obviousness rejection, which I still think was wrong. But it would have cost me $500 to appeal it to the board, and I was not going to pay at that point. It was a really interesting experience. Hilariously, many years later, I learned that someone had been writing a book about failed inventions and had searched through patent application publications and had found my invention. There's actually in this book of, it's called something like "Inventions That Could Have Changed the World, But Didn't," a hilarious description of my baby hanger with one of my terrible Google SketchUp drawings. So I guess I've made it to the patent wall of shame. But I'm glad I did it. I learned a bit about what that process is like. You do not want to hire me as a patent prosecutor. But at least I know a little bit about it.

Khurram Naik: I observe this theme of taking manageable risks. These aren't completely outsized risks, these are manageable risks for learning, and not necessarily for some object of gain or definable payoff. I think it'd be interesting to start talking about how you think about risk. There's a distinction or relation between strategy and opportunism. You've had a few reps on this, including Pepe the Frog copyright litigation, which I was struck with. Not just the subject matter as relevance, here's this interesting way that IP plays into some larger conversations, but it was also, even just a handful of years ago, copyright litigation was a small fraction of what it is now, thanks to all the AI disputes. It gave you a foothold in a space that would have been hard to forecast. I'd like to learn more about this. How do you select these projects?

Louis Tompros: I think you're right. If I think about whether I have an overall career strategy, really fundamentally it's one that's opportunistic. I see things that look interesting. Maybe I just have a good instinct for this. But the things I latch onto, when they appear in the periphery of what I'm doing, are things that both look interesting and fun to me, and I can envision a potential upside if it goes well, a longer-term upside. The Pepe the Frog work I did and continue to do for Matt Furie, out of the blue an email came into a listserv of someone who knew this cartoonist's wife, who was interested in figuring out if anybody could do copyright litigation against Alex Jones and the alt-right because they had appropriated his cartoon frog. That seemed interesting. I knew enough about copyright litigation on the periphery of the patent work I'd been doing, and I'd done some other smaller related copyright and trademark cases at the time, that I thought this looks really interesting.

Louis Tompros: I would never say I could have predicted that copyright litigation was going to take off, and technical copyright litigation in the AI space was going to be so important. But I did have the sense that expanding my own practice and expanding our firm's footprint in the copyright space more generally, particularly with something that had the potential of being high profile, such that if it went well it could be valuable. I certainly had an instinct that that was a potential payoff. The main motivation, honestly, was that it was interesting and it seemed like the right thing to do. I represented Matt in a whole series of litigation, most famously the one against Alex Jones and InfoWars for misappropriating his cartoon character, Pepe the Frog. It was a great case. We had a big summary judgment win that then led to the other side ultimately caving and paying Matt everything and stopping this use. There was a movie made about it. I got to go to Sundance, which is something I never thought I would get to do. It positioned me and a lot of the folks at our firm really well when copyright litigation in the technology space really took off. I've had the great fortune of being involved in a lot of that work, where all of the technical competence and litigation skills I'd developed over years of patent litigation, plus the copyright knowledge that really took off, that combining really happened to work incredibly well on this era of AI copyright litigation.

Louis Tompros: If you draw something from it, I do think my primary motivation for taking on new things is because I think they're going to be interesting and worthwhile. But I do keep in mind, is there a potential for, if this goes well, for it to have some greater benefit for me, for my firm, for my colleagues, for society at large? That definitely is there as an additional motivation and filter as I'm looking at opportunities as they present themselves.

Khurram Naik: You could have taken the approach, hey, I have a core competency and expertise, focus on that, laser focus, be the absolute best in the space. What was it about, apart from the raw interest in the topic, was there some other theory you had about the benefit of core wheelhouse plus something slightly adjacent?

Louis Tompros: It's hard for me to say I had a particular instinct that was going to matter. But two things. First, any time you overly box yourself into any particular area, you're missing potential opportunities. I've been part of a world of patent litigation where it was always patent litigation plus some other really important stuff adjacent to it. I dealt with patent and antitrust issues. I dealt with patent and standard-setting issues when that first came up. I'd seen the interesting world of design patents and how that intersects with trade. I'd always been appreciative of the idea that you can't be laser-focused completely, because so many of the cases are going to involve adjacent issues.

Louis Tompros: Second, I have become a firm believer that an understanding of related areas benefits both your core competency and the related areas. I do a mix of patent trial work and patent appeals work. I have colleagues and friends here and at other places that are laser-focused on just one. I'm just a patent trial lawyer or I'm just a patent appellate lawyer. I get it, I understand the focus. But having argued a bunch of patent appeals makes me a better trial lawyer. And having tried cases makes me a better appellate lawyer, because I can see the way the trial plays out and how to brief those issues. From the appellate perspective, I can see the things that are going to matter for trial, where I can cut and where I can focus for purposes of preserving an appellate record.

Louis Tompros: The same is true across different areas of intellectual property. In the past few years I had a very significant case at the Federal Circuit on a complicated patent damages issue. The other side had a very aggressive damages view around the reasonable royalty statute. I could see that the way they were arguing it was fundamentally a disgorgement-of-profits type argument. I had done enough copyright law to know that that fundamentally is a copyright remedy, specifically called out in the statute in the copyright space, and very much not called out in the patent space. I was able to articulate a theory, both at the district court and then as part of the appeal, that what they're seeking is a different kind and nature of remedy, one that is known in this other area of law and called out in a very specific way. But for having done a fair amount of copyright work, it wouldn't have occurred to me to make the argument that way. Becoming laser-focused has advantages, but the danger is it can lead to blinders where you're not seeing something very helpful in an adjacent area.

Khurram Naik: Can you be more specific about the relationship between your trial work and how one helps you get better at the other?

Louis Tompros: Trials are crazy. So many patent trials are compressed, and in many jurisdictions end up being five days on a firm time clock. When I teach my patent trial class, the students have to do it in two days on an even firmer time clock. You're always making decisions on the fly that have consequences. The way I think about trials is that they are fundamentally a simultaneous presentation to three audiences. You're using the same words, the same slides, the same witnesses, the same questions. You're talking at the same time to the judge, the jury, and the court of appeals. That last piece, the court of appeals, can easily get forgotten in the moment. When you're in the fight, if you don't have really good instincts for what you're going to need to make sure gets done to preserve the appellate issues, you will make mistakes at trial. If you don't know what's never going to matter on appeal, you can burn time at trial in a way that's not materially advancing your theme or winning the hearts and minds of the jury, and the judge could care less about, but you don't know that you're never going to appeal that issue. You can end up really mucking up your trial presentation for no reason. So the more experience you have with appeals and appellate strategy, the better choices you can make at trial day to day.

Louis Tompros: One of the biggest pieces of advice I give to junior lawyers is you really have to do your best to at least get in the room to see things all the way from the beginning to the end of a case as soon as you possibly can. It's very hard to write a set of document requests until you have engaged in a meet-and-confer about document requests and understand what the fights are going to be. It's very hard to engage in that meet-and-confer and know what matters until you've used those documents in a deposition. It's very hard to take a deposition until you've seen the deposition used at trial. And it's very hard to make trial strategic decisions until you've gone all the way through a verdict and then seen whether it holds up on appeal. If you can see the through lines, it does make you better at all of the earlier decisions.

Khurram Naik: You said there are three audiences, judge, jury, court of appeals. Is the client a fourth audience?

Louis Tompros: It's funny that you say that. When I do a whole lecture for my trial advocacy class on the three audiences and how to think about them, I always end with a slide that has one of my many favorite New Yorker lawyer cartoons: a person standing up in court saying, "Objection, this makes my client look bad." I point out to them that in the real world there is always the fourth audience of your client. That can be a challenge, especially for a litigator who's crafted a strategy that is going to win everywhere else, and then you realize actually what your client cares most about is keeping this piece of financial information confidential, or what your client cares most about is this aspect and not that aspect. You can win the case and still lose. That's something you have to absolutely keep in mind.

Khurram Naik: You're on the plaintiff's side for your early bets, In re Klein, Pepe the Frog, your patent prosecution adventure. WilmerHale is very much a defense-oriented firm. Can you talk about the relationship between plaintiff and defense work? Another interesting theme from this podcast has been the value of diversification for senior talent. I interviewed Kalpana Srinivasan, co-managing partner of Susman, well known for being outstanding largely on the plaintiffs side. When I asked her what comes next, she said the real adventure now is doing both plaintiff and defense work well. I expect the answer is similar to trial-appeal, but I wonder how you think about it.

Louis's point about plaintiff-defense diversification echoes exactly what Kalpana Srinivasan described as the next frontier for her own career, running the kind of practice that can credibly take either side of the v. and letting that flexibility compound into better judgment. Listen to my conversation with Kalpana Srinivasan.

Louis Tompros: I think you've correctly predicted what I would say. There are advantages to doing both. WilmerHale has the reputation in the patent space of representing a lot of defendants. It's a little more nuanced than that, in that we tend to represent companies that are doing stuff, not practicing entities or universities, companies that are making things, which tend to be defendants in the technology space. In the pharmaceutical space we tend to represent branded pharmaceuticals, which actually do tend to be plaintiffs or declaratory-judgment patent owners. I've probably represented more defendants than plaintiffs over my career. That said, I was laughing because a few years ago I won the Plaintiffs Trailblazer award for a couple of plaintiffs cases I did. I don't think of myself really as a plaintiff-side or defendant-side lawyer.

Louis Tompros: You do have to orient yourself differently. When I'm representing a company that is going to sue a competitor, I often talk with the team about different degrees of focus. Certainly there are things plaintiffs have to do to make a good case that's actually going to stand up. Just like trial and appeals, there's a lot to learn from being on both sides of the v. In front of a jury, the dynamics and the ability to tell a story and paint yourself as the party the jury wants to root for, the good guy, the innovator, the person doing the right thing, plaintiffs lawyers figured that out a bit before defense lawyers did in the patent world. Much like on appeal, having done trials lets you know where the flaws are. Having done cases from the plaintiff's side, I have a better sense of mistakes the plaintiffs can make when I'm representing a defendant, and vice versa.

Louis Tompros: I survey my trial advocacy students every year, because I divide them into plaintiffs and defendants teams. I ask them, all things being equal, would you rather be a plaintiff or a defendant in a patent case? It's fascinating year over year the way that this changes. I've had years where everybody wanted to be the plaintiff, and years where everybody wanted to be the defendant. There are interesting aspects to both. I like doing a mix.

Khurram Naik: How do you think about client selection given different risk profiles for plaintiff versus defense work?

Louis Tompros: It is in part driven by the client's own strategic objectives, and this is where that fourth audience of the client really is the driver. I have represented clients in the patent space who fundamentally would be just fine in a world without patents, and therefore want to vigorously defend patent cases and make clear they're not going to be a cash register for the next person with a weak patent to come after them. Their risk profile is more driven by broader policy. I've also represented clients who have really important patents of their own and are also the target of competitors. I've had competitor-competitor patent cases where I've been on the plaintiff's side for one case in one jurisdiction while at the same time on the defense side for another jurisdiction.

Louis Tompros: The risk profile of different law firms differs. We don't tend to do contingency-style plaintiffs work at WilmerHale. We do certainly have a lot of interesting alternative fees, but we're not in the world of representing class-action plaintiffs or doing big contingency-focused litigation. For us, it's much more about what the client's strategic objectives are. I do not have an MBA. I would be a not-so-great CEO driving strategy of a big public company. I'm very good at taking someone's strategic objectives and then using the tool that I know best, litigation, to try to get what we can out of that to advance those objectives. I'm much more like a football quarterback than a coach or team owner. I know what to do and can give great tactical calls, but I'm largely guided by my client on the broader sets of risk questions.

Khurram Naik: You're an owner of a law firm now. As an owner, do you not set those objectives?

Louis Tompros: I have the great fortune of working at a place where I very much trust the management and they are doing a great job. Law firms are weird. They are a whole bunch of catering operations, where there's a bunch of partners, me included, that have our own interest, our own objectives, and are kind of going our own way. God bless the management team that tries to keep us generally steered in the right direction. Firms can set and do set strategic policies and goals, but firms are just made up of a bunch of people each individually doing their own thing with each individual client relationship, trying our best to row in sync, never perfectly. The firm has its values and a deep commitment to things very important to us as a law firm and as a community. But in terms of what we want for our clients, we want what our clients want, and we're willing to give them the strategic advice and help them figure that out. Law firms are for the most part there to represent the specific interests of the client before them at the specific time.

Khurram Naik: You've talked about business development, and a lot of what's interesting about your work has been opportunism. In developing clients, there's a practice you said you learned from your colleague and mentor, Bill, of gift-giving. I'd love to hear more about that technique and how that evolves into the set of matters you can take on and clients you work with.

Louis Tompros: Bill has been a mentor and a friend of mine for 20-plus years. Very early on, watching him do what he does cultivating relationships and practicing, and then hearing him talk about it and getting advice from him, he fundamentally said that if you do the right thing and do good work and are kind to the people around you, and without reservation do the right thing for them, that's both a really great thing to do in a very positive way to live and practice, and the kind of thing that long-term ends up cultivating relationships that end up being beneficial to you. It is an incredibly long-term play. It was very hard for me at the beginning of my career to hear that, how do you develop a practice? You do good work, you do the right thing, and then you wait a really long time. But I'm here now 20 years later to say that I did, and it has worked quite well.

Louis Tompros: Much of my time, even today, is spent on things that are not yielding any short-term benefit. I am always happy to work with and mentor and teach students. I teach multiple classes. The firm is not making a ton of money on my teaching. It would certainly be better for me to be billed out by the hour rather than meeting with students and chatting with them. But I have seen in others the way that pays off in very long-term ways, where people want your help five, six, seven years down the road. I actually don't do much of what I do for that reason. I do it because I find it interesting and fun, and I wouldn't build those kinds of relationships if it weren't also rewarding in the short term. I really love teaching. I really enjoy a lot of the pro bono work I do. I love the work I get to do with the Equal Justice Coalition to advocate for legal aid. But there is a third piece: it does plant seeds that pay off long term.

Louis's 20-year gift-giving play sounds almost identical to the story Mani Walia told in his episode: a vulnerable lunch with a struggling colleague in 2012 turned into one of the biggest litigation-finance deals of 2023. The intangibles, to use Mani's phrase, eventually become tangibles. Listen to my conversation with Mani Walia.

Louis Tompros: For somebody early in their practice, do good work, but don't be afraid to just chat with the junior person at the client and help them out. If somebody is looking to make a move from one in-house position to another, connect them. If somebody is confused about some area of law, make the connection. If you have an opportunity to go teach a law school class or visit a business school and meet with students, do it. It should be interesting and rewarding short-term, but also really does lay the groundwork long-term. When I talk to my mentees at the firm, it is a hard thing to say: do these things that are not billable, that are taking your time, that are hopefully enjoyable, but not going to get you any short-term reward. But do them because you realistically can trust that many years down the road you really will have a longer-term benefit.

Khurram Naik: Can you share a specific example where you've actually implemented this? Like a financial writing cliche about "buy when there's blood in the streets," some of that blood is yours. There's downside. Can you talk about specific moments when you've done this?

Louis Tompros: I'll tell you one immediate one. We started this discussion with the Klein case. I got a whole bunch of calls after that from paying clients all over the place. None were existing firm clients. They were all smaller but were perfectly happy to have, at that point, a very early-stage partner take over their case. It was not going to be the billion-dollar case, but it was significant. That allowed me to build experience and bring in revenue for the firm, which the firm was very happy about. A huge win-win.

Louis Tompros: A trademark case: I had a client that we had done some appellate work for in the patent space. They had a trademark trial coming up. They said it was very last minute and they didn't have a ton of budget, but could we come in and do the other side of this trademark mock trial? They said, unfortunately, our finance folks have given us just this tiny amount, it was not going to be a loss for the firm, we weren't going to make any money off it. I, as a junior partner, brought a second-year associate in, and we went and played the other side of this mock trial, doing it as a favor to this client. They were super impressed with what we did. A few months later, when the case started to go downhill, they called and said, can you take over the whole thing? We had this whole trial. It was challenging, but had we not been willing to go do this as essentially a low-cost favor to a client we knew and trusted, there's no way we would have been handed this incredibly valuable piece of business. And I would be remiss if I didn't say we pulled it off and won the trial. It was a great win for the client. They were super happy. It turned out to be financially beneficial as well. But it was essentially a week or so of my own time to do the thing I knew was not going to be particularly financially beneficial and had no promise of anything else coming from it.

Khurram Naik: How can you start to attract more of those? How do you become known as someone people come to for those kinds of things?

Louis Tompros: There are two basic avenues I've used. One, anybody can and should use: it's all about relationships. In every piece of work you're doing, every outside activity, any board you're on, any bar committee, any school relationship with former classmates, maintain those relationships. Make sure people understand what you do, can trust you, and can call you. You're willing to pick up the phone or respond to an email and talk with them. Pure human relationship maintenance, including very importantly for folks early in their career, with all the deputy assistant general counsel in charge of X at a client you're interfacing with, maintaining those relationships, checking in, and genuinely caring about what they're doing.

Louis Tompros: The second, that comes with time, is fundamentally reputational. Where I've had successes, I make sure I do what I can to make those successes known. Being willing to talk to clients about the ability to talk to the media about wins you've had, being willing to engage in interviews. I've had a bunch of interviews with tech press and legal press about what AI is going to do to the industry. If you're willing to say yes to those kinds of things, it does increase your broader public profile. The combination of a lot of people knowing you do good work, are trustworthy, and respect you from years of relationships, coupled with a bit of broader publicity, leads to those calls coming in. Then you have to exercise judgment about what you're willing to take on. For most folks, that feels like a good problem to have.

Khurram Naik: How much time in a given week or month are you spending on what you think of as long-term projects?

Louis Tompros: In semesters when I'm teaching, I think of all of that as very much a long-term project. I'm probably over-investing in long-term work because it takes a fair amount of work to prepare and teach a class two days a week every week. When I'm teaching, I probably spend 15 to 20% of my time in a given week dealing with that. When I'm not, it's probably closer to 10% on longer-range things. There are court deadlines, litigation is tricky. When I'm in trial, it's basically zero long-range anything. I'm literally hoping to make it through the next day.

Khurram Naik: You talked about how practices inform each other, trial and appeal, patent and copyright, plaintiff and defense. Let's talk about teaching and practicing.

Louis Tompros: I got into teaching through practice. The first class I taught, and I still teach, is called Patent Trial Advocacy. It came about because the ABA had put into place a rule requiring a certain number of hours of either clinical or simulation work for law school accreditation, and Harvard had a lot of great clinics but didn't really have anything technology or science-focused. They asked whether I could come up with something that would meet this simulation requirement in the patent space. I said, that's kind of what I do as a job, so yeah, I can do that. Every year, my students are most excited about the idea that they're learning from somebody who does this for real. I can bring practical things I've seen and done into that class.

Louis Tompros: About a year and a half ago, I also started teaching doctrinal patent law, substantive patent law. That has been fascinating. I was chatting with Bill Lee, who I've mentioned many times, who's been a mentor forever. I told him I was going to take this on, and he immediately, without missing a beat, said, that's great, maybe you'll learn some patent law. He was in some ways very right, that digging back into this from the student perspective and reading the cases I knew and had used, but from the perspective of, let's go back down to the base level and build back up and make sure I understand doctrinally where this came from so I can help my students, has absolutely influenced my own practice. I argued an appeal in January and there were a whole bunch of moments where I was thinking, oh, this tangential line the judge wants to go down is exactly an area I'd focused on in my class. I was fresh with it in a way, and had thought about it in this broader way.

Louis Tompros: The single thing teaching has done for my own mentality in practice is that to teach something to students who don't know anything, and haven't been at a law firm and been told this is the way you write a discovery request or ask a deposition question, forces me to go back up and understand, oh boy, I better go read Rule 30 again to make sure I understand what the rules for the deposition are, that then dictate why we ask the questions this way. That depth of understanding has really helped me be a bit more creative. There are some things in my practice I've been doing just because I was taught that way and I've been doing it that way for so long. Going back to understand where those things come from gives me a sense of where there's some slack and where I can be a bit more creative.

Khurram Naik: I can understand how powerful it is to dive into the trial history of some substantive issue in patent law. But can you say more about diving into the rules of civil procedure?

Louis Tompros: In depositions, different folks have different practices about whether you say "I object to the form of the question" or "I object, leading," or how much you can get away with. Why? If you go back and read the actual rule, a portion says objections must be stated in a concise and non-argumentative manner. That's the constraint. There may be local rules in place that affect that. If you hadn't gone back and read the rule, now you're in a deposition with somebody and they're doing some BS coaching of their witness. It's one thing to say, stop coaching the witness. It's another to say, Rule 30 makes clear your objections have to be non-argumentative, and the next sentence says I can seek sanctions if you don't.

Louis Tompros: Students always ask me, why don't we depose our own inventor on the plaintiff's side? That's a question nobody would ask in practice because it'd be crazy, nobody does that. But you have to go back and look at Rule 31 and how depositions can be used. Are there circumstances when you actually might want to do that? What limitations can you place on somebody else when they're trying to use their deposition in that way? Why do you ask a leading question in a deposition? The rules of evidence generally apply. The rules of evidence do not prohibit leading questions on cross-examination. This isn't technically cross-examination, but it is an examination of an adverse witness. So you looked at the rule of evidence that allows leading questions for that, and now you understand why. Then when you're doing a redirect, it allows you to do things like object to leading.

Louis Tompros: I have watched many depositions before I took one. I've taken many depositions and have a routine. Teaching forced me to go back and make sure I understood exactly where all of that came from. That gives you more confidence and authority in doing things the way you want to. But it also, where there are differences in practice of folks you've seen do depositions differently, gives you a better feel for why and why that might matter.

Khurram Naik: As you're saying that, I've been using the word "context" for these different paired worlds. But it's as much about testing assumptions. Does that phrase resonate elsewhere in your practice?

Louis Tompros: It does. Most of the cases I've had have involved other large, sophisticated law firms on the other side, lawyers trained in a somewhat similar way. Some of my most interesting experiences have been where the other side is not that, where it's a solo practitioner, or somebody that just isn't normally a patent lawyer. An interesting arbitration where the other side hired their essentially real-estate-and-drug-advocacy lawyer to deal with this copyright arbitration. Seeing folks coming into this that don't have the same background noise and assumptions that the patent practicing world has, watching them do things and object to things I do, and needing to figure out why it is I do it this way, is very much about testing those assumptions. There's value to understanding why we do things the way we do, both for defending them if you need to and for figuring out, do I really need to be doing this?

Louis Tompros: One of my colleagues just had a trial in January and had done something I've never done, which is, on the defendant side, deferred the opening. Under the federal rules you don't have to do an opening statement immediately at the opening of your own case. You can defer until the beginning of the defense case. In the patent space that almost never happens, because usually you would want the jury to hear your side and not just get this one-sided view going into the plaintiff's case. For tactical reasons, we thought about it. It was a very creative idea. One of the big questions was, are you even allowed to do this? Can you do this under the federal rules? Under the local rules? We concluded he could, and it turned out to be a very effective tactic. That's the kind of thing you only think about if you go back and know what the rules are, and aren't operating on background noise of assumptions.

Khurram Naik: Can you talk about the relationship between teaching and persuasion?

Louis Tompros: We're in an era of a great deal of mistrust in authority. Psychological research shows that affects the way jurors and to a degree judges interpret the arguments before them. In the pre-CSI era, you just trusted the witness in front of you, if they seemed like a professor from MIT they must be super smart, I believe them. In the CSI era it became more of a show-me, oh, that's a professor from MIT, and he gave me the forensic file of the source code, therefore I trust him. As general mistrust has prevailed in American society for political and other reasons, we're seeing more jurors having an even greater degree of presumptive hostility and mistrust toward anybody in front of them. If you're a lawyer, you're presumptively lying to the jury. If you're a witness and you work for a company, you're presumptively trying to serve your company's best interest. There has to be a way to cut through that.

Louis Tompros: At least one good avenue is a teaching approach to persuasion. When I have expert witnesses in patent cases, having the correct technical expertise is important, but not anywhere close to sufficient. I'm always looking for excellent communicators and specifically excellent teachers. The computer scientist who has won the undergraduates' favorite teaching award is great, because they get the gist of the issue, but they also can convey it in a way that will make the audience understand as much as they can, but also feel like they are understanding. That is incredibly powerful in engendering trust. Lawyers who try to practice that, who try to also be good teachers in the classroom, or just practice a teaching style of advocacy, can cut past some of the general mistrust. I certainly try in conveying a case to a jury and to a judge to do my best to make them understand, or at minimum make them get that I'm trying to help them understand, because that establishes a degree of trust. You have to be genuine about it. You can't hide the ball from the jury and wave your hands and make them feel like they understand, because jurors will see through it.

Khurram Naik: It's a powerful leveling where you don't have to have a very impressive law firm and all its experience. Someone who is new, a first-chair trial lawyer, this is very powerful what they can use to level the playing field.

Louis Tompros: Absolutely right. Credentials have some value and can get you in the door, and I wouldn't discount that. But in a longer-format event like a trial, or an argument, the presentation itself matters. The focus on being able to convey and teach and build up knowledge with your audience really does make a difference.

Khurram Naik: Can you talk more about juror persuasion, including things that don't work?

Louis Tompros: You first have to put yourself in the position of this decision maker. What are they bringing with them and what are they being asked to do? A juror in a patent case is going to be unfamiliar with the legal system at large. They're coming in, and there's the bench and the flags and the seal and the guy up on the thing with the robe. It's a lot. They're going to be almost always completely unfamiliar with patent law, and patent law is no joke. It is infernally hard. They're incredibly unlikely to have any familiarity with the baseline technology in any patent case. They're coming into an unfamiliar, intimidating situation, feeling like they don't understand what's going on. Pair that with the general sense of mistrust of lawyers. The one thing they know is that lawyers get paid by their clients. Everything you say and everything opposing counsel says is just what you're being paid to say. Now you're asking them to make a decision, either to say the plaintiff deserves a whole bunch of money or to say the defendant is getting off scot-free for something they might have done. That is a big psychological ask.

Louis Tompros: So how do you approach that? Jurors are seeing everything that happens. They're judging the witnesses and the lawyers live. With their general degree of intimidation and presumed lack of understanding of patent law and technology, they're going to feel intimidated by the decision. They're going to feel like they're not qualified to do this. That's very much where the teaching aspect comes in. If you go in and just tell a juror, you have to decide this way, that's not effective. You need to empower them to feel like they understand enough about the legal and technical issues to make the decision, and hopefully your way. That means your experts need to do great teaching. You need to do your own best to, in as simple a way as you can, explain the legal issues, so they get it coming from you and your side, and begin to trust you as a lawyer-teacher. When you go to argue, don't tell them what to do. Show them what they're being asked to decide, show them what supports your position, and invite them to make the move.

Louis Tompros: One more piece. Jurors coming in to an intimidating situation where they don't trust the lawyers, there's literally only one person they can universally trust, and it's the judge. Jurors will be looking to the judge for cues the judge is not supposed to give about bias during the trial. What that means is that it's incumbent upon you to marry the judge. That's an expression I love to use. If you can be in a position where, to the jury, it seems like you and the judge are on one side and the other side is on the other, the judge will do their level best not to show bias, but to the extent you can create the impression that the judge is with you, that's incredibly powerful. You don't want to be making a whole bunch of objections to preserve your record that just get overruled. That makes you look like you're trying to hide something and the judge is with the other side. You want to project calm and confidence. You want to be taking positions where it appears the judge is at absolute worst completely neutral, but preferably irritated at the other side. Calling the other side out on stuff where the judge has to do something in front of the jury is greatly powerful.

Louis Tompros: Ways you can mess this up in patent trials: number one, doing things that antagonize the judge to preserve your record to show you're a fighter, to impress your client. Those tend to fail. Trying to blow things by the jury tends to fail. Attacking first, going after the other side and making it seem like their lawyer is the one lying all the time, is almost certain to fail, because the jury's default is, I don't trust either of you. Attacking too aggressively too early doesn't work. And trying to tell the jury what they must do tends not to work. It's a little bit of emotional intelligence plus an understanding of the psychology of this.

Khurram Naik: For a newly minted partner, somebody who's in the seat now, excited about practicing, how do you cultivate optimism and agency? What are the greatest opportunities you see right now?

Louis Tompros: I tell folks all the time that I think I have one of the most fun jobs in the world, because I've always been curious about how things work. I am basically given unlimited resources to try to understand how something works in the context of a complicated legal scenario, and then I get to teach a judge and a jury all about it. It is the opportunity to learn followed by the opportunity to perform. It's basically my dream job. I'm definitely an optimist and definitely feel like there's always going to be something interesting coming along.

Louis Tompros: One of the cool things about intellectual property law is that it is trying to apply legal structures that are by definition older than the technology happening right now to the technology that is happening right now, and then trying to anticipate the impact on the technology that will happen in the future. The whole point of patent law, it's in the Constitution, is to promote the progress of science and the useful arts. We're trying to take these necessarily antiquated structures and apply them to new technologies. There are a ton of opportunities I see short-term and long-term. It is impossible to talk to anyone anywhere about anything without talking about artificial intelligence right now. Most of the AI litigation is copyright-focused, I've been involved in some of that, and it will be copyright-focused for a bit longer. That is going to shift. There is a ton of artificial intelligence patent work that is really on the horizon. AI tools in court are coming soon and it's going to be really interesting.

Louis Tompros: Patent law and copyright law are federal. We have this weird situation where at any moment you can have courts in California that wildly disagree with courts in Texas, that wildly disagree with courts in Delaware, all having different economic, business, technological, and societal priorities. That's only going to come to the surface more as those priorities diverge. The policy issues always rise to the surface in patent cases. It is the rare patent case that's just about the boring, does this piece of software actually use element three of claim 12. You do that, but at the same time you're talking about how this is going to make driverless cars more efficient, or let us explore deep space.

Louis Tompros: My advice for a newly minted partner or anybody at that stage: making partner at a law firm is a really impressive thing to have done. You have a million opportunities as a result. Another cheesy New Yorker cartoon I always show my students on the last day of class is my absolute favorite: an ant pushing a boulder up a hill, being watched by another ant looking on very skeptically. The caption is, "When it stops being fun, I'll stop doing it." That's my biggest piece of advice for new partners and new law school graduates. There are so many opportunities that come with the privilege of being a partner at a law firm, with the privilege of graduating with a law degree. And there are also an unfortunate number of really unhappy lawyers who feel stuck. You have to unstick yourself.

Louis's builder mindset, going after your own reps and making bounded adjacent bets, tracks exactly what Neel Chatterjee described about testing assumptions and being visible in the market when you're trying to build something new inside or outside a firm. Listen to my conversation with Neel Chatterjee.

Louis Tompros: If you find yourself in a rut, if you don't like what you're doing, please don't keep doing it. Look for the next thing, because there's always going to be a next thing. You do have to take some risks. But you can't just continue in an unhappy place. To be clear, I was not an unhappy newly minted partner. I really liked what I was doing. I just found additional things and was expanding into those. But I do know a lot of unhappy lawyers and unhappy newly minted partners. If at any point it's not fun, you really have to reevaluate and stop. There are too many opportunities and too many great things you can do with this privilege that it would be a real shame to waste it.

Khurram Naik: That sounds like pretty powerful advice, Louis. There's more I could ask, but I know we have to end. Hopefully there'll be a round two.

Louis Tompros: Call me back anytime. This has been really great. It's been really fun to chat with you.

In this conversation, we dig into the recurring theme of this episode: testing assumptions. Neel walks us through using AI as a "lawyer-adjacent" tool to prepare for a California Supreme Court argument, why the creepiness factor is now central to any data-driven case, what he learned about credibility from running mock jury trials with fifth graders, how LFPU came together in a single LinkedIn post, and why he views right now as the best moment in a generation to practice law.

Keep reading below for the full episode and the complete transcript of our conversation.

Top Insights

Below are the highlights of our conversation:

• AI as Lawyer-Adjacent, Not Lawyer-Replacement: Neel used AI to profile how each California Supreme Court justice questions attorneys, and one prompt reshaped his argument: "What is the rule you want us to adopt?" He started his argument that way, framed everything around it, and watched opposing counsel flounder on the same question. AI didn't write the argument. It helped him perform a better version of himself.
• The Puzzle Box Metaphor: Neel tells jurors up front that their real job isn't to become experts in semiconductors or software. It's to assess credibility. His opening and closing show the picture on the box lid. The witnesses are scattered puzzle pieces. That reframe lowers the cognitive burden and aligns with what juries actually do well.
• The Creepiness Factor: In any case touching data, privacy, or modern tech, Neel has learned that the public narrative of surveillance now overwhelms the legal doctrine. Jurors often don't care whether a patent was infringed. They care that a TV is watching them. The winning strategy is to embrace that discomfort and fold it into your narrative, regardless of which side of the v. you're on.
• Fifth Graders Teach Real Trial Lessons: Neel built a mock jury trial program for fifth graders using a real pet-carrier patent case. After listening to 15 cohorts deliberate, he learned that kids (and by extension, juries) reward preparation and punish attorneys who wing it. They also craft credibility stories independent of the substantive law, just like real jurors do.
• Always Look for the Twofer: In a zero-sum game of time, every effort should accomplish more than one objective. Pro bono work that also gives a junior associate their first deposition. Community cleanup that also raises property values and demonstrates leadership. LFPU that simultaneously preserves the rule of law and builds cross-firm relationships. The twofer is the multiplier on a career.

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Full Transcript

Khurram Naik: Neel, welcome back to the podcast. It's been a little more than two years. A lot has changed in law, a lot has changed for you, so it's exciting to have you back here.

Neel Chatterjee: Yeah, thanks, Khurram. It's great to be back. Love your podcast.

Khurram Naik: You were sharing that you used AI in preparing for an argument you gave before the California Supreme Court. I'm interested in what you did there, and more generally, we've been talking about uses of technology in the course of law, technology as a tool to augment what a lawyer does rather than replace. I'm interested in hearing about what you did here in that matter and talking more generally about patterns you've observed in your career and others for embracing technology.

Neel Chatterjee: I'm happy to talk about that. One thing that's happening a lot in the legal industry that people are talking about is how AI will replace lawyer jobs. We'll talk more about that high-level concept in a moment, but I met with a friend of mine who's a former litigator who has now started a legal tech startup called FullProof AI. Her name's Nipun Soorian. Nipun presented to me a concept I hadn't heard about, which was AI can be lawyer-adjacent rather than lawyer-replacement. It was kind of an aha moment for me, that especially when you're doing high-end or complex work where human factors are important, kind of the EQ piece of things, you can actually use AI to help improve your own performance.

Neel Chatterjee: I'll give two examples. The first is the California Supreme Court argument. I had a very significant matter for the Law Foundation of Silicon Valley. I served on the board for 23 years. I'd done pro bono work for them for almost 30. It was a case involving the California Public Records Act, which is similar to the Freedom of Information Act. The die was cast. The briefing was done. We knew generally what our arguments were going to be. But what I didn't really know was how the justices on the court approach argument, and how they approach questioning of attorneys. I went into our internal AI tools and I said, what are the types of questions, not as to a particular subject matter, but what are the types of questions each justice asks? And the response gave me a framework for what is the perspective of each of the judges over a large body of oral arguments that the AI reviewed. I was prepared when a particular judge asked a question for what perspective they were coming from. I could not quite predict the questions they were going to ask, but pretty close, based on this framework of what are the different judges most concerned about in general?

Neel Chatterjee: Probably the most useful thing was the AI said, one justice doesn't always ask this, but frequently asks the question, what is the rule you want us to adopt here? And then we'll use that as a springboard to test the boundaries of that, and different justices will respond by testing the boundaries. It seems obvious, what is the rule you want us to adopt, when you're going to an appellate argument, but it turns out very few people actually argue in that way. It materially changed the way I structured things. I started my argument, and you can listen to it online, saying, the rule we are asking this court to adopt is. And it framed the argument. I could figure out where the different judges were going to ask about the outer boundaries of how that rule could apply. I thought it was a really helpful tool in framing it. My recollection is that the judge asked the other side, what's the rule you want us to adopt, and he floundered around and couldn't really deal with that, and started arguing about the underlying record, which isn't necessarily the best way to deal with an appellate argument.

Neel Chatterjee: Another example I used: I had to give an opening statement in a case last fall, and for a variety of reasons, the preparation was on a very accelerated time frame. Typically when I'm getting ready for trial, I start working up my concepts for an opening about six weeks before trial. It's not like you're working full time, but you're going through an iterative process over time to hone it, get it down to the key issues, get it within the time frames. In this case I only had two and a half weeks. So it was really helpful to use my AI tools to experiment with shortening my opening, prioritizing issues, and helping identify core vulnerabilities. I still developed the theme. I still wrote my opening and created preliminary graphics. But then I used the AI as a tool to figure out where complex concepts may not be accessible, where my graphics weren't quite working. It gave me some assistance, as did the humans on the team, as to where the vulnerabilities were in the way I was presenting things. I was able to take a six-week effort and compress it into about two and a half weeks. I think, just because of the time frame, I probably wasn't quite at the level I would normally want if I had all the time in the world. But it made a hugely helpful contribution on how to improve my own performance.

Neel Chatterjee: The final one I'll talk about: I've had to give some speeches, not legal, not for a client, but more for events. Typically you have a relatively tight time frame. I've used AI to help me find quotes, and then I have to make sure they're not phantom quotes. Sometimes when you have a compressed time frame and you want to convey a lot of concepts, transitions between each concept can be very hard to work out, and it's jarring when you just jump. I used AI to help me figure out strong ways to transition from one point to the next, even though I knew the concepts I wanted to convey. Each of those was lawyer-adjacent. They were performance enhancers, more than replacing anything I would typically do.

Khurram Naik: Let me pick up on what you just said, because it's interesting. In the context of the appellate matter and the opening statement, the conventional thought around appellate argument says there are certain appellate lawyers who are very well known by judges at the Supreme Court, state or federal, repeat players, and they're known for certain things. They have a credibility so that no matter what the argument is, their credibility lends itself to prevailing. Two reactions I have. AI in this context you're describing levels the playing field. What matters less is you mentioned the kinds of EQ, and maybe what we mean by credibility is EQ of knowing how to size up a given justice and how to respond to one of their questions. So that's one interesting aspect. The other is, for yourself, my impression of Neel, a first-chair trial lawyer, is that you've honed a style over time. You've honed a thesis. Last time we talked about some of the principles you use. One core principle in complex technology cases, if it's an IP issue, is to say, we represent the innovator. That's the core of your story. There are techniques you've honed over time. What's interesting is these AI tools aren't wholesale changing who you are, but there are material departures from your process. It's interesting to hear how much AI is essentially changing how people operate at a time when the classic concept of what an experienced trial or appellate lawyer is someone who is known for something. Here you're suggesting AI is a tool for being a little more adaptive and changing more, which seems like a departure from how we practice.

Neel Chatterjee: I'm not sure I would go as quite as far as you're suggesting. I still think there's a huge benefit for people that are specialists in a particular domain and can read the room. One of the reasons I hate Zoom depositions is because you can't read body language. AI can only take you so far on that. AI is going to tell you about the questioning style and things like that. But if the judge is making a face when you're making an argument, it's not going to tell you that. You still have to be able to read the room and know those human factors well enough to be able to read them. There's a place for the specialists with strong capabilities in that area. But you are right at the same time that it does make the playing field a little more level, because it can help us prepare in ways that we couldn't before. Just as an example, in some appellate courts, you don't know which judges you're in front of until the day of the hearing. But you can use AI to keep track of who are all the judges that handled arguments that month to try to isolate who are the most likely candidates to be on your panel. It's enormously helpful when you're preparing. If you're a specialist in those courts, you're going to know all the judges anyway. But these are things that help us improve our performance, and I do think it levels the playing field a little bit.

Khurram Naik: What about this concept of, without AI, you had your intuition about how to approach your arguments, and then AI suggests, you've got this data that you didn't have before, and insights that you didn't have before. You made some changes based on these data tools. You talked about the value of a specialist, but then if you're changing as a result, how do you think about what's the core part of Neel Chatterjee's approach versus what you're willing to change?

Neel Chatterjee: One of the weaknesses of AI is that it always exists to please you, with one exception I can talk about. Generally, if you go to AI and say, what do you think of my argument, what are the weaknesses, it's generally going to tell you you did a great job. It's not necessarily going to push back. Instead, it'll give this diplomatic thing: if you'd like, I can offer suggestions. It's helpful to get those things. I've done a fair number of appellate arguments and jury trials. You do mock juries and you do mock arguments where you get retired judges or whatever to question you. Those are very useful inputs on the way you're structuring your argument. But no single judge or no single mock trial is going to completely change the way you're approaching things. It's going to be more tweaks on the edges, or you might learn in a mock jury trial that people just really hate a particular argument. Each of these are inputs that help you exercise judgment, and I don't view AI as any different than that.

Neel Chatterjee: The example I'll give on a jury exercise: I've done a lot of work involving data rights. People might have noticed that the price of a television has gone down dramatically. You can get, it used to be TVs would cost three or four thousand dollars for the most recent type, and now they're coming out at maybe $1,200 despite inflation. The reason is because your TV is watching you. The way a lot of the TV companies make money is they are delivering served ads to your television through smart functions, and they are monitoring everything you watch. I've handled a lot of patent cases and a lot of other sorts of cases that deal with that issue. One thing I learned from the jury exercises, because I would have a tendency to go on and talk about the legal issues, is, is it infringing a patent, is it not, the name of the game is the claim, all these mantras you learn. What I learned is that people feel creepy about TVs watching you, or about your own computer watching you. That dramatically affects how they feel about anything. They may not care at all about the patent infringement, because they're going to say, I just don't like this technology because it creeps me out. That was a significant learning where I completely changed my approach on data-driven disputes where quasi-privacy rights could be implicated. The creepiness factor has a profound impact on a lot of the tech-driven work we do today.

Khurram Naik: You're saying the creepiness factor probably benefits whoever is on the defense side inside of your office?

Neel Chatterjee: It can hurt the plaintiff too, because if the plaintiff has a patent, the plaintiff can also say, our technology makes sure your data is secure and only used in responsible ways. It may be uncomfortable that this is being done, but it's a reality of our world, but we keep it safe. These defendants, they're not using it in a safe way. They're pirates. They're using your data irresponsibly and without our patent rights, or whatever the rights you're asserting are, you're going to have these irresponsible uses. You're actually embracing the creepiness factor to say it validates your technology. You can do that on both sides. What I've been learning over the past three or four years is that issue, embracing the creepiness of the discomfort around certain new technologies and the public narratives happening, is becoming increasingly important.

Khurram Naik: I want to come back to your idea of using tech to support lawyers and how that's evolved. But since you started talking about how juries react to this, this is becoming a theme on the podcast. I recently interviewed Joe Ahmad of AZA, and something he talked about was framing your arguments to align with the worldview of jurors and the motivations they ascribe. It's not just about honing, there's a level past hopefully you have the facts on your side, hopefully you have the law on your side. There's something past that, which is understanding how juries are going to assign allocation of responsibility and what they think is fair. One example he gave, in his experience, jurors have a hard time believing that corporations don't act with profit as their primary or sole motivation. So they have a hard time understanding other motivations a business might have. They also have a hard time believing that if something important happens, a corporation wouldn't document it. Since you're mentioning that there's not just the nature of the technology but also jurors' reactions to it, I'm curious for you.

Neel's point about juror worldview, the idea that what juries assume about corporate motivation often dominates what they actually deliberate on, echoes what Joe Ahmad described in his episode about preparing trial narratives that meet juries where they already are. Listen to my conversation with Joe Ahmad.

Khurram Naik: I'll also add, Tim Yoo was building on this theme. His theme on approaching juries is being a tour guide. Maybe there are dueling tour guides, and one person is pointing out a bunch of things, and so, you can, you know, the other side told you to look at this tree. Why don't you walk behind the tree? Take a look. Walk behind the tree, look up the tree. Look at the top of the tree. Rather than trying to jam some narrative down their throat, just point out other things they can look at. It's becoming a recurring theme, talking about how jurors respond to ideas. Anything else you want to add?

Neel Chatterjee: There are two things. First, I think there is this bias that everyone buckets every big company the same. All motivations are profit, so it's a negative concept. I've actually tested that issue in certain jurisdictions, and that actually turns out not to be totally true. People will have very strong opinions about particular companies or people. Just as an example, here in the Bay Area, HP has a very storied history, and there was this concept called the HP Way, a very high-ethics, high-values-driven organization, where even when you weren't legally required to do something, you would still do it if it felt like the right thing to do. I thought that died in the 1970s, the 1980s, and then all kinds of things happened with HP, acquisitions, spin-offs. For a variety of reasons, I had occasion to explore how people feel about HP. I wasn't representing HP, I just had occasion to explore it. Even today in the Bay Area, that legacy of how HP behaved gives HP, which is a multi-billion-dollar company that would be subject to all the negative stereotypes, extremely positive feelings about what they did for the Bay Area and the way they approach business. Another company like that is Airbnb. Airbnb's CLO wrote a book called Intentional Integrity about how you lead as a company with integrity. The way they democratized where people can stay and gave people extra access to funds, and the way they monitor and take care of it, overall they had pretty positive feedback. Not all companies are created equal. It's important when you're going into a jurisdiction to understand how people feel about those companies. Sometimes they won't know who they are. You can have multi-billion-dollar companies that nobody's ever heard of.

Neel Chatterjee: The other thing I've learned: I increasingly use this metaphor in cases, because I deal with stuff that's really hard and inaccessible for people to follow. I'll go to jurors and I'll say, my job is kind of like a puzzle box. As a trial lawyer, my opening and my closing are going to show you the cover of the puzzle box. What should the picture look like? What you're going to hear during the trial are all the puzzle pieces in the box that are disassembled, because you're going to hear evidence from witnesses, but it's not going to be in a sequence. It's going to be one witness telling you everything they know, and then the next witness telling you everything they know. You're basically getting this jumble of puzzle pieces. My job is to show you the picture at the beginning, so as you hear the evidence you know where it fits into that larger picture. Then, each side is going to present two totally different pictures of the cover of the box. Your job fundamentally is to assess credibility. It is important you understand the technology or whatever facts we're talking about, but at the end of the day, the reason we have the Seventh Amendment is because there's a belief that people can assess credibility. What's credible, what's not. If someone's shifting around in their chair, can't look you in the eye, people know. Even if they don't understand everything going on, they know whether someone's telling a lie or not, or stretching the truth, taking an aggressive position, or if they're uncomfortable. That EQ is a big part of why our constitutional democracy works. You want to let people know you're going to be talking about technology, you're going to try to educate them, but you want to relieve the stress that causes a little bit, by letting them know their real job is to assess the credibility of the story and see how the puzzle pieces fit together. That's a more evolutionary thought than I used to have. I used to think, I need to be the best teacher of the world for patent cases. The reality is if your expert's testifying for three hours and you're talking about the inner workings of a semiconductor device, you're only going to get so far on teaching a concept.

Khurram Naik: Was there a moment that changed that perspective, framing this as fundamentally about credibility?

Neel Chatterjee: Yes. And it's going to sound ridiculous. A number of years ago, I decided to create a mock jury trial program for fifth graders. Historically, the ABA had something, Goldilocks and the Three Bears, and it's all scripted, and Goldilocks is always convicted, and it's kind of dumb. I wrote one on a patent case. It was a patent case involving a pet carrier for a bike, on an actual litigated patent. We had associates basically present infringement and invalidity of the patents. We'd show things like Toto in the Wizard of Oz, where it's in the little basket in the back and jumps out and runs away from the Wicked Witch of the West. To show that to infringe a patent, you have to hit every element of a claim. We showed a little Lego character hitting a strike, cute things like that.

Neel Chatterjee: We would separate the fifth graders to deliberate, and we'd listen in. While jurors are not fifth graders, they behave very similarly. These kids, first of all, thought putting a pet carrier on a bike is a dumb idea. Not all of them, I've done this now probably 15 times, but they often would think putting a pet carrier on a bike is a dumb idea and is unsafe for children. They would either find non-infringement or invalidity because they thought this is just a bad invention. The second thing was that they tended to focus, without knowing it, on which lawyers were better prepared and which weren't, and which things were more credible to them about the way things were being talked about. We had some mock testimony, and the kids would make those assessments.

Neel Chatterjee: Then, this is the most amazing part. If you and I sit around with a bunch of our peers and someone gives a speech and asks people to ask questions, you're going to have two or three gunners in the front that are going to say everything, and everyone else is going to stay silent. Fifth graders aren't like that. They get into it. They all want to participate. At the end, I said, you are allowed to ask the lawyers anything you want, and you're allowed to give them feedback on what you didn't understand or what you think they could have done better. Oh my goodness, these kids would read the patent. They'd only been reading for four years. They would pull out sentences. They'd call the lawyers out. They would say, you said this thing, and I have the device right here, and here, I pulled on this, and what you said doesn't make sense. They really lodged in their mind a credibility story, and they would either attack or support the lawyers based on it. Every time I've done it, it's so inspiring.

Khurram Naik: Are there any patterns you've noticed in what these students are identifying for what increases or decreases credibility?

Neel Chatterjee: Because we don't present actual live witnesses, how much the lawyers prepare in advance for the arguments is hugely important. The kids don't necessarily know this person didn't prepare as much as the others, but they infer who really took this seriously, who really understands what they're talking about. Because all our PowerPoints are pre-prepared, people can use them whenever they want. Some people go in and wing it, and some people take it really seriously and might even tweak our graphics a little bit. The presentation is flexible enough that you can anticipate what the other side's going to say and say, you might ask yourself that. That all goes to how much the attorneys prepare and how much they are thoughtful about respecting the jury's time. The kids know it. They call it out.

Khurram Naik: Something I've noticed in different domains is if you don't take something seriously, you don't get much out of it. And what I've observed from successful trial lawyers is that they take juries seriously. Not just that they're important, here's this arbitrary and uninformed force I have to account for, but they really treat them as genuine sources of guidance and counsel, with interesting limitations. No one's mistaken about whether jurors are experts in learning some complex technology. I'd be curious to double back to the concept of using technology over time. Is there something that's changed in how you relate to technology and use it, any prescriptions you have?

Neel's point about "tour guide" jury work comes straight from my conversation with Tim Yoo, who treats trial performance like an elite sport and studies what the best advocates do to help factfinders draw their own conclusions. Listen to my episode with Tim Yoo.

Neel Chatterjee: In what I do, because it is so inaccessible to people sometimes, high-powered graphics with imagery that people can remember, persistent themes, experimentation on coming up with them, making sure things aren't too cluttered, that you start with a very simple concept and then build things out of it, use of technology to help figure out those builds and eliminate the noise, is super important. Animations, if you can use animations, can be really helpful. It is absolutely true that a picture is worth a thousand words.

Neel Chatterjee: This is going to sound weird, but for the opening I did, I also asked Harvey, when should I pause for emphasis? When you're giving a speech, sometimes you're saying something big and dramatic, and you need to pause for a reaction from the audience. You do the same thing in trial, when you want people to think about things. It was enormously helpful on where I should pause. In an opening, they'd say, okay, this graphic is great, but it's going to take a little time to process because there's stuff going on, stop talking for a minute, just let it go. I didn't always agree with it, but it forced a discipline on me to think about, how digestible is this, am I rushing too fast, or can I go faster at particular moments? That's something technology has made an enormous help on. Everybody deals with that when you're dealing with openings or arguments on big cases, pacing, how to get people to know when something's particularly important.

Khurram Naik: I want to double back to your fifth-grader example. Something Tim Yoo talked about in the previous episode: he's a big fan of professional wrestling. He would attend regional circuits where there's up-and-coming wrestlers. He'd observe some of the crowd work they would do or moves they would do, and he would explicitly copy those for use in the big tent. Somebody else might view the fifth-grader thing as somewhere between a chore and a game. This was maybe something like a game for you, but it became something a little more serious, where I guess I'd be surprised to learn that you thought heading into this, I'm going to get some really great insights for how to think about the fundamental principle I want to use when I approach jurors. But you gained this very big-picture insight. Treating somewhat play, playing in other domains and learning from there, and then taking that here, is one thing I've noticed. The other is, what I'm noticing you're doing is, you're really testing every premise along the way. You might have a big-picture reaction to, oh, I've noticed jurors view corporations as profit maximizers. But it sounds like when I'm in a jurisdiction, I test that. Some of these things, like the HP thing, aren't some thesis you had going in. There's opportunism involved, but that flows from being methodical about testing assumptions.

Neel Chatterjee: You never accept premises. We come into things with our own biases, but if you're trying a case in the Eastern District of Texas, or in Minnesota, or in Chicago, where I have cases in all those places right now, what informs people is totally different. What their daily experiences are, and how they feel about various things, are in the juror construction. If you try a case in San Jose about a technical issue, you're just going to be greeted with a lot more suspicion as a plaintiff, because there's so much technology everywhere, and you're going to have jurors who have PhDs and senior executives at tech companies, where it's just going to inform how some of the people feel. If you're in Marshall, Texas, or in Orlando, Florida, the life experience is quite different and people come in with different perspectives. Testing is important because you have assumptions that may not be right.

Khurram Naik: Going back to this concept of, jurors are primarily assessing credibility, it seems that's a tool you can wield no matter which side of the v. you're on. If you're on the "wrong" side in a particular jurisdiction, the credibility premise is a leveler.

Neel Chatterjee: It's essential. I'll give a concrete example. About 10 years ago, I tried a case for a company called MobileIron. MobileIron, like on your iPhone today, your company might have apps on your phone that manage your email for work, and if you leave, it can all be wiped out so you can keep your phone but the enterprise stuff is taken out. MobileIron was one of the pioneers in that area. The company on the other side was literally named Good Technology. Every time we had to get up in court and say something, we had to say the other side was Good. When we were doing voir dire, the very first voir dire question I asked was, the plaintiff's name in this case is Good Technology. Can everyone set that name aside to suggest Good may be bad if the evidence shows it? I asked everyone to raise their hand. That informed the whole case, because it said, look, this name is going to work against me, but I want you to think Good may be bad, because it put together this dichotomy. I might have made a joke like, I'm glad my client didn't name themselves Evil Industries Incorporated, because they're not. Socializing those issues as part of the jury activity is really important. How people may feel about a company may be different from what they're being asked to do here.

Khurram Naik: Has this approach of testing premises showed up elsewhere in your practice? The two big changes in Neel's recent life are leadership role in IP litigation at a new law firm, King & Spalding, and you helped launch an impact organization, Law Firm Partners United. Are those products of this testing mindset?

Neel Chatterjee: For Law Firm Partners United, the answer is no. When it comes to management of roles, I think about it a lot in terms of marketing and business development. I have a very unusual style of marketing and business development. Authenticity is a big part of it. There are standard ways that law firms go about doing things, and as the world evolves, that may or may not make sense. Nobody, for 15 years, no law firm had Instagram pages, and very few law firms have a TikTok presence today, but they should. The young lawyers making TikTok videos about legal stuff have bigger followings and are building bigger practices in some ways than the people uncomfortable with the use of those communication leaders. That's all marketing. The premise that writing an op-ed piece in the New York Times is a great thing to do, I don't mean to minimize that. But the premise that that's the way to get the communication out to the people who need to hear it most is simply incorrect today. We're doing a podcast here today. Ten years ago, people weren't doing this. Looking at the underlying foundations of why we've done things the way we have, and is that the way it should be done today, is fundamental to operating a business, going into court, marketing and business development.

Neel Chatterjee: The one thing about Law Firm Partners United, I refer to it as LFPU, that maybe was breaking the mold, was, because I've done so much social-media-related representation over the years, I knew you could create private groups on LinkedIn, and you could use LinkedIn to promote those private groups. That was a very disruptive way to form a gigantic professional association in a very short period of time. The premise was, people in law firms were like, okay, my law firm's got to do what it's got to do, the business has got to decide what's right for the business, but I personally don't agree with that, and I don't feel good about what's going on, but I don't know how to express a point of view about this. I don't know where I go, I don't know how to release the stress. I woke up one morning during March, and I was just pissed off, and went on to LinkedIn, and I'm going to form a group and just see if people want to talk about this. And then it turned into something totally different from that, much bigger and much more impactful.

Khurram Naik: Have there been efforts you've made to organize around something before that weren't successful, using technology or otherwise?

Neel Chatterjee: There are so many, I can't even count. One thing that happens is when you get people around, they get too big to be able to execute. Everyone just wants to get together and complain about things. For years, I founded the Bay Area Diversity Career Fair 25 years ago. It's now called something different because of all the political issues going on. I still don't understand why "diversity" is the word that's offensive. I thought there was a place to have a national organization that ran these in large legal markets all over the country. I've tried for years to get people together to do it, through different organizations, through different law firms, through bar associations, and I've never been able to get the momentum. It's probably among the most frustrating things that have happened in my career. The Bay Area Diversity Career Fair is a pioneer, it's the most successful recruiting program in the country today. Now it's getting dismantled a little bit. It got hundreds and hundreds of people jobs, and people who are partners in law firms now come back because they got their first job through that job fair. Why I haven't been able to do it on a national level escapes me.

Khurram Naik: Do you have a theory for why?

Neel Chatterjee: Not really. People's priorities are in other places around the country. They have other things they want to be their signature events. One of the big issues in some jurisdictions is venue, where do you do it, that's always a challenge. Here in the Bay Area, it became something where if you didn't go, law students would notice, and the quality of candidates was very high. That created pressure on other law firms to participate. Some law firms abandoned OCI entirely. That kind of pressure would not necessarily occur in other markets. In today's world, the reason we haven't been able to marshal something bigger is because of the disastrous approach to recruiting that law schools and law firms are pursuing. They start recruiting for their 2L summer at the beginning of a 1L year. How you even run a job fair in that circumstance, I don't know.

Neel Chatterjee: The thing I'm most worried about is that kind of program is going to have a material effect on particularly first-gen lawyers, which tends to be more lawyers of color. When you're a first-gen lawyer and the first time you're walking into a law firm, it is a scary place. You don't know how the dialogues work. You don't know how to play the game entirely. You have your own background you're still working through as you walk through this. My parent was a bus driver. I've never walked into a white marble office with a bunch of people in sport coats. It takes time to socialize how that process works. I'm spending a lot of time on that issue right now, how we solve that problem.

Khurram Naik: I ask this because you're involved in the Diversity Career Fair, the Silicon Valley Law Foundation, and now LFPU. Someone might see those as, okay, Neel Chatterjee is a hit machine, everything he touches turns to gold. It's helpful if people understand those setbacks. But going back to authenticity, I think that's something you've been known for for a long time. Even before I knew you, I knew of you, because you were very colorful. That's been a signature part of how you show up at work, being authentically you, having a custom business card with a colorful and unusual thing to say about yourself. I'm curious if your concepts around authenticity have evolved, particularly in the past year, since you just made two major changes.

Neel Chatterjee: I don't know if you've had Rudhir Krishtel on your podcast yet. He's a former law firm partner and now does business development counseling and coaches. I love Rudhir like a brother. There's a handful of South Asian Bar Association people that are my brothers and sisters. When the American Lawyer named me Lawyer of the Year, he called me and said, this is the most amazing thing. I said, thanks, I really appreciate it. He said, no, no, no. This isn't an amazing thing because you got it. It's an amazing thing because you got an award because you're you. I still get choked up at that recognition. The founding of LFPU was, if you talk to the people closest to me, they'd say, wouldn't you kind of expect this to be a Neel thing? Neel would just do something kind of crazy and outspoken and super creative, and he's going to see if it's going to work, and it turns into something bigger, but he didn't even know what it was. A lot of people said that to me. At the same time, it was not easy. There were detractors. There were people coming after me. The learning was to stay true to who you are. It was never a hard decision once we had momentum. People like Nisha Verman and Elizabeth Bond and Haley Morrison, Josh Ackerman, Eric Savage, they just became outspoken people through our group to be authentically themselves as well. They were always that way before, but this gave them a platform. Staying true to that and making people feel empowered that they could do these things is such an important message.

Khurram Naik: Did this take issue with any friendships?

Neel Chatterjee: I don't think it impacted friendships. Different people had different perspectives. Some were like, you should be careful, now you could get targeted. They were more acting out of care for me. When things really got big, when we started doing the amicus briefs, when we had 850 members, and I formed a nonprofit, some people were like, Chatterjee's gone off the rails. He's gone nuts. I'd say, I've gone nuts plenty of times before, and I'm going to go nuts plenty of times in the future. I really believe that for people to be successful, they have to stay true to their values. If their values are to be a little quieter and not outspoken, that's okay. Just be who you are.

Khurram Naik: Tell me about how governance worked in LFPU. This was beyond just, here are my opinions, join me. How did you build a governance mechanism here?

Neel Chatterjee: I treated it in two different ways. One, my experience in running large teams on litigation, having a plan with benchmarks because I deal with a lot of TROs, we had to act really quickly. Second, some of the training and guidance and mentorship I've gotten from others on how to lead large groups. I formed LFPU. I needed a co-founder essentially, and Eric Savage at Littler Mendelson agreed to do it. He's such a great guy. Then I went on LFPU and said, look, this organization is about empowering individuals in the way they feel comfortable. If they want to be public, they can be public. If they don't, they toggle a button and no one will know they're a member. If you want to sign your name onto a brief, you can do that. If you don't want to, you don't have to.

Neel Chatterjee: I didn't want LFPU to be a cult of personality. Very early on, when we were getting a lot of press attention, I got a strategic communications firm involved pro bono. I asked people who would like to be spokespeople. We created, like you do for a client, a set of messaging points and core things. A number of people volunteered. We gave our communications firm, here are the people available to talk to media. We formed a nonprofit. I didn't know how to. I went to LFPU and said, is anyone here a nonprofit lawyer? Five nonprofit lawyers said, I'm a nonprofit lawyer. We scheduled a phone call and they all gave us advice. We talked a lot about how big the board should be, how appointments happen, what the formalities are. We have a governing board of about seven people. The only place we thought it was important that people had to be willing to be public was the board, in case there was ever a request for our corporate board minutes.

Neel Chatterjee: Lawyers Committee for Civil Rights in San Francisco gave LFPU an award a couple weeks ago. A bunch of the LFPU members all flew out from around the country. We all had dinner. We all met live for the first time. What we've done is cool, but the fact that people have become very close friends having never met each other before is almost cooler.

Khurram Naik: Apart from the series of executive orders, what is it? Did this fill some pre-existing gap that this just triggered? And what carries this organization forward?

Neel Chatterjee: First, Law Firm Partners United, a lot of people have characterized it as an anti-Trump organization, which is false. It is a nonpartisan organization where we have plenty of people who are Trump supporters, but they just believe in the rule of law. I don't know if there was a feeling of an unmet need on preserving the rule of law prior to the attacks on law firms. But over the last year, we had the executive orders against law firms, we had the prosecution of Marc Zaid, the ABA suing the government, and this most recent thing where the Department of Justice is saying they want to be exempt from ethics rules. Can you imagine, the highest-ranking governmental officials, who are in charge of putting people in jail, want to be exempt from ethics rules? That they don't want public accountability for things they do correctly or incorrectly? It blows the mind how that could not be considered an attack on the rule of law. The EEOC letters where people want to meddle with law firm business on how they decide to do it. Then the government says those things to create a chilling effect to interfere with the businesses, and then they say, well, it actually wasn't a formal request, so they back off to avoid lawsuits that would invariably follow. These are all things that, in varying degrees, Law Firm Partners United cares about. Some people might feel more strongly about one issue or another, but the big issue is people are really offended by the efforts to challenge law firms trying to do what they consider to be the right thing, representing people in what are sometimes unpopular causes, which is fundamental to our system of justice.

Khurram Naik: One thing you said in your last episode, we were recording December 2023, was that post-pandemic has been more of a challenge. People's connections are weaker and I've been struggling with that. I'm curious to what degree you think something like LFPU or other things you've observed are reactions to that. The other conditional point too is increased mobility at law firms. You yourself are a reflection of that. It used to be that partnership was partnership, people tended to almost literally die at a firm. Now with mobility, there's less tie to any one particular institution.

Neel Chatterjee: I don't know if I tie it to the pandemic, but there are places in the market for people to connect on common ground. I would say there were two things that LFPU did that were absent in the market post-pandemic. One, we've forgotten about the concept of hope. People look at large law firms, oh, they're not doing this or that, and there's this monolithic perspective. When people who have some degree of power, whatever that might be, decide to act independently because they think it's important, it gives the people who look up to them a little more hope about their ability to be themselves, to be outspoken critics, to challenge authority or embrace it. Second, in many ways, the most inspiring part of LFPU, as I said, the group is nonpartisan, is that this particular area was one small area where there's an enormous amount of common ground between people. The Article III Coalition, the Preserving Our Republic group, you'll have a really liberal judge and a really conservative judge joining arms on a common purpose. That taught us there is so much room for people to get along in a world where everything you see on the news is people dividing each other. I think post-COVID, there was a lot of us-versus-them going on. There's a screaming need out there to find areas of common ground on nonpartisan bases, and to recognize we aren't doing enough of that.

Khurram Naik: One early reaction I had to these executive orders and the reactions to them, and I know I'm navigating my role where my goal is to talk about evergreen principles and not talk about politics of the moment, is that this potentially increased public awareness of law firms. My impression is that most people don't really have a good sense of how large law firms are, how impactful they are in society, and how they shape rules. Nobody's given much thought to the pathway from practicing at a large law firm to going to the federal bench, the US attorney's office, state AG's office, or Congress. I'm curious if you've observed something in that way.

Neel Chatterjee: I have two reactions. The first, the cynical piece, is that a lot of law firms are going to do what they're going to do to preserve their business, no matter what they're saying publicly at any particular moment. That's not to say what people did recently is right or wrong. As winds shift, people sometimes do what's in their business interest. The non-cynical piece is there are a lot of people who don't understand what the rule of law means. This attack on law firms shined a light on the concept of elites, and how inaccessible the concepts are to lay people. My dad is a sophisticated guy. He's 88. He's not a lawyer. He had all kinds of questions about what I was doing. He had no idea what rule of law meant. As I explained the importance, he was like, I came here in 1963, I know what India was like during partition, I know what India was like, he grew up in a state referred to as the most lawless society in India, and he said, this is really important what you're doing. That really taught me how this concept of what lawyers do is not known well enough to people unless they intersect with the legal community. One thing I've been very passionate about in various groups, not just LFPU, is, how do we build a public education program that has some degree of virality that makes this not an elite concept, but something fundamental to the way we all live. Without a system of rules and laws written by lawyers, there's a higher likelihood you're going to get poison food. How do we know which side of the road to drive down? Some lawyer wrote those things.

Khurram Naik: I'm curious about the concepts of cynicism and optimism. There's that old joke about two communists walking down the street, and one sees a $20 bill on the ground and the other says, no, no, there's no $20, if there was, somebody would have picked it up by now. The notion is, for there to be an efficient market, some people have to treat it as if there are opportunities to make it efficient. I wonder if cynicism and optimism operate the same way.

Neel Chatterjee: My favorite question of this interview, Khurram. If you look up some of the speeches I've given, I conclude by saying, look, it's easy to sit in a room and have everyone wring their hands and leave with their hands wrung, and then go to the next meeting with their hands being wrung. The way to breed optimism in what feels like a cynical society is to just do something. Whatever it is, big or small, just doing something is better than doing nothing. I've done a riff on a Mother Teresa quote, one person creates a ripple, a community creates a wave, and a number of communities can create sea change. Cynicism serves nothing unless you do something about it. There are opportunities for all of us to do it in big and little ways. That's always been my mantra. I'm not a guy who's going to go out to the street and protest and hold up signs and put my fist in the air. I'm going to be like, this thing pisses me off, what is something creative I can do about it? Sometimes I don't even know what it is entirely, and I just do something. It makes me feel better, and it turns out it makes other people feel better too.

Neel Chatterjee: I've been practicing for 30 years. Today is the best moment in our lives to be practicing law. If you talk to people in their 80s now who are lawyers and ask about their proudest achievements, they are not generally going to talk about the multi-billion-dollar cases they won. They're going to talk about going to Alabama and fighting for voting rights, fighting death penalty cases in Mississippi, fighting discrimination or voter rights or access to schools, the difference they made. What they don't say is that they lost a crap load of stuff along the way, but the difference they made had profound impacts on our society. In my 30 years of practice, other than same-sex rights, we've largely been dealing with the fringes of those issues. How do we move the needle one way or another on things like abortion. In today's world, we are at a fundamental point of reset. We are dealing with the fundamental issues that our mentors and the people we looked up to dealt with 40 or 50 years ago. As a practitioner, it's the greatest time in our lives because we can actually play a role in driving that change.

Khurram Naik: I want to go back to acting on something bigger or small. That resonates with me. We bought a duplex in an up-and-coming neighborhood. Litter was a challenge. We started picking up our neighbors' litter too, then the whole block. We just kept doing it. It trained us to be high agency, that we solve problems before we're given permission to do that. And it gives peace of mind, you've done something. What's common to that and what you're talking about is aligning impact with interest. I was interested in the outcome. My property value improves when litter is removed, that benefits me directly. A lot of times when people hear the phrase pro bono, they hear that as zero-sum, either helps someone else or helps me. Part of what you're talking about is things aligned with your interest and skills that help other people and help you.

Neel Chatterjee: Totally agree. I used to give a presentation to diverse law groups called "Open Up Your Can of Maximum Awesomeness." One of the guidelines is, wear sunglasses because they'll make you look cool. But a more substantive one is, always look for the twofer. In a zero-sum game of time, if you're trying to do any particular thing that only accomplishes one objective, you're not maximizing the value you're creating. For a first-through-third-year associate who works with me, I will tell them, if you haven't sat down and taken a deposition or a couple of them in your first three years, I have failed you. The easiest way to get them that experience is through a pro bono case. Not only are they doing something that fulfills and warms their heart, they're also developing skills. You're doing two things at once. They're learning about going into court, developing a relationship with the court as people who did important work for free. You're accomplishing many objectives at the same time. Just like you, you're picking up litter because you don't like it outside your house, but it also has the benefit of increasing your property values. And a third thing, it demonstrates you as a community leader because other people see you do it and might inspire them. Always going for the twofer is really important, because you can't do everything in an isolated category. You don't have time.

Khurram Naik: I think it's helpful to talk about setbacks too. Early in the pandemic, when conferences shut down, I saw law students getting clobbered with lost jobs. I organized an email to about 100 people saying, let me know if you have a job for a law student. That grew into a newsletter of about 2,500 lawyers. But that was very much of the moment. Post-pandemic, participation plummeted. Even from failed experiments, you never lose, because you grew your network. There are relationships you grow. I learned about email communications metrics. There's a ton of skills and relationships you pick up. This podcast is the same thing. A lot of lawyers are afraid of failure. You never fail when you take these measures.

Neel Chatterjee: There's a book we used to read when we're practicing law, and people are starting to teach lawyers about business, called Good to Great. It's a management book that studied really successful long-term companies and what gave them continuing vitality. One of the things they said is, try a lot of things and keep what works. Simple concept. The unspoken part of that is, if you're keeping what works, there's a whole lot of other things that fail. And you're also learning skills along the way. I made my share of failed gambles or things that didn't work out. Every single thing has been a brick in the foundation of building a career. I've told the story before, I won't repeat it here, about how difficult it was for me to get a job out of law school. When you're sending out 882 resumes and you get two job offers, and the firm that hires you says they're closing at the end of the summer, those are failed experiences. Boy, did I spend a lot of money on postage, back then it was letters. You'll learn from that about how to market yourself, how to deal with rejection and failure, how to pick yourself up and move forward.

Khurram Naik: You said earlier this is the best time to be a lawyer. Something I'm struck with is, this is probably the best time to be an IP lawyer. When I graduated in 2013, pretty much all there was to do was patent litigation, and outside of New York or LA, you weren't doing much in copyright. Now a lawyer can join a practice and work on a trade secrets case, a patent case, maybe an AI copyright dispute, trademark. There's been an explosion. What's your thoughts on what's driving that?

Neel Chatterjee: The single largest asset class in the world today is data. People say data is the new oil. It's not about a physical piece of property. It's about defining a new asset class that has enormous value and not having a legal topology around how you look at this from a regulatory point of view, from a monetization point of view, from a housing point of view. Patents don't do a great job protecting data. Copyright kind of does and kind of doesn't. You're seeing all these generative AI cases that are really about use of data, with copyright as a vehicle. Trade secrets does a pretty good job protecting data, but that's a particularized type of use. In the tech sector, the currency of data, how you protect it, exploit it, monetize it, and what are the regulatory risks, 25 or 30 years since the invention of the internet, those things should be worked out. They're completely undefined. Data can be transformed in so many different ways that are unimaginable. It continues to have an undefined legal framework.

Neel Chatterjee: One of the most amazing things, I'll push back on the IP framing, because I don't know if data rights are IP. They're kind of contract, kind of commercial. One of the biggest things in technology today is how to build data centers, harvest the energy, and make sure you're protecting those places properly from calamity. That's construction law and real estate, but it's fundamental to how the economy works. The legal issues around that are just as important and highly contentious as the other things. You build on some pre-existing system and try to do your best to make analogies. Patents are intangible property. The phrase you hear a lot is "metes and bounds" of a claim, well, literally speaking, that applies to a chunk of land. You do your best with some pre-existing set of analogies when you build the next thing. When Jefferson and others were developing the foundation of patent law, they would have had a very difficult time contemplating what patents would get applied to. You have opportunities to develop new architectures around something.

Khurram Naik: Tell me about your move to King & Spalding. We've talked about risks a number of times. Tell me about the risks you assessed with going over to King & Spalding, and my guess is you saw some asymmetric upside-downside there.

Neel Chatterjee: I had a 15-factor spreadsheet when I was looking, scoring the firm, and there were a couple of firms I was talking to. I was thinking about moving on at a time when there was a much bigger test of values going on between law firms. My move in some ways was a very values-driven decision. Another piece was, I really wanted to build something. I like building. When I joined Orrick, we were teeny tiny in litigation. When I joined Goodwin on the West Coast, we were relatively small in litigation. I really wanted to build something and to get back to doing more large-company litigation as well as representing startups, rather than being almost uniquely startups, not entirely but almost uniquely startups, at Goodwin. Those factors weighed heavily on me.

Neel Chatterjee: King & Spalding has an unbelievable litigation practice. In the AmLaw 50, I think we're one of two firms to have over 50% litigation in our firm. I've been told, I haven't confirmed this, that King & Spalding has more members of the American College of Trial Lawyers than any other big law firm in the top 50. Being surrounded by litigators was really nice. I still feel like I'm learning a lot, and having people I can learn from was great. Those were material considerations. King & Spalding has this unbelievable tech client base, but they were relatively small in the Bay Area, and the IP litigation practice, while outstanding, was also relatively small compared to its peers. It was a unique opportunity to come in, build something, but have this unbelievable platform of talent.

Neel Chatterjee: The hardest set of inquiries was, what does it mean to have shared values? Because of what was going on with LFPU and with me personally, the value was really that the firm allows people to be who they are and say what they think. They weren't going to muzzle people. They were going to respect the individuality that people bring to things. I value big tents where you have people of all perspectives. Not everyone does. King & Spalding was much more on that side of the equation than almost any firm I talked to. It impressed me. The drive, the ambition, the trial lawyering, the caliber of litigation that we do was off the charts. I've been lucky to work with some really top litigation practices, not just as a member of the firm but collaborating with them. The people here were just unbelievably talented. I'm embarrassed because I don't feel smart enough to be here every day.

Khurram Naik: Tell me more about this concept of being a builder. That was definitely a theme in the previous episode. You were in the Silicon Valley office of Orrick, strong brand, San Francisco, very well established, Silicon Valley a new outfit. You were a senior associate when you first moved there, which meant there were options to do things as a builder that other people wouldn't. Kalpana Srinivasan, co-managing partner of Susman Godfrey, has an analogous story. She came up to clerk on the Ninth Circuit, discovered Susman, and said, wow, this is completely different than the white-shoe law firm I felt predestined to go to back in DC. She grew that office. It was a Houston-centric firm, very established there, but California was very new. Now she's co-managing partner of one of the top trial firms in the country. You see this pattern again and again in frontier areas. California historically, and Texas now, are frontier territory in big law. Is this asymmetric payoff of taking a salvaged brand and growing it? I think there are any number of other patent litigators, certain practices with really strong, deep benches of patent litigators. A lot of them are curious about doing what you've done, but they don't know how to wrap their heads around it. How do you help someone know whether they want to be a builder? What are the conditions that set people up for success, and what are the internal traits that really make for builders?

Neel Chatterjee: I don't know how many I can isolate. One of the attributes is creativity. You have to be willing to be creative in a lot of different ways. You have to be very outgoing, because when you're building, you almost have to present yourself in the market as bigger than you are. To build a brand, you kind of have to be everywhere at once. Your peer firms, they have 500 people in their offices, and your office or collective offices may have 30. You have to have that drive to show up and be in a lot of different places at once. That's beyond the just practicing law piece. You have to be exceptional at what you do. You have to get some big high-profile wins to build market presence. Being in the market and being active in the market is really important, in creative and differentiated ways.

Neel Chatterjee: A lot of people hesitant to do the building thing, most of what governs them is risk aversion. You have to be willing to take risks. The phrase is, you never hit a ball if you don't take a swing. I've been really lucky in that going to Orrick at the time I did was counterintuitive, and it was enormously successful, not just for me but for Orrick. Taking those swings is something you've got to be comfortable doing. You've got to be comfortable with, if it doesn't work out, what are you going to do? When I started practicing law, I didn't know if I'd make it in big law. I'd never met an Indian lawyer before I became one. I was going to do what I was going to do, and if they didn't like it, I probably would have become a public interest lawyer. I was comfortable with that when I walked in. I made the decision to be unapologetically me. You have to have those attributes, not necessarily be a weirdo like me. Be willing to take the big swings, take risks, bring whatever creativity you can, be good at what you do, and be willing to work to make yourself present in the market.

Neel Chatterjee: The last thing I'll say: the first judge I worked for had this standard for hiring law clerks: surround yourself with people who are interesting to get to know. I've always taken that in my hiring strategy, and even my client development strategy. Some clients, you're like the most painful moment of their life, and they don't dislike you, but you're a reminder of painful moments. It's like, I would never be friends with my cancer doctor. But surrounding yourself with people who are interesting to get to know and have interesting things to say is super helpful and inspiring.

Neel's case for the builder mindset, creativity, visibility, and willingness to take asymmetric career bets, is exactly what Silpa Maruri described building her new trial boutique Elsberg Baker Maruri from day one, with six trials on the docket in the first four months. Listen to my conversation with Silpa Maruri.

Khurram Naik: Thank you so much, Neel. How do we top that?

Neel Chatterjee: We can't top that. All right, bro. I appreciate you having me here. This is really kind of you, Khurram. You're doing good work here. Appreciate you.

Khurram Naik: All right, thanks.

If I walked down the stairs and the train was just leaving, I knew that if I sprinted, I could catch the train at the Monroe stop. It was a point of pride to be able to do it carrying a couple casebooks.

There are two aspects to this that reflect patterns of success I've observed in lawyers.

Being High-Agency

I could have waited for the next train. But being high-agency means looking for opportunities to control your destiny.

Playing a Sport

Catching that train was sport for me. In my head I hoped the crowds would admire me, and maybe one or two people noticed, but in reality the scoreboard was internal.

Two Types

As a podcast host and as a recruiter, I have conversations with some of the highest-credentialed and accomplished lawyers. The reality is that the lawyers who don't show agency, the lawyers who don't have a craftsperson mindset, struggle to advance themselves and find gratification.

When you ask these lawyers to describe their experiences, they point to a list of tasks, rather than outcomes and insights. They say "leadership won't let me" or "I'm not getting these opportunities." They get interviews, but they can't communicate a sense of purpose, and don't advance.

On the other hand, there are lawyers, credentialed or otherwise, who didn't rest on their laurels and wait for the work to come to them. They were entrepreneurial and had a mission. These lawyers are the ones who are still finding joy with all the hard work and drudgery.

Take Control

Here's the thing: high-agency lawyers look for opportunities to shape their own path. They don't wait for permission or point to external obstacles. They find a way to catch the train.

And the lawyers who struggle? They're often waiting at the platform, hoping the next opportunity will just arrive. But it rarely works that way. The ones thriving have a craftsperson mindset and an internal scoreboard driving them forward. If you're looking to make a move, understanding why working with multiple recruiters backfires can help you approach your search with that same intentionality.

Each of us has control this week to shape the next. I hope it's a productive one for you.

In this episode, Tim breaks down how he models his preparation on the habits of elite performers, from golfers to Olympic athletes to professional wrestlers. We dig into the physiology of high-pressure moments, the value of decision trees and pre-committed choices, how to be a reliable narrator for the factfinder, and why the variety of matters you take on compounds into mastery over time.

Keep reading below for the full link to the episode and the full transcript of our conversation.

Top Insights

Below are the highlights of our conversation:

• Prepare Your Physiology: Performance does not start when you say "good morning, Your Honor." Tim explains how he rehearses opening statements weeks in advance, in his living room in front of his family, because managing cortisol and adrenaline is part of meeting the moment.
• Pre-Commit Your Decisions: Tim uses decision trees in his examination outlines so he has already planned his response to every possible witness answer. The goal is to remove reactivity and emotion from high-pressure moments.
• Credibility Is Not Just What, It Is Also How: Factfinders, clients, and opposing counsel all read your conviction, nuance, and authenticity through delivery. Tim argues that how you say something can be just as important as what you say.
• Be a Reliable Narrator: Rather than telling the jury what to think, Tim positions himself as a tour guide who shows them the other side of every piece of evidence and lets them draw their own conclusions.
• Every Experience Compounds: Taking on matters outside his patent litigation core, from real estate disputes to personal injury defense, gives Tim new skills and comfort that feed back into his primary practice. Like The Undertaker collecting moves from regional shows, every repetition serves the eventual main event.

Listen Now

Catch the full episode on your favorite podcast platform.

Spotify

Or click here to listen on Spotify

Apple Podcasts

https://embed.podcasts.apple.com/us/podcast/047-tim-yoo-how-to-study-elite-performers-to-find-an-edge/id1536579571?i=1000751745685

Or click here to listen on Apple Podcasts

Full Transcript

Khurram Naik: Tim, I am very excited to have you back on the podcast. Your podcast was definitely one of the most unusual ones that I've had. And I really love the world view that you're building here, and I'm looking forward to revisiting with some new lessons from the past few years and exploring the top line for you.

Tim Yoo: Well, thanks for having me again, Khurram. I really enjoyed our last discussion. I'm looking forward to part two.

Khurram Naik: Okay, so in our last episode, I really loved the ways you talked about the role of performance. I think the big picture takeaway I took away from that is past a certain point of skill as a litigator or a lawyer generally, it's beyond the substance and the rules and transcends that into there's a dimension of performance, a dimension of persuasion. And that's really where you start to live beyond what does this case say and what's the proper way to get this admission or whatever. So to build on that, I want to pick up on this concept that you recently shared. And it's this concept that performance doesn't start when you say "good morning, Your Honor." Can you tell me about that?

Tim Yoo: Absolutely. So, yeah, when we talk about performance, I'm really not suggesting that we be inauthentic or there's some sort of false, performative aspect of it. I'm really thinking about it in the sense of, let's say, a concert performance, or somewhat topical now, the Olympics are going on. So how are you going to perform in that moment, whether it's a figure skating routine or whether it's a snowboard half pipe performance? Literally, you need to do what's called for in that situation. And how are you preparing yourself for that moment? And the way I think about it is we really need to, especially as trial lawyers, think about what are all the things that go into that moment right before. Like you mentioned, whether it's 9:30 a.m. or 10 a.m., you walk into the courtroom, you're seated at counsel's table and the judge says, "Would you like to address the jury, Mr. Yoo?" I think if you back out the weeks and the months before that, you really have to think about all of the things that you're doing to get ready for that moment. At least in my opinion, I think that's important.

So the way I look at it is, the first thing I think about is how am I going to feel in that moment? What are the things that are going to be, as a human being physiologically, what are you going to be feeling? There's going to be certain levels of cortisol, there's going to be adrenaline, there's going to be a lot of things just coursing through your body in that moment. So I think it's important to think about those as well. So when I say the performance doesn't just start right at go, it starts before that, I'm thinking about, have I done the adequate preparation in terms of obviously the substance of what you're going to say and the evidence that you've prepared and are ready to present. Those are obvious. These are things that you've already done presumably. But I'm leaning more towards, have you really thought about how are you going to say things, in what order? Where are you going to put the inflections? How is that going to come across?

So I think a lot of that comes from, obviously for me, my process begins a few weeks out or a few months out. But more practically speaking, probably a few weeks out when I know exactly, let's say, when opening statement is going to occur. And I'll back out two weeks, and I will, in my living room, have my wife, probably my oldest child there sitting on the couch watching me go through this process. At first, it starts out as a riff of my opening statement, and then it'll get refined further and further as I approach the trial date. But for me, that's an important part of my process, because I know that I want to be able to, at the very beginning, have an idea directionally where I'm headed with the things I want to say, and how I want to say them, and how I want to order them. And that just helps me towards the trial date, having a set process of what I know I'm going to be doing every night in the lead up to that trial.

Khurram Naik: Yeah, I think that's valuable, because the thing a lot of lawyers are thinking about, they're thinking about, okay, what evidence needs to get in, at trial. But I think, let's say in a recruiting context, I find any number of times lawyers say, "Oh, I'll just negotiate with this firm." I say, okay, what are you going to do? What exactly are you going to say? When are you going to say it? How are you going to frame it? I think there are any number of times lawyers think, okay, well, I'll just approach a friend to go to the firm. Okay, and so thank you. At the end game where you will accept only one offer and decline all others, what's it going to feel like to decline that offer to someone that you know? Like, how is that going to feel? So there's definitely an emotional dimension, and then a tactical dimension to these moments that people aren't necessarily thinking through. So what do you attribute that to? Why aren't people thinking about the emotions they're going to be feeling in a moment and working back to that?

Tim Yoo: Yeah, that's a good question, because I mean, I think to your point, the more foresight that you put into something, the more that you plan out, "Hey, I'm going to have this type of physiological response," or "I'm going to feel this way," and then you sort of try to almost take that aspect out of it, I think you're better served. Because you're right. You don't want to, especially in our profession, be prone to rash, emotional, reactive decisions. You want to be able to apply proactivity to those. And I think the only way you do that is you sort of game it out. You have a decision tree. I mean, even in my examination outlines, there are always trees in terms of the witness responds this way, the witness responds that way. Have you even contemplated how are you going to respond in that moment? So I think the more, I guess it dovetails to what I just said about the preparation and planning for things to go sideways, the more you're able to apply your objectives in those scenarios.

But I think what you said is interesting, because I think people underaccount for that in terms of how the emotion in the moment, when you're feeling a certain way, when you're in this parasympathetic state, this fight or flight emotion, how you might respond then. So I think that's really the core principle of what I'm talking about now. Try to essentially work that out of your process. Work out the emotion and those feelings that you'll have, and try to be as systematic as possible.

So even something like an opening statement, I think the genesis of it was, I was watching a golf pro talking about how they hit certain iron shots, and they said, "Well, on the practice range, I might hit that shot 160 yards, but in tournament conditions, I have to discount it by five yards, because it's going to be a tournament. I'm going to be more tense naturally. So I'm only going to be able to hit it 155 yards." And I thought that was really interesting, because it's this acknowledgement that even as an elite pro athlete, an elite performer, they're acknowledging that they're going to feel a certain way in certain moments, and they're not ignoring that. They're not discounting that. They're sort of leaning into it and saying, I need to take advantage of what the situation is going to be at the time, and I'm going to have to have a plan for that going in. So I think that's what I'm talking about.

Khurram Naik: And so your reference earlier, the concept of credibility, the components are what you say and how you say it, those are two aspects. So do different situations call for different techniques? Is there some overarching principle that you are using? Is it something like, "Well, I'm a big believer in the decision-maker's agency, whether it's the factfinder or the judge, that I'm always exercising. I'm always showing them how to exercise that agency, and leaving room for that." Or, what are the principles or techniques you're using for what you say and for how you say it?

Tim Yoo: I think they're somewhat related, but I think they are distinct. I think that how you say something is what we're talking about now, in a sense, because I'm assuming that what you say in terms of the substance of what you put together, the strength of your arguments, the best evidence that you put forth, that's the "what you say" part of it. I think the "how you say it" is almost, if not more, important in some situations, because the factfinder, whether that's the judge or the jury or your client or opposing counsel, your co-counsel, your teams, are looking into how you say certain things, how much conviction you're conveying, what lack of conviction you're conveying, what nuance you're conveying. And I think that all goes toward credibility and authenticity, which are the key pillars of what we do.

So what I'm talking about is, and I think it's the reason why I find it so important to put in all those repetitions in front of the mirror, so to speak, or in my living room, in front of my wife and my kids, is I really like to study how it's coming out, how the transitions are working, what are the high points emotionally or the points that I find myself emphasizing more naturally. I think those are interesting and I like to study that. So I think that's where I find the value and the benefit in going through this process, really focusing on this notion of how you say things, when you say them, could be almost as important as what you say.

Tim's focus on credibility through delivery reminds me of my conversation with Joe Ahmad, who talked about why juries are the ultimate "phony detectors" and how sincerity beats polish every time. Listen to my episode with Joe Ahmad here.

Khurram Naik: Can you track, I think there are a couple of recent matters that are particularly interesting. I mean, you're patent by training, an IP litigator, but you've had some very interesting other kinds of matters you've taken on. One of them was a real estate dispute involving defects among other issues, and then another one was a personal injury defense matter. So really a novel matter to take on for someone with your work experience. So in the context of, say, opening arguments or other positions that you took or presented, how did those change? What is it that you iterated, can you give us a sense of the before and after?

Tim Yoo: Sure, I think in those kinds of situations, you have to be mindful of the dynamics, like people coming in with certain notions. So for me, in those particular two matters, it was almost, I don't want to discount the merits, but I wanted to emphasize also the vibes as well. Arguing vibes in a sense of, this is something that, whatever grievances you have, my client is either trying to do the right thing, this is not something that's deliberate or intentional. And you want to make sure that gets across. At the same time, you want to make sure that no one's trying to skirt responsibility or hide behind what happened. You want to convey that this is something that we're here to confront, we're here to let you as a jury decide what happened.

And trying to be, the way I view my role is to be a reliable tour guide or a reliable narrator, in a sense, to show them different pieces of evidence. The way I analogize it is, if we're going out and opposing counsel is a tour guide saying, "Hey, look at this rock, and look at that tree, look at that stream," my role is really just to be the counterpoint of that, to say, "Hey, look at the other side of that tree, why don't you pick up the rock and look at the bottom of it, and see what you see there, and draw your own conclusions from that." And I'll even tell the jury this, that, look, I'm here to essentially play my role in the process, because if we don't all play our role, whether it's the counsel involved, the judges, or the juries, then the system's not going to work the way it's supposed to work. And if it doesn't work the way it's supposed to work, then we've all lost something. So please view my role as just being the person to demonstrate that there's always a different side of every story.

Khurram Naik: You referred to, I think it was the previous episode or so, in tennis, that you've got these elite tennis athletes, and they really view these rivalries. I'm not very up to date on tennis, so for me it was like Agassi and McEnroe. These rivalries where the opponents got better results. And so you've talked before about this concept of viewing opposing counsel not as some block to some outcome, but how can we play off each other, work each other up. When you talk about this concept of roles, it's really fascinating about showing people the different roles that everyone plays. And it's particularly relevant to me because as a recruiter, lawyers historically have been in this position. Anyone who's perceived to be a middleman can be in the position of trying to explain why they're even there to orbit outcomes. And so there's definitely a dimension of explaining the role to people. Say, here's what the role is, here's what this is called. By aiding the system, here's what the payoff is for everyone involved. Have you found, let's say with opposing counsel, so you were describing this role, explaining the role that everyone has, have you found that opposing counsel has, that's resonating with them, they've built on that, built a system of more effective way of getting to resolution? Like what's your experience for how opposing counsel has responded to this structure that you're proposing?

Tim Yoo: Pleasantly, I've been pleasantly surprised, maybe not surprised, but I would say more often than not, I think people accept that. We are all part of this inherently adversarial process, but I think that's by design. That's not a bug, it's a feature of the process. The process was set up that way on purpose so that we can all arrive at what the truth is. I think that if you view it from that construct and then speak and interact with opposing counsel within that framework, I've been pleasantly surprised at the response where people are willing to engage in that way. Obviously, there are folks who might be outliers, who might view it even more personally. Again, I've never viewed it personally. I've viewed it as you're trying to be a zealous advocate for the client that you represent and the other side is the same way.

So in a sense, they're your foil or your dance partner in what's going to happen. I think that's been a much more productive way for everyone involved, to have that level of being collaborative. The way I analogize it is, look, just like a tennis match, just like Agassi and McEnroe. Those guys, once they were in between the lines, they're trying to beat each other's brains out within the context of the contest and the defined rules. And within those rules, they're doing that because that's part of what they're supposed to do. The public expects nothing less, the paying customer deserves nothing less than that. So I think that's a good way of thinking about it. But at the end of the day, you're always shaking hands with your opponent at the net. And that's how I view it as well. At the end of this contest or interaction, at some point, we're going to look at each other and shake hands and say, "Well done." And I think that's a productive way to look at it.

Khurram Naik: So I want to pick up on this idea of role. I want to go back to the refinements you made in your opening argument. To get a sense of, I think for any of these principles, it helps to understand what the principle stands for and what it does. So going back to the opening statement, the evolution you made there, can you describe the initial approach you took at some level of abstraction and then the final position, what changed and why? Because that would help us wrap our heads around how you're honing in on what's most persuasive, how you're saying something.

Tim Yoo: Yeah, I think when you start out, you have this notion that, and perhaps it should be true, that if you have the goods, that's really all that matters. And by goods, I mean whether you have the evidence on your side or the law on your side, hopefully both. And then you can just kind of get up and rely on whether you think it's your natural charisma or your natural public speaking ability or your natural innate ability to persuade people and get up and do that. And maybe some people can, but I find that to be an outlier. Because I think in order to order the argument or the statement to be as persuasive as possible, you really have to start thinking about the structure of those.

So I think when you start out, I had this notion that people might be naturally great and charismatic speakers and they're going to naturally give great closing arguments or opening statements, or people might be these naturally brilliant examiners and be able to cross examine someone at trial and just be able to do that naturally. I find that empirically not to be the case in the sense that I believe that taking a great examination, giving a great opening statement, is fully and directly proportionate to the level of preparation that goes into it. So I think that's really what sparked it.

And to more directly address your question, for me, it was really, my approach to when I would take depositions is I had an idea of where I wanted to go in certain topics and not be so granular. But then I realized that the more time that you spend mechanically setting things up, working on your outlines, working on the contingencies, working on parts of your outline that you'll never even use, that is directly correlated to the quality of the examination. So I think that's really why I started thinking about it this way.

Khurram Naik: Is it, do you find, is it the quality of the examination improves, or is it more your comfort level, and then that kind of goes back to vibes again? Where it's just like, "Hey, I'm so comfortable and my adrenaline response is lower because I have these contingency maps." Is it about preparing for the contingencies, as far as knowing what to say, or is it more just the comfort level of knowing that you've done the work?

Tim Yoo: I think it's both. I think it's really both of those things. I think the comfort level plays into it a lot because, at least for me, I've been at trials where I'm seeing opposing counsel, very experienced counsel, and maybe it's natural, but they're pacing back and forth. They're putting their hands in their pockets, just these natural ticks of being nervous and having anxiety. And I'm not saying I don't feel that. I'm a person. So of course I feel that. But I think to be able to lean into that feeling, I think for me personally, I feel way less nervous and way less anxiety the more work I put in. So if I walk in knowing that I've done everything I can possibly do to meet that moment, then I think the nerves go away in the sense that you have that level of comfort.

But I think it's also having those repetitions and being able to have that level of comfort where the playing field slows down, so to speak. Athletes talk about being in this flow state where the pin in golf looks like a huge bucket. The other side of the tennis court, you can't possibly miss it because you're just in this flow state. So I think the more repetition you have and the more that you condition yourself to be in that situation, I think you start feeling that. And I think also it is just a unique thing about the law, that it's both theoretical and practical in the sense that it's one thing to know all the theory and know all the right things to emphasize and know in a sense what you're supposed to do in a situation. That has to be married with having been in that situation multiple times, I think, to really feel like you've begun to master a certain area. And to be clear, I think I'm far from that. But the more repetitions and the more times that you have opportunities and different experiences, it compounds. The more comfort you get, the more experience you get, the more effective these things become. It begets more comfort and hopefully more effectiveness as you go on.

Khurram Naik: So I want to ask you some more about that, because I think you're talking about this concept of flow. What it makes me think about is what I'm sensing you find so gratifying about elite performers and athletes, this aspect of flow, where they're just so connected with what they're doing. And I think that's important because the practice of law is really unusual compared to other disciplines in that, let's say in sales, my wife sold software, and in software, if you're just good at what you do, you can be the equivalent of, you've got people who are in business development roles, that's the entry level role, then you've got people who are account executives, those are client-facing, generating revenue. And you can just move into an account executive role and functionally speaking that's more like a partner than an associate. You can become a partner effectively in that world in a couple years if you're just really good at what you do. There's nothing like that in law. Even if you clerked at the Supreme Court or whatever, you don't just, "Hey, great, we're going to make you a partner and you'll argue at the Supreme Court three months from now." It's just a really long haul in every part of the profession, no matter what your credentials are. And I wonder, with so many lawyers, what they hunger for is that level of gratification from their work. And for litigators, so few of them are going to try a case. My first trial I went to, one of the partners said, "Hey, if you don't enjoy this experience, you should really think about moving into another practice area, because this is what it's all about." For me, I just really enjoyed it. It's definitely something that I knew I wanted more of. But there's that gratification that we're looking for from work, because it's a long haul, hard hours for years, where it's so rare to get into a flow state. And I wonder, did you see the documentary, Jiro Dreams of Sushi?

Tim Yoo: I did. I love that documentary. And I think it's sort of what you're talking about where someone had to train for 10 years just how to roll the rice just right. That took 10 years of apprenticeship to get to that level. And then you have to graduate to different levels of mastery.

Khurram Naik: So I guess the two ways to look at that are, one is that's deranged, because obviously the fun part would be to be Jiro there with the customers, presenting, making adjustment calls for what goes into a piece of sushi, presenting to the customer, courting the customer. "Here's, I'm guiding you in what this experience is. This isn't just a sensory experience. This is also, you need some context to understand what's special about this." So that seems to be like the trial lawyer in the courtroom. And that's the ultimate aspiration. So it seems like, hey, that profession's the same thing. You got to put in decades of work to really get to the privileged position of doing that. And Jiro has his sons who are in an apprenticeship, studying with him. They're grown men themselves with children, I think in their 40s, 50s, kind of waiting for their turn to be like their father. And so I wonder, how, for people who are not in the courtroom yet, how can people find that flow in what is otherwise the drudgery of sifting the rice, the other kinds of tasks that seem menial in the kitchen? How can people find that flow earlier in their career?

Tim Yoo: You bring up a great issue. I think just backing up, I'll address that point. But I think backing up, what you said about it being tough, I think our profession is tough because it does take time to achieve a certain level of competence. Some core competence. It just takes time and doing it over and over. So I think that's a difficult aspect of it. Because I agree with you that for anyone, and I think I read an article in HBR, Harvard Business Review, where a couple of the key components to someone feeling a level of job satisfaction, one of them is the job has to align with your values in some sense. But another key component was that you have to feel as if you're good at your job. That's a big part of feeling contentment. And I think the hard part of our job as lawyers is that it takes time to do that. Like I said a moment ago, it takes a lot of repetition to get to a certain level of mastery before you start feeling as if you're good at it. And when you start off, like you said, you're doing a lot of work that seems to be drudgery.

I certainly, speaking for myself, spent weeks or months of my life doing things that I can probably do in a couple of minutes now. And it just takes time to really get to a point where you then have this basic idea that you have an aptitude for what you're doing. So I think that's inherent in our job. I don't know if I have an elegant solution to that because I can't sit here and say there's some magic elixir or some potion to instantly jump to the front of the line and just have this level of mastery a couple of years out of law school. I think that's just an aspect of what we do.

To address your question about how you can, while you're figuratively figuring out how to roll the rice or massage the squid a certain way to make sure that it's palatable, and I hope this is not a cop-out answer, but I think it's realizing that that in itself is part of the process. A lot of what you do, and again, speaking for myself personally in my first few years of practice, was really just to learn how to be a professional, period. Not even just a good lawyer, but just not be a knucklehead. To be a professional worker who's going to an office every day, showing up on time, getting assignments done, and just trying to go into that process and learning how to talk to people, how to meet expectations, whatever the assignment is, to do that to a T. Because then once you sort of figure that out, you get the next assignment, you get the next level of skills that you're asked to pursue.

I think it's having the attitude that it's all leading to something else. Speaking for myself, I'm almost 20 years into practice and I still feel like I have to figure out what I want to do when I grow up. I still feel like I haven't quite become a grown-up in a sense of, I'm looking at the next thing to master or the next thing to tackle or try to get a hang of. And I think maybe all of that, if you want to collapse it down to a single concept, is to have this growth mindset of what is this task going to be in service of. How am I going to get better at what I do by doing this thing.

This idea of compounding growth through deliberate practice across your career resonates strongly with what Rakesh Kilaru shared about the long game of building a trial practice. Listen to my episode with Rakesh Kilaru here.

And not to tie everything back into sports, but everything, anyone who's ever had more than one conversation with me knows that's what I want to do. But this past weekend, I observed one of the more compelling sports comeback stories I've ever seen. This golfer, pro golfer Anthony Kim, he took 12 years off the game because he had certain injuries, some addictions, personal demons that he's openly spoken about. He got back on the tour, the LIV Tour, a couple years ago, and his results have been very poor. He would finish last place or second to last place in the first few events back. But I would follow him on social media and he would always be out on the course, grinding, training. His whole mantra was, "I just want to get one percent better. I just want to get one percent better today than I was yesterday." Because he knew that was going to compound over time.

At the end of last year, he was actually relegated off the tour because his results weren't there. So he was kicked off. He had to qualify again through an open competition. They had a competition saying the people who finish in the top three of this tournament at the beginning of the year will qualify to play in our league this year. So he had to do that. He finished third by the skin of his teeth to get on. And his results have gotten a little bit better. I saw an interview with him last week where he said, "Look, it's somewhat frustrating because I know all the work I'm putting in and I know I'm better than that. But it can be discouraging because you're not necessarily seeing all the results manifest on the field right away. But I know the work that I'm putting in and I'm getting better."

And this past weekend, he won the event at LIV Adelaide, which is the biggest tournament that they have. And he beat two former major champions, a former number one player in the world. He was down by five shots going into the last round, chased them down, and won this event. And it was very inspiring for me and really resonated with me because I think his whole principle of "I just want to put in the work and get one percent better," even though you're not seeing it manifest in a tournament in terms of the results quite yet, you know that he's banked that time. He's banked those experiences. And at some point, it was going to pay off.

And what was really captivating to me is when they were talking to him at the pressers afterwards, it wasn't so much like, "Hey, I can't believe this happened. Oh my goodness. I never would have conceived of this." He really was just sort of, "I knew this was going to happen. I knew that this was going to happen. The wild part to me is that it happened today." So it seems a little bit odd that he was so far behind going into today. But, "I knew that I put in the work and I believe in myself. So I knew that this was going to happen." And it was really inspiring.

Khurram Naik: I think what's so interesting about your approach, you know, in our first episode, I kind of commented on, if you just look at your training, you're this Caltech math major. And so there's a level of raw rational analytical power that comes with that. And any number of patent litigators, the stereotype is that that's what their expertise is, being technical people and not really focused on things like storytelling. And I've heard federal judges comment on this. Like, "Hey, it's just a patent trial and I kind of need a little more in the way of storytelling, and just getting out of the weeds of these endlessly boring expert battles that no one can make heads or tails of." So I think you really completely inverted that. I wouldn't guess that you were this Caltech math guy. So that itself, I think I commented in the previous episode, is remarkable, that you've transcended that training.

But I think another really interesting tension for you is this structure versus vibes and the reciprocal nature of those two. Because it's kind of like that quote from, I think it was Flaubert. Being structured and regimented in your life, ferocious in your art, or something. And having this highly regimented approach, Stephen King's On Writing advocates the same thing. My big takeaway from reading his book is, he takes a hostile view to this idea that there's some muse, this idea that inspiration was literally a god that would just visit you. Stephen King's position is there's not some magical fairytale creature going to inspire your art. It's from showing up and doing the hard work every day. Just grinding every single day. That's what works for him. That's what he advocates for. And so it's interesting because I'm sensing this interesting reciprocal nature between the goal, which is to get to this emotionally transcendent flow state, and how you get there is by having a heavily structured process. How do you think about the relationship between these two?

Tim Yoo: I think you just hit the nail on the head right there. So when I say vibes, I do mean that. I don't mean to suggest that it's in some kind of haphazard way and it's going to be, in a way, however I feel at that moment, I'm just going to try to convey. I think when I try to convey a vibe, it takes a lot of work to get to that point. And like you said, there has to be some kind of infrastructure behind it, some kind of very strict organization, structure, preparation. All those things lead to being able to convey a vibe.

And just as an example, at a recent trial I had, we parachuted into the trial a couple of weeks before. A lot of the liability issues had already been stipulated to. So there weren't a lot of exhibits or evidence that was going to be at issue. I think my opening statement was maybe 20 minutes. But in terms of the preparation that went into that, you would maybe not have guessed that based on how short it was, in a sense. I like to joke that I had to argue vibes because I wasn't exactly sure what evidence was going to come in. I mean, I joke about that. But I think you've got to create a structure that allows you to get to these emotional inflection points and really emphasize certain aspects to a jury. And in a lot of ways, it's a lot harder when you don't have these tent poles of, "Hey, look at the contract, look at section three of the contract where the other side agreed to this," and you can really just pound on that. I think it takes discipline and effort and thought to really think about what are the high points or the low points that you want to emphasize or even dwell on during your statement. So like you said, you hit the nail on the head in terms of it's not just going out there and winging it. There really has to be some kind of structure behind that, even when you're arguing a certain vibe or you want to imbue a certain emotional response in your audience.

Khurram Naik: Can you tell me about how, you know, you've done so much by way of patent litigation by training. And one thing I find really interesting is these departures from it, just because you can. You're just taking on completely different other kinds of work, because you can. How does that connect to this concept? Because I could, from first principles, say, "Well, Tim, shouldn't you be focusing on patent cases of a certain kind? Maybe it's just your niche into, say, Frand disputes or whatever, and that's the one space you're showing up in." And then that way all that foundation's there. Because the architecture of a patent case, actually a great example is Hatch-Wax litigation. It's so regimented that there's local Hatch-Wax rules that govern the schedule. There's minimal motion practice. And so that would be a space, if one wanted to try a lot of cases, that would be a space to practice again and again, so you can hone in on, like you're saying, that flow, the tennis court becomes a football field, whatever. So what role does the variety of work you're taking on play in this pursuit?

Tim Yoo: To address your question of how pursuing these varied experiences is going to service my pursuit of mastery in patent litigation, my short answer is I view it as all in service of that. I allow myself to be open to these opportunities because at the end of the day I'm tying it back to how it's going to serve me down the road. So when I take on these other types of trials, it's not solely because those trials are interesting and they're challenging and they're worthwhile in their own right. But an aspect of that is also, how am I going to gain experience which is valuable, gain skills that I'm thereby going to be able to leverage later.

I had a recent arbitration where one of my teammates was also a patent litigator by trade. And I was telling him, look, these skills that you're picking up now, think about it in terms of when you're going to use it next on your next big patent trial. In terms of your ability to craft an examination, to tell stories, to tell all different types of stories, to have that level of comfort when you're before an arbitrator or a jury. I think those are things that me and him or anyone on our team are going to be able to bank and deploy later on. So I don't view those pathways as separate. I view it as part of a linear journey of, these are the repetitions or the experiences that you're allowing yourself to have now, because at some point in the future you're going to be able to use those.

And I guess to draw back full circle, I spoke a lot about The Undertaker in our first session. But I was listening to him talk and they were asking him about the evolution of his character and his moveset. And a lot of what he said was similar to what we're talking about now. He said, "Look, that move where I walk on the tight rope, I saw someone when I was training in Mid-South territory do that, and I made a mental note to myself that I'm going to steal that." And then he got to a different territory. He got to Florida, he saw someone do an inverted piledriver, which became his signature move. And he said, "Okay, I'm going to make a mental note, I'm going to steal that." And the point is, along the way, along this journey, when he wasn't in the main event of WrestleMania, he was performing in front of 50 people at the local armory in some rural part of the world. He would pick up these different things that he was able to leverage later on. And that was a lot of work.

That's, in a way, how I view not only my experience but maybe how all lawyers, all associates, should view their pathway as well. It's all going to be in service of what their eventual goal is. Now, what their eventual goal is, they'll have to define for themselves. For me, it's this almost theoretical notion that there's going to be some big platform or big stage, some big trial in some place I'm uncertain of, that I'm going to have to be ready for, and be ready to meet the moment. So I think in a way I've used that as an abstraction to say that all of these skills, all of these experiences, are going to serve me when eventually I have to main-event WrestleMania.

Khurram Naik: I love that, because there's something emotionally resonant about that as a driver. Because some abstraction of like, "Oh, I'll prevail in a case with this much in controversy or with this large market cap of a client," is so abstract. I think probably at any stage, even if you've accessed those clients, it's still very abstract. But there's something that's more emotionally resonant about, I imagine, maybe there's more contours you're giving that. For me, something tangible is, with my kids, physical performance for me is two things that are emotionally resonant. One is I want to build a path that minimizes injury and maximizes my ability to move with my kids as they get older, to be able to just continue to move and pick my kids up as long as I can. So that's something tangible and also emotionally resonant. The other version is, if there's an emergency, if I need to grab my kids and run for a mile or whatever, can I do that? Those are tangibly the things I train for.

And what you're saying also reminds me of listening to a recent podcast with James Clear and another host. James Clear, he did Atomic Habits, which I'm sure almost everyone has on a bookshelf at this point. James Clear was making the observation, he was working out at a gym with other people, and his trainer made some comment about how attendance drops on bad-weather days. And whether it was the trainer or James Clear, they came to the conclusion, look, to gain an edge really only happens in moments like that, when there's a little friction involved. So looking for small moments to gain an edge. Sounds like The Undertaker said okay, perform at these regional shows, that's a place I can gain an edge. Because the way James Clear put it is, everyone can work out when they're feeling good, when they've eaten enough, when they've slept enough, when it's nice weather, when they're in a good mood. Everyone's good for that. But where you gain an advantage is when any one of those is missing. Put another way, it takes so little to get an edge. All you have to do is just be a little uncomfortable and a little creative in how you develop that.

I remember Lewis Tompkins, a partner at WilmerHale. Maybe you worked with him, Tim?

Tim Yoo: I did. I was at the firm.

Khurram Naik: So do you remember the story about his first Federal Circuit argument?

Tim Yoo: I don't remember, but why don't you refresh my memory.

Khurram Naik: So I think the details are going to be a little abstract from my memory, but basically he was tracking individual inventors who were trying to get appeals through the PTO, the PTAB, and looking for issues around different doctrines that weren't really tested yet. I can't remember what the issue was, something to do with the obviousness doctrine. But he was very entrepreneurial. He had great pedigree, clerked on the Federal Circuit. He could have been content to say, "Hey, I'm going to get great experiences here and get trial experience." But he was very entrepreneurial in identifying an opportunity where there was something that he could take on appeal himself and handle pro bono. And then he did, and that changed a lot. It's been some years, I don't remember the specifics. And then it helped out some inventor on a pro bono basis. So I'm really struck with stories like that where people are looking for these small edges and gaining them.

Tim Yoo: Absolutely. And I think that dovetails a lot with what we've been talking about this morning, which is, view every situation as an opportunity. And again, that's easy to say, but I found in my career, my short career so far, you take these, and it's not immediately apparent how you're going to use it later. But those experiences that you have, writing this type of motion in one case, researching this issue that you don't think has any relevance to what you ultimately want to achieve from a practice perspective, I find that it's surprising that it always comes back. It always comes back where you're able to leverage a past experience. For example, past experiences I've had where I've been able to pitch clients on cases because I've had experiences with that opposing counsel, or it's been this discrete issue that's an aspect of an IP case that's not necessarily obvious. But to be able to say, "Yeah, I've done that type of case," or "I've appeared before that judge," because there are any number of metrics that people find important in terms of their decision making. To be able to go back and have that experience in the past that you can draw on, I found to be valuable in this profession.

So where you can find your edges, I totally agree with that, because you never know when you're going to need to utilize that. And I think having those small edges obviously compounds a lot over time. And I think about, I'm a big Roger Federer fan, big tennis fan. Roger Federer gave the commencement speech at Dartmouth a couple years ago. And I think one of the parts of that speech that people remember a lot was him saying, "Hey, I won 1,400 matches in my career. Of those matches, I won more than 80%. But guess what proportion of all the points I ever played that I won?" And the answer was, he only won 53% of all the points he ever played. The point he was trying to convey is that it's roughly half. It's just roughly half the points he played.

So it's really just at the margins. And I think that's correct, but my takeaway from that was actually, it just shows you that those small, seemingly small, edges and those margins compound over time and have a huge effect. Because if you think about it, a 53% edge is basically the house edge of any game that you can play in Las Vegas. Any casino's house edge is about 53 to 47. And they're able to leverage that into obviously the big business and being able to pay for all those hotels and casinos. Someone like Federer is able to leverage that small house edge into having arguably one of the greatest tennis careers of all time. So I think that's a good way of thinking about it as well. You can find those edges, be open to the opportunities of where they might occur, and then you'll be able to compound those and leverage those to great effect as you go on.

This conversation about finding small edges and compounding them over a career reminds me of what Priyanka Timblo shared about identifying unconventional opportunities that others overlook. Listen to my episode with Priyanka Timblo here.

Khurram Naik: So how do you define your edge?

Tim Yoo: I think if I had to define it, it's having an open mind. Having an open mind to being open to opportunities, not foreclosing myself just out of hand. That's not to say that you take every opportunity that's presented to you. I do want to make sure that you want to be selective to a point. But I think at the outset, when I am presented with an opportunity, I ask myself, what is this opportunity going to offer in terms of new experiences, new challenges, putting myself in situations I haven't been before, to test my mettle, to give myself an opportunity to grow? I think that's one of the big drivers.

So I think if nothing else, an edge would be having an open mind, not necessarily having to be a certain way. Given that I went to Caltech, had a tech background, it might make sense naturally to do nothing but tech-related litigation. But I've always viewed it as, that's what I like to do and maybe I have an aptitude for that, but I don't want to foreclose myself from other opportunities. Because that's at the end of the day what keeps everything fresh and interesting. And that's really what I want to do. I want to keep it fresh. I want to keep mentally challenged, motivated. And that's really one of the things I really like about our profession, that every day can look differently. Even if it's the same type of dispute, it can have a different character, different posture, different types of things that are important. And that's really dynamic, which makes it challenging and interesting for me.

Khurram Naik: So something I've observed is, in any sphere there's just different ways to win. And so you identify the way that you want to win. But what about a comparably talented peer who takes an alternative approach? So you're proposing, "Okay, I would be open to a wide variety of things. I find that to be valuable." Because I think any number of people say, "Oh, I'm open." What's the way you can define your openness in opposition to some other comparably talented person who just has a different approach, strategy, or value?

Tim Yoo: Perhaps it's an openness to challenges, an openness to being uncomfortable. In terms of leaning into a level of discomfort and unfamiliarity, and just being content to sort of try the same type of case or litigate a certain type of dispute. Maybe to really push myself to be challenged and to put myself in situations that could be awkward, could be scary frankly, is one way I view that openness and flexibility.

Khurram Naik: Does the word versatility resonate with you?

Tim Yoo: It does to a degree, because I think it's good to be, I like to think that there's a versatility to my practice and my mindset. I obviously don't want to overextend that versatility, because you can't be everything to everyone all at once. You want to pick your spots. So I think having versatility and flexibility to a degree is good. But then you also have to circumscribe that with your larger principle of what is this, at the end, in service of. And to me it's always been, like I said, this abstraction that it's really undefined in the sense that, yeah, a certain dispute with a certain amount in controversy on behalf of a certain client with a certain market cap. That's just my abstract notion of, that's what I'm driving for. And I view everything else in service of that. And if it's not aligned with that, then it's an easy call for me.

Khurram Naik: Can you talk about how you position yourself broadly? How do you currently, given you've got this patent litigation core, you're taking on other matters in service of that core. I think there's this concept of having a T-shaped set of expertise. I think that's useful. Both feed into each other where the depth of expertise builds credibility for taking on other matters. People are probably approaching you because if you have a depth of expertise, it's much more intense competition to be a commercial litigator. But it's easier for people to find you in the context of, "Okay, you're a patent guy, and by the way, do you do other things too?" You're just known for something. And then the breadth of the T is also useful, like you're saying, you get these different ideas that you feed into your depth of expertise. So how do you present yourself to the market? What do you want to be known for? What do you think you are known for? What's your goal right now with how you are presenting yourself? Because I think this is a classic issue that every service provider goes through. What's my specialization and then how do I market it, such an ugly word in our profession, but how do I position myself?

Tim Yoo: I think foremost, first-chair trial lawyer, period. I like to think that I can try almost any type of civil dispute. And I think I've developed a certain track record and experiences that support that. So I think that's the first way I like to market myself. And secondly, I have an experience and competence in IP disputes. That's my own proclivity. That's what I like to do. There's a type of dispute that I like to litigate, particularly patent disputes. So that's probably my wheelhouse in terms of subject matter interest and competence.

But again, going back to what we were talking about, it could be any kind of breach of a legal duty somewhere. And I like to think that I'd be able to try that type of case, because I think that is one overarching skill set. Being able to talk to juries, talk to judges, arbitrators, and persuade them. And then the other part of it is having this aptitude of analyzing a technical issue, spotting non-infringement positions, or being able to do a deep dive into the technology, which I really like doing. So that's how I view myself.

Khurram Naik: So when clients approach you, what do you communicate about what they can expect from working with you?

Tim Yoo: If nothing else, I would say level-headed judgment. Maybe sometimes almost in a clinical sense. I spoke about this a lot during our first session, which is I view the role of counsel as managing expectations. And I think that's what I try to do. It's very iterative, and it updates based on what happens in the case. But managing expectations means being very forthright and direct about the aspects of the case and the representation and the risks involved. I don't mean it in a fatalistic way. It just means to be realistic, to give people a chance to assess those risks on their own, and what might need to happen for those risks and sensibilities to change.

So I think if nothing else, I try to be upfront and establish a direct line of communication, to be responsive, to ask a lot of questions, to be there and be responsive to questions. But at the end of the day, you're not really doing your clients a good service by just telling them what they want to hear. I really think you need to figure out what it is that they need to hear, and not just give them an information dump about, "Hey, here's all the information that's possibly germane to the decision that you have to make." It's really, a big part of our role, and I don't think outside counsel should abdicate that responsibility, of curating that to a degree as well. Curating the information, distilling it down to the dimensions that matter, that move the needle in terms of a decision, and then delivering it in that way.

I don't mean to suggest that there's no bedside manner involved. I think that's a big aspect of what we do. A big aspect of what we do is making sure that the things that are not important or productive to a decision-making process are filtered out. One thing I've noticed is, for instance, sometimes you get an email or a nastygram or however you want to characterize it from the other side, and sometimes that natural inclination might be to forward it to your client directly and say, "Look at all the things they're saying about your case and all the vulnerabilities." And the client is going to react to that in a very visceral way, more often than not, because they're not conditioned to speak the language that litigators speak. Because for me, when I see something like that, I'll just distill it down to what the upshot is. What position are they taking? Are they agreeing to my proposal? Are they offering a different proposal? That's really the main point of communication during the litigation stage.

So it's not always productive to go ahead and forward that along to your client, because they're going to have an emotional response. And that's not necessarily the best place to be. I view my job as taking what the upshot is and then being able to curate that and communicate that to the client. Because then they can take out all the emotion and make a rational decision.

Khurram Naik: Yeah, that's really helpful. And I'll share with you how I'm thinking about this. I'm curious to what degree this overlaps or maybe the structure is not analogous. But I'll share how I'm thinking about my client management. These are things that I'm talking about publicly, and I want to continue to talk about publicly. I guess I'll be really interested in your insights. On the topic of it's not just what you say but how you say it, I guess it'll be interesting to hear ways to make this more resonant and more persuasive.

So a core premise that I've honed in on is that every firm is a bundle of benefits and costs. That's a core concept, and I think everyone has to get comfortable with it. And I think that's a threshold reality that a lot of lawyers can't accept. And so that helps sidestep a lot of therapy sessions into, "Hey, look, the reality is that your firm is a bundle of benefits and costs, and so is that other one. There's not a better firm. There's just one that has a different profile of benefits and costs." And based on your stage and your goals, one might be a better platform than others. You can describe some of your goals professionally about what you want to accomplish. One firm is a better platform or another for the goals that you have. And for another litigator, maybe with a different set of goals, another firm is a better fit. It's just that simple.

So from that flow a number of different core layers, and there are other things that intersect with that. From that premise, you need to identify what the key tradeoff you want to make is. And the thing that we have observed is that's something you discover. And so, in the course of gaining options, you get clarity, not so much on the firms, yes, you get that as well, but more fundamentally on what's the most important tradeoff to you. What is the thing that is most important to you to trade off? And you really want to hone in on one, because there are so many variables that you could compare all these different opportunities. And lawyers are researchers by profession. Just like you're saying, you're trying to curate an experience and make this simple to get to a resolution and decision point. You're not trying to add complexity. As a lawyer, that doesn't make you seem clever or smart. What's helpful is, "Hey, let's distill this down." So that's our view. We distill this down to, what is the one key tradeoff you're making?

One thing that flows from that is, what you want in this process is an objective advisor, because if every firm is a set of tradeoffs, what's not helpful is someone pitching you. There's a reciprocal relationship between our business model and this approach. Any number of other recruiters might really be working with one firm primarily, and they're pitching on that firm, saying, "Hey, there's a reason we have really deep ties to blank firm, and here's all the reasons why this firm is the best place to be doing patent litigation." It's a very different business model. And like I was saying before, there's just different ways to succeed and add value in the marketplace.

So our approach follows from, okay, if everything is a bundle of benefits and costs, there are just tradeoffs among them. And you discover the tradeoff in the course of this. And that's this pleasant surprise you experience. So that's the space that we create for emotion. We provide structure. Here's this very analytical structure of, every firm has a bundle of benefits and costs. And then there's a number of things that flow from that in terms of the structure of how you work with us, what role we play, because you talked about the role of counsel earlier. And then you also talked about shielding emotions, filtering information. So I guess, maybe talk about what emotional discovery is like for the client, or in a jury context, for the jury. What's the way you can steward that and say, "I don't know what your emotional reaction is going to be when you pick up that rock or look behind the tree, but I bet you'll experience something new, and then that itself is helpful and predictive."

So big picture is, your clients are coming to you for authority and for credibility, to tie back to something you said before. And to help have lower variance outcomes. At the beginning of litigation, it's very high variance. Who knows what can happen. My perception of a skilled litigator is to reduce that variance over time and help a client get clearer around, okay, this is kind of how it's all settling out. So I'm interested in hearing from you, that interplay of, when it comes to counseling a client, or if the analogy is there, how you approach working the courtroom, laying foundation analytically for credibility and leaving room for emotions. Because alternatively, another approach to recruiting might be, "Hey, I'm going to get you really excited about this firm." That's the space for emotion. "I have expertise and authority about this firm, and I'm going to get you excited about that." But it seems like no matter what, there are different approaches, and each one has some interplay between the analytical foundations of authority and the emotional resonance. And whether that is something that you are curating or not seems to be one of the variables. I wonder if that resonates with you when it comes to client counseling, or in the courtroom.

Tim Yoo: It does, because it's hard to discount the emotion in terms of your client's decision-making process. For your client, no matter what type of dispute it is, there's going to be some level of emotional investment. It's going to be hard for them. This is taking up years of their time and their resources and their emotional capital going into this. So there's definitely going to be, I think it's unrealistic to expect that there's going to be some type of clinical analysis where they apply the right coefficients and the quadratic formula spits out the right answer. I think that's unrealistic.

But again, and maybe this is an approach that needs to be calibrated depending on the situation, I do think that it is important to try, to the extent you can, to quantify that as much as possible. A good analogy I got was, and this is not my area of expertise, I don't do criminal defense, but I have colleagues that do. And I always ask them, how do you do that? When I'm advising my clients, I might say, "I think I'm right, but if I'm wrong, oh by the way, this could be extra dollars the other way." That's one thing. But I always find it hard to quantify, "I think I'm right, but if I'm wrong, this could be five years of your life or 10 years of your life." How do you advise clients that way?

And I think it's a similar approach where they say, look, you try to quantify in terms of, "Well, how important is that? Do you want to roll the dice with going forward? Do you want to take a plea? Think about, do you want to guarantee that you'll be there for your kid's high school graduation, or do you want to leave that up to chance?" And in a way, you're tying the consequences of those decisions to an emotional event.

And I've used that as a helpful rubric, in the sense that my whole thing is, I try to give people enough information and obviously show them the evidence and the law, my own experience and my thinking behind certain things. My whole philosophy behind doing all these repetitions and preparing for these performances is to really try to play for the 30th percentile outcome. So I know that if I've practiced enough and I can do it 10 times, I want to make sure that the 30th percentile level of performance is still very good. And sometimes I might hit the 70th percentile performance and really do well. But I don't want to bank on that. So I want to make sure that for me, even a 30th percentile outcome is good.

So in a similar way, I want to give the clients, "Hey, if this happens, this could be your 30th percentile outcome. This would be your 70th percentile outcome. This could be a 50th percentile outcome, the middle of the road." I want to give them enough information to evaluate that. And it's really up to them to figure out how much of the emotional component is going to play into it. But I do try to quantify that as well, saying, "Look, vindicating a principle is one thing, but this is what you're going to be willing to do to take on this much risk." And that risk can take many forms, in the form of additional fees, additional uncertainty in terms of what the exposure is, the time investment, the emotional investment.

And maybe this is a wrong-headed way of thinking about it, but I find myself often telling clients, "Look, I understand the right or wrong aspect of it, but right now it's really about risk allocation as opposed to right or wrong." Right or wrong is something that you have a notion of in terms of morality and principles. But if you're talking about making a decision in the litigation context, you really should be thinking about it in terms of allocation of burden. And maybe that's too clinical a way of thinking about it, but to your point, I do think that you need to give them a rubric of how they're going to quantify their emotions.

Khurram Naik: And a key part of this concept is when you experience the emotions. And so my premise is that the best place for the emotion is later in the process, in the form of a pleasant surprise. And I think that just resonates with different people to different degrees. For some people, they don't want a pleasant surprise. They'd rather trade off the pleasure for certainty earlier in the process. And so, is there something, I guess, in terms of allocating when someone experiences emotion, or this concept of being surprised at all, or some analog to that? Is there something that you're adding to the process? Because part of it, I think you're talking about client agency, and not abdicating everything to the lawyer serves more than one purpose. Also, the client has skin in the game and is being invested in the process and thinking through every step of the way, not just abdicating decision making to their agent, their outside counsel. So I don't know if that resonates as part of this, to what degree surprise is, and something sounds like a negative thing for a client. Maybe the contexts don't really match up, but I'm just curious if that is part of how you counsel your clients as well.

Tim Yoo: I don't think we're talking about different things. Maybe surprise is one thing, but maybe not. Think about uncertainty, a condition happening. A condition is something that's not certain to occur but could occur. I think you put conditionality into the advice that you give. "This could happen. I handicap it as, these are the things that would have to occur before that, or this is the likelihood." And allow them to make a decision on that. I want to make it very clear that if it's a condition, a contingency that's not certain to happen, that they know that maybe their decision making shouldn't be dependent on that happening. And therefore, if that condition arises, then to use your term, they can be pleasantly surprised about it, and maybe that will affect their decision making.

But I think it's important to be very upfront about what you're saying are the conditions. And the flip side of that same coin is that don't try to set their expectations too low, either. Because if it's realistic that it's likely to happen, you should let them know that too. You shouldn't just take a fatalistic approach and say, "Hey, that's not guaranteed, there's no way that the judge is going to interpret this contract this way." If you think that's the only reasonable conclusion to reach, you should tell them that.

Khurram Naik: How do you relate to the concept of ambition? You've documented growth at this stage, and before we started recording, we talked a little about getting into a phase where you're comfortable and appreciating the rewards of hard work that got you there.

Tim Yoo: Yeah, I'm curious about how you relate to the concept of ambition. Ambition as distinct from growth, in terms of professional growth, is that what you're talking about?

Khurram Naik: Yeah, there's a connection between those two. And maybe a way to put it is, are you more or less ambitious than you were five years ago?

Tim Yoo: I would say if nothing else, maybe about the same or even more. But to be very specific about what I'm talking about, ambition in terms of personal professional growth. In terms of being able to select opportunities, pursue opportunities, put myself in positions to get more opportunities that speak to me. I think I'm just as ambitious as I was when I started, five years ago, whatever parameter you want to start from. I think that, for me, hopefully will be never-ending.

Because I want to be distinct about that in terms of ambition, in terms of whatever the byproducts of having goals of professional growth, whatever byproducts that might have, that's one thing. I don't necessarily fixate on that, whether that being the material rewards or outside recognition, whatever you want to call that. It's really, I find the pursuit of those opportunities and those growth opportunities fulfilling in itself. And I think the other components, whatever comes with that, will take care of itself to a certain degree. But for me, it's always certainly been the case to focus more on the growth itself as an end in itself.

Khurram Naik: Do you think in terms of goals? Do you have some identifiable goals?

Tim Yoo: It's funny, yes. I think you've got to have goals, because if you don't have something that you're striving toward, for me, goals are things that are actionable things that you write down. Because to me, it's not a goal until you write it down. So I definitely write them down. I put together my vision board recently about the things that I want to accomplish and drive towards.

It's funny, I was showing my, I actually work with a performance coach, or performance consultant if you want to talk about it. I was showing her, she's my former law school classmate, she was great. I was showing her this vision board and her first comment was, "It's not ambitious enough. You should actually write down goals that are more ambitious." Because the things that I wrote down, like, "Try to be a more present father, be a more loving husband, try to work on my craft," those are almost like things you're already doing. So she was saying that I should really write down stretch goals, like this is the level of growth of your practice, how many trials you've achieved, or things like that. I think she would really encourage me to write down and shoot for.

So I think that's right. It doesn't manifest until it's concrete and you see yourself striving toward that. Because a big thing for me now is, I try to curate a lot of what I look at on a day-to-day basis. Because obviously, what you see is what you desire. And I think it's very important, especially in the age of social media, you can find yourself doom scrolling and then looking at things like exotic watches or vacation locales and things like that and just convincing yourself that this is something you need to live a fulfilled life. And the minute that you get those out of your eye line and start looking at other things, then you really go toward the things that you're looking at. So I find myself, more than anything, really trying to curate what comes into my field of vision. Obviously it's hard to control all the time, but I think that's where having your goals written down, creating a vision board of what you prioritize, is very important.

Khurram Naik: What's been the biggest takeaway from working with your performance coach?

Tim Yoo: Yeah, I think in terms of the process involved, being equipped with how you think about things, the tools that you apply to it, just having someone to bounce ideas off of. In terms of, "These are my goals," being able to vocalize those and put words and names on what your ambitions are and what your desired outcomes are. I think that's been very helpful. And just having something that's actionable, I think was important. Because for me, I can work with a swing coach for my golf swing, or a personal trainer for physical fitness, or a dietician for nutrition. So I think given that what we all do as lawyers is, in a sense, the whole theme of this discussion today, how do you optimize performance and put yourself in a position to meet that moment and to be the best? And I think having, maybe performance coaching isn't the right label for it, I kind of view it as a consultant, a professional consultant. And I found that to be very helpful and productive for me.

Khurram Naik: Yeah. And to your point about what you see influences you, I think the people you associate with also influence you. And so I admire you, and I really love our conversations, and how much you get me excited and ambitious. One of the things I really admire about you is how you are very passionate about performance broadly speaking. You look for examples of it broadly. And you're really relentless in pulling ideas from that. So I'm glad that you do that. You inspire me to do more of that and curate more for myself, digging into what elite performance looks like. But yeah, I really dig the conversation, as always, Tim.

Tim Yoo: Likewise. I could speak to you for hours. I always enjoy the time. I feel like any day of the week, you can just give me a call, we can pick up the phone and press record and hopefully it'll be a worthwhile listen. But I appreciate the opportunity to come on your podcast again, and I enjoyed that conversation immensely. So thank you.

My Sleep Strategies

Here's what I'm doing to improve and prioritize sleep now:

• Use my Oura ring to track sleep. It helps me understand the components of good sleep and track the factors that impact it: eating close to bed, caffeine consecutive days in a row, late-evening stressors.
• Turn down overhead lights starting at 6pm. Dimmer lights lower to the ground simulate the natural setting of the sun and prompt sleep.
• Stop eating at 6pm (but often 6:10-6:20). That means we've done a lot of digestion by bedtime, and our lower heart rate helps us sleep.
• Go to bed between 8:30-9:00pm. We have children that are unpredictable overnight, so we do what we can to protect sleep. A tight schedule promotes predictable sleep, which also impacts metabolism and energy.
• Nap when I can (not often, with nannies, cleaners, and children in and out of the home), especially when I'm under the weather. My Oura ring finds a measurable impact on alertness when I nap, and I notice a boost in mood and attitude.

Last Night's Results

Here's my sleep details from last night, from the Oura app. My sleep isn't perfect. I didn't get as much deep sleep as I typically get (around 1.5 hours), and I had a lot of movement (our 9-month daughter working on sleeping independently). But I'm happy with the composition and quantity of sleep. I feel good.

Try It Yourself

So this weekend or next week, maybe you can give yourself permission to go to bed early or take a nap. As a parent of a toddler, here's a tip for a 10-minute nap that Navy SEALs use: put on some white noise, elevate your legs above your heart (use a couch or pillows), cover your eyes, and enjoy your moment of rest.

Prioritizing sleep has been one of the best decisions I've made for my health and career. Whether you're in a demanding job or managing a busy household, protecting your rest pays dividends in energy, mood, and performance.

Give yourself permission to rest. Your body and mind will thank you.

Here are 18 proven tips for getting the most out of a conference: Focus on the quality of interactions, not the quantity of them. Get to know a handful of people. Over time, you'll meet their friends and then their friends and so on, gradually building your personal network. Evaluate the conference to determine whether it's one you want to attend again. You'll get the most out of a conference by returning year after year. Ask people what they think the most interesting panels or events will be. This will help you allocate your attention and better understand the conference program. Don't be shy about introducing yourself to the biggest stars of the conference. They're there to meet people. If some people don't seem to reciprocate your interest in connecting, don't let it upset you. You'll find your people. Keep introducing yourself. Ask people why they came to the conference. People may surprise you with their responses. Many of the best events held during a conference are unconnected to the official program, held off-site, and announced by word of mouth. Be flexible with your schedule, be inclusive, and be assertive about getting invited. After meeting a colleague, connect promptly on LinkedIn. Send a short message about your conversation and follow up in the next month to schedule a call. You’ve already done the hard part in making the connection; sustaining connections is both the easiest and most important part of building a lasting network. Make sure you eat good food, get plenty of sleep, and stay hydrated. Don't feel pressured to go out or make choices you'll regret. Feel free to take plenty of breaks to recharge. Don't feel like you have to be a part of everything. Stretch yourself by walking up to a group of people you don't know and introduce yourself. People are watching; don't do anything you wouldn't want someone else to observe. Research people who you want to meet in advance and reach out and invite them to connect at the conference. Ask people in your network if they’re going to the conference you plan to attend. You’ll both have a better experience if you know someone there. Moreover, meeting up at a conference is another way to stay in touch with the people in your network. Look for opportunities to connect with people who share interests or work in similar practice areas. The more connections you form in your network, the more valuable the network becomes. Pick a conference you’re excited about attending, not the one you feel obligated to attend. You’ll get the most out of it if you’re excited to learn and meet people. The best opportunities to connect with people at a conference are in the lobby and hallway, not in the conference room during a panel discussion. You’ll get the most out of a panel presentation if you’re on the panel. You’ll learn and build relationships with the other panelists, and you’ll build your authority as a speaker and thinker.

A great attribute of the legal profession is that it is full of inherently social people. These eighteen strategies—from prioritizing quality connections to understanding where real networking happens—transform conferences from overwhelming events into powerful career-building opportunities. The key is approaching each conference with intention: knowing why you're there, who you want to meet, and what you want to learn.

I've written more about this in Khurram's Quorum - Ep 045: Joe Ahmad on sincerity vs. polish, empathy-based persuasion, and taking big risks.

Whether you're exploring a new practice area or deepening expertise in your current field, conferences offer unparalleled access to curated networks of specialists. The investment pays dividends when you commit to building genuine relationships, following through on connections, and returning year after year to strengthen your professional community.

Read the complete guide with all 18 detailed strategies on Vault's website.

Read full article here.

We talked about what's actually driving demand for elite patent litigators right now, how my time at Goodwin shapes the way I recruit, and where I see opportunity in the current market.

If you work in patent litigation or are thinking about a move in 2026, I think you'll find this worth your time.

I explore this further in Why I Prioritize Sleep and How I'm Improving It.

From the interview:

"Patents keep issuing, products keep launching, and companies must keep defending market share. Whether in standards or biologics, these disputes remain high-stakes and often bet-the-company, which means demand for elite patent litigators never truly softens."

"In life sciences, new drugs and biologics move through development, regulatory approval, and commercialization on a continuous cycle, and each stage creates predictable points of dispute. Hatch-Waxman litigation, biosimilar cases, and follow-on patent challenges aren't distractions from core businesses, they're central. A single patent decision can determine whether a company secures market exclusivity or loses it overnight."

This is Part I of a three-part interview. Parts II and III cover how my Biglaw background informs my recruiting approach and where the real demand is for top-tier patent litigators today. If you're considering a move in 2026, or if your firm is looking to add talent, I'd love to connect.

Read the Full Interview

In this conversation, Mani walks us through how he went from trial lawyer to GC of a multi-strategy fund to co-founding Signal Peak, his own litigation finance firm. We dig into how he and his partner Lauren Harrison source deals through trust-based relationships with Texas trial lawyers, why they structure deals with real alignment on both upside and downside, and how the operational habits he learned at Susman Godfrey power everything they do today.

Keep reading below for the full link to the episode and the full transcript of our conversation.

Top Insights

Below are the highlights of our conversation:

• Intangibles Become Tangibles: Mani's litigation fund exists because of a lunch he had with a struggling associate in 2012. The relationships you build as a peer trial lawyer are the same relationships that generate deal flow years later.
• Speed as a Competitive Weapon: Because Mani and Lauren have tried the same types of cases they fund, they can underwrite faster than competitors who need to hire outside expertise. In a market where lawsuits are depreciating assets, that speed wins deals.
• Alignment on Both Sides: Signal Peak structures deals so the funder shares real downside risk with the law firm. If a case settles low, they take it on the chin alongside the lawyers. That skin-in-the-game approach creates a flywheel of repeat business and trust.
• The Task Sheet Leader: Mani credits his operational discipline to Steve Susman's "one riot, one ranger" principle. Every task gets one owner, nothing falls into a black hole, and monthly meetings are reserved for stepping back and steering the ship.
• Focus Creates Optionality: By narrowing their fund to cases they actually know how to try, primarily Texas commercial and patent litigation, Signal Peak avoids the trap of chasing every deal. That focus lets them move fast and take concentrated risks others shy away from.

Listen Now

Catch the full episode on your favorite podcast platform.

Spotify

Or click here to listen on Spotify

Apple Podcasts

Or click here to listen on Apple Podcasts

Full Transcript

Khurram Naik: Mani, so great to have you on. It's been great getting to know you and excited to share your story here.

Mani Walia: Thank you so much for having me. As part of my homework before joining, I listened to a few and then saw your list of guests. So I truly am honored to be part of this group and join the ranks.

Khurram Naik: We're really looking forward to it today. Okay, great. So in some of our conversations, we've been exploring how you came to be where you are. You're at Susman, one of the best trial firms in the country, maybe the best. And then you eventually went to a multi-strat fund where you eventually launched some litigation finance vehicles. And then went on to launch your own fund. So that's the trajectory. And all started with spending some time with a colleague who was having a hard time back when you were at Susman. So can you share that story and its impact?

Mani Walia: Yeah, thank you for asking. And I'm so thrilled to be on. It's interesting, when I was doing all this you don't connect the dots and you know imagine what's going to happen. But looking back, it's fascinating because it's just a story of good friendship, which maybe is really what networking is about. So this story, which is a true story and now has helped launch our new fund, all started way back probably in 2012 when I was a baby associate at Susman Godfrey. It's a very prestigious and amazing firm. It's not known for a great quality of life. Let's put it that way, at least back then. So there was another associate, terrific smart guy, probably two times as smart as me and just an amazing lawyer, baby associate. He was new to the office. His wife was still doing residency. She's now a dentist in Houston. But back then she was a dental resident somewhere in the northeast. And they had just had a kid. So this guy was slogging, I don't know, 90, 100 hour work weeks. And it was tough for everyone. And so maybe his first or second week at the firm, I noticed it, probably just because a lot of people have figured out how they network. It just was inherent for me to walk around the office and notice these things and try to connect with people. And we went out for lunch and he got a chance to talk and be vulnerable about what he's going through. And it's not really my natural instinct to be vulnerable back. But I talked about how it's tough for me, and I have a kid too, and my family's in town but it's still tough to juggle everything. And that one conversation started a real friendship within this firm, Susman. And then fast forward nine years later, this guy makes partner, is an amazing rainmaking lawyer. We had just started the litigation work at my previous company. A month into it, he emails me out of the blue. We kept in touch, but he emails me and says, you know, you've been a good guy, can you fund this case? And that's how it started. It went on to be one of the biggest cases in 2023. I know you do a lot of patent cases. It was one of the biggest cases in the patent arena and it put us on the map, put me on the map as a funder. And it all started from personal connectivity. And so it's just a story I sometimes try to tell my kids about being friends and connecting people. I think it's a great story because it truly did change my career.

Khurram Naik: Can you break that down a little more? Tell me about it. So you got the case. This was a major inflection point because you hadn't funded a patent case yet, because you said you were only a month into working at the fund. So it was the first case overall?

Mani Walia: The first case overall. And so my whole experience before that was trial lawyer. So I wasn't in litigation finance, this was a transition to it.

Khurram Naik: How did you handle it? So your friend comes to you, he's got a case. You were a month into starting the fund. Now what?

Mani Walia: What was really helpful is that the framework for that had been put in place in the months preceding. And I say this to a lot of lawyers. I think lawyers are good leaders. We knock ourselves and say that we're not entrepreneurial or we're not having two new ideas per day like what we think of great CEOs or visionaries. But lawyers, in my view, are very good at task sheets, to-do lists, and getting things done. So although we were just a month in, we had built the infrastructure on how to underwrite, have the fund in place, have capital in place. So we had all that there. We just weren't ready for such a big, prestigious case to come in, just because we weren't expecting that. We were planning to have a few years where we're trying to get enough deal flow to justify having a fund. But that preeminent case from this amazing law firm and amazing lawyer came in very early. The infrastructure had been there because of this task sheet mentality.

Khurram Naik: And so before you got that, how did you identify the terms? What were the terms of fair market, and how did you come to determine those for this matter?

Mani Walia: That's another thing that I hope we spend some time today on, lawyers as business leaders. There's a lot of axioms that I live by. I'm sure many of your other guests and you might live by them too. One of these things always floating in my mind is the Jeff Bezos rule of making decisions with 70% information. So how did we have the terms before we started the fund? I didn't want to start the fund until everything was in order. Not to say it was perfect, right, 70%. But we had a litigation funding agreement ready to go. How did I source that? It was on our task sheet to come up with it. I found publicly available ones that were by other leading funders, cobbled together my own template and had it ready. So in many ways, we had built the house and now we were just looking for occupants. And it just blew our mind that the first occupant was this kind of case that everyone in the litigation funding community would have wanted. The complete alpha generator, the value add, it's sourcing. If you have great cases in the top of the funnel, so to speak, they'll make their way down to the bottom. So the infrastructure was in place. We were just amazed that the sourcing, which is the highest alpha, came simply from trying to be a decent human being and connecting with people and then keeping in touch. Which, you know, maybe is easier said than done. But if you can do it, it's not a very tangible skill set.

Khurram Naik: And so then, help me understand. That asset performed very well. Investors are very happy. Are there any, and this maybe a very basic question, but does any kind of performance, does external performance, are there any kinds of performance that matter for investors? Are they just looking for pure return? Is there something about the nature of performance, say timeline or nature of recovery, that matters to the institutional investor LPs?

Mani Walia: It's not a basic question. We get that exact question or similar question from very sophisticated LPs, professional money managers at pensions, university endowments. Returns are important, and I would have thought at the beginning returns are like the trump card, like it's the beginning and end. It's really not. Because even with that great return off of our first case, and it was great by all objective measures, I know all the stats on private equity performance. Generally you want to two times your money in three to five years. So we had well surpassed that, it was great. LPs though are looking not just for one-hit wonders, because they have this sort of jaundiced eye. The other things they look for are repeatability. Team, as cheesy or trite as it is to say, people want to work with people that they connect with. I do this with the service providers we hire. It may be the same in your world, of the service providers and lawyers you work with, you know, have some connectivity with them. So to get back to it, LPs are looking for returns, they're also looking for repeatability of the process, looking for the quality of the team, and then looking for what's your differentiator. Is it that you happen to be some of the smartest guys and gals in the room on international arbitration? Or do you have a great network? What's your pipeline like? That maybe is the differentiation. But those are probably the four biggest factors. And you can't hide from returns. You're only as good as your last trades. If you have everything else but then a few bad trades, it'll be challenging. But returns by themselves doesn't do it.

Khurram Naik: So then that performed well with the criteria that was beneficial for those LPs, and so they saw repeatability in this process. They saw maybe some network effects, some other indicia that this was a winning team, this isn't a one-off thing. So then did they communicate what it was specifically that they saw? Like, was it communicating, hey Mani, you got this case from a colleague, you're probably going to get other cases from elite trial lawyers. Did they communicate what it was they really valued about you?

Mani Walia: A little bit. It's not as clear with communications with LPs as the way you just framed it, probably because they expect the manager, the company, to sort of intuit these things. And I guess the best way they demonstrate how much they like it or they communicate is by reallocating into future funds. So that was the evidence that people liked it. And the litigation finance business, in my view, it's really the intangibles are the tangibles. If you can source well, that means that you've had to put in the years of work beforehand on who your network is, do they trust you. You can't just come back to people after 10 years of being silent. But because LPs, institutional investors, could see the pipeline and the networking prowess that I was able to demonstrate, that is the repeatability of what I've been able to do in litigation finance. And so from there, investors seemed very happy, and then I launched my own fund.

Khurram Naik: That's quite the genesis, from having conversations with somebody who was looking to have a deeper conversation. Let's go back to sourcing because it seems that in a fund there's some fundamental functions that a fund has to perform. It has to source matters, it has to diligence them, and then it has to monitor them. I think different funds have different degrees of monitoring involvement with their matters. And probably, I guess we can add as another function, structuring the transaction. I guess there's some competitive advantage there in coming up with the right terms that aligns incentives. And so it sounds like of those functions, your competitive edge, maybe there's other functions you can tell me about, but it sounds like you're saying your competitive advantage, the dimension in which you're most dominant, is sourcing.

Mani Walia: I would say that our Signal Peak competitive advantage is the sourcing and underwriting. We sort of joke, and I don't use too many of these financing terms, but we make all of our money on the buy. So that means when we get into an asset or investment, the value generation is at the beginning, sourcing and underwriting. And then once it's in the fund, these are cases. And that's what's so unique, and I'm glad I'm on this podcast with you to talk to lawyers, or hopefully some lawyers are listening. How interesting that lawsuits, things that we learned in law school about, doctrines, they are big-time assets that folks on Wall Street want to get access to. I get a chance now to go speak to law students a lot, and I always say, how cool that the legal mind is such an asset now that Wall Street wants to know how to underwrite cases. That's something only we, as lawyers, the 1.8 million lawyers in the country, which sounds like a lot but still not that many, and of that maybe half of them are trial lawyers, they want our brain. They want to know how to underwrite cases.

To answer your question, that is our competitive differentiation. I'm so lucky that I partnered with someone who I admire in the industry. She used to be my biggest competitor, because the same attributes that I have are ones that she has. She's a double federal clerk. She was a partner at Vinson & Elkins, which is a prestigious Texas firm, and then at Jones Walker, another Louisiana and Texas firm. So the same connections I had, she has, but at a different vintage of her career. And that has been our sourcing advantage and the moat that we have. Trial lawyers like working with other trial lawyers. It's just part of the elitism maybe in the profession. And that's what we have. So our intangible that turns into the tangible is, so-and-so corner office partner at, I'm just making this up, Quinn Emanuel or Boies Schiller, they want to work with someone in the litigation funding community who's not just a professional financier who's like, oh I need to fund your case, we can make a lot of money. They want to work with someone who speaks the lingo, who's one of them, and can understand the nuances of litigation, standing, privilege, settlement. And that's what we have to offer.

Khurram Naik: So I think that's a dimension I'm really interested in, this transition you've made. And I've seen it in my own work because I was a patent litigator and now as a recruiter, recruiting is really more common with deal work than litigation. But there's some principles that you use from litigation, how to communicate effectively, how to persuade, how to structure negotiations effectively. There's some things litigators do well that way. But I think litigators probably overrate their ability to do deal making, among other reasons, because they have this artificial world where there's a set of rules in disputes before a tribunal. I think the stereotype of litigators having more of a zero-sum mindset is largely true in my experience. And so it's a fundamental shift in mindset and skill set to think of work as deals. And deals above all to me means non-zero sum, an understanding of how a transaction can benefit everyone. And so I see a major departure from litigation to that. But I'm curious how you see it. It feels like based on what you're describing so far, you see more of a continuity. But I'm really curious to see if there's any kind of mindset or skill set shift from practicing as a trial lawyer to now doing the work of deals.

Mani Walia: I see a little bit of both. Continuity, obviously underwriting cases, you're putting on your legal hat and analyzing, can I get indirect damages in this case, what's the statute of limitations. You're putting on your sort of law review, law clerk, or litigator hat. But the aspect of thinking about these in a non-zero-sum game is something I'm glad you noted, because it's very true. I bring this up only because it's relevant here. Way back when I was a baby associate at Susman, with different cases, I was on a patent case though. I was opposite a young associate at Quinn Emanuel. And the way I litigated and the way he did kind of falls in that old school gentleman and ladies code, which is we vigorously, we're both competitive, we wanted to win, and we fought hard on issues, discovery issues and whatever else. But then we developed a friendship, like when the game is over you don't have to curse your opponent. And we were talking a little bit about this before the podcast started. Old school politics was a little bit that way. Ronald Reagan and Tip O'Neill, they would shake hands after and have a beer after duking it out on policy. So anyway, I bring that up to say that's now a lawyer who sends us cases, even though we met in an adversarial setting. Because in an adversarial setting, I never had a zero-sum game, that after the game is over you never think about this guy or whatever. And so we generated a friendship back then.

The deal-making point you make is great, and I'll conclude by saying this. In litigation finance, if you're a funder like we are, there is a little art to it. Because now on the plaintiff side of it, there's plaintiff, law firm, and funder. You're adding a new element after hundreds of years of it not being there. It is a little bit of a delicate balance, which again is part of our intangibles becoming tangibles. We know how to structure these deals so that the trial lawyer and client remain king or queen of the case without impeding on what they should be able to do. And the only reason we're able to structure those deals with so much trust is we walked in those trial lawyer shoes. We don't need them to call us every three minutes after a case has started. We let them sort of do their thing. So we can expand on that later, but I really think there's a little bit of both, litigator hat and then thinking of deals in a more holistic sort of way.

Khurram Naik: Let's talk about that then. So there's this three-part aspect, and recruiting is the same way. There's lawyer, firm, recruiter, and you're aligning interests among all three. And so I think what you're saying is like there's this concept of the natural state being lawyer and firm. But there's no natural state. Just like when I buy a house, there's not a natural state where you just hand a bunch of cash to the seller. The natural state now is there's a funder, a market, a mortgage company of some kind or some sort of lender. So among other funds, for how other people structure this three-part relationship, what's your impression for what differentiates you in how you're structuring versus how peers of yours are structuring? What is the principle? Maybe it flows from trial lawyer alignment and there's some sort of operator trust that results in intangibles becoming tangibles. Maybe something about that relationship results in different terms, something quantifiable. How would you codify or summarize your approach and any departures you see from how others structure theirs?

Mani Walia: We are very fortunate because of the sourcing advantage and perhaps sourcing moat that we have for elite trial lawyers in Texas. And it's like a one or two degree separation with elite trial lawyers. We do a lot of repeat business. And then when you add on that not only is it repeat business with person X at whatever firm, but we also know him or her because maybe we were opposite in a case with him or her, or we were alongside that person. And Lauren has that just the exact same as I do. When you have that, and then you add the trial lawyer understanding, like, I understand how big your shoes are, it does generate into several things that I think differentiate us. And this is no slight to our friends in the industry, it's just that unique background. We don't grow on trees, right? This just happened to be, we're happy to be lucky.

So here's how it manifests itself in several ways. Number one, monitoring. You talked about that at the beginning. Probably because a lot of litigation funders actively monitor, maybe that means once-a-week calls. I have recognized and figured out that very rarely do these elite trial lawyers want to go on a phone with you or me or funder Joe Blow and say here's how the case is going. They're busy. And why do they need to account to some suit on Wall Street who's not even a lawyer, or maybe is a lawyer but not to their standard? So number one, we don't do these standing check-ins. That doesn't mean I'm not following the case. I have PACER, I have Westlaw, I have whatever other sources. I track the case, and again, as a trial lawyer, I can read three things and figure out exactly where things are. And then I'll have lunch with the lawyer when we catch up about personal, family, and the case. So it's much more organic in our monitoring. That's advantage number one.

Advantage two, which is very substantive, is the way we structure deals, which is in the minority, I believe, of the industry. Most funders want to make sure, each sort of myopically, that each individual deal has a downside protection. So in an example from these other funders, they'll require that the funder hit some return before other people on that side make a return. It's like they want to make sure, in a case, the quintessential example is, imagine a case where everyone's underwriting for a hundred million dollar settlement or judgment, but it's a ten million dollar settlement. The funder wants to make sure to hit its return or at least get closer so it doesn't get a zero. We take a different view because we do so much repeat business. We can bet on the long-term success rate of a firm. So we don't need to put some safeguard for our downside. If that same scenario happens to us, we really take it on the chin. Why do the trial lawyers like that? Because they recognize things could go sour in an individual case. But if you're betting on us in like five or ten, law of averages, it's a virtuous circle. So that's a big captivating thing for these lawyers, whether the case goes poorly, we still share in the outcome together. And that's something that generates a lot of goodwill in the sourcing market for us. Those are two examples that come to mind.

Khurram Naik: Yeah, I think the term that Nassim Taleb would say is skin in the game. You're aligned in that way, and that has consequences when it tells you lose. So with repeat business, do you start as a portfolio? Are you funding a portfolio of matters for a firm? That is a common arrangement in the industry. Any number of funders make these public announcements about funding arrangements with Kennedy or whatever law firm. How do you think about that?

Mani Walia: It's a tool in our toolkit. There are other litigation funders out there and we find ways to separate ourselves. I talked about sourcing probably already ad nauseam. We are open to that, and we have stuff in the pipeline where we bundle cases. But we like to be where no one else is. And that's also something that's been in my mind career-wise, where I sort of viewed my career as like a chess board. I always wanted to get to the most elite point because then you have optionality. If you take the hardest job and the most elite job out of law school, you can always go down, work somewhere with better work-life balance.

We think of it the same way. And here's what I mean by that. A lot of funders don't like to take single case risk. Another example, we've funded cases that have a single patent at issue. A lot of funders say, no, we need to hedge our bets, which I understand, it's very sensible. Why don't we worry about that? Because again, we have tried those types of cases. We see the value. If you take risk on those types of cases where no one else wants to take risk, they can be huge home runs. Obviously there's big risk there as well, so you need the portfolio effect. Now I'm sounding like the kind of private equity person I said I don't like too much. But if you build a portfolio with enough cases, enough shots on goal, then you can take those risks.

So that's one way where people can see the real alignment we have. I joke with our lawyers, we ride down together and we come up together, or maybe it's we come down together and we ride up together in cases. That's the way we look at it. The single most important calling card other than our sourcing and our ability to underwrite is alignment. Every deal at Signal Peak has that element that pervades it so that the lawyer is not going to just coast along. Not that they ever would, but with a pure hourly arrangement, we make sure everyone's got skin in the game. And that's a really important passage.

Mani's emphasis on alignment and skin in the game reminds me of my conversation with Joe Ahmad, who talked about how the willingness to take real risk, and share in the consequences, is what separates the best trial lawyers from everyone else. Listen to my episode with Joe Ahmad.

Khurram Naik: Yeah, that makes sense. You have skin in the game on both sides, in both directions. Going back to the single patent case you funded, do you look for other things to assess that? Is that coming in the context of a team that you funded civil matters with? Or you wouldn't try to think about how risky your risky bets get? For any risky bet, is there some mitigating factor, like how diverse is the portfolio, or is the portfolio a little more concentrated?

Mani Walia: I think I got all of your question, and if I didn't, you can ask me to add on to this. The factors that we look at that help us get comfortable with, for example, a very risky single patent case, which maybe very few if anyone else would do. IPR risk, as you know and some of your listeners know, invalidity, everything is very pronounced.

This is a good point for me to say everything that we do, that Lauren and I do at Signal Peak, at least from my perspective, I owe to Steve Susman. Steve Susman, the founder of Susman Godfrey, in my view, was the first commercial funder because he and his firm took commercial cases on a contingent fee way back in the 1980s. Not many firms did that. The reason I bring that up is our diligence model follows the learnings that I got from him. How lucky am I that I got to be at that firm and understand how they underwrite cases?

In regards to your question, a single patent case, yes that's a risky thing. But how does venue look? How do damages look? Who are the experts going to be? How long till trial? How strong is the case, and what's the settlement history of that defendant? If you just look even at these five pillars I just mentioned, if all of those are strong and out of the park, that might get you comfortable in a case. All that said, we funded single patent cases, but there's many that I passed up on because they don't have the other confluence of unicorn factors. But you can break down a case, if you think of it in investment terms, into five or six compartments, give each part a score, and homogenize your overall portfolio. And that's what we do.

Khurram Naik: So going back to Steve Susman's investment methodology, how does your approach differ from what Steve had?

Mani Walia: Susman's principles, we've just built on it. Obviously I'm biased. Steve is like a legend to me, a mentor. And many people listening to a podcast may feel that way. But I want to give credit to the way I worked there, and I think very highly of them. We've just built on it because things have changed in the last 15 years where he wrote this diligence memo and we emulated it.

Here are some examples. We now have data on lawyers. You could say, tell me about Joe Smith at Firm X, what's his win-loss record. And I have that data. So one big difference from the Steve Susman era is they never had to underwrite the lawyer, right? Because they're litigating the cases themselves. When I was there and we got a case approved to take on a contingent basis, we knew we were litigating it and we believed in the capability of the lawyers at the firm. Now when I underwrite in this seat as a funder, I spend a lot of time on what's the win-loss percentage of the lawyer, what's his or her integrity, what are other cases that person has handled. So that's a big part of our analysis.

And the other big part is now there's so much publicly available information, plus stuff from our database on cases we passed on, that you could say, hey, tell me about McDonald's, how many cases has it settled, what's its track record. And that's important to us. We don't want to always fund cases against litigants or defendants who will go to the end of the world to take you to trial. So those are two differentiating things: assessing the lawyer and having stats on reliability of settlement from defendants.

Khurram Naik: With that data approach, I'm curious about how you make inferences about the future. Let's say in the realm of patents, you're funding a lot of patent cases. You mentioned IPRs. There's a lot of challenges with getting IPRs instituted right now, and so there's a lot of uncertainty about the PTAB as a forum. What are the consequences of that? A pretty straightforward inference draws that we'll see more disputes in district court litigation. How do you think about that? I am normally reticent to make predictions because I know there's lots of ironic consequences to actions. But as a legal recruiter focusing on patent litigation, I'm making a bet that firms will continue to thrive and need legal recruiters, that there's opacity in that market requiring trust and expertise. And also on patent litigation itself, that patent litigation will remain durable and evergreen. So I'm curious, data-driven or otherwise, how do you think about the future of your fund? How do you think about what comes in line for patent litigation?

Mani Walia: We think about it in an organized way. Every month or so at our company, we get out of the daily grind and how busy we are on daily intake and sourcing and underwriting, and we just sit around and think about macro issues that are out there. And one of the macro issues is, where do we see trends, where do we see things closing up, and how can we best optimize ourselves to take advantage of that?

Let's use the patent area as you brought it up. We take a spin on Bezos's line. We sort of have 95% of the information and we're at an informational seat of power before we underwrite the case. We know the lawyer's track record, we know the defendant's history of settling, we know what the claim charts look like, et cetera. So we have a lot of information. We don't have a crystal ball on the future, but what we do is we pull the trigger based on a reasonable assessment of where things are going down the line.

The biggest concern for us these days is regulation of litigation finance. One thing to think about in stark terms is, if we fund this patent case, in three years will the court require review of our documents? Will someone say patent litigation funding is not appropriate or not something that should happen? So what we do is the best we can. Our company participates in ILFA, which is a lobbying organization. We're having an event in February. We have a member of Congress coming in, another congressional candidate. So we do our best being in the know about these things. And if we hear that, gosh, in three years there's this thing in this bill in Congress that can really impact us, that might slow us down a little bit. But on that stuff, maybe just like how you're feeling in your business, you can do the best you can and be confident with your underwriting now, have a reasonable view of the future, and go, because if you get paralyzed with what might come about, it'll detract from the short-term success of that particular case or this round of cases.

Khurram Naik: Can we go back to what you learned from Susman and Steve Susman? When I think about Susman in the market, people think about the process for litigating cases, the patterns, the culture, the ethical culture, and assessing outcomes. And Mani, you may be aware of this, but I did some research on Susman's website today. There's still a list of letters of recommendation for the firm, and you're in there. This is from, I'm not sure if it has the date, Mirtha Cassambier. She had a glowing letter for you. It was addressed to you and Steve about your impact. And she had some things to say. I'll read off what she said about you: "I also need to tell you about how pleased I was with you, Mani. You did excellent work. You never let up, and your daily work was crucial to getting an unusually good result against a very difficult opponent. You were a pleasure to work with. You have excellent client service skills and answered all my questions promptly and as much as I needed. I felt throughout the case it was very well informed, which helped me to keep my focus and stay calm. You're a great credit to your firm. The opponent was used to pushing people around and having their way. It didn't happen here." Well, I guess now that I said that, we need to take a moment to zoom in on that and hear about that experience. Tell me about the posture of that matter, because clearly you left a very happy client.

Mani Walia: Thank you for bringing it up. That brought back good memories. And I think what's relevant for your audience and you is that was a case I litigated just with Steve Susman. So on some of these, on your ledger here of tell me about the things I've learned there, how amazing to be the single associate on a case with Steve Susman. You learn a lot from him in that regard, just watching him. Point two is I was lucky to be at a firm, Susman, where meaningful work flowed down. Lawyers like me, young baby associates or junior associates, got a chance. I think I argued the summary judgment in that case. I took some depositions. This doesn't really happen at a lot of firms because the partner-level lawyers are either tasked or keep the work. So that's part two.

And as far as this case specifically and this nice glowing letter that she wrote, which I hadn't thought of in so many years, that part is something that I'm lucky to have. I'm a communicative person by nature. I'm sure my wife and kids may say too communicative. But what that helps with is clients love updates. Clients love touch points. And that's something that we do in our business now. It's so interesting, and I'm so humbled to say this, our business now at Signal Peak follows so many of these little things that we've learned along the way. So we often give clients non-update updates, as we call them. Like, hey, we'll get you the term sheet in three days. And then we stick to it. People just like to know, in my opinion, where you are in the process, and that their matter is as important to the funder as it is to them. You might feel the same way when you have so many placements. People are wondering, am I going to hear an offer from these firms? If you give that little touch point, as long as it's honest obviously and there's some meaningful component of the information, it goes a long way.

I've addressed the micro of that case and a little bit of Steve Susman. The last thing I'll say about Steve and that firm is that's a tremendous display of trust. Steve Susman, best trial lawyer of his generation, letting me, a second-year associate, do most of the heavy lifting in that case. How amazing is that? He obviously had oversight, so if I started veering off course he could force-correct. But that's something you don't find at very many firms. Maybe now a little bit more, but back in those days, almost none as I can recall.

Khurram Naik: So going back to Susman, I think even just that little blurb hits on those three components: process, culture, and outcomes. So when you think about it, maybe there's other functions you have in mind, but which of those do you think is the dimension you are most emphasizing at Signal Peak?

Mani Walia: It's definitely the first two. Outcomes you can't control. I have all these quotes that I enjoy following. In the old days I used to read a lot of legal books, Supreme Court books. Now I read a lot of business books. But Steve Jobs has this great quote, I think he gave it at the commencement at Stanford some years ago. You can only, when you look back, you've got to trust your gut and move forward and hope you're making successful outcomes. But when you look back, you'll be able to connect the dots on how you did it. So for me, process is the most important thing, because if you're doing things right, then you have to assume that some of the outcomes will be successful. So we're big believers. It's Lawrence's phrase, but what you put out in your community comes back to you. So we think the same way about our process. We have a very detailed, rigorous process on underwriting that comes from some of the Steve Susman guidelines. We don't cut corners there. And when you follow that process and you have the benefit of great sourcing, you end up being in great trades or great investments. And therefore, outcomes hopefully will justify the process. But to me, outcomes is something we don't think about. It's the other two that we focus on.

Khurram Naik: And for underwriting, I know the discussion mentions that you are tracking things. There are the standard things for underwriting: what's the damages case, what's the likelihood of prevailing, you're working backwards to the collectibility. You're working backwards from that. There are somewhat standardized principles you're using. Do you think within underwriting there's some dimension you have a competitive advantage? Maybe it's assessing likelihood of prevailing, based on your trial experience. That's my best guess for what your advantage would be in underwriting. But is there some dimension in underwriting you feel that your team is particularly strong at?

Mani Walia: Yes, I do. And it flows back to macro principles. Put yourself in the trial lawyer's shoes. You can naturally play that part. When a trial lawyer is looking to have his client get funded and goes out to two or three funders, speed is a great currency, because lawsuits are depreciating assets. You want to get it on file. Plus there's an emotional moment. The plaintiff has been waiting around, law firms were waiting around. Let's get it going. We know exactly what that feeling is because we were there.

And here's what we do substantively. We have organized our business at Signal Peak to fund cases that Lauren and I know, that we used to litigate. Lauren clerked for two federal judges. I told you she was a partner in a blue-chip Texas firm. I clerked for two federal judges. We know how to try those types of cases, the ones that we fund. So here's what we know in underwriting: we exercise so much speed that we get to term sheet and finality while other funders may still be hiring somebody to underwrite, because we do so much underwriting ourselves. We just happen to move faster. So that's one tangible aspect of our underwriting, we do it ourselves for the most part, which does put a lot of work on us, which is why we limit the things we fund to things that we litigated before.

If you give me a patent case and five claim charts, I can go through it pretty quickly because I speak that language. You won't find us funding injury cases or international arbitration disputes with foreign countries. I just don't know that area, neither does Lauren. So that's how we cultivate an underwriting advantage, going off from what we know trial lawyers and their clients want, which is, come on, get me an answer. We beat a lot of our competitors on pure speed. Obviously you can't just shortcut and be like, yes, this looks like a good case or it doesn't. You need to have the horsepower internally to be able to do it. And we're lucky in that regard.

Khurram Naik: And I think speed also ties to your principle earlier of the Jeff Bezos concept of making decisions with 70% of information. My first question is that speed is, I think for a number of litigators, for lawyers, a bit of a challenge in that they're used to really thinking things through, careful creativity, and accustomed to whenever possible having the time to really think something through, make a thorough analysis. Is there something that you're doing at Signal Peak that is operationalizing aspects of sourcing, underwriting, etc., to make it easier to get through this process and make decisions? How are you able to achieve speed through operations?

Mani Walia: We use the screening process and tools that we have developed from our own database and publicly available sources to filter cases quickly. So this helps us with speed. Let's say in any given month, we're looking at 50 cases. Maybe half can be filtered out without us using any human capital. For example, we have a formula on, well, if the best-case damages here are a certain amount, and people don't come to us for those types of cases, we screen out just by putting it into our system, our financial system of, does this case even meet the sort of financial type of big-stakes cases that we're looking for. So that's one way we do it, which is by the model and filtering out.

We also employ checks and balances at our firm, which does help with speed. Lauren and I, we think that we have proficiency on most complicated types of business litigation that's out there. Our colleague Jackson, someone I used to work with at my previous company, he basically runs the financial analysis in parallel path. So back to speed, if we need to tell someone we're going to fund their case, we can't just fund a meritorious case. It's got to also have enough return for everybody. He's doing that in parallel path, and that helps us with our underwriting speed.

Khurram Naik: So going back to your partnership, how did you come to, you mentioned that you were competitors, how did you come to decide you should partner together? How do you choose partners in this work, or generally? What are the principles you use to determine who would make a good partner?

Mani Walia: I've never answered that question. And it sounds almost like something out of a Disney story or something. I only had thoughts of ever partnering with one person after I left my previous company, and it was Lauren Harrison. There's many prongs, it's not as simple as that. But she fit everything that I could possibly want to have in a partnership.

Number one, I admired her work. Number two, I knew she's a person of very high integrity. She was a funder in the community, so I knew all this about her reputation. We had worked together before, putting on panels at conferences, so we had a working relationship.

Number three, there's a personal connection that's very unique. Her husband, Jeff Harrison, at Susman, a larger-than-life, phenomenally successful trial lawyer, was basically someone I looked up to at Susman. I went to trial with him. So I knew of Lauren through him. And I thought so highly of Jeff. Like, that letter that you had of Dr. Cassambier, if Jeff ever wrote anything nice about me at the firm, I'd print it out and put it in my office. That's how highly I thought of him. As you're coming up at law firms, you look up to these partners.

And then putting on my business hat, which has really developed over the last five to seven years, it made so much sense to partner with Lauren in this sourcing world, this alpha world of top trial lawyers wanting to work with you. If you're a top trial lawyer, there's no one more top than Lauren. She is in many respects a leader in leadership groups down here in Texas. People look up to her. Parenthetically, my wife used to practice law at the firm Lauren was at, Vinson & Elkins in Houston. And she also looked up to Lauren. And although they weren't in the same practice area, Lauren would give speeches to young associates all the time. So basically that was the confluence of factors. There was no one else that has all of those qualities, and she fits our Texas trial lawyer theme. It was just a perfect fit. I'm so thrilled that she agreed to join. She's not at a point where she may need to work, but it was just such a great thing to be able to join up with her.

Mani's thoughtfulness about choosing a partner with complementary strengths and shared values echoes what Rakesh Kilaru shared about building Longford Capital, where finding the right co-founder with aligned instincts was just as important as the fund's investment thesis. Check out my episode with Rakesh Kilaru.

Khurram Naik: Is there anything special about how you, in the context of law firms, clients, and funders, there's that triangle where alignment is important. Is there anything unique you think you're doing in your fund around alignment that is effective?

Mani Walia: Yes. In our fund, it all comes full circle because most of the cases have unique alignment. Let's just use a clear example. We're not funding a lawyer at a hundred percent of his or her hourly lodestar, because if you think about it, what's the incentive for this lawyer to get things settled? You've got to have more of a stark alignment with the lawyer. Because we find that on a deal-by-deal basis, our fund is unique insofar as we present a batch of these very aligned cases, which is just hard to find.

Without going too far down the rabbit trail, nine of the top 20 litigation-only firms are in the state of Texas. That's because Susman Godfrey started here in 1980, and there's a whole list of others that you might know on that big list. AZA is on there, that I know you're familiar with. Gibbs and Bruns, another great Texas firm. I'm not suggesting we work with all these firms, but what I am suggesting is because all those firms exist here in Texas and a lot of them in Houston, we have access to these firms who believe in alignment a little bit more than a standard big firm that generally makes its money on an hourly lodestar. Because of that, we source a big portfolio of those. And one of our fund's calling cards is investors will note, gosh, your deals have such alignment with the lawyer that it makes it very captivating for them to see that type of alignment.

Khurram Naik: My question is, say with you and Lauren and with your investors, is there nothing that you think is novel? Can you describe the first principles you're using for how you align that team and those investors?

Mani Walia: Maybe one thing that's novel about the alignment is we on purpose structure our fund to be, relative to our peer group, smaller. And part of the marketing of that is investors recognize that we don't have the pressure to stuff cases in just to hit our minimum target. We'd rather do these smaller funds more often and not have the pressure of having to keep it going so long to find less attractive cases. So that may be one alignment calling card.

The reason we're able to do that is we source so quickly that by the time we close a fund, we already have 75% of the cases ready to put into it. And then onto the next. So it's a very rinse-and-repeat, continuous process. And maybe by comparison, some larger funds may not have that alignment because, let's say they've raised a billion dollars and they take their management fee, maybe the LPs are thinking, well, the cases are bad, what does the manager really care? They're already making a terrific return off of the management fee. I'm not saying there's a clear example I have in mind, and I presume no one in industry acts that way. But you can think how investors may think about it. They'd rather see a small fund where you're not getting wealthy off the management fee, but you've got a real incentive to make sure you picked well in your 20, 30, 40 cases in your fund.

Khurram Naik: Are there any properties you're looking for in investors?

Mani Walia: Part of the charm, and I feel tremendously lucky to now co-lead this company with Lauren, I've gone from associate at a law firm, albeit the best in the country, putting on a pure legal hat, to being able to say, how many people get to be in the position I'm in. Part of it is because our anchor investor is someone I used to work with when I was at my previous company. I've been around with them for several cycles. I'd love to have a repeat investor base of people who are like-minded.

Here's an example. We love university endowments. When you make money for a university endowment, where does that money go? It helps pay scholarships for academic need, or for people who may not be able to go to that school without the return you're delivering. How fulfilling is that? In my world, I can help a plaintiff access great lawyers and take on big tech companies, and make money that he or she then uses for their business. Or in one example I had from my past, someone built a family foundation for future tech entrepreneurs. How amazing and fulfilling is that work? And if you can pair it with LPs who are doing the right things and serving good causes, it's amazing.

So basically we look for repeat LPs. If we can be choosy, and it's not always the case that someone can be choosy, I prefer our LPs not to be just professional money managers on Wall Street. I would prefer them to have a mission that resonates with us. Because all of the work that we're so lucky to do fits this nice circle. I don't make any mistake or sound cookie-cutter about it. Returns are important and we couldn't do this business without making returns. But you could make returns and make an impact at the same time.

Khurram Naik: So let's go back. You talked really early on about your training from Susman. You're advocating for more litigators to become entrepreneurs. And you're saying that lawyers are especially good at going through task sheets. Tell me more about that concept and how you implement that today. Let's get into brass tacks. How do you organize tasks you work on and get through them? Because I think operations are a very under-discussed aspect in law and business generally. I have noticed that two out of the three federal judges I've interviewed had both talked about process and case management as being highly underrated. So I'm curious to hear about how you think about the operations by way of this concept of being a task sheet leader.

Mani Walia: The task sheet leader is something I think I just coined. So if it sounds hokey, you can blame it on me. I think it resonates for me personally, and I wonder, and you may have a better sense of this, I bet it applies for a lot of lawyers. If some folks are listening to this and thinking, gosh, should I take a step and do something that's out there that I thought about, but it's risky, we have a really good skill set.

I love the quote, I think it's Edison: vision without execution is hallucination. And at my old firm, people would look to me for coming up with processes. And that's where I thought about this task sheet leader mentality. I think it's tremendously beneficial. Operations does get stuff done. Yes, you have to have some idea, come up with 10 ideas and pick one or two or three that work. But then you can't get anywhere without being extremely, almost obsessed, with the process and setting up an organized structure.

Here are things that we do, and again a lot of this I was lucky to learn from Steve Susman. We keep a master task sheet at our firm with all tasks that need to be done, and we have a weekly call to discuss it. Again, this is a practice I learned at Susman. And something we do, it keeps everyone organized on a weekly basis.

Another process that we use: I've never liked it when someone says on email, oh, this would be a good idea to capture and we can do it, and it just dives into a black hole. So something else I've said to folks is, let's not let any idea fall into a black hole. We have someone on our team who is specifically charged, she's a paralegal by training, and she's so organized. She makes sure to capture those stray things and put them on our monthly agenda. For what I talked about earlier, once a month we get together with a cup of coffee or a figurine or maybe people should have a glass of wine, and we just sit and talk slowly and think about, this was an idea someone raised on email, should we actually put it on our daily and weekly list and have someone assigned to do it?

Another principle: one riot, one ranger. It's another Steve Susman principle. Every task that's on our task sheet has one assigned person to do it. I've recognized, and again I owe this to Susman, you don't need five people doing one task. Then you get the tragedy of the commons. No one knows who's doing it. You assign one person and their job is to come back and say on the next weekly call, this task is done. If you're curious about the process, here's how it went. So those are some daily things.

And the last thing I'll say about this, using my own example, starting this new company with Lauren, we had a master overarching, like an omnibus timeline where we said, January 1st, pick a name. January 15th, office space. If you give yourself deadlines, which forces you to be organized, then you've got to hit them. Because lawyers are good at that. Most lawyers I know, when the court says your brief's due, that brief is going to be in.

So that's what I found. And not a lot of this is probably written in Harvard Business School stuff because it's so intuitive. It's so intangible. But forcing yourself to have a task sheet, forcing yourself to have this monthly loose-goosey ideas generation where you can talk about new ideas and help steer the ship, don't let ideas fall into the black hole, make sure one single person is accountable for certain tasks. They have done wonders for me. And I owe so much credit to people who I've formulated these ideas from. They guide our firm. We get a tremendous amount done with our small, lean team because we're very clear about the tasks.

Khurram Naik: How much wiggle room do you have? When you raise a fund, you're telling your investors you're committed to doing certain kinds of things. There's a wheelhouse you're going to stay in. There are certain kinds of assets you can acquire. There are some guidelines for how you're approaching, and hopefully there's some creativity as well. Something I've observed about my business, it's two and a half years old, is that we're often redirecting and pivoting and saying, okay, now we have this new data. You're talking about data before. And it's like, we have these new insights from our performance, from our outcomes, proprietary information that leads us to some new insight for how the business should be directed. For instance, this past year, I had 15 placements. It had been repeat litigators. And so the signal from the market is very clear, this is the value you're generating, this is your alpha. And so that's something we use, that data, to say that's going to be our focus for at least the next year or so, potentially indefinitely. So how do you use data insights from your performance or new ideas coming up from first principles? I know it's a much-abused phrase these days, but how do you use that to shape your direction? What has changed in your business since inception, and does that give us a clue for what could change in a year's time?

Mani Walia: One thing that changed from inception is we found value in cases from a source that we didn't contemplate before. I'll give one example. There are sometimes claims out of bankruptcy that I never thought that we would find to be potentially compelling to put in the fund.

And so here's our process on melding first principles with having the flexibility to do so. We're not a public company. We're a private company. Our mandate is defined in the fund documents of what we can do. One of our first principles was, although we're super focused, you could probably get a feel of how focused we are following cases that we've litigated or the kind of cases we fund, but our documents allow us to be anywhere in the commercial litigation space. We have no idea, no incentive, and no background to ever get into mass torts and that kind of stuff. But we're allowed to get anywhere we want in the commercial litigation sector. We choose to be in the specific ones that allow us to go fast and all the stuff I talked about for the sourcing advantage.

But here's how we do it. Every month we sit around and we say, what are the trends we're seeing? And someone may say, listen, we're starting to see tremendous value in the international arbitration space. And then what I'll do is assign someone at that meeting, say, write a short memo on this. Because the monthly meetings, we use as a way to steer the ship. You can't really change things on a daily basis when you're just so in the grind. And frankly, maybe we could do it every quarter, or at least once a year, but we do it every month. Everyone on the team, we tell them, this is a chance to steer the ship in a different way.

So let's go down this hypothetical. Let's say someone says, I'm seeing tremendous value in potential international arbitrations or patent cases in Germany. Then we test that person with making sure it's not just something that's going to be said and fall into the black hole. A short memo, convince us. And if we are so moved by it, then in the next iteration of the fund, our funds go very fast, we can broaden the language and change.

So that's hopefully as real an example as I can give where you see everything coming together. I have never experienced someone on a weekly call accomplishing his or her task coming up with a great idea that changes things right then and there. You have to sort of pressure-test it in the weekly or monthly setting and then make sure we've got group momentum. And then we're able to change the way the ship is steered.

Khurram Naik: Are there any metrics you're measuring on a quarterly or monthly basis?

Mani Walia: We do measure our intake. Intake means possible cases we can fund. I spent so much time earlier talking about sourcing, so that is something that we follow and track. And here's an example. If we ever noticed that our sourcing was dropping, and this is a counterfactual example, but because of all of our processes, we have a monthly check-in, someone would say, here's our sourcing for the last three months. And let's just say, counterfactual example, we're down to three cases we've sourced in the last month or something ridiculous like that. We would immediately say, okay, this warrants a deep-dive discussion. Let's put it on the calendar, and everyone come up with some ideas on his or her own. Let's have another slot, come up with the five best ideas and start improving.

Because we're so lean and because we're so organized, if I can say that about ourselves, we get things done pretty quickly. We're a nimble operation. And going back, that's also a very important part of our sourcing. Because we're nimble, when we have cases where we know there's value, and the trial lawyer says, it's important to me that the client has some money for this or that, we're so nimble we can decide almost on the spot or within a quick ad hoc meeting and get back to people.

Khurram Naik: What's the tech stack that your business runs on?

Mani Walia: We have a platform where we centralize everything. It's not deep tech, but basically we have a platform where we have a collection or reservoir of every case we've ever looked at, what's the status of that case. We automatically track that case. So let's say there's a case, most of the cases that come to us we pass on, but our tech allows us to follow that case. And that way, if we see that it actually did achieve something or we were wrong about some risky facet of the case that never materialized, we can course-correct. And then again, going back to the holistic approach, we would course-correct at a monthly meeting where someone on our team is responsible for saying, here's two cases we passed on, here's how they're doing.

And then we're humble enough to be like, man, here's a lesson learned on that. That's another thing I learned from Steve Susman. We do lessons learned after each investment. Go to our bad, right? Sometimes you want to just pat yourself on the back, but there's still something to learn. It's like, keep refining your skill set. If LeBron can keep practicing after all these years, we certainly can learn from how we've passed on cases and how they've done, and what cases we've had success on.

This discipline of doing honest post-mortems and learning from both wins and losses is something Priyanka Timblo also emphasized when she described how reflecting on outcomes shaped her approach to complex litigation. Listen to my conversation with Priyanka Timblo.

Khurram Naik: Can you share a specific insight? I think there's probably multiple components that go into it. There's the prevailing itself, all the things you talk about in diligencing, the damages, how you prevail, all the different components. But there's also the intangibles of assessing the team and other criteria there. So what, was there some recent pattern you'd identified in the matters that you passed on that had some beneficial outcome? What were the types of beneficial outcomes as a pattern, and what was the insight you generated from that pattern?

Mani Walia: Yes, two examples. One, there was a moment in time where I allowed myself to get shortsighted on IPR, inter partes review. For those who are not as focused on it, it's an administrative tool that the US Patent and Trademark Office has. It was underutilized or not utilized while I was in practice 10, 12 years ago. But then all of a sudden it came back on expiring patents as a very powerful tool for defendants.

To answer your question, we passed on some cases where I thought, gosh, I've been recently biased. We just had a string of bad luck on IPR cases. Let's pass. When we went back and holistically looked, it really was prisoner of the moment, short-term thinking. But because we have these processes where we're accountable to each other, we track and we can come back and say how are things going holistically, we course-corrected and gave IPR its appropriate, not over-the-top, weight in our factor analysis.

The other example, something we've learned, is I never used to underwrite whether the lead lawyer is going to retire. We've always underwritten, like, let's say we're going to do a case with Joe Schmo at Quinn, but we heard that Joe Schmo may go to Boies Schiller. Do we like the rest of the bench at Quinn? I'm making all this up. But I'd never really thought of, well, what if Joe Schmo retires? And that's a big difference. When you have these cases that may go to trial, the lead lawyer often has the perfect blend of moxie and charisma. Not to say other lawyers on the team don't, but maybe it's something that's worth analysis. So that's something else we've course-corrected in a positive way. We had an experience that was positive, and then we realized we need to really analyze that. Going back to the holistic approach, we now have that as part of our underwriting analysis. I talked about the five big pillars: damages, legal merits, collectibility, financial analysis, duration. And some of those have prongs, and one of the prongs when we look at the lawyer is, are they about to retire? Someone's 64 and the firm requires retirement at 65, think about it.

Khurram Naik: What are some common reasons you pass on a case?

Mani Walia: On the surface, oftentimes, I'm trying to do this for our patent audience here, venue and damages. I know I'll give you two. Oftentimes a great-looking case, great lawyers, strong infringement charts, prior art search comes back and there's not much likely stuff out there, defendant is someone you know is collectible, but the venue puts you in, I'm making this up, the Southern District of New York or the Northern District of California, and you're really worried about how long the judge will take or if you might get tossed on summary judgment even though you don't think it should be. Sometimes the whims of the judges, particularly in districts that are not really patent-friendly, can really alter a case. So I would say the biggest reason that we have turned down otherwise perfect-looking cases or unicorn-looking cases is venue is just very challenging. That's a function of recency bias. 10 years ago, pre-TC Heartland, none of us had to worry about that as much. You may not have ever thought about it. Back in my day, you could sue five defendants in the Eastern District of Texas in the same case.

Number two is damages. The Federal Circuit, to be very specific here with your audience, has just made it, it seems, more challenging to get big damage awards approved or affirmed. So this is like a first-world issue to say this, but it comes from our monthly meetings. We sometimes will pass on cases where the damages are too high. Talk about what a weird counterintuitive thing that is to say. But you've got to think, is it settleable? Sometimes defendants will say, look, I'm not going to settle this thing because I'll win at the Federal Circuit. We have passed on that, and surprisingly it's probably the second big area of us passing. People may think, my goodness, what kind of first-world issue is that, but it really is an issue. A judgment is just a piece of paper. You've got to get it affirmed or got to get it settled. So those are two areas, and it all is holistic. It's part of our underwriting now.

Khurram Naik: That's super interesting. Then also on underwriting, I'm not sure if you can say it's a post-underwriting function, but choosing counsel or working with counsel. How do you think about that? Because you mentioned a lot of big brand names, Susman, Quinn, and Boies Schiller. Are you betting on those platforms? Are you betting on up-and-comers? I've seen other funders that I think favor working with up-and-comers, then having repeat work and flows there and iterating. How do you think about large, set-with-platform particular experience versus up-and-comers?

Mani Walia: We're really, I know we have been throwing out these examples, and the Quinn and Boies, I just threw them out. No active cases. It's just easy for people to follow along because everyone knows those names. We're agnostic. So much of the benefit of what we do is the people and this virtuous cycle. Again, the LPs that we like are repeat LPs, have a mission. The deal flow that we do is a lot of repeat. But about 10% of our cases come to us without counsel. It's a more recent phenomenon.

So therefore, it comes on us, Signal Peak, to match it up with the right lawyers. Just from very recent stuff, in the last few weeks, I've sent matters to a very small firm in New York that happened to be the right fit in my view for that case because it was the right technology, and it's a small spinoff where I know some guy I used to go to law school with or was on law review with. So again, it goes back to trust and relationships and networking. He's a great guy and he's a great lawyer. That firm seemed to be the right fit for that case.

I've had cases where it comes in without lawyers and it happened to be the perfect fit for a huge AmLaw firm because they have a person there who's done this type of case often. So I'm kind of agnostic about premier brand versus up-and-comers. Oftentimes you can find amazing alignment from up-and-comers, so there might be a little sort of thumb on the scale for that as well, because they don't have such a high overhead where they need to say, we need to be paid by the hour.

Khurram Naik: And then how do you think about, so you're making a concentrated bet that you are focusing on patent litigation. Within that domain, how do you think about the bets you're making? Are you looking to have uncorrelated bets, or are you looking to have concentration? Like, maybe you're saying, I'm really bullish on a particular kind of technology, or I'm really trying to do these kinds of competitive disputes. Within that domain, you've got a wheelhouse of patent litigation, that's a concentrated bet of some kind. Within that domain, are you further concentrating or diversifying? How do you think about that?

Mani Walia: Maybe a little bit of both. And here's what I mean. Back to our macro, at our monthly meeting, we also have a little bit of time where we look at the portfolio. We have guidelines for the portfolio. One thing to just note and correct is we don't exclusively do patent cases. I've just been bringing it up because it resonates with your audience and you and me, and we are both patent lawyers. But our mandate is broader. And even if I wanted to do all patents, I think that would be too concentrated because there are tremendous value cases in other areas as well.

Going back to this, we have macro principles on what's our aspirational sort of number, like percent of the portfolio. Do we want 10 percent patent cases, do we want 60, do we want 90, do we want 20? And the way we do that is at these monthly meetings, before we launch a fund, we're aspirational. We list it out based on all the things we've learned.

Then on the deal-by-deal basis, within a subsector, let's use patent, I try to follow the principle of using kind of a sports analogy, like if an NFL team is drafting or an NBA team is drafting, sometimes they don't draft for need, they just draft the best player available. We do the same thing. Whether we funded three straight semiconductor cases, I'm agnostic to that when the fourth one comes up that happens to be the best for that time. So on a very deal-by-deal basis, we're not looking across technology and capping ourselves saying, oh, we just did two semiconductor cases, we're out. Because I think that would cause us to pass on tremendous value cases, kind of the inverse of that IPR example where I was like, oh gosh, IPR risk bit us twice, let's not do it a third time. I think that's shortsighted because it doesn't affect the overall portfolio in terms of concentration.

Khurram Naik: You're finding and learning as you progress. So if you could, is there anything you would do differently about launching the business with the insights that you have now?

Mani Walia: I'm pausing on this one. This is so fun to be on your podcast because these questions may have roamed in my mind, but no one's ever asked me. This sounds almost cocky, but the answer is no. And the reason for it being no is I did get to help start a business within a business while I was at my predecessor, my previous company. And so there probably were lessons there about team and focus that I did learn. But again, this is another attribute, I think, of risk-averse lawyers. Let's stipulate lawyers generally are risk-averse. Yes, we like task sheets. I feel like because I learned it once and I didn't want to go through it again and not learn the lesson, everything that we have done at Signal Peak has been by design to remedy some of the things that I didn't like from the past. So the answer to your question is no, I would do it the exact same way again. And I'm so lucky to say that, but it's because learnings happened earlier at forks in the career path.

Khurram Naik: What's the part of the business you think is going to grow the most this year?

Mani Walia: We are seeing tremendous demand for patent cases to get filed. I know this is a patent background for me and you, but it didn't mean to come out this way. It just sounds made for this podcast because the new head of the Patent and Trademark Office is not allowing IPR to be used in the way that it was before. There is great enthusiasm from patent holders. There have literally been conferences called "Return of the Patent Inventor." And we are just seeing everyone come out and say, this is the time, and they're trying to get lawyers. So there's tremendous enthusiasm there.

That doesn't mean all those cases are going to get filed. The system needs to weed out some cases. Some patent inventors may have something that should have been invalidated, or maybe damages need to grow a little bit. But there is, because of that great enthusiasm, we're seeing a lot more opportunities, which means we'll find more to put in our fund from that background.

Khurram Naik: So we're going to head into our final question here. You're a marathon runner. You run a lot, which is super hard, especially running a business. And you've got kids and a partner. So I guess one question is, how do you find time for all that? But then, what does it do for you? What do you think the impact of running is on you and your work?

Mani Walia: I hope my kids listen to this part because it is such an important part of my life. And I'll answer the question, but I'll note that Lauren is a competitive equestrian and she's a top placer in Texas. So we must have some shared DNA. Jackson, who I mentioned earlier, is a competitive weightlifter and he does competitions. So there's something in our DNA. And part of it, we always joke that some of our camaraderie, we feel very connected on so many levels.

Running is tremendously important for me. And I wonder if any young lawyer out there is thinking that he or she is too busy to find something. I hope you do. Because I've been running for a long time. I ran all growing up. I run all sorts of races. But on my everyday run, which will generally be early in the morning because of the demands of fatherhood and working, it is so good for my mental health and my work.

Here are real examples. I listen to a lot of business books, and you learn something by reading about people who've done it before, so you can emulate or grow. So I listen to a lot of books, that's reason number one. Number two, as I'm running, because lawyers are as you said type A, maybe risk-averse as I've said, maybe worry-ish, I find myself in my daily life magnifying blemishes or worrying too much. When I run, that goes out the window. And I can actually be like, gosh, I'm distilling these five work worries down to two, and here's my plan for these two. So many times during my run I will stop really quickly and stop my watch, since I time everything, and I have a little task sheet on my phone, one of these apps, and I will jot down something.

The third way is, if I'm not running super early in the morning, I will take internal work calls, most likely with Jackson. I don't think I would call anyone else. I certainly would never call a funder, lawyer, or an investor. But if I have some idea and he happens to be free, I'll call him and say, hey, what do you think about this? So I get a lot of ideas as I'm running. Incidentally, he's taken calls from me or he's made calls while he's been at the gym. So he must have the same kind of thing.

I do think that really helps. And obviously being in good physical shape, it's good for us as we get into this next season of our life to want to spend time with our kids. But I think running is more mental for me on the positives for work than it is even the physical stuff. My wife jokes that if I ever stop running, I'm going to turn into a big grouch.

Khurram Naik: Just in describing that with your team, that's tremendous alignment there for how you move, in the most literal sense, and think. And so I think that's remarkable that we've honed in on that. I think the dimension that was latent in all this is your network and how you built it, how you built people who keep wanting to come back. And I know based on previous conversations there's so much there. So I guess I'll have to wait for round two. I want to thank you so much for round one. This has been tremendous.

Mani Walia: And as I mentioned at the beginning, I look down at literally everyone you've interviewed. It's a great roster. So it's a testament to your own network. And I'm lucky to be part of this group. Thank you for spending so much time with me, not just today but in some of the preparation meetings as well.

In this conversation, Joe breaks down what separates persuasive advocates from “polished” advocates, and why the jury can sense the difference immediately. He shares specific stories (including a New Year’s Eve mistrial decision he’d never repeat) and practical techniques for dealing with bad facts, corporate narratives, and the emotional game of the courtroom.

Keep reading below for the full link to the episode and the full transcript of our conversation.

This connects to ideas I shared in Why I Prioritize Sleep and How I'm Improving It.

Top Insights

Below are the highlights of our conversation:

• The Necessity of Risk: Why being a great trial lawyer means being willing to lose, and why the “safety” of academia can actually hinder your ability to handle the unpredictable variables of a live trial.
• Authenticity Over Polish: Joe breaks down why juries are the ultimate “phony detectors” and explains how being centered and spontaneous builds far more credibility than a perfectly scripted, polished performance.
• Owning the “Bad Facts”: Strategic advice on why you should never ignore the weaknesses in your case, but instead frame them yourself to turn potential liabilities into winning themes.

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https://embed.podcasts.apple.com/us/podcast/045-joe-ahmad-on-sincerity-vs-polish-empathy-based/id1536579571?i=1000744348420

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Full Transcript

Khurram Naik: Joe, glad to have you on the podcast. I’ve been really curious about having you on because I’ve observed the efficacy of your trial law firm, and I’m really curious to hear about your experiences here.

Joe Ahmad: Yeah, definitely. You know, like I’ve said in the past, I think the first thing you need to be successful is to be able to take risks. I think that’s something that, unfortunately, is not something that a lot of lawyers are used to, right? Because most lawyers were academically successful. I mean, the people we hire are very academically successful. They went to the best law schools, got the best grades, and they’re used to the notion where if I study enough, if I really perfect the material, I will do well, right? You don’t typically get ambushed on an exam. You don’t have people trying to undermine you like you do in a trial. And you don’t have the kind of variables when you’re going through academia as you do in trial.

And so, by definition, there is always a risk factor. It could be a witness crumbles or throws you some kind of a surprise. A judge can make a surprise ruling. Opposing counsel can, like I said, ambush you. And the jury can do the strangest things. So the first thing you have to recognize is that by definition, trials are about risk. If you’re not willing to take risk, if you’re not willing to go to trial because you may in fact lose, then you really can’t try any cases other than the slam dunk winners, right? And a lot of those, of course, by definition, never make it into a dispute that goes to trial. And even if they do, you probably don’t need a great lawyer for that, because the facts do matter, and if it’s a slam dunk, you just don’t need a great advocate.

So by definition, if you’re a great trial lawyer, you’re trying cases where there is at least some risk, and that’s why you got hired. And that means you can always lose no matter how great of a job you do, no matter how well you’re prepared. That is always a factor and you have to move forward. The other thing is—and this is part of the risk profile, and I’ve noticed this talking to juries afterwards—I would win a case and a jury was split six-six, and one juror just happens to make mention of a fact which I didn’t, and most people wouldn’t think is significant, and that turns the jury.

I’ll tell you about another case I had. I was trying a case—I remember it was on New Year’s Eve night. We were waiting for the jury. Yes, believe it or not, the judge kept everybody there until late at night New Year’s Eve. I was thinking this is unbelievable. And the jury came back late at night and said they were deadlocked, could not reach what was required to be a unanimous verdict. They had one holdout. Now, I had noticed that the other side had been kind of sitting close to where the jury was deliberating. And I was a plaintiff at the time. Normally, in retrospect, I should have just taken a non-unanimous verdict all day, right? That’s what I should have done. I did not.

And come to find out, I thought maybe the other side, who was willing to do a seven-to-one verdict and they were on the defense, I thought, well, normally that would be something the defendant would not agree to. They’re sitting by the jury, there must be a reason. So I said no. Turns out it was seven-to-one in my favor. Could have had a jury verdict in my favor. Said no, mistrial was declared, we had to try the whole case over again, and guess what happens the next time? I lose. Unanimous verdict against me. So, you know, you can even tell essentially the same story to a different jury and get a different result.

So like I said, I mean, there’s going to be risk that is very difficult to control. There’s going to be different things. You get one jury looks at it one way, another jury looks at it differently. Unfortunately—and this was in federal court—you don’t get a whole lot of time in most federal courts to do a voir dire, as we say in Texas. So you may not have a great sense of what the jury is about, but it can make all the difference in the world and it is awfully, awfully tough to predict. Even a case with the very same facts, same lawyer, same judge, everything. A change of jury can change everything. Same thing with, you know, you’re trying two cases with similar facts, not the same facts, different lawyers, different juries, different locations. Well, you know, you can’t just try the same case. You’ve got to adjust to the new facts, maybe the different locale, maybe opposing counsel’s different style. We did not—and this is the physician reimbursement case—and we won the first one, lost the second.

Khurram Naik: So going back to you talking about risk and how you said, hey, you know, I wouldn’t necessarily do that today. I wouldn’t make the same decision to seek a retrial today. What is it that you’re doing to assess risk differently today than you did let’s say 10 years ago?

Joe Ahmad: Well, I think first of all, you know, you can kind of let fear and paranoia get the best of you, right? Sometimes, you know, it is your initial intuition. You know, it’s like the old saying, your first intuition on a test is your best. And sometimes through fear or paranoia, you can overthink things, and that can be your enemy. And so, you know, a lot of times I will go with my first intuition. I have found that helpful on jury selection, voir dire as well. Sometimes with people, I mean, there’s, you know, if you do get a full voir dire, there can be cryptic comments that you can take one way or the other, right? They may have nothing to do with anything, they may actually be good for you, they could be interpreted bad for you. And sometimes, you know, you just overthink it to death and you end up making the wrong decision because of just, you know, paranoia—this person looked at me kind of funny, etc. And then you’ll hear from somebody else, oh don’t worry about that, they treated the other lawyer the same way. So, you know, even when you can get more data, it’s not necessarily good for you. Don’t let common sense and regular judgment go. Hang on to that and don’t overthink. Don’t let paranoia and fear get the best of you.

Khurram Naik: Yeah, that gets to something we’ve talked about that I’ve been curious about. There’s different themes about how you approach jury trials. So one theme is authenticity. So I’m sure we’ll unpack that a little more about what it means to be authentic, what are the different components of it. And there’s also the aspect of taking on bad facts and not explaining them away, and likewise, I’m sure you’ll explain that. And I’m curious about, you know, when it comes to say with bad facts, it seems to me that you often know the bad facts in advance—maybe bad facts surface later on, but maybe often you know the bad facts in advance. And so your approach is to say okay, I know the ways juries think about certain issues, so I need to align this bad fact with how they think about this in order to make a persuasive case that they’ll relate to. So you mentioned just now when you’re in the courtroom, you don’t want to overthink things. And you also mentioned before this idea that a lot of people that are at your firm or other top trial lawyers, you know, they are very academically competent, very skilled, and they’re used to being right in an academic context and of course that’s much more controlled, right? Like you said, a test isn’t just going to pull the rug underneath you really, that’s not typically how it’s done. So that leads to the question of, well then, the thinking part of a trial lawyer’s work—is the thinking mostly done outside the courtroom or in the courtroom? Like how do you think about the role of thinking, strategy, legal reasoning—when and where does that play out in the course of a trial lawyer’s work?

Joe Ahmad: Well, there’s lots to unpack there. Let me start off with just answering that last question. I think most of the thinking occurs outside of the courthouse, right? Yeah, you’re going to have to think on your feet during a trial, absolutely positively. But I think the real thinking goes on outside of the courthouse before trial ever begins, right? You have to come up with a theme, a framework of your case. And you know, keep in mind when I say don’t overthink things, you know, what I really mean is don’t overthink things for the wrong reason such as fear and paranoia, right?

When we talk about bad facts, I think a lot of people have the view that they’re afraid of the bad facts so they don’t want to talk about them, right? I’ve heard some people say, well, this is, you know, we’ve got our talking points, they’ve got their talking points and we’re going to go out there and throw them out there and our talking points are better than their talking points so we should win, right? But that’s not the way it works, unfortunately. The jury’s going to hear the bad facts and if you can’t come up with a theme that deals with the bad facts, then you’re going to lose in my opinion. If the jury is going to believe a fact which contradicts your theme, then by definition you cannot win. Right? And I think sometimes we forget that.

And by the way, I’ll say this, a lot of what I’ve learned is not just trying cases which, you know, I’ve tried over 100, but through reading on tools of persuasion, trial lawyers in the past. There really isn’t a lot of—I’ll be candid—I don’t know that there’s a lot of new thought out there in terms of advocacy. There might be some trends, you know, we have the “Reptile Theory” which I could talk about later. But a lot of the great advocacy has been taught for hundreds if not thousands of years. So a lot of what I talk about is really plagiarizing what people in the past have talked about.

But I think one of the things that you’ll hear from I think some great trial lawyers and some great trial teachers is, you know, find a way to make the bad fact at least work with your theme, right? So you want to talk about the bad facts. You don’t want to ignore them. And that is something that people don’t do because they’re afraid to, right? They don’t like it. It’s not comfortable. So the greatest thing you can do is thinking before a trial of a way to make that bad fact work for you. That’s ideal, okay? That is at the top of the pinnacle. Turn around that bad fact and make it work for you. Now, this goes a lot easier, one, if you can find a way for it to work for you, but also if you’re going first, right? If you’re going first and you can open first and your first introduction—the jury’s first introduction in fact to that bad fact is how you frame it—that’s an incredible advantage. And a lot of times you can do it on the defense, but it’s so much easier if you’re framing it for the first time for the jury to hear you, right? Because if it’s something the jury first hears from your mouth because you’re on the plaintiff’s side, you’re going first, and you make it work for your case, it doesn’t sound like a weakness.

Khurram Naik: What’s a time you did that?

Joe’s philosophy that trials are a risk sport reminded me of Priyanka Timblo, who left the safety of Paul Weiss for a five-year-old litigation boutique — and went on to win a $101 million verdict against Walmart.

Joe Ahmad: Well, I did this in, you know, many years ago we did a lot of harassment trials, sexual harassment trials for example. And in one case, the victim bought the harasser an expensive gift, a few thousand dollars, right? That was something that the defense couldn’t wait to mention. Except they went second. We went first. And you know, I had asked the client, and hadn’t really thought about it, but had asked the client, you know, why did you do this? And you know, the client had told me, well, you know, the harasser had given me a certain opportunity that paid me extra, a stipend, and it was worth a few thousand dollars.

You know, I think a lot of lawyers might have just kind of ignored that and not made that part of the case. But in this case, what I decided to do was make the gift work for us by telling the jury first that—go through all the harassment and tell the jury—as part of the harassment, the harasser would do certain favors which had a financial benefit, you know, basically as to pay for certain sexual or romantic favors, right? And as part of that, I said that this was so unwelcome that the victim actually went out right after this happened and bought an expensive gift for the harasser, costing about the same amount of money to say to the harasser, we are even, I don’t owe you anything, you can’t use this against me. So you can imagine when the other side gets up there and tries to use that fact, it has much less effect, if any, than it would have if we had not mentioned it. And we had a lot of other things to mention, of course. There was a lot of good evidence of harassment which certainly helped, right? And so in the context of all of that, we were able to make that work and win.

But you can’t do that, like I said, you can’t ignore something that the other side is going to basically try to bludgeon you with by simply ignoring it. You know, and I’ve heard lawyers say, well, you know, that’s their issue, okay, you know, we shouldn’t be talking about their issue. Going back to the talking points thing—we gotta talk about our talking points, never talk about their talking points. Does not work that way. Maybe it works that way in a debate; it does not work that way in trials.

Khurram Naik: You know, it’s interesting because I think another theme that I’m starting to pick up on is fear. So the emotional game of trial work. And so fear of loss is what leads to—you had shared before that there’s any number of trial lawyers who like to say, hey you know, I’ve never lost a trial. Well that’s because you’re really being very selective about the matters you take to trial and it shows that you’re not really taking the risks that you should be taking on, right? It’s kind of like Bernie Madoff—his returns are very stable month over month and people who had a lot of experience in finance said, hey that’s not how returns work, that’s just not real. So fear maybe is what leads people—fear of loss, fear of looking like you don’t know what you’re doing—might lead people to do that; they can’t take a punch. So another theme that you’ve shared that you know I’m hoping we’ll talk a little more about is authenticity, and you know, being authentic to jurors because juries—our legal system is that fact finders are assessing credibility. And so we have this intuition that if you take a handful of people and pool their judgment, they’re good at sizing up credibility in people. It’s just something intuitive like you were saying that you use when you’re sizing up jurors’ reactions. So it strikes me there might be a connection between fear, emotions, and authenticity. So if you are being authentic in how you present yourself, how you present your client, you’re way less likely to act out of fear because you’re centered and you’re balanced. I wonder is that a connection that you’ve drawn?

Joe Ahmad: Yeah, I mean I think clearly, right, the ability to be authentic is linked to having less fear, right? I think a lot of, for example, when I was a young lawyer, I couldn’t really be authentic because I was too afraid that if I was authentic, I would look like an idiot, right? You know? And so I would mimic the styles of other people who looked like they knew what they were doing, they were great trial lawyers, so I just adopted their style because I didn’t know, for example, that if I kind of let the jury see who I was, that they might think, well, you know, who is this idiot?

And you know, what’s interesting about this is, you know, it kind of goes back to the old, you know, textbooks on advocacy, right? I mean, you know, there is Plato’s Ethos, Logos, and Pathos. Well everybody likes to talk about Pathos and Logos—emotional appeal and logical appeal. Ethos is where the authenticity comes in a lot of times. I mean, it’s not just that. You know, Ethos is the credibility of the speaker meaning, you know, I know what I’m talking about. But it is also authenticity. If I look like I am willing to be transparent and what you see is what you get, that does build credibility, right? If I don’t trust the speaker—I may think they know a lot but I don’t really trust them to be honest—then you don’t really have that Ethos.

So you really want to build up Ethos through showing you know what you’re talking about, you know your facts, you are prepared, you’re a master of the case, you’re a master of the rules of evidence so you look like you know what you’re doing there, but also that you are authentic. That what the jury sees is the real you. That you can be trusted to tell the truth. But you can’t do that unless the jury thinks you’re real. Because the one thing that a jury can sniff out probably more than anything else is whether you’re being a phony or not. And they’ll forgive just about anything. You could be a jerk, you could be whatever you want to be, whatever you are, right? Imperfect as we all are. But if you’re phony, that’s the one thing they won’t forgive. They’ll forgive being a jerk, you know, because that’s human. But they just hate people who are fakes. And so to build up any credibility, you have to be authentic. To be authentic, you know, you have to be willing to take the risk and be unafraid to show the jury who you are, understanding that they may not like certain things but they will forgive just about anything other than not being authentic.

Khurram Naik: To the extent these are trade-offs—let’s say there’s sincerity with being very polished, you know, having tight answers for everything, well-rehearsed, whatever—why is it that sincerity beats out polish?

Joe Ahmad: Because I don’t think juries care about polish, right?

Khurram Naik: Why is that?

This idea of cutting through the noise and getting to what matters is something Rakesh Kilaru calls the “courage to cut” — ruthlessly simplifying trial arguments down to one or two core themes.

Joe Ahmad: Because ultimately I think jurors take their jobs very seriously, right? I mean, I think jurors, you know, I mean look, this is not something that most jurors do every day. This is probably the most direct interaction that a lot of jurors have with their government. They’re walking into this very formal courthouse. They’ve got a judge in a black robe, people advocating for their clients in suits. They’re dealing with a bailiff, they’ve probably gone through the jury assembly room wherever that is, and then they get these admonitions from God, the judge, as to what they’re going to do. And I think they come in there really wanting to reach the right result under the law as they are given.

So they’re not really there, you know, to pick out who’s more polished or anything like that. They’re there to get to the bottom of the truth under the law and get the answers right on the jury charge. So they’re trying to figure out what the truth is and they will ignore a lot of different styles in order to get the result that they think is the right result. I truly believe that. I mean, like I said, if you try enough cases, I think you will be more and more impressed about number one how smart a collective group of individuals is known as the jury, but also how much they want to get it right. And so, you know, this is different than picking out, well, this is the lawyer that I would hire, right? Versus well, you know, they’re a great lawyer but they have bad facts, right? I mean I’ve heard that before, you know. And when I lost sometimes I would hear that too and I’m thinking, well, maybe I wasn’t that great of a lawyer after all.

Khurram Naik: So with you talked about you know when you were starting out, there was trial lawyers you were modeling after and emulating their style. It was a little too far for you. It was just like okay this really isn’t how I am. And you discovered over time how you are. Can you describe your style today and then an inflection point where you really had a discovery about yourself in that way? Maybe it was a single trial, maybe some other kind of moment, that there was a before and after, then after that like okay I’m a little bit different now and I’m a little more authentic to who I am.

Joe Ahmad: Well, I think there’s a lot of things. Number one, my view is I’m not as polished as some speakers are. You know, I’m probably, you know, on the spectrum in terms of having ADD and that will come out, you know. But you know, like I said, part of it is just not being afraid. It’s going to come out probably no matter what, but as long as a jury senses that hey I’m, you know, kind of comfortable with who I am, I’m not trying to hide it, you know, that will mean they’re going to see all of that. Plus you’re spontaneous. You’re not constantly trying to calculate your words, maybe you’re a little bit more—and I hate to use this phrase but I think you’ll know what I mean—shooting from the hip almost, because it seems real as opposed to scripted.

And so even the clothes I wear. I would dress rather formally and, you know, blue—blue suit, navy blue suit, dark gray suit, boring blue or red tie and, you know, but that’s not how I dressed typically. Today I’ve got some attempt at Christmas gear on, I’m not sure how Christmassy I am, but you know, that’s normally the way I would dress. So everything I’ve approached, you know, is like that. My interactions with my staff is like my interactions in the office, right? I don’t treat them any differently in front of the jury than I treat them here. And you build, you know, you build a team of you know where the team sees that you’re being authentic with a jury, it helps other people, you know, be authentic as well. So I think it’s just, you know, letting go of all the fear about trying to be somebody else. Be yourself. You’re going to have flaws. I have flaws. I found most jurors don’t care.

Khurram Naik: Was there a moment, was there a trial or something like that, that really helped you discover authenticity for yourself?

Joe Ahmad: Well, you know, I think what it was was—and this is a little bit of you know kind of circuitous reasoning—but I think what kind of got me off of it was, you know, I was trying cases and winning them with kind of a very formal style. But they were rather easy cases, I didn’t know it at the time. But I remember arguing to a jury—this is an insurance defense case early in my career—and you know, I remember arguing to a jury that they should award a small amount of damages. And they came back and awarded less. Less than what I told them.

Okay? And I thought to myself, you know, I wasn’t—apparently I’ve been winning these cases but it’s not been based upon my credibility, right? You know, they don’t even believe me when I say you should award more to the plaintiff than they actually awarded. And I asked them afterwards and they were like, yeah, you know, you just didn’t seem like you wanted to call it like it was, but we saw the way it was and we didn’t think this plaintiff deserved hardly anything. And we figured you know you were just trying to be nice. I was kind of like, wow, okay.

And that’s kind of the moment where I was realized look, you know, they’re going to see through my attempt to be somebody else, right? And even though I think this is working because I’ve been mimicking the style, it’s, you know, and I had to face the sad fact of well, you know, these cases, of course I was an inexperienced lawyer at the time, I was trying cases at a very low hourly rate and I was winning, but I think I was winning because these are closer to the slam dunk cases—I just didn’t realize it.

And then when I, you know, like I said after that moment, I loosened up a lot, you know, on those types of cases, kept winning because they were still slam dunks. And that gave me the confidence to realize I’m not really going to hurt myself by being authentic. And then when it comes to much harder cases, it was clearly working much better because I would see other side what the other side would do and you know it was very tough for them when they weren’t authentic even when they had better facts. Some of the hardest lawyers that I’ve tried cases against, you know, and I’ve got one lawyer that I tried a case against right up to about the verdict and we settled it, but I will tell you, local lawyer in town named John Kim, you know, I mean he is number one very, very, very authentic. But man is he just off the wall. And jurors love it. They do. It is pretty zany. He wears—I’m not even sure I can call them shoes to court—you know, they’re some version of a colorful slipper. He is funny and irascible at the same time, you know, but you know he is as far out there as you will probably see with most lawyers. But again, that kind of radical authenticity is so effective, it almost doesn’t matter how far out there you are as long as that’s you. And that is him.

Khurram Naik: Can we go back to understanding—so I guess something else that’s interesting is how you think about juries. And so I am hearing a lot of respect you have for juries. And it seems to me that I’ve observed this pattern in several different areas in the practice of law: when someone doesn’t take something, some counterparty or some agent—lawyers are agents, you know there’s different kinds of agents—when people don’t take these kinds of players seriously and then they get poor outcomes, they attribute that not to themselves but to those agents or other players and say, oh well those players don’t know what they’re doing and so of course I’m getting bad outcomes. So I think you hear this from patent lawyers. Patent trials are often tried before juries when they involve damages, they do. And so you hear certain lawyers who speak not very highly of juries and what they can understand from a patent case. And it seems to me that if you take a jury seriously, if you take a counterparty seriously, whoever, you’re more likely to get better outcomes even if you’re in some sense adverse or there’s a conflict of interest, you know, principal-agent there’s a conflict of interest. So it seems to me that you know you get good outcomes if you’re taking these other actors seriously and get poor outcomes and you don’t learn from them because you keep on saying oh they’re just they don’t know what they’re doing. So I don’t know is that a pattern that you’ve observed because that’s what I’m hearing about the takeaways maybe other lawyers have had from similar circumstances.

Joe’s point about how trial experience transforms you reminds me of Jaimie Nawaday, who went from a terrified junior AUSA reading trial technique books on the subway to leading the Bank of America prosecution.

Joe Ahmad: Oh absolutely. I think you have to respect the jury’s ability and like I said it never fails to surprise me. You know part of the problem is say it’s a 12-person jury as we commonly have in state court. During the trial of course they can’t say a lot, right? They can’t say anything most of the time. So you know they’re kind of 12 blank people and you just kind of sense that they’re just literally potted plants listening, maybe listening, maybe not. Some of them are sleeping. And so it’s easy to kind of get or fail to appreciate the fact that yeah maybe one of them is sleeping and the rest are stone silent acting like they don’t care at all. But when you’re done and you talk to the jury afterwards you find out they picked up on so many things. You know incredible amount of things. And you know it’s so much so that I actually even on the plaintiff’s side I don’t like sitting next to the jury.

And I don’t like sitting next to the jury because like I said they notice everything and they particularly notice everything when you’re sitting right by them. And it is very hard in a trial not to keep a complete poker face. Particularly for my clients. It’s relatively easy for me and the lawyers, but my clients you know it’s really hard when they you know they have personal knowledge oftentimes of what’s going on and they have a lot of stake, a lot of emotion behind it. And juries can hate some of those reactions and they will notice. They’ll notice if your co-counsel is furiously scribbling stuff to you while you’re examining a witness and passing you furious notes, acting you know kind of desperate or something like that. I mean they just notice an incredible amount of things and it never fails to impress me.

Now having said that, yeah I think lawyers’ natural reaction upon losing a case is to say every time oh the jury didn’t get it, right? Jury didn’t get it. Now what I’ve learned is that number one, over time I have learned even in cases where I lost and I thought jury didn’t get it, the more I think—even sometimes it takes years—I realize where the jury was coming from. I realize that there were—the other side had a compelling story that I was just drinking too much of the Kool-Aid to see. But after the emotion and everything like that wears off it’s easier to see. The second thing is jurors can look at things—smart people can look at things—completely differently, right? And so that’s why you know I can try the same case twice and get a different outcome both with smart juries. Because you know in a lot of close cases, people look at things differently. I mean look at society around us and you will see how even smart people can look at the same thing very differently. Just a difference of perspective, maybe a difference in you know their history, their background, you know what they’ve done for work. I mean you know if you’re arguing a commercial case to somebody that has felt like they’ve been victimized by people that have breached contracts in their business, you know they’re going to bring that background. They’re not stupid but they’re going to bring that background. So you have to understand people with different backgrounds or even people sometimes with similar backgrounds but just have a different perspective and it’s not because they’re dumb, you know it’s not because they’re unintelligent. They just look at it differently. Smart people can look at the same facts differently, okay? And it’s not because they didn’t get it. So with those two things, you know I’ve been able to account frankly for virtually every jury verdict, good and bad, that I’ve seen. You know most of them I’ve won fortunately, but even the ones that I’ve lost I’ve been able to see how they got there with the passage of time.

Khurram Naik: With juries you mention that there’s patterns of worldviews, beliefs that they have that you have to account for when you’re presenting your story, when you’re presenting facts. And if your fact doesn’t align with one of those theses, principles, heuristics that they have, you’re at a loss. You’ve just got to frame things in a way that’s beneficial to their perspective and lens. So there’s patterns of these. And so you know you’ve done work on both plaintiff and defense side and you mentioned say corporations—there’s a pattern of view that about a pattern of view that that about the reasons why a corporation does things or how they operate. Can you talk about some of the patterns you’ve observed from juries?

Joe Ahmad: Yeah, so the first thing is that persuasive ability—I mean the ability to move somebody from point A to point B—is actually much harder than most lawyers think it is, right? You know if you think about the worldview of a lot of people, you know, and you think about for example the political world no matter which side you’re on, right? If you think about how easy it would be able to take somebody on the other side of the political spectrum and move them onto your side you realize, or how hard it would be to move you to the other side political spectrum, you realize you know certain things are just hard to move people on. Now most trials aren’t the political world, but if there is an entrenched worldview, you know you’re far better off trying to convince a jury of something they already believe—i.e. get your theme to fit into their view—than it is to convince them that their view is wrong to start off with.

So when it comes to corporations, there is a worldview particularly after COVID, right? I mean I think it probably existed to some extent among certain people but after COVID the view that corporations are not necessarily benevolent has skyrocketed. And what all jurors believe is—not all jurors but a lot of jurors believe—is they are motivated solely by profit. And if you’re trying to argue that your corporation did thing because it was the right thing to do, it often times—especially with big companies, right? The smaller the company the more credibility it can have or the more sympathy it can have. But you’re far better off trying to show that the company acted legally and in harmony with its profit interest and not to hide that, for example. Because there are some cases where the company’s profit motive and if the company acted in accordance with its profit motive actually demonstrates that they didn’t act illegally, right? Because sometimes for example you have to prove a certain motive for the company where their profit motive would not be consistent with that motive. Get behind that. Right? Don’t have to worry about the fact that a juror is going to think that your corporation is all about the money because many times that’s what they already believed anyway. So you might as well make that work for you. I think it’s very difficult to try to convince a jury that the corporation doesn’t.

The culture Joe has built at his trial boutique — where there’s no shame in losing — echoes what Randy Gaw built at Gaw Poe, a firm he started specifically because BigLaw wouldn’t give him first-chair trial work.

The second thing is, especially with bigger corporations, they believe they are far more organized than they actually are. I mean after representing many corporations, even the biggest corporations, you will find that they’re not always perfectly functioning organizations. They’re not always the well-oiled machine. And oftentimes left hand doesn’t know what the right hand is doing. You think they would have perfect documentation on everything; they don’t. However, jurors think that they do. They think that there’s going to be—if something important happened—there will be documentation. And so that can be helpful, it can be harmful, but it’s a reality. Jurors think that they’re far more organized and documenting everything than they actually do. And now if the juror has worked for a big corporation, a lot of times they will see that and recognize that because they’ve experienced it. But for a lot of jurors that haven’t—especially younger jurors that may have not had a lot of time in the workplace, not a lot of time with corporate America—I think they have views that jurors perhaps or corporations rather are you know very well-run organizations. And even if they are well-run, no corporation is perfect.

Khurram Naik: What case, what trial made you the most emotional—happy, sad, angry, any of that?

Joe Ahmad: Well, first of all, I think anytime you get the opportunity to take your case to a jury, generally speaking, that is—that should be a great moment, right? Because yeah I mean there’ll be a winner, loser, somebody that you know maybe or maybe both sides won’t be thrilled with the result. But the one thing you can say is you know they got their day in court, right? And you know I will tell you, I’ve had some cases where the client lost but they felt good about the result in the sense—not the result that the jury gave but the sense—that they got their day in court, they were heard. You know, because a lot of times when you settle cases you don’t really know what the outcome would have been and there’s always this kind of nagging doubt about what the real outcome would have been.

Now of course the real outcome can be highly variable as I mentioned before, but at least you would have an outcome. With a jury trial there is never that doubt. Right? So from my point of view, I think it’s always a good moment in time when you are trying a case and I think a lot of clients want that, right? A lot of clients want to go to trial. Now sometimes especially with larger companies, they just don’t—they’re very risk-averse and they don’t want to take that risk, that’s absolutely true. And you know if they do go to court, they are on edge. If they get an adverse impact or an adverse result, then yeah I mean they can be unhappy with it. But my experience is a good many appreciate the fact that they got their case to trial even even when they lose. And for those people, you know, and I try to talk to them about this, I think the lawyer’s job is to educate them on what we all know which is what we’ve talked about which is there is risk. Right? And if you do that, I think you have a much better chance of having a client happy with the outcome even if it’s a negative outcome. If you haven’t done that and you’ve kind of promised them a bed of roses and you get a bad result, yeah you’re going to have a problem.

Khurram Naik: What about for you though? What trial got you the most emotional—gratification, anger, any of it?

Joe Ahmad: You know I’m always on edge when a jury comes back. And you know so the one thing I will tell you is even cases that might seem the most mundane, you know, somebody cares about the outcome a lot. But even if that weren’t true, which it virtually you know is every time, I care, right? I’m on edge every single time. And so you know to be perfectly blunt, picking out one or two cases is somewhat difficult because I won’t say angry, don’t know that I’ve ever had that emotion, but when there is a negative result, yeah I mean there is at least disappointment, sadness every time there is a negative outcome. And then of course you know when you when you win, you’re almost always elated.

If I had to pick out a case, you know I guess there’s a recency bias so I’ll pick one that was within the last you know three years. You know we did a breach of contract case for a large physician group in town against a hospital where the practice group was operating. And you know basically the hospital had—our contention was—in a contract promised that they wouldn’t set up competing facilities, facilities that did the same kind of surgery. There was a dispute about that. But this was a large group of physicians that candidly had felt because you know they were economically—doctors do well, these doctors you know did well—but economically they were definitely the small player with the least amount of leverage vis-a-vis this large hospital group. So they felt that they had been taken advantage of for years by the hospital. So there was a lot of emotion there, right?

And when we were able to get a great outcome—I think it was the right outcome, was the right outcome we believed under the contract—but you know the sense of joy and satisfaction was immense. And I think what distinguishes this perhaps from other cases is number one the number of clients that were impacted because it was a large physician group, but also we had a great trial team. And that’s what made it a tremendous experience throughout the whole process. You know we had somebody who was running the case, one of my colleagues Paul Turkevich, who had done you know just an incredible job in terms of working up the case. You know and we had you know another partner of mine Kyle Pelker did an amazing job. We had an amazing appellate lawyer you know Kelsey White and you know we had a young associate Karina Sanchez and you know legal assistants did an amazing job. I wouldn’t have you know wouldn’t be here saying hey you know we got a great result had it not been for the efforts of everybody. And we had a great time doing it. So working with a great team, working with a large group, a great group as a client—that probably made it the one if I had to point one out, that would probably be it.

Khurram Naik: And you mentioned some you know more junior lawyers on your team. Final question for you. For lawyers that are at a firm like yours that are getting great trial work—there’s a number of other great boutiques that do trial work in Houston and elsewhere—so they’re getting great hands-on experience. That’s those are conditions in their favor that they’re setting themselves up well for their career. What is the biggest mistake those lawyers make while they’re going down that path?

Joe Ahmad: Well I think you know when we talk about risk, right? The I think what stops a lot of lawyers, especially young lawyers, in terms of trying cases is the fear of the impact it’ll have on them if they lose. And so the number one thing you ought to be thinking about is being part of a group, going to a firm where there’s no shame in losing. And I think at our firm you know I think we’ve built a culture where no you come back the next day from trial and everybody’s proud that you you know you did the good fight, right? We’ve all lost cases. So nobody takes it as a badge of dishonor when you’re willing to fight and you work very hard but you get an adverse outcome, right? That’s going to happen. And we as a firm are supportive of everybody that goes through the fight win or lose.

And I think when you’re if you want to be a trial lawyer and you you know you want to get the right training and experience to be a trial lawyer, it’s got to start with the culture. And it’s got to be a culture that is willing to let lawyers, young lawyers, try cases and lose, right? And I think we do both. You know I mentioned that case we have for the physician group. You know I mentioned for example some partners but also associates like Karina. My partner Kyle and Paul Turkevich were associates at the time. And Karina was a particularly junior associate. All of them had speaking roles during trial, all of them took witnesses during trial. And I think it’s very important and I think it really helped our team win the case when the jury got to see you know not just a well-functioning trial team but a group of people that really enjoyed working together and such and had confidence in each other. Confidence to the point where we had obviously younger so you would think less experienced lawyers that were getting trial experience. And it worked wonderfully. So you know you want to go to have that environment where the the firm has confidence in the young lawyers to try cases because they’ve given the training that they need to go out and get real responsibility but also is willing to allow those lawyers to take risks because you have to to become a trial lawyer.

Khurram Naik: Do you have time for a bonus question?

Joe Ahmad: Sure.

Khurram Naik: Okay you mentioned books on persuasion, you mentioned studying trial lawyers you said hey you know not much changes but there’s a canon that you can tap into. What’s an underrated book on persuasion and and how do you study trial lawyers of the past?

Joe Ahmad: Well I can tell you some books—I’ll give you the authors, right? Because I think you can pick out a number of different books by these authors. I’ll start with one that might be the most obscure is and he was a judge I believe in New Jersey named Herb Stern. Maybe a little bit unorthodox perhaps but that was probably the one that had the biggest impact on me as a young trial lawyer and I think his can be extraordinarily valuable some of the things that he said I think have stayed with me. I have encouraged other lawyers to read his books. Somebody even further back Moe Levine, great advocate. Read everything you you can from him. Jerry Spence another tremendous advocate. We talked about authenticity; this is a guy that wore you know hardcore Western gear and because that’s who he was. And he and he had a trial lawyers school. I didn’t go to it but people that went to it rave about it. But if you can read something from from him. You know there are many others. Now we have the the new Reptile Theory we have books you know by Keenan and Ball I think they’re great books especially if you’re on the plaintiff’s side. And so yeah I mean you know there are then you can go back to you know again the Greek philosophers talking about Pathos, Logos, and Ethos, right? You know they’ve got a lot of ancient books on advocacy. You can also read books on you know famous trials and see what the lawyers did in those cases.

And I remember Dick Miller who was the senior named partner of the first firm that I worked for, tremendous trial lawyer, tried the Pennzoil Texaco case by the way for Texaco and to talk about you know taking a loss you know he lost 11 billion which at the you know in the 80s was a lot of money, you know? So and came into the office the next day and said well just another day at the office. You know and got back on the saddle and worked on his next case, you know, continued to try cases after that. Great lawyer. But you know sometimes great lawyers lose like he did in that case. So he would read for example these Queen’s Bench old British trials and talk about how that that really helped him. So so yeah I mean there’s so much out there and if you want to be a great trial lawyer I think you want to read as many of these types of books as you can because outside of actually going to trial yourself, this is some of the most helpful stuff there is.

Khurram Naik: Well this episode was some of the most helpful stuff there is. This is some really great insights here Joe.

Joe Ahmad: Well thank you Khurram. Always a pleasure.

For years, I felt like I had my health dialed in—consistent sleep schedule, regular workouts, predictable diet.

But in 2025, I made what turned out to be one of my best purchases: an Oura Ring. And it completely changed how I think about health tracking and self-awareness.

My wife Emma had been using an Oura Ring for years, constantly showing me her readiness scores and sleep data. Honestly, I didn't get it. I thought I knew my body well enough without needing technology to tell me what was going on.

From Skeptic to Believer

The turning point wasn't about jumping on a trend or trying the latest gadget. It was about realizing that what I thought I knew about my body and what was actually happening were two different things.

Here's what surprised me most:

• Things I worried about weren't actually issues. I had some concerns about my breathing and oxygen saturation during sleep, but the data showed everything was fine. That peace of mind alone was valuable.
• Things I didn't know about were creating problems. I discovered that eating within a couple of hours of bedtime was significantly impacting my sleep quality. I also learned that my caffeine timing and frequency needed serious adjustment—something I never would have connected without the data.
• Things I suspected were confirmed. My step count was lower than it should be, and seeing that number every day motivated me to move more.

Running Bloodwork

The Oura Ring did something else unexpected: it motivated me to get comprehensive bloodwork done. Once I started paying attention to one set of metrics, I wanted the full picture.

I dig deeper into this topic in Legal Conference Tips: Renting a Legal Network.

The results were eye-opening. My insulin sensitivity and inflammation markers looked great. But my cholesterol-related biomarkers were way too high. Looking at my diet, the culprit was obvious: I was eating a lot of red meat and saturated fat.

Armed with this information, I made immediate changes. I cut way back on both red meat and saturated fat and started incorporating significantly more fish into my diet. I also stopped treating Zone 2 cardio and VO₂ max work as a "someday" priority and made them non-negotiable parts of my routine.

Listening to My Body

Perhaps the biggest unexpected benefit has been how the Oura Ring helps me actually listen to my body. I've always had the classic "push through it" mentality—the idea that consistency means showing up no matter what. But I'm learning that smart training means knowing when to dial it back.

Case in point: I had planned to do my annual polar plunge yesterday, but I'm coming off a cold. My recovery scores were telling me what I probably already knew deep down—my body needed rest, not an extreme cold stressor. So instead of pushing through, I stayed in the sauna. Old me would have done the plunge anyway and probably extended my recovery time by days.

Other Best Purchase

While we're talking about purchases that improved quality of life, I have to mention our second-best decision: paying our cleaner to add a second cleaning each week. Sometimes the best investments aren't in gadgets or gear, they're in time and mental space.

Conclusion

The Oura Ring isn't magic. It's simply a tool that reveals patterns you might otherwise miss. What makes it valuable isn't the technology itself—it's that it helps you see what you're missing and motivates you to act on what you already knew but weren't addressing.

For me, it bridged the gap between feeling like I was healthy and actually optimizing my health. It turned vague intuitions into concrete data points, and those data points into actionable changes.

This idea of using data to optimize wellness reminds me of my conversation with Patti Burris, who developed what she calls a 7:2:3:1 wellness ratio to thrive while billing over 2,400 hours in BigLaw.

If you've been on the fence about health tracking, my advice is simple: the insights are only valuable if they change your behavior. But if you're ready to actually act on what you learn, tools like the Oura Ring can be transformative.

I wrote this piece for Vault.com because I kept seeing the same pattern: smart, hardworking attorneys stalling out not because they lacked ability, but because they hadn't built the relationships that create opportunity. Social capital isn't a soft skill or a nice-to-have. It's the multiplier on everything else you've worked for — and nobody teaches you how to build it in law school.

From the article:

"Your success as a lawyer does not depend solely on your abilities — your human capital. Most lawyers are pretty smart and hard working. So, it's not knowledge and ability that set lawyers on different paths. Career success depends on the opportunities you get, take, and create in order to channel those abilities — your social capital."

"Like any investment, building a legal network takes an up-front outlay for a future benefit. The earlier you invest and the more you contribute, the more opportunity you create for growth. Like many other investments, this one compounds in value over time — if you tend to your investment."

"Early in your career, it is often hard to see the value of your network, but the earlier you begin building it, the more likely it is ready when you need it. Otherwise, you're stuck asking for favors from strangers, and that won't get you very far."

In the full article, I walk through the exact framework I recommend: find your community, make your first connection, build triangles of relationships, contribute value, and stay consistent. It works whether you're a 1L or a fifth-year associate who's been too heads-down to think about this. The best time to start was yesterday. The second best time is now.

Read the Full Article on Vault

The placement process moved fast, was strategic, and resulted in a package that included both a signing bonus and a non-prorated 2026 bonus.

Here's what made this placement unique.

Precision Targeting

We mapped a short list of firms that would value this lawyer's trial and deposition experience.

That paid off when this lawyer picked up 10 interviews in a few weeks.

Clarity Through Prioritization

Interviewing at multiple firms didn't just help clarify fit, it helped define this lawyer's top priorities in considering firms.

Parallel interviews created clarity and prioritization.

Speed Wins

Counterintuitively, interviewing at several firms accelerated timelines.

One firm completed all interviews in 2 hours and issued an offer soon after. The lawyer accepted 16 days from submission.

This process facilitates clarity through prioritization and speed.

Economics Followed Fit

The final package included a signing bonus and a non-prorated 2026 bonus. We show firms that bonuses de-risk hires for firms and lawyers.

12 out of 15 of the lawyers we placed this year picked up a signing bonus, non-prorated bonus, or both.

Conclusion

This placement demonstrates how precision targeting, parallel interviews, and speed can work together to create clarity and drive results.

Here are my main key takeaways:

• map firms strategically
• interview at multiple places to define priorities
• move quickly to accelerate timelines
• structure packages that de-risk the hire for both sides.

We're seeing surging demand for life sciences patent litigators, especially those with trial experience. Another life science patent litigator is interviewing at 6 firms. Much to celebrate this winter!

Follow me on LinkedIn for more life and business updates like this.

I get why people do it. More recruiters = more opportunities, right? Cast a wider net, increase your chances.

But here's what actually happens when you work with multiple recruiters.

No Leverage

You get an offer from Firm A through Recruiter 1. Great.

But Recruiters 2 and 3 have no idea. So they can't use that offer to push Firm B or C to move faster. They can't negotiate better terms. They can't create urgency.

Each recruiter is operating with 30% of the information. And offers are only leverage when someone controls all of them.

Pitched, Not Advised

Once multiple offers come in from different sources, everything changes.

Recruiter 1 tells you why Firm A is the best move. Recruiter 2 explains why Firm B is actually better. Recruiter 3 pushes you toward Firm C.

They're not helping you compare anymore. They're selling their specific opportunity.

No one can give you objective advice because everyone has a horse in the race. You end up in this really uncomfortable position trying to manage conflicting advice from people who can't see the full picture. And no one does their best work in that situation.

Our Approach

Unfortunately, this is standard practice in legal recruiting. Most large agencies are highly flexible about working alongside other recruiters.

We're not.

So, we turn away talented lawyers. Sometimes with outstanding credentials. Because they've already applied somewhere, or they're working with another recruiter.

But for the lawyers we do work with? We're the single source of truth.

• We manage the entire process
• We create the competitive pressure that gets firms moving
• We leverage offers to get them the best deals

They get multiple offers, objective advice, and someone who can actually leverage their options.

Conclusion

Working with multiple recruiters seems like a smart strategy to maximize options. But in practice, it fragments your leverage, creates conflicting advice, and leaves you managing a process no one fully understands.

The lawyers we work with get multiple offers, not multiple recruiters. They get competitive pressure that moves firms faster, and advice that's truly objective because we control the entire process.

In our experience, that's worth more.

The data backs this up — when our candidates interview at four firms simultaneously, the offer rate approaches 100%. See the numbers here.

Enjoyed reading? Follow me on LinkedIn for more content like this.

Based on our data from 14 placements at Freshwater Counsel this year, once a lawyer reaches 3 firms interviewing, the odds of an offer rise above 85%. At 4 firms, the offer rate hits around 100%, and the first offer typically arrives within 7 to 10 calendar days. Most lawyers at that stage end up with 2 to 3 offers within a two-week window.

Strategy Shifts

That's when the strategy shifts from creating opportunities to managing timing.

Which firm's process is furthest along? Which firm aligns best with long-term goals? How do we pace the last few interviews so you can compare offers side by side instead of one by one?

Less Work

One of the most surprising benefits of interviewing at multiple firms is that it ends up being less work for the lawyer.

That's because interviewing at multiple firms accelerates the interview process across firms and increases clarity of fit.

The interview process gets accelerated when firms know they're competing for top talent. They're maximally invested in a smooth and compelling interview process.

Creating Clarity

This process also creates clarity for the lawyers. No one ever has certainty that they're ready to leave a firm or that they know the right firm. But when you interview at multiple firms, you get better insight into your priorities.

That's why one lawyer we placed this year accepted 1 of 2 offers in 12 days. And why another lawyer accepted 1 of 3 offers in 18 days.

Real Results

This isn't theory. It's happening right now. We presented a NYC patent litigator last week who is now interviewing at 4 firms. Now we can advise this lawyer and the firms interviewing on what to expect based on our insights from past placements.

We create strong options to find clarity of fit, and then we advise lawyers and firms using the insights from our placements.

Conclusion

Interviewing at 4 firms creates a competitive dynamic that benefits everyone.

Key takeaways:

• at 3 firms, offer odds rise above 85%
• at 4 firms, the offer rate hits around 100% with offers arriving within 7 to 10 days
• multiple interviews accelerate firm processes and clarify priorities for lawyers

The strategy shifts from generating opportunities to managing timing and comparing offers side by side. One lawyer accepted 1 of 2 offers in 12 days. Another accepted 1 of 3 offers in 18 days. The process creates clarity through competition and gives lawyers the insights they need to make confident decisions.

I’ve written about why having one recruiter manage this entire process matters — it’s the difference between fragmented information and full-picture leverage. Here’s why working with multiple recruiters backfires.

Liked this article? Follow me on LinkedIn for more.

Patti’s law school story begins with walking into the wrong job interview, which led to a life-changing mentorship. She shares the principles she used to call her shot in law school and end up at the top of the class through relationships with peers and professors, systems for learning, and cycles of sprints and rest.

Now, as a driven biglaw funds lawyer, Patti shares the formula she uses to ensure she’s investing in herself every week. Patti also shares how she stacks goals (social, academic, professional) for exponential returns.

Keep reading below for the full link to the episode and the full transcript of our conversation.

Top Insights

Below are the highlights of our conversation:

• The Power of Serendipity and Grit: Patti shares the incredible story of how walking into the wrong office for a job interview led to a high-stakes role with a venture capital investor, proving that being an “opportunist” who can simply “figure it out” is often more valuable than a perfect resume.
• The 7:2:3:1 Wellness Ratio: To survive the grueling pace of BigLaw (where she billed upwards of 2,500 hours), Patti developed a strict “Wellness Ratio” to protect her mental and physical health: 7 hours of sleep, 2 healthy meals a day, 3 workouts a week, and 1 thing to look forward to every weekend.
• Overcoming Analysis Paralysis: Patti discusses why so many young lawyers are terrified of making the “wrong” career move and how to reframe the fear narrative by looking at the “most likely” outcome instead of the “worst-case” scenario.

Listen Now

Catch the full episode on your favorite podcast platform.

Spotify

Or click here to listen on Spotify.

Apple Podcasts

https://embed.podcasts.apple.com/us/podcast/044-patti-burris-on-going-from-teen-mom-to-funds-attorney/id1536579571?i=1000734468743

Or click here to listen on Apple Podcasts.

Full Transcript

Khurram Naik: So Patti, when I first learned about your career story, you said to me, “Oh, did I tell you the story of my career about how I came to law?” and I thought maybe I knew something about it, so I said, “Oh, maybe, just tell me about it.” Then you told me the story and just as the story progressed, every point I thought the story was over because it was already incredible enough, and then there’s another part of the story that’s more incredible. So I’d love to start with that. And so your story in Massachusetts begins at a Regus office. Can you tell that story?

Patti Burris: Absolutely. It was 15 years ago, I moved to Massachusetts. I was a mom, I had two boys that were adolescents and I needed a job to continue supporting them. I only had an associate’s degree, I had a bookkeeping background, so I was offered an interview with a company to interview to be their full-time bookkeeper. Being from Deep East Texas, a very rural region in Texas, I had never seen a Regus building. I was unfamiliar with the concept of shared office space or temporary office space. So I went into the lobby, introduced myself, sat down, and a gentleman came out and said, “Are you here to interview?” and I said, “I am.” So I went with him to his office, and he sorted through a pile of resumes on his desk, couldn’t find mine. And he said, “Well, my assistant must have left it out of the pile, no worries, let’s get started with the interview.”

So about halfway through the interview, two other gentlemen came into the room and said, “We think you have our interviewee,” and I said, “Well, this is embarrassing.” So I went to the correct interview and completed that interview. And on the way out, the gentleman with whom I had been interviewing caught me and he said, “Hey listen, I would like to finish the discussion. But to be very direct, I would like to offer you the position.” So at this point, I don’t know what the position is. And he said, “I will offer you a salary of $75,000 and benefits that start on day one,” and I said, “I accept.”

I still didn’t even know what the position was! So it turns out I was being hired to be the executive assistant to a venture capital investor. And I quickly learned he was involved in a number of endeavors, from everything from entrepreneurship, angel investing, venture, and if you told him that you couldn’t do something, most people did not continue to work for him. So it didn’t matter what he asked me to do, I would figure out how to do it and quickly climbed the ranks to become second-in-command of the local office. He employed 850 people nationwide and I was really just his right-hand man.

And about two years in, someone said something condescending about someone with a bachelor’s degree in his and my presence, and I defended them. I said, “Well, I don’t have a bachelor’s degree,” and he was speechless. He said, “You don’t have a bachelor’s degree?” and I told him, “I never said I have a bachelor’s degree. I never saw the job description, you never saw my resume.” And he said, “Well, at this point, you do the job well.”

So four years in, I was the corporate controller of his organization at this point, and he came to work and he said, “I have great news, we’re moving to Laguna Beach.” And I said, “Who?” and he said, “My wife,” and he said, “Obviously, you will go too.” And I said, “I can’t do that. I only moved my children here five years ago, they’re teenagers now, I can’t ask them to acclimate again.” And I cried at work for about three days. I knew I would never get another job like that, it was just—the circumstances would never align, and I live in Boston, the most educated city in the United States.

On day three, his wife was in the office and she was crying, and she said she was devastated to lose me, that their life had been a lot better with me on board, that she had had him at home a lot more because he trusted me. And she said they had always planned to make sure that my boys and I were cared for. So she said, “You know, we still want to do something extraordinary for you. You always wanted to be an attorney and we want to see that happen.” And I told her, “That’s really fantastic, I appreciate the kind words, but there’s this whole supporting my children thing that I have to do now.” And she said, “Well, you need two years to a bachelor’s degree to apply to law school. So what we’re offering is a severance that you will be very comfortable the next two years, you will not feel any diminishment of your income in the way that it’s structured.” The terms are confidential, so I can’t say much more than that, but she said it’s contingent on you finishing your bachelor’s degree and applying to law school.

And of course, me always planning the long game, I said, “Okay, what happens when I can’t pay for law school? If I get in and I can’t pay for it?” and she said, “You’ll figure it out, we have faith in you.” So I signed up at UMass Lowell. It was five minutes from my house, I lived in Lowell at the time. And every assignment I picked up over the next two years, my driving thought was “I can’t afford law school.” So I tried harder than I had tried at everything. I understood that becoming a Commonwealth Scholar could help my applications to law school. Most people have four years to meet those qualifications, I only had two. So consequently, every course I took was an honors course and though I was not the only person in my college at UMass Lowell to graduate with a 4.0, they weighed the difficulty of the courses and ultimately I graduated as the Valedictorian of the College of Fine Arts, Humanities, and Social Sciences.

At that point, I had applied to law schools. I had scholarships from almost every law school in the region, and I had full-ride offers from Suffolk, New England, and New Hampshire. I didn’t understand academia, so I wasn’t really aware that to practice in the venture capital and private equity space, that it could have been worth it to invest in one of the higher-ranked or more prestigious law schools, so I accepted at Suffolk. In the first week, they had an admitted students event and I attended that and they asked me what I wanted to do with my career. And I told them I have this experience in the venture capital space, investment, and I know I want to do private equity or venture capital law. And again, I was met with the uncomfortable—the obvious—that someone has to break news to me and they said, “Okay, like, we’re a great law school, you know, known for litigation and the judiciary, however, where do you want to practice?” and I told them, “Goodwin Procter or Kirkland & Ellis.” And again, you see a little bit of surprise and they said, “Okay, you’re going to need to be in the top five.” And I said, “Okay, top 5%, there’s 300 people, I do still have kids but I think I can probably do it.” And they were like, “No, people. You’re going to need to be in the top five people.” And I said, “Okay.”

So I finished 1L at the top of my section and at that point, I did early OCI at Kirkland and Goodwin, I did regular OCI at a number of firms and ultimately at the end of 1L, I chose between Ropes & Gray and Goodwin. And I committed to Goodwin, spent my summer there, they understood that I had the boys, that I had some challenges not all students have. They had a clerkship program and they created a position to allow me to clerk through school at the firm, so I worked at Goodwin continuously since then. And I guess it suffices to say everything that happened to me was a result of going to the wrong job interview in a Regus building.

Khurram Naik: Yes, I would say that definitely is an unlikely outcome from going to the wrong office in Regus. But so, let’s going back to your time at that funds financial services company. So you mentioned there was this attitude of finding ways to make things happen and just rejecting the assumption that there were things you couldn’t do. Can you give us some specific examples of that and then what were scenarios where you said, “Okay, this seems impossible but I’m going to figure out a way,” and then how did you do that?

Joe Ahmad: Absolutely. So my boss at that company collected luxury cars, from Ferraris to Rolls-Royces, any kind of car you can imagine, and because he was such a good customer, he had access to limited edition cars. There was a situation at the time—I’m not sure if it still rings true—but if you sold these cars prior to 500 miles or so, you could generate pretty large profits on them because of the supply and demand. So at one point, when he was turning a profit on these cars and then occasionally taking a loss, he said, “I’d like to start a business around it,” and he came into my office and he said, “Hey, do you know how to start a car dealership?” And here I sat and I just looked at him dumbfounded and I said, “Um, yeah, sure, I can definitely do that.”

And so he left and, you know, that sounds like an overwhelming thing—and I’ve run into a lot of overwhelming things in my life as I’m sure we all have—but the fact of the matter is the concept of a car dealership is not new. Someone has done it before. Therefore, I only need to do the proper research to figure out how other people have done it and therefore we can do it too. And that’s exactly what I did. I figured out the permitting system, the allocation of cities, how many permits they have, how you go about one, that you have to have an office on-site where you keep your inventory, all of these registration requirements. And within two days, I had delivered him a full plan, from the entity creation formation all the way through the permits and registrations with the state and the cities and a plan to how we could open a car dealership.

He was in everything from farms in the Midwest—he was a genius investor. So when the crisis happened, the property and housing crisis in ’08, he bought up all of the farmland that the farmers had lost and then he leased it back to these same farmers. That was their only way to make a living. So that was one blanket rent payment a year, he would pay one insurance payment a year, and these investments just ran themselves. So farmland was something I worked on. Luxury cars. He had a nursing home chain. He opened a medical supply business with the sole goal of being acquired within a few years by Medline or McKesson and was—he was successful at that.

So essentially, I would help him with all of these endeavors, open these businesses and help him run them, babysit them until they were big enough for a board of directors or to get acquired. And through that is where I learned that I would like to learn how to do this myself. I had learned that, you know, I come from a very humble background and this is one of the wealthiest self-made men that I’ve met. And much like other people that I’ve met now that are more comfortable than I am financially, they learned how to make money off of money. So I did always want to be an attorney. I learned that I would be more appropriate in the corporate space. I like to be liked, I like other people, I like collaborating to get a project in common completed. So that’s really—any given day, I had no idea what I would be working on, but I learned to embrace it and love it.

Khurram Naik: So you saw—it sounds like this person is unusual in having just raw investment skill that can translate across very disparate industries and seems like business structures. That’s pretty rare, so it’s a really valuable person to learn from and you were learning very closely from this person. If I’m hearing you right, it sounds like you’re preferring the kind of work that you do—like, why don’t you be an investor? Why do that instead of practicing law? It sounds like you just inherently like the nature of the work—so for instance, the collaborative aspect of it. I don’t know enough about the nature of this person’s businesses, but maybe they were less collaborative, less about other people and problem-solving in the way that you enjoy. What’s your take on that? Like, have you thought about going down that route or are you—do you enjoy inherently the work of being a lawyer? Like how do you think about that?

Patti Burris: I’m risk-averse due to my background. I understood that if I graduated law school with a law degree, I hold something of value that I can never lose and that I can leverage into opportunities. And from that point in life, I can go from the place in which I always existed—from becoming a mother as a teenager through that point in life, which was 39 years old—I operated from a place of safety and survival and a constant fear that if something went wrong, I could lose everything, my children would pay the price. And at that point, I understood that even if I never achieve wealth, even if I never achieve big-law momentous success, no one can ever take that from me and I’ll be okay.

The investor side, I do find it fascinating. The more that I’ve worked on the law side, I find it more fascinating, and the entrepreneurial spirit is inspirational to me. And the upside, the potential upside in working in private equity is unlimited, it’s incredible right now. So it does appeal to me, but I tend to play it more safely. And every opportunity that was put in front of me, there was the analysis of how can I maximize this opportunity the safest way possible. Now that the boys are all grown and gone, I might take on more risk, but at the same time, my life feels like a dream every day as it is. I never dreamed I would be able to swipe my credit card without worry, to pay my bills in advance, anything like that. And I’m pretty happy doing what I’m doing. So I do try to limit that. I think the little motivator inside all of us who are type-A or lawyers or high achievers, that’s always “what’s next, what’s more.” That’s where I’m at now is trying to assess when it’s enough.

Khurram Naik: Yeah, I think it’d be interesting going back to law school to talk about how you de-risked that opportunity so you don’t accidentally end up to be—you said third from last? And so that’s—you have to be very deliberate about making that happen, especially with the constraints you’re working with. And of course other people in law school have constraints, but yours are pretty pronounced and I think most lawyers would agree that those are significant constraints compared to other people. So tell me about how you approached law school. How did you set yourself up for success? Tell me the semester-by-semester playbook for how you progressed and pulled yourself forward.

Patti Burris: Absolutely. So my—I was largely driven by anxiety and fear in the first two semesters. You know, I had imposter syndrome, which I think drives a lot of attorneys to do good work. But then also my children. I was out of the home, I did still team mom for all their sports teams, I still sat on every board of directors. At this point, I had taken another teenager into my home and was helping him build a professional sports career. I still had all of these obligations and I didn’t want to take away from them and then not yield the result that I was doing that for. That was the goal.

So my first semester of law school, all I did was study. I did everything I was told. I thought to myself—not dissimilar from what we discussed about the car dealership—I’m not the first person to go through law school. These professors in this school are giving me the blueprint to success. They’re telling me, “If you read these cases ahead of this deadline and you outline them and you read and you participate in class and you answer questions and you listen to your professors, you will be successful.” So I did everything that was prescribed by the school.

And then in addition, I thought, “How can I maximize the time that I give to school, the investment that I give to school against my busy life?” So at that point was a time analysis. There’s only so many minutes of the day, so many waking minutes of the day, and how can I use every one of those to advance my goals and or my responsibilities? So where it could be that between 30 minutes between one class and the other class other people would walk to get a coffee and socialize, I would sit and outline my materials for that class.

I had one course in which I did not understand the professor’s preferred approach to teaching, nor did my classmates. I think he forgot we had the toolbox of a 1L. He was a brilliant Yale guy, had worked at the SEC, and he just taught on a very high level. I quickly realized I would not be able to learn contracts from this person. Not due to any fault of his, I’ll just say I couldn’t learn in that style. So instead of spinning my wheels and listening throughout that class, I would in that class do my homework for other classes and then I also downloaded all of the Barbri contracts courses that you do as a 1L and I would put in my AirPods and I taught myself contracts through Barbri in that time period. I did end up winning the Jurisprudence Award for the highest grade in the class in that course through that method. So there were sometimes there was an analysis of figuring out just what works for me and how to do things more efficiently.

I did have social concerns. I, despite being an extrovert, a social butterfly, I was much older than all of my peers. I did want to fit in. I did want to have those lifelong friendships. And every Friday everyone would get out of school around 1:30, 2:00, and they would go to Sidebar at Suffolk, on the side of the Suffolk building, and that was like the team bonding. As much as I wanted to enjoy the social aspects of school, I would go to the library instead. It was the only day a week that the library was slow, that it was quiet, and I would do all of my outlining.

Patti’s willingness to take a leap reminds me of Sunny Kim, who quit her BigLaw tax job without a backup plan, wrote one LinkedIn post about it, and 60,000 people read it. She now teaches lawyers how to build authentic personal brands.

Other students quickly picked up that I was ahead on outlining, that I like to be helpful. So anytime students missed class, I would share my notes with them and even my outlines at the end of the semester. Where other students tended to be more protective of their outlines, it was my opinion that if you waited until two weeks before the exams to start, I’m not going to have to outcompete you for rank, which was the concern of all law students. So I would share my outlines and even teach them the material. We would go in study rooms and I would help them, and that was another way I helped drill it into my brain. My train rides to and from Lowell—I had almost two hours a day on the train—I would brief my cases for the next day. If momming picked up and I didn’t have time to brief my cases, I would go to Quimbee. I would at least do every little bit that I could. But that whole—I would say throughout the first two years of law school—it was figuring out how to make every minute of my waking day work toward my goals.

Khurram Naik: How do you think about law school as—for better or worse—a zero-sum game in terms of rank, right? So in that sense, it’s zero-sum and it’s a very important sense of how people go to law school. And then some people like yourself understand that another part of law school is collaboration because, hey, these peers are yours, they’re going to go on to do a number of things. And if you only look at it professionally and only look at it for the instrumental gain you’ll get, from that lens alone it’s good to do this, apart from just—it’s inherently good to just connect with other human beings and it’s just—some people have missed the appreciation that this is a really unique phase in life. So Patti, like you, I went to law school after some years and I felt very old. I entered law school when I was 28, which you know, now I mean, it doesn’t seem like young but it definitely doesn’t seem like old. So but yeah, I think that gave me some context to say, hey, like, law school, like, being in school is a really unique thing. Like, this is just a unique format that you don’t really get to take advantage of very often. So tell me about how you thought about the—you had your resolute to say “I need to get in that top five because I have these outcomes to achieve.” That’s a zero-sum game. But then there’s these other collaborative ways to work with other people. How do you synthesize those two beliefs and attitudes then and now?

Patti Burris: So innately do believe in karma. Not—not in so much as there’s a cosmic force, you know, that’s around like checking everyone, but I do believe that what we put out is the energy that we see around us and the energy that we notice and let affect us in return. And I do believe in helping other people. I do believe good things come of it. And then there’s also the pragmatic knowledge of we all need a network, and they stress that in law school. Friend of my professors, I would go to office hours just to chat with them.

I ended up being the research assistant to Joseph Glannon, who’s well known in the lawyer’s world of academia, you know, textbook author, the Glannon Guides we all used at exams. That was a valuable relationship. The contracts professor from whom I had a hard time learning offered me the opportunity to be his contracts teaching assistant the next year and I took it. Because it had been such a challenge for me, I understood him at this point and I thought if I understand why they’re not understanding what he’s teaching, I can bridge that gap. That course had 105 students in it. My office hours were packed every week. My reviews had every student in the class. And by wanting to help others and then also seeing the opportunity to learn contracts even more because I knew at that point I would be practicing at Goodwin and also taking the bar exam, that’s where I made my best friends in law school.

I have two lifelong girlfriends that were from my class and then I can’t tell you how many friends from the class after me from being their contracts teaching assistant, including two of my best friends in the world. One is at Paul Hastings, him and his wife made me the godmother to their baby. The other is at Kirkland, and both of them just helped through law school, helped with their career search, and we ended up making best friends. When I recently decided that I would like to try something new and switch firms, during the time that you and I met that I reached out to Freshwater Counsel, I of course—I’m very open, it was known in the community that I was looking at making this change—and I can’t tell you how many people from various firms, including these two from K&E, from Paul Hastings, a friend at Greenberg Traurig, Ropes—people reached out from all of these law firms offering to help me. Offering “you should come here, I’ll put in a great word with you here.” And these are all people that I met in a capacity of wanting to help them.

So I do think that by trying to advance my own goals and rank as high as I personally could on my own merits without doing anything ugly or dirty, but then also trying to help people, which I also understood was reinforcing my learning, I do think it worked in conjunction to help me achieve academic success and then also building out a really big network.

Khurram Naik: Yeah, that’s a really interesting way to tie the two together. The asset of doing so well is an asset you understood was useful to other people. There was a social benefit to you leveraging your performance.

Patti Burris: Absolutely. And I think that’s completely applicable in the law firm context too. I look at my experience—I’m a rising sixth year now. I’ve been doing this a little while now. And I look at it and I would tell you of course in BigLaw you’ve got to be a wonderful attorney. You have to do great work, you have to be responsive, treat your clients well, be eager to learn, produce a work product that’s consummate with your year and the experience that you have and your billable rate. All of that’s important.

But I think internally, as far as finding support and opportunities for advancement, it’s just as important to be liked. It’s just as important to have a network and to be respected and to be viewed as someone who had people pour into them and then you’ve paid it forward into other people. I think that not only motivates other people to help you—I certainly could not have achieved anything I’ve achieved without people who are far more successful than me wanting to see me succeed. And then I do feel an obligation, no matter how busy it is, to mentor junior attorneys, to mentor law students, to help pay that forward. This is a hard job, but it’s a rewarding job if you have all of the proper supports in place. If you’re leveraging the resources that become available to you that go with a position like this and you’re helping others and you’re still looking to those above you, I think a combination of great work, luck, and being liked is the only way to really thrive in this space.

Khurram Naik: You know, another interesting transition story is the transition from you were in a—so when you worked for the founder that you worked for, at that phase you were raw talent and drive. And so you had things like “I’ll just figure things out.” It wasn’t like you had some bench of expertise, some specialization, that that was your skill and your value to a business. It was “I will figure things out.” And so for yourself, it sounds like with your own career, I maybe I missed it, I didn’t hear any vision for what would come next in your career that you said, “Hey, that’s what I’m aiming towards.” But then it seems like by the time you got to law school you had a very clear and definite vision for where you wanted to go. And I’m inferring, but we can talk about it, that that came from your experience at a fund working with lawyers where you had a sense of the law firms out there because I think few people entering law school would understand with a lot of specificity the firms that have strong ECVC practices or whatever nature of work they’re looking for. Very people had that definite goal in mind. And so what was that transition like for you to go from “I’m good at things, I’m getting feedback I’m good at things, I don’t really know what I’m doing apparently, people are telling me I’m really good at things” to “I have a vision for what comes next”?

Patti Burris: It was—I view that as a privilege. Before I had done everything I had to do to meet the needs of myself and my family. So it was a privilege to finally have enough bandwidth to be able to exhale enough to picture what do I want? What do I want for my life? And what is every experience that I’ve had until this point—what does it make sense to do? There was the whole litigation/corporate analysis, right? And I did enjoy going into the litigation exercises, I was on a moot court team.

But I had this valuable experience from working for a tax attorney when I was 23 years old as his receptionist turned legal assistant, and then moving in-house to one of his clients where I got my bookkeeping experience. I managed multiple entities they owned under one umbrella from a bookkeeping and accounting standpoint to then moving to New England and accidentally getting a job with a brilliant serial entrepreneur and venture capital investor. And it was during that experience that once again, although I was handling a variety of different tasks, I always organically gravitated toward legal. At one point his law firm of record, Burns & Levinson, mistook me for an attorney. They thought I was general counsel based on the way I carried myself, the way I attacked the things we were working on, when I delivered documents to them in the format that I did. And it just—it felt like if you were—if there was a loop throughout all these different phases in life that seem so different, the one constant was that I always leaned legal and it was always in the numbers.

So when I learned about this area of law during my summer at Goodwin, I knew I wanted to do corporate. That—there was no doubt about that. But there now I understand, especially I do teach a course that’s private equity and venture capital transactions, so I’ve given a lot of thought to the specific timeline of a transaction. And all the corporate departments are is “in which part of the transaction do you work?” Like which part of the timeline is your specialty? So I did know I wanted to work on transactions. I had originally due to a mentor that I had at K&E, Amanda Border, she’s a brilliant M&A attorney, I thought—she was a big supporter of mine—I thought perhaps I would do M&A. My summer at Goodwin, as soon as I was exposed to fundraising, that was it for me. That was when I had the aha moment that you’re speaking of, that I have found my purpose.

And it was, you know, so many lawyers, if you tell them you’re going to operate in the world of spreadsheets and numbers and complicated calculations to figure out profits interest and carried interest, they want nothing to do with it. It excited me. I loved it and I still do. There was also the aspect of helping people. I did become a lawyer because I wanted to help people. And you go into BigLaw and there’s this misperception that you’ve sold your soul to the devil and that essentially we operate to help the wealthy get wealthier and that’s the only people we serve. And I don’t view it that way. When you work in funds, many of the large institutional investors represent pension plans and retirement plans. They’ve got Ma and Pa’s money that they’re trying to generate returns on to make sure they’re comfortable in retirement. You have these inspirational first-time fund managers who have these ideas and they’re willing to risk everything and they need you to partner with them.

This systems-driven mindset is something Manisha Sheth has taken to an extraordinary level — she manages 15 to 20 cases simultaneously through strategic delegation and weekly team meetings where everyone from summer associates to partners contributes.

And it’s that closing day where so many people hate closing week and it’s so stressful and you’re not sleeping. And it was my first closing that I worked on as a junior associate—or I guess a summer associate—and of course I’m sleeping, I’m being wined and dined throughout the week, but I’m seeing this process in the most stressful week when everything’s wilding out and everyone is hating their jobs, I was so excited. It was so exciting to see a million moving parts converge at the exact same time. To see them tell this client who had become crazed that we’re closed and that transference to a place of gratitude and even emotion because of all of their hard work coming to fruition. And I thought, “I want to do this. I want to work with this specific area. I want to help people. I want to help these investors close their investment and they’re so excited to be able to participate, but then my clients, the fund sponsors, are so excited that they are participating.” You’re witnessing and facilitating relationship building in real-time, and it really feels like the work that we do matters. So that’s the long, long story to get there. That’s how I decided that’s exactly what I want to do and I will put all of my efforts into pursuing how to do that.

Khurram Naik: So I’m looking at different phases maybe for you. And so maybe the phase where you’re executing on somebody else’s vision very skillfully and discovering things about yourself—so discovering like, “Oh, like, I can run through a brick wall. Like, I—I know that I’m capable of achieving.” I don’t necessarily have a decision yet for what I am looking to do with my career, but I’m satisfied with this, this is already fantastic. Like, I’m very gratified with the progression that I have here and the way that I’m valued here. You know, I know the context for I know that I have an associate’s degree, I don’t even have a bachelor’s degree. I know this is an extraordinary outcome for somebody with those circumstances to achieve, I’ve made the most and the best of this opportunity.

And then, I don’t know if anything was missing for you in that phase, but then you discover, “Oh, I can have a vision for myself” and then work towards that. So like once you said like, “I want to get to Goodwin,” then I’m going to work backwards to make that happen, then you did. So you apply the same skill to to that. Now, you have at this point even more experience, more confidence, and now at this point I’m kind of terrified about what your potential is—I actually just thrilled because I can’t even believe what what impact it will have. But so, what is it now?

Patti Burris: I think what the biggest takeaway has been and what has allowed me to take more risks with pursuing what’s next is I’ve learned through all of this, no matter what happens, I will be okay. And I will thrive in some capacity. And there will always be people who want to help me along. When I made the switch from Goodwin to DLA Piper, it was in furtherance of that goal. I had to really think what’s next. And you know, logically on the timeline that we’re all on from the time you start as an associate, you have a certain number of years as an associate to figure it out if you want to go in-house, be of counsel and continue to practice without having additional responsibilities, or whether you want to go for the partnership. And at this point, I think I do want to go for the partnership.

That’s, you know, I’ve spent all of this time now in school and then all of this time in practice learning the craft, learning the law. And I don’t know everything about the law and I don’t think I ever will, but at this point, I do understand the system of who I can ask, who I can go to, how to find the information that I need. And the next step in a law firm career, partnership, you become the person who’s generating the business. You become the person that your clients are truly partnered with to trust in you to partner with them, to help them advance their goals, the furtherance of their business. And it really becomes a relationship-building exercise and like I said, I think really, if there’s anything in life that I’ve been training for, it’s this. I’m—it is my time to shine.

If it comes down to when you’re ready, the next goal in life is for me to build partnerships with people who have common goals as me, who want to grow and learn together. I’m ready for that, so excited for that. And but at the same time, I have had enough adversity in life that I think I’m wary not to hitch my identity to that. At the same time when it’s my turn to come up to make that decision and I’ve decided “if this is what I want, I would like to be part of the partnership,” there’s also is that the firm’s need? Is there—is there room for me in that capacity? Do they have a need? Do they see a mutual benefit? And it’s possible they don’t. And so at that point, I don’t want to feel like a failure. I don’t want to feel like everything I’ve done until this point in time doesn’t matter. It’s going to be great no matter what.

This next chapter, I’m all about taking care of myself. I leverage the resources that have become available to me in BigLaw that I never had access before to take care of my body, to take care of my mind, to take care of people around me, whether in my family, my friends, or my community. And everything I’m doing, I do with intention. And I have no doubt that whether it leads to partnership or or something else, it will inevitably I’ll continue to be happy and that’s enough for me.

Khurram Naik: You said two things that are very interesting that I’ve been thinking about. So one of them I’ll pick up on is the identity piece and then you then you were just talking about the gratification you get from caring for yourself and people in your life. And so, are you really at a risk of identity being attached to your professional development? Because it seems to me that somehow what’s so interesting is the relationship between your identity and your performance. So like the two of them are separable but feed into each other, it seems like. Where like in law school, you were still a caretaker. You still had other people that you were responsible for, which is extraordinary and extremely difficult in law school. It’s just—it’s enough to take care of yourself at that phase. And so it seems to me that the very challenge—on the one hand, the first thing I think of is challenge, but what maybe is not really appreciated are the benefits that came with that.

And so I you know, I think for myself as a parent, you know, with my son who’s a little more than two and a half, when I—there was a period of time earlier on when he needed diaper changes where I was like, “Oh God,” and so it was just like, “Okay, here we go, I’ve got to change this diaper, get through this.” Now at this phase, every single time—without exaggeration, every single time—it’s like I need to change his diaper is a privilege for me because I know this phase will not last. And it’s something that you just can’t know until you’re in a position like that. And you can do this outside—it doesn’t only have to come from parenting. I think there’s other ways you can get meaning in similar ways where there are things that seem like only downside, only difficulty, only challenge that have these benefits for you and give you gratification. So I wonder for you, did the other responsibilities and other identity you had in law school drive you? Did it give you meaning? What was the relationship between that and your performance in law school which the two are somewhat separate, right? So like, how—what was the relationship between those two and have you had kind of a separation of identity from this professional performance?

Patti Burris: I don’t think so. I think I view my identity as multifaceted and I don’t view it as a pie graph in which the sections of the pie are predefined. I can add sections, I can take them away, I can expand sections. And I do think a common thread throughout all of that: first and foremost, I’m a mother. I’ve lived my entire adult life as a mother. My boys are grown and launched now and I have a grandbaby, but they remain my driving force. They were behind all of the hard nights, all of the times I felt like it was impossible when you have to dig deep into—into strength you don’t even know you have in you. It was the boys. It was my children. It was a desire for them to have more than I did. It was a desire for them not to become statistics of a teen mom or someone who didn’t have an education for most of her life. I wanted equal opportunity for them.

At this point in life, though they are grown and thriving, I still feel an obligation. I am exposed to people in financial situations much better than mine and I see how much of a difference it makes when kids even inherit a house. Something as simple as inheriting a home, how that can change their trajectory. And I want to leave my boys with an inheritance. So that’s still a big driver of pursuing opportunities that inherently have financial benefits to them.

However, I have become a traveler. That’s something new with the BigLaw paycheck. You know, one benefit that seems taboo to talk about or people tend to avoid it is the money. A lot of us are doing this or did this initially for the money. Yes, we also wanted the training, we wanted the exposure to the high-level client work and all the wonderful things you say in an interview when you’re a law student interviewing for a BigLaw position. The travel—this is a hard job. When I’m on trips and I wake up in a country with a culture that’s completely different than mine and it feels like you’re on a different planet, those are opportunities that I would not have but for this job. So that’s a motivator to continue to be excited about my job. Not to view it as something I have to do, but something I get to do.

All of the increased investment in myself. I get massages regularly. I invest heavily in functional medicine, in NAD+ drips and the whole thing. You name it, we do it. In yoga classes. And that’s to take care of my body. I am enjoying the fruits of my labor, but I still have a lot of motivation in me. I still have a lot of hard work left to do, so I want to take care of the vessel that’s doing all of this for everyone. As far as being a lawyer, absolutely that’s part of my identity. I’m proud to tell people that I’m a funds attorney. I’m proud to tell people that I co-lecture a class at BU with Mike Kendall, who’s an absolute just phenom of a human and lawyer. I’m proud of those things. I would have told you—actually, to be honest, I think I was concerned about—and I think you and I talked about this—I was a little bit concerned about my identity leaving Goodwin. Goodwin had been so good to me from the time that I interviewed with them throughout my last day at the firm. It was a safe place for me. It was scary to branch out and do something different. But at the same time, understanding that for the particular opportunity to grow the practice that I was looking to grow, that that group was growing in a different direction than what I really saw for myself.

I did worry about leaving there. I worried, “Will the people at DLA Piper like me? Will I have the opportunities I’ve had at Goodwin? Will they think I’m a good attorney?” So even being a Goodwin attorney I feared was my identity, and maybe now that’s why I look at it a little bit differently. I look at it as a huge part of my life. I’m grateful for them, I always will be, but now I’m a DLA Piper attorney and I’m proud of that too. And I think I could be Patti Burris with her own shingle hanging, or Patti who works at the SEC, and I still view these opportunities and these accomplishments, the identity portion of it, as more what you described: the girl who made all the wrong decisions early on and even created some adversity for herself, but then became an opportunist who could see it, identify it, and make the most out of it. And that’s the biggest part of my identity. I’ve got all of these other drivers. You ask me on any given day whether I’m more hiker, more mom, more lawyer, whatever it may be—more friend, more mentor—all of those are important parts of my identity and I embrace all of them. And I think depending on what season it is, all of them help me grow to be the next version and the next version of that—that pie chart.

Khurram Naik: You said something really interesting, so “the girl who made all the wrong choices.” So that seems to me a story. You’re telling a story, there’s a narrative about this accomplishment you’ve achieved, this narrative arc. And I don’t think anyone listening to you could—could not be thinking about what a skillful storyteller you are. How important are stories for getting us to accomplish our goals?

Patti Burris: Our life is stories. Whether—whether it’s the narrative playing in your head as memories or whether it’s expressing it to other people or whether it’s describing what you want next, a story that hasn’t happened yet—it’s all stories. And I think the narratives that we tell ourselves are huge to our identity and they’re huge to our ability to accomplish and to our capacity to accomplish. Like when I was in law school, imposter syndrome that I think we all have in common—that’s a fear narrative. We’re telling ourselves a fear narrative. And and whether it’s law school or whether it’s in your personal life, in your relationships, your friendships, your—buying a home, whatever it may be—we all have fear narratives. And if you give those narratives too much power, you don’t reach your full potential, you don’t maximize your capacity.

Whereas if you’re telling yourself these same narratives and they’re stories of inspiration or overcoming or accomplishing—we can’t change our past. I can’t change that I became a mother when I was a teenager. I can’t change that I got into a car accident with someone—I got into the car with someone who had been drinking. I had a car accident with that person where I broke my back and 15 other bones that, you know, set me back another few years. I can look at all of those things and beat myself up. I’ve had a failed marriage. I can—I can tell myself I failed. I was a failure. I failed then, I could fail again. Or I can tell myself I failed and I won’t make that mistake again. I learned the lesson the hard way, as I tend to do, but those are some of the most powerful lessons.

So the story that I tell myself is that we all have that kernel inside of us to overcome adversity. We all have it. We all have that belief that we’re something more or we’re something bigger or that we have something great inside of us. And the only two ways that you can test that theory and grow that is either through accomplishing without adversity or with overcoming adversity. And in my life, it’s been overcoming adversity that has convinced me that I can do anything. There’s nothing that I can’t do with the right resources and the right team and the right amount of determination.

Patti’s insight about reframing fear connects to something Hilary Gerzhoy told me — that most ethics violations don’t start with greed, they start with fear. Fear of not making it, fear of losing clients, fear of being left behind.

Khurram Naik: I wonder if you have noticed this, but it seems to me a lot of people that are comparably talented, comparably hard-working, comparably performance-still struggle with meaning and still struggle with a with direction. You can see it in different phases of life in the context of law—you can see it in law school, you can see it after that. I mean, there’s a lot of people who have very serious challenges with trying to make sense of where they are or what—what comes next. I definitely experienced those as a lawyer, for sure. So it seems to me that you’ve consistently been able to hone in on goals and sources of meaning that there’s a nexus between the two of them for you. What have you seen—how can you help other people hone in on that? To hear you talk about the way that you got so excited from your funds work—there’s a number of other talented lawyers who, you know, they consider funds work, the kind of work you do, like you say, kind of punching a clock, or or maybe it’s running against some sort of narrative they have of, you know, you heard it all the time in law school I’m sure—”I didn’t go to law school to do math.” So I mean, like, there’s maybe counter-narratives that people have that are obstacles to them and maybe that’s one problem. But I’m trying to figure out what it is that you can share with people to help comparably talented, hard-working people find more meaning and find better goals for themselves, because it seems to me that’s something that a lot of talented—otherwise talented—people struggle with.

Patti Burris: So I think I’m definitely not qualified to advise other people on this matter because I—I’ve been a train wreck at any number of times in my life, whether anxiety in my own head or externally manifesting, you know, difficult circumstances. But if I said I have to put it into words, I’ll write it in a book or whatever for someone else, I would say the purpose part is—I’m not a religious person. Therefore, I believe this is the one life I know I get. And I’ve been down and I’ve been up and I’ve been everywhere in between. And other than down, it’s been a beautiful ride. If—if it was on the way up and I felt that purpose you’re talking about, it feels good to know what you’re working toward and to hack away at it a little bit of a time. And then when you get the validation at the top, whether it’s the diploma, the class rank, the job you want—that validation is what then supercharges that motivation to that next level and it just feels really great, right? Like we know that scientifically, the serotonin, the dopamine—it’s a proven science.

So as far as the purpose to do that, the way I view it is this is the one life I know I get, I want to live it. I want to know that if something happens to me tomorrow—and it doesn’t even have to be death, I think that’s the one we go to, like cliche, “If I die tomorrow I want to know I made the most of it.” I know what it feels like to wake up and be in a wheelchair and be told you’re never going to walk again. If I wake up tomorrow and I find out I can never use my legs again, I want to make sure that I used them to the best of my ability every day that I had them. I don’t want to know what it feels like to live with that regret. The same of my brain. People that have early-onset Alzheimer’s—think about attorneys, our brain is our capital, this is our well-being. If—if I find myself in a position to receive a diagnosis like that, I want to know that I learned everything that I could, that I taught other people everything that I could, that I made a big difference in people’s lives.

So it doesn’t matter what it is, the specifics of it. So the first part of that, the purpose: I think it’s accepting that we have very limited time here and it’s your responsibility to make this experience what you want it to be. And we all get dealt hard cards sometimes. I will not hold it against anyone for having a hard day, a hard week, a hard year, and even people who’ve had so many hardships that they just can’t continue to do it, and they give in and they quit and they don’t want to do it anymore—I don’t begrudge them that, it is hard. But if you’re able to lean on those around you and you’re able to find that little kernel inside you that still believes you’re great, I do think that you have a big enough purpose to overcome just about anything aside from things other people would do to you, people around you getting sick and dying—there are some things out of our control. I think everything else is a choice, whether it be by affirmative action or omission.

As far as setting goals, I think it is a product of our society and being overstimulated in every way that many of us suffer from some level of anxiety or analysis paralysis. And that’s what I see hang up more law students and young attorneys than anything else is analysis paralysis. Terrified to make the wrong decision. Where it’s been my observation through people that I’ve mentored and my own journey: pick one thing and then stick with it. Don’t get up every day and say “I have to go to work,” get up and say “I get to.” I get to go to work. I have to talk to this client today—I get to. This is an inspiring person who has accomplished things I respect—I get to talk to them. Have a good attitude about what you’re doing and don’t forget to stop trying. Don’t get comfortable.

But I think the issue is the first little hint of “I’m not enjoying this” or “I’m not enjoying my law firm” or “I’m not enjoying the people around me,” we automatically determine we chose wrong and we have to make this huge pivot to something different. And I think a lot of times you can just make a small adjustment. Like for me, it was just “Okay, I need to go somewhere different and do what I do. I’m going to continue to do what I do now for the same types of clients, but somewhere that’s got a little bit different of a future focus for the firm.” That if you hear their trajectory for the group, it doesn’t mean that anyone did anything wrong, you’re just growing in different directions. So I think don’t overhaul things, don’t ascribe to them more importance than they deserve, and then just stay focused on the one thing.

Khurram Naik: Tell me more about this “stay focused on the one thing” concept. I think what you’re talking about is profound and I think the analysis paralysis is probably one of the biggest problems that lawyers face. It’s very acute, I think, for associates and definitely a lot of partners run into this as well because lawyers are overthinking things and then spinning their wheels and then it’s a reason to not act. It gives them an excuse to not act. But what’s really interesting is that you’ve defined yourself as risk-averse and yet I think analysis paralysis flows from risk aversion for most people, where they are working back from the premise of like, “I can’t really make changes, I want changes but it’s really hard for me to do that and I’m fearful of it.” And so then the analysis paralysis I think is the technique they use to procrastinate to avoid making a decision and to stay the course. So how for you do you synthesize your risk aversion with “focus on the one thing” and then, you know, hone in on that?

Patti Burris: So yeah, I do think that’s part of the risk aversion, right? I’ve invested all of this time, it is scary for me to think about doing something different. And at the same time, I can say I thought about making the recent change that I made almost two years prior and stayed out of analysis paralysis and, more specifically, ascribing more weight to what could go wrong than what can go right. So I do think those two things go hand in hand and I do think that’s the hardest thing to overcome. And I think ultimately, that’s where the belief that we talked about earlier—that ultimately I will be okay.

Even if I blow it completely, even if I leave this firm and don’t get a job at this other firm—we tend to go to as humans the worst that can happen instead of what’s likely to happen. Okay, the worst that can happen is—I’ve been pretty smart with my money, I’m good for at least a couple of years. So I don’t get another job at a large firm, a comparable firm, and I have to take a lesser job—or a job that pays less, I don’t want to say there’s no such thing as a lesser job. What’s the worst that can happen? Okay, I make less money. Is that—like, okay, that’s fine, right? Like, that’s absolutely fine, I’m still fine. So I think we just have the—the fear narrative of “I’ll lose everything, I’ll lose being able to tell—being proud of what I do, being able to tell people where I work, I won’t make these huge amounts of money.” And it’s like, “Okay, so what?” Like, what’s the worst that can happen?

We do the same with relationships, right? Like, “This is not working, we’ve tried everything… but if I leave, I’ll never meet anyone, I’ll be alone.” And it’s like, that’s just not likely. So I think a huge part of getting over the analysis paralysis is looking at: What’s the best that can happen? That’s what you’re hoping for, you wouldn’t be going through this analysis in the first place. What’s the worst that can happen? But then most importantly, what’s the most likely thing to happen? And then if you just can’t get there on your own, if you just still go into that worst place, then great, run the analysis. The worst happens—so what actually happens? What are the consequences of the worst? I think at this point in our lives, when people have a law degree in their corner and some experience and presumably at least a few references, your worst-case scenario is that you’re still going to have a badass job doing something that you love. I think there are also the case of people who pivot completely, and I have respect for that too. Like I said, for me it was “I need to recalibrate.” There’s a few misalignments here that are causing me distress, and I think if I recalibrate them I can feel like I’m thriving again and I can find that motivation to shoot high. But then there are people who leave the profession completely. They do law and there are so many that we see on our GO teams at the firm—they learn that actually, they want to be in recruiting. They love helping people. They love exactly what you’re saying—helping people find their purpose. We find people who decide they want to be career coaches. They see the—the mental illness that’s endemic to BigLaw or the proclivity for addiction, and they want to help. They believe they understand it. So I don’t think there’s a bad result. I think it’s just really the analysis paralysis is accepting that you’re going to be okay. So do it. Like, don’t stay in something that doesn’t serve you.

Khurram Naik: What do you see for yourself as the payoff of—you talked about staying in a lane and just like continuing to iterate on that. What do you see as the payoff of—for yourself, what do you see as the payoff of doing that?

The eagerness Patti describes — raising her hand for every opportunity, building relationships by helping others — mirrors what I heard from Ambika Kumar, who was once called “too eager” in a review, only to become the most respected associate at her firm.

Patti Burris: I think the payoff is that you become an expert at something. I think for the most part, at least in the legal world and maybe beyond, we value experts, no matter what it is. You want a nutritionist who understands nutrition, you want a personal trainer who has big muscles, you want a litigator who’s won a lot of cases. We value experts and I do think that’s the one big benefit with staying what you’re doing. If you’re able to recalibrate, whether it be pivot to another role within that world—like we just discussed several within the legal role that aren’t necessarily practicing law—I think if you continue to start over, because I did that for a very long time, not out of choice, you know, but I didn’t find this path. I didn’t go—I didn’t graduate law school until I was 39. I’m 45 years old now. I’m not an expert by any means, but I’m hoping to become one because I do believe that’s the means to the end.

Ultimately, do I love my job? Do I want to work for many, many more years? Of course I do. I love learning, I love going to work, I love seeing people. But ultimately, at the end of the day, I want to hit the numbers that are my goals to be able to leave my children with the legacy that I want to. I want to look back and feel satisfied that I’ve helped enough people, that I’ve mentored enough students and baby attorneys, and I want to feel like I made the most out of the time that’s available to me that I have on this earth. And I think you do that by becoming an expert, by staying the course.

So I do think there are people who have that ability to do anything and they’re jacks of all trades, and you know, we see it with influencers now with—with like the young people who we tell them, “That’s not a great plan, you’ve got to get an education in something and then pursue that path and then put in this hard work,” and it’s like, “Oh, they’re a gazillionaire by the time they’re 21, you know, just for having like a great fashion sense” or whatever it is. So I’m not—it’s not like a one—a one solution, I don’t think there’s one solution for everyone, but I think for the most part, if we’re able to hone a specific skill until we’re viewed as an expert and then you pair that with these other important things that we’re learning, these other important aspects of human interaction, that’s the way to ultimately be successful.

Khurram Naik: Yeah, I think what’s remarkable about your journey is the ability to set understand goals then also achieve them. I think those are two separable skills—some people have one or the other—and you have both, which is very powerful. So can you talk more about the the maybe the tactics, the tools you use for achieving outcomes? And so you talked in law school about the resourcefulness—I mean the resourcefulness to to get BarBri outlines. I mean, so I was—I became a BarBri rep in my first year and then you start talking to your your peers about BarBri and I mean—I just I did it to to learn about BarBri and and they also happened to—the model back then was that you got a free course out of it for for doing it. And it was also very social, so there’s a number of benefits. But anyways, the point is that there’s a lot of education that that we were doing for for because like any number of lawyers in the first year and law students in the first year had no clue that you know what was coming here, understandably, right? And they’re just trying to survive the day. But so you were being resourceful enough to work backwards to say, “Hey, like, if that’s good for learning this in a short period of time, then why couldn’t I use this now?” That’s remarkable.

So I think of tactics like that as being—no matter what your goals are, or even if you don’t know what your goals are, you’ll achieve things and then from there you can—that puts you in a better position to make decisions from there. And so like, let’s say because you used the tools that you have, you graduate top of your class or get into the the kind of job you want. Maybe you don’t know what you’re doing from there, but hey, like, you’re at a pretty good spot to begin with. So let’s talk some more about those techniques because I think that’s very helpful. So the ones you talked about law school, very interested if you have others that you want to share and add, but as a lawyer, what are the kinds of techniques of resourcefulness or tools that you’ve used to level yourself up that you can share that that probably are—are not appreciated or used?

Patti Burris: Um, yeah, so there’s a couple of buckets of that. The primary one being human capital. I will say I approach every analysis the same. I think we tend to overcomplicate things and if we have—whether it’s a goal or a problem, it can be either, they can be interchangeable for this—you have where I am now is right here, and then this is where I want to be, somewhere down the road. If it’s a problem, this is where I am now, this is what I’m solving for. If it’s a goal, this is where I am now, this is where I want to be. The only thing between those two points on the timeline, the only distance between those two things, is a series of actions. And so the analysis is: “If this is where I am, this is what I want to be, what do I have to do to get there?” And that’s usually pretty clear.

If you want to become a lawyer, first thing is you have to get a bachelor’s degree with a decent enough GPA to get into law school. And then you’ve got to do well on your LSAT, you’ve got to go to law school, and then you’re a lawyer. And then from there let’s break it down semester by semester. What is school really? It sounds overwhelming if you look at it as “I need seven years to a law degree.” Don’t look at it like that. A semester is three and a half months long. We’re human beings with incredible potential, we can do anything for three and a half months at a time. If you were qualified enough to get into school, you can be successful for three and a half months at a time. And then you get a good long break and then you just have to do it again.

So I think number one is setting a clear timeline of where you are versus what you want to be. Identifying and defining the goal. Number two is identifying the steps between where you are and to get to that goal. So now you start down that timeline and then what’s the pitfalls? And that’s really what we deal with in a law firm context, right? And it’s like, “Okay, great, this obstacle has now popped up. I was on my path, I understand the goal, I understand what I have to do to get there, but this obstacle has come up.” So now what do we do? We identify resources. What is the problem? Simplify it, put it into words, and then what are the resources required to clear that obstacle? And sometimes there may be something that we don’t have access to, maybe there is a financial need needed to clear that goal and we don’t have access to it. But almost at any point, if you can’t identify a resource that’s easily accessible or which you can access with a moderate amount of effort, ask for help.

If you’re in law school, that’s your professors, that’s your peers, that’s the deans. It doesn’t matter what you’re going through, if you try to do it without help, you’re probably going to fail. In a law firm, it’s a senior associate, it’s a partner. If it’s something substantive that’s law that’s out of your—it’s a specialist, it’s a tax something, it’s a banking, a regulatory. There are people to ask. If it’s something personal you’re going through, you’re not advancing toward the benchmark at the—the rate at which you should, talk to your attorney development manager. Talk to your training team about what trainings are available in the subject in which you’re deficient. If you identify a deficiency, there are ways to solve that deficiency. You just have to break it down into a very clear path of what that is.

And that’s what I mean by human capital. I think most of our problems can be solved by communicating. By the time you’re in a law firm, you have a team. This firm’s invested in you, they’ve put money into you, they’ve put time into you, their clients know you, they want to see you succeed. So if you’re struggling with something, you need only to tell someone and brainstorm it with these other geniuses that you work through who are experiencing the same thing in life that you are. If it’s a parenting thing, talk to another parent at the firm, maybe they’ve got some hack in their routine that you haven’t thought of yet.

So I think most problems can be solved with human capital. From there we have all of these incredible tools available to us now like AI. I automate my life with AI. My challenge right now is time. I want to workout, I want to eat right, I want to have a supplement stack that serves me, but I work a lot. So what do I do? I use ChatGPT. I run ChatGPT, it feeds out my meal plan every week. I eat the same exact thing for breakfast and lunch and I get the variety I want out of dinner. That simplifies shopping, it simplifies planning, it’s giving me the macros that I need for my workouts. I plan my workouts also around my schedule. I’m not logged in until 9:00 AM every day. So I ask ChatGPT, “Plan me workouts.” It tells me exactly what I can do at home or if I have time to get into the gym, what to do there. My supplement stack. I tell it my age, my weight, my physical status of—of how much I can do, how active I am, how sedentary I am at work. It will produce the supplements that most people should take that you can confirm with your doctor. I tell it I have longevity and wellness goals, it suggests additional. There’s no excuse in my mind to suffer.

And I want—I will qualify that to say I’m speaking with great privilege. With with that comment, I’m speaking specifically toward people who are in law firms. I don’t think everyone on the planet has access to everything to make their lives easy. But I think for us, there are innumerable tools to overcome the obstacles using the resources we have available to us. You didn’t have these resources before. So can you go get the new fancy car? Of course you can. Can you go buy the house and be house-rich? Like, sure you can. But I don’t think that makes a lot of sense if you’re not using those same resources to just maximize your quality of life. So I think between communications, human capital, leveraging AI, training materials, there’s nothing that comes up in a law firm context that you can’t overcome.

Khurram Naik: It also seems to me what you’re talking about is—it seems you you’ve had a really strong sense of your values in terms of how you allocate your time, attention, money. And in doing so, that makes it clear to you what you’re willing to sacrifice. Like you are a very social person and I, you know, can just feel the the drive you get from from talking to people and connecting with them. And so it must have been a really difficult thing for you in law school to give up that social time at the end of the week. Blow off some steam, you know, relax. You know, you have so much pressure to just Sidebar’s right around the corner. But to say “I am going to sacrifice that for—for this.” So and then you’re doing it now. Like now you’re fortunate you have significant financial resources and you can allocate that in a variety of ways, but now as well you’re—you’re allocating your time, attention, capital to the things that are highest value to you. Can you talk some about that concept of sacrifice and and how you’ve applied it?

Patti Burris: Sure. I so I think the best way to look at sacrifice is that it’s temporary. I would tie it back to that concept of a semester is only three and a half months. Like, yes, I do want to be at Sidebar with my peers, I want to be bonding, I want to be supercharging my social batteries. But can I sacrifice that for three and a half months and then make up for it over Christmas break? Can I go to—I look at the every Friday Sidebar. Is it really that special versus when you go to Sidebar when everyone finished their final exams? That’s the memorable one, and I would go then. My work here is done, I’m able to celebrate.

Like I said, through focusing on my goals like becoming a contracts TA, I satisfied the social needs that I had that way. So I just view sacrifice as inherent. Anything you hear—it’s cliché but it’s true—anything worth having, there will be some sacrifice. It just can’t be butterflies and rainbows all the time. But it’s temporary. So how big is what I’m being asked to sacrifice? Like what are the effects? Will it have a permanent and lasting effect on my mental well-being, my emotional well-being, or on my family? Then probably not something I’m going to consider doing. Anything else where, you know, maybe I don’t just love that part of my life for a few months—I understand that it leads to the life that I do want, and it doesn’t seem that bad. It just seems like something else you have to do.

Khurram Naik: It seems like two other techniques you use there. One is like focusing on what’s the highest ROI thing to do. So any given week, Sidebar hang, not so high ROI. End of semester Sidebar, very high ROI. So only focus on things that are very high ROI. And then it also seems like you’re stacking things. So like the TA thing accomplished two goals at once. It was developing your your your skill set, it looks good on a resume, and then it was social. So you’re stacking multiple things at once.

Patti Burris: I think so. I think one key to success in both law firm life and your personal life, any aspect of life, is identifying efficiencies. If you can think in terms of strategy and how to combine things and make the most of it, like life just runs easier. And there are limits. It doesn’t mean if you identify and solve an inefficiency that you should then take on another goal and fill that time. And I think that’s where the balance of what you’re talking about with making sure you’re prioritizing what’s important to you.

In law school, a lot of it was just getting by. The kids’ schedules were dynamic, their social lives were dynamic, I was facilitating a lot of that. But once I got into the law firm life, it was a lot more predictable. Even the unpredictability is predictable. You know to expect it. And from there my prioritization—my first couple of years I came in really hot. I suffered the imposter syndrome, constantly scared I would lose the opportunity that had been extended to me. And I billed—I want to say 2,400 and 2,500 hours respectively those first couple of years, it may have been reversed. But even in those times, I operated on a wellness ratio. And this is where being a numbers nerd comes in, but my ratio was 7-2-3-1. 7:2:3:1. And what that stood for was 7 hours of sleep at night—that’s what I need to function at a high capacity. Two healthy meals a day to fuel my body and my mind. Three workouts a week for the same reason. And one thing to look forward to on the weekend so I remember why I do all of this. And I never deviated from that for more than a couple of weeks. The only time I ever reached out and said “boundary, limit, no more, I’m—I need to come off things” was when I was not able to maintain that ratio.

Khurram Naik: And, you know, you are very skillful at stacking things because this is going to be audio-only but people can’t see it, but you’re climbing a mountain right now.

Patti Burris: [Laughs] Absolutely. I love—I love thinking about all of this. I love thinking about and in learning from others. You and I have had so many experiences and you—I understand you’re you’re shedding the focus on me, you invited me to be on your podcast, but a lot of the conversations that you and I have had, I’ve taken away tips for myself. Even though your kids are still younger, there’s insights that you’ve had. And even my thoughts on pivoting careers—you identified something that works better for you and your family. And your posts about how much more satisfied you are in doing what you do now versus when you were this badass litigator. It’s just like—I have so much respect for that. And if you don’t ask people their stories and then really listen to what they’re saying and deciding like, “You know what, I honor that in them. I would like to incorporate that into who I am.” And I think as lawyers we do it with practice. We see a certain way a partner communicates with a client, or even the way someone organizes their to-do list. And I think if we’re constantly learning and open to improving and we’re humble and we don’t believe we’ve got it all figured out, we’ll continue to thrive and grow.

Khurram Naik: I, um, from my time in Boston, near Suffolk, there’s like Emerson, right? And so Ralph Waldo Emerson, a quote of his that I’m not getting quite right is, “Every man I meet in some way is my master.” So there’s just there’s something you can learn from every single person and I—I really tried to practice that way. There’s something you can learn from everyone. So yeah, I think that—sounds like we share that idea. I’ve learned a lot from you and frankly, you have—in our conversations talking about this episode, you know, hearing about some of the tactics you’ve implemented—like you have, Patti, you’ve really leveled up my expectations of myself and said, “Hey, you know, am I really bringing my A-game? Am I really making the most use of my time? Am I really doing the most higher ROI activities? Am I doing three-and-a-half-month sprints?” So you’ve really thrown down the gauntlet for me, so like I—I have my own—well, I’ve thrown down the gauntlet for myself because—because you’ve been very inspirational in that way.

Patti Burris: I really appreciate that. Life is hard. Life is never easy for any of us. And and to believe, in my opinion, that we’ve had any impact on someone, whether it’s making their experience better, more tolerable, whether they feel more loved, more included—those are—those are the biggest compliments that we can receive. It’s to know like I’m struggling through this trying to make the most of mine, and if in any way I can improve your experience, just that much more validating.

Khurram Naik: Yeah, and I think there’s also that concept of, you know, people don’t really remember what you say but how you make them feel. And so—and then a mentor early mine in law said to me, “Hey, you know, as lawyers we’re not really paid for outcomes, you’re really paid for managing clients’ worldview and expectation. You know, we’re really guiding them on what to expect as litigator, our work is inherently unpredictable.” That’s the whole problem litigations—if it was predictable, it wouldn’t be litigation. So yeah, so a big part of what it means to be successful in this work is is that people have mentioned that that there’s so much to learn from you from.

Patti Burris: Absolutely. I agree wholeheartedly.

Khurram Naik: Patti, this is a great episode. I’m so glad that we took the time to to document this and I hope that this is something that people can turn to for inspiration.

Patti Burris: I love that. Thank you so much for having me. And obviously, we will stay in touch and I hope to speak with you again soon.

Her path wasn't conventional. A Canadian law school graduate who was told by recruiters to pursue business development instead of litigation, Priyanka has built her career on being underestimated and using it as fuel. Priyanka lays out how starting as an associate, she leveraged being underestimated to prevail in overlooked opportunities. We also explore the anti-optionality path in law — the competitive advantage in getting good at one thing and sticking with it.

Priyanka talks about what it takes to continue down this path: the sacrifices in her personal life and the challenging and rewarding inner-game of skill mastery.

Keep reading below for the full link to the episode and the full transcript of our conversation.

Top Insights

Below are the highlights of our conversation:

• Mastery is an "Inner Game" of Emotional Energy: Priyanka argues that once a lawyer mastered the fundamentals—the rules of evidence, brief writing, and the nuts and bolts of a cross-examination—the "next level" of performance isn't technical, but internal. Drawing from The Art of Learning by Josh Waitzkin, she explains that mastery requires "inner work" to control your own subconscious and emotions. By mastering her own internal state, she is able to control the "emotional tone of the room," which allows her to manage difficult witnesses and judges with compassion and authority.
• Being Underestimated is a Competitive "Superpower": Throughout her career, Priyanka has leveraged being an underdog to her advantage. From being a graduate of a Canadian law school to being told by recruiters to pursue "business development" instead of litigation, she has consistently been met with low expectations. She treats this as a tactical advantage that allows her to "ambush" opponents. This "element of surprise" works because she maintains a "winning mentality" and keeps "punching" even when those around her suggest the case is unwinnable.
• The Fallacy of "Balance" and the Power of Being "All-In": Priyanka rejects the concept of "work-life balance" as a myth that doesn't apply to high-stakes litigation. Instead, she advocates for "calling a spade a spade"—being radically honest about the sacrifices required for exceptional outcomes. She believes in being "all-in," arguing that you cannot achieve mastery if you have one foot out the door (the trap of "optionality"). By committing her "heart" as well as her "hands" to her clients, she is able to channel a level of emotional energy and creativity into her cases that a less-invested lawyer simply cannot match.

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Full Transcript

Khurram Naik: Okay Priyanka, I am very excited to have you on here. It's been so much fun to have our calls to set up some background on your history and your trajectory here. I'm excited to jump into your episode.

Priyanka Timblo: Khurram, it is a pleasure to be on with you. I have had a blast in our last couple of chats getting to know you, talking about my story, and thinking about my story—whatever that is. I know that whatever is going to come out over the next hour is also going to be somewhat new, so I’m excited to see how this goes and how it evolves.

Khurram Naik: Okay, so we'll jump in from the beginning, because I think the chronology is really interesting. So, you're an associate, you're at Paul Weiss, you have a very strong litigation practice, and you're comfortable. You're doing well there, you could keep on cruising along, but you assessed that there was something missing and then you did something about it. So, what was missing and what did you do about it?

Priyanka Timblo: The thing that was missing was I felt like I wasn't getting to practice and demonstrate the thing I was best at, which is being on my feet, arguing on my feet, taking witnesses—that sort of stand-up lawyering. I say that with some trepidation because I was getting so much else. I learned what excellent lawyering looks like there. I was able to work with incredible lawyers. I was able to understand litigation soup to nuts, right? All parts of discovery. I would not be the lawyer I am today without all the incredible training I got there, and the mentorship and friendships that I still have today.

But through that—and I think part of it was that on the hard days, it just felt like my trajectory was a bit off, so to speak. I wasn't getting to do the thing that I'm best at. I was getting to do things I'm good at—I’m very good at managing discovery and managing large document productions and second-chairing depositions—and I'm good at all that stuff. I love it. It made me the lawyer I am today. But I didn't feel like my trajectory was on track to be the kind of lawyer that in my heart I felt like that was what I wanted to do. I wanted to be a trial lawyer. And it almost felt like a ridiculous thing to hope for because it's BigLaw, right? Like, nobody gets those experiences. What are you talking about? If you're doing well at what you're doing, that's great.

There was a very loud voice in my head that said you should just be really grateful for the amazing experiences that you're having and the relationships you're having, and this other thing that you want is pie in the sky. But I think it kept gnawing at me. I had an experience which was the New York State Bar Association Antitrust training course. It was like a three-day trial training course. Paul Weiss, being really committed to developing their associates, offered an opportunity for me and some others to go and do this. I went, and it was literally practicing direct examinations and cross-examinations. They would record you on video doing them, and there would be a panel of very accomplished antitrust trial lawyers watching you.

So, you got two sets of feedback: feedback from the people in the room watching you do your mock direct or mock cross—and by the way, mock opening and mock closing—and then you got to take that recording and go into a room with another very accomplished antitrust trial lawyer who was not one of the ones who just saw you, and watch your tape. So, I guess I got a little taste of it, and once you taste blood you can't go back. But also, I got some feedback that I actually "have this." Not only did it feel natural, but I looked natural. And then that was like, okay, I gotta—this is my one wild and precious life, what am I doing with it? It inspired me to say if I'm going to work these hours and I'm going to do this law thing, then let me try to put myself in a place where I'm doing more of the part of it that makes me come alive, which are those witness examinations—standing up and speaking extemporaneously to some extent, but also prepared, having to think on my feet.

I had gotten this feedback that I had the promise, and that sort of confirmed to me what I knew about my own skill set. That was where I made a choice that I said I think I need to—as amazing as my experience in BigLaw has been, and again, that is where I saw what excellent lawyering looked like and that is a standard that I have in my head from Paul Weiss because there are just incredible, excellent lawyers—I said to myself, I got to find a place that's smaller where they're just going to give me more opportunities. It's not quite the BigLaw structure, and I'm going to be able to actually take a deposition, actually argue in court, and maybe actually do a trial one day. And even that felt like a pipe dream at the time.

Khurram Naik: So how did you make that happen? Once you assessed, "Okay, I need to find a place that's going to set me up to exercise this skill set," how did you implement that?

Priyanka Timblo: I found a recruiter. I actually talked to several. And you know, I'll say this, not every recruiter is supportive. I went to a Canadian law school, I had a great clerkship from Canada, but it wasn't an American law school and it wasn't a federal clerkship. I literally had someone tell me, "You should look for like a biz-dev job. You should be off-track to that." I mean, that was told to me. So I actually had to find someone who believed in me, and I did. They were not the most experienced person, but I was like, "This person believes in me and this is who I'm going to go with."

Khurram Naik: And then, so when you're evaluating firms then, what was your criteria? You knew that you wanted to get some trial exposure, but what else led you ultimately to Holwell?

Priyanka Timblo: I didn't know about it myself independently; it was my recruiter that suggested it, and credit to him. When I looked it up, I was like, "This seems really cool." It’s new. This was 2017 at the time, and Holwell Shuster & Goldberg was founded in 2012, so it’s five years in. It’s a baby firm. That appealed to me a lot. I loved the fact that it was founded by a judge. And then I kind of went online and looked at some of the partners and they seemed on the younger side. I found that exciting too. I said, "This place looks like it’s special or different."

And then I went in, and my first interview was with Judge Holwell. I will tell you this: I came out of that interview saying if they give me an offer, I’m going to take it. Just because I could tell that this was personal to him, founding this firm. And the conversation that we had was more about how you think about the law and why you love it. I think he even talked about finding the "golden thread" between cases when you finally done enough research, and how exciting that moment is. I was like, "I want to be with these people." And that was just after meeting him.

Then I came back for a full round after that, and I met with two partners and two associates. The two associates I met with at that time are now partners. Coming out of that, I was even more convinced. These people are all incredibly accomplished beyond belief and they could go anywhere, but they chose to come here and start something somewhat untested, five years in, a new boutique, when I'm sure they could go to any law firm, any BigLaw firm, and be partners. But they're coming here, there's just something fun and magnetic. One of the partners I met with, Vince Levy at the time, he said, "Look, this is just—it's got a startup feel to it. That's a bit of what we're doing." And I loved that too because I want to be all-in on everything I do, and I got the sense that all these really smart people who could go out and do anything else were all-in. I was like, "I love that. I want to do it here."

Khurram Naik: So with that startup construct, there's potentially a lot of upside and then some significant downside in that there's riskiness in a startup. Paul Weiss is a very established franchise. This new firm, you know, people are very pedigreed and to your point that people can go anywhere, that also cuts in the direction of: well, they could just go anywhere. If this isn't a success, they can just go anywhere. I ran into a very similar situation in law school; there was a small firm that I joined that was one of the few that was hiring—I entered law school in 2010 so it was a really rough economy. One of the things I assessed was: yeah, these lawyers are all very tough, they came from very big firms, they could go anywhere they want, and that's part of the risk of coming here, that it wouldn't really hold them down here. So for you, how did you titrate the risks and benefits? How did that seem like a fit for you?

Priyanka Timblo: I love a risk. That's just my personality. I mean it—like, it's more fun if it's a bit risky, and it's more in line with who I am. So yeah, that was hugely attractive. The potential for failure. [Laughs] To be clear, what I saw were these incredibly smart, strong, confident people that are badasses and I was like, I'm very comfortable betting on this.

Khurram Naik: Yeah, and look, I've seen in the people I've interviewed on this podcast, this is a very common pattern where lawyers have joined a growing franchise and said, "Okay, there's a lot of upside here and so I'm going to get in on the ground floor here." So say like Neil Chatterjee, he was at Orrick and then he helped build out the Silicon Valley office, this brand new tiny office, and there's these like internet weirdos in the 90s doing interesting things and he's like, "Okay, that was an opportunity that he saw a lot of upside in." Kalpana Srinivasan at Susman, she joined the growing small LA office, a firm that's largely Houston present, wasn't a big firm. You see again and again that people who take established but small and growing firms with the right DNA, there's a lot of upside potential to that.

So very early in, you got an opportunity to handle an arbitration that seems to me to be a major inflection point in your career. Can you talk about that?

Priyanka Timblo: Absolutely. So this was about a year into my tenure as an associate at HSG. It was a call from a friend—one of the people you've interviewed on your show, and I won't say more than that—but he gave me a call and said, "We have this arbitration." It was calling from in-house saying we want someone to handle this for us. Obviously, it's not like I had some great reputation as a lawyer that they were calling Priyanka for Priyanka's skill set. It was the firm, and I was the contact at the firm and known to him.

It was not a massive arbitration and it went from filing a complaint to the hearing in like seven months. So, good speed. And I basically got to first-chair it as a mid-to-senior level associate. I got support—I absolutely got support—Judge Holwell himself helped me with many aspects of it. It was also where I started working with Brendan DeMay, who is one of my partners here, and he and I would later go on to do another very large breach of contract case together, the Walmart case, which came later. But that was my first experience working with him.

It was really awesome because the nice thing about an arbitration sometimes is you are handling it from complaint to hearing. So every single part of the litigation process—which in the large complex cases that you typically see in BigLaw or even high-stakes litigation boutiques, they span years—but here you have a seven-month time frame. And I got to handle every single part of it. And that process makes you a better litigator. How does your complaint play out when you have discovery? How do your discovery requests play out? What kind of motions are you making, if any? What are the right things in your deposition? What are the admissions you're getting in your deposition that actually become effective control on cross?

And so I got to do my first direct, my first cross, actually leading the show. My first sort of full argument on it for the post-hearing argument on the issue. And it was a tough case. I don't think there was a lot of confidence, just given the posture, given the legal issues, that anyone thought it was an obvious win. I think there was a sense that it was very unlikely that we were going to win. And so I learned this other really critical skill: you need to do your best and leave it all on the table and just put it out there even when everyone around you is sometimes telling you you're going to lose. How do you do that? And that has been probably one of the most critical skills I've learned how to do in my life and that has been responsible for my success thus far. And I learned it then. And we won. It was a close call, but we won. We got over the edge because we made the better legal arguments and put on the better evidence and we were up against very accomplished, very fine lawyers.

Khurram Naik: If someone didn't believe in themselves in that moment—a skilled lawyer who didn't believe they could win and was listening to other people who said this will not win—what would that lawyer have done differently than what you did?

Priyanka Timblo: I kept working as hard as I could and I kept thinking about creative ways to win. I kept the winning mentality in my head. I kept asking myself: how do we win? What do I do next? And I think if you have a defeatist mentality or "I've already lost" mentality, you're like, "Well, how do I just like get through this?" Not, "Let me think of the next creative idea. Let me figure out what's the next punch I throw." You're not thinking that. You're like, "Let me cover my head and go and cower and wait for this to be over."

But if you stop punching, then you're not going to win. And so it's that attitude that even if they land a few blows or even if people are telling you you're not going to win because your opponent's way bigger or whatever the other thing is, as long as you never give up the actual task of figuring out what's the next strategy I have to do every single day and every moment of the trial to win, that's the mentality that will help you get there no matter what is being said. And even if there's a part of you that accepts that this is going to be hard.

Khurram Naik: I recently read a book by Edward Thorp, who is a legend in breaking down how to build systems around poker and how to beat casinos once you understand the odds better, and then he wrote a book about how he did that in the context of investing. He said, to paraphrase, "Once you know there's a way to solve a problem, that does the heavy lifting of solving a problem." Once you've decided that a problem's solvable or understood to be solvable, then that does the heavy lifting. That sounds like what you're saying here. That attitude, that mental shift, that spurs all this creativity and drive that just the equally talented person would not implement. I think that sounds like the differentiator.

Priyanka Timblo: I think that's exactly right. Once you figure out there's a way to solve the problem. I really like that. The other part of this is that I think I'm used to being underestimated, and that's really served me very well.

Khurram Naik: What are some examples of that?

Priyanka Timblo: Well, I wouldn't say that they "paid off," but I'm used to operating in a circumstance where I'm being underestimated. I'm used to operating as the underdog and not having that get to me. Not having that take over my mentality or take over my focus on winning or my belief that I can win.

It’s all of it. You enter into a BigLaw class at a place like—at any BigLaw firm—and there's like a hundred summers in the class. I went to the Canadian law school, and a lot of people had fancy clerkships and much more fancy law school and fancy connections and fancy parents who are prominent lawyers and all of that. And it’s easy to feel underestimated a lot of the time. And as soon as someone new works with you, what do they do? They look up your bio and they go to your law school and they may think, "Oh, I haven't heard of that one," or "This person, I don't know if they're going to do their best work for me." So I am used to having to prove myself with every single person again and again and again.

I know I'm coming into it from people having low expectations. That may not be very true anymore, actually, at this point in my career, but that is how it started, where it was like, okay, they're not thinking they're going to get the best from me. And what I do get is I get the element of surprise. I get to ambush someone and prove that. And that's fun, and it works. But I think more to go back to what you were saying earlier, I am used to operating under those conditions. I am used to being underestimated and I am being used to being told that I'm not the winner, I'm not the lucky one who's going to make it.

Priyanka’s decision to leave BigLaw for more courtroom time is strikingly similar to what Randy Gaw did — he left after an 11-month trial in San Diego convinced him he’d never get first-chair work on the partnership track.

Khurram Naik: I'm noticing a pattern of two aspects. One is selecting opportunities—how you selected Holwell, how you signed up for this arbitration and identified the upside there. There's upside to Holwell; there's upside to this arbitration; you could lose, but there's some upside if you won. So that seems to be a big part of it. Your attitude seems to be a part of it of just having that resourcefulness of "let me figure out how to make this a win."

So a question I have for you is, you've identified this arbitration, you saw an opportunity there, like you were saying, an arbitration is this small, defined universe where you can really own it in a tractable amount of time. Every aspect of discovery you get, evidence, it all comes together for strength. There's a lot of lawyers who are early in their careers who are thinking about when they think about the opportunities they want. I see patterns of two ways of thinking. One is—and frankly, this was absolutely true for me when I was a mid-level associate—I was at a middle-market firm and we were doing good work, but then I saw an opportunity to do—we weren't the—we were often in joint defense groups and we weren't taking the lead. And so there were certain firms that were taking the lead in these kinds of cases. My former firm was one of them. And so I said, okay, that's a firm I want to go to.

So there was a size of case that I wanted, a type of case. There's definitely a lot of merit to taking on those big cases. But something I didn't appreciate going from a middle-market firm to an AmLaw 20 firm is that what often goes along with that is with these big cases that are high stakes, there's also a lot more top-down direction, including from the client often. Clients are sending work that's of two natures: one is they have pretty definite ideas about how it should be litigated, and others are more matters of first impression relying on you for this. By contrast with middle-market clients, they are growing and they're sophisticated enough, but they don't have the expertise in-house to make directions, so they're really leaning on you as a counselor.

So I see a lot of people making selections or interested in identifying new opportunities at firms or within their firms based on the "stake" of the work. Often people are thinking about "I want a higher stake kind of dispute." And so you're making the case for, hey, you know, there's a lot of value in these smaller transactions. Do you observe this to be a pattern? Do you think these are relatively overlooked opportunities, underrated opportunities? How do you think about, at this stage now, or how would you advise somebody who is a mid-level associate? How do you advise them to think about the size of an opportunity? Because I think so many people are focusing on "bigger," but you know, it sounds like there's potential benefit in "smaller." I wonder if you can talk about that.

Priyanka Timblo: I think that this is a really excellent question because I think there's a lot of associates—and I was one of them, and I know other associates do—are always weighing that. There's the amazing marquee high-stakes case that the firm has that you could be a part of, but it's very top-down, and those are larger teams. Or there's like a small case where there's more room for you to control things and direct the action. And what I would say is you need both.

You need to have the smaller cases to show what you got and to take control and to learn all the little parts of litigation that need to come together seamlessly to become a really smart litigator. Especially to become a trial lawyer, you need to know how all the parts of litigation work, the stages of it. Small cases can teach you that really well because they move faster, and because the teams are smaller. So you will be more involved in each one of those stages and so you will get a critical learning experience. And the other part of this is you will get more—you may get more time to shine. If it's a smaller team, you may get to do a witness or you may get to lead. Those kinds of things. And so that is super valuable. And I would actually encourage mid-level associates to seek that out.

But—and this is a really important "but" because I truly believe this—the big high-stakes matters are also really important because you learn how you litigate those differently. You learn how to work as part of a very large team. Potentially not only as part of a large team but as part of like one law firm working with many other law firms jointly toward a goal, and how to negotiate those relationships and how to manage these enormous cases, which is a different skill set. If you want to do complex commercial litigation at the highest level, you do need to learn how to manage those big cases and you need to learn how they work and their nuts and bolts and how to succeed and how to shine and become a star even on a team like that, a large case and a team like that, but also how to sort of respect the structure and the framework and certainly the various business interests that are at play.

So it's almost like the smaller cases are a crucible of learning, but if you only do that and you don't have the experience on the big ones, then at some point it's going to be harder to shift over. And so that's where the diversity of cases is critical. And if you've had just the small cases with one or two partners and you're arguing stuff and taking witnesses and writing all your own briefs, that's awesome. You've got incredible experience. But working on the big cases, the huge high-stakes ones, the ones that make the news—that's a different skill set and, depending on what your career goals are, it might be really important to be a part of that too and have that experience.

Khurram Naik: In that case, what's wrong with just pursuing—let's say you just have total ownership over arbitrations, then. Let's paint a picture where that's a skill set you start acquiring as an associate, you get mastery of these arbitrations, and then that's a pathway to partnership to say, "Hey, like, I am a go-to person for, say, arbitrations." And then that's my thesis, and I also develop systems and patterns around this—it's very operationalized. That seems to be one vision of success, and you're charting a different success which is based on much more diversity of skill set and versatility. Paint the different paths for someone who pursued maybe—I guess you could say there's three paths: only the biggest cases and trying to figure out how to do those well, doing a mixture, or doing just smaller cases where you have mastery. What are those different paths as an associate to partnership and then as a partner for growing from there? How would someone know which vision is best for them?

Priyanka Timblo: So I'll address the first question because the second one is much harder: how which one is right for you. But I think one perspective that is just critical to have is that life is long and careers are long. It's easy as an associate to think of partnership as the end, but it is not the end. Partnership is what I call "table stakes." You gotta get there to start playing in the big leagues. It's starting. You're not ending there. And then you have to—once you're there, now you have table stakes, then you build your career.

And so, but I also think it depends on the area of law, it depends on the firm that you have, and it depends on what you want out of your practice. It really is personal and specific. And so if you are at—and I think that one thing about litigation, at least litigation in New York, though, is that a top litigator is expected to be able to do both. Like you are expected to be able to help manage and run very large cases where there's lots of different law firms involved and joint defense groups and all of that. You have to know how to do that, and that's its own skill set. And if the client's like, "I just have this really important matter and it's small and it's going to trial in six months and it's like one partner and two associates," you gotta need to have the skill set to do that. And so you need to understand who your clients are and what's the practice you want, and that should inform the mix.

I think there are some firms and some practices where you can say like, "This is all I do and I am really good at it." Right? "I do arbitrations in this forum that are exactly like this type, and I know everything there is to know about it." And I love what you said before about process—you perfected the process and you're super efficient and like you are the go-to person if they have that kind of dispute about around this size. And that's phenomenal. That is a ticket to amazing success. But that's your practice then. That's who you are. And like I said, once you're like firmly embedded in that, can you branch out ten years into being a partner? Probably, but it's going to be harder once you get pigeonholed.

And so I—from my vantage point, which is the one that I can speak to, which is a commercial litigation boutique in New York that often works opposite and alongside BigLaw, we do a lot of the same kinds of cases—to me, it is essential to have the ability to do both. The big marquee, huge high-stakes, headline cases and the small arbitrations where it's a really tiny team and you got to perfect your process and be able to do it. And so it would be very difficult for me to counsel an associate not to seek out both kinds of opportunities unless they were sure that they wanted to be like exactly this type of lawyer forever. If they told me that I'd be like, "Go for it, you figured it out."

I've heard the term "optionality" a lot in your podcast. And it's—that's not the way that I necessarily think of it, but I think of it as like: I want to just do different stuff because I don't want to just do the same thing for a long time. I want to keep my options open for a new adventure and a new type of case. And the way I keep my options open for a new adventure and a new type of case is to make sure that I always—that I have versatility in my skill set. And that I'm doing different types of cases of different sizes. And one really critical thing of part of that that I'm super proud of in my practice is the plaintiff and defense side work. Being on both sides of the V. That has made me the lawyer I am and it is super fun. And it’s rare from what I've heard.

This inner game of mastery — controlling your emotions and being authentic under pressure — is exactly what Joe Ahmad has spent over 100 trials refining. He told me juries are the ultimate “phony detectors.”

Khurram Naik: Yeah, it's interesting you mention the optionality because that was something I was going to pick up with you on because I did sense that your thesis is very different in that way. So it sounds like you believe in optionality in that you want to be well-rounded as a litigator, both sides of the V, small cases, big cases. But it seems like you've made a very specific bet on the kind of professional you want to be. Your counsel for law students and having an understanding of what they're heading into, wanting—your counsel for them is like, "Hey, do you want to be a lawyer? Like, you have to understand you're making a very specific bet here." And so that to me said that, oh, okay, I'd be interested in talking to Priyanka about optionality because it sounds like she's more a believer in making a call and a concentrated bet. Arguably you did that with HSG, arguably you did that with saying, "Hey, let's take that first arbitration." So I'm very interested in hearing your anti-optionality thesis, which is interesting because of course you could also make an assertion that it does include some optionality in that diversity of skill set. But it sounds like you're more a believer of calling your shots.

Priyanka Timblo: I think that is really insightful, and I almost didn't realize that about myself until you said it. So thank you. Because I think it's true. I think that's exactly who I am. I—and part of it is because I want to be all-in. And when I'm all-in, it is all-in. I am devoted. I am 100% there. When I am on a case serving a client, and I've said this to my clients and it is 100% true, I'm like, "I want to win just as bad as you do." And sometimes they're like, "Really? As bad as I do?" and I'm like, "Yes, as bad as you do."

I want to be all-in and I don't want to have one foot out the door. That doesn't work for me because I need that framework of being all-in to channel my best work. Because my best work is not just the legal ideas and the hours and the strategy; it is my emotional energy and my heart. And that I'm thinking about those things all the time. I'm thinking about them when I am going for a run or making breakfast or something like that. And I want that. I want it to all be my life's work. And so you can't—you gotta be all-in for that kind of stuff.

It’s the way—I think the way I would put it is: that’s how I know I work best. That’s how I know—that’s what makes my work fun, right? When I am all-in and I get to be all-in. And so—and I don't want to work these hours and do this if it's not fun and I'm not putting my best in. So I just—I need to place my bet, commit to something, and then—and then that's it. Like, I'm in it for the long haul. And by the way, it's not that I'm—I'm not the kind of person who deludes myself into thinking, "Oh, well, the inevitable path is success on any given thing." I don't think that at all, actually. Defeat has been a friend and a teacher in my life. So—but you're all-in. And you're all-in for the losses, too. But yeah, I think it is—it's just part of who—part of my personality and what makes this fun for me, I would say.

Khurram Naik: I think you're hitting on something really perceptive, really insightful, which is that "all-in" aspect is—I think you could reconcile—so I myself happen to be a believer in optionality. I find it to be a useful perspective. But I think there's a resolution of the two which is: when you're in something—you could be doing something for the optionality of it in your career, maybe your thesis is "Hey, being partner at a firm is a tool that I'll use to get to other things," fine. But when you are doing it, you need to be all-in.

And I think that any number of lawyers view some step in their career, some role typically at a firm, as a stepping stone to the next thing, which is fine, but I think then they don't—they're not invested in that step. And so they're just not going to get what they need to get out of that to get to the next thing, unless you're totally invested in it. It was so interesting how you said "heart" because I learned this concept from an entrepreneur named Dan Martell, and he's had this concept of "hearts and hands," which I find really helpful.

So there are times in a business when you need hands; there's just tasks to perform, and you want tasks performed well, but maybe you need a specialist—let's say with my business, my podcast is not central to my business, it's something that I do because I like to do it. It definitely has a relationship to my business, but that's not the thing. And so I'm not going to have someone who's like a full-time dedicated person who's thinking about the podcast 24 hours a day. But so for that I need hands. But then for other things you need hearts, right? You need someone who's invested.

So it's so interesting you use the word "heart" because that's exactly this new idea that I've been exploring about being all-in. And yeah, I think that's a really powerful idea for making the most of the stage you're in. And then if you want a more clinical concept for it, Andrew Huberman—a very popular writer about performance and well-being—just had a tweet, I think it was yesterday, about compartmentalizing. He said, you know, this gets a bad rap, but in order to have success, you need to be at some moment of the day, when you're doing something, you need to be able to compartmentalize that. And so I think that's—if you want to take a more analytical approach if "the heart" doesn't resonate, that's another way of getting at the same concept.

Priyanka Timblo: Yeah, firstly, I love Andrew Huberman too and I listen to him a lot, so I’m really happy to hear about that. And I think compartmentalizing is right. I also don't think—you know, I love the way you put it, which is that there is resolution between the two perspectives of optionality versus anti-optionality because it is—and compartmentalization is that resolution. Because when you're in it, be in it, right? And maybe there's a point where that is done and then there is another step for you to take, another path for you to take that opens up. But you can't always be—you can't be looking at all the options and surveying them and have your fingers in so many pies to the extent that that sacrifices your focus and commitment to the thing in front of you.

Khurram Naik: On the topic of heart, so we talked about how any number of lawyers at different stages of career—let's say particularly mid-level litigators who have some sense or lawyers who have some sense of what their interests are at that stage—something I've observed is a lot of lawyers at that stage are thinking about the kinds of work they're most interested in. I think there's definitely a lot of truth on the topic of heart, that you have to have an interest in something. You need to be thinking about it—so for me, my measure was what I think about in the shower. And so I noticed of myself when I practiced law that, no, I'm not thinking about my cases in the shower or on the weekends. And so I knew it was like, okay, that's not a great sign. That's a measure of when you've really hit your stride and you're really honing in on the thing you should be working on.

So I think one dimension we talked about: these big cases, small cases. That's one dimension. I think another dimension that a lot of lawyers focus on is practice area. And so again, understandably, some practice areas are just inherently more interesting than others. But I've noticed that I think an underrated lens on choosing work is the control or what you learn from it. I think in relative terms, what's overrated is focusing on practice area and saying, "Oh, this is what I'm most interested in," because I think that overlooks how you litigate those cases or do that work. But I wonder what your take on that is: what's the role of substantive interest in a practice area for choosing and then what role specialization plays in your career, either as a litigator who's coming up to partner or as a partner? Because I think that's something that can be very confusing for people to wrap their heads around.

Priyanka Timblo: You know, I totally agree. And I think that was very confusing for me as an associate. And one great thing about the firm that I am at is that we just—we are generalists and we are very firm about being generalists, within commercial litigation. So, only commercial litigation all day, but within that, we do a lot.

But you cannot lose the need to go deep. So I do a lot of antitrust work. And I love antitrust work and I've been doing that my entire career, starting at Paul Weiss. And antitrust is one area of the law like you can't be a dabbler, and you can't wake up tomorrow and decide to be an antitrust lawyer. You have to have spent quite a while reading all those cases from last century and the tweaks on it and understanding the nuances in the doctrine and understanding the philosophy and also exactly how it's changed over time. Like, "this case changed the boat for this," and "this case changed the landscape for this kind of claim," or "these kinds of claims are going to become easier," or "this state's going to pass a statute and now all of a sudden it's going to completely change the ballgame for plaintiffs with a certain other type of claim," right?

And you need to have the facility, having read those cases, having read the doctrine, and worked with economists also, by the way, because antitrust law is a dialogue between law and economics—and just like the pure economics of it—and you need to understand how they speak to each other to really be able to practice it at a high level. And so that's an area where I—like, you can call yourself a generalist all day, but you want to do antitrust law, you gotta read the cases and you gotta spend a long time kind of becoming to that point.

But I read a book last month that was really interesting, and it’s called The Art of Learning by Josh Waitzkin, who was a prodigy chess player—I don’t know if you’ve heard of him, he…

Khurram Naik: Yeah, I read this book. I think about it. I'm interested in what you have to say about it.

Priyanka Timblo: Oh, I'm so glad you've read it! Anyway, it was one of those books where I was like, "Wow, I have so much to think about." And the thesis of that book was that the people who perform at the very highest level of their fields—versus they're not just great, they have achieved mastery—those people have more in common with each other across radically different fields than they do with people in their same fields one layer below. So the masters have more in common with the masters in a completely different field than they do with the greats in their own field.

And a lot of that has to do—I mean when you talk about specialization, right? I think about that a lot because it's having—it's taking your craft and what you're learning to the very next level. And this goes beyond—one of the things that is talked about in that book, as you know, he talks a lot about chess in the book because he's a chess player. And when you get to that level of greatness—I’m not even talking about the mastery level—the greatness is you know how to play chess really well. You know all the rules, you know how it works, it's like you've got the nuts and bolts down. Amazing. But how do you rise above?

And to me, this is a bit of a nuance on specialization because it's like you have to internalize your craft. You have to take your craft and then make it one with yourself, basically. And he calls it—the way that I interpret or what I learned or took away from the book was it's like: you have to learn the fundamentals and master the fundamentals so that you can leave them and rise above them and make it your own and have your own distinct style that is so authentic. And that is like a level of new mastery within the same craft.

And so in law, it's not just about this area of the law—like I was just talking about antitrust law. You gotta read all the cases, you gotta know the economics, you gotta do all that—yes, totally. And you gotta respect that this is its own doctrine and you have to do the learning and do the homework. You don't wake up tomorrow being an antitrust lawyer. But then there's the craft of being a lawyer, which is really why I love trial law. Because even after you know how to write a really good cross-examination and do a really good cross-examination, each one comes out a little different, and you must have a learner's mentality.

The way that you get better is often at that point, when you know you know the material inside out, when you know you know how to write and deliver a good cross, how do you get better at that? And the way you get better at that, I think, is almost to go inside yourself and say what—like, what are the personal things in my emotion, in my subconscious, that are not obstacles, but that are influencing my style and creating obstacles? And so you actually have to fix those to become better. And I think you and I talked about this in one of our prep calls. I think about that very specifically because right now I'm in a really cool spot where I do a lot of different arbitrations month after month. And so I'm doing a lot of opening and closing statements and directs and crosses, and what's great is I get to do them and then I get to do them again in a month. So there is this unique opportunity to say: how do I get better, right? And how do I hone the craft and rise above to that level from greatness to mastery?

And a lot of that work that I've had to do to move forward has been understanding for myself, how do I control the emotional tone of the room more? Which involves me being far more in control of my own emotions. Now that's big work. That's like the deep work I have to go do, but that is the next level. That’s the next level in a cross. And so when you say specialization, my mind is going there in a way, too. It’s going there as much as it’s going to antitrust law and reading the doctrine. It’s like honing your craft and having a learning mindset always. And that learning mindset, as you get higher and higher up that ladder—when you've mastered those fundamentals—the way you ascend beyond that is to know yourself more and to control the things that are invisible.

Priyanka’s honesty about sacrifice — the real cost of missing her kids’ first week of school for trial — is a perspective Patti Burris approaches from a different angle. She developed a 7:2:3:1 wellness ratio to protect her non-negotiables even while billing 2,400 hours.

Khurram Naik: You know, it's so interesting because I—it was my birthday yesterday and so for birthday I mostly took the day off. And I sat down to read a book on Shakespeare that I've been meaning to read for a while. Something—so I've liked Shakespeare, I've read his works, but I haven't really understood the historical significance fully. And so, in doing a little more research on it, it seems like one of the big innovations Shakespeare had—he took existing works and then modified them. One of the patterns is my understanding that he modified, say, Greek plays. These Greek plays did such an interesting job of characters wrestling with conflicts with the world. But one of the innovations he had was he took things that—the Greek conception for that conflict was it was much more about society, much more about, "Hey, how do my values line up with society?" And then how that's tactically implemented in a play is you have a Greek chorus who are communicating the expectations of the society and contextualizing this individual's decisions in the context of society or religious concepts like fate. And what Shakespeare's innovation was: to internalize that. So something that otherwise would have been given to a Greek chorus is now come through a monologue. Like Hamlet gives a monologue and that's communicating the stakes, and so much of it was more about the internal struggles and internal conflicts between conflicts of values that people have.

So it just seems to me like that was like the big bang of the modern era is realizing that the real game is internal. Maybe you make an economic explanation of it—Shakespeare was in a time of kind of the inflection point of economic growth in our society, and so once we have certain material needs met in a Maslow hierarchy kind of way, then the game becomes inner, right? So then that's where the craft comes in. Craft is no longer "how well do you build a chair," but now the craft is like "how well do you relate to others and your own strengths." And that's, like in a service economy, that's what craft is. I'm finding that for myself, you know, as I'm kind of referencing—as a litigator, I enjoyed so much about litigation, patent litigation, antitrust too—I only took a course in it in law school and I loved it so much that I asked the professor to introduce me to antitrust professors. This is in 2012, and so he's like, "You know, unfortunately antitrust law's kind of dead right now, so it's kind of all been decided." It was like, "Oh, well, there goes that." If I just hung in there, there would have been a lot for me.

But so—I definitely enjoyed it analytically for sure, but I hadn't identified a craft in it. And I think a big part of craft is not just what exists in the world, they say, "Ah, there's the craft, I go do that." You create craft. You pull it out of the world and say, "Ah, here I'm going to create my own path here. I'm going to create the craft that I'm honing in on." And I think that's—when you say you're identifying—like for myself, you know, in recruiting, what I'm really enjoying is the structure that we create. That's what I'm really fascinated by is, you know, when you're in this market-making function, you create structure for firms, for lawyers, and I'm really fascinated with that and the implications of that. But no one's going to tell you that. That's not like some thing that someone's going to tell you, and just like when you're saying, "Hey, I have to master this emotional dimension." You're not going to learn that in law school. You're not going to get that—there's not going to be a speaker that's going to come in at your law firm and say, "Hey, let's talk about the emotional energy game here." Like, these are things that you have to identify that of all the different pieces there are in life, "Here's the thing that I'm honing in on that I'm identifying."

So do you feel like there was a moment where you discovered that's what you have to do? Like how did you come to realize the game isn't just about the skills of cross-examination and "Okay, here's how to craft effective written discovery" and "Here's how to frame this." How did you realize that you were at that point where it's a different game now—it's a game of interiority, it's a game of emotional energy management?

Priyanka Timblo: I think it's a great question, but I cannot let what you just said pass without saying how impressed I am that you read Shakespeare yesterday on your birthday. That's awesome. I haven't read Shakespeare in years, but I loved it and it shaped me to what I am today. Anyone can do it; it's free. It is, it is.

In any event, so your question about how did I discover—firstly, the premise of your question is the critical one, which is that it is on you to discover the craft. And to discover—like the guidebook isn't showing you what the next steps are, right? There is no book that says first you do this, and then you do this, and then you do this, and then to get to this level, that's your next step. Even if you read The Art of Learning by Josh Waitzkin—whoa, that book is heavy and deep and complex and at some points I have to read the sentence five times because the concept is so ephemeral and hard to pin down.

So what I'll say is this: as a younger lawyer, one of the things that I was always attuned to was when I saw something that some other lawyer did that was awesome, right? That killed it. Like a freaking awesome brief. There's a ton of guidance out there on how to write a very competent and very good brief, and everybody should read that guidance and learn it and we can all get there. But like, then there are some people who just have the talent—like one of my partners, Brendan DeMay—it’s like his briefs are just otherworldly. You know? And he just does it so well and it’s just mellifluous when you read it. And so when I look at that, I soak it in because I’m like, that’s some genius at work. And you gotta take a moment to honor the craft when you see it at that highest level, because it creates an imprint in your mind of what excellence—like that mastery—is supposed to look like. And it’s important because you have to have that ideal floating around. You have to start creating—building the ideal starts early. And so what I would say is you should always be on the lookout for those moments of magic when you see them in other people.

And then with your own—when I was, especially as an associate, you have to master the fundamentals. It’s almost like to respect work that is magic and hits that point, you have to respect the fundamentals and respect the discipline of mastering first just like—get a handle, clean up your house. Figure out exactly how to do this stuff from the ground up, really well. Learn the building blocks, learn the skills. Because you can't get to those top levels unless your mastery of the fundamental principles is not only complete, but it is profound and it is so within you and a part of you and natural—that’s when you can leave it and go to the next level.

What I would say is like with cross-examination, I remember before I had to do my first cross I bought the books and I watched videos and I read everything that I could possibly read about how to do a good cross. And I practiced that and I learned rules. And I could teach someone some really good rules on how to do a competent cross. Anyone can do it, I promise, if you follow the rules. And you gotta learn how to first write a competent cross and what the rules are, and then you have to learn how to control a witness and what works and what doesn't, and you got a few missteps and you figure that out.

And then the next level of that, once you know how to do all that, is controlling the emotional tone of the room. And again, I've actually seen that done really successfully. One of my other partners, Scott Danner, just has an innate talent where he—it's just his personality, it's who he is. He's able to control the emotional tone of the room—of the judge and the witness and opposing counsel and everybody else—and he's the one in charge, but it's done with compassion. And so there's just massive control in that and massive mastery.

Here's the thing: I'll never be able to do it the way he does it, and I'll never be able to write a brief the way Brendan does it. And so this part where you get from "I know the fundamentals" to "How do I figure out the—like, what my next steps are for mastery?" Again, it's that going interior. It's: who am I? How—because you can't copy someone else. It's just impossible. It has to be authentic or you're not getting there. And so you've got to flip it back around and go internally once you've mastered the fundamentals and say: having mastered this, how do I take a risk? And how do I get myself into like a mindset of flow where I can take a risk and that risk is awesome?

Again, this goes back to the book I keep mentioning, The Art of Learning, where it's coming from your subconscious. You're channeling the power of your subconscious which has the body of everything you've learned. And that—like, risks that come from there are coming from your mastery of the subject matter and the craft over a long period of time. And once you take a few of those, you're like, "This is fun, and I can do this." And that gives you the confidence to take others. And you know which ones make sense and which ones don't. And you know when you're ready to take that particular risk in a given moment because you're not always ready. And by "ready," I mean like you have better days and worse days—we all do. So to me, you know, it starts with the fundamentals and it starts with the respect for the people who do it really well. And then when you have mastered the fundamentals, you've got to go inside and figure out how to bring that subconscious, how to bring that part of you that is uniquely you into the next stage.

The boutique culture Priyanka describes — where she got first-chair opportunities early — is something Rakesh Kilaru also found at Wilkinson Stekloff, a firm built around team-based growth and creating space for younger lawyers to lead.

Khurram Naik: I think this ties into that question of specialization too—like, should I work on big cases, small cases, should I work on this antitrust or some other practice area? I think the answer is: there's a dynamic relationship, a reciprocal relationship between the type of work and the craft. And you have to be constantly identifying: "What is my craft?" and then "What's the best substrate for exercising that craft?" If my craft is how I control the emotions that I have and therefore influence people in a room, you can't be doing that if your work is like literally by yourself by a computer, right? When you're briefing or whatever, you can't exercise that skill set. So you're choosing the wrong work if you're trying to make that your craft. And then if there's cases that don't go to trial, you won't be able to use that skill set. So there are constraints from the work that guide the craft and vice versa, but you have to be looking for like—what is that? You use the word "flow"—how do I get in flow with the work and my craft?

Priyanka Timblo: Absolutely. I mean there's just like so much of, you know, I think we've talked a lot about what happens when you're in the right place at the right time, but how do you get to the right place at the right time? And that has been gaining people's trust, building true relationships, and therefore getting to work on the right types of cases, being able to take on cases with a ton of risk that give you opportunities early on. And that's how I've gotten trial experience and that's how I've been able to build it. So it is directly related to my appetite for risk.

Khurram Naik: So you talked about, you know, you developed a relationship with a litigation funder and that was so influential in your trajectory. What was the nature of that relationship? Why—I mean, yes, your firm was selected, but there's other—you're in New York City, right? So there's just outstanding firms there. So clearly you were a key part of this, that you had this relationship with this person at this fund. So how do people grow those kinds of relationships? What is it that you did that was special? Again, this funder, he knows lots of lawyers. What was it in you that—what was the kernel that that grew? And how can other people cultivate that sort of organic relationship with someone?

Priyanka Timblo: So the key word is "organic." And because I—like this notion—firstly, I will speak to the fact that I'm a fairly junior partner, so when I talk about biz-dev it is talked about from my perspective and the things I know. There's a million ways to do this right, and I only know the ways I did it. In my experience, there is almost no difference between—like what business development is—is building authentic long-term relationships of trust with people where they have many opportunities to see your work. To see your work, to learn your work, and to trust your work. And that's when they come to you.

Of course there's some amazing lawyers out there where their reputation precedes them and they're going to get the cold call. But me, how I got here, it's the true work of building—and I have to use the word—friendships. Because when someone comes to you where they're taking risk and they want—they trust you—like, that trust runs really deep. It's trust in competence, so they've seen your work, they've seen results, and they've seen your character. And usually, though not always, but at least in my experience, there's a friendship that is with that. That is real. It's not just like business colleagues. Sometimes things like networking and biz-dev, there's a shallowness to that, right? That doesn't need to be. And I'm not implying that there always is, but that's sometimes why I shy away from those words and why I'm not afraid of the word "friendship" in those contexts.

Because I do believe to your point, okay, so we're talking concretely about for example the Walmart case that my firm took on, that Brendan and I took on, and that we won a $101 million jury verdict in Arkansas against Walmart in 2024. And it's this massive case and it came to me with a phone call from a friend who knew my work and where we had a relationship of trust. Where—and part of that trust—is that I think that—well you'll have to talk to him—but part of it I know is that he knew that I go all-in. In the sense of like: I will do my best. I want to win just as bad as anybody else does. There's no principal-agent problem here, if you know what I mean. There's no daylight between our intentions because I am not the kind of person who does that. Because when I sign up, I am all-in and I will make—I will do my very, very best. And so what I would say to your question of how does one come about to develop those relationships: it's the long way. It's the way you make lifelong friends. It's by coming to someone authentically, being there for—you know, building authentic relationships incrementally over time. This was many years in the making. Finding opportunities to work together where they can see your work, trust your work, trust your competence, and see your character as a lawyer and your character as a person. Because that's—I think that doesn't get talked about enough: values and character. It's not just like brain power that's the thing people want. They want someone who—and it's not just brain power and legal ethics. Those are important, but I'm talking about something else, which is character. Like, the staying power, the commitment, the heart, the ability to get past tough situations, to work with people on something. And sometimes complex, difficult cases, that's what's needed as much as anything else. And so that relationship was in place at the time that I got that call and why we were the right people for that case.

Khurram Naik: So that outcome is remarkable because it's one of the largest jury verdicts in Arkansas and it's against Walmart which is, you know, this what I understand to be a beloved retailer and institution in Arkansas. So this seemed to be heroic—heroically against the odds and then an extraordinary outcome from that. So there was Priyanka before—you know, the litigator heading into that experience—and there was Priyanka after. What was the change?

Priyanka Timblo: It definitely changed my profile and it changed—you know, more people knew who I was, right? And a little bit of—like, I wasn't totally underestimated every time I entered a room anymore. So that's been nice, but also maybe I'm losing my superpower on that one, to harken back to our previous conversation. But actually, here's the thing: I look at that also as: what can I learn from it? Because we should be learning—it's one milestone on the journey of improving my craft.

And so I look back and I can think of like, you know, when I wrote some of those crosses, I took risks and I did them really differently than—I sort of tried something totally new out, you know, with some of them. And I'm proud of how it worked out because it worked out really well. And then I'm like, okay, well the answer is not to obviously do the same kind of strategy for the next cross; it's to trust myself to be creative and inventive with crosses.

Just to give you an example: one of our witnesses at that trial was a very, very high-up, sophisticated, polished Walmart executive. You know, just totally—one of these people who has control over every word. Like, and I had deposed her several months earlier, about a half year earlier, and she was a very difficult person to depose because she wasn't giving anything up but she was like not confrontational at all. Just like, ask her a simple question, you get a long speech that isn't responsive but it’s like all the right buzzwords. It’s like: this is a very savvy and intelligent person. And I was like, she is not going to agree to a damn thing that I try to do with her on cross. I'm going to say something, I'm going to get a speech. And that is ineffective on cross. And then you try to argue with the witness—you have lost. Period. The minute on cross-examination you are arguing with a witness, you have lost control and you have lost that game.

And so I was like, "How am I going to do this?" And so I thought: I'm going to get through her just—a critical issue in the case was like whether the folks, the higher-up folks including her at Walmart, were aware of what some of the lower-level employees were doing on the deal. And their claim was, "We weren't aware at all, the employees went rogue." And so my entire cross was built around a series of like 30 emails that were all update emails, where the lower-level employee was updating her and a few other Walmart people. And the questions were literally: "You received this email. You and four other Walmart executives, including two Walmart lawyers, on this date." "You received this email. That was one week after the last email. You and five other Walmart executives and four other lawyers." "Now you received this email. This is only two weeks after that. You and six other Walmart executives and five other lawyers."

And you can see how the answer to each of those questions has to be "Yes," right? And she didn't have the ability to give me a speech. And it built a momentum and I did this for like a lot of emails. And that number kept going up, by the way. All of a sudden it was like "You and 14 other Walmart executives and five lawyers." It was weekly, and it’s like—you’re creating an impression. And I was—nobody taught me how to do that strategy, but I came up with it. And I was like, "That was fun, and that worked." And like, this was a very tricky witness who is one of the smartest people who was like, believe me, any question that gave her wiggle room, she was going to wiggle.

So I look at that and I say: what can I learn from that? And what I can learn is like: difficult witnesses call for very creative solutions and I need to trust my gut and always be super creative and do something brand new and cool. And so perhaps the greatest gift of that victory and that experience was the affirmation that my crazy creative ideas work sometimes and having the confidence to do them again. And so that is what I take from it. And I get to do more of that and sometimes I see myself like getting more risk-averse, "Oh, let me just write it this way," and then I'm like, "No, that's not—that's not where my power lies, that's not what difficult cases call for." And so the Priyanka after the Walmart verdict is more proven in concept, I would say.

Khurram Naik: I love that. And you have more confidence in your creativity. I’m thinking of like Star Wars, the original movie, and he's got the ghost of Obi-Wan in his ear and it's like, "You know, just use the Force, let go." And so I think that was your moment there.

So let's talk about, you know, on the topic of trials. You did something that is extraordinary, where you had a trial where you're eight and a half months pregnant. I've never been eight and a half months pregnant, but that sounds very difficult. So tell me about how you've managed to weave in parenting with the demands of your work. Tell me about how, at the level of performance you're operating at, how you manage.

Priyanka Timblo: So the first thing I will say is it looks nothing like the word "balance." The word "balance" does not apply. I don't understand what—it just—that is alien to my life. It is sort of moving from one mode to another. When I am in trial for my clients, I am all-in on that. And I do try to call my kids every day, but I still have to be all-in in the trial and I just need to—I make sure that they are being cared for, that they have their routine. There's a lot of setup I do before then to make sure that they have what they need. But I have to be able to pull away for trials. And so I make sure that I can because the last thing I want to do is feel pulled between two directions.

I will also say that some days I feel like I'm not managing. I need to say that because I think there's a lot of working parents out there and especially working lawyers where it's just painfully hard. And it just is. It is painfully hard and I feel like I am drowning some days. And those are the moments where you have to say—take a deep breath—and why am I doing this to myself? You gotta ask yourself. And the answer is because I love my career and I love what I do and I am so lucky to get to live this life and do what I do for work. And I am so lucky to get to live this life and have two amazing kids that bring me joy every day. And it is really hard right now in this moment today, but I just sort of need to get past this really hard moment, right? Even when I feel like I'm drowning and even when I feel like I'm failing everybody, and get up tomorrow and try again.

So, you know, there is sometimes when I just don't feel like I'm managing. So to anyone else who feels that way, you're not alone. But I will say in the long run, I've gotten comfortable with it. And the reason I've got—I don't feel—I think very early on when my kids were much younger, I felt a lot of conflict and resentment toward my career because I couldn't spend as much time with them. But I don't feel resentment anymore. That's not a feeling that I feel. Because I'm very clear about why I do what I do with my career. And I'm also very clear that it's my choice. I chose this. This is for me. And I love it and I am grateful to be walking my path every day. And this is exactly where I'm supposed to be. And I gotta do it, and I'm also supposed to be Iris and Orion's mom and that's my path too. And however hard it looks and however unconventional it looks, I gotta work through this difficulty. And this is the hardest thing I do. I will tell you that doing my job is much easier than navigating or managing doing this job while making sure I'm being the parent that they deserve.

Khurram Naik: How do you think about, you know, what I think I've heard a couple successful people talk about this construct: what are you willing to sacrifice for success? Because you cannot have exceptional outcomes if you don't sacrifice something. And so how do you think about that on, say, a monthly time horizon, a year time horizon, or a quarter time horizon? Like how do you think about: "This is what I'm sacrificing for this payoff"?

Priyanka Timblo: I think you need to call a spade a spade and know that you're sacrificing it and don't mince words. That to me—that has been more helpful than anything than like pretending I'm not sacrificing it or pretending like, "Oh, this isn't going to affect them at all and it's totally okay for me to miss the first week of school because I'm in trial." Like, no. I'm making a sacrifice and it sucks for them. But I am devoted to my client and their outcomes. And I need to be there for my client that week. And I worked in the weeks before to set it up so my kids had everything there and I sat them down and I talked to them and I made sure that they could be—everything could go as well as it could that week.

But yeah, no, it's a total sacrifice. And to me, as long as I'm calling a spade a spade and seeing that it's a sacrifice and even acknowledging that, yeah, maybe they weren't best placed that week to not have me there, but—but—I am not there because I am choosing. No one is forcing me; I am choosing to be there for what I need to be there for my client. And that's really important to me too because, like I told you, I'm all-in and when I'm devoted to a client and their needs and their outcome, I am devoted to their needs and their outcome. And so, you know, I just—being very blunt and clear and realistic with myself that I am making those sacrifices is easier than pretending that everything's okay.

Khurram Naik: Now on the topic of being all-in, so you've had this extraordinary win last year, and now you're a little less of the underdog now—maybe you're the "overdog." So now, on the time horizon, let's say about a year—in the timespan of say a year from now, what is it that you're most excited about? Your progress, or a year from now looking back, what do you expect to be looking back with pride on in this coming year?

Priyanka Timblo: This has been an amazing year. There's a sense like, "Oh my god, after the Walmart win, am I ever going to do fun stuff again?" and it's just been the opposite. Like I said, this year I've been on trial like six or seven times, you know, and I've gotten an opportunity to do like examinations in very close proximity in slightly smaller settings. And that has presented a very unique opportunity for me to hone my craft and to evolve as a lawyer and to also deep—deepen my knowledge of antitrust law, which I have done.

And here's the other part of it: it's also making me—you know, the work that I was talking about earlier how you've got to like go into yourself and do the inner work to become better at your craft? To become better at my craft, I've been doing more inner work, I've been doing more meditation, doing more reading, actually putting those things into practice. And so this feels like a year where, even though I've been working immensely hard, I've actually been caring for myself and improving my own abilities to be resilient and strong along with it, as part of the work. And so doing the work and doing the work at this higher level is making me a stronger person and a better mom and a happier person. I mean, not no "Mom of the Year" awards for the mom who missed the first week of school, believe me, but you know, I actually—looking back at this year, it's looked completely different than, you know, the year of the Walmart verdict, but it's had its own set of extreme challenges. But I've gotten to really, you know, in trying to master my craft and get better at it, get to know myself more. And that feels like the right moment to do that because I'm about to turn 40. And that feels like a milestone too.

Khurram Naik: Well, we're at time, Priyanka. This is amazing. We could definitely go for probably another two hours, but I know you have many other demands on your time. But this was incredible and I hope we'll revisit this—you'll come back on in the coming years.

Priyanka Timblo: Khurram, this was a true pleasure. Loved getting to know you in this process. It's really fun to talk back and forth with someone who is so well-read and who has thought so deeply about some of this really high-level fuzzy stuff that is hard to pin down. So it's been a unique pleasure and thank you, I'm honored to be on.

We also discuss how he researched and considered precedent for the recent Kadrey v. Meta decision on fair use in generative AI.

Any lawyer looking for an original approach to career decisions and how they practice should listen to this episode.

Keep reading below for the full link to the episode and the full transcript of our conversation.

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Top Insights

Below are the highlights of our conversation:

• Public Service as the North Star: Judge Chhabria’s entire career, from his time at the San Francisco City Attorney's Office to his current role on the bench, is defined by a deep commitment to the public interest. He emphasizes that a district judge’s greatest service is to move cases along efficiently and transparently so that justice is not hindered by undue delay.
• Plain Language and Accessibility: One of Judge Chhabria’s core beliefs is that for the law to be legitimate, it must be understandable. This drives his unique writing style—characterized by directness and brevity. He encourages writing for the "sophisticated non-lawyer" to ensure that judicial decisions are accessible to the public they serve.
• Hiring for Character (The "Nice People" Rule): In a field often associated with "sharp elbows" and extreme competitiveness, the Judge prioritizes hiring law clerks who are simply nice. He finds that creating a collegial, collaborative environment in chambers not only produces better work but also yields clerks who are more successful in their long-term careers, including at the Supreme Court.

Full Transcript

Khurram Naik: Judge Chhabria, thanks for joining. This is a really great opportunity to share your experience, so I’m excited to have you on.

Judge Chhabria: Oh yeah, thank you for having me.

Khurram Naik: So, I want to start with your experience in the San Francisco City Attorney's Office and what you had shared previously, which is that you had chosen to go to that office, which was somewhat of a surprising departure given some of the experiences you had and credentials you had. I’d like to hear a little more about the decision that led you to join that office.

Judge Chhabria: Yeah. I mean, I will say that nowadays, going to a place like the San Francisco City Attorney's Office is not really the road less traveled. I mean, it's much more well-known, a sought-after job nowadays given all the work that the San Francisco City Attorney's Office has done and other city attorneys' offices have done across the country over the last decade or so. But back in, let's see, what was it, 2004 or 2005, when I was deciding what to do after spending a couple of years at my law firm in San Francisco, I was doing white-collar practice in the law firm, and so the natural next step for somebody who wants to go into public service who does white-collar stuff at a firm is to go to the U.S. Attorney's Office. Or at least it was back in those days.

And so I did apply to the U.S. Attorney's Office thinking that this would be a cool way to go into public service. I didn't hear back from the U.S. Attorney's Office for quite a while, and so that got me to sort of think more broadly about why I went to law school, what I might want to do with my law degree, and how I would want to serve the public. And what I realized eventually is that although being an Assistant U.S. Attorney is a great job and you can really accomplish a lot if you do that job responsibly, it wasn't really why I went to law school. I went to law school to be involved in kind of constitutional public policy type issues that were important to the community.

And so I started looking around and stumbled upon the City Attorney's Office in San Francisco. And in particular, I discovered the government litigation team in the City Attorney's Office. That team was responsible for defending constitutional and other type challenges to city policies, city laws, and city policies. And they were also doing the marriage equality litigation; they were challenging California's statutory ban on same-sex marriage. And so all of that stuff really appealed to me. Once I learned more about the office, I realized that this is precisely the kind of job that I went to law school to get. And so I applied there and quickly got hired by them and it was really the best career decision I ever made to go to the City Attorney's Office after my time at the law firm.

Khurram Naik: Can you say more about what—you had some expectations to get out of the experience and then you probably gained things that were surprising out of it. So what surprised you about your time in the office?

Judge Chhabria: I guess the variety is one of the things that really surprised me. Like I said, I went to this team where the primary duty was to defend challenges to city policies. But our office also had started a robust affirmative litigation practice. The city attorney, Dennis Herrera, started the affirmative litigation task force, which consisted of lawyers from different teams all across the office, and I joined that task force and got involved in affirmative litigation.

There was the marriage equality litigation as I mentioned. And so in the City Attorney's Office—it’s both a city and a county—the government does a lot of stuff. There were almost, I think, 200 lawyers in the office when I was there, and every issue under the sun comes within the purview of the City Attorney's Office. There was the land use team, the healthcare team, the tax team, the code enforcement team, the labor and employment team, the trial team—which does a lot of your bread-and-butter trial work defending police officers or, you know, the bus runs over somebody or whatever and there's a lawsuit about it. There's a team out at the airport that does legal issues relating to the airport. Any number of different teams and any number of different legal issues. And so it's like if you're into public policy and local government and law, you're like a kid in a candy store. There's going to be something interesting for you in the City Attorney's Office. So that really surprised me and it was also one of the really cool things about the job.

Khurram Naik: Is it the case—I mean you described a very generalist practice and Article III courts are courts of limited jurisdiction, but there’s still a generalist variety of the nature of the work you work on. Do you see a pretty straightforward connection between the generalist variety of the practice in the Attorney's Office and then the impact that had on the bench? I’m curious about the ways in which your experience there prepared you for the bench.

Judge Chhabria: Yeah, it is kind of similar. One of the other things that I did in the City Attorney's Office is I became the Chief of Appellate Litigation. And so in that capacity, I'm overseeing the appeals in all of our cases coming from all of our teams. So I was able to dabble in a lot of different areas of law and learn about a lot of different areas of law, and this job is very similar in that you'll look at securities cases and civil rights cases and intellectual property cases, constitutional cases, employment discrimination cases, etc., etc. And oftentimes the case will present an issue that you've never had to deal with before and you've never learned about before. And so I do think there was a parallel from my old job to my new one in that respect.

Khurram Naik: And then, at least historically, there wasn't a very tried-and-true path from the City Attorney's Office to an Article III role. Can you talk about that path and is it becoming more common now? Tell me some more about that transition.

Judge Chhabria: Yeah. Well, I think that back when I went to the City Attorney's Office, I never really planned on becoming a judge and it was never my goal to become a judge. I think if it had been my goal, I would have gone to the U.S. Attorney's Office, right? Because back then, it was so common for prosecutors and BigLaw people to get put on the bench. I mean the federal bench was filled primarily with federal prosecutors and BigLaw people. And so—but like I said, that's not something that was on my mind back then. I was focused on doing the job that would be most interesting and most fulfilling for me.

But as it turns out, that decision probably contributed to my ultimately becoming a federal judge. Because in Obama's second term, they started focusing really heavily on experiential diversity, and that's something that continued in the Biden administration. And I think they realized, starting in Obama's second term, that we have too many former federal prosecutors and BigLaw people on the bench and we need experiential diversity. We need people who have had different work experiences and come at it with different perspectives. And so they started looking for defenders, they started looking for people who maybe were solo practitioners—I mean somebody who was nominated with me and had her confirmation hearing with me was a solo practitioner—and local government lawyers. And so I think that actually my professional experience, once I decided to apply for the bench, my professional experience was a benefit. And you know, that's just something that you can never predict, but it turned out well in that regard.

Khurram Naik: What changed your mind about taking an interest in becoming a federal judge?

Judge Chhabria: Well, I don't know if it's so much that I changed my mind, it's just something that I never particularly thought about or had as a goal. I always thought that I would be one of those Washington policy lawyer types who kind of bounced in and out of administrations and was involved in federal policymaking and federal legal issues. I also thought that I always assumed that I would be working on stuff that would be too controversial to allow me to become a federal judge. And certainly at the time that was true of marriage equality, right? Back in 2005, when lawyers who worked in favor of marriage equality, that was sort of considered a strike on their resume probably from the standpoint of getting on the bench.

Judge Chhabria’s path from the City Attorney’s office to the federal bench is one way government service shapes a career — Manisha Sheth took another, moving between elite private practice and the New York Attorney General’s office twice.

But eventually the tide turned. And once the tide turned, I remember that the folks from the South Asian Bar Association approached me about whether I would be interested in applying for the bench. And in particular, the head of SABA Northern California at the time, Karen Jan, raised the issue with me. I think she was the first person ever to raise this issue with me and kind of encouraged me to apply and was a big supporter of mine throughout the process. And when she did raise it with me, I thought, "Hey, that actually would be really cool, maybe I should think about that," and I put my name in not too long after that.

Khurram Naik: What did you think would be cool?

Judge Chhabria: Well, I did clerk for three years in the federal courts, and so I had a sense of what a fun and rewarding job it could be. And one of the things that's great about it, we already discussed, right? It's that you get a bunch of interesting issues and it's constantly new stuff and you're constantly having to deal with new challenges and learn new issues and decide new issues. And so it's stimulating in that respect.

The other thing is that it is rewarding. It very much feels, particularly I will say at the district court level, it feels like if you are rolling up your sleeves and doing a good job on a day-to-day basis, you are making a contribution to the community. It might not be some giant mega-contribution, but in little ways, whether it's how you're dealing with sentencing, criminal sentencing, or how you're deciding cases or how you're managing the cases. If you do a good job, you're making a positive contribution to the community. And so that was what—and I had that sense before I applied because of having clerked here. And so that's what made the job attractive to me.

Khurram Naik: And now you're more than 10 years into the role. What’s surprised you the most about the role?

Judge Chhabria: Probably a couple of different things. Number one is I assumed when I started that a pretty high percentage of the motions would only have one reasonable answer. That precedent would dictate the answer in most of the motions, and reasonable judges could not disagree on the answer. That is certainly true of some motions, but I would say it's a much lower percentage. I think I probably assumed that was going to be like 80% of the motions and it's probably closer to 40%. So that means on most of the motions, reasonable judges could disagree on the outcome of the motion. And so it's more challenging than expected and probably more rewarding than I expected too because again, if you do a good job and you think you're getting the right answer, you're making a contribution.

So that's one. The other thing that really surprised me was I was expecting the civil case management part of the job to be boring. And I listened, you had a great interview with Judge Koh-Nelli a while ago, and he talked a lot about case management. You could tell from the way he was talking about it that he found it rewarding too and that he understood that if you do a really good job managing the cases, that is one way in which you're making a really positive contribution to justice and to the community. And I sort of expected when I came into it that it would be just more a case of housekeeping and setting dates and kind of this mundane scheduling stuff. But then I realized, largely for the reasons discussed by Judge Koh-Nelli, that how you manage the case really has an impact on how things go for the litigants, the cost of the litigation for the litigants, and whether justice is being served, frankly. So I have found the case management side of things to be quite rewarding, and that was a big surprise for me.

Khurram Naik: So I think it might be interesting to talk about your process for your work product, your opinions, because a lot of practitioners I talk to—a number of whom I've interviewed previously—there's a very clear consensus among them that your opinions are notably more direct and often shorter than other federal judges. And so what process would another federal judge, let's say a federal judge new to the bench, use to communicate like you?

Judge Chhabria: Well, I think, you know, I go back to when I first started the job, and I think that part of this comes from the public service focus. I mean, I came from a public service job and I view this, again, as a public service job. It's a gold-plated public service job—people are like opening the door for you and stuff like that—but it is: we are here to figure out the best way to serve the public. So when I started, and even before I started, I really thought carefully about what's the best way as a district judge to serve the public.

And I think an underrated way of doing that is moving the docket along, moving the cases along quickly, not protecting against undue delay. There are circuit judges who have more time to ponder these issues really deeply and take a long time to write long opinions and all that. But if we treated the cases like circuit judges would, we as district judges would be doing a disservice to the public, I think, because the parties need to get an answer from you on the legal issue that they've teed up in front of you so that they can decide how to proceed. Whether they can decide whether to settle or whether to go to trial or whether to appeal or whether to change a policy or whatever the case may be.

And so I always thought an underrated part of serving the public well in this job is moving the cases along. And so I designed the system within chambers largely with that in mind. So what that means is that we don't have bench memos. We don't do bench memos here where the law clerk lays out the arguments being made by both sides and discusses the case law and then makes a recommendation. I sort of thought that is probably in most cases a waste of time. Instead, we sit down, usually on a Monday, to discuss the hearings that are coming up on Thursday. Sometimes we'll sit down earlier, but usually it's on a Monday and I often will not have started reading the materials yet. If it's a big case, I will already have started reading the materials, but often I will not have started reading the materials yet.

And the law clerks will just start presenting the cases to me, telling me what the issues are, identifying the key cases that I need to make sure to read and the key evidence that I need to make sure to look at, etc., etc. And they will give me a sort of help me strategize for how to prepare for the hearing. And then I'll start reading the briefs and the cases and the papers and stuff like that and I'll circle back with the law clerks and ask follow-up questions: what about this, what about that, etc. And then that's how we prepare for the hearing.

We might also decide that we don't need a hearing and we'll vacate the hearing and decide it on the papers if it's an easy case. And then after the hearing, and usually shortly after the hearing, we will issue a very short ruling, right? And we use the term "MemDispo" here. You know, in the Ninth Circuit, the Ninth Circuit will do two types of rulings: they'll do published opinions and they'll do unpublished memorandum dispositions. And the unpublished memorandum disposition is usually a short ruling that presumes that the reader is familiar with the arguments made by the parties, the facts of the case, the applicable legal standard, etc. And it'll just get right to the point, a short and sweet explanation for why one side wins and the other side loses.

That—95% of our rulings are in the MemDispo style. And so we don't take the time to write long—the clerks don't take the time to write long bench memos and we don't convert those long bench memos into long district court opinions. We just do a quick—we do explain our reasoning, we make clear why one side wins and the other side loses, but the theory is it's better to get them a short ruling quickly than it is to get them a long, winding ruling much later down the line. And so that's the system that we adopted when I first got here and it's largely stayed that way ever since. And I think it's worked really well. I think it's helped us manage the cases, manage the docket well, and move things along well while still allowing for careful consideration of the issues.

The value Judge Chhabria places on plain language — writing for the “sophisticated non-lawyer” — connects to what Rakesh Kilaru calls the “courage to cut”: simplifying arguments to what actually matters.

Now, there's probably 5% or 10% of the motions where we will decide that we need to do a full-length opinion, like a proper judicial opinion with a factual background section and a legal standard section and all of that. Maybe it's because it's a matter of significant public interest, maybe it's because we feel that the case law is muddled and there's something that we can say that might help sort of clear up the case law, or something along those lines. And so in that situation, we'll do a more full-length opinion and it'll often take longer to get out. But by minimizing the number of those that we do, we're able to move the docket along much faster. I guess the only other comment I'll make about that is that as I am on the bench longer—I've been here 11 years now—I'm sort of committed to doing more full-length opinions because I think I know the job a little better and sort of maybe have a little more to offer than I did eight years ago or six years ago or whatever, and so we're probably doing a bit more full-length opinions than we did at the outset.

Khurram Naik: And it seems some of this is associated with the style—the MemDispo style that you're describing—is plain language, which can be very sharp. Is there a connection between these two? Are they separable?

Judge Chhabria: I think they're—I mean, I think it's easier to do a MemDispo if you're using plain language, direct language. But I think they're kind of two different things because I think that we use those in our opinions too. I think we use pretty plain direct language in our opinions. And our full-length opinions are usually a lot shorter than the typical full-length opinion, by the way. And I think that that's a separate issue but it also has to do with public service, right? That it's really important. The way what I tell my law clerks is: think about somebody who maybe is a non-lawyer, like perhaps a sophisticated non-lawyer, and what do we need to tell them, what do we need to teach them in order for them to be able to understand why we're ruling the way we rule. So you might think about a legislator who is busy and smart but not a trained lawyer or not a practicing lawyer, and what do we need to explain to them in plain language so that they get what we're doing? Or like a busy reporter or something like that. And we just try to write with that sort of reader in mind and try to avoid the legal jargon and a lot of the gobbledygook that we see in judicial opinions, particularly earlier judicial opinions.

Khurram Naik: And then, so if other federal judges seem—whether it's reticence or otherwise—they just don't use that style, both of the length of opinion, plain language, and tone, which I can see as you're saying, let's say a reporter, it's very eye-catching to use some of the rhetoric that you use in some of your opinions. For instance, we'll talk about the Kadri opinion and there’s definitely some strong language in there. And so with that, how would you—let’s say with a new federal judge who's turning to you for some guidance—how would you make the case for, you're saying there's a public interest in the decisions you're making, how would you influence your peer federal judges to be influenced by the style and techniques you're describing here?

Judge Chhabria: Well, I mean, I think it's for every new judge to decide how they want to do it and it depends what you're comfortable with. But I would just say that the law, for the law to be understandable, it needs to be accessible. And I do think that one big problem the judiciary has is not being accessible enough in its writing, and it makes it harder to understand why we decide stuff the way we do.

Khurram Naik: So, in terms of impact of your time on the bench, some leading litigators and lawyers have referred to you as being a leading feeder judge of clerks to the Supreme Court. What is it in your process that has made you such a source of lawyers that go on to clerk at the Supreme Court?

Judge Chhabria: Well, I think that's pretty easy. I've been able to hire law clerk candidates who also end up clerking for great circuit judges. So, people like Michelle Friedland and Sri Srinivasan and a number of others, and those are the people who tend to go clerk at the Supreme Court. The other thing that we focus very heavily on in our hiring process here is making sure that we have nice people. And you know, it's been 11 years now and we've never had a problem person, we've never had somebody with sharp elbows or who's trying to be nicer—be more respectful to the judge than to the janitor—or being competitive with their co-clerks or anything like that. And we work really hard to weed those people out. And those people tend to not be great candidates for the Supreme Court either, frankly, perhaps contrary to popular wisdom. So, that's really all I have to say about that.

Khurram Naik: What do you miss about not being a judge?

Judge Chhabria: Boy, very little. Very little. I mean, the job is so interesting and so low stress. I mean, there is literally nothing to stress about in this job. I mean, you know, maybe one exception is criminal sentencing. You know, those are some, there are sometimes some gut-wrenching decisions there. Another exception might be law clerk hiring—that can be kind of stressful because the stakes are so high because if you do get somebody who's like a problem person in chambers, it could be really bad for the year. And that's why we work so hard to weed out those types. But it's just such a low-stress job.

And you think—I always think about how if I had a big oral argument as a lawyer and I'm driving into work that day, I'm like, you know, going over in my mind all the possible questions I could get and thinking about how I would answer them and making sure I knew in my head where the evidence was in the record to support the points that I was making and like talking to myself in the car. People looking over and staring at me and I guess probably they thought I was on the phone. But, you know, it's stressful. Being a lawyer is stressful and being a lawyer who goes and argues in front of the Ninth Circuit or whatever is, you know, it can be quite stressful.

But when I'm driving into work as a judge and I've got a big hearing, I'm thinking about the questions I can ask. I'm thinking about the things I don't have a good handle on and thinking, "Oh, cool, I'll be able to ask the lawyers these questions. And they will help me, hopefully, understand the answer to these questions that I'm struggling with." And so there's just nothing to stress about because I don't have to have all the answers. I just have to ask the right questions, right? And, you know, I've got my law clerks helping me and all that kind of stuff. So, it's just—there's very little that I miss.

I would say that every once in a while, when I'm driving into work, I might be listening to the radio and there's some something exciting happening in City Hall or some big blow-up in San Francisco politics or something like that and I think to myself, "Oh, I'd like to be in the middle of that and like helping the clients troubleshoot that, helping people solve this problem." But, you know, there's plenty of problem-solving to be done as a judge too, and so I barely ever think about the stuff that I used to do and wish that I could keep doing it. I mean, this job is just remarkable.

Khurram Naik: That's interesting because on one hand I think of like a barbell here. On one hand, you're probably a lot funnier now. You get a lot more people laughing at your jokes.

Judge Chhabria: Yeah, that's one thing I miss. Actually, that's something—that's good, I’m glad you brought that up—because the other thing I miss is getting honest critical feedback. Because I don't—it is virtually impossible for a judge to get honest critical feedback. My best source of honest critical feedback can be from my law clerks, but even then, I think sometimes law clerks are nervous to give you honest critical feedback. And, you know, that's something that I always have sought throughout my career as a lawyer and even as a judge. and I think that's how you get better, right? Is that you continue to question yourself, you continue to seek critical feedback, and I do miss not being able to get nearly as much of that in this job.

Khurram Naik: Well, how do you contextualize then the critical feedback because I think of, say, appellants—they're going to have some critical feedback about a decision. Half these outcomes, you know, half the people are going to be dissatisfied with your decision and have something substantive to say about it. And then there's the appellate court; they’ve got feedback for your decision. Aren't those forms of feedback that are relevant or is there something different about that?

Judge Chhabria chose the City Attorney’s Office over the U.S. Attorney’s Office for its constitutional policy work. Jaimie Nawaday took the AUSA path at SDNY — and it was there that the Bank of America trial transformed her career.

Judge Chhabria: I think there's something different about that. That's not so much about how you do your job and whether you're doing a good job, right? Because, you know, if you get reversed by the circuit, it might be because you missed the issue—like you made a mistake, right? But again, that's I think that part of being a good district judge is not spending all your time trying to avoid mistakes, right? Because that then comes at the expense of moving the cases along and, you know, the justice system functioning properly. So, but if you get reversed it might be because you made a mistake, or it might be because the circuit made a mistake, or it might be because reasonable—and this is most common, right—reasonable judges can differ on the outcome. And so it's not—I don't really view a reversal as criticism of how you did your job. It's just part of the system, right?

Khurram Naik: So the other part is you deal with these really consequential decisions. For the Northern District of California, it’s a very important jurisdiction nationally. There's high-stakes matters, for instance involving this administration. There’s a variety of—we’ll talk about the Kadri matter in a moment. So, there are these high-stakes matters, matters of first impression. You’re saying that you don't really feel a lot of pressure in those scenarios? Because sitting here thinking about what it would feel like to be in your shoes, I feel that I would have a lot of pressure. But it sounds like you don't experience that.

Judge Chhabria: No. I mean, it's pressure is when you have to make a decision like really quickly. And sometimes in the, you know, when you get a preliminary injunction motion or a TRO application, you have that, I guess. But no, I you know, it's I view it as like a pleasure and a privilege to be working on these kinds of issues.

Khurram Naik: Okay, so we teed up the Kadri decision, and you mentioned this concept of, you know, potentially there being disagreements and I think this decision will be an interesting lens on that. So, first, if you can give some context for the decision. We recognize it's an ongoing matter, so we’ll be careful in the scope of what we discuss here. But can you speak about the process you used to arrive at the market dilution framework you proposed for fair use?

Judge Chhabria: Yeah. Well, maybe first by way of background, just so that people know what the case is about. And I do need to be very careful and limit myself only to stuff that I have said from the bench or said in my ruling, because it is an ongoing case. But it's a lawsuit by book authors, right, who claim that it's copyright infringement for Meta to use their books to train its generative AI models without compensating them. And Meta's argument is that it's fair use, right? That using copyrighted books to train AI models falls within the fair use exception to copyright infringement.

And so a few months ago we had oral argument on summary judgment and Meta's lawyer, Kannon Shanmugam, focused heavily on the fact that the purpose of the copying is transformative, right? That the copying is being done to create something very different from the original. And often that'll be dispositive in copyright cases, right? If the copying is for a transformative purpose, it's going to be considered fair use and it's not copyright infringement. But what I said at the hearing and in my subsequent ruling is that the AI situation is potentially different, right? Yes, the use is transformative, I don't think there's any doubt about that. But the thing that copyright law cares about most is preserving the incentives for artists to create.

And if you let a company copy protected books for the purpose of creating a product that enables the production of literally millions of books in the same genre using only a minuscule fraction of the human creativity, that has serious potential to harm the market for the books that were copied. And so I said that this is one of those situations where copying the book for a transformative purpose might not get you out of copyright infringement. That's the market dilution point that you referenced, right? The issue in our case was that the plaintiffs didn't put in any evidence that they would be harmed by market dilution, and so I granted summary judgment in favor of Meta in this particular case against these particular individual plaintiffs.

You asked how I got to the issue. In this case, we were fortunate enough to have a bunch of amicus briefs filed on both sides. That's very rare in district court cases, but obviously this is a big case. And so even though the parties didn't address the issue too much in their briefs, the plaintiffs didn't address the issue too much in their briefs, it was addressed in the amicus briefs and in the sources that the amicus briefs cited. So I read those briefs and read a lot of the sources that they cited and learned about the issue that way and was able to discuss the issue as a result of that.

Khurram Naik: So Judge Alsup had a decision two days earlier. How did you think about the impact of different approaches from colleagues in the same district court on fair use?

Judge Chhabria: Well, I mean, I guess I have a specific response and then a more general response. First, the more general response. My law clerk asked me a similar question—I have new law clerks just come in, they're new now—and one of them asked me, "How should we be thinking about opinions from other judges on the Northern District?" because sometimes the lawyers in the briefs, they will say, "This district has held XYZ," and you look at that and you cock your head and you're like, "Well, what does that mean?" because a ruling by another judge in this district is no more binding or no more should arguably be no more persuasive than a ruling by any other district judge, right? It's not binding on me.

And that's the way I view it, right? That I mean, obviously, I have great colleagues and take very seriously what they have to say. But the fact that multiple colleagues have ruled one way on an issue is not going to be a thumb on the scale for me ruling the same way on that issue. As a matter of fact, I was telling this law clerk the other day that we had one case a few years ago where 11 judges on the Northern District of California dismissed this particular type of claim, and then I got one of these and I disagreed with all 11 of the judges and I denied the motion to dismiss. That was an example of writing a full-length opinion and explaining why, right? But you're obviously going to pay close attention to what the colleagues say, but it doesn't create a thumb on the scales one way or another for how we decide a case in these chambers.

And then you mentioned that Judge Alsup issued a ruling in his AI case a couple days before ours, and Judge Alsup had a very different perspective on the issue than I did. He placed tremendous amount of weight on the transformative nature of the use and that seemed kind of dispositive for him. And so yeah, we got that ruling a couple days before we issued ours, read his ruling, and included a bit of a response to it in our ruling.

Khurram Naik: So, I’m mindful of our time here and since we’ve got a final question. I’ll pose the question is: you’ve had a number of law clerks over the years, and the relationship is a really special one and they really are able to see how you think up close. And so my question for you is, what is your key advice that you give your law clerks? What’s the most important advice you give them on career?

Judge Chhabria: Yeah, I mean, I think it probably goes back to my experience applying for the U.S. Attorney's Office and the City Attorney's Office. I think that you should not be taking a job based on where you think it will get you. You should be taking a job based on how fulfilling and happy it will make you. I know that sometimes there are financial constraints, and I always try to be mindful of that. I know you can’t—not everybody can just go work for the ACLU, right?

But within those financial constraints, definitely don't think about the prestige level of the job, don't think about where it might get you five or ten or twenty years down the road. Just do what is going to be most fulfilling for you and what's going to make you happiest. And that is going to increase the chances of you having success down the road because if you're doing a job that's more fulfilling and makes you happier, you're going to do a better job at it. People are going to like you more because you're going to be happier, they're going to be more likely to want to help you, and all in all, your career is probably going to go better. Plus, you can never really predict which job is going to get you to which place because things are always changing, as my experience shows. And so I think that's the primary advice that I try to give folks.

Khurram Naik: Thanks Judge Chhabria. This is definitely the funniest episode I've recorded yet.

Judge Chhabria: Really? Oh, wow. You need to get some better guests. But anyway, thank you very much. I appreciated you having me and it was a lot of fun.

Khurram Naik: Thanks.

I reached out to Rakesh to learn more about his practice, and the conversation flowed. For someone of his accomplishments, Rakesh is remarkably humble. He's driven by excellence and impact. We could easily have recorded a much longer episode.

Keep reading below for the full link to the episode and the full transcript of our conversation.

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Top Insights

Below are the highlights of our conversation:

• The "Expert Draw" and the Credibility of Non-Experts: Rakesh notes that in high-stakes litigation, paid experts often "cancel each other out" in the eyes of the jury. True persuasion often comes from non-expert witnesses—like business executives or prescribing doctors—whose real-world decisions and contemporaneous internal communications (like emails) provide a more intuitive and trustworthy narrative for the jury.
• The Hidden Benefit of "Virtual Firms": Rakesh highlights a unique advantage of the litigation boutique model: the frequent collaboration with other top-tier firms on massive matters. This "virtual firm" structure allows lawyers to learn through osmosis from different institutional styles and diverse legal strategies, an opportunity that is often less available at large firms that try to keep all work in-house.
• The "Pretentious" Necessity of Creating Space: Transitioning to a lead role requires the "courage to cut" and the discipline to step back. Rakesh argues that being the most responsive person on an email chain can be toxic to a team; true leadership involves intentionally creating space for junior lawyers to develop their own judgment and build direct relationships with the client, even if it means allowing them to be wrong occasionally during the learning process.

Full Transcript

Khurram Naik: Rakesh, I’m really excited to record with you. I’ve really enjoyed getting to know you. It’s been kind of a whirlwind of a couple of conversations, but I feel like we could talk for a really long time. I know you’re very busy, so we’ll squeeze in what we can here. One of the things we talked about is your work on a number of landmark matters in recent years. One of the ones that is most remarkable is your work for the NCAA as lead counsel on a proposed class action. This litigation has been going on for something like 40 years, and you worked on a novel settlement for that. We can definitely talk more about the mechanics of that, but I think what was interesting is how the experiences you had at the White House as Counsel there built the skill set that you use in this and other matters. I thought that could be an interesting starting point—to talk about how you came to the White House and the skills you picked up there. You mentioned when you came to the White House, you spent way too much time thinking about the job. Can you talk about that?

Rakesh Kilaru: For sure. And thanks very much for having me on. As you said, I love talking to you and we could talk for a long time, so I’m excited to get to do it. I think when I first got the opportunity to go to the White House, as you said, I spent way too much time thinking about it. What I mean by that is I had built up in my head this idea of exactly what I thought my practice was going to be like. For a long time, it had been focused on appellate law and kind of pursuing the things you typically pursue in appellate law: clerking, working at a firm for a little while, and then maybe going into the government and really focusing on appeals.

I always thought I would go into the government, and it turned out that the first real opportunity that presented itself was this White House opportunity, which was a totally different thing. Instead of doing all litigation in appeals courts, I would be doing almost no litigation in any court. I spent a lot of time thinking about whether that was a huge diversion, whether that would set me off on some different path. Ultimately, frankly thanks to a lot of help from my wife who sorts through things really well when I’m agonizing over them a little bit too much, it really came down to a couple of questions. The first is: are you happy on your current trajectory? As I spent time thinking about it, I realized I wasn’t, in part because you spend a lot of time in appellate law sitting at your computer, writing and thinking. It’s not that I don’t enjoy doing that, but it felt for me a little isolating, a little cloistered, and not as dynamic as maybe an environment in which you could pull different levers, change how the factual record is developed, or think of a business solution outside of a courtroom.

The second piece she encouraged me to think of is just: do you think it would be fun? When I actually thought about it that way, instead of in this very instrumental "what’s the next step and the step after that" way, it became a lot easier because it did seem like it would be a lot of fun to go into the White House to work for President Obama and to tackle some pretty challenging issues in areas I feel pretty strongly about, including labor, education, and healthcare. So yeah, I spent too much time thinking about it, but then I ultimately made the decision to do it, and it really has changed my life and I’m really happy I did.

Khurram Naik: Do you find that you—so that was an early experience in decision-making where there’s a lot of ambiguity? Do you find that you’ve refined decision-making for either key career aspects or otherwise? What is it that you’ve honed in on? Is it a matter of just outsourcing, like for myself when it comes to things like travel arrangements, I always spin my wheels—I can look at three hotels again and again and then I’ve learned to say to my wife, "Okay, can you please step in and just cut through this?" and then she does. Is that still a tool that you use or has something changed in how you decide challenging and ambiguous issues like this?

Rakesh Kilaru: It was a good entry point because the thing that I think I learned the most from my experience in the White House is actually how to make decisions better. When I had spent most of my career as an appellate lawyer and in law school, you’re really encouraged to spend kind of as much time as you need to thinking about every side of a problem. really thinking through every possible angle of an issue, every possible outcome before you commit to a particular decision. That’s particularly true in briefing; obviously, in an argument you have to be a little more spontaneous.

In the real world, you rarely get to make decisions that way. It’s rarely the case that when someone asks you to make a decision, you say, "Okay, well let me sit down with the other side’s argument for four weeks and think really hard about it and then I’ll get back to you in six weeks with my own perfectly formed set of ideas and written-out arguments." That happens in appellate law, and it’s a great thing that it does, but it’s just not how most decisions work in the real world. What the White House taught me is really how to make decisions in volume and with imperfect information, and then to really constantly evaluate your process after you make the decision to try to make sure you got it right, or at least that you were thinking about it in the right way.

On any given day in that job, there were probably 15 to 20 different scenarios that came up. On every one of those 15 issues, there would either be some media-imposed deadline because someone was going to report on something, or there was a policy deadline we had to meet set in legislation, or there was just a desire in the building to get something done on a particular issue and resolve something that had been unresolved. Constantly, people would say, "Hey, I need an answer on this by 5:00 PM. Here’s the background. I need the best advice you can give me." When you do that again and again and again, for the first few months, you’re probably going to get a lot of stuff wrong, and I really leaned on my colleagues to help me figure out how to do them in the right way. But only by doing it again and again and again do you get better at it. That’s where the White House has been super valuable to me in all aspects of my life—it really taught me how to make decisions quicker and better, to live with a little bit of uncertainty, but then to take that time afterwards and think, "Is there something I wish I had had that I didn’t have? Is there an input I wanted that I didn't have that I could try to get next time?" Doing that again and again in this kind of refined process—I wouldn’t say it makes me make perfect decisions, I make mistakes all the time—but I feel more confident in making decisions than I used to.

Khurram Naik: Two questions I have. One is: that skill set you said as an appellate lawyer of doing a deep dive and really thinking through all the angles, does that show up in your practice at all anymore?

Rakesh Kilaru: For sure. I mean, first of all, we still do some appeals, and I’ve actually been fortunate enough to argue a couple of appeals this last year that I was pretty excited about. When you’re doing that type of work, it still is hugely beneficial to be able to take that time and exercise those muscles of really thinking through in a long and deep way what the issues are. On the other hand, I also think that I’m better at that than I used to be because there’s, for me at least, a little bit less wheel-spinning in terms of how I think about things. You think about an argument, you think about your counter-response, and then you think about what the other side’s going to say about that. At least for me, I feel like I can process through that a little quicker and a little better than before, when you can kind of just sit at a blank page and sort of not know where it’s going to go for quite some time.

Khurram Naik: Yeah, I’m curious about how those two types of thinking relate. Do you feel like the two of them have kind of merged a little more where you’re capable of taking the best of this and the best of this and kind of combining the two, or are they two different modes of thought that you have? Like, "Hey, right now I’m in lightning decision mode" or "Hey, you know, I’m in deep dive mode."

Rakesh Kilaru: I’d like to think they’ve merged. I’m not sure it’s true that they have sort of merged into something that’s better than the sum of the parts, but I think they’ve merged in the sense that I feel much more confident as a writer because I have spent more time in trial courts and in atmospheres where you have to make a quick decision. A lot of traditional appellate writing teaches you to take your time to make the point you want to make and to build up to an argument. That’s a lot of how we think sometimes—we talk ourselves into the solution by starting somewhere and discussing it and then you get to the answer. Really good appellate writers and really good appellate advocates are very good at cutting through that. For me, the process of litigating in trial courts where judges just want an answer, and they want the best answer, and they want you to be efficient, and they don't want to waste a lot of time because they have a million other cases, it’s forced me to get to the point a lot quicker. That aspect of oral advocacy has, in my view, immensely improved my writing because now when I come to a brief, I try to think: what does the judge actually need? What do they want, what do they need to get to the right decision, and how can I get to that more quickly than I did before?

And then on the flip side, when you’re arguing, when you’re doing stuff that’s more spur of the moment, I think having spent so much time typically in advance thinking through these issues in detail in a structured way like I used to a little more from an appellate perspective, it actually helps because I feel like I have more to draw on when you have to make that snap decision. I still try on the front end to go through that more studious process of really thinking through everything.

Khurram Naik: So let’s go back to when you’re in the White House and early on you discover, "Wow, like I need to make decisions really quickly here." You probably came up with some system for making decisions quickly and then, as you say, you got lots of reps in in a short period of time and really refined that. Tell me about the earliest structure you had around decision-making and then how it changed by the time you exited the White House.

Rakesh Kilaru: Really good advice I got on my first day was that the way to make good decisions in that space is to focus on people and process. "People" is pretty simple. I had a lot of clients in the White House—a lot of folks who worked on different aspects of policy. So there were people in the Domestic Policy Council who worked on labor issues, and then there were people in the Labor Department who worked on labor issues, and then there were people at other agencies who would have issues that occasionally touched labor. Developing meaningful relationships with that group of clients—sitting down with them, chatting with them, not really having an agenda, just trying to understand what was on their mind—was really helpful. First, to just educate myself, because there were a million things that were going on in the White House that I just did not really know about before I started the job that I was all of a sudden responsible for helping make decisions on.

Getting to know the people really well and building good relationships with them was really critical because they, I think, could look at me as someone who was kind of an honest broker, didn’t come into it with any particular agenda, and understood what their concerns were. When both people who you’re trying to mediate between think that, I think it can be really helpful. And then "process." A large part of it was figuring out: is everyone who needs to weigh in on this decision part of the decision? Coming from a law firm, I had a little bit of this attitude of, well, the email that I receive has the right people on it. In the White House, there was this thing where you would get these email threads and there would just be the text of the email would just be the plus symbol, but like four people would have been added to the CC line or the To line. The first time I got one of those I was like, "What is this? Why are there all these plus symbols in an email?" But the point was: this issue, whatever it is, whether it's a labor issue, a tribal issue, or a healthcare issue, it’s going to touch a lot of other people's equities, so to speak. Treasury might have to make payments as a result of something being done under the health care bill. Making sure those people are at the table in the first place is really important to making sure you have all the perspectives that feed into the ultimate decision.

So a lot of what I did for the first few months was actually not make decisions myself—and my bosses were great about this—I was able to work with them to figure out what those decisions needed to be. But their attitude was very much: spend a couple of weeks, spend a month, just meeting the people, understanding the general processes people follow, and then once you feel like you have that understanding, it’ll be a lot easier for you to confront situations when they come up. And that proved to be true. I think by the time I left, I would get an email or someone would stop me in the hall about an issue, and I could pretty quickly figure out: okay, who else needs to weigh in on this? And what’s the right way to bring those people together? Is it a meeting? Is it an email where I make a proposal and people react to it? Is it for someone else to send out that email? There’s a lot of different tools you can use to try to resolve an issue, and just having seen a lot of it, there’s no substitute for that. That’s true in my work now. There’s no substitute for seeing what something looks like before you do it yourself, and then actually doing it yourself. People can talk about this stuff all they want, but at the end of the day, you have to get in the courtroom, you have to get in the arena and do it.

Khurram Naik: So fast-forwarding from this skill set you picked up on decision-making and people and process. How do you apply people and process today? Can you just talk us through a couple of examples?

Rakesh’s choice of a boutique over BigLaw after the White House mirrors what Randy Gaw experienced — he left BigLaw specifically because the partnership track wouldn’t give him first-chair trial work, and built Gaw Poe around that missing piece.

Rakesh Kilaru: I don’t think it’s that different. In some senses, we have the benefit of in my practice being able to get a lot deeper into an individual issue because we’re a smaller firm. We’ll typically have somewhere between 10 and 20 active matters at any given time and we have about 40 to 50 attorneys. So each of us at any given time will probably have somewhere between two and five cases or issues that are really taking up a lot of our time. Because of that, you can spend more time on each of those just getting more familiar with them. And so from a process perspective, and frankly from a people perspective, everyone working on one of our teams gets super invested and super deep into the matter early on. That can be really helpful because you don’t have to have meetings where you’re trying to explain the really basic issues to people who are new to it; you have a group of people who are really invested and really understand the issues pretty well.

But beyond that, when it comes to making decisions, when it comes to writing a brief, when it comes to figuring out how to argue something, it ends up being somewhat similar. From my perspective, I want to get a lot of really smart, thoughtful people to give me as much advice as I can get before I have to actually do it. And after I do it, I really want those people to help me critique myself and think: did you do that well, did you do that poorly, what went well, what went wrong? That involves getting all the people on my team—which is to say the people who are literally on the case team—to weigh in, and to encourage folks who typically don’t speak up sometimes to say, "Hey, I know you haven’t really said anything yet, but I really want to get every perspective I can on this. So what did you think? When I said that, what sounded good, what sounded bad, what worked for you, what didn’t?"

Another piece of it—and this is a real luxury of our firm—we don’t bill hours. So it’s pretty easy to get people who aren’t on our team to listen in to things and give us a real fresh perspective. You work on a case for so long, you can very easily lose the forest for the trees and get super into the weeds. I’m lucky that pretty much any one of my colleagues you can pull in and say, "Hey, I know you know nothing about this, but let us pitch to you how we’re thinking about arguing it, and let’s get your reactions as someone who isn't coming to this super deep-invested in it, because that’s probably going to be the case for your jury or judge."

And then I think the same thing is true with clients. You want to get their buy-in early and often. Every client is different in terms of how much they want to be involved in a particular decision or how you make a particular argument or even the particular words you use in a brief. But trying to figure out early on how your client in a particular matter operates, what their process is, how they think about it as people, is really helpful to making sure that you’re giving them the time they need on the back end.

Khurram Naik: You’ve talked a couple of times about what you’ve learned after the fact. What’s the hardest lesson that you’ve learned in a post-mortem? How did it change your process?

Rakesh Kilaru: That’s a great question. I would say more often than not, the hardest lesson I’ve learned is that the things you thought were important just really are not. [Laughs] This comes up often. You work on a case for a while and so much of legal training encourages you to run through the tape on every issue. If you think back to taking a law school exam, one of the things that’s rewarded is seeing every possible aspect of the problem and saying, "If this issue were presented, here would be the answer. If this issue were presented, here would be the answer."

More often than not—I’d say pretty much all the time—when it comes to a jury trial or an argument in front of a judge or pretty much anything in front of a judge, they really want to get to the bottom line and they want to figure out what actually matters. It doesn't work to say, "Hey, I have five different arguments. Let me show you all five of them." You really have to have the discipline to figure out: what’s the one, maybe two, maybe three things that are the core of your case? What are they? Are you diagnosing them correctly? And then are you driving those themes and not preserving every little issue along the way or checking every little asterisk or apostrophe or whatever in the argument that you might want to make?

Often, to be more concrete, I’ll do a jury exercise or maybe I’ll even argue something to a jury, and there will have been beforehand one or two points that I thought: this is the key to the case. And sometimes you’re just wrong on those—that’s why you do it. It turns out you thought that these were the two things and jurors just didn’t agree those were the two things. You evaluate that and think, "Did I get those two things right?"

But more often than not, I find when I’ve learned a harsh lesson, it’s that I thought I had two things and then I argued and I made five or six different points and the two things got lost because they were like these little other things that in the moment I was like, "Oh, I want to chase this thread or I want to chase this thread." So having the discipline to boil it down and the courage to cut stuff that isn’t ultimately going to move the needle, it’s the hardest skill I think for any lawyer to develop. It’s to me what makes trial work so fun and exciting and so different from everything else. So much of skill comes from correctly identifying the important issues and then being ruthless in not getting bogged down in rabbit holes. Those are two things that law school and most traditional education—and frankly, even my background as an appellate lawyer—kind of pushes you away from. It pushes you more toward "be cautious, present everything, don’t be in a position where they can’t say you haven’t argued this." More often than not, when I’ve learned a hard lesson, it was when I came out of something and the person was like, "Listen, I know you thought you had two points, but five came across, and so none of them came across as a result of that." You know, the way you thought you were subtly working in points four and five actually distracted from your key narrative. That’s a constant skill to get better at.

Khurram Naik: It’s interesting to hear you say that because I feel like a layperson’s sense of what’s persuasive—and I think everyone’s run into someone like this—is when someone’s trying to take a position of some kind, they just kitchen sink it, they just throw everything at you. And then in law school, you learn this counter-intuitive version of it, which is arguing the alternative—one of the core concepts you learn in law school that's not intuitive at all: "I wasn't in the room and even if I was, I didn't drop the vase." That's not how we have any—that's nothing I would ever say to another human at a party, right? But I feel like what you’re saying is the level beyond that is it's kind of this U-turn back to something that's even more fundamental, which is one argument. That necessarily means trade-offs; it necessarily means it's taking a risk and calling a shot. It's funny because we have this conception of lawyers as being risk-averse and I think that is broadly very true. But in this way, I think this is an opportunity to take on a risk. It's a risk to say, "This is it, this is the strongest position." So can you talk a little about what it feels like to be calling a shot that way and when you’re in trial it’s done in such a public way and there’s a record of it? What is it like to just call your shot?

Rakesh Kilaru: It’s fun but it’s frightening. Those are the two sides of it and that’s sort of why I love it. What you said is so spot on. In law school, you really are taught to make these alternative arguments and say exactly as you said, "If A, if not A then B, if not B then C, if not C then D." And when you talk to real people in that way, they’re just like, "So which is it? And why are you giving me all four?" And the fact that you’re giving me all four makes me really think you don’t believe in any of them. So there’s an art to figuring out, okay, well I had that chain, and it was really—and it is still—really important to work out that chain. What are all the potential arguments, what are all the different paths to victory? We might even map that out on a board and say, you know, in an antitrust case, here are all the different elements, here are all the different arguments we could make. But then you have to build that out to be making good decisions, but then you have to winnow it down.

The “courage to cut” — simplifying arguments down to what actually matters — connects to something Joe Ahmad told me about juries: they respond to authenticity and directness, not polish.

Early in my career, even a few years ago, I just wasn’t very good at it. I had the good fortune to spend a lot of time trying cases with my partners Beth and Brian who have many, many skills, but I would say one of their most profound skills that I learn from every day is this skill: it’s figuring out what to cut and having the courage to cut it. And say, "Listen, I know you think that’s a good issue, and it may be a good issue in front of a judge that product X is in the market and product Y is out of the market in an antitrust case, but that just feels like that’s going to seem really technical and like a technicality and it’s not common sense or intuitive to a juror." So either improve your process for explaining it or cut it. You probably have a couple other arguments that are better, so why don’t you focus on those? I think I’ve gotten better at it by watching them and I’ve gotten more comfortable in making those decisions—not just by watching them but by thinking, whenever those moments come up in a case, how would I do it if I were them? And then I see the decision they make and, you know, sometimes it’s the same one I would have made, sometimes it isn't. And trying to learn from that. It’s like, okay, well they approach that issue differently on this cross-examination, for example; I thought these five points were the ones that were really important, they thought these two were the ones, and they were right. So how do they pick them? You sit down, you talk with them: why did you think those were the two as opposed to the five? Just doing it more and more I think helps a lot.

But I guess to answer your first question—how do you do it?—the way to do it is to do it. It’s one of those things where the longer you put it off and the more you avoid it, the worse it gets. At some point, you just have to commit and say, "In this exercise, I’m going to try one and two and I’m going to be completely committed to it. At this trial, I’m going to try one and two and I’m going to be completely committed to it." And maybe I’ll be wrong, but I’d rather be wrong pushing a consistent narrative that people can understand and they just may not like it, than trying to give them a bunch of different arguments that makes it seem like we don’t know what we’re really talking about or we don’t know what we actually care about.

Khurram Naik: Yeah, it makes a lot of sense. I think in the context of being a legal recruiter, a lot of times lawyers, understandably, the reason why they're looking to make a change is because they want to change the kind of work they're doing. In doing so, people are curious—so people are curious about different practice areas and interested in different practice areas—so any number of times people say, "Hey, I want to explore a couple of things at once." And so yeah, my counsel is let’s focus on one for a dual purpose because there’s two audiences here. One is the partners of this firm so they understand: hey, what is it that you’re trying to do here? So that narrative doesn't vary. And then also for the client, so that they have a single narrative that they’re not trying to balance multiple narratives and "Well, what did I say in this one, what did I say in this one?" It just gives clarity for everyone. But it’s not easy, it’s not preferable. People want options, they want to preserve options, but the trade-off of all those options is noise, and so the benefit of taking the risk of a single narrative is clarity.

Rakesh Kilaru: I totally agree with that. And I will say I started out thinking about this as a jury trial skill, and it is very much a jury trial skill—it’s really important to, even if you have a trial that’s going to last a couple weeks, a couple of months. There’s a lot of information that people are being asked to process. They’re in this environment that most of them probably don't want to be in, where they’re away from their jobs or their families and they’re in this courtroom listening to people talk at them for a bunch of hours a day. So in that format, it’s really important. But I’ve started to find that it’s hugely important everywhere else too.

When writing a brief to a judge, yes, we ultimately may make three arguments, but do we know which is the best one? And are we leading with that and are we developing that and spending as much time as we can on that and sort of signaling that that’s the one they should focus on and how much we talk about it and how we talk about it? Even when it comes to like a meeting with a client or a meeting with opposing counsel to think through a mediation strategy. There’s three issues, there’s four issues we could talk about—what are the ones that really, really matter? And what are the ones that you can give on, what are the ones that are less important? Being able to prioritize and figure out where the best argument is, where the stuff you can cut is, or in the settlement context it’s a little different, like where the issues you can give on and where you can’t give on. I think they’re all variants of that same skill of figuring out what really matters and having the courage to prioritize it and sometimes tell people even on your side, like, "Hey, listen, I know you think that these five issues are all equally important. Like, that’s just not—that’s not going to happen. Like, we’re not going to get the judge to rule for us on all five, the other side’s not going to agree with us on all five. So let’s pick the two that we really want to drill down on, make those home base, like really defend that territory, and then the others—if we make them, we make them because sometimes totally early in cases you want to preserve arguments for later on—but let’s try to signal a little bit and make the judge’s life easier." At the end of the day, they have to make decisions too—judges have to make decisions, juries have to make decisions, clients have to make decisions—and the more you can do to make those lives easier, the better you are no matter the context.

Khurram Naik: Going back to what you were saying what you did at the White House, a key part was just listening to stakeholders. You’re spending time with these different people, getting to understand how they see an issue, and then you’re in a position to synthesize. There’s a lot of importance to listening. And then something you also referenced was in this flat fee model you have, it permits you to have a large team—whatever size team you want—on an issue listening and really going deeper into understanding a client perspective. On one hand, your process involves a lot of listening, but then on the other hand, your process is about honing in on one issue. So you talk about the importance of flexibility with clients or with anyone—because I think probably there's flexibility that's involved with judges—one judge may really be interested in hearing one type of perspective or issue or lens on a matter versus another judge. How do you balance adapting to client, opposing counsel, judge, with your focus on process and making sure that you’re executing your process with excellence and refining that? How do you balance those two?

Rakesh Kilaru: I think they go hand in hand at the end of the day. One of the, I would say if I were to self-diagnose one of my bigger weaknesses, it's actually for a long time it was being way too analytical about things and spending way too much time thinking about them, as we talked about at the very beginning. I would say over the last few years, it’s become a lot more sometimes doing things a little bit too quickly and thinking, "I've seen this scenario before because I've seen a lot of things whether in the government or in litigation and so I know exactly how to approach it." Of late, I think my whole life and I think this is true of everyone—you’re going to ultimately be between two poles on this stuff and sometimes you’re going to err too far in one side and sometimes you’re going to err on the other.

But the listening helps because to me, being in a meeting and not being the person who talks as much and listening to others talk has become an increasingly important skill. I know that sounds terrible because early in my life I really liked to talk and sort of true to some point we all do. But I think listening to what other people say and how they talk about it has become more and more valuable to me and it’s sort of a reminder of what life was like when I started in the White House. Because a lot of folks are going to approach these cases differently. In a team meeting—even we had a team meeting yesterday and we were reacting to some briefs the other side filed—and six or seven people spoke up and they all had slightly different takes on what they thought was the most important thing. But at the end of it, if you reflected on it, there were a couple common threads that the group thought were really resonant and some of those jibed with what I had thought were the key points and some didn’t. But there was something to that, right? When you hear a lot of people talk, what are the common threads you’re hearing? What are the common concerns you’re hearing? What are the things that stand out as "we think this is a real strength for us, we think this is a real weakness for us"? Gathering more information on that not just from my teammates but also from our clients is super helpful.

And knowing what guardrails are is the other big benefit that comes from listening. This is particularly true with clients. It may be that there’s some stuff where they say, "Listen, this is just an argument we can’t make. Like I know you want to make it, but we cannot make it for this business reason. Like we can’t say we would never do X, or we can’t say we will do Y. Like, we’re just not going to do those things." Hearing what they say can really set guardrails. Listening to others can help you kind of sift out and hear what’s rising to the surface from your team in terms of what do they think the key points are. And then at the end of the day, I think the art and what I love about my job is trying to synthesize that with my own gut instincts and common sense into what the right decision is, making it, and then kind of living with the consequences and evaluating if you got it right. Because the fun thing about this job—which both Beth and Brian have said to me at varying points—is there's going to be another set of decisions tomorrow. And so if you get them wrong today, guess what? You got another one coming tomorrow. So you better be ready for it and you better be ready to kind of rise to the occasion the next day and the day after that and the day after that.

Khurram Naik: Let’s go back to how you came to join the firm, because you were in the White House, you had really that experience there. I’m sure you had a number of options. What made you ultimately decide on this boutique that was at the time quite young? Successful but young. What led you to say "This is the right fit"?

Rakesh Kilaru: It was a lot of things that came together that fortunately have all turned out to be true, so I feel very lucky in that regard. When I looked at what I loved about my time in the government, it was being able to help people solve problems creatively as opposed to approaching everything through one particular narrow lens, which I think was largely the case when I was an appellate lawyer. I loved working in big teams. I loved being able to talk to people with the focus being the results as opposed to time. I mean that was one of the biggest huge shift, paradigm shifts, from when I was in private practice the first time to going into the government: no one was looking at their watch. They were looking at their watch because they might have another meeting, but they weren't looking at their watch because they were trying to figure out either how much money I was spending of theirs or how much, you know, money they were losing of theirs by talking to me.

The last piece was just this kind of feeling of camaraderie that came from being in a unit. The White House is a very big place, but you end up having this group of people that you work with pretty consistently and I always felt a real sense of team with all of them, whether it was my fellow lawyers in the Counsel’s office or the policy clients I worked with. So I was kind of looking for something that felt like that. And it seemed to me like that was going to be impossible because most big firms, a lot of what I said is not really possible in the main. You’re billing for your time, so you have to be thoughtful about how much time you’re spending on a task. Your colleagues are billing for their time, so you have to be cognizant of how often you walk into their office and just try to say, "Hey, I need to spitball something with you for a couple hours."

Rakesh’s experience pivoting between government and private practice resonates with Manisha Sheth, who moved twice between elite private practice and high-stakes government enforcement, including leading the New York Attorney General’s Economic Justice Division.

The time-billing aspect of things to me can distort decisions and process. You may spend more time on something that you don’t need to spend time on or you may spend less time on something than you want just based on the pressures that come from that. And so I was thinking: look, if I could get a place that minimized some of these issues, it would be pretty amazing because that’s an environment I love being in. And I also love working on kind of big complex issues. It was one of the things that was most fun about the White House: every day there was some issue that was really important, and sometimes it was super technical and sometimes it was super headline-y, but either way it felt like it really mattered.

Kind of through fortuitousness or whatever the word is, my wife had worked with Beth at Paul Weiss before my wife went on to be a prosecutor, so I knew Beth from that. And one of the other founding partners was someone I’d worked with a long time before, and I’d read some articles about their firm and I’d sort of just thought, "Oh, trial boutique, you know, not for me." But that was when it opened two years ago, I just was very focused on being in the White House and doing that. And I started to think: well maybe this would be kind of perfect. It’s a boutique, it's small, there’s a real sense of team. They handle really big challenging cases, and I love handling big challenging stuff. Their model has eliminated the billable hour entirely. We don’t bill hours for anything. We charge clients basically for a month of our services at different rates, and so we can at any given time devote as much or as little resources to solving a problem as we need to with the ultimate goal being getting the right result for the client.

And the one thing I was a little hung up on was: well, will I actually like trial work or not? And this time I didn't spend as much time thinking about that, because I thought: there’s a lot of—I’ve never done it before, maybe it would be really fun, you know? Trial work is this thing that seems to combine a lot of skills that I find enjoyable—whether I’ll be good at it or not is another question. But I also looked at the docket and thought: but there’s also a lot of other stuff they have going on, and if I go there for a couple years and I turn out to not love trial work, I’ll probably still have worked on some really interesting stuff and then I can figure out what the right next step is. So I joined the firm, and man, like sort of like with the White House, it has been such a home run in that it turns out I really do love trying cases.

But we also have this really robust docket of cases before trial, because clients are hiring us earlier and earlier. So I feel like on the one hand, I’ve been able to develop some skills at trying cases, which is a really hard thing to do because cases don’t go to trial very often and you don’t get to work with the best trial lawyers very often, and here I get to do both of those things. But we also have cases where there’ll be really complex legal briefing, or you’ll have to think about other resolutions of the case like in our NCAA settlement, or there’ll be appeals that come out of our cases that we get to work on. And so it’s just been a lot richer of an experience and environment than I could have hoped for in the sense that we still do and very much focus on trials and I happen to love them, but there’s so much other stuff we do that’s also really interesting. So I feel like I get the best of all worlds: I get to be part of helping clients make some business decisions sometimes, I get to still do appellate work, I get to still do really complex legal work, and then there’s all this aspect of trial strategy and how to position a case that are really, really fun, and putting all that together is pretty special.

Khurram Naik: In coming over, it sounds like the work you focused on has shifted over time. Early on there was a lot of focus on products liability litigation. Can you chart out what was the trajectory of types of work that you’ve taken on at the firm? How has the firm evolved in that way of the kinds of work that you take on?

Rakesh Kilaru: One thing I’m super proud of, I think we’re all proud of, is that we have stayed true to our mission of not ever becoming a subject matter firm and really remaining a trial firm. And the distinction between that is maybe a little subtle, but I think it’s important. I think if you’re thought of as a subject matter area firm—products liability is a great example. We had a bunch of products trials when the firm started. I think we had something like five or six cases in the same product bellwether pool over that a year and a half period, maybe. And those were pretty much all the trials we were doing. We had a couple other ones, but you know there’s only so many trials you can do when you’re a firm of 20 to 30 people and so we had product trial after product trial after product trial.

And one thing that could have happened is that clients and others start to think of us as a products liability firm and so we would only ever get pitched for those cases or we’d only ever get outreach on those cases and we wouldn’t get to do other interesting stuff. And we never wanted that to happen because another feature that I didn’t mention earlier but that I should have mentioned is what I loved about the firm is it was one of the few places where they welcomed being a generalist. At almost any big firm I talked to, it was like: which subject matter area are you going to become? Are you going to become an antitrust person, are you going to become a congressional person, are you going to become a white-collar person, are you going to become an appellate person? There was and understandably so, there was a desire to put yourself in some particular vertical. And we thought we’re going to be generalists.

And the success of the firm, one of the big successes, has been that we still get calls on all kinds of different cases. So yes, we did a bunch of products trials in our first few years and they were awesome trials and I think we got a lot of good experiences, we got good results, our clients were really happy. But then there was a period of time where there just weren’t as many products trials—you know, there were a couple big verdicts and COVID happened and all sorts of different—there were many different reasons why I think there are fewer products cases now than there were recently—but there aren’t as many, and we started to get calls on antitrust cases. And that was a totally different area—you know, it’s not something we had tried a case in before, at least many of us, some of us had, but most of us had not tried big antitrust cases before. And so to get calls on those cases was exciting and was kind of a proof of concept because it showed clients are thinking of you as a trial firm, not a subject matter firm. And so now we have a lot of antitrust cases. You know, I think most of the last two years, three years, our big trials have predominantly been antitrust trials. But what we love and we hope continues to happen is that you then get a call for something else, whether it's a business dispute, whether it's another products case, whether it's some completely different kinds of case like trade secrets or IP. There are areas we haven't been able to work in yet that we hope to, but the goal is to always stay at that level of being a generalist and being able to take on any trial because I think it's good for our brand and it's just a lot more interesting.

Khurram Naik: Can you make a comparison between the nature of products liability litigation and antitrust litigation? Tell me about the commonalities and differences, and how you built on the training you had in products liability to form a foundation for antitrust litigation.

Rakesh Kilaru: Yeah, I would say, you know, on products, there are people at my firm—Beth, Brian, Carrie, Moira, and others—a lot of my partners who have done a lot of products trials. They have such an amazing wealth of experience in how to try those cases that when I started at the firm, I felt like I was really just trying to learn from them more than anything else. Occasionally I would say, "Hey, what about this idea? What about that idea?" but they had seen a lot.

They had the flexibility to approach every case differently and to think about what the unique themes are of that case, but they knew the law cold. They knew the types of arguments you can make to a jury and how they fit with the law. I think they were very good at figuring out the kind of core themes of those cases, so I felt like I was really playing a lot of catch-up on that.

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Antitrust has been a newer thing for us, just to be perfectly candid. We've done a lot of work lately in that area, and I think we have become experts in it in a lot of ways. But when we started working on those cases, it was relatively few of us—probably just Beth—who had tried complex antitrust cases before. And so figuring out: how do you marry the law to the facts? You can develop a really good narrative, but how do you match that narrative to the questions the jury has to actually answer on the form? That's something we're still working on.

In products cases, we have a really good sense of how an argument you're going to make to a jury matches with a question that they need to decide, so you can tie those two things together. We’re telling you something that's immediately useful for you when you fill out that verdict form. I think it's a little more challenging in antitrust cases because the jury instructions can be really, really long. Typically, a set of jury instructions in a product case might be 20 to 25 pages; in an antitrust class action, it’s pretty common for them to be 70 pages plus. It's a lot of information for people to distill. The verdict forms can be more complex; a typical products verdict form might have three or four questions, but it's not uncommon for antitrust verdict forms to have 12 or 13 questions. So it's really fun, but it's a challenge. The common theme in both cases is figuring out a common-sense narrative that a jury can understand as to why what your client did is right. At a very high level, both are about whether something that someone did is reasonable or not. But the process jurors have to go through in antitrust cases is just a little longer and a little more complex.

Khurram Naik: And so the challenge in antitrust cases is sustaining the jury's focus because there are so many aspects they have to touch on?

Rakesh Kilaru: Yeah, it can be that. Jurors work really, really hard and they take their responsibilities very seriously. But if you read someone 80 pages of instructions on how to do something—just think about it like Legos. When my kid has Legos that have a 300-page instruction book, you start and you're like, "Whoa, this is going to be a really daunting task." Whereas when the instruction book has 20 pages, you think, "Okay, maybe this is a little more easy to digest."

It's our job as lawyers to help them figure out in those 80 pages: what are the anchors for making a decision? Because yes, there's 80 pages of instructions, but in every case, there's probably going to be one or two issues that the case hinges on. Usually, there's agreement on that. Both sides will say, "This is a case where defining the market is what matters," or "This is a case where figuring out if anyone was actually harmed economically is what matters." There will be these areas of clear dispute that are the heartlands of the battlefield. Figuring out how to direct the jurors to the right pages of the instruction, the right questions on the verdict form, and helping them walk through that process—that's an art.

Khurram Naik: What would make a lawyer enjoy products liability work more than antitrust or vice versa?

Rakesh Kilaru: I'll fight your premise a little bit because I think we really enjoy both. There are different subject matter areas that are often touched on. In a products case, you're much more likely to have "hard science"—medical doctors testifying about the way a medical device or a pharmaceutical works in terms of biomechanics. Antitrust cases are probably a little rarer in that regard; you'll have a little more focus on economics and how economic principles apply. Some people gravitate to products work because they really love hard science, and some gravitate toward antitrust because they find that economic mode of thinking more interesting. From my perspective, I hope that I always have the ability to say, "Hey, there's something in this case that's really interesting," and then we're going to make that a core thing. I think we're at our best when we can figure out a way to make all of our cases enjoyable.

Khurram Naik: Apart from the sheer volume of information to help a jury wade through, what else would you say is a big difference between litigating antitrust cases versus products cases?

Rakesh Kilaru: I would say one of the big similarities that is a little bit underappreciated is the importance of non-expert witness testimony. In products cases, each side will have their retained and paid experts—doctors you retain to talk about the standard of care. In antitrust cases, you'll have retained economists; it’s kind of impossible to imagine an antitrust case without them. But decision-makers often view those paid experts as kind of coming out to a draw. We try to cross the other side's experts in a way that makes them appear less trustworthy than ours, but I have seen that jurors and judges often are just as persuaded, if not more persuaded, by the non-experts.

In products cases, it'll be the testimony of the individual plaintiff or the prescribing doctor. In antitrust cases, I think often it's really important for jurors to hear from the business people and hear what they're thinking in the real world. I think they know you can probably find an economist who will say the market is X or Y. But when you hear executives saying in real time outside of the courtroom—like in their internal emails—"We view X as a competitor and we really got to figure out how to deal with that," that can be super persuasive. There's something about seeing how things play out in the real world with real people that always seems more appealing and intuitive. A lot of times we'll hear, "Oh, we have the best experts, we're in a great position." I view that as table stakes; that’s the starting point, not the finishing point.

Khurram Naik: In the arc of an entire case, what is the part of the case you think you pay attention to that your peers or other skilled litigators don't pay as much attention to?

Rakesh Kilaru: I think one of the lessons I've really learned is to consider the source. It's not enough to just have people on your side saying something. It's about people who will be perceived as credible because they don't have as much to lose. When you get the other side to agree with you, or when people who are more dispassionate are agreeing with you, that really drives a point home. It's not just the paid defense they're presenting in court; this is what people actually think in the day-to-day.

The other piece is simplifying and cutting. I think often working with other attorneys, there is an innate impulse to preserve every argument and run through the tape on every issue so that later on you can't be second-guessed for leaving an argument on the cutting room floor. But if you're leaving all your options open, you're not giving the jury any real option. At some point, you have to make your decisions and have the courage to say, "Here’s what actually matters."

Khurram Naik: I think one of my favorite techniques for persuasion is starting a sentence with, "There is no dispute that..." because honing in on the commonalities makes you look very reasonable. It shows you're taking control of the situation.

Rakesh Kilaru: Probably 60% to 70% of the reply briefs I've filed start with, "There's no dispute that X, Y, and Z," and then follows with, "and so here’s what actually matters." I do think it's a useful tool for judges and juries; it makes everyone's life easier. Of course, you have to be right about that!

Khurram Naik: So let's talk about what you think Beth and Brian do that is exceptional.

Rakesh Kilaru: It would be hard to give an exhaustive list, but I would pick three things. One is that ability to make tough calls and figure out what matters. Often, other lawyers who've been working on a case will present to us for two hours on how the case has been worked up. Usually, Beth and Brian can say at the end of that call, "Here are the three things that I think we really need to focus on." Far more often than not, those are the three things we end up driving at trial.

I think a second thing they're really good at is listening. Most people think of great trial lawyers as speakers, but the skill that sets them apart is their ability to listen to what witnesses and clients are saying and react to that. In a cross-examination, it’s better for me if I can get the witness to say it than if I say it myself. That involves listening really carefully and using as many of their words back at them as you can.

Third is committing to creating opportunities for other people. There are so many fabulous trial lawyers who are super skilled but want to stay in the limelight. Beth and Brian are really good at figuring out what they really need to do as a first chair, and then using everything else as an opportunity for other people. From my own experience, in every case I've worked on with them, they sit down and say, "Okay, look, there’s a couple of things I really need to do because this is a make-or-break moment. But where can we create opportunities for Rakesh or for anyone else?" They put you in a position with the client where the client knows that you know the real record and can trust your judgment. Our firm has had more people handle witnesses than any other firm, person-for-person, and that starts with the two of them.

Khurram Naik: What are the biggest departures between your approach and Beth and Brian's, and in what ways are you cultivating that difference as an asset?

Rakesh Kilaru: I don't think I try to cultivate "difference" from them given their success. I think a large part of it is figuring out a way to do things similarly to them, but in my own way and in my own voice. It could be tempting to watch Beth do voir dire and try to do the exact same thing, but that's not going to work because I'm not her. They are always really true to themselves.

I probably do come to most issues from much more of the baseline appellate view of thinking through all the sides and angles. Both of them are very good at that but probably approach things more from, "I can pretty quickly figure out what the two or three through-lines are." I'd like to be more like them in that regard, but there’s some value in the way I think about things myself. Beth always says to younger lawyers, "When you're writing an outline for me, you should be thinking about: what if I had to do it?" Because if you are just giving inputs to another person and letting them run with it, you're not doing your job. You're not developing your own skill set. You have to put out what you think the right answer is so you can get their views on whether that was, in fact, the right answer.

Khurram Naik: Are there other things you do institutionally to de-risk what is ultimately a people business?

Rakesh Kilaru: Just continually creating more opportunities to test out our ideas. The more chances you have to present an argument to people who aren't familiar with it and get their reactions, the better our ultimate decisions will be. But I also think it’s about using those opportunities as a way for people to take risks, make judgments, and be wrong. In the government, I confronted so many different scenarios and made so many decisions—many of which I probably got wrong—but you just learn how to do it. Brian tried 20 or 30 cases as a public defender. That helped him the 31st and 32nd time. The more you actually do it and take the risk of being wrong, the better you are.

Many law clerks who come to the firm have never been told they're just flat-out wrong on something in their lives. They are sometimes afraid to do something they don't know how to do for fear that people will say, "You are not doing it right." One thing I think I did well when I started was realizing, "Boy, I do not know anything, so I'm going to be wrong, but I'm going to try." I'm okay being wrong 100 times because as long as I start getting it right around time 101, I'm okay.

Khurram Naik: What would make a trial shop hire an appellate lawyer from the White House?

Rakesh Kilaru: I wonder that often. I think when I interviewed, there were at least a couple of senior partners who said, "What are you doing here?" and "What makes you think you can do it?" But I like to think they thought, "This is someone who's talented and succeeded in some different environments." But more than that, I think they saw someone who's been around "clients" for the last two years. Every person I worked with in the policy councils or agencies was, in a sense, a client. They are people coming to you and asking for your advice and trying to solve a problem.

That is a skill that I think is generally translatable. Really successful trial lawyers are probably very good at communicating effectively with clients and understanding their concerns. I suspect they thought, "That's a skill set, and we'll see what happens on the trial stuff." I don't know if I'm "good" at it, but I know I like it, and I've been able to do it a lot.

Khurram Naik: Whatroutines are keeping you effective and helping you avoid burnout?

Rakesh Kilaru: Having young kids was such a great disciplining force. Before we had kids, my wife and I would both just be working like crazy at all times. But once you have kids, it’s non-negotiable. Man, I will tell you, there is no more demanding "client" in the world than a three-year-old at certain times of the day.

Beyond that, the answer is to build more time where you're not looking at your phone. Whether that's dinner time or carving out 4:00 to 5:00 PM when I'm on the road to FaceTime home. It's a lot harder than I wish it were. I have to acknowledge my own weakness in that. But having the aspiration to do that and being intentional about it is good for my family and good for me personally. Beth and Brian do a great job of that. If something is truly an emergency on the weekend, they will answer it, but they really try to be present with their families. It sets an example for other people that this is a better way to live life in this very high-stakes profession. There are times when it’s not possible—like when you're in trial for a month—but that makes it all the more important that when you are not in those moments, you carve out time for it.

Khurram Naik: Rakesh, this was really great. Thanks for getting on.

Rakesh Kilaru: Thank you very much. This was a real cool opportunity for me.

Business development creates differentiation when technical skills are commoditized.
Optionality multiplies this by developing multiple career paths simultaneously.
Affinity networks become firm-wide value platforms, not just personal networking.

Deliberate generosity treats relationships like portfolio diversification - invest broadly since you can't predict which connections matter.
Policy expertise becomes a defensive moat in niche industries.

Progress from "say yes" to strategic "no" to protect your systems while preserving ability to seize high-value opportunities.

Daily habits (20-minute social support + real-time alerts) create information arbitrage at scale.

Raw talent isn't sufficient. These strategies build transferable assets that maintain value across market conditions.

Keep reading below for the full link to the episode and the full transcript of our conversation.

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Top Insights

Below are the highlights of our conversation:

• Career Strategy should be built on "Optionality" and "Hedging": Dai Wai argues that legal acumen is merely a prerequisite, but the real "alpha" for a lawyer lies in creating multiple career paths simultaneously. He deliberately pursued three goals at once—making partner, preparing for an in-house role, and networking into litigation finance—to ensure he would never be stranded by a market dislocation. This strategy of "everything, everywhere, all at once" protects against the volatility of the legal profession where work can dry up or industry regulations can change overnight.
• Business Development is a Differentiator that Starts at the Associate Level: A central premise of the episode is that "people without books of business are fungible." Dai Wai suggests that associates should act like "owners" from day one. By bringing in even small clients at low rates, an associate demonstrates to the firm that they are a future rainmaker. He further suggests that if you aren't yet at the stage where you can bring in massive cases, you should build "institutional ownership" by leading associate committees or hosting business development lunches to mentor others, signaling your value to the firm's bottom line.
• The Flywheel of "Good Karma" and Non-Transactional Networking: Dai Wai views networking through the lens of "karma" rather than transactions. By being "a person of the people" (knowing the names of everyone from the receptionist to the senior partners) and helping others without expecting anything in return, you build a broad, resilient network. This relational approach creates a "flywheel effect" where favors and information compound over time. He emphasizes that the bar for being "extraordinary" is actually quite low—simple habits like setting up news alerts for former colleagues’ clients can make you non-fungible and keep you top-of-mind for future opportunities.

Full Transcript

Khurram Naik: Dai Wai, I've been looking forward to this for a while. I've known you for a number of years because I approached you to learn more about litigation finance. You were very generous with your time early on for this guy who was just a total rando to you. I've learned a lot about litigation funding from you, but in our recent conversations, I've really been enjoying talking about career strategy. I think you have some really differentiated ideas around how to approach career strategy that I think people would find very valuable. So let's start with your premise that business development skills are more valuable than, let's say, substantive skills, legal acumen, or horsepower. Tell me how you came to that conclusion.

Dai Wai Chin Feman: I think that first of all, thanks. It's a "sip of fresh water" to be on your show here. Thanks for having me—that's a little pun for you. But I got out of law school in 2010, which meant I was summering in 2008. I got a job at a boutique in Manhattan that was doing business litigation. Being at a smaller firm, not a bigger firm, you saw the value of a book of business. Growing up through the recession and seeing what that did to our profession, you saw how fungible people without books are. And so that made me realize a couple of things. First, if you don't have a book—and having a book is not a given—the people who have books aren't necessarily the best lawyers, and vice versa. Getting a book is difficult. So what do you do if you're an associate, especially because people aren't necessarily going to want to hire you if your name isn't partner? You have a chicken and egg problem.

What I did was I started bringing in clients when I was a junior associate. It was tough at low rates. My firm generously supported me in letting me have these very small engagements where I would put in maybe a tenth of my time just to start having the relationships. What I found was having clients is very gratifying. You care a lot more about the work when it's yours. What I also found is it makes you stand out very easily amongst peer associates. It not only makes you different than the other associates who just have their heads down billing hours working for that year's bonus, but it also shows the firm that you're acting like an owner. That opens up all sorts of other possibilities for you and lets you start playing that game and advancing in that ecosystem, because that's really what firms want to see. It's "up or out"—it's a pyramid for a reason. You need to be always generating that next generation of rainmakers. So who are they looking for?

Even if you're at a point in your career where you're an associate and people aren't going to hire you for the cases yet, you want to still have clients and show the firm that you're building business. I did things like becoming head of the associates committee at every firm I was at. Then I would host business development lunches where I would bring in the partners from the office, usually a man and a woman for each session, from litigation and corporate, and have them talk about client development over the course of their career to mentor other associates. That showed my firm that I was starting to think like an owner. That was very instrumental in helping me make partner. I didn't have a lot of clients at that point, but it was more that I had the promise of clients and also was positioning myself to inherit a pretty large book of business. My career strategy has been focusing on business development because it's a differentiator, but also relying on the fact that you need to hedge constantly.

You don't know when the next market dislocation is going to be that's going to dramatically transform the profession. When it happens, you need to have as many options open to you as possible. I think you and I both went to law school at a time when we were told it just opens doors and doors, and you don't even need to be a lawyer if you go to law school. I think maybe that used to be true, but now it's a lot more competitive. When I was going up through law firms, my goal was: I need to either make partner, go in-house, or do something else. That "something else" I had identified was litigation funding. But I need to go as hard as I can in all three directions and get as many options as I can because I might just have zero. Because of the way that I attacked it, I ended up getting all three. I ended up making partner, then I ended up going to litigation funding at Parabellum. It worked out well, but it was deliberate in the choices that I made to take my career in a way where I'd have such optionality. You'll never know if it was the right decision, but you definitely want to at least have the options and the freedom to be able to make those decisions.

Khurram Naik: I find in every success story that there's obviously has to be some consistency that paid off, and then you just have to make an assessment: if that shot didn't work, was this person using techniques that would help them get the next shot? Just a random example, I remember that Charlie Munger, when he was practicing law, said to himself, "I need to figure out who my best-paying client is." And then he realized, "I've been making these real estate partnerships. I'm my best client." That was his metric. He said, "Okay, well then how can I get more work out of me as a client? How can I do my own deals more?" He had a client for this wealthy individual who had this privately held business, and they had some land they were going to dispose of. Munger said, "Hey, don't do that. I'll develop it with you. Here's my proposal." They went in 50-50. Munger didn't even have to stake proportionally the same amount of capital. The deal was very profitable, but when I went to ChatGPT to stress test the assumptions, yeah, there was major risk in that one idiosyncratic deal paying off. He had effectively his entire net worth in this first deal. It was a huge amount of risk he was taking on, and very contrary to the kinds of risk he would stake recently. But the question is: was the process he was using effective?

Your technique as an associate self-reflects optionality. Bringing in those partners to talk about business development wasn't just getting skills; it was building a relationship with the firm and modeling, "Hey, here's why you should be investing in me." But you weren't limiting yourself to just that platform. You were developing business development skills tangibly in the form of clients. That not only shows ownership; that is ownership. That's the ultimate end game. I imagine you probably felt like you were late to litigation finance, am I right?

Dai Wai Chin Feman: A little bit. I started reading about litigation finance on Above the Law in probably 2013 or 2014 when a funder called Lake Whillans was pretty active on the scene. I got in touch with Lee Drucker from Lake Whillans—we had been in the same law school class—and he pretty quickly explained to me that, just like in practicing law, the "alpha" in being a litigation funder is origination and deal sourcing. Can you get the quality deals? There's a lot less competition, which is what's good about it. But I realized through speaking to him was that it took very few people to manage a significant amount of money for litigation funding. So the odds of getting into it were small, but that didn't mean that I shouldn't still network into it and prepare myself if the opportunity ever came along.

As I was up for partner, I identified litigation funding to the firm as an area where partners could be leaving money on the table if there were parties that came with valid cases but couldn't pay. They should at least know litigation funding is an option and have relationships with litigation funders. Then it becomes a source of business development for the law firm. I held CLEs through AABANY, the Asian American Bar Association in New York, where I brought in Asian lawyers at firms that had done funding and funders they knew, and had them present through AABANY to the partnership of my firm. Again, that showed my firm that I was acting like an owner and thinking about ways that could be accretive to the firm's bottom line.

Dai Wai’s daily LinkedIn practice — spending 20 minutes supporting contacts and building visibility — is something Sunny Kim has turned into a full coaching practice for lawyers.

Just like with the business development lunch series, that showed the firm that it wasn't just about me. I'm taking initiatives that will teach all the associates so that we'll all be bringing in business. You want to think about: what are all the things these people could be saying about me when I'm not in the room? I want them to think I'm a total team player, a total go-getter, and super organized. Another ingredient is being a "person of the people." Part of my philosophy is you have to know everybody and treat them like human beings. This whole JD/non-JD divide at law firms—I knew everyone's name, including the cleaning lady from my first law firm and the receptionist. You want to be in a situation where people can't say anything negative about you. When I got lucky enough to be contacted by a headhunter for this job at Parabellum, I was already up to speed on the industry. I knew how to talk the talk. I went to fine schools, but I didn't even try to write on a journal—it's just not me. I've now spoken at three law schools that I didn't get into, and it's worked out well.

Khurram Naik: I love that you keep on mentioning optionality. That's one of the meta-skills and values you have. I've never heard anyone suggest that it's not enough for people to think of you one way; it's beneficial for people to think of you in multiple ways. There's that concept from Scott Adams, the Dilbert guy, that you just have to be top 80% in three things and then draw a straight line through them to be successful. You're creating optionality for what people value. Maybe you thought people value you for your raw intelligence, but actually they rely on you for how empathetic you are.

Dai Wai Chin Feman: Yeah, for sure. You don't know what's going to hit. Doing good legal work is a prerequisite; it's just that a lot of people can do that. At the end of the day, what are you besides the hours that you bill? You can do so much through affinity bar associations like AABANY. I had a mentor who was the head of AABANY who gave me assignments every week and made me think strategically about my career. Through AABANY, I was pitching large companies and bringing partners from my firm to these sessions. Did I know if they were going to hire me? No, but I got to pitch to a real company as a third-year associate.

You need to think about where your vulnerabilities are if work tightens up. Or if you go in-house and the company becomes distressed, what resume have you built? How have you treated everyone you've known? I think it's really nice to work at a lot of places because you're in the trenches with people and you develop strong bonds. You need to be really nice to them, not just because it's the right thing to do, but because when you have favors to give, give them. Hopefully you'll never need a favor, but if you do, you want to have treated people in a way where it was not transactional. Inherently, in creating good karma, you're building relationships and skills that give you protection when there's volatility.

Khurram Naik: I couldn't agree with that more. I went to a non-target law school and graduated in 2013. I networked my way into BigLaw using bar associations. That "relationship-first" principle is the unifying theory of my career. My thesis is that network effects are a flywheel—as long as you are making connections between people, they compound and accelerate.

Dai Wai Chin Feman: Yeah, but it might have negative externalities. Am I stressed every day because I haven't gotten around to a pro bono thing for a friend of a friend? You can bite off more than you can chew, especially with bar associations. I had to take a step back because things like the Judiciary Committee can take 10 hours a week. You need to preserve time and freedom to do those extra things. There was a good quote at an AABANY event when I was a junior associate: you're a junior associate, it's 8:00 PM, and there's a networking event you should go to, but you still have four hours of work. What do you do? The answer was: you go downstairs for an hour and a half and you stay until 1:30 AM. I ascribe to that.

Career is sacred in our household. My wife is very driven. If work situations come up, they get deference. Generally, that has led to good outcomes. But it is all about creating those options; you don't just get them by sitting there and billing hours. I joined the New York City Bar Professional Ethics Committee. They wrote a damaging report about litigation funding, and I was given a policy role in the space only because I went out to try and get it. For every non-useful thing, there's 10 things I do that suck time out. Having that many shots on goal is really important.

Khurram Naik: We had already met by the time you got onto that committee, but you really blew up at that point because you were early to opine on this growing litigation finance change.

Dai Wai Chin Feman: Yeah, that led to opportunities I wouldn't have gotten—to be on other committees, to speak to the press, and to academics. A big moment for me was an industry conference where someone had written a damaging rule in the District of New Jersey about litigation funding. He was on a panel with me and I basically conspired with the other panelists to take him by storm and eviscerate everything he was saying because he didn't have subject matter expertise. That public dressing down helped me in the industry. Once you get that start, the network effects multiply. Now, litigation funding is nice because if you think of hiring a talented lawyer, there are 25,000 great lawyers in New York. There are only like 10 litigation funders. It's just a much smaller universe.

Khurram Naik: What are the drawbacks of that smaller pond?

Dai Wai Chin Feman: You're in smaller organizations and more dependent on the people who run them. Running a litigation funder is very different than a law firm. You also have policy attacks from the Chamber of Commerce, insurance companies, big tech, and big pharma. We're providing access to justice, which is controversial for some. I'm 40 now and I'm still one of the younger people in this space. Most people are on their third or fourth career. If someone needs to go to a state capital on two days' notice, who's going to do that? It ended up being me.

Khurram Naik: I would have thought that would be offset by accountability—that being small makes you mutually accountable.

The strategic career positioning Dai Wai describes — identifying a convergence early and building toward it — is exactly what Ambika Kumar did when she spotted the intersection of media law and tech from Seattle and built a nationally recognized First Amendment practice around it.

Dai Wai Chin Feman: You might not necessarily need it. Because it's such a small market, business development comes across to everybody. You can stay busy just being reactive, but you have to do the extra stuff if you're going to create "alpha" for yourself. If someone needs to call three litigation funders, you want to be one of them. It's not going to be because you funded some cases no one knows about; it's got to be more than that.

Khurram Naik: I think there's such a fallacy in the practice of law about "doing good work." It's not just about that. It's about your ability to message around things and have distribution for it.

Dai Wai Chin Feman: Yeah, having that voice is important. Even your Pony Cooler distribution—that lends something to the "air" of you. I spend at least 20 minutes every day liking posts of people that I like to give them support. How are you showing people that you're relevant? Hopefully, that'll come back to you. When money isn't falling from the sky, what are you doing to make sure that it does?

Khurram Naik: You're using some other tool for having conversations for other people's benefit. You've been extraordinarily busy with a specific bill in a very public way. It's not every day you face an existential threat in your field.

Dai Wai Chin Feman: Being involved in that increased engagement in my industry and created a sense of purpose. I'm able to use that policy work to hold people accountable who are "free riders" in our industry—people who benefit from our trade association but don't contribute. Until you cut a check to hire some lobbyists, what are you really doing to help the cause? Talk is very cheap. I have an official "shit list" behind me. Everyone has the opportunity to show what they stand for, and I'm trying to bring more accountability because I can now.

Khurram Naik: What's the technique you're using?

Dai Wai Chin Feman: A good amount of LinkedIn shaming and getting in touch with stakeholders who aren't pulling their weight. I tell them I'm the one flying to Columbus and you're not. It's generally been pretty effective. We're a small industry, but we control a lot of the money that moves in the legal profession. We pay hundreds of millions of dollars to law firms every year.

Khurram Naik: Is there one thing that you have found to be most persuasive in this way?

Dai Wai Chin Feman: No, I do everything everywhere all at once all the time. It's complete hedging. You need to have credibility where it counts. You need to get out and know the people and the academics. You need to have written some articles to show you're an authority. You want to create yourself as a broad, diverse platform that people are comfortable approaching. A lot of things come to me just because I did something nice for someone in the past. You want to do enough of that so you've got ample opportunities just in case.

Khurram Naik: This concept of karma is so interesting. I believe that often the right thing to do is just the prudent thing to do. Karma is just good diversification—being a good human being and being connected to a bunch of people in ways that are helpful to them. How did you arrive at that concept?

Dai Wai Chin Feman: I think it comes back to when you're a law student and you just hope someone does you a solid and gives you a chance. When you're on the other side, you don't want to waste an opportunity to give good karma. If I can go across my network and find someone the person they need, I'm helping out three people along the way. At the end of the day, at least you don't feel like an asshole. We give out mandates for millions of dollars of legal fees. When I have the opportunity, I'll give that to an associate in my bar association and make them the rockstar of their firm. Why wouldn't I do that? Imagine if someone had done that for me. Don't keep giving the business to the same people; diversify for others and you create all sorts of goodwill. There are people who have very big books of business who are not known for legal acumen at all. You need to understand the pyramid and where you're going to slot in.

Khurram Naik: You are probably the colleague that's referred the most number of lawyers to me. I know how much work that takes. What you're doing is very different.

Dai Wai Chin Feman: I think that's my highest and best use. You have to keep care of that network and stay in touch with people. A lot of people our age don't have a lot of friends from high school or college left, but if you keep in touch with them, they end up in different places. You want to be getting that karma of increasing the pot for everybody.

Khurram Naik: You can approach funding in a principal-preserving way or you can be looking for power law-type payoffs. Someone who is interested in optionality is inherently thinking about downside risk. Do you draw on the risk-averse legal skillset or the payoff-oriented one?

Dai Wai’s thesis that business development is the ultimate differentiator connects to something Hilary Gerzhoy told me — that confidence is the underrated trait of successful rainmakers.

Dai Wai Chin Feman: The downside protection has come out in picking cases with clear narratives. If you need to be a PhD economist to understand the value in an antitrust case, then that case has a coin-toss chance at best before a jury. Defendants are rarely willing to entertain realistic offers, so you're increasingly going to fact-finders. You want situations where your client is entitled to something kind of no matter what, at least as a quantum meruit matter. Parabellum has a strong emphasis on downside protection, but you end up pivoting towards diversified law firm portfolios. You need to be in a position of trust in the market. Where I've really had success is bringing business to law firms. Then they're more loyal to us. It helps with downside protection and diversification.

Khurram Naik: What is the top reason why defense-side firms are disinclined to settle?

Dai Wai Chin Feman: There are so many ways for a defendant to win. One way is outspending and outlasting the plaintiff. A defendant can win on a motion to dismiss, on summary judgment, on Daubert, or on appeal. In our top five jury verdicts, the defendant didn't put anything more than a few million dollars on the table, and these were all verdicts well in excess of 50 million. We’ve been focusing on finding things that are more prone to settle because you don't want that drag on the IRR that comes from a JMOL appeal.

Khurram Naik: Judge James Holderman in the Northern District of Illinois was someone who was a trial lawyer through and through. He loved trials as a judge. I remember I had a trial coming up as an associate and I was so excited. Then the matter settled. I saw the judge at an Inn of Court event and told him I was so excited and then it settled. Without missing a beat, he said: "Settlements always go to the clients." You mentioned that an antitrust case that hinges on an economics model is a coin toss. How do you balance story versus facts?

Dai Wai Chin Feman: You get to be more selective the longer you've been in this. I sourced an opportunity that was a hundred-million-dollar jury verdict. I had one of my friends from the Associate Leadership Institute take over the case and she stands to gain a 30-plus million dollar contingency fee. But the client was such a nightmare and had such a negative effect on my life. I don't know that I would do it again. The legal merits were what made it good, but other things made it difficult. You only get the luxury of that selectivity as you're more senior. Bigger deals mean a higher odds of fire. Learning how to say "no" in your career is very important.

Khurram Naik: I'm in that phase of my career where it's about saying "no." I'm an introvert, so I picked a very introverted profession as a legal recruiter. But I use social media as a tool to help people at scale. You're helping people even when you're not in the room.

Dai Wai Chin Feman: Yeah, I mentor a bunch of young Asian lawyers. I developed a list of tips for associates on how to make partner. Again, you're known for all sorts of different things.

Khurram Naik: It sounds like one principle you use is: "What can I do that nobody else can?"

Dai Wai Chin Feman: Yeah, that's the way to not be fungible. The bar is pretty low. Set up the news alerts and follow everything a client is doing. Information is power. I still know every partner I've worked with and who their clients are. I track mentions of them and case filings on Lex Machina. If their client has been sued, I let them know before anybody else. I don't want anything in return, but I would hope that if I'm ever in a position at a law firm, that someone is looking out for me.

Khurram Naik: Your livelihood depends on litigation finance, which seems not very diversified. How are you thinking about that?

Dai Wai Chin Feman: I could go back to a law firm and do plaintiff-side law, or work on the defense side valuing litigation. I prefer to keep doing this because it's more fun and not nearly as tedious as practicing law. Being in this business is being in an area of specialty finance. I'm watching hundreds of cases at a time, so the macro insight is very useful. That would make returning to practice a lot better than if I had just stayed all the way through.

Khurram Naik: There are equity partners and rainmakers whose success is based on legal acumen, and others based on business development. But you don't have to just give up just because you don't have a certain skill set. You just pursue it using a different skill set.

Dai Wai Chin Feman: You need to understand the pyramid and where you're going to slot in.

Khurram Naik: Do you want to talk about your last month?

Dai Wai Chin Feman: Basically, we were opposing a measure within Senate reconciliation that targeted our industry. There was no playbook for it. It shows how who's in power in politics can create environments where things are important that were never important before. For myself and others who do public policy, this is just the latest in a long string of attempts to counteract us because we upset the historic imbalance of power. Drake is not technically canceled from whatever Kendrick Lamar did to him, but we've got a lot of enemies in the litigation funding industry. We need to be able to drop everything and focus on big industry-wide issues. Everything you do has consequential effects around the perimeter.

Khurram Naik: You said any number of things you try will fail. That's an important message. You're looking for an asymmetric payoff. Talented lawyers are often unable to make changes because they are so risk-averse.

Dai Wai Chin Feman: You need to be committed to doing it. You need to stick with it and generate an opportunity set that's large enough where you have the probability of positive outcomes. I'm diversified in my Google Alerts every morning. You get better at it over time.

Khurram Naik: I approach my life pretty methodically with three priorities: my business, my family, and my movement. That gives me a lot of clarity. I think of you as being through the roof on being strategic compared to other lawyers I know.

Dai Wai Chin Feman: Strategy is driving everything. I'm in a place now where I don't think I need to be as multifaceted as before, but you need to be prepared and build systems where things that come up in your life are used to their maximum benefit.

Khurram Naik: I can't think of a better way to wrap the podcast.

Dai Wai Chin Feman: Thank you for letting me in the corner, Khurram.

In this conversation, Ambika shares how she identified the convergence of content moving online and tech companies needing First Amendment expertise, then executed a deliberate plan to become the go-to lawyer in that space. She breaks down her approach to client communication (short emails, phone calls over message chains, brutal honesty about odds), discusses arguing a 7:30 a.m. TRO hearing that blocked the first TikTok ban, and explains the evolving relationship between Section 230 and First Amendment protections as AI reshapes the landscape.

We also discuss the realities of building a practice while raising two kids, why "being eager" is an asymmetric bet that paid off, and what it takes to feel confident pushing back against more senior lawyers at fancy firms.

Keep reading below for the full link to the episode and the full transcript of our conversation.

Top Insights

Below are the highlights of our conversation:

• Eagerness as an Asymmetric Bet: Why being "too eager and ignoring non-verbal cues" as a junior associate didn't cost Ambika anything—and how showing relentless interest in learning, taking on non-billable work, and asking four or five times for assignments eventually opened doors that formal mentorship programs never could.
• The Section 230 / First Amendment Strategy: Ambika explains why tech companies initially avoided First Amendment arguments (fearing it would look like they're claiming a "constitutional right to host smut"), how that created over-reliance on Section 230, and why the NetChoice v. Moody case finally confirmed that online publishers deserve the same constitutional protections as traditional media.
• Communication Over Documentation: Why Ambika sends five-sentence emails instead of four-paragraph memos, picks up the phone instead of starting email chains, and believes talking through issues reveals tone and intent that text never captures—especially when clients are frustrated or co-counsel isn't hearing them.
• Building a Practice from a Non-Hub City: How Ambika strategically chose Seattle over media law centers like New York or D.C., identified the convergence of content moving online and tech companies in her backyard, and turned eagerness plus proximity into a First Amendment practice that handles headline-making cases nationwide.

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Full Transcript

Khurram Naik: This is Khurram with Khurram's Quorum. My guest today is Ambika Kumar. When tech or media companies have "bet the company" matters involving free speech, they come to Ambika. We discussed how she strategically built her career in the space starting as an associate. This is one of the most direct conversations we've recorded. Here's Ambika.

Khurram Naik: Ambika, I have been looking forward to this podcast for maybe a year. I don't know, it's been a long time coming, right?

Ambika Kumar: Yeah, it's hard to find a time.

Khurram Naik: It’s the longest I've waited to record an episode. No pressure, but I know it's going to be really good. We've just had a number of conversations for some time now, so it's just been really interesting to get to know you and your practice better. Something I'm really struck with is you're very down to earth, but you're also highly strategic. And so I'm interested in—I think strategy from our conversations is something that showed up really early in your career going back to law school, and that resonates for me because I think I was strategic in starting law school that led me down the path that I’ve been on. So I'm curious to hear—it sounds like you identify as a strategic person, taking a strategic approach to your practice substantively and then also professionally. Let’s start professionally. What is the role of being strategic mean to you? Like, how have you been strategic with your career?

Ambika Kumar: Well, I would say that I'm strategic in basically all aspects of my life to the extent it makes sense. In the context of my career, I went to Duke University and I graduated in 2002. While I was there, I was the editor of the student-run daily newspaper. It's probably the hardest I've ever worked in my life. And when I got out of college, I thought about becoming a journalist and realized that that was not necessarily what I wanted to do, in part because I wanted to have enough income to raise a family in the way that I was raised. And I thought, well, how about I go defend journalists? At the newspaper, we'd gotten a couple of demands that we had to talk with our lawyers about, so I'd been exposed to it from that perspective. I took a year off from college and then I went to University of Chicago Law School. Because I knew I wanted to work on First Amendment issues and issues for journalists, I did an independent study there with Jeff Stone, who is a scholar in the area.

Then when it came time to figure out what to do after that, I was researching firms trying to figure out who is sort of the best in the news media defense bar. There were two that were at the top of their game: Davis Wright, where I am now, and a firm called Levine Sullivan Koch & Schulz, which was a boutique in D.C. and New York. I interviewed with Levine Sullivan and didn't get a job. I interviewed with Davis Wright, and they were only really taking summer associates in their Seattle office. Sometimes we take from other offices with very exceptional cases, and so I realized that if I wanted to come to Davis Wright, I would need to at least start in Seattle. I split my summer between Davis Wright and Baker & Hostetler in D.C., which also had a media practice, although not nearly as robust as Davis Wright's. To me, the difference between the firms was night and day just from a personal aspect, but also substantively; I was doing more work at Davis Wright.

So I got married, took the bar, started my job, and moved to Seattle all in the same summer. I actually thought maybe I would move sometime to an area like the Bay Area; I actually didn't want to be in sort of the media centers of New York, D.C., or Los Angeles. I wanted to be at a place where I felt like becoming a partner was a real possibility and did not require working all day every day and sometimes all night. And so I came to Seattle thinking maybe I'll do a little bit of media work, it won't be everything, but let me see. By that time, it was clear that content was moving online. We had these tech companies in our backyard in Seattle and I was thinking we should be doing more for them. I mean, we already did do work for them, of course, but I thought I could find a place there. Between that and the firm's nationwide First Amendment media practice, I was able to build a career. I feel very lucky that I could do that sitting here in Seattle, which is really not a hub of media law.

Khurram Naik: How do you advise someone to execute on this? Any number of times, a lawyer might see some frontier of technology or some convergence of an industry. This is something that comes up a lot when we talk to lawyers who are early in their careers. There are things that they're really passionate about; maybe they wrote something in their law review or whatever. There’s just some topic that is just some interest of theirs, they're identifying something cutting edge, and they experience challenges with implementing that. "Hey, I'm just an associate, how do I move my career down this path?" I can see something, maybe everyone can see something, but the partners are embedded with their existing ecosystem of clients; they're not incentivized to build out some new practice maybe. There’s a variety of conditions that make it a challenge to grow in that way. How did you do it, and then what tips do you have for someone today who wants to take that strategic approach and converge their interests with the skills and platform that they're at?

Ambika Kumar: When I came to the firm, it was clear that I could not do only media work; there wouldn't be nearly enough. It was a very highly sought-after group. There was already one other associate in the group who was more senior to me. So I just did general commercial litigation. In fact, I had one partner in the IP litigation area who kept telling me, "Just get general commercial litigation experience, that's what you need." He was right, as frustrating as it felt at the time. Then when the firm circulates a list of clients for conflict purposes every day, I would look at that list—a lot of people do this—and I would see a case that had been brought in that I'd be interested in. I would contact the partner who was running the case and see if they needed help. I did this with one of my mentors. I did that and it was easy; we would just start working on it. With another, I think I had to ask him like four or five times until he decided, "Okay, I'm going to give her a chance." And then for me, the key was just doing really good work and not being a jerk, being personable.

Over time, I just got to know clients better and I was writing things. I think I was very fortunate to be at a place like Davis Wright because it is extremely collegial, and I think people are genuinely interested in developing associates who want to become partners. I also happen to be in a group where a lot of the rainmakers are women and had children, and that was for me a model. Although a lot of my models early on were men with families who were invested in their families and who would say, "I have to go do this for my kid now."

At the time, Davis Wright was sort of a regional firm, and so I think it was less—I don't know how to describe it—but certainly no one was doing document review day in and day out. People were actually getting—we had a one-to-one associate-to-partner ratio, which meant that the partners get paid less, but it also meant that the associates got the experience of multiple tenures of associates. They were doing everything from drafting motions to engaging in discovery and having client contact. So I think—I don't know, I can't say what would work today. I do think that finding people who can teach you how to do what you want to do is important and riding their coattails is important.

One of the reasons I came to Davis Wright was there's this treatise, a 50-state survey on libel law, and I looked at who authored the Washington chapter. It was Bruce Johnson, who was one of the mentors that I mentioned, the one that I worked with for a long time. And so I found him in my summer associate days and did work for him, and then I continued to work for him for years. I had a review once early in my career that was, "She's too eager and ignores non-verbal cues," which I found to be very confusing. And a couple of years later, the same partner said in front of a group of people, "This is Ambika, she's one of the most respected, if not the most respected associate in Seattle." And so what I learned from that was, even though I was being eager, that ultimately did not cost me anything. And in general, I think being eager can only help you. Showing an interest in learning, in feedback, not shunning projects that are non-billable—that's sometimes the best way to get to know somebody. They need help writing an article or a chapter or something like that, and you do it. Because it's non-billable, there's more time for developing a personal relationship because you're not charging anybody for that time. I honestly feel lucky that content and online just happened. I didn't go to law school for that purpose, I just saw it happening and I just happened to be coming to Seattle and I thought, well, this seems like a good opportunity. And it was.

Khurram Naik: Yeah, I've observed among other litigators particularly that I've had on this podcast that I think that's a formula for success: starting out at an established platform and growing in some way into some frontier that hasn't been occupied. Sometimes that is a geographic office that's a frontier, sometimes it's a practice area. But it seems to me that that's an asymmetric bet. And as you said, eagerness is a form of an asymmetric bet, right? Like, there's a downside to eagerness; it can backfire. Maybe you look too earnest and naive or some other negative qualities from eagerness, but in balance, nine times out of ten, eagerness will have some asymmetric upside. So I guess that's I think this concept of an asymmetric bet in terms of eagerness on something on the day-to-day or on the scale of your career, that seems to be another concept. Does that resonate with you, the concept of taking asymmetric bets in your career?

Ambika Kumar: Yeah, probably. I mean, I don't have—I’m not somebody who can say something I don't mean or who can't just be brutally honest. And so often times that means doing things where other people would not feel comfortable doing it, whether it's having an unusual conversation with opposing counsel about our relationship and how to make it better and trying to slow things down and make it less—or whether it's knowing what's going on in the personal lives of the people that I work with. If they don't want to tell me, of course, I don't push, but I do take an interest. And I share my own personal life. And so I think those things are probably things that most people don't do but that have paid off for me in my career and in my personal life.

Khurram Naik: Can we talk some more about the substantive aspect of your practice? Tell me about substantively, you know, maybe going back to your associate days, a strategic mindset you took to how you counsel clients, litigation strategy that differentiated you, that you feel like was original, novel, a departure from consensus?

Ambika Kumar: My early associate days, I was way too shy and too scared to say anything in front of a client, much less adopt a novel approach to counseling. You know, I grew up in a culture where the people that were more senior to me were sort of authorities to learn from and to defer to. And that is how I operated in my practice. Honestly, it's only in the last, I don't know, five to eight years where I feel like I am that person where I sort of know what the right thing to do is or what the—you know, it's just more natural. And so I don't have a problem doing it.

I had a situation once where we were counsel for a defendant and there was counsel for a co-defendant and they were at like a—you know, one of these top-tier firms. Not that Davis Wright is—I think Davis Wright is a top-tier firm, but often that is not the impression of other people. And this more senior lawyer at a different fancy firm was suggesting that an argument that I had suggested was not worth making. And ten years ago, I would not have pushed back. But I did this time. I think it's important to—I mean, part of that is getting comfortable with my own level of knowledge and strategic insight, and some of it is not being discouraged when somebody who is more senior to me and is a white guy says something to me that doesn't resonate and felt condescending and felt like I wasn't being taken seriously. Fortunately, I have clients, and so clients, you know, they get it and they know that I'm good.

And so, in terms of novel approaches—so I'm very direct. I do not overstate our chances; if anything, I understate them. I don't want anyone to be surprised if something bad happens. I tried a case many years ago early in my associate years and the partner on the case thought that we were going to win. And I was like, there is no way we're going to win. And I had to be really careful about what I said. And sure enough, we didn't win. But anyways, so I send short emails, they're not long. And this is like not novel, but I do see a lot of people at other firms just sending these like four-paragraph emails. They're not memos, because I think memos are mostly things that clients have decided they don't want unless it's something really critical. But they also don't want to have to read 20 sentences if it can be said in five. And bullet points are helpful, bolded headings so like if you're looking for like a part of an email that talks about our motion to dismiss, there's like a little heading that says "Motion to Dismiss." I find that helpful.

I also increasingly believe in talking to people as opposed to emailing with them. It feels like it's becoming a lost art, but I have one mentor in particular who was like, "Just pick up the phone and call. Why aren't you just doing it that way?" And I think there's a couple of things about that. One is people can be different in writing; they're much more comfortable acting in a way that you would never see them act in person or on the phone. Also, you can read the tone of voice as opposed to reading tone of text—you can't always do that. And you might learn more. I recently had a situation where one of the lawyers I work with, he's like, "I'm going to send an email to blah blah blah." I was like, "Why don't you call her? Because then you will get more of an insight into what she's thinking." And he came back and he said that was a good call, because I did. And so, I mean, that's not client-facing.

With clients, sometimes it's easier to talk through something because otherwise you get spun up in this churn of emails. I've had that where I've been co-counsel with another, again, fancy firm and the client calls me and says, "I'm really frustrated by this email exchange. I feel like no one is hearing what I'm trying to say." And that's just a lot easier to convey and it's easier to cut to the chase on a phone call.

Khurram Naik: Are you saying the client was included in the joint defense group exchange?

Ambika Kumar: No, this was my co-counsel, so they were also counsel for the client. I often get paired with larger firms higher up on the Am Law scale to provide my expertise on various issues like the First Amendment and Section 230. I'm also really honest when a client asks me, "Do you have this expertise in your firm?" It does me no good to be like, "Yes, this person who kind of has experience." If I recommend someone, it's because I know that they're good. And so I just pitched a case where the case is in a state where I don't often practice. State officials are involved on the other side. And I pitched it and I said, "You're going to really need to pair us with somebody who knows these people." And things like local counsel, they're critical because they have the day-in and day-out experience that you don't and can't have to let you know any quirks about the judges, anything, any particular views they might have about the issues in the case, because a lot of my cases are politicized, especially these days because tech companies are in the limelight.

Khurram Naik: Is your observation—do you think that the importance of local counsel is more important in state or federal court? Do you have a point of view on that?

Building a practice outside the traditional power centers — the way Ambika did from Seattle — reminds me of Randy Gaw, who built his trial boutique Gaw Poe outside the BigLaw system entirely.

Ambika Kumar: Probably state, but I think it applies to federal court. Depends on where you are, right? Like if you're in rural Texas, it doesn't matter whether you're in state or federal court, you need somebody there. If you're in New York, way less of a concern. You should still have somebody there to ask basic—but it doesn't have to be somebody—and it depends on the type of case. You know, if it's a case that requires a particular expertise that involves knowing the procedure of the court or the judges on the court, like that's important too. But if it's a run-of-the-mill piece of litigation and it's in a major city, local counsel to me plays a lesser role.

Khurram Naik: Can we trace back to what was that path from commercial litigation to some of these high-stakes tech and speech disputes? And part of the question is also, I mean, you initially were very interested in the media tech litigation and you represented journalists and now you represent platforms. Can you talk about those two evolutions in your practice?

Ambika Kumar: I never—I mean, I did represent journalists for a good bit of time when Washington had an anti-SLAPP statute in particular. The news media had the resources to pay for their defenses and knowing that they would get their fees if we won. That statute was held unconstitutional, I don't know, it's been at least 10 years. And that work kind of died off. And the reality was being in Seattle, I was never going to be like a premier journalist defense lawyer. It's just something I had to give up. And frankly, something that's extremely competitive. Not to say that the area I work on is not competitive—I mean, it is, but it wasn't when I started. It wasn't as competitive, it didn't feel. I think that I just—if I saw the firm was litigating something related to content, I went after that case, went after the lawyer, asked if I could help. And the more that I did that work, the more exposure I got to other clients with similar work, and those clients happened to be platforms. But you know, I've certainly had help along the way, other work that has been referred from lawyers that I work with, which is flattering because it suggests they think I'm a good lawyer but also that I'm relatively easy to get along with, at least in the professional context.

I would go to conferences that were around the subjects that I—but they weren't my main—never did I go to a conference and think, "I'm going to get work from this" or "This is really going to significantly—" You have to go to them repeatedly; you have to see people year after year. And you also have to rely on your partners to introduce you to people, which I had. I had one person who would be like, "Look at the RSVP list and tell me who you want to meet, I will introduce you." And those things are really important because they're just the seeds of something that can grow later.

Khurram Naik: In picking up this clientele and starting to get experience in First Amendment, Section 230, I'm curious: what was the inflection point or points in your career? Like, what was the first inflection point in your confidence, skill set, the stakes of the matters you're working on in that space?

Ambika Kumar: I mean, the first high-profile matter on which I was lead was the first TikTok ban. Before that, I had worked on cases that were important and prominent and written about in the news, but I was usually a part of a team. So all my bios would say, "Part of a team that…" or that kind of thing. So it's really just been the last five years that I've felt this confidence. I mean, it was growing, right? It wasn't like a switch. I got increasingly comfortable pushing for what I thought was the right decision. And when I started, when I think when I got—there was like this MVP award for Media and Entertainment a few years ago that I got, and then I was like, "Wait, like maybe I have a profile that's not local or tied to someone else but that is just my own." And then the Wall Street Journal, after the first TikTok case, wrote an article in which they said, "They hired top First Amendment lawyer Ambika Kumar." And I was like, "Whoa, that's crazy! Is that me?" And so those things have certainly helped.

What has helped the most probably is the reassurance of the people that I work with who are much more senior to me who, when I'm ever slow—which yes, it still happens—are like, "You're going to be fine. Go take a vacation, take the day off." You know, from when I was an associate, "You're going to make partner, you're going to make equity partner." I didn't have the confidence. I only went up for partnership—and this was the year after my first son was born—because somebody said, "I think this is your year." And I said, "Really? Like I just had a kid, are you sure?" And he's like, "Yes, I think this is the right time." And I did and I got it. And then I went up for equity partner the year after my second child was born, I can't remember, somewhere around there. And so, you know, part of it is the firm has supported me immensely over the years in my career development and trajectory.

And you know, when I—I will never bill as much as I did before I had kids. It's just not going to happen. And I don't want to. And I think Davis Wright is willing to make investments of that sort knowing that, you know, I'd established a reputation: I was really hard-working, I was good at what I did, I had a kid, of course my hours were going to drop, how much we'll see. And I went through a divorce while I was at the firm. I never felt like pressure from the firm to minimize my personal commitments in order to bill more hours. And that's been easier the last few years because I generate business in addition to actually doing the work. And so generating business doesn't cost as much time, right? Like you've got a reputation, you write a client, you say, "I saw this was filed, would you like help?" And ten years ago, the chances I would get it from just that were minimal, and as time goes up, they're much higher. They're still not like super high or anything, but you know, there are now times where a major company I pitch for a case and I feel like it's like a 50/50 shot, which actually feels like a pretty good shot.

Khurram Naik: You have a couple of really wild stories in—I don't know if you'd consider them inflection points, but just maybe they're just tangible career catapult moments. But I'm thinking of the first one I'm thinking of is a TRO that you argued at 7:30 in the morning on two hours' notice. Can you share that story?

Ambika Kumar: Yeah, it was a Friday in 2020, I think September. So 2020, I would have had a few—no, not 2020, it was earlier than that. I don't remember when it was. My kids were small. I had two small kids and so they wake up early in the morning and sometimes in the middle of the night and all that kind of stuff. And President Trump banned TikTok. Times have changed. And or maybe times haven't changed and he hasn't either, but we got the executive order and I wrote a TRO motion in a day working with one of the litigators and then just filed it that day and I went to bed feeling like totally—it was one of those days like I was in my pajamas all day long, I didn't eat very much, I was just focused on getting this done.

And you know, so I was relieved to go to bed at night. I was like, "Oh, I'll get to sleep now." And like many people, I have a bad habit of looking at my phone sometimes when I shouldn't be, when I should just go back to sleep. But that habit was reinforced because at like 6:00 or 6:30, I looked at my phone and I saw that the judge had set a hearing for 7:30 Pacific, 10:30 Eastern because the case was in Pennsylvania. And I was working with a couple of other attorneys, one of whom was much more senior to me, and I called him and he said, "I was debating when to call and wake you up." And so he said, "So it's good you're awake." And this was during the pandemic.

And I went down to my—so it was a virtual argument, like one of the first ones I did or maybe the first one. So I went down to my basement trying to figure out—like I don't actually work at a desk at home, so like that was not an option. So I set up this crazy area where I had a side table with a box of like a fort building kit box on it with my laptop on top of that and my seat was the back of an exercise bike that had been torn to shreds by the cats that we had. And of course, I did not have my actual background, like I had a fake background. And we had the hearing. It was a lot of fun, but you know, and then I was done and I was like, "Okay, back to my Saturday life." I can't remember if we got an order, but it was definitely a hearing that went well. And unfortunately for the government lawyer, he had been like, I think even out of town or something and hadn't even seen the papers really, and so I felt bad for him because it's not like he knew the record very well; he couldn't know the record very well. And we got an injunction eventually. I don't remember if it was from that hearing or another; there was one that I feel like she said it was premature, something like that. So yeah, that was crazy.

Khurram Naik: And then wasn't there also another Saturday injunction hearing in another matter?

Ambika Kumar: I don't think so. You might be thinking we represented AWS in a lawsuit brought by Parler. Parler is a social media service—was a social media service on the right, sort of politically. And this was after January 6th, before the inauguration. And you know, it was made headlines: AWS suspended or restricted Parler's account and then Parler sought a TRO that would require AWS to restore its service. That one I remember I was going through a divorce and I was staying at a friend's house and I remember pacing the halls at her house practicing my argument. You know, there was a lot of prep including with other lawyers and including the client. So I remember that one vividly too because it was also very fast-paced and I was not even in my own house and it felt odd. And it was pandemic, so I couldn't go to the office either. So I was just sort of in this visiting—and the friend whose house it is, she was gone, so it was just me and my dog, my pandemic puppy. And I just paced the halls and practiced my argument and then I did my argument at a side table in her bedroom overlooking the water, again with no background. But I mean, pandemic definitely put me in some odd places physically to make arguments. It was kind of fun actually; started like thinking, "Like should I try to make sure I do it in this kind of room or that kind of room, like the kitchen?" You know.

Ambika’s approach to relationship-building — proactively seeking assignments, reaching out to partners repeatedly — echoes what Dai Wai Chin Feman calls “non-transactional networking.” He built his entire career on deliberate generosity and creating value for others.

Khurram Naik: I want to pick up on, you know, you're talking about your kids as part of your routine and the timing of the kids, and it seems like kids are your lucky charm, so just you know, if you want to level up in life, have a kid I guess, it sounds like. Do you feel like having children has influenced how you practice? You mentioned not billing as much, but you know, focusing things on things like, you know, you are by definition working reputation and so then you can focus on business development which is higher ROI for the amount of time involved. Is there a strategic dimension to having children? I had a recent interview with Laura Kruslich, she’s a litigator at Goodwin, and she talked about the ways that having children for her has made her more strategic as a litigator because in the past, she would have taken on every aspect of a case and enjoyed owning every aspect of a case, and now she realizes she has to take much more of a team approach and say who is the best person for handling this aspect of a case. So I'm curious for you whether you feel like having children has influenced—I keep on using the word strategy, so you can ignore the word strategy or supply some other word—influenced how you practice? Like has there been some sort of reciprocal relationship between having kids and how you practice?

Ambika Kumar: Well, definitely I delegate more. That’s a consistent theme. As one should as one grows more senior, but it's much easier when you have kids and there's something else you have to be doing. It’s a hard skill to develop and it's one that I try to tell people I work with, like try to help them, "Like why are you online right now? Go, go." And I think that having kids can change the way—change your personal interactions in a way that can be, I suppose, advantageous in the sense that some of the cases I work with are about tech companies and children. Having children gives me that grounding of thinking about like: Should my children access social media? If so, at what age? What restrictions should be on there? Should I be able to see everything? They're little right now—not little, but they're not of an age where they can reasonably demand privacy. And so, you know, some of those issues are still coming.

But I think there's something about having children yourself as opposed to having a colleague that has children that just changes your perspective, I think. And I talk to my kids about work. I actually practice because if I can explain it to my 12-year-old, I can explain it to a judge. He asks good questions. Client development efforts sometimes involve family now. I've taken a client and his son to a hockey game with my son. That part has changed too. I have a lot of female clients and there's a lot of conversation about our kids; it doesn't feel gendered, it feels like this is just my life. And so I can't say that it's helped me develop business in any direct way, except through friendships with parents of students in the same school, for example. Like that certainly has happened, but otherwise, you know, I stopped working on the weekends for the most part. And I try to make sure that other people on my teams aren't working on the weekends. I always tell them, "If you can't make a deadline, please check in; it may not be a firm deadline and we might be able to—" Oftentimes like I have a deadline for someone to get me something and then I'm like, "Uh-oh, I'm busy with this other stuff, can't review it right now." And so I'm just like, "Take it back. If you're not done, feel free to work on it some more." But yeah, those are the ways in which kids have changed my approach.

Khurram Naik: And then you mentioned tech views around the challenges that tech companies are having now around privacy, around addiction, you know, different aspects of social media use for children and questions about that. How do you reconcile the needs of a client and your personal views around how you want your children to interact with social media and what you expect from a social media platform? Like, how do you reconcile those two parts of your life?

Ambika Kumar: I don't think there is a lot of conflict between them. I really do believe that it is my job, not the job of the law, to teach my kids what social media is, how it should be used responsibly, whether it should be used at all. I mean, my kids—I haven't reached this point yet, but like should they want to engage in social media, I'll help them navigate it. And I do wish sometimes that on some services I had better tools to limit, for example, limiting access to specific types of content or specific content while allowing others. That can be hard to customize. And part of the problem is that because we, as a society, seem focused on making the platforms responsible for what children see online.

And you know, I've seen some arguments that are really like—I don't want to say frivolous, but they are not good arguments. Like I had one case where the client's terms of service said something like—it was an adults-only platform, it made that clear, it said by entering your date of birth, you're certifying that you're over the age of whatever it was. And then in a separate part, it said "People under the age of majority or minors may not access the service." And the claim in the case—one of the claims in the case—was that means you guaranteed in your terms it was physically impossible for children to access your service. Like, it's just a completely unreasonable reading in the context; what it means is you are not allowed to do so, not you physically can't do so.

And I had another case where the other side was adamant that my client should be able to verify the ages of its users. Now age verification is not like "flip a switch and it's done." It can't be. And it also has serious privacy issues. That's not to say that one day we might not get to a place where like that is a thing that we do, but we're not there yet. And I remember asking opposing counsel, I said, "What is it that you want us to do? Like how—like it's not possible right now." And the response was, "That's your problem, not mine." And so I wish that we had a more cooperative relationship with the people who have these concerns. We being—I wish the tech companies and government could work together on things as opposed to just—I think it's different in Europe; here it's very much like "We're going to pass this law and then we're going to penalize these guys until they comply." And often those laws are unconstitutional and it's counterproductive because then the real problem is still there. Like I really do want parental controls that are more tailored—that I can make more tailored for my kids. I could probably go look for one and probably find it, but it sure would be nice if it was like advertised or the government was like, "Here are some ones that we think are good" or what have you. But I don't—and in some states they do have that—not that specifically but like education for parents. But it just doesn't seem to be the dominant way that people attacking tech companies think about it.

You know, I'm a lawyer for in one of these—in some of these cases alleging that video games are addictive to children. My children play video games. And once again, when I see in some of these cases the number of hours a child—and the age at which their child—like, so-and-so started playing at the age of three. So-and-so spends 15 hours a day playing video games. Like, I'm sort of just wondering like what is going on that has made this possible and to happen? I hate my kids playing video games too much, I don't like it. And it's a constant struggle. And now that they're getting older, I can at least explain why I don't want them playing video games as much as they are. But they're not playing, you know—they didn't start playing at age three and they're not playing 15 hours a day. And I can't fathom that ever being the case.

Khurram Naik: "Hey, like you can watch with some frequency"—at this point it's become daily—"like videos of garbage trucks and construction." Those are the two ones, I love it. And then we also pair it with—and I have mixed feelings about this—pair it with meals because I've observed just like an adult, you're more likely to eat more when you're distracted, enjoying something. And so he eats pretty well as it is, but then we'll put that in front of him.

Ambika Kumar: He'll just be like, "Mmm, yum." My kids are—one of my kids I learned in therapy with him, he was in therapy, and the therapist has these fidgets everywhere. Fidgets were not a thing when I was growing up; like you did not—it was like you should not be paying attention to something else or messing with something else while you were also paying attention to a conversation. And also at my kids' school, the head of the intermediate division who's a good friend—I mean, she's no longer in that position—but her office was full of them too. And I was like, "Oh." And one day my son had a fidget he was taking to school and the nanny was like, "Do you really want him to take this?" And I was like, "I don't know." And so I asked my friend, I was like, "What do you think?" She's like, "Yeah," and it's permitted in school. And that's because if they have something that they're doing like this—and I find that I am the same way—I pay better attention. In therapy, talking about painful issues is easier if you're like throwing a ball back and forth or doing something that takes the sting away somehow. And so with my kids, you know, I feel the same way about drinking; like I'm not certainly not—he's 12, he's not going to be drinking alcohol anytime soon. But at some point, I will introduce it to him to make sure he knows how to do it responsibly. And that's all I can do, like I view my job and my role is to turn them into happy, good people. And part of that is knowing how to navigate the world as an adult. And we got him a watch when he was nine or a phone, and maybe ten. And it wasn't—he doesn't play games on it. It was because he's an anxious kid, and when I was late to pick him up for something, he would get just terrified. And maybe that's something he should have to learn, but like in this day and age, you really don't, right? Like as an adult, like you just text and you say, "Hey, I'm running a little bit late." And so, you know, it gave him peace of mind and it made me feel less guilty being late to places because I knew he would hear from me that I was just running late.

Khurram Naik: Yeah, and so I'm curious, your work seems very distinct to me in that I was a patent litigator, and so the relevance of public opinion is fairly low. To be fair, most of my work was bench trials, so I was far less exposed to popular sentiment. But your work is virtually inextricably linked to public sentiment. So I'm curious about—I’ve never had very satisfying explanations for our relationship with tech companies. Maybe the best analogy that I can make is, growing up in the '90s and 2000s, a lot of the backlash was toward companies like Walmart, which clearly most people used, but then had these very ambivalent feelings about and just also hated. And so they're the target of public ire. Or like McDonald's, let's say, with Super Size Me or whatever. So with tech, I'm curious to hear from your vantage point—I mean, you've been in Seattle for a period of time, and so you've seen the growth of tech companies there. Seattle's had this kind of—its relevance in tech has kind of fluctuated over time and kind of just gone in this very spiky process of upward and then down and then much higher. And so it hasn't been like this steady. And then also public sentiment on it, I think it's been kind of mixed in terms of like how much we love it or hate it. So I guess, can you speak to how the role of sentiment, tracking sentiment, being strategic about sentiment, policy—like how does that play into your work? Like, how do you weave legal reasoning, strategy with this sort of sentiment component to your practice? It just seems like a really unusual way to influence your practice, I'm not sure how.

Ambika Kumar: Well, look, the clients are businesses, and what's good for the law is not necessarily what's good for the business. And so when advising clients, I think it's important to understand what their goals are. And in these cases that are very high profile and very, you know, sometimes have very disturbing facts, there are strategic reasons to do various things. For example, sometimes clients have an arbitration clause, and the reason for that is so it does not have to be litigated in the public sphere, right? I think the popularity of arbitration clauses has waned over time to some degree for a variety of reasons. But some clients just won't make an argument because they think—I mean, I think for many years, I think some companies were reluctant to use the First Amendment in a way that said, "You know, we didn't know this content was on our service and so we're protected," because they viewed it as basically saying, "We have a constitutional right to have this smut on our service," right? Which is not that different from what Section 230 says. But the result of that was that Section 230 took off, and there was a lot of law developed in it, and the First Amendment law stagnated in the tech sector until people were like, "Oh, we better pay attention to the First Amendment too," culminating in the Moody v. NetChoice case.

The way Ambika navigates parenthood and a demanding practice — making partner after her first child, equity partner around her second — is a tension Priyanka Timblo also confronts head-on. Priyanka tried a case at eight and a half months pregnant and rejects the word “balance” entirely.

But because I come from a firm that has such a strong First Amendment practice, you know, a bunch of us felt long ago that it's sort of foolhardy to rely only on Section 230, which can be repealed, to the exclusion of the First Amendment, which is, one would hope, never going to be amended. So it’s interesting—I haven't had people ask me "How do you do this work?" or things like that. You know, I think it's interesting your comments about Walmart and McDonald's. I'm trying to think how analogous those are. I think—so Walmart, you only go to Walmart if you need something. You only go to McDonald's if you need to eat something. Technology is the source of everything in some ways. And so there is no way, even if you didn't want to use Walmart or McDonald's, you could do that, but you can't not use technology really and function in society.

And I grew up in the '80s and '90s where I had an analog childhood—there was none of this. But and so there's good things and bad things about it. You know, I think the important thing in any case in this field or not is to tell a story that's compelling, to have a narrative that's going to resonate with a judge. Because judges fundamentally want to do the right thing, right? They want to be able to find a doctrine that tracks what they think is the right result. And so whatever you can do to give them peace of mind that if they dismiss a case, it's not going to be the end of the world for another set of plaintiffs or, you know, really the client is a good actor and these are just bad facts. You know, sometimes these cases involve children who have died by suicide. Those are very hard cases because the harm is so great, even if it wasn't caused by the tech company but by third-party content or what have you, a host of factors. And those are cases that you know—I have a different approach in cases like that in terms of whether to settle, when to settle, what arguments to make.

Because the reality is in the law that suicide is an intervening cause that generally gets rid of liability for the tech companies. But we don't, you know—it's not like we go around—like I don't go around saying like, "Let's say this." It's kind of not an argument that appeals to one's sense of good and justice and fairness, right? What might resonate is these are the specific circumstances of this child; here are all the things that were going on in their life, here, you know, that kind of thing. And so but you know, that needs discovery a lot of the time, so it's hard.

Khurram Naik: Can you just, on a substantive point, can you go back and just briefly explain the relationship between Section 230 and the First Amendment jurisprudence in say the past 10 years? I know that's a big question and a lot to explain there, but for people that are—it's obviously a hot topic but a lot of people maybe they saw some dry summary of a Supreme Court decision recently and just their eyes glazed over.

Ambika Kumar: Section 230 was passed in 1996 and the purpose was at the time, you know, we didn't really have the internet. I mean, we had the internet but most of us did not. And at the time, the—you know, at common law, arguably a service could be responsible—like an AOL or a Prodigy could be responsible for the content that it hosted that other people posted. And Congress didn't want that to happen. Actually, Congress passed an omnibus law that was like, "You can't send harmful content to minors, but also here's this like exception to liability for third-party content." And most of the law was struck down and what survived was Section 230. And so over time, it has been expansively interpreted to protect publishers that host third-party content that allegedly is harmful.

And it has been litigated a lot in the last probably 15 years because it is such a strong immunity and it's one that kills lots of cases. And so it was designed to foster the First Amendment on the internet. It was designed—so in the brick-and-mortar world, in First Amendment land, if I'm a bookseller and I have obscene books in my collection that I'm not aware of, I'm protected. If I know they're there and I know they're unlawful, well then I'm not protected. With Section 230, it doesn't matter what I know or don't know, and the reason for that is because when a service polices its own content, it is incurring a risk of liability because then someone can come and say, "Okay, you vetted your content, but like you left this one out there." And the number of messages that we're talking about was just staggering. And so what Congress did was say, "Okay, you're just not going to be responsible for that. Like you're going to self-regulate, you're going to police your own service, and no one is going to be able to come after you and say you missed this one piece of content and so you're liable."

And so they are complementary of one another. And I think people don't always understand that. I frequently get the question, "How can you say that your client's a publisher but also entitled to Section 230 immunity?" And the reality is that Section 230 immunity applies to publishers. Like the answer is: these publishers won't be treated like publishers at common law if the harm is stemming from third-party content. But it's not necessarily intuitive and it does require an attention to detail. And I think that state legislatures down to municipal governing bodies, they're not concerned with the details often. Which as a citizen I find disappointing because I can—you know, if I were in government, I could think of much better ways to do regulation in this area, and I'm sure that's true in all other areas of my life. And in this area at least, whatever is politically popular is what's going to happen, and that's not always what's the most logical result.

Khurram Naik: And then, I’m sorry if I didn't understand it fully, but then what was the relationship with the First Amendment jurisprudence, like how did that—now it sounds like—?

Ambika Kumar: Yeah, so the relevance is that the First Amendment was being applied in the brick-and-mortar world and not on the internet ever, really. Even though there were principles that we now know from the NetChoice v. Moody case, which made clear—there was this reluctance to treat online publishers the same as brick-and-mortar publishers, this idea that tech companies and tech services and social media services were somehow different and so we're not entitled to the same protections. Even though what they were doing was the same thing that publishers have been doing for a long time. So there's a case called Tornillo—I can't remember if it's Miami Herald v. Tornillo or something like that—at the Supreme Court where some negative thing was written about a politician and I think Florida had like a "right of reply" law requiring the newspaper to host a response. And the court said, "No, no, no, like what messages you include, that's your—you have that right." And the same is true with social media and tech companies. They have the right to decide what mix of content is going to be on their services, to figure out what kind of communities they want to create, what they want to tolerate, what they don't want to tolerate. It's all about organizing content. And so the First Amendment principles apply equally to that as they do to Section 230. But because people were reluctant to make those arguments, Section 230 kind of predominated for a while. And then when politicians were like, "Well, maybe we should get rid of Section 230," people came around and started making more of the arguments that, as I said, culminated in the NetChoice case, which held that services that are arranging, editing content, etc., are publishers under the First Amendment and entitled to the same protections.

Khurram Naik: Yeah, I can’t remember where I read this years ago, but it is pretty fascinating that someone made the assertion, and I haven't disagreed with it since then, that media businesses are fascinating because the existence of the business is constitutionally protected. I can't think of another business model that's protected by the most core tenets of our government.

Ambika Kumar: I mean, the gun industry is protected by the Constitution.

Khurram Naik: There you go, that's a good one. Can you speak to—an obvious, we talked earlier in the conversation, you were talking about identifying a change in technology that a body of law is going to be applicable to. And so you recognize that tech companies are becoming publishers and so there's new terrain to be—new clientele to be working with, they're in your backyard. So you saw this convergence happening there. A very obvious convergence is now AI. That's this new frontier that potentially Section 230, First Amendment applies to and some disputes around that. How are you thinking about this new frontier?

Ambika Kumar: I mean, million-dollar question, ten-million-dollar question, I don't know. You know, because the firm represents content creators and traditional publishers as well as tech companies, you know, we see the arguments on both sides. And for the most part, on some issues, we just stay out of the fray because we can't take positions that are inconsistent, very inconsistent, between those two. And so I mean, it will be really interesting. I do think there is a chance that at some point, I don't know when, the Supreme Court decides that AI information generated by AI is subject to lesser protection than corporate protected speech. So, you know, commercial speech has less protection than non-commercial speech. I could see the court saying the same thing here, like—and the reasons for that in the commercial speech context, the idea is that commercial speech is more robust, that companies are going to advertise, they're not going to be chilled by regulations of advertising because it's to their extreme benefit to advertise. And I think probably there is going to be some kind of similar analysis that the generators of AI stand to benefit from improving on AI. And so maybe it will always exist and will never really be chilled, and so the reasons we afford protection to political speech, which is much more easily chilled, don't apply here.

So I haven't seen that argument made by anybody. I could see making it, but it would have to go up very high in the appellate courts to really gain any traction. And much like we were just at the beginning of Section 230 and the First Amendment stuff 15 years ago, I think we're just at the beginning of whatever this is going to become. And I don't know what it is. Because the other thing is AI is always evolving and changing, and it's not something that's fixed.

Ambika’s success in converting non-billable work — articles, treatise chapters, conference panels — into practice development is the kind of strategy Sunny Kim now teaches lawyers to do on LinkedIn.

Khurram Naik: Is there anything different you see about the ecosystem of AI businesses versus the tech businesses you saw some years ago and the impact that would have on—I'm just thinking about a young Ambika Kumar today. Like, what would she be seeing as "Hey, how do I create the opportunity on my platform to be servicing either the copyright holders or the AI companies?" How would you be thinking about—is there something different about this ecosystem or conditions today, maybe at law firms as well, for how someone—you—at the stage that you were identifying this opportunity, would act?

Ambika Kumar: Well, I’d be thinking about who cares the most about this. It's content creators, content generators, but also content users. And I think there's probably some room for growth in the area of helping companies who want to make use of AI. I just read an article the other day about AI and medical advice, identifying cases where somebody was able to find a treatment for whatever they had that had not been identified by their doctors. That seems like a really beneficial thing. And I have actually used such technology, even though I'm the daughter of two physicians. And you know, I don't know what's going on in that space, but it wouldn't surprise me if there are copyright issues, if there are issues on relying on the advice. Even though there's probably a disclaimer somewhere that says you shouldn't rely on this, someone's going to be like, "I relied on it."

I think every industry is having to figure out how to integrate AI. And so there will be a range of claims from employment claims—like, my reviews were generated by AI—to you just saw that the California bar admitted to having some questions generated by AI for the bar exam, to medicine like I mentioned. You know, I'm sure it will affect every industry. And I guess I wouldn't be so focused on the tech companies, even though I live in Seattle, because it's going to affect more than just them. And it's going to be in areas outside the copyright context too. All of that will be an interesting thing to watch. And then there's a question of how does Section 230 apply to AI? You know, when I pull up—I mean, this has already been decided—but like, for example, when I pull up a map and I'm looking for, I don't know, tailors in the city of Seattle and I get like a few options pop up, what if it's wrong? Is that the service's fault for giving me the wrong information or not? And we know that that kind of thing is protected by Section 230 because it's been decided at the circuit court level. But that's just a form of AI, right? It's a form of taking information and putting it in a different format and you know—and maybe even like, you know, recommendations are a big thing right now. So yeah, I don't know that I have a specific area that I would practice in or look for, but you know, the news is just as good of a source as anything on what's coming.

Khurram Naik: And I'm wondering for you—you mentioned, "Hey, when I'm in a position now where I can pitch, and you know, maybe 10 years ago it would have been a long shot, but by virtue of having serviced some of these companies and clients and your reputation, maybe with clients you haven't represented or companies you haven't represented, you've boosted the odds of getting this work." How do you—it seems to me that someone in your position could be balancing two different things: one is picking up work today where there's an opportunity, you've got a set of tools that of course expand and the law changes, but you've got a playbook to apply to companies and so you could just run that playbook. Or you could be spending more time thinking about—you’re doing some of this, talking about some of the evolution that you expect of either jurisprudence or pervasiveness of the technology and who it would impact, who are potential clients, potential people that could be affected by laws, and spending more time identifying some frontier of your practice. It seems to me that there's some sort of balance to be had between frontier work for you and executing on that playbook that you have today for clientele. Does that sound right? Is that something that you balance?

Ambika Kumar: Yeah, for sure. I think it's kind of scary for people who are used to doing one thing for a period of years to think about a big jump to something else. And it's not a huge jump, but it is a jump. And lately, I have been feeling a little bit like more of the same, no variety, and wanting some variety. And that could be a place where it comes from. But I think that I have a very specific focus and passion in terms of the First Amendment and dissemination of information that keeps me in this sort of—like, I don't want to do employment work, I don't want to do class actions that are not related to my field. There are a lot of general commercial litigators who are fine with that, but it doesn't drive me to do anything. And so—and maybe you've identified where I am right now. I've got existing work, but sort of there's this prospect elsewhere that I think about but haven't really done much to engage in and get work in. And I think partly because at this stage, it's counseling, it's not litigation. Because I mean, it is litigation in some senses, but we're just at the beginning. And so there is probably a lot of counseling that's being done. I know there is counseling being done by my partners, for example. And the counselors are not always the litigators, and that's true in companies as well. It's odd to me because it seems to me that when you're building a product and you want to know the risks of litigation, a litigator at some point has to be involved because there are things that we see—we're used to reading something and turning it around and making it seem like it's something different. But obviously that can't be the rule in every product that's developed, and clients do consult litigators, of course, but it's a much smaller group of people than the people that are litigating these issues.

Khurram Naik: On that topic, how do you get—so you're talking about how people can get counseled and understand risks they don't understand—how do you do that on the scale of your team? How do you get new ideas from your team? Or can you point to matters you've worked on where someone that was on your team that you manage presented some view that was contrary to yours that you adopted? How do you get new ideas into your work?

Ambika Kumar: I don't know that there's ever been like an idea that I ultimately disagreed with. There have certainly been ideas that I'm skeptical of. There's also new arguments that I'm pleasantly surprised someone has come up with that I think are really good. I am a firm believer in "two heads is better than one." And so I do a lot of talking with my team about various issues, talking out loud or in messaging, what makes the most sense here. Because there are many calls in litigation that are not easy. And I tell my clients that too, "Look, this is not one I feel strongly about, here's what I think." Because they should be participating too. But clients also provide new ideas. They'll be like, "Well, maybe we should phrase it like this."

Usually if a team member disagrees with me strongly, they'll be able to persuade me or I'll be able to persuade them such that we're never really on a different page at the end. And that's because my team is awesome: they're smart, they're open to discussions of different viewpoints. Hopefully they've learned from me. I mean, I think the priority is to serve the client best and we understand what the client's goals are. There's room for disagreement in approach, but there's very little that—I mean, not always, but like there are certainly times where I'm like, "That is a dumb idea." But they're not usually coming from my team.

New ideas also come like when I do appellate arguments, I have moot arguments with outside counsel from other companies—other law firms, rather. So here I am doing a moot with my client for a circuit court and here are these other lawyers that are basically my competitors helping me prep in front of the client. And actually, a client suggested this to me once and now I'm just going to make it a practice if I can from a cost perspective. It's super helpful because you've been embroiled in this litigation and you know what you think, but you don't know what somebody fresh to the case thinks. And so you know, I don't often call my competitors and say, "What do you think of this?" but I wouldn't put it—it's not out of the realm of possibility on certain things. I often ask the general commercial litigators, "What do you think about this?" So you know, I'm always soliciting input, and I think that's one thing the team likes about me is that I like to vet these issues and not just sort of be like, "This is what we're going to do." And hopefully that gives them the ability to raise—whenever somebody's like, "I have a dumb question," I'm like, "Don't say it's dumb because you're not dumb and it's probably not dumb." Yes, there are dumb questions, but they're very few and far between. So I want you to raise them.

And I think particularly with women, they're not—we’re not taught to have as much confidence. That's my anecdotal experience. And so the chances that I'm going to hear "I have a dumb question" from a woman versus a man are much higher. It's not that men don't do it, they just don't do it as much. And so I will tell the women on my team, like, "Don't do that. You're smart." And people did that for me. I remember one of my mentors, who's probably one of the best trial lawyers in Seattle, once put in a review that I needed to be able to speak up more in front of clients because I had some value to add. And I want people to feel that way because if I'm working with them, it's because they do have some value to add. And I'm looking to squeeze out as much value as I can for the clients. Because my goal is to—oftentimes it's not to continue their litigation, it's to get them out of litigation in a way that's consistent with their goals. And so my goal is not—in some ways, it's self-defeating in the sense that law firms have historically prized billable hours. But my goal is to spend fewer hours on my cases and have my team spend few hours on my cases, just enough to do a really good job and get rid of it, whether it's through a motion to dismiss or summary judgment or through a settlement of some sort. I think that's where I get new ideas. Sometimes it happens in casual conversation with friends, they'll say something and it'll make me think.

Khurram Naik: On the topic of—you mentioned this mooting approach, and of course that's only when there's an argument to be made at that point in the case. Is there anything you're doing on any hygiene you have on a weekly or monthly basis with you or your team that you think differentiates you or makes you particularly skilled as a litigator?

Ambika Kumar: I'm not one for formalized processes. Just to give you an example, I had an assigned mentor and then I had other people in my life as a junior associate, and I cannot say my formal mentors were even close to being as helpful to me as the people I worked with closely. And I would say the same thing about probably like—I mean, would it be a good idea to have a weekly or monthly meeting? Probably. But the reality is I talk with these people all day every day. It's not as if like I go off to a deposition, I'm gone. My messaging app is closed, but I'm sure that somebody has messaged me about a case, more than one person.

And so one of my associates, actually it was a newer one, you're familiar with her, she said something like, "I like this, you're kind of like a millennial, like you'll hash these things out over messages." And I was like, "Well yeah, I think it's more efficient." And that is unusual probably for someone of my generation, but it's just how I work. And so my chats are full of debates about what we should say or we shouldn't say or is there a doctrine that says this or what do you think of this. And so my whole life, whether personal or professional, is a back-and-forth with other people. It's how I operate. I think it's probably what makes me a good litigator. I like to see different styles and ideas and pick the one I think is best. That gets harder over time because it's sort of like, "I know this and I'm not going to be swayed." But the nice thing is the law changes, so it doesn't have to be that like I was wrong, it can be the law's different now. So it's a little easier to accept and seriously consider a different idea.

Khurram Naik: So you're the co-chair of this practice. It was this hard-won process that in many ways was the very thing you were building toward when you first joined your firm. So what could top this? Like, what could be more gratifying than having achieved what you have? You've got high decades of career ahead of you if you want it. So what is it that's going to motivate you? Is there some sort of goal or something like that from here? Is it something substantive like arguing at the Supreme Court? What is it that's that North Star that is the next level for you, if that's how you think of it?

Ambika Kumar: That's one thing, is arguing at the Supreme Court. I would love to do that. But even just—I don't know, I think we talked about this—the last few years I've really felt my gender in my cases and it's almost like the more high profile of a case or important of a case, the more I feel it. And I don't know why that is. But I would love to not feel that way. That would be a goal. I don't know how to get there; I think it might be impossible. But one can dream. I applied to be a federal judge a few years ago and I would seriously consider that in the future. To me, it would be very gratifying. I think I'd be good at it, and I think I'd be fair and I think it would be meaningful to me in a completely different way than what I do now. Those are the things in my career.

A lot of my overall goals are more personal, like raising my kids to make it so that other women don't feel this way—I have two sons—to make it so that that's not a thing, although I think it will always be a thing. Or taking care of my parents or making the most of the time that I have, knowing that it's finite. But you know, in terms of career, I think arguing at the Supreme Court, getting more cases that are high profile where I'm the lead and sort of the presumptive authority on what we're going to do—because those positions are very hard to get and for a variety of reasons. But I think that I would feel good about that if that happened more often in my cases. And I can see it possibly moving in that trajectory, so it's not hopeless. I mean, I really enjoy mentoring and I would love to find a way to do that. I also think I'd be a good mediator, but I'd have to figure out "How do I become a mediator?" and that seems daunting. But those are the things that are exciting to me.

Khurram Naik: I think there are obvious things about becoming a federal judge that are appealing: the influence you have, the variety of matters you take on, that impact you have on society. What is underrated about becoming a federal judge?

Ambika Kumar: Underrated? I don't know. I mean, I think just the ability, especially in the area of criminal law, to have the ability to look at somebody standing in front of me, make an assessment about what's going to happen to them is very meaningful. I also—to be clear, there are definitely drawbacks. I interviewed a few judges when I did this before I applied, and it's clear to me that it is not the life for everybody. And particularly right now, I'm not sure. You know, if I were the judges that were holding unconstitutional executive orders, I don't know. I mean, it would be thrilling in some ways, but it would also be scary in some ways. Just like, you know, leaving the country and coming back as someone who's brown—yes, a citizen, but still brown—is also terrifying. So not terrifying, but it is worrisome, and the fact that I have to worry about it is terrifying. I think judges have the ability to help shape the profession in the sense that, you know, when I'm talking about women and men or younger lawyers, older lawyers—some judges have a rule that's like, "We want more junior lawyers to argue." I think there's a lot of authority and power in a judge, particularly a district court judge, who has more of an ability to affect the day-to-day life of the people that are clerking for them, that appear before them, whether client or not. But and by being an example, that hopefully deter stereotypes.

Khurram Naik: Well, I'm looking forward to your potential confirmation in the coming years.

Ambika Kumar: It's not going to happen, but that's okay. Maybe, maybe.

Khurram Naik: Ambika, this was exactly what I hoped it would be. It was such a great glimpse into your really unique career path, how you think. Yeah, I’m not going to use the "S" word, I've already said it too many times. But yeah, I just think it's very easy to talk to you and you have a lot to share that I think is very relevant for lawyers at any stage of their career. So I really appreciate your direct communication as you said. So I just appreciate how much you have to share here and hopefully we can do this again.

Ambika Kumar: Thanks, I appreciate it.

In this conversation, Manisha breaks down how she took a "bet on yourself" moment when she left partnership to run AG enforcement, the two simple process changes that accelerated investigations across her division, and how she now juggles 15-20 cases by delegating strategically and holding weekly team meetings where everyone—from summer associates to senior counsel—contributes ideas. She also explains why climbing 19,000-foot ice faces in Peru taught her more about trial prep than any courtroom experience could.

We discuss enforcement trends (climate disclosure, consumer finance, AI bias), the difference between federal and state AG cultures, how rock climbing's problem-solving mirrors litigation strategy, and why Manisha believes the sufferfest of training for a summit is the same mental game as pre-trial prep.

Keep reading below for the full link to the episode and the full transcript of our conversation.

Top Insights

Below are the highlights of our conversation:

• The "Bet on Yourself" Decision: Why leaving Quinn partnership to run the NY AG's Economic Justice Division was a career risk—setting enforcement priorities, overseeing 250 people, managing six diverse bureaus—and how Manisha turned that government experience into a thriving state AG defense and plaintiff-side practice when she returned to private practice.
• Two Process Tweaks That Changed Everything: How Manisha accelerated investigations across the AG's office with two simple changes: aggressive subpoena follow-up every two weeks (no more black holes) and eliminating endless confidentiality agreement negotiations by using a standard form—because as a plaintiff's lawyer, "justice delayed is justice denied."
• Strategic Delegation at Scale: Managing 15-20 cases simultaneously requires brutal prioritization—Manisha delegates anything "urgent but not important," holds weekly team meetings where everyone from summer associates to partners contributes, and uses the "important/urgent" matrix to protect time for high-ROI work like business development (roughly 30 hours/month).
• Mountaineering as Litigation Training: Why summiting Alpamayo in Peru—seven pitches of ice climbing at 19,000 feet, headlamp knocked out by falling ice at the crux—taught Manisha that the sufferfest of pre-trial prep is worth it for the summit moment, and how training in brutal conditions (night climbs, snowstorms, cold) prepares you to stay calm when things go sideways in court.

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Full Transcript

Khurram Naik: This is Khurram with Khurram's Quorum. My guest today is Manisha Sheth. Manisha's path to partnership at Quinn seemed inevitable: she clerked, she was a federal prosecutor, but then she made a decision to return to government practice for New York, which transformed her practice. Here's Manisha.

Khurram Naik: Manisha, I'm really glad to have you here. I'm excited to jump in and talk about your career. You’ve got a number of interesting jumping-off points in your career, and so it’ll be excited to talk about your movement from private practice to public, and then back to private, and back to public, and then back to private. It’s less common to do that, so I think that’s interesting and remarkable and so we’ll spend some time on it. But I want to start with early in your career because I observed that you graduated law school, you clerked, you were an associate at a strong White Shoe firm, and then you went to the US Attorney's Office. And so from prior conversations, you said, you know, starting in law school you knew you wanted to go to the US Attorney's Office. And so it seems like up until that point in your career, everything was very tracked and you kind of knew where you were heading and you were able to achieve the outcomes that you wanted and do the kind of work you wanted. And then in returning to private practice in 2008, at the inception of the Great Financial Crisis, you joined Quinn in New York City in the middle of this financial crisis. Tell me about how this was maybe a divergence from the plan you set out even just from your law school at the beginning of your legal career.

Manisha Sheth: Yeah, well thank you for interviewing me. Great to be here. What I would say is when I was at the US Attorney's Office, I was in the government and healthcare fraud unit. So although those were not the exclusive cases I worked on, I definitely had a specialization or a focus on cases involving healthcare fraud issues. So I did a ton of cases against actual healthcare practitioners, whether they were physicians or social workers, but somebody who was allegedly misbilling or upcoding or defrauding really the government with regard to Medicare or Medicaid.

And when I decided to return to private practice, I enjoyed those cases. I come from a family of physicians and so I really love the science and the medicine aspect of those cases. And I thought when I returned to private practice, I'd like to continue working on those cases, whether it be False Claims Act prosecutions or defense cases or off-label cases, but I definitely wanted to continue in that industry.

But when I came to Quinn, I started in Quinn in August of 2008 and it was literally, you know, maybe weeks before kind of the meltdown in the financial crisis of 2008. And so when I came to Quinn, I was immediately staffed on a large matter involving a monoline bond insurer who had provided financial guarantee insurance to various institutional investors on residential mortgage-backed securities. And those securities were issued by Bank of America and they were based on loans that were underwritten by Countrywide Home Loans and then the underwriter was Countrywide Securities.

And so that was one of the very first RMBS cases during the financial crisis and it started—it was actually a put-back case. So basically the monoline bond insurer was taking individual loans that were part of a pool of loans in a securitization and putting them back to the issuer to repurchase those loans. And the claim was that those loans were not underwritten in accordance with the underwriting guidelines that were part of the representations and warranties that the bond insurer relied on to purchase those loans—to purchase those notes.

And we put together that case. It was completely new in terms of a sort of subject matter. I did not know anything about structured finance, certainly did not know anything about residential mortgage-backed securitizations. But I think as any litigator will tell you, that's what we do. We come in, we learn an industry, we learn a subject matter, we really kind of become experts in that area and then we use that expertise to litigate the case. So that's kind of how my career in the structured finance practice area started.

Khurram Naik: And what was it like to be heading down this path where you had some fairly definite views of what you wanted to do, the credentials and skills to do that, and finding yourself having to switch gears? And as you say, litigators, you know, they're versatile and capable of jumping into different subject matters and drilling into what's the core levers or turning points in it. But you still had a conception of what you were doing and then you had to change gears. Was that easy for you?

Manisha Sheth: Yeah, honestly, it was easy because of everything that was happening in the markets. My first two months at Quinn, I literally was working every night till like 2 or 3 in the morning and I remember thinking, "Did I make a bad decision to come to this law firm where this is how it's going to be for the next however many years?" because obviously that's not sustainable. But you know, I realized as time went on that that was just a very unique time in our history. That was the 2008 financial crisis and then there was a lot of things that were happening. There was a case I got staffed on that involved AIG; there were some matters involving Lehman. So like now looking back on it and you see everything that happened, it completely makes sense why we were busy working 24/7 during those initial years. And then of course it kind of eased up after a couple of years, but it was definitely pretty intense when I first joined Quinn. So to answer your question, there really wasn't much time for reflection because we were working 24/7—or felt like we were working 24/7.

Khurram Naik: And then to your point on that, you know, when you're working so much, can you really even take a moment to say, "Hey, this is something crazy, this is probably a super unique moment"? You probably just don't even have the time to think that.

Manisha Sheth: No, not at all. I'm not even sure when I actually realized that, but it wouldn't surprise me if it was maybe a year later.

Khurram Naik: Well, I guess that's interesting because I think any number of lawyers might find themselves in that place. Definitely a lot of lawyers that I work with that are elite litigators are just working so much and necessarily just means you can't slow down and think about your career. And the thing is that the quality of work these lawyers have is very high. They're getting standout experience, briefing, they're doing really high-quality work. How do you assess whether you're going down the right path? Is it enough to be busy and just trust that "Hey, I'm getting great skills," or is there something to be said for some place for strategy or contemplation about "Hey, where is my career going?" Were there any moments like that in your career?

Manisha Sheth: Yeah, absolutely. I mean, my advice to young lawyers would be you absolutely should be thinking about that because it is not sufficient and or advisable just to focus on hours, billable hours. You don't want to just say, "Oh, I build whatever, 2400 hours this year, 2800," whatever. That's—it's important to be busy, but I think you need to have your eye on the bigger picture. And what I mean by that is: are you acquiring the necessary skill set to be a well-rounded litigator or well-rounded trial lawyer at our firm?

When I came to Quinn, when I joined the firm in 2008, I had already, I think, ticked off many of those boxes in terms of skill set. So I knew how to research, knew how to do legal writing, I had already tried over a dozen cases as a first-chair trial lawyer. So I felt like I'd already checked off kind of the skill set boxes. And what I was brought on as was of counsel with a, I think it was a two or three-year look-see, so they would assess my performance at the firm to decide whether or not I made partner when they put me up for partner.

And so for me, you know, it wasn't so much about acquiring the right skill set. But what I would say for somebody else maybe who's within a firm, I would just say look, make sure you're acquiring all these skills. So that you're not just staying busy, but are you getting deposition experience? Are you taking depositions? Are you defending depositions? Are you arguing motions in court? Like you want to make sure you have enough experience in all of those buckets so that if and when you're up for partner you can—or even if you're not up for partner, you just want to be able to say, "I know how to do all of these skill sets." I had gotten a lot of that experience as a prosecutor. Probably not the deposition experience actually; as a prosecutor, there's no discovery in a criminal case. So even though I'd taken a ton of witnesses at trial, done direct examinations and cross-examinations, I didn't have that many depositions under my belt. So that would be one area where, once I came to Quinn, I got a ton of that experience because now I was doing mostly civil practice.

And then the other thing is managing teams. So at the US Attorney's Office, it was generally just myself. If it's a huge case or a high-profile case, maybe there's another prosecutor and a case agent. So the team is really just three people at most. And then coming to Quinn, you know, the case I was telling you about for the monoline bond insurer, that team was gosh, 15 to 20 people. And so I was running that case team, and that's a whole another skill set: is running that case team, making sure—we were plaintiffs—so making sure the case—not only do we investigate it before we file the complaint, but once the complaint is filed, making sure that we are aggressively moving that case forward. And everybody on the team knows the strategy, is coming up with the strategy, and taking affirmative steps so that the case doesn't languish.

Because I truly believe that justice delayed is justice denied, especially when you're a plaintiff. You've got to get to a resolution because every passing day, the client is incurring more and more expenses of litigation, whether that's in discovery or motion practice or what have you. But you need to move your cases forward. And that means like keeping on top of the other side in terms of discovery. You want to make sure are they producing the relevant documents, are they slow-rolling documents, and if they are, what do you need to do to get those documents? Maybe you need to make a motion to compel. In that case, I think we must have made 8 to 10 motions to compel to actually get all the key evidence for trial.

So, I think you definitely want to keep an eye on the progress of your career. Part one of that is making sure you have the right tools in your toolkit and you're checking all the boxes in terms of a skill set. But then part two, and this I think happens as you get more and more senior, is you want to develop those practice areas. Because all of us really are generalists here at Quinn. We're all trial lawyers. But it definitely helps in terms of business development to have three or four practice areas where, you know, those are your core practice areas. So for me, I now do a lot of healthcare litigation, whether that is representing clients adverse to the government in a civil regulatory investigation such as a False Claims Act case, it could be an antitrust matter, it could be a securities case. So like having a few practice areas where you really know those practice areas and have kind of specializations or sub-specializations in addition to being a general litigator and trial lawyer.

Khurram Naik: At what point—you mentioned this concept of being a well-rounded litigator—at what point in your career did you first feel "I am a well-rounded litigator"?

Manisha Sheth: That's a good question. I mean, I think it would probably be maybe sometime during my first stint at Quinn, so between '08 and 2016. A large chunk of my practice was plaintiff-side at that point. So I would say 90% of the cases I worked on were plaintiff-side litigation. Again, a huge chunk of it was in the financial crisis litigation, so involving RMBS cases. But I did have other matters as well. But when I say well-rounded litigator, I really just mean having the skill set of knowing how to put a case together if you're on the plaintiff's side and then knowing how to litigate it from soup to nuts. So that means knowing what the end game looks like to the extent it's a trial and then working backwards from the trial outcome to knowing what do I need to get in discovery to be able to prove my case at trial. And I think once you know that soup-to-nuts process, I think at that point you are a well-rounded litigator and you can do any kind of case. The practice area or the subject matter really doesn't matter because you have the skill set and the tools to put a case together and then litigate it and then litigate it through trial if necessary.

Khurram Naik: Do you feel like you got that sense of being a well-rounded litigator before or after you became partner?

Manisha Sheth: I don't know if it's so binary. I think it's an evolution. So, and I guess to give you an example of that, during my first stint at Quinn, I might have had, I'm guessing here, but like maybe five cases that I would be handling at any given moment in time. And on all those cases, whether it's five or seven, I was the person kind of running the day-to-day on the case and was very well immersed in both the facts and the law.

And then, I think as you get more and more senior, and I think I developed this next skill set when I went to the New York Attorney General's Office—you get to a point where you can handle, I think like now I might have I don't know 15 to 20 cases on my docket, and I'm probably—I am involved in the day-to-day, but not with the same level of granularity as I was in the beginning years as a partner. And so now the skill set is much more like a strategic sort of skill set. Like what are the big decision points in the case and kind of informing the overall strategy, not only for the big picture case but sometimes kind of on individual sub-avenues.

And I think that's a skill set that I really developed when I was at the New York Attorney General's Office. Because there I had, I think it was roughly 250 people in the Economic Justice Division reporting up to me and oversaw six affirmative litigation bureaus in different practice areas. So like there was an antitrust bureau, there was a securities bureau called the Investor Protection Bureau, there was a Consumer Frauds Bureau. So very different subject matters. Each bureau, I mean, it ranged, but you know, could have had hundreds of cases and investigations and I had to oversee all of it.

And so my level of involvement varied. If it's a big case, if it's a high-profile case, I was much more involved than if it was an inquiry or the beginning stages of an investigation. But any investigation that got opened, I had to approve. Any subpoena that went out—opening subpoena that went out the door—I had to approve. Any settlement, I had to approve. Any complaint, any decision to go to trial versus settle the case, I was involved in the approval process. And you know, being responsible for those critical decision points forces you to—you don't have to know kind of all the minutiae of the case, but you do have to know what are the right questions to ask so that you can make those big picture strategy calls. And I don't think that was a skill set I had when I was sort of a young partner at Quinn handling maybe five cases. But then when I went to the AG's office and had a way bigger docket, I had to develop that skill set. Which was, you know, challenging in the beginning, but now I definitely rely on that skill set when I've returned to Quinn and as a result, am able to handle, you know, a much bigger docket than when I was a junior partner.

Khurram Naik: So let's talk about what it looked like to be handling/overseeing as a strategic counselor on 15 or 20 cases. What is that daily cadence like? How do you stay organized and how you—15 to 20 is a lot. And so each of these, as you say, these are—it's not like it's 15 to 20 securities fraud cases. You’ve got a wide variety of matters, probably just totally different fact patterns and postures, different stages of cases, so it’s not like "Hey, I'm just in fact discovery on all these cases so my mind is all about fact discovery." So different causes of action, facts, stages of the case, maybe the clientele have other constraints that are commercial or that impact how they're thinking of legal decisions. So I think in the most tangible sense, how do you keep track of all that? And then how do you, you know—I’m picturing maybe on a daily basis you've got a heads-up on these cases and on a daily basis you're saying to yourself, "What do I need to do to move any of these cases forward?" but that's just my conception of what you're doing in that position. So I'm really interested in hearing how you do this.

Manisha Sheth: Well look, the first thing I would say is I’ve got to have great case teams. Right? Nothing I don't think any of us operate in a vacuum. We have case teams on all of our cases. So I'm only as good as my case team. And so it's important to me that I have a very strong case team put together for every case. And that doesn't mean staffing every case with the same people because I do try to pick the lawyers, whether that's the junior partner or the associate, like pick the folks who have the experience that is best suited for that particular case. So I think that's the first thing.

I mean, how do I keep track of them all? It’s a good question. I don't know that I have like a spreadsheet or anything. I think, I mean look, one thing I do is have weekly team meetings. So a regular—it may not be weekly, it could be bi-weekly depending on the case—but I think it's important to keeping a case moving forward and making sure no balls get dropped and things are getting done to have that weekly team meeting. I also think it's important because it gets the team invested in the case, right? They feel like they're part of a team. I also like it because I get the benefit of everybody's thinking. So when I have a case team meeting, it's everybody on the team, from if we have a summer associate, the summer associate's on the team, if we have a paralegal, the paralegal's on the meeting. So I want to make sure every single person on the team is part of the team, feels like they're part of the team, and feels empowered to contribute ideas to the team. Because look, the cases we get, or the cases we get hired by clients for, are not necessarily easy cases, right? They're not going to be going to Quinn Emanuel for something that's sort of a black-and-white or open-and-shut case. They're usually cases that are bet-the-company litigations or where there's a thorny legal issue or where there's a business issue that they need to try and resolve within the parameters of the law. And so it's important to kind of get the benefit of everybody's creative thinking on it. And oftentimes you'll have someone who's like new to the practice of law, they might think of something that, you know, somebody who's been practicing for 20 or 30 years hasn't really thought of. So I think that's one way to keep track of what's going on on the cases and making sure they move forward expeditiously and with the benefit of everybody's thinking.

I mean, the other thing—this is maybe too much in the weeds—but I think just by virtue of keeping our time records. Like we all obviously lawyers have to keep records of their time in six-minute intervals. And so when you're keeping track of your time in that way and then you enter your time, it's sometimes a reminder of like the status of each of those cases. Right? So you can see as you're putting in your time, you realize "Oh, I have to also do this." I also have a very extensive to-do list that I kind of keep every week, like what I want to get done for the week and then also every day. And sometimes the challenge is finding time to keep things moving in between or after all the day's calls and meetings. Right? Because the day really easily gets booked up with calls and meetings and sometimes the only time you have to really kind of do the deep work is in the evenings or early mornings and in the weekends.

And the other thing that I think I've learned maybe after the AG's office really—or maybe during my time at the AG's office—is this concept of delegation. Right? Like what makes sense for me to do versus for me to delegate to somebody else to do and then review it. And so I think it's important, in order to be able to handle all these cases and to keep them moving, I think it is important to delegate. And I think that's a skill set that I've learned at the AG's office—or refined, I should say, more so at the AG's office—because I think when I was a junior partner, a lot of it I was doing myself, whereas now I'll delegate it and then look at it after I get maybe the first or second draft.

Khurram Naik: So a couple of things I’d like to pick up on. You mentioned this idea of having a whole case team that's invested in and everyone's contributing. And so I've seen that, you know, when in my small recruiting agency it was just me at first and then my wife is now my partner, she joined, and then we have someone who's leading operations so it's the three of us. And so I had systems in place and processes and, but so it's evolved over time. At this point, I don't think there's anything I can point to in the agency—there's very little I can point to at the agency that isn't some set of ideas as built by multiple people. It's not attributable to any one person. You can you can directly point to: well, you had this idea and then you riffed on that and then I did this and so then it's like this cycle of ideas. And so it's pretty amazing to see that, to start to see this. I've never seen a team coalesce in that way because at a law firm of course it's it's pretty hierarchical typically. So a question for you is: you mentioned this idea of having these teams where people are new to it and then able to add ideas and perspectives that you don't see if you're just kind of patterned in what you're looking for. Is there anything specific you can point to in in your cases that, you know, a time when someone who was closest to some aspect of the case surfaced an insight or perspective that changed your mind?

Manisha Sheth: I mean I think there's probably countless examples of that. And but I wouldn't say "changed my mind." I kind of view it as more of sort of a brainstorming exercise. So the way I kind of think of it is is problem solving. So, here's a problem and all of us are trying to collectively or individually solve that problem. And then just hearing different people's perspectives and insights on how to go about solving that problem.

And sometimes it's not just one person as you say, but sometimes it is. Right? Like so, you know, we were doing a lot of these RMBS cases as put-back cases, so meaning it was a breach of contract. And at some point in time when we did the RMBS cases for the Federal Housing Finance Agency, and that was our biggest RMBS representation, we represented the FHFA, the Federal Housing Finance Agency, who was the conservator for Fannie Mae and Freddie Mac, and we sued every bank on Wall Street all on the same day because we had a statute issue. And in that case, we changed the theory. Right? Like we brainstormed and we came up with the Securities Law violation as opposed to a breach of contract violation. But that was a change. Like we had historically looked at it as a breach of contract claim and then through a lot of brainstorming and discussions, we came up with the Securities Law violation under Section 11 and 12, which made it much easier from a—sort of the elements and burden of proof standard. So those cases were much easier to plead and then eventually prevail on.

Khurram Naik: And then you mentioned this concept of delegation and at the scale that you've operated at, both at the AG's office and now with these larger teams you're running, you couldn't run these cases without delegation. But I think I think it'd be helpful to to dig a little more into delegation and, you know, maybe one lens on it was: what was hard about that at first? What was hard about delegating? And then over time, what are the principles you use for delegation to empower people maximally without looking over their shoulder but then also having coherence and alignment? Like tell me some more about because I think delegation is a concept that people gloss over pretty easily and just say, "Oh sure, just delegate," but like there's major challenges with delegating, particularly if you've been trained as: my work product is really what the clients are looking for and this is how I show that I'm adding value to a case. How did you switch to that mindset? What was hard about that initially? And then it’d be interesting to unpack some more about practically speaking how you delegate.

Manisha’s experience moving between government and private practice resonates with Rakesh Kilaru, who went from appellate law to the Obama White House and then to a litigation boutique.

Manisha Sheth: Yeah. So what is hard about it, I think maybe it's a view that you don't want to push your work off on other people, right? So I think that I think was the hurdle to come over. Like if you're looking at it from that mindset, it becomes very hard to delegate because I certainly don't want to do that. But if you change the mindset and you think of it as I'm delegating the task, but because our rate structure, right—so it doesn't—it's not in the client's best interest for me to cite check a brief as an example, right? It's probably not in the client's best interest for me to do the legal research or even do the first draft of a brief.

And what I think I struggled with in the beginning was one: coming over that mindset, but two: getting work product, let's say a first draft of a brief, and I would get it and I would not be happy with it. And then I felt like I had to rewrite it. So I was kind of torn between: well, should I just do the writing myself or should I try to edit this, which in some ways might be a total rewrite? And what I've learned I think through that process is it's important to give folks guidance at the get-go. So don't wait to get the draft and then say, "Okay, we'll rewrite it and restructure it." So oftentimes what I'll do is have a call with the team and say, "Here's what I envision this looking like," or sometimes I will do an outline or ask them to do an outline and say, "Let's discuss the outline and then let's draft it." So I think just giving that initial guidance or feedback before the delegation is important to avoiding a situation where you get work product that's not quite what you wanted and then you don't have enough time to turn it around. And that's the other important thing is I think you need to build in, if you're going to delegate, you need to build in enough time on the front end so that you do have time to rework it if needed.

And then on empowering people, I think what's important to remember is that people want to do good work, right? Like I and I've definitely seen this. People who come to our firm or I think any of the top White Shoe firms, they're motivated. They probably did well in law school, right? That's how they got here. And when they get here, they want to do good work. And sometimes it's trying to tell them or teach them how to go about doing good work, right? And so I think the feedback is important both on the front end but also on the back end and not waiting, right, till the end of the year or for the annual review process to give that feedback. So I think it's important to give real-time feedback when you get work product. So I just as an example, I had some—I had one of my teams put together a witness interview outline for an interview that happened today. And you know, it was a good interview outline, but a lot of it was open—not open-ended, it was leading questions. So a lot of "did you do this?", "did you do that?", a lot of "yes/no" answers, right, in this outline. And so one of the immediate feedback items I gave to them was: "Look, next time you do this, try to ask a lot more open-ended questions because we want to hear the story from the witness now. We don't want to just hear yes and no. And so in the future, try to have a lot more open-ended questions." So small point, like they covered all the topics, but the way they framed the questions was was a bit too narrow, right? And we might miss something if we ask a question in that way versus if we ask it in an open-ended way.

So little things like that. And then in terms of how do I decide what to delegate versus do myself, I think the rate is an important question, right? Like I just am cognizant of what makes sense for the client in terms of the rate structure. And the other thing I think is just urgency and keeping the ball moving at all times. So often times I am tied up in a call or meeting and I don't want the case or that particular project to just sit there while I'm tied up. So I just want to make sure that on all my matters, some ball is moving actively across all of them if I am tied up on a meeting. So that when I'm done with the meeting, I can turn to the work product or whatever the deliverable is and then focus my time on it. So I think it's part of it is just timing and I think that's best accomplished with communication. So sometimes I'll tell the team, "I'm not going to be able to look at this until whatever Saturday morning, and so you know, just give me the best work product you can" because I don't want people to like rush and try to get me something on Thursday if I can't look at it till Friday. So just kind of keeping everybody—keeping the lines of communication open on timing so that they have the time they need to get it done and do it in a way that, you know, they feel good about, and at the same time the thing's not sitting there on somebody's desk just waiting to be reviewed.

Khurram Naik: And part of what you're talking about with delegation is having an understanding of the opportunity cost of your time and what's the highest and best use of your time. And so I'm sure that's evolved over time. So I think there's probably a tension between the things that have to get done today, which is in some sense the highest and best use of your time—like, "Hey, the client wants me to talk to them today"—so that is something I need to do. But then there's probably other activities that are even higher leverage prospectively, you know, in the future, that will have just—there's probably something that you can invest in today that will have a bigger payoff. You know, an obvious thing is something like business development—that’s an obvious application of your time that has a compoundingly beneficial outcome. How do you think about what is the highest and best use of your time?

Manisha Sheth: Yeah, great question. Because there is a tension sometimes between what is important and what is urgent. And I think you just have to be careful of—sometimes the things that are—I forgot the name of this matrix, but there is a sort of a rectangular matrix, a four-grid matrix where I think it's urgent and important. And so if something is urgent but not important, that's usually something I can delegate. If it's important and urgent, I may still delegate it, but I do have to make time or set aside some time to review it before it goes out the door. I generally don't let anything go out the door, meaning out to a client or to a court, without my eyes on it.

And then there's stuff that's not urgent but very important like business development. And for those, it's so easy for that stuff to just get left behind, right? Like that's the stuff that you easily could never get to. But I think I've been doing a lot better with that certainly this year in terms of making time for it because it's one of those things that when you talk about sort of the highest and best use of your time, like there's certain things that only that I'm going to be able to do. And I don't mean like business development generally, but like business development for a case involving the New York Attorney General, right? That's something that is within my specialty and so I am going to have to do that. And so oftentimes, you know, we monitor the docket, we see what cases the AG has filed, what the AG has said in terms of a press release or an enforcement priority and, you know, really those are kind of urgent business development because if a case just got filed, I want to make sure I reach out to the entity who just got sued and tell them here's how we can help you. So there are some things that fall into urgent business development and then some things that are more long-term. But I think the important thing is to make time for that because I the business development is like the prime example which is that's something that I do need to be spending my time on, but it may not always be, you know, urgent.

And I try to set aside like—it’s hard to say, I mean I would probably estimate that in 2025 I've probably spent maybe like 30 hours a month on business development. Some of that is just general outreach, but frankly, a lot of it has been substantive, case-specific pitches.

Khurram Naik: Do you have an aspiration for how much of your time you want to allocate to that—highest and best use time that is?

Manisha Sheth: Yeah, I think the 30 hours is probably a good benchmark. I can't say that I've been—like I don't have a rule where I say, "Okay, every day I'm going to spend two hours on business development." But what I have done recently is say, "Okay, well once a week I want to take a client or potential client out to lunch or dinner." I also want to, you know, make sure that I'm making some kind of post on LinkedIn maybe once a week. And then the thing that kind of throws a wrinkle in things sometimes is these substantive case pitches because they do take a lot of time to prepare for. But I think they have a high ROI, right? Because if if you do a substantive case pitch and you are showing the potential client that you have a real value add and you can help them with a particular matter, I think that's, you know, kind of an immediate ROI as opposed to just sort of the more general being front of mind, top of mind for people. Right? Because I think that's the challenge with business development for a litigator is usually by the time somebody is sued or investigated, they already have retained counsel. And so you want to be top of mind for someone when they have a business dispute or when they have a regulatory issue. And really the only way to do that is I think to just kind of keep these relationships, you know, well-nourished and ongoing.

Khurram Naik: So, it's something that we've referenced a few times now, but I'm really interested in going back to the decision to leave Quinn for the New York AG's office. You already had a stint as a prosecutor, you grabbed the brass ring, you're already partner at Quinn. What could possibly induce you from doing the work that you really enjoy doing and you're getting resonance with to leave that to go back to public service? And you already did your public service stint. What were you doing that for?

Manisha Sheth: Yeah, I had the same exact reaction when I was approached by actually one of my former partners and they said at the time it was Attorney General Schneiderman, Eric Schneiderman, and he was looking for somebody to head up his Economic Justice Division. And they told me about this and I was like, "Uh, you know, first I had a bias, right? I was biased in favor of the Feds versus the state." And I was like, "A: I've already been a prosecutor, and B: I already did it for the Feds, why would I want to go to the state?" And it's also a huge financial change, right? So I was very—I wasn't thrilled with the opportunity and I kind of poo-pooed it.

And they said, "Well look, just talk to his number two." And so I ended up having coffee—this was early 2016 I think—with Janet Sabel, who was the number two to Eric Schneiderman at the time. And I talked with her and was convinced like immediately that this was a dream job. And the reason it was a dream job was because I would be setting enforcement priorities for the division. And the division was broad, right? So like there's Antitrust, there's Securities, Consumer Frauds, Internet and Technology—so data privacy, data security, that was another bureau. Government Frauds—that one actually was added to the mix afterwards—and then Real Estate, so condos and co-ops and real estate fraud.

So it was a huge mix of cases and the way it was described to me was you can look at what are the problems that are facing New Yorkers, right, across the state, not just in New York City, and you can come up with solutions through litigation or through investigations and you really can have the opportunity to change practices across various industries and make life better for New Yorkers. And frankly, that sounded really appealing to me. It also was appealing to go from—because when I was a federal prosecutor, I was the line assistant, so really didn't have the ability to set enforcement priorities; I was just doing my day-to-day cases. And this would be kind of a much bigger kind of macro role and overseeing kind of a huge group of people, right? I had at most I had overseen 20 people on a case team—the FHFA cases were pretty big, so those were big case teams—but never had overseen a division of 250 attorneys, staff, paralegals, etc. And so I thought that was another opportunity that, you know, I wasn't going to get at the firm. That's something that, you know, I didn't have in my future if I stayed at the firm; it would just be continuing to oversee case teams, which are going to be much smaller. So I think those were the two factors that really led me to say, "Okay, I'm going to go do this."

And then look, it also was—the thing I was worried about—like it obviously was a great job opportunity, but the one thing I was worried about is like well if I do this, am I going to derail my career? Will I be able to return to the firm—if not Quinn, another firm? Will I still be able to kind of transition back to the private sector? And, you know, so I had to get myself comfortable that that was an option. And I think, I think it was John Quinn who maybe said it or—I think it was John Quinn—who said, "Look, really what you're doing here is taking a bet on yourself, right? Like are you going to be able to leverage this experience at the AG's office and use it to develop an AG practice when you return to—if you return to Quinn or if you return to any other private law firm?" And so it's really just taking a bet on yourself. And I think in some ways that's risky, right? But in other ways, I think it was a great opportunity and it's actually panned out. Because since I've returned to Quinn, I feel that I have been able to use that experience to develop and further grow our state attorney general practice. Because we definitely had primarily a federal white-collar practice and a federal regulatory practice and we didn't have too many matters with state regulators including the state AGs. And now that has really taken off, so that's been—that's been really rewarding.

Khurram Naik: So heading into this, between yourself, John Quinn, any other peers at your firm, did you have any thoughts prospectively for what an AG practice would look like? You know, if you were to come back to Quinn, what an AG practice would look like? So did you have any thoughts at that time? Because I'm sure you had some sense of what that would look like, right? Just some sense of picturing what would be the value of the skill set to return to private practice and then having returned to private practice, how did those ideas differ from when you actually had the experience?

Manisha Sheth: Yeah. So what I thought it would look like would be partnering with the AGs' offices. Sometimes, and New York rarely does this, but some AGs' offices will hire outside counsel on a huge matter or a matter that's going to trial. And to me, that sounded most appealing because I really do like being on the plaintiff's side of the V. And then when I came back to Quinn, I did try to develop that part of the practice—the plaintiff's side working with AGs—but that has not taken off as much as the defense side practice. So most of my matters have been adverse to the AG's office where they're investigating a client or have brought an enforcement proceeding against a client. And that's more of, you know, what one would expect, I think. The other side of partnering with the AG's office is more unusual. It does happen from time to time, but it doesn't happen with New York if at all—I don't even—I can't think of a single case where it has happened with New York; it's usually other state AGs that do that.

But the other thing that has been good is even if the AG does not hire us, I have assisted clients who are facing an issue to go into the AG's office and alert the AG's office to an issue that they're facing. So almost like facilitating that interaction where a client is bringing a problem to the AG's attention. Usually, these are antitrust matters or—they don't have to be—but like usually there's an issue with a competitor doing some improper practice or or just someone else in the industry who's doing something that's harming consumers and the entity or the client may not want to take that on directly but may want somebody to do something about it. And so it's nice having that "in" and that credibility with the AG's office to go in and alert them to the problem so they can decide what they want to do about it.

Khurram Naik: So then going back to the decision to go to the AG's office, so you realize, "Hey, it's really novel to be able to set enforcement priorities for these different teams, divisions." So heading into that, how did you develop a point of view on what enforcement priorities to set? Like just from the get-go you're sizing up what are these teams working on and what should they be working on? How did you come to a decision around that?

Manisha Sheth: Yeah, I think the first thing I did was talk to the bureau chiefs. So, well first I had to hire a couple of bureau chiefs. I had when I first joined I had five affirmative litigation bureaus. I think after maybe a year or maybe a year and a half they also gave me the Taxpayer Protection Bureau, which is the government fraud bureau. And so I met with each of the bureau chiefs, got a sense of what was currently in their portfolio, and then what they saw as the enforcement priorities—like what were they seeing in terms of what issues were impacting New Yorkers and what did they want to focus on?

And then in addition—so that was kind of the substantive areas—and then I had my own ideas based on what I saw when I was in private practice and what I would see in the newspaper, frankly, right? Like things we read in the paper also shed light on what issues people are facing. And then the other so that's the subject matter part of it, but then in addition, kind of seeing where there were process shortcomings in the office. So getting a sense of like where the different cases were in each bureau, why some of them appeared to have stalled as opposed to being moved forward, and getting a sense of like where things were falling down in terms of process.

And one of the things I saw was that there wasn't a lot of follow-up or enforcement of subpoenas, right? And when you're a regulator, one of your most powerful tools is a subpoena. Right? You can ask for documents, you can take testimony, you have the ability to actually get evidence and investigate before bringing a complaint, unlike in private practice. And I saw that people were not taking the subpoenas seriously from the AG's office. And so that was one of the first things that I focused on when I got to the office is making sure that people—the line assistants, the assistant attorneys general—were like following up on a subpoena. Like not issuing a subpoena and then having it go into a black hole, but like every two weeks following up to say, "Where are the documents?"

And then the second thing that was a process change was there was a lot of subpoenas that got stalled because people were negotiating endlessly confidentiality agreements. And so the other thing that I did when I got to the office was say we're not doing this anymore. Like we may in certain instances determine that a confidential agreement is appropriate and we'll have a form and that's the form we're going to use, and in most instances, you're just going to cover it in the cover letter to the production and we're not going to get into extensive negotiations about a confidentiality agreement because it was just slowing down the investigations.

So I think that was kind of my first priority in terms of moving the investigations forward and also making sure that the bureau chiefs were moving—were checking in with the line assistants in their bureaus to make sure that the cases were moving forward. And I think I got a lot of that experience from being on the plaintiff's side when I was at Quinn. Like if you don't move your case—if the plaintiff's counsel doesn't move the case forward, it's not going to go anywhere because defense counsel generally like to just slow-roll the discovery, have a lot of motion practice, and it's all about delay. And so I think you've got to be aggressive if you're a plaintiff's lawyer or if you're on the government side to just keep moving things forward and following up with people.

Khurram Naik: You know, it seems to me those two changes you highlighted about enforcing subpoenas and streamlining confidentiality agreements—these seem to be very process-oriented. Does that resonate for you?

Manisha Sheth: Yeah.

Khurram Naik: And so I think that’s probably not a concept a lot of litigators would think of themselves as "Oh, I'm a process person." You know, it's like "Oh, just the process is the rules of civil procedure and what they are and you navigate that," but you are here to handle a substantive issue at a time—that's the bottleneck. So is that a skill set that you're using today on these—you know, you've got a wide—you’ve got 15-25 cases and are there patterns you're looking for across cases to say "Is there some process I can put into place across these cases that would improve them, similar to how you did it at the AG?"

Managing 250 people and six litigation bureaus at the AG’s office is a kind of caseload management that Judge Vince Chhabria also practices from the bench — his MemDispo system processes 95% of rulings in short form, keeping an entire district court docket moving efficiently.

Manisha Sheth: No, not so much. I think—I mean the only thing I can think of is the team meetings, right? Maybe setting up a distribution list, setting up an organized S-drive of our documents. But I think all these are really firm-wide processes that are for the most part already in place. So I don't think I'm coming up with anything new in terms of process. I think it's much more substantive and case-specific in the cases I'm doing now for Quinn.

Khurram Naik: Going back to something you referenced earlier—talking about reviewing settlements at the AG's office and making decisions around them and thinking through "Is this good enough?" and I'm curious about: what was the criteria you're using for saying "Is this an effective outcome?" because you know—who's looking over your shoulder to say this is good or not? It's not like you—I mean things like returning dollars to the state, I guess that's a quantifiable measure—that's good—but that's only one kind of harm that you're looking to rectify or or remedy you're seeking. How do you come up with criteria to say "This is a good outcome"?

Manisha Sheth: Right. So I think any settlement that we did at the AG's office had three components. First, there's a monetary component, and sometimes it's a zero-dollar settlement, but there is some thought given to the monetary component. Second, and probably most importantly, is the conduct-based relief component. So what are the changes in conduct that are going to happen as a result of the settlement? And then lastly, admissions. And this I felt very strongly about and got a lot of pushback on this: will—is the defendant or target required to make admissions as part of the settlement agreement?

And you know, there were—and the three go hand-in-hand. Like I definitely view them as a package, right? So if you are willing to pay—if you are willing to do more in terms of conduct, maybe we will be willing—we as the AG's office—might have been willing to take a little less in terms of money, because those conduct-based improvements come with a cost—they're not for free. There's some cost associated with implementing them.

And then for the admissions component, the one thing I was seeing is there would be a no-admission, so meaning neither admit nor deny, settlement. But then there was a lot of negotiation over the findings. And I found that to be really problematic because those are the AG's findings. Like the AG conducted the investigation, they made the findings, and if the defendant is not going to admit to those findings, then they really should not have the ability to negotiate or edit those findings. So the instruction to my team was: you have two options. The defendant has two options. They can either have a neither admit nor deny settlement, but then they don't get to negotiate our findings. Like our findings are what the AG's office found. Obviously, they have to be supported by the evidence that was uncovered during the investigation and if there's a glaring error, yes we will fix that, but we're not going to get into stylistic or other edits to those findings. And then the other option is okay, if you are going to have an admission, then we will agree to have you have some back-and-forth on those findings within reason. So we didn't have this situation which was occurring before, which is there was all this extensive watering down of the findings and yet there was no admission. So I wanted to put an end to that.

But I think there were certain cases where it was really important to get an admission for accountability reasons. And I think the one that sort of most readily comes to mind was the Hank Greenberg settlement where we did get an admission. And that case had dragged on for I think over a decade before it was eventually settled. I mean we went to trial, we started the trial and it settled midway through trial.

Khurram Naik: Can you give us some more context for how the federal enforcement culture varied from the state enforcement culture?

Manisha Sheth: Yeah, I think the federal—and again it part of it is the difference between criminal and civil. So when I was a federal prosecutor I was exclusively doing criminal cases and then at the AG's office I was exclusively doing civil cases. So part of it is that distinction. But I would say as a general matter, there's—I think there's more structure to the approval process in the federal system. So there was definitely guidelines about kind of what was permitted and if you were going to deviate from those guidelines you would have to get approval, and depending on what you were deviating from, it would inform who you would go to for approval. And then there were some matters where you'd have to go to DOJ, Main Justice in D.C., for approval, even though I was in the Philadelphia US Attorney's Office.

And I also think—and this might be a function of the fact that it was criminal not civil—but it was definitely less entrepreneurial. Meaning at the AG's office, you could pick up the newspaper and say, "Well, here's a problem that New Yorkers are facing, how can we solve for this?" And oftentimes at the AG's office, we were able to convince companies to go above and beyond what was legally required, whereas I don't think that necessarily was the case on the federal side.

So I think it was more fluid, there was more discussion about kind of problem-solving—identifying a problem and then coming up with a creative, sometimes creative, solution to that problem—as opposed to on the federal side, it was a little more black and white. Like here's what the statute says, here's what the elements are, can we prove this, can we win at trial? And I think the risk tolerance was a little bit lower on the federal side. Again, that may be because it was criminal not civil, but I think that also was true for some of the parallel investigations we had that had both a civil and criminal component.

But then at the AG's office, it was a little more fluid, and that also could have been a function of the statute. So the AG, the New York AG, has one very powerful statute called Executive Law 63(12) and it the elements are broad. There are some elements that are not—it has some things that are not even an element like reliance or scienter. And so you're able to bring cases that you might otherwise not be able to bring because the statute is so powerful. And the statute has been challenged I think on numerous occasions and has survived. And the AG's office is very protective of that statute, so they're not going to bring a case that has the potential to threaten that statute. So that's something that's kind of always in the back of their minds.

But because they have this powerful statute, I think they're able to kind of do more because arguably if they bring a litigation, the conduct that they're trying to solve for is usually encompassed within the scope of the statute. Because the statute prohibits two or more instances of fraud or illegality, and fraud is very broadly defined beyond just common law fraud to include any misleading or deceptive practice. So it’s—it's a really broad standard.

Khurram Naik: That's such an interesting concept about an institution seeking to preserve its credibility and tools by not overstepping. Just the concept of an institution that has this indefinite time horizon where they can really act in the long term—that's a really interesting institution to take part of. Yes, we have old law—100-year-plus law firms—but no law firm can credibly say they're acting on any kind of 20-plus-year time horizon. So I think that's a really interesting training and mindset to pick up. What states do you find have the most innovative or effective AG offices?

Manisha Sheth: I would say I mean it depends sometimes on the bureau. So I think Connecticut was very strong with their antitrust bureau. Massachusetts and California were both very strong with regard to the Consumer Frauds Bureau. We had—the AG's office, New York AG's office—had an Internet and Technology bureau, the Bureau of Internet and Technology (BIT). I'm not aware of other offices that had a similar bureau, and it might have been encompassed by the Consumer Frauds Bureau. But I think it and it was a small bureau—it only had like six people in it—and the bureau chief was amazing. She was just very creative, very knowledgeable about all the technology issues, and so I found that it was great to have that bureau, not only for their own individual cases, but I oftentimes brought them in on a consumer case or a securities case, or even an antitrust case, to help us figure out issues that were kind of unique to the technology at issue in those cases. So we did a lot of cross-bureau investigations and enforcement proceedings and it was very useful to have them there. But yeah, I think in terms of other state AGs, the big ones are Texas, California, Massachusetts—those are the ones you hear about certainly on the blue states. And I think we saw—we definitely were part of a lot of multi-state investigations, so that was another way that we saw different states taking leadership roles in different cases.

And then when Trump took office the first time around, we definitely—it was more so in the social justice division as opposed to the economic justice division—but there were definitely like labor cases, immigration cases, reproductive rights cases that the AG had to really step up enforcement on because of what was going on on the federal side. And from our perspective in the Economic Justice Division, what we were paying a close eye to was: was there any rollback in federal enforcement that required the state AG's office to step up enforcement?

Khurram Naik: And then let's talk macro enforcement trends. What trends are you tracking at the federal and state level right now?

Manisha Sheth: Yeah. So I think we've definitely been following what's been happening on the federal side, which is a lot. But I think what's relevant for the work we're doing here at the firm is the rollback in the environmental enforcement proceedings—for example, the greenwashing cases, the climate disclosure cases. I think what we're seeing is because of that federal rollback, there's likely to be a step up in state enforcement on those matters.

And it kind of goes both ways. So we'll have the blue states bringing greenwashing cases, but then we're also having the red states bringing cases against companies for making those kinds of promises, saying that those are not in the best interest of the shareholders and that the only objective should be profit maximization as opposed to, you know, sustainability or climate efforts. So I think we're seeing some tension there.

I think the antitrust stuff has pretty much stayed the same; I'm not seeing a rollback on the federal side on antitrust enforcement. I think we may see some on the securities side—some reluctance on the federal side to take on more creative or novel enforcement proceedings, but I think the bread-and-butter cases will largely remain the same at the SEC. So not seeing too much there. There might be some changes on the crypto enforcement where we might see some rollback on the federal side and some step-up on the state side. And then obviously the big one is consumer cases. I think with what's happening at the FTC—the termination of two of the commissioners, Lina Khan has stepped down—I think we might see some difference in the types of cases that the FTC is bringing. And then the CFPB—I think that's going to really see a slowdown in what's happening on the federal side and a step-up in what's happening on the state side.

And I can tell you that when I was in the office and when Trump had his first administration, people in the consumer frauds bureau were definitely focused on the areas where there was going to be a federal rollback and looking to step up enforcement in those particular areas, whether that's student loans or consumer finance with certain fintech products. And I think we're seeing some of that now, like the New York AG just brought a number of—two big matters against earned wage access providers, and I think we saw I think there was a proposed rule by the CFPB that is sort of in limbo and so I think the blue states—I think we can expect to see some step-up in enforcement by the blue states on that.

Khurram Naik: Could you speak then to case resolution dynamics? What are patterns across industries or size of clients where you're seeing the New York Attorney General's office in particular has more leverage, has more success with enforcement? You know, so then therefore those clients are more vulnerable. What are you tracking in terms of case resolution?

Manisha Sheth: Yeah, I think one area that they—and maybe others—are focused on is private equity and private equity's investment in various healthcare enterprises, whether that's—so one example of that is the nursing homes. I’m trying to remember what year this was, maybe 2023 or 2024, the AG's office launched a—well, first they launched an investigation. It started off as very much focused on COVID and the impact of what nursing homes were doing in response to COVID, and then they put out a report on that—it’s publicly available on their website. And then shortly after that report, they commenced, I think it was five or six enforcement proceedings against various nursing homes across the state of New York, all in an effort to improve nursing home care for residents of nursing homes. One of the things that they were very focused on was what they believed to be a difference in the quality of care that was rendered at non-profit nursing homes versus for-profit nursing homes, and some of those nursing homes may have been owned by private equity companies. So that was one area where I think they were focused and may continue to focus.

I think the other one is just sort of consumer financial products and disclosures. So, one of the things that the Consumer Frauds Bureau is very focused on is the adequacy of disclosures, particularly in apps. You have a limited sort of space on a phone to put all the disclosures that the AG may believe are required, and so we will oftentimes see cases that are brought because the disclosures are not sufficient or there's a fee that's charged and it wasn't adequately disclosed at the time the consumer signed up for the service. So I think we can expect to see more of that. And I'm not—it’s not clear to me whether the FTC or the CFPB is going to be pursuing some of those disclosure-type cases.

And then I think the other one that's probably a hot topic is going to be AI and the use of AI and how the AI algorithms are programmed and whether the way in which they're programmed are having some sort of disparate impact on certain protected groups or certain socioeconomic classes. And I think that's something that, you know, has always been of interest to the AG's office, but now that AI has really taken off, it would not surprise me if they have a group looking at that specifically.

And then the last area I think would be the advertising—kind of the targeted advertising to consumers that is based on data collection efforts. So I think those are probably the four areas where I think they are likely to step up enforcement.

Khurram Naik: Going back to that skill set of setting enforcement priorities, you explained there's a lot of creativity that the New York AG in particular has because of certain statutes. It’s such a novel position to be in to be developing theories and developing causes of action that way. You know, there's some creativity involved, like you were talking about for the on behalf of the FHFA, you know, just coming up with this theory that "Hey, you know, there's actually a securities aspect to this, not just contractual." But can you speak to—it was so unique the skill set you gained of setting enforcement priorities—how does that skill set show up today in private practice for you?

The connection Manisha draws between mountaineering and trial prep — that brutal training prepares you for the summit — is a philosophy Patti Burris lives by differently. She developed a 7:2:3:1 wellness ratio to sustain high performance while billing over 2,400 hours.

Manisha Sheth: I think it goes back to the problem-solving, right? So when clients come to us today in private practice, usually they're facing some kind of problem, and usually it's a business problem. And litigation may not necessarily be the best way to solve that problem. And so sometimes we're asked to come up with a non-litigation solution or to use the threat of litigation to solve that problem. And so I think it just depends on the specific problem. But I think what I would say is it's important to understand the client's business—well, the client's industry, the industry in which they operate, and then the client's specific business in the context of that industry—and then get an understanding of that client's specific problem in order to be able to help them kind of best solve for it. And that could take a variety of ways, including litigation, but it may also include, you know, maybe the equivalent of a demand letter or demand letter that threatens litigation but outlines what the problem is. And sometimes it could just be coming up with a business solution or helping the client kind of figure out what that business solution is. And so one of the things that I think has been helpful is to just ask the client, "What does a good outcome look like for you? What would you consider to be a win?" and it's not always going to be the answer is not always going to be prevailing at a trial after a three-year litigation. And so if we know what a win looks like for that client, then I think that helps us kind of determine what's the most efficient way to get to that win, whether that includes litigation or not.

Khurram Naik: Speaking of the most efficient way to get somewhere, something else that you shared with me is that you are a rock climber and mountaineer. And so something you shared is that you enjoy the technical aspect of mountaineering. Tell me some more about that technical aspect. I've barely done any rock climbing, some hiking, nothing I think that moves the needle for somebody in your space. But so tell me what's technical about the mountaineering you do.

Manisha Sheth: So, I think what I would say is—I mean it depends on the kind of rock climbing. I'll talk about what's called "trad" or traditional rock climbing. That's what I really enjoy the most, even though I think it is probably the hardest. And I guess for those in the audience, trad or traditional rock climbing involves placing gear into cracks and crevices on a cliff and then running your rope through those pieces of protection so that if you fall, that piece of gear holds your fall. And so not only do you need to be able to climb up the cliff, you need to know that the protection that you're placing in the cliff is going to hold and so you have to place it precisely.

The thing I love about rock climbing is that it combines both the physical aspect—obviously the climbing—but also the mental problem-solving aspect. And there's no one way to climb a cliff. It often times depends on your own body strength, what parts of your body are stronger than others, how tall you are. And so somebody who's 6'3 is not going to have the same beta that I'm going to have—I’m not 6'3, I'm 5'4—so it'll be a very different set of moves that I would use to climb a wall than someone who's much taller and maybe someone who has more upper body strength vs. lower body strength. And so I do like the problem-solving aspect of it.

And then the third thing I like about it is the focus and intention. You know, a lot of people are touting the benefits of meditation and I've never been able to kind of sit still and meditate, even though I've tried a ton of times. And I know that there are huge benefits from meditating, like just from a scientific perspective, but I haven't been able to do it successfully. And what I find rock climbing really meditative because there is no way you can think about anything else when you're up on that wall. Even if I wanted to, I couldn't think about, you know, a case or a problem. And so your mind is like 100% focused on being present in the moment during the climb, kind of setting your protection.

And then the last thing I like about it is the kind of the fear factor and getting control—you’re going to be afraid. I am always afraid when I'm leading a pitch of trad climbing, but kind of dealing with that fear and finding a way to kind of self-talk your way through the fear is really important. And I think it's helped me become a better lawyer. So I think there's very few things that scare me now in terms of going into court or trying a case because I feel like if you're up on a wall with the potential of falling off a wall, there's that's kind of the ultimate fear.

And it's also patience, right? I think I didn't start rock climbing till pretty late in my life; it's not something I did when I was a kid. And so I think just having the patience to get better at this very slowly is also good—it’s just good because I think I'm an impatient person and so it's sort of forced me to kind of accept that, okay, you can progress pretty quickly up to a certain point but then you hit a plateau and then you really have to kind of be patient to get further.

Khurram Naik: Is part of what you're saying that there's no one physique or set of strengths that necessarily makes someone a stronger climber than others? Is it equalizing in that way?

Manisha Sheth: Yeah, I think that's right. I mean there's certain climbs like I think an overhang climb where it would be better to have more upper body strength or more core strength, but for the most part, at least at the level that I'm climbing at, I don't think there's really much of a difference between sort of male or female climbers. I think you can climb kind of the same grade regardless of body type, and you just do it differently. Right? You might have a different set of moves to get to the top.

Khurram Naik: It’s particularly in the context of we just spent a whole chunk of time talking about a legal career and navigating a legal career—it’s just irresistible to make comparisons between the two. How can you not? And so do you think that you enjoy rock climbing more for the ways it's similar to litigation because you think about building a case, working backwards earlier from thinking about a trial outcome, well then if you're thinking about a climb and working backwards from "How I'm going to do this climb?", maybe you can look at this aspect of, "Hey, there's whether you're 5'4 or 6'3, there's different ways you can achieve the same goal." So maybe somebody who is, you know, the legal brain power-house or maybe someone who's better at the soft skills of working with a judge or opposing counsel and more strong at negotiation—like maybe someone has different strengths in navigating cases. Do you think that you enjoy mountaineering because it is similar to litigation or because it's dissimilar to litigation?

Manisha Sheth: I think it's similar in the sense that it's problem-solving. So, there's a—I think every climb, frankly, there are certain climbs where you've got to sequence the moves in a certain way in order to kind of get past the crux. And one of the things I really enjoy about rock climbing is figuring out that sequence of moves. And it sometimes takes a while, right? Like that climb I may not get the first five or ten times and so I'll have to keep working on it and figure out the sequence. We call it "projecting" a climb. And I think in many ways like that's kind of what we're doing in litigation is like we are problem solving and it could be problem solving with regard to an argument—like this argument doesn't quite work, what can we do to make it better or do we need to throw it out and come up with a new argument? And so I think the problem-solving aspect of it is very similar. And I like problem-solving, I like kind of figuring out the solution for the client or working with the client to figure out the solution.

And I think the other thing, and this was probably more true I think of mountaineering and alpine climbing, which is it is in some ways a bit of a sufferfest. I was just talking to one of my former partners about mountaineering and I did a trip to Alpamayo last July and I would like to do another trip this July but I was telling him that unfortunately I've just been so busy at work that I haven't had time to train in the way I need to train to be able to do this in July—and it’s another big mountain in Peru. And so I was like I probably won't be able to do it this year.

But the thing that is similar I think to being a trial lawyer is that there's a period of pre-trial prep leading up to a trial. The trial is the culmination, the summit—it’s the most important, most fun part of being a trial lawyer, the actual trial. But the pre-trial prep leading up to it is a bit of a sufferfest. It’s like a lot of work, a lot of stress, a lot of like anticipating problems, being ready for every possible contingency. And in many ways that is very similar to the training that goes into getting ready for a big expedition. So I remember last year getting ready for this trip to Alpamayo, I literally—I felt like all I did was work and train. And, you know, there wasn't much time for anything else. And in that way, you know, probably wasn't that fun, but at the end of the day was worth it because to be able to summit that mountain and see the views and, you know, that was just so incredible that it made kind of the sufferfest leading up to it all worthwhile. And in many ways I think like the period of time where you're prepping for a trial is similar to that training for the summit.

Khurram Naik: You mentioned that you came to mountaineering later and so that sounds like a major undertaking. I've had friends who go back to college who were more interested in the knot and so, spending some time outdoors with them. And I just always had the presence of myself as that I enjoy being in the outdoors and hiking and moving my body in that way, but given that it takes so much planning—like that's just not how I am. I don't plan that much around that movement and spending that time outside. If I want to move my body or be outside, those are just I just do much lighter lifts to do those things. And so but I've always admired people who make that allocation of time and you know, I've been wearing Patagonia for a long time, you get these catalogs and see the things these people are doing, say "Wow, that's pretty damn impressive." and uh, I'm wearing the same clothes as you but I'm not doing that. But so I wonder for you how you came to this later and said "Yep, I want to take that on." because it sounds like a major mental allocation of energy, to the mindset of, the identity shift of "I'm the kind of person who does this too." to make time for that. Just I know how busy your your trial practice would be. It just seems like such a major undertaking and and uncommon to do later. How did you come to that? How did you say to yourself "Yep, I can take this on"?

Manisha Sheth: Yeah. So I did do Kilimanjaro I think it was 2012, so that's a while ago. And I mean I think it wasn't a technical climb, so honestly anyone could do it, it's just a hike up a mountain. Obviously dealing with altitude which has its own challenges. But getting to the top of that mountain was pretty strenuous, right? So summit day, the summit push I think is incredibly strenuous. You start kind of in the middle of the night, you hike up in the night with a headlamp, you're going very slow—slowly. The expression our guides used at the time was "pole pole" which means go step by step very slowly. And I remember it being really difficult and I had this wonderful guide who I was—I was literally right behind him and I was just kind of almost robotically following his footsteps. And it was a slow slog up a mountain, but again, nothing technical about it—just one foot in front of the other, slowly getting up there. And I remember getting, you know, we weren't quite at the summit but there was a point at which you could see the sunrise. And um, it was honestly even though we weren't at the summit, there was a group of six of us and the view and just the beauty of being up there, I think it was like roughly 19,000, 18,000 feet, and seeing the sunrise from that vantage point was just breathtaking. And there's something sort of spiritual about it, there's something where you realize you sort of transcend beyond yourself—you feel like you're part of something much bigger. And so it was that feeling of—I don't know whether to call it spiritual or what, but that's kind of what has drawn me to the big mountains. And so we we then eventually did make it up to the summit and you know, it was even even better from the summit.

And so I think that's kind of what has drawn me to the big mountains. I'm not sure why but I don't feel that way getting to the top of a cliff or you know, I did some—I don't think I've done any high-altitude climbing other than Alpamayo last July. But like just climbing up a mountain that's I don't know 3,000 feet, 5,000 feet, I don't really feel that same sense of awe. But what I would say, and I think I've said this before, is like my first love—like rock climbing is my first love and it has my heart, but mountaineering like calls to my soul. And so you know, even going to Alpamayo last year, you know, it was incredibly hard, like honestly it was the hardest thing I've ever done. And it was so cold. I don't remember the altitude being as much of an issue for some reason as it was in Kilimanjaro—like I think I handled that better. But the cold was a challenge. This one was technical, so there was I think seven pitches of ice climbing to get to the summit.

And when we got to the summit, again, it was just incredible—it’s breathtaking. Like the views from up there, it’s really hard to describe. And what I love most about this is like you can't really get to these places without putting in the work. And so there is something rewarding about that: is like it's not just a given, you really have to put in the work to be able to get there. And so I do like that part of it. But I think it's really the spiritual part of it and just realizing that we're part of something just way bigger than ourselves, and I think that's what draws me to the big mountains.

Khurram Naik: In doing this you have to do things that are really hard and but things that you know that you can do.

Manisha Sheth: Well, I wasn't sure I could do it! I mean, I'm glad I made it and I made it because I had a great guide. But it's not a given that you're going to summit any of these big mountains. Like you might have to try a few times. And sometimes you may never make it, right?

Khurram Naik: Yeah, so let me revise my question. When you know you're doing something hard that you know you can do, I'm curious what tools you use. For me, the tool that I use—I live on the 17th floor of this building and so I take the stairs as often as I can. Yesterday was the first time I cracked five trips up, so feeling good about that. But so my simple technique is some team, and if I get past half of anything—if I'm doing something hard and get past half of anything—my simple technique is: physically the second half is going to be much harder, maybe exponentially harder than the first half, but mentally it's much easier and that's what I focus more on. And so I'm curious for you: are there any simple tools when you're facing something that's really hard that you think you're going to get through—what are your go-to tools for getting through really hard things?

Manisha Sheth: I think the first tool is prep—preparation. What I find most stressful is like the question of "Have I prepared enough?" Right? And I don't know if you ever really know the answer to that. Like anyone who's trained for a marathon or a half marathon, you don't necessarily run the full marathon as part of your training; you run something less than that. And then I don't know why, but you just hope that you can make it on the actual day of the race. And so I remember running my first half and thinking, "Gosh, I've run 10 miles, but I don't know that I can run 13 and a half miles." So I think it's preparation. And the same thing kind of happened I feel for Alpamayo—I definitely trained. I trained with a heavy pack, I trained in the Catskills. That's one of the unfortunate things about being on the East Coast is we don't have access to the big mountains. You know, if I was really training seriously, would I have done each of those Catskills peaks multiple times? Probably—I probably should have, right, to get the requisite amount of elevation gain, but I didn't. Because that's just really awful. And so it's like I haven't quite done what I'm about to do, but have I prepped enough to know that I can—at least I've prepped as much as I can within the time constraints of my job? Right? Obviously, if I didn't have the job that I have and if I could just train all day out West, maybe I'd be in better shape.

But I think in the course of the preparation you realize, and then you go and you do it, and then you can assess in hindsight, "Well, I was having issues with the terrain" or "I was having issues with the cold." For the next time around, what can I do better? So for me, I would say, okay, I prepped in this way, but next time I do this, I want to do more cold training, or I want to do more speed training so I can get faster on the uphill with the pack, or I need to do more pack training to be able to carry a heavier pack. So I think part of it is just kind of the trial and error of preparation. So prepping but then modifying and adjusting your prep based on the performance that you do in the actual conditions.

And then the other thing I think is just mentally preparing yourself for kind of the sufferfest that it is, because there's definitely times where it's just it's pretty brutal. And you know, one way to do that is to kind of train in bad conditions, right? So like training in extremely cold conditions, training in a snowstorm, training while it's raining—so like you're not encountering something for the first time. When I was doing Alpamayo, we got to the crux part of the ice climb and it was really literally raining ice, meaning there were so many people on the climb that as they're putting in their ice axes they're causing like a rain shower of ice to come down. And one of those ice chunks hit my helmet and took out my headlamp. So I was at the crux of the climb and I couldn't see because my headlamp had turned itself off because it got hit with a piece of ice. And I had these huge gloves on and I was trying to get it back on and I couldn't because I think I was frazzled and I also had these big gloves on. And so I was like, "Crap!" and my guide is way up there, like probably you know two rope lengths up there, and he can't hear me, can't see me, it's dark. And I'm like, at you know maybe 30 seconds—although it's hard to know how much time passed—but I kind of had a little bit of a panic attack. And then I was like, "Nope, I’m going to have to pull it together because he's not going to come back down for me." And so I did pull it together and made my way up to him slowly. And when I got up there I was like, "My headlamp is not working!" and I meanwhile had lost one of my glove liners down there as I was trying to fix it. And he just pressed the headlamp on my head and he got it back on! But I was like, you know, just kind of dealing like having the mental training so that like I'm in the dark, it's raining ice on me—I hadn't trained in those conditions—and so I thought look, it would be good when I come back and if I ever try to do this again, is to do some night climbs. And so when I came back, I think earlier this year, I did some, they weren't in obviously snowy conditions, but I did some rock climbs in the dark just to kind of get familiar with climbing in the dark and not panicking and having to deal with that for the first time. So it’s like just putting yourself in that uncomfortable position so that when you're doing it for the first time—you’re not doing it for the first time and you're not freaked out if something goes south while you're while you're actually on the expedition.

Khurram Naik: So, I think this is so fascinating to think about the tools that you can port over to your personal life. I think for a while I took cold showers, roughly a two-minute cold shower at the start of every shower. Andrew Huberman was a big influence there. I’ve actually recently started to phase it out. I still get in the shower and turn on the hot water, just let that be what gets me to, you know—so I take—there’s some period of time where it's cold water. But I just I'm not sure on the topic of "sufferfest," it's interesting because I am a believer in challenging yourself. I like being able to stand in the shower when it's cold and know that I can always take a cold shower. If I had to take a totally cold shower—like I've taken, you know, when camping or whatever, just ice cold showers and that's the only kind of water there is—I know I can do that. But I also feel like I don't have to prove that to myself anymore. I feel like—I don't know if I—I guess I've been testing whether how much your willpower or or discipline is expandable versus finite. So it’s something I'm playing with, I don't have a point of view on it yet. But I definitely am a believer that some amount of suffering and discomfort—I’m a big believer in carrying my groceries and like I say taking the stairs and just mentally being prepared to take on difficult things that I don't have to. I sit on the ground as often as possible. I don't have to, there's chairs. So yeah, I think it's a great mindset to have. And I really like this concept that to get to that top, there's no shortcuts. There’s no like you can't buy your way to the top. You could fly there, I guess, get a helicopter to propel you down—I guess that's what you could do, but obviously that wouldn't feel any of the gratification of the climb. So, as a discipline of practice around getting yourself out of your comfort zone and that democratic aspect of 5'4" and 6'3"—it just seems like a really on so many levels of experience, it seems like a really fascinating experience. So thanks for turning me on to this and I guess I'll report back if I end up taking up rock climbing or mountaineering.

Manisha Sheth: Sounds good!

Khurram Naik: Manisha, thanks for taking the time. Super interesting exploration of your world and experiences and I look forward to sharing it with other people.

Manisha Sheth: Thank you so much. It was a pleasure talking with you.

This episode is different from our usual deep dives. It's a practical, punchy 50-minute bootcamp on LinkedIn for lawyers. Sunny breaks down why lawyers think "trust = skills + outcomes" when clients actually want to know if you're someone they can work with, why calling yourself "Attorney" instead of "Associate" plants seeds for career ownership, and how to repurpose client alerts into high-performing posts in under 20 minutes.

We cover profile optimization (your headline and About section are doing 80% of the work), the formula for helpful content (vulnerability + insight = relatable education), and why commenting on major voices' posts is a low-risk way to build visibility before you're ready to post your own content.

Keep reading below for the full link to the episode and the full transcript of our conversation.

Top Insights

Below are the highlights of our conversation:

• Helpful = Vulnerability + Insight: Why the "I'm honored to announce" posts feel safe but add zero value—and how combining emotional relatability with sharp takeaways (like breaking down a 350-page IRS regulation into three points) builds trust faster than credentials alone ever could.
• The 20-Minute Profile Upgrade: Two changes that take under 20 minutes but transform how recruiters and clients find you: (1) Replace "Associate at Firm" with "Attorney | [Practice Area]" in your headline (don't stay mysterious—you're not helping yourself), and (2) Optimize the first four lines of your About section with practice area, years of experience, major matters, and awards.
• Repurpose, Don't Write From Scratch: The safest way to start posting is educational content—take client alerts, articles, or conference takeaways you've already created, add a hook that shows you did the hard work ("I read the 350-page report so you don't have to—here are 3 takeaways"), and post it. Track the impressions and bring those numbers to performance reviews.
• Why Personal Brands Are Taking Over: Law is a people business, and even institutional giants like Blackstone and Meta are betting on personal brands (John Gray running videos, Zuckerberg becoming the face of Meta)—lawyers who build visibility now control their narrative, attract opportunities on their terms, and aren't dependent on their firm's marketing machine.

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Full Transcrip

Khurram Naik: This is Khurram with Khurram's Quorum. My guest today is Sunny Kim. Sunny practiced in Big Law and then did a big reset to discover her passion for helping lawyers find and share their voice through social media. So we're doing something we don't normally do in this podcast—we're going to talk about some specific approaches lawyers can use to improve their LinkedIn presence. So let's get into it. Here's Sunny.

Khurram Naik: All right, Sunny, I'm excited to do this with you. This is going to be very different than the format I've done in the past. Usually I do like a two-hour deep dive. We're aiming for like 40 minutes here. This is going to be short and punchy, and we're going to dive into LinkedIn for lawyers. This is a topic that means a lot to me because I'm so active on LinkedIn, and you have just kind of like blown up on the scene and you're doing such a great job of sharing content for lawyers for how to be active on LinkedIn and sharing your story about how you came to this, which itself is so remarkable. So there's not a chance we're going to cover all the things I want to cover in 40 minutes, but I think this will be an interesting, short, punchy overview of LinkedIn and a little bit about how you've come to it.

Sunny Kim: Yeah, I'm excited.

Khurram Naik: So then how… so you practiced in Big Law, you were a tax lawyer, and now you teach lawyers about how to use LinkedIn, and I think you do some other consultations as well. Give me the short of this story because I think it's such a remarkable story.

Sunny Kim: Yeah, sure. As you said, I was at Davis Polk and then at Gunderson, and I practiced as a tax associate there for about four years. And most recently I was at a private equity fund as in-house counsel and doing some tax and fund formation work there. And last year I think I just burned out, and I knew it was time to leave when I realized that I have the best teammates, like the best boss, I'm doing substantive work that's interesting, and if I still feel kind of lost—like I'm not sure what my next step is in life and I'm not sure what's my reason for getting up and I don't feel super pumped about every day—I was like, I think I need to just kind of give myself a break and figure out what it is that excites me and what I want to do. So I just put in my notice without anything really lined up, which I know is very risky, but I always loved writing and I naturally just gravitated towards it. And after two months of quitting, I just put up a post on LinkedIn about the two things that I feel like I gained since I quit my job. One of them is control over my time, which I value very much now. And that post just resonated with a lot of people. It’s the first post I wrote on LinkedIn, and I think 60,000 people read it, which was huge at the time because I didn't have a ton of connections.

Khurram Naik: That is huge, I have to say.

Sunny Kim: So it just resonated with a lot of people. And since then, I've been writing on LinkedIn, and I just had a lot of lawyers and even founders and executives just reach out to me asking how I write and if I could help them write as well. So I started doing that for free in the beginning, and then people were getting results—like they were getting clients, they were getting seen for job opportunities. So they were like, "I think this is a valuable service, you should charge me for this," which is how my business started. And so now I've been writing content primarily for lawyers and also coaching them if they want to do more writing themselves, but just giving them more instruction on how to optimize the format and the types of topics that work really well on LinkedIn. So that's my short story.

Khurram Naik: That's awesome. And you know, it's funny because I was a patent litigator and routinely people make comments about how patent litigators aren't famous for their personalities. I remember I worked with a tax lawyer early in my career—I didn't work with her directly, but worked at a firm with her—and we had an icebreaker, we're going around the room, and she said… we were all asked like, "What's your favorite book?" and unironically—unironically—she swore up and down she meant it, she said her favorite book is the Internal Revenue Code. So that's I think what patent and tax lawyers are better known for is that sort of… So I mean, I love that you are like a breath of fresh air, I think.

Sunny Kim: Thank you. That’s funny that you say patent litigators have that sort of rep, at least maybe among themselves. Two of my clients are actually patent litigators, and I think they write very interesting stuff. There's so much out there… I think, I mean, it's not patent, but one of the attorneys who attended one of my sessions, she wrote about "The White Lotus" and how there's a character on the show who wears Duke gear pretty regularly, and if that's a trademark issue for Duke, anyways, because he's kind of a shady character. And so she sees those little things just from watching shows, like media. There's a lot of trademark and patent issues that people may be very curious about, I think especially with fashion brands as well. So I feel like compared to tax law, you guys probably have a more interesting take on things that people care about, but that's interesting that you guys have that sort of rep from amongst yourselves.

Khurram Naik: Yeah, for sure. And yeah, I think there's lots of ways to take pretty dry topics and make them interesting. I think we've probably all had an experience of maybe school or law school, a course in law school or undergraduate where there was a course heading into it that we thought was going to be really boring and then somebody really made it come alive through skillful storytelling and vivid anecdotes. And so I'm really struck with your LinkedIn presence. I think you do a great job of sharing helpful ideas, sharing moments and vignettes from your life, even really small ones, but that still help people get some sense of insight and transformation. I feel like I can be really interested—there's so many ways we can jump off and talk about LinkedIn for you and what works for you. I think the storytelling part is really interesting to me because I sense that you intuitively, or maybe you're doing it in a structured way, you include transformation. Like I think that's a key part of every part of your story—like from that first post about how you came to quit your job and then were just figuring things out, and then that iterative process of sharing publicly of what you were working on and building and getting people to buy into and cheer you on in your story. It seems to me transformation is a key part of that, right? Just even the smallest moments, what was the transformation that I experienced that is an insight to someone else? Does that resonate with you?

Sunny Kim: It totally does, and that's interesting you mention that. I hadn't thought of it that way, but I'm just thinking back to a couple of my last posts and yeah, there is definitely that transformation arc. And I think that kind of content resonates with a lot of professionals, but especially lawyers because I think in our profession there's a tendency for people to want to show their most perfect side of themselves, right? And you want to be perceived in this really polished way, which I totally understand, that comes with the territory. But I've seen from not just my own content but from other lawyers who are sharing stories where they highlight transformations where we've all been in that place where we felt a little bit underprepared or just kind of trial by fire in a way and we weren't fully… we didn't feel fully equipped to handle the responsibility we were given. But somehow we had people alongside us or maybe we just figured it out on our own and got from point X to Y. Those stories work really well because I think so few lawyers are willing to be vulnerable about that. But that earns people's trust because I think so few people are willing to share that, and it is really showing your growth, right? And your maturity and your ability to even thank other people who are working with you to get to that transformation. So I think it builds a lot of trust and that's actually helped not just me, but like a lawyer client of mine get client leads because there's just a lot of lawyers out there who are really good at what they do. But I think the people that lawyers… like the lawyers that people want to work with are lawyers that they feel like they have a connection to and they trust, and I think sharing stories like that builds that trust.

Khurram Naik: I think trust is such an interesting word that you're connecting here because, yeah, I'm so interested in what the connection between trust and insight is. And maybe the way that I'll explore it is because I think how lawyers typically think they earn trust—you hear it all the time—is "Oh, if you just do really good work, that's what will make you trust me. You'll see I'm excellent in court, I win all these cases, or we get all these deals done," whatever it is. I think lawyers publicly and maybe privately as well assume that that is the direct connection. And I think lawyers are very skeptical of things like… they know that relationships are important, and I think they're still very skeptical of that. I guess one way to explore… I guess I'll be interested in your take on that. What is the connection between trust and some of that vulnerability you're talking about? Because I think so many lawyers think it's "trust equals skills." Show you my skills and outcomes, that's what will make you trust me.

Sunny Kim: Yeah, I mean, I think there's a lot of layers to building trust. So I do think there is a lot of validity in establishing trust through doing good work, obviously, and there's also trust that's built by sharing helpful information with people. So if you are the lawyer that is proactively educating clients—let's say like if you're like a fund lawyer like me and you are sharing knowledge on LinkedIn about different financing options for anyone who wants to raise funds for like a startup or something—then I feel like because you are providing that helpful information to someone proactively, you are kind of establishing that trust. And then once they know about you, then they're going to be able to check you out and read about the different matters you've worked on to even build that trust further. But the thing is, I think there's a lot of lawyers who win a lot of cases, do great work, have a lot of transactions on their resume, but I think that next level is establishing, "Do I want to actually work with this person? Does this person seem like someone that I could see myself actually collaborating with and enjoying the process with?" And I think that's where the more vulnerable sort of, "I'm a team player and I acknowledge other people who work with me and I'm a mature person who is able to show that I am growing and I'm not perfect"—I think that's where people kind of connect on a deeper level aside from just doing good work or showing that you've done good work.

Khurram Naik: Your comment on the growing thing is so interesting. Like I… it's so interesting because I value growth and I communicate around how I grow on LinkedIn, but I didn't tie that directly to the value to a client to say, "Oh, you are willing to say you're not perfect and grow" because I think even I assume that clients want somebody who is fully formed and perfect or whatever. So why do I share that then about my personal growth? Maybe I intuitively did it for the reasons you're describing without realizing it.

Sunny Kim: Yeah, I see posts of yours where you do that.

Sunny’s courage in quitting BigLaw and building something new reminds me of Jaimie Nawaday, who took a different kind of career risk — launching Disrupting Drinking as a BigLaw partner, putting her reputation on the line to challenge the corporate cocktail culture.

Khurram Naik: Okay. Because I mean, I'll say that I explicitly have a formula that I keep in mind for myself and I share for other people, which is—I think the goal is… I had a mentor early in my legal career, a litigator, who a simple principle that he used in his advocacy was rather than disparaging the opponent or getting hung up on some technical aspects of their brief or whatever, what he would do is say, "What opposing counsel has done is not helpful. Here's what's helpful." So his North Star was "helpful." And that has been my North Star since then as well. I find that to be such a powerful tool—to focus on what is helpful. And so for me, for LinkedIn in particular, I think I have a simple formula: Helpful = Vulnerability + Insight. That's my simple formula for LinkedIn because we've all seen one or the other. We've seen things that are imbalanced on vulnerability or imbalanced on insight. So if it's got too much insight, then it's just like, "Here is a digest of the latest Supreme Court decision." It's just like, "Okay, I've got the raw facts and legal analysis you just dumped on me, but I can't connect to this dry subject matter or you, even if I'm interested in the subject matter." It's just like, "And now what? What do I do with this now? Okay, so I have these facts, I've lodged them somewhere in my head, now what?" And you, lawyer, I know nothing about you. Yes, I know that you're… I can see from this digest that you are capable of reading a Supreme Court decision and distilling the essence of it down, and okay, that's helpful that you're able to make something complex into bullet points. That's valuable. But other people can do that too, and just why would I work with you versus another lawyer? What's good about you or your platform? So that's the imbalance in insight. Imbalance of vulnerability are people who come and just dump all their emotions like, "I cried in my office and it was so hard to get through this day." Okay, and what do I… that's human, I get that you had an emotional experience, I get that, but what do I do with that? You know? So both are very extreme, they're not helpful. But if you combine the two, then what I'm showing you is like, "Hey, here's some maybe hard-won insight. I gained this insight through some hard-won experience"—so vulnerable plus insight. And so then it just becomes a lot more relatable to say, "Okay, yeah, so right, I see how all of us experience challenges, I see now how you can get insights on the other end of that. It can be counter-intuitive. So I relate to you in that you went through something difficult and got something valuable out of it. Now you're sharing with me, that's so helpful you're doing that." And so like, hey, you're helping me, you're relatable, you're the person I'm drawn to. So like that to me is my goal. And it sounds like you and I are both on that same…

Sunny Kim: Yeah, I think I just… I would love to hear your example post that you can think of that does both of that in one post. Because my approach has been if it's like educational content, then it's educational content especially for lawyers. But like you said, it's really helpful when they break it down in a way that's actually coherent and you're able to understand it instead of just saying, "I wrote this post or this article about this" and then just linking it. Like the educational post should try to summarize what the article's about and actually kind of… it's not about you, it's more about the reader and your future clients and why they should even read it in the first place. But that's like a separate bucket in my mind from the more relatable post. And with mine, there's always… there is like a transformation, but there's always some sort of underlying takeaway that is good. So as an example, when I wrote a post last week about just me not having M&A experience and joining a firm where that would be my focus, within that post I talked about a mentor at my prior firm who was really beneficial in teaching me M&A from start to finish. And so underneath that is basically me acknowledging my mentor and how much of a help he was, and also kind of promoting my old firm, Gunderson, about their senior lawyers having a big investment in their junior lawyers. So there is transformation in there, but underneath that there's like a deeper message that I'm trying to convey. And I don't want it to be like just a sob story of just hard times and it ends with that. That doesn't… that’s not an effective post. There has to be some sort of overarching growth or gratitude or a reflection that's helpful for other people to understand.

Khurram Naik: Yeah, that's fair. And probably as a practical matter, maybe a better way to put this is like there's a spectrum that both of these are on. Any given post is on a spectrum of these two qualities. And yeah, some posts are definitely… it's not even, right? It's not like 50% vulnerability, 50% insight. There's definitely like one post is going to be heavier on analytics, one post is going to be heavier on emotions. And yeah, I mean to your point, like I'm thinking of… there's periodically I revisit, you know, the Big Law associate chart. And something that I… you know, I was a life science major and so I'm used to studying charts and making conclusions based on data. Like you look at data and say, "What is the story this data is telling?" And so, looking at the associate chart, the story that I see in that is that, you know, post your fourth to fifth year is really when the inflection point starts to take off for your comp. And so, but then it starts to plateau past, say, your sixth year. So it's like this kind of S-curve. Well what accounts for that? And so I connect that to your value as a lateral associate—how early you frankly don't have a lot of value because you don't know anything yet. And then you know something, you know enough between your third and sixth years, maybe more third and fifth years. And then from then on, you're kind of locked into your firm because you're too senior for another firm to bring you in because they don't have enough runway typically, especially for litigators. And so that chart, like that's a pretty… that's a very analytical approach to that topic. And so what I'm trying to do as far as maybe vulnerable is the wrong word used, but maybe emotional is a better word used. And so maybe helpful equals emotional plus insight because I'm not talking about some personal experience I had there, it's not a vulnerability that I'm talking about there, but the emotional aspect I'm saying is I'm helping people understand what that means for them and how they're valued, how to think about themselves, and create some awareness of "Hey, here's something you have to be aware of—that this chart is analytically, objectively telling you this data that you can make this strong inference from." That's… I'm arming you with a tool to empower yourself to take control of your career so you make decisions about whether or not to lateral and the consequences of not doing that. So it's empowering people to share this content.

Sunny Kim: Oh, okay. Yeah, no, I see that. I definitely see that. It sounds like that would be educational plus relatable content.

Khurram Naik: Maybe that's what it is. Okay. Helpful plus relatable content.

Sunny Kim: Because they're getting that analytic broken down by you, but you're also translating how that analytic really impacts them and kind of factor in to whether or not they want to lateral or not. So there is more… it’s not just educational, there's some sort of relatable component where you're relating it back to how it impacts them. So that's just how I'm translating in my mind, but yeah, I think that's a really good example. And I was actually… yeah, I was thinking of another… it wasn't my post, but I saw… I think that's a good structure because I saw someone else do that with a case that she had like… or like she basically got a major approval that's really hard to get for her immigration law firm, but she also talked about the vulnerable part, which is that this was like a really big struggle because they weren't able to get it in the beginning. And she kind of walked through the different things and the approaches that she took to eventually get it. So it educated other people about how they could also get the same approval by taking those steps. But then there was a transformation because she got from point X to Y. And it’s not saying that she sucked or anything, it was actually like very relatable and like in a way like, yeah, transformational. Because everyone has to start from somewhere, right? And when I talk about transformation, it's not saying like talk about a time when you like really sucked and made a bunch of mistakes and you failed a client. It's more like something that everyone can relate to where you're junior or you're doing things for the first time, and that's just relatable for everyone. Everyone's been in that vulnerable point. And it's like, okay, like what did you do to get and evolve from that point to get to where you are now? Like I think those are the ones that work well, especially like I feel like people get promoted or they get like recognized on certain lists. That the transformation angle works really well when you share those posts because it makes you not just seem like you're bragging about the award. It's also like, "Hey, like I got this award, but it took like these steps or it took this mentor or my colleagues to help me really get there." And that's a much more relatable sort of promotional post compared to someone who's just saying, "Hey, I've been… I'm honored to announce I've been…" so, yeah.

Khurram Naik: Yeah, and with my podcast, what I strive to do is carve out the vanilla middle of what you just kind of… what you just talked about where, you know, what I don't do in my interviews is say, "Hey, can you tell me about the importance of hard work, mentorship, and network?" You know, just like… we've all… there's all kinds of mainstream legal publications that will have… you can pull up any one of their interviews and the headline is something about that, right? And so what I try to do in these episodes is I say from the outset, I when I'm talking to the people I interview I say, "Hey, we're carving that out. That is something that we are not doing here. What we are going to do is the two extremes on the other end, which is tell me about the very real challenges you have faced and face today. And then also talk about… so that's what's going to help us apprehend around the other part, which is what makes you really good? What is the strategy, the skill that you've applied? You can tell me about the luck, sure, I'm sure there's some luck, I'm sure there's a team involved. I want to hear about you—you did something exceptional, what was that?" Because no one's going to be able to really learn from what you've done if they don't really understand what you've done that's exceptional, and they're not going to relate to it—you're not going to be like a relatable person unless there's something vulnerable about you that they can relate to. And just like, if you just sound like a machine, "No, I'm just… I crush things, I work 100 hours a week, I write the best briefs," then like, "Okay, like you're just like some insane robot that I just can't relate to at all. It's just completely irrelevant to me that you are successful in that way." So I work really hard to help people… and it's hard for people because people are not used to talk about either of those things. They're not used to talk about things that I'm not good at, and people are not good at used to talking to things that they're really good at. But I think that's where the really good stuff is happening.

Sunny Kim: So you take this moment to get that sort of challenge plus why you're good at something from your guests.

The trust-building Sunny describes — vulnerability plus insight — connects to how Dai Wai Chin Feman approaches networking. He calls it non-transactional generosity and invests daily in relationships without expecting anything back.

Khurram Naik: Yes, and those two things aren't like… this isn't like a LinkedIn post where those two things are happening in one story or whatever, but those are two aspects of each of these lawyers I'm looking to draw on in order to learn from them. Because what I'm going to carve out in the middle is the vanilla boring stuff of "I'm so honored" and "I'm so humbled" and that kind of stuff. Those kinds of parts of their story, the canned part of their stories is what I'm carving out from there.

Sunny Kim: Oh sorry, I wasn't sure if you're asking a question or if that's just making an observation.

Khurram Naik: No, just making an observation.

Sunny Kim: Yeah, no. Yeah, it's funny because someone mentioned for every lawyer post that starts with "I'm humbled to announce" or "I'm honored to announce" or "I'm thrilled to announce," there should be a tariff on those posts. Yeah, there should be. It’s just so overdone and it's so generic and it's just not, I don't know, it's not really memorable. And I also think it kind of turns people off a little bit because it's just so overdone and we've seen it so much. But I think there are really good ways to be more creative about it, and I actually do see more of it in the feed compared to prior years—I don't know if you feel the same way—but I think there's been more genuine storytelling from lawyers as more and more people actually come onto that platform, which I think is great because there's more examples for people for people to draw from rather than the very typical posts that we've all seen.

Khurram Naik: I want to get into some… you know, you've got some great brass tacks so we can get into for some actual tips for lawyers. So I want to get into that, but I think my observation that I'm curious to get your reaction on is I think that many lawyers think that vanilla middle just now, that's what's safe. And so that's why they put that out. It’s like, "Well, I'll just put out what everybody else is putting out." But by definition, that will not stand out. The only reason to make a post on LinkedIn is to stand out. If you're trying to say the same thing as everybody else, you might as well not post. It literally adds no value to say what everyone else is saying. You wouldn't do that in a brief, right? Would you say something that the judge has already heard? No. If you're having a reply brief, you better say something that you didn't say in your opening brief. So same thing on LinkedIn, same principle. If you're going to say something, say something different. It doesn't mean to say something crazy and just like, you know, wear Groucho Marx glasses and just be a goofball or whatever, but you have to say something different.

Sunny Kim: And different doesn't mean unsafe, right? Different can just be adding one more layer that everyone else is not adding. Like in that post where you're saying "I'm honored to announce," instead of just saying that, just adding people who you want to thank, who helped you get that award or promotion or whatever. It’s not unsafe to add it, I think it's actually better and enhances your post. Because if… I mean, we've both been lawyers, imagine if we were tagged in a post like that, like how good that would make us feel for someone to win something big and acknowledge us as part of that achievement. That's actually better for me and for you. So yeah, I definitely hear you that people are more inclined to stay safe, but like you said, the way to stand out… because it's really at the end of the day, it's a visibility game and you want to get your name out there. And the reason why these social media platforms are effective is because you're doing it at scale as opposed to meeting each person one by one. So yeah, to do it effectively, you have to kind of lean into adding something that not everyone else is doing, but still keeping it professional.

Khurram Naik: Agreed. So let's get into some of that about how to present yourself. So you've got some ideas on profile optimization, your headline, your about me section. Tell me about how lawyers should think about presenting themselves in that way.

Sunny Kim: Yeah, one really simple tip that I think any lawyer can use is to optimize their headline. And I know that there are so many lawyers who just use "Attorney" or "Associate at [Blank] Law Firm." But even just adding your practice area goes such a long way. Like I want to hear your perspective on this as well to see if you agree with this. But when you search for lawyers, if someone just has "Associate at Firm Name," you're not able to see if they qualify for the position that you're trying to look for, right? Like if you're looking for a tax associate, it's much harder for you to find them if they don't have that in their profile. Is that right?

Khurram Naik: Yeah, and I think… well this is really interesting because I think any number of lawyers might think that there's value in being mysterious, and any number of firms model that, right? So there's like, I think particularly the white-shoe firms are much more… like if you pull up a lawyer's profile on one of these white-shoe firms' pages, it'll be extremely bare-bones and just say, "This is a corporate associate." And I don't know the reasons for that, but the easy cynical take would be that that makes it difficult for that talent to find its way to other firms because then I can't identify what this talent can do if I'm a recruiter. And so, yeah, I think no one is doing themselves any favors by being mysterious. I think it's helpful to share, "Here's what I do, here's what I'm good at" along the lines of what we were just talking about. And you don't have to have a narrative about it. I know that any number of lawyers are concerned about whether sharing something on LinkedIn is attorney advertising and contravention of rules of professional conduct. But just, even if it's just "Hey, I'm a private equity funds regulatory lawyer," whatever it is, "I'm a patent litigator," just having a short description of your subject matter just seems to be pure upside and no downside.

Sunny Kim: Yeah, definitely. Because… yeah, that's interesting. I have noticed that about certain firms keeping their associates mysterious. But you want to be in control over your own career, right? And if there is a really good opportunity, you want to make it easier for people with those opportunities to find you. So I think updating your headline to show your practice area… and I also want to add that for associates, instead of just saying "Associate," I would just advise that they put "Attorney" because I think that establishes more credibility and especially if you're trying to build thought leadership and speak from a point of a trusted advisor, an expert advisor. I think that title change alone helps you establish that. And we've all kind of been in situations where we look up the other lawyer that we're going to speak to before a call, right? And there's definitely… if you actually just say "Attorney," people have to scroll through and they could probably figure it out based on when you graduated from law school, but that's just a lot of work. And you can kind of have a little bit more confidence going into negotiations or other matters if you people don't really know that you're a first or second year or third year associate. So those are the two tips that I recommend for headlines.

Khurram Naik: I couldn't agree more with that. And I think the latter is going to be difficult for a lot of associates at law firms because the associate title is… it comes with a partnership track that you're on. So there's attorneys at firms that are off-track… if attorney is your official job title, that 99 times out of 100 means that you're not partnership track. And so associates correctly understand the cachet in being an associate. But when I practiced law, I did exactly what you did. I put "Attorney" on there. I knew that, yes, I'm aware that the cachet is with associate when it comes in Big Law, but the purpose of LinkedIn isn't for me to… I'm not trying to win points in the Big Law sphere. I'm already in there, so I already have those points. This is an option for me to get points with people who aren't in the legal sphere. So they just… they don't see me as "Associate" or "Partner," they just see me as an attorney, and they'll come to me then. And so, yeah, I completely agree with you. And I can't say, you know, if I was a more skilled Big Law associate I'd still be there. Like there's a reason why I'm no longer in Big Law because like that was not the practice of law in a Big Law format in the time that I was at a firm, like that was not my forte. But I do think "Attorney"—calling yourself an attorney on LinkedIn was something small within my control to take ownership of my career and that planted the seed for where I am today where, you know, I'm an entrepreneur and I own my work product. So I think that's the direction you're heading in in your career and I assume that it is because that's why you're taking ownership of sharing things on LinkedIn. Then yeah, I think you definitely should think about calling yourself an attorney and not just an associate.

Sunny Kim: Yeah, I agree with you on that. And along the same lines, I think on LinkedIn people are not really spending a lot of time on really understanding who you are. So you want to make it super easy for them to get that information very quickly. And one of the best ways to do that is to add an About section. It's just the first section that will appear if they scroll a little bit down, and it will only show the first four lines. So in those first four lines, you want to make sure it's very clear what kind of practice area you're in, what are the types of clients you serve, your years of experience, major matters that you've handled, as well as any awards or publications that you've been in because all of those things are trying to establish credibility and build some level of trust from the get-go. So people who optimize their profile to just maximize those first four lines, I think, really get those opportunities much faster than people who spend or that kind of waste that space or don't even have that at all. So that's another tip I recommend on your profile.

Khurram Naik: Great. I think that's helpful. Both of these—I mean, how long could this possibly take someone to rework? Maybe it takes a little time to think about, but this seems to be two things that can get done in under 20 minutes.

Sunny Kim: Oh yeah, for sure. And you can just… I think you can just take ChatGPT or any other gen-AI tool you use to paste in your bio and have it generate something for you for both of those sections. So yeah, I definitely think it could be done in 15, 20 minutes. And I also think you bring up a great point earlier about taking ownership over your career because I think a lot of us kind of feel safe in having the credentials and being at a Big Law firm, and we believe I think early on, because no one else tells us otherwise, that that alone is enough. But I think the world is very competitive and the higher you go up in your career, it becomes even more competitive. So you really need to kind of fend for yourself and watch out for your best interest as an attorney and really take ownership over your career. And building a presence on a social media platform and really just putting your name out there makes it so much easier for you to gain that control over your career whichever direction you decide to take it. So I think it's important to be intentional about how you want yourself to be perceived and how that perception is going to help you get to the opportunities that you're aiming for.

Khurram Naik: And so aside from seeking opportunities, what are other reasons why people should consider writing on LinkedIn? Like what is it that people… what are the reasons why people would even want to make posts on LinkedIn to begin with?

What Sunny teaches on LinkedIn, Ambika Kumar did through traditional channels — building a nationally recognized First Amendment practice from Seattle through articles, treatise chapters, and proactive thought leadership. Different platforms, same principle.

Sunny Kim: The main reason is law is a people business. And at the end of the day, of course they're going to contact law firms and like look at their names, but they're going to have to work with certain lawyers at those law firms, and you want your name to be the name that pops up because you have done the hard work of investing time into building a presence where people already know about you and trust you. And at the end of the day, yeah, like you can't just depend on your firm or company. You want to make sure your name is out there to get those clients, those firm leaders to sort of recognize you first. And that is why I think a lot of people, not just lawyers, are building their presence on LinkedIn. Before, I think Blackstone, its name would just stand on its own, but now you see John Gray, who's basically going to be the next CEO, he's investing time into building his own personal brand. We see running videos of him because he wants to also be more relatable and build trust with people like his institutional clients. And Mark Zuckerberg, same thing. I think before he was kind of… I think Meta or Facebook had a bigger presence, but I think he's seeing that there's other tech leaders who they are becoming the face and not the company. So everyone is sort of leaning into their personal brand outside of law, and I think law is starting to sort of gain traction and follow that trend. But the reason is that people just know that personal brands are where the world is going. And so we all I think need to lean into that.

Khurram Naik: I think part of what you're talking about, I know in tech circles there's a lot of distrust of traditional media outlets and so there's this concept in tech circles of going straight to your audience—you know, just getting direct access. And of course you're using things like social media platforms to do that, but you're not using traditional news outlets for that. So I think that's also driving a lot of it where they can shape the narrative directly. And so I think the same principle follows—that that law may be slow to it, but then you have an opportunity—this is an amazing opportunity to be early to it. And I think some of that's important to underscore as well—is like by definition if there is an opportunity, that means you're early. And by definition, something early means there's not going to be a bunch of other people saying, "Here's how to do this." So like if this looks weird to you, if this is like uncomfortable for you—like "I don't see other people doing it"—that's what makes this an opportunity. If everyone was doing it, there would be no opportunity.

Sunny Kim: Exactly, that's exactly right. Did you read that article by Alex Sue where he talked about the benefits that he got out of establishing a presence on social media?

Khurram Naik: I'd be surprised if I didn't, but I don't recall this one.

Sunny Kim: Oh yeah, but he actually mentioned exactly what you mentioned, which is you are able to shape your own narrative because you may not always agree with what your firm is doing or what your company is doing, but you want to put your own version of how you perceive yourself and how you want to be perceived out there because that just gives you so much more control over how you are as a person as opposed to just having a company or firm doing that for you. So I think yeah, that's one of the main reasons that it's so important to build and lean into a personal brand. You put it a lot better than me, but yeah, I just wanted to talk about that again.

Khurram Naik: So we're on the same page. And look, I know we're running into… we've got a stop here coming up here in a few minutes. Is, yeah, I think the most likely answer is that you'll have to come back and we'll have to talk for hours more about all the ideas that you have about sharing ideas. Are there one or two—now that we've done… I think it was helpful to establish the reasons why someone would even post on here to begin with—are there a few tips, one or a few tips, however many you want for how people should think about what they'll write?

Sunny Kim: Yes. I think the easiest way to start is to start with educational content. Because I think there is some courage that people want to work up before they start sharing more relatable posts. So the first step I think that's most low pressure for people is to repurpose things that they've written—maybe client alerts, articles—and post about that on LinkedIn. But add something to it where you summarize what it's about, who's the audience, why they should care about it. So once you get that first post out, it's going to feel much more comfortable for you to start exploring more relatable posts that really deepen the trust. And after that, if you still want to work up more courage to post, I recommend going to other major voices in the legal industry and commenting on their posts because that is one mini-post that I think of where you are still sharing your perspective and putting your visibility out there. And especially on big accounts like yours, for example, people really read those comments, and you can even see that now LinkedIn shows the number of times people view comments, and it could be very significant. So that is one other way where you could chime in with your own experience or thoughts that really add value instead of just saying "Great insight" or "Congrats" or whatever. And then after that, you can start off by writing a more relatable post like we talked about—maybe something about your award or a reflection about your career journey and why you joined your firm or your practice area. Those are things that are not really risky, and as long as you preview to the people who are tagged in the post that "Hey, I might mention this to thank you for this thing you did for me"—like I've done that myself with all the partners that I've written about, they love it. So and then, so I would do that. And then all of these posts that you have written about the firm or that are adjacently related to the firm that put the firm in a great light, I think you should track the metrics of those posts and the impressions, which is basically views, that you've gotten on those posts. And then bring it up in a performance review or talk about it when you interview with another firm that you want to lateral with—that "I did all these things that really promoted my firm and it got in front of 20,000 people." Like that's a value-add that I think shows that you have like a business development mindset in terms of not only promoting yourself but also getting your firm's name out there. So I think those are some of the tips that you can just immediately use.

Khurram Naik: Yeah, I love those. Those are perfect. I can resonate so much with that because I remember when I was an associate, like "What's safe? What's safe to post on?" And I remember for… we had a blog on tracking the biosimilars litigation market. And so we would have little biographies of the different people who contributed to the blog. And so we did add some like personal questions in there just to add some flavor and make it more fun in that way. And so there's a post about… so when it was my turn, I talked about "Hey, here's this mango smoothie that I've been making," whatever. And so then I decided to say, "Hey, when I got on LinkedIn, okay, here's this mango smoothie I'm making and here's like a little bit about me from my firm blog." And so like that was me doing this incremental stretch that felt safe. Like, "Okay, it's a little uncomfortable to talk about a smoothie I made, I know it's not really professional, it's not like something that relates to my work as a patent litigator," but a lawyer I worked with messaged me saying, "Oh yeah, I saw your mango smoothie thing, that was great." So it was like, "Ah, okay, so people… it's okay to be relatable and just share yourself." And so just the things you're talking about about repurposing existing content from your firm or things that you've done or talked to mentors—I love that because it's just like small steps that are safe to just practice sharing ideas. It's also when you talk about repurposing, it's not writing from scratch because, yeah, if you're busy as hell as an associate or other lawyers, you don't have time to sit down, the luxury of sitting down and work on some new post. So just make it easier for yourself, already have something on the paper that you can work with and just digest. And like you say, ChatGPT is a tool for getting things out the door. Like if I was new to this, I wouldn't be shy at all about using ChatGPT to generate the substance of a post because that just gets me in the game, just gets the ball rolling and plenty of room from there to add your mark and stamp on it. But it just gets the ball rolling, gets you the identity of the kind of person who makes these posts.

Sunny Kim: Oh yeah, 100%. And because you wrote the article, even if you used ChatGPT to think of a good hook and write it, you can verify that it wrote the correct information because you wrote the article and you know about it. So you can totally leverage ChatGPT. I would just highlight that when you write posts, it's very important—and you know this really well too because I see your hooks are really great—it's important to make sure the first three lines are what grab people's attention. So you don't want to use the first three lines to say, "I wrote this article about this topic" and just use all this legalese that's hard for people to understand. A very simple framework is to show that you did the hard work. So let's say it's about digital asset reporting—the IRS released the 350-page report about it. How I would do it is saying, "IRS released a 350-page final regs on digital asset reporting. Three takeaways that crypto companies should know." Because that shows that you did the hard work of reading the regulation or just reading the full thing and you're just breaking down the most important points that people need to know. And that could apply for any agency regulatory updates, cases… but people love when you do the work for them and then they're just getting the takeaways. So that's a really simple framework that you can use.

Khurram Naik: I love that. And what I would add to that—again, that's very safe to do that. And what you could do that was like if you want to stretch a little bit is to challenge yourself a little bit, I should say, is say, "I saved you the five hours of reading this, and here's the three points." Like to really call out like, "Oh my God, that would have been five hours of my life and you spent that five hours and now you're going to share with me? I'm in."

Sunny Kim: People love that! And people love even like when you go to conferences, like "I went to a two-day conference talking about this topic. The most important takeaways from panelists," and even tag the panelists. They love that, it gets your name in front of them. This is really low risk, and if anything I think firms really like that because it puts your work and your association with the firm on other people's radar.

Khurram Naik: Yeah. I think we could go on for a really long time. I think you've got so many good ideas here. So reluctantly I think we should wrap up now. But Sunny, this is amazing. I love the energy you bring to this. I saw you attended your free session recently where you were sharing these ideas. Your presentation was phenomenal, your energy was super high, people throwing you questions every direction and just like no matter what the question, you were excited to take it on. So you have such a passion for this. And so I think you're already making a huge impact from the people that I know because I've mentioned you to several friends of mine and they said, "Oh yeah, I just… I love Sunny's work." So I'm so happy to have you on here and then I'm hoping that you'll say yes to another one of these.

Sunny Kim: Oh yeah, I'd love to. Let's do a full one next time. I will make sure I have a lot of tips to share because there definitely are more. So I would love to come on again, and I want to thank you again for inviting me. This was a lot of fun, it just kind of flew by. So we'll have to do another one. But thanks again for having me.

In this conversation, Randy breaks down why he won't take litigation funding at 20-30% interest anymore (he and his partner are $1.2M out-of-pocket on current cases), how explaining complex legal ideas to non-lawyer parents at school sharpens his storytelling muscles, and why playing poker teaches litigators to stick with the right process even when outcomes go sideways. He also shares the moment he realized other firms passed on a case because they were "too conventional" in their legal analysis—and how thinking in edge cases led to class certification and a lucrative settlement.

We cover the business model of a plaintiff-side boutique (his ideal mix: 1/3 hourly, 2/3 contingency by time invested), why jury consultants who go to trial 20+ times a year know what resonates better than any lawyer, and how to reverse-engineer a litigation strategy by asking "Will this case win at trial?" before deciding which claims to pursue.

Keep reading below for the full link to the episode and the full transcript of our conversation.

Top Insights

Below are the highlights of our conversation:

• Narrative-First Case Selection: Randy evaluates every contingency case by asking "What story will we tell at trial?"—not just "What are the legal claims?" If the jury won't like the client even when the law is on their side, that's a red flag. Starting with the end narrative drives every strategic decision: which claims to pursue, what discovery to develop, and whether to take the case at all.
• The Hidden Cost of Litigation Funding: After paying 20-30% annual interest on a funded case, Randy realized: "If I'm confident enough to take this case, why am I giving away so much upside to de-risk it?" Now he and his partner self-fund $1.2M+ in contingency work, reserving third-party funding only for cases they couldn't afford to take otherwise—because believing in your process means backing it with your own capital.
• Poker, Parenting, and Storytelling Muscles: Randy credits Texas Hold'em for teaching him to model probabilities, handle bad outcomes when the process was right, and recognize when luck bailed him out. Explaining cases to non-lawyer parents at school? That's his storytelling gym—reducing complex ideas to something people want to understand more about, with respect and authenticity.
• Why Jury Consultants Change Everything: Randy's firm goes to trial 1-2x/year. Jury consultants go 20+ times annually and have done it for decades. Hiring them as trial approaches gives Randy insights on what resonates with juries that he couldn't develop on his own—turning good trial prep into great trial prep by learning from people who've seen every narrative play out.

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Full Transcript

Khurram Naik: This is Khurram with Khurram's Quorum. My guest today is Randy Gaw. Randy is a co-founder of the law firm Gaw Poe. I found Randy through his posts on LinkedIn and was struck by his somewhat unconventional approach to thinking about and talking about the kinds of cases he litigates. In this episode, we talk about the path from Big Law to launching your own firm, the business of a boutique law firm, case selection, strategy—a lot to cover here that will be very interesting for anyone who is looking to launch their own law firm or curious about what it's like to jump to the other side of the V. Here's Randy.

Khurram Naik: Randy, thanks so much for getting on the podcast. I am really interested to have you on because of your path to building your own law firm. You started in Big Law and then launched your own law firm, which has grown since then, and you're doing some interesting work. I always think it's just really interesting when people leave Big Law to go to the other side of the V. So, excited to have you on here to share your story.

Randy Gaw: Thanks, Khurram. It’s very nice to meet you and thanks for having me.

Khurram Naik: So let's start with your motivations for launching your firm. You had been at two great law firms, had significant experience doing largely defense-side commercial litigation work. I'm curious about what was the inflection point that said, "Hey, you know what?" Any number of lawyers I think express curiosity in launching their own law firm and any number do. In your case, can you recall any inflection point that said, "You know what? I think this is beyond just an idea, I think this is something that I can really do," and then start to take steps to implement?

Randy Gaw: Yeah, sure. I had an interesting genesis, that's for sure. Part of it was formed by the immediate experience that I had, which is in 2007 through 2008, I was involved in an 11-month trial down in San Diego. I’m normally based out of San Francisco, but I was down in San Diego and I was there for 13 months on an 11-month bench trial, which was, as you might imagine, a lot of hard work and a fantastic experience. But one thing that I observed in my role on that case—and I was one of many senior associates—was that just the way the Big Law firm structure worked, the senior partners, you know, they made the decisions.

In my specific field, litigation and trial work, the senior partners are the ones who are doing all the work at trial. They're the ones who examine the witnesses, who give opening statements, closing arguments, and so on and so forth, right? They're paid the big bucks literally, so that's what they do. Just kind of like game-planning it out years into the future, there wasn't a path that I saw where I would be getting to do similar type work for a long period of time. And that's even assuming that, you know, I was made partner, which of course the odds are pretty difficult in a large law firm. Not only do you have to impress the partnership, but there has to be a business case for you. In my particular field, business litigation, it wasn't like I had any particular specialty or novel set of skills that I could make a case for myself.

So just kind of looking at it all, it was a situation where, well, I don't know if I would make partner, but even if I made partner, I don't know if I would feel fulfilled necessarily for a long period of time because if you do litigation, you want to be in front of a jury. You want to be in front of the judge, getting to make the arguments, getting to examine witnesses and so forth. And that wasn't looking like it would happen to me, at least at the firm that I was with at the time. So I embarked on a period of reflection, thinking about "What is it that I want? How do I go about getting what I want?"

Kind of serendipitously, around that period of time—so we're now in 2009—there were one or two articles written in the local legal media about attorneys like me: Big Law firm lawyers who had ventured off and started their own solo practices or boutique law firms. I read those articles. I knew some of the people who were involved; some of them were my former colleagues. So I reached out to them to kind of gather their thoughts. You know, "What’s your experience been like? Do you find it rewarding?" and so forth. One thing led to another and ultimately I decided to take the plunge, I guess so to speak, and do my own thing.

Khurram Naik: What was it you learned from those former colleagues that helped you wrap your head around how they were approaching their firms and your approach? Like, what was it that you learned that said, "Okay, there's a plan here and I can act on it"?

Randy Gaw: Well, I learned that, one, it's doable, right? So there were all these people who were doing it, who were lawyers first and who had become entrepreneurs out of necessity. It was a kind of intimidating idea for me initially because I didn't consider myself a business person. But to kind of see these people go through with it and to thrive, that was very reassuring. And I think, other than just sort of talking logistics and other things that kind of involve starting a law firm—which I was wholly ignorant about—just hearing all of these people talk about the extreme satisfaction that they felt with the decision that they made.

I mean, these were people who had taken ownership of their careers and were doing what they wanted to do, who were getting their own clients, who were going to court, who were making money. You know, everything that at the time I was thinking, "Is this even possible for me?" These people who had gone ahead and done it ahead of me showed me it is indeed possible and it's something you can actually be good at, despite not having any prior experience in those areas.

Khurram Naik: Did that, in terms of implementing next steps, what takeaways did you have for "Okay, here's the tangible next steps" after you had those conversations? Like, what came next from that?

Randy Gaw: Well, the main next step for me after kind of talking to people and learning from them that it can be done and deciding that this is something that I definitely wanted to pursue was to really more look into the business side of things, like what does it take to open a law firm? I think I spent like the better part of a year just looking into these things. Looking into the difference between a solo practice versus a professional corporation or limited liability partnership. Looking into legal software, cloud software to run the business. Modeling out things like, well, how much do I need to charge? What are my expenses?

I mean, stuff that I think business folks probably would just say, "Oh yeah, that's intuitive, you would do this all the time." But at least for me as a non-business person, it wasn't necessarily intuitive. And so I spent time just kind of learning and reading up about what it is to open a business. What do you have to do? Why should you do X instead of doing Y? There was actually a very helpful book by an author named Carolyn Elefant, I believe that's her name, who had her own solo practice in Washington D.C. She wrote a book, I think it's called Solo by Choice. It was highly recommended by multiple people and I read it and it was just great advice about what it is you need to do, what you need to think about, and why you should go into solo practice if that is what you want to do. So, a lot of research for me, which is kind of very consistent with sort of my approach to the practice of law in the first place.

Khurram Naik: Yeah, okay. So you took this very research-intensive approach, which as you say, I think is very common among experienced litigators. It’s interesting because this theme of a business mindset as being novel just keeps on coming up here. And so then how did you take that leap? How did you say, "I've done enough research, now I have to act"?

Randy Gaw: Well, you just kind of like give yourself a deadline for doing things, right? To force yourself into action. Because inertia is powerful. It's very easy to just keep sliding along and doing what you're doing, but you kind of give yourself a deadline for getting something done and it's very motivating.

In my particular case, I was actually coming on my 10th law school anniversary. I went to Stanford and graduated in 2002. September, I think, 2012 was my 10-year reunion, which I was definitely going towards too. And so it just kind of intuitively made sense: "Hey, I want to have started this by the time of my 10th reunion." And so that was motivating to kind of get things done by then. I actually launched on September 1, 2012.

And in my particular case also, my wife gave birth to our first child in January 2012. And so that actually kind of—originally I was thinking, "Oh, I might want to launch in late 2011," but I kind of realized, "You know, that might be just a little too much on my plate, juggling so many things." The firm that I was with, O'Melveny & Myers, had a very generous paternity policy, so I took advantage of that. They're very good about sort of like getting people time to take time off for children and so forth. So I took advantage of that and then kind of like just gradually sort of worked up to the point of launching in September 2012.

Khurram Naik: You know, I'm struck with that. I also launched my business when my first child was pretty young. I ran this by a very successful lawyer and he said, "You know, really, changes come all at once and so they're really associated with each other and feed into each other." How did you find that? Because that's a hell of a lot on your plate at once. How did you experience that? Do you feel like there was a momentum effect to going through all these changes? What was that like?

Randy Gaw: I’m sure psychologically that had something to do with it, right? I mean, if you're changing like one thing, why not change the other things you've been meaning to do all at once? It's sort of like if you're remodeling—well, just don't remodel like a room; if you want to have all these other changes, assuming you can afford it, do it all at once, get it over with.

For me also, it was recognition that if I waited too long after my kid was born, I would become risk-averse because I have an additional person that I have to now think of; I have to provide think of their future, provide for them, and I might not want to take chances at that point. And so taking the leap now before I had any kind of concrete expectations, before I had settled into something where I need to sustain a certain minimum lifestyle—that was the time to do it, before I scared myself into thinking that it was too late.

And as it turned out, because I didn't have any clients to start—I certainly made no effort to poach firm clients or anything like that, I wanted to kind of do things the right way—the first like couple of months were certainly like extremely slow. Really, it took like a full year to kind of ramp up to full capacity, which gave me the free time to basically spend with my wife and my firstborn. I could leave work early most days and just kind of enjoy the time, enjoy watching him grow. Take advantage of a period probably that I'll never have again in my career where there were very low pressure environments, there were very low expectations, and I could just sort of be. I could just exist without worrying too much.

Khurram Naik: Tell me about what that ramp-up period was like. It took a year to get ramped up. What does "ramped up," by the way, mean? What does that mean?

Randy Gaw: In terms of just being fully occupied with clients such that I had kind of like a full plate of work most days.

Khurram Naik: So did you have an expectation heading into it? September 1st, 2012 start date. Did you have an expectation heading into it for how long it would take to get to that point?

Randy Gaw: No, because I just didn't really know, right? Even the people who had gone ahead and done it before, they had their own unique experiences. Some of them knew clients already or were just kind of like more natural networkers or business developers and so I only knew for myself. I didn't know what to expect. I'd certainly not done any business development of any kind before.

In terms of preparing a business plan, one of the reasons why I felt comfortable going off and doing what I did was because I modeled that I'd saved enough money that I could go two years without literally making any revenue. And so I was like, "Okay, I know I have enough runway to kind of really give this a try for some period of time." And if it completely fails, I can just pick myself up and try to do some where else, go work for another firm, go work for the government. I figured that I'm a talented enough lawyer that I can probably get someone to hire me somewhere. But, you know, so I had no expectations. And the first three to four months, you know, I picked up the odd client here and there, but nothing really big. But then I think I got like an arbitration matter probably two or three months in and that, you know, started taking up some time. Naturally, I just started picking up more and more significant type of work which would be able to occupy me.

Khurram Naik: How did you get these matters? Is this through some effort you were taking? Or just people said, "I'm thinking of Randy, I'm going to send him work"? How did it all happen?

Randy Gaw: Yeah, I'm thinking of Randy and I'm going to send him work. It was all referrals and it, to this day, our firm, I would say like 95% of our cases are referrals. It was nice kind of like launching when I did in September 2012 in that everybody at the reunion that I met, I would talk up about that I'd started my own firm. People were naturally supportive and wanting to help. I made sure to let everybody know that I had started a new firm. I got the word out. And so I was top of mind at that moment. Friends had prospective clients come to them, say "This is something that happened to me," and they sent them my way. The rest is history.

Khurram Naik: And then how did you skill up? I mean, had you had an arbitration before?

Randy Gaw: I mean, certainly as part of a team, right? Like, I worked on those matters for my 10 years at Big Law. But this was my first time being the sole decision maker. Like, before I would either—my job was to execute specific action items or perhaps kind of help formulate strategy. Even as a senior associate, you're kind of helping to think about ideas and whatnot, but I had never been the architect, so to speak, right? It was always someone else's plan that I was following no matter how much I contributed to the overall plans. And now it was on me. I had to think of the strategy, I had to execute it, and it was a brand new kind of challenge. And it was a fun one.

Khurram Naik: How did you bridge that gap?

Randy Gaw: I mean, the only way to do it is to have practice in it and do it repeatedly. And so I did my best in the first arbitration. I got a pretty decent result and I certainly have learned from it to become better at the second arbitration and the third arbitration and the fourth arbitration. Kind of like every case that I handle today, I'm always learning something new. Partly because I'm not in a high-volume type of litigation practice, where we try to handle matters only of a certain amount of value. And so we only work on a certain number of cases at a time. And really, all of them end up being unique learning experiences where you can kind of apply to the next such experience.

Khurram Naik: How did you manage expectations early on? So this is your first arbitration matter. How did you communicate expectations to the client? The client says, "Hey, how many of these have you handled?" and you told them… Or with any of the early clients, how did you communicate or manage expectations around your level of experience and what they could expect?

Randy Gaw: Sure. I mean, first of all, just be transparent, right? The people who hired me for the first arbitration, they knew that I had just started my firm two or three months prior. And in my particular case, I had not been the lead on this thing, but they knew about my very significant experience for 10 years doing arbitrations and trials. In my particular example, I probably had a lot more trial experience than the average Big Law lawyer. I mean, when you have an 11-month trial, then in terms of just sheer quantity, you've had more months at trial than almost anyone at a firm. But you know, I had at least two trials, I think, which is pretty rare in Big Law, and I had multiple arbitrations. And so I was pretty experienced on that front. I definitely knew what I was doing. It was just my first time in the driver's seat, so to speak.

Randy’s reason for leaving BigLaw — wanting to be on his feet in a courtroom — is the same thing that drove Priyanka Timblo to leave Paul Weiss for a five-year-old litigation boutique. She went on to win a $101 million verdict against Walmart.

Khurram Naik: And then you also mentioned a couple different points that, you know, you didn't have a business mindset into this, you thought of yourself as a lawyer first and that you didn't identify then as an entrepreneur. Do you see yourself differently now? Or do you still share those same views?

Randy Gaw: Um, I mean, I've reluctantly come around to the idea that I am an entrepreneur and I have to be entrepreneurial. For the first number of years, I tried to ignore it as much as possible, but you know, that's just the reality. You're running a business, you have to think like a business, and you have to do things like business development and whatnot. But in my heart of hearts, I consider myself a lawyer first. And so I'm happiest working on cases and not trying to think about the business side, so to speak. Which is probably partly why we enjoy doing contingency fee lawsuits so much, because you're not sending out constant bills or worrying about the time you spend and whatever, right? You can just kind of focus on the practice of law and let the business stuff sort itself out. But no, I mean, we are very much now aware of the business of law and doing what we can to operate under reasonable, sensible business principles.

Khurram Naik: What does that business mindset or entrepreneurial mindset change? So somebody who is adopting that approach, how does that impact the work you do and the structure of the firm? What are the implications of taking on a business or entrepreneurial mindset?

Randy Gaw: Hmm, that's a good question. I would say, I mean like one, probably you always have to be thinking about your next source of revenue, right? Like in the sales context, I guess, you always have to be thinking about your next lead. You can't only be working on your existing lead. You have to have the pipeline, I guess as they say. And I think that's an idea that certainly is—I don't want to say foreign—but it's not something which many lawyers are comfortable with. We're probably comfortable just working on our existing work and not having to think about like, "Well, how does the next case come in? Where do we get that next case? Where do we get the next client?" And that's sort of, at least for us, a transition where we now are always thinking about "Well, where is that next case?" in addition to, as we're working on the existing cases. And it's a little challenging because litigation doesn't tend to have too many repeat players, at least for us. We don't have too many repeat players, so we have to really think strategically about where can we get future clients and especially the clients that we want to get. What can we do to make it easier for future clients to either find us or to be comfortable with us or to seek us out?

Khurram Naik: And what's your answer to that question today?

Randy Gaw: One, we're still trying to figure it out, right? But I would say one thing that at least I think has been effective for others that I've seen is getting people to understand that you're out there, who you are, that you're out there doing the work and that you're getting good results, right? I think there are certainly many people who are kind of not comfortable with what might be considered self-promotion, but call it what you will, it is very effective for getting people to realize that you are out there or to getting you on top of mind for the people that you do know. And I suppose it just really has to do with how you present yourself, right? If you're presenting yourself in an authentic manner, then it's less self-promotion and really more just kind of like keeping people abreast of what it is you do and why you're a good fit for people out there.

Khurram Naik: You know, I think you're doing a really good job with that. I think that's a key part of why I was drawn to your story and saying "Hey, you know, without being very ham-handed on it, when you talk about some of the plans you're taking in these class action cases and some of the companies that you're suing and the counsel that you're representing them, it's you know, it's a light version of David versus Goliath. And so that's a classic story for a reason, and so those storytelling principles are effective that you're not gloating or going on and on about how amazing you are, but just simple narratives I think that do draw people in and say, "Hey yeah, this is a skilled lawyer taking on an interesting case," and I think that's a compelling story that itself is a compelling story that people are drawn to.

Randy Gaw: Oh thank you. I mean, I'm glad that you think so. It shows that at least I'm doing something right on that field. But also, I mean, it's good practice for what it is that I'm doing. Not the marketing part, but the fact that we're in litigation, we do trials, you're telling stories about trials. And if you're unable to tell your own story effectively, how can you expect to tell someone else's story effectively, right? You have to be the best at telling your own story. And so certainly whatever it is that I'm doing where I'm trying to educate people on what it is that I've done or give people updates as to how our firm has accomplished this or what, or even like failed at something, right? Like I'm pretty open about talking about setbacks that we have. It’s also exercising kind of like the storytelling muscles that we have. You don't get better at something unless you practice it repeatedly. And practice can kind of come in all sorts of different forms that you don't even necessarily think of as practice. You know, like that movie The Karate Kid, right, where the guy is washing a car and not realizing that that is actually kind of developing muscle memory and certain skills that translate into the various karate moves that he ends up executing later in the movie.

Khurram Naik: That's a great Karate Kid reference. I'm so glad we got into that. Every podcast episode should have a Karate Kid reference.

Randy Gaw: Great movie.

Khurram Naik: So okay, so early on, unless you're able—you said, "Hey, I can finance my law firm for two years." That would be a very aggressive timetable for contingency work, let's say class action work. So then what was the transition from billable work to contingency work? What was the draw to that and then how did you know that you're ready to do that in terms of the business of it, in terms of the substantive work? Tell me about that transition to taking on contingency work.

Randy Gaw: Sure. So we took on our first contingency case in 2014. So I basically went a year and a half or so doing only hourly work. And truth be told, I did not envision myself doing contingency work at the time I started my firm. Probably because I was still—I was entrepreneurial enough to start my own firm, but I was like, "Wait a minute, hold on, I don't get paid unless I collect? That might be a bridge too far." But it kind of came about in 2014 in our first case, and we had met a client who had a great case, had been paying hourly for his current attorneys and was not getting a very effective result by them and basically had run out of money. And I remember, a friend of mine at another firm, he found this client somehow. He introduced me to that person and kind of said, "You know, would you be willing to join me in working on contingency?" And so it was like back then, it wasn't something I expressly proposed, it was my friend who kind of proposed it out of necessity because this client couldn't afford hourly attorneys.

Thinking about it, it was like, well, A: the risk is mitigated somewhat because, you know, my friend's firm was also doing it, right? So it wouldn't be us just shouldering the burden, we'd be working together on this contingency case. And two, it was a client who really couldn't afford hourly rates anymore, and so it was like a binary question of: "Do we just take… we can't have this client otherwise, right?" So it's like, is this a good case or is this not a good case? And so if this is a good case, why wouldn't we take it? Because ultimately if you think that you can do a good job and if you know the defendant is in the position to pay, you know, one way or the other, this is an opportunity.

And that first case kind of made me realize that there was a market for contingency cases in the business litigation standpoint because a lot of firms wouldn't even consider it, right? Like their business model just says "No, we don't do any contingency work at all" or we do very limited contingency work. And this client was considering us solely, really, because no other firm that they approached was willing to do it on a contingency. So I kind of realized, "Well, hey, there's less competition in the business litigation world if you're willing to do cases on a contingency fee basis. And if you're confident in your own skills, you will probably be rewarded for doing so, and rewarded well." Like we ended up getting a good result on that case and it was, you know, our cut of it of this resulting settlement was definitely much higher than what our hourly rate at the time was. And that kind of like led on to taking that on as a business model.

Khurram Naik: And so do you have a target, like how do you identify how much contingency work you should be doing, how much hourly work you should be doing? How do you identify that mix?

Randy Gaw: I would say in an ideal world we're 50/50, you know, up to maybe 33% hourly, 66% contingency.

Khurram Naik: Is that based on time put in or revenue?

Randy’s narrative-first approach to trial — asking “What story will we tell?” before anything else — aligns with Joe Ahmad’s philosophy that juries are “phony detectors” who respond to authenticity over polish.

Randy Gaw: Time put in. So in an ideal world, you know, where 50/50 but, you know, certainly 1/3 hourly, 2/3 contingency we have done many times. We've probably gone over 2/3 contingency. That is kind of like I said in an ideal world. It's not a rule at our firm because the reality is if there are really, really high-quality contingency cases and they just came in one right after the other, we're going to take them and we'll find a way to pay for it or make it work, right? Like we're debt-free and my partner and I have certainly invested a lot of money into contingency cases. And it's just a good investment, you know? It's sort of like if you're a venture capital fund, you don't turn down future investments just because you've already deployed funds. It's like if this is something that hits all of your checklists and you realize that you're going to get a high probability of getting a really good result, you take it on, you know? Like we're in the risk business, so take risks.

Khurram Naik: How did you identify that ratio as being ideal for you?

Randy Gaw: I mean, just because it's always nice to have monthly revenue come in on an hourly basis, right? It's nice to know that you're making payroll without any problems, you know, that you pay rent without any problems. And frankly, those are pretty low cost relatively speaking in running a firm. In a contingency firm, the big costs are paying for the contingency cases, right? The experts cost a lot of money. Electronic discovery costs a lot of money. So really it's kind of like keeping the lights on so that you can pay for all of this stuff. Especially since under tax rules, contingency case expenses aren't deductible as business expenses, right? They go on your balance sheet. And so really you're using your after-tax dollars to pay for these contingency cases. Having at least 1/3 of your cases be hourly cases, that covers your contingency costs, which are high. Like currently, you know, my partner and I are out, I don't know, 1.2 million or something out of pocket or something on contingency cases, so you gotta be making enough hourly and other contingency cases to pay for all of that.

Khurram Naik: Have you used funding in the past?

Randy Gaw: We have, regretfully.

Khurram Naik: What made it regretful?

Randy Gaw: The high interest rates, sure. You know, it's something actually I mentioned on LinkedIn. We took funding and the interest rate was between 20 to 30% annually. And how they pitch it to you is: "Well, it’s non-recourse, right? So you don't have to worry about paying us back if you don't hit." Which is like, "Okay." So you kind of think about it and you're like, "Well yeah, okay, they deserve a 20% or 25% interest rate since they're shouldering all that risk." But then, you know, we eventually did hit and then we paid them out a lot of money because of that interest and just kind of I realized, "Like wait a minute, why was I so worried about it not hitting in the first place? If I'm worried about the case not hitting the first place, I shouldn't be taking it on contingency in the first place, right?" I mean, you're taking it on because you are very confident that you're going to get a good result, knowing of course sometimes things happen and you don't. But if you're confident that you're going to get a good result then don't "de-risk" by giving away a very substantial part of your upside. When you de-risk, do it on a more appropriate level. And so that kind of changed, those experiences kind of changed at least my mindset about taking funding. Like funding is really only for those cases where you can't even take it on in the first place unless you have the capital provided to you by funding. So then in that case, funding makes the case possible. But if you're taking on a case if you already have the ability to self-finance a case then just believe in yourself, you know? Take your own risk. You save so much money, like an unbelievable amount of money, because 20 to 30% every year really adds up, obviously.

Khurram Naik: To your point about taking on marginal cases to the extent that you can, like in the analogy of a VC, a VC might say "Hey, this option is too good to pass up, let's go to our LPs and get some additional capital to invest." So you're saying by way of analogy, your goal is to self-fund a plate of cases that you identify and then to the extent that you know—it sounds to me that to the extent there is an additional case that is too good to pass up but you can't finance it on your own, that's a scenario where you think funding would be helpful.

Randy Gaw: For us, yeah.

Khurram Naik: And so yeah, I get your premise about adverse selection where to the extent that you're leaning on somebody else for financing… Like say in the context of people, a personal residence. Any number of people might… Buying a personal residence is in the eyes of many a financial decision, sometimes people perceive it to be purely a decision about consumption. But you can definitely make the case that the existence of mortgages, subsidized mortgages, whatever, make it easier to spring for larger prices because, "Hey, you know, just someone else is throwing money at this too." But so I wonder how you think about adverse selection in the context of case selection to begin with, because when you said earlier, "Hey, this company had gone to several other firms and nobody chose to take them on contingency," there's two ways to interpret that: one is "Hey, there's not a lot of competition for this and so this plays into our strengths because we're lean and efficient so we can take this on." and another interpretation is "Hey, this is a dog of a case," right? Now how do you… So it seems to me there's potential for adverse selection even in taking on those cases to begin with. So what is your vetting criteria to mitigate the risk of adverse selection at that stage?

Randy Gaw: Sure. Well, I mean, you definitely take into account if someone had passed on this case who does contingency work, right? And at least in our case, a lot of times when cases come our way it’s been passed on by people who do hourly cases as opposed to contingency cases, so we don't necessarily have another contingency firm's feedback as to why they chose to take or not take a case. But, you know, definitely if you know that a comparable law firm has passed on this case, you ask yourself questions and you vet it a lot more carefully as to whether or not it makes sense for you to take on this case. And sometimes we reach a similar conclusion as the other law firm and sometimes we don't because, you know, we have a certain view of things, we have a certain view of our skills and we feel like we can get a better result perhaps than what the other firm did or maybe the other firm is just better at making decisions than us. Ultimately, it could be both or or neither.

Khurram Naik: Yeah, right. I mean the thing about legal work is, of course, the reason why we're compensated—I mean you were talking earlier about this litigation funder they're to be charging 20 to 30% whatever interest rate is because you're taking on this risk and so too with lawyers. The risk comes from ambiguity, right? You don't know what the outcome is. If you had certainty around the outcome, then it would cost a lot less to finance it, right? And so yeah, legal work product I think so much about understanding the business of law flows from understanding particularly in litigation that litigation is inherently unpredictable. That's how… if litigation was predictable it'd be some other thing other than the nature that it is right now. That's the essence of litigation work is that it's largely unpredictable and of course your goal is to do things to make it as predictable as possible but just you can never abstract away that risk. And so yeah, I think that makes sense that in the context of investing, any number of times you have one very successful investor taking a large equity stake in a company while another one is exiting. They just have different theses on the nature of that opportunity and they potentially can both be right depending on their time horizon. That also plays into your comment on being able to finance these cases, maybe it doesn't make sense in the short term but maybe it makes sense in the long term.

Randy Gaw: Yeah, and I mean, a lot of firms I think who consider maybe have passed on the cases that we've taken on, I don't know necessarily what their evaluation criteria is or if they're a larger firm they can't afford to take on a miss, whereas us being a smaller firm, you know, we have fewer mouths to feed and so we can be more aggressive in taking on a risky case, you know, compared to them. And then frankly sometimes there are people who I just think are less creative than we are. Because, you know, a lot of kind of a success in the law, in litigation, comes from edge cases. And sometimes there are people who are just a little too conventional thinking about the law or applying the law to the specific facts, and they don't realize that, you know what, there is an interesting edge case that you can make out of this and you have an avenue for success. So there are definitely people who are I think a little too rigid with their analysis and sometimes we're the beneficiaries of that because we're willing to kind of like think of multiple angles in order to pursue a particular path to success for our clients. I'm actually thinking of this one case that we did as a class action and the client had gone to multiple law firms, some really big law firms, and absolutely none of them were willing to take it on contingency because their kind of very traditional analysis just didn't, you know, have like a strong… I guess they didn't see it as the strongest claim or something. I don't know. All I know is kind of reviewing their emails afterwards when we collected our client's emails and filter them out for privilege and all that stuff, you kind of look at what they were saying to other law firms and what they were telling them, like "Oh, that's interesting." But, you know, we had approached it from a somewhat different angle and we were ultimately successful and validated in that approach. We got class certified, we got a class action settlement, you know, we did well financially and so it's like we're kind of rewarded for our ability to identify kind of new angles and our willingness to take them.

Khurram Naik: Can you give us some more inside baseball, like what was the legal theory or what did you identify that was—you used the phrase "edge case"—what was it that you identified that previous counsel didn't?

Randy Gaw: I mean, I don't remember the specifics exactly, and some of it is still a lot of it is confidential attorney-client privilege. But the kind of gist of it is there was a contract between the parties and people just kind of like looked at the contract and said, "Well under this contract you can do this or you can do X or you can't do this." There are things that say you can't recover for this, so therefore you can't recover for this. And we kind of did a more holistic approach and it was like, well, what were they saying? What was the defendant saying contemporaneously at the time they entered this contract? What did they say after that? Is this language ambiguous? Are there certain industry norms or standards that apply here that people understand that help interpret what this means? Things like that, you know. And so we were able to survive motions to dismiss, we were able to get class certification and ultimately kind of present like a viable case. At the end of the day, we don't know if we would have won or lost at trial, although we were actually pretty confident, but we found we were willing to kind of challenge conventional thinking and in that particular example we were rewarded.

Khurram Naik: I wonder if the ability to be more creative comes from taking on fewer cases, having more space and just being able to think more about fewer cases. Like can you speak to where that creativity comes from? Because I imagine some of these other people at the firms in the past there's any number of comparably skilled litigators maybe with similar experience to you but maybe the conditions of the pressure they face at those firms are such that they or you know, they have more matters or they're stretched thin, however you want to put it. What do you attribute to why you're able to, for somebody who is comparably skilled to you as a litigator, why you're able to apply this or generate this creativity?

Randy Gaw: I mean, I think you identified one of those reasons, right? We have more time or we're able to allocate more time into thinking about these cases at the prospect stage. So that's certainly one of it. Other than that, all I can say is part of it is a kind of inherent judgment ability by lawyers, right? Some lawyers are able to think out of the box a little better than other lawyers, but in return they have like probably worse skill sets in other areas compared to those other lawyers. Like I would just say my partner and I, Mark, we just happen to be pretty good about thinking creatively and doing kind of like doing the basic law school stuff. It’s like, "You know, what is the basic principle of law here? How do the facts fit in this principle and how can you… if you kind of know what the correct—like correct in the sense of like: what is the just outcome? Is there a wrong that is in search of a remedy?" Well, then you kind of think, "Well, there are, you know, the law usually tries to find a way to remedy wrongs." And so you kind of just look with that approach to seeing what other ways you can pursue this to get the remedy that the client deserves.

Khurram Naik: How often are you able to identify or can you give examples of a time when a client thought there was a certain wrong and actually there was a much more significant wrong?

Randy Gaw: That's a good one. I would say it probably at least in my experience happens more in the sense that when you kind of dive into the facts of this case you probably realize that the scope or scale of the wrong being occurred is much greater than what you had thought as opposed to kind of like discovering a whole discrete different wrong that had taken place. I’m sure it has happened, I just can't necessarily think of an example sitting here right now.

Khurram Naik: Can you talk some more about, you know, earlier in when you're building out the firm, you're taking the work that you can get and then over time you start to get more work. So I think there's two aspects of that I'm interested in: is case selection in terms of how you choose to niche? So we talked some about billable versus contingency. I'm interested also in practice areas. Like, how do you choose areas of law that you're saying, "Hey, let's focus on"? I guess we'll start with that and then I'll kind of work in the other jumping-off points.

The boutique model Randy describes — flexible, no traditional billable hour pressure — is one Rakesh Kilaru also embraced at Wilkinson Stekloff, where the firm eliminated billable hours entirely.

Randy Gaw: Sure. Areas of law. So I sometimes have to jokingly tell people when they ask me what kind of litigation do I do and I say, "Well, I do opportunistic litigation." And so if there's a case that comes across my radar and if I think that either it's interesting or lucrative and that we won't end up committing malpractice if we take the case, then, you know, we'll try to pitch for that particular kind of work. You know, one of the benefits of being a small law firm is that you have the flexibility to do that sort of thing. You just need the owners to agree, "Yeah, let's see if we can take on this kind of work."

But you know, to kind of give a more serious answer to your question, I think ultimately for us the areas of practice that we focus on are influenced by: one, can you make a good living off of that? Right? Because we want to do high-margin work, not low-margin work. And two, is this something that kind of is intellectually stimulating for us? Which is not a requirement for any case, of course, but it certainly kind of we're more willing to kind of go beyond our boundaries if it's a case that we think is interesting. And you know, also third, is this a case where we feel like we're helping people as opposed to not helping people? And that's not a requirement either, but again it kind of makes for an edge case for us. It’s like, "You know what, we want to kind of expand beyond kind of our personal comfort zone if we feel like we're in a position to help people." So there are definitely cases that we've taken on in the past that we normally don't handle because one of us felt, "Yeah, you know, we kind of feel sorry for these people, so let's see if we can help them out."

Khurram Naik: Helping people versus not helping people… you just mean like people who have a particularly sympathetic cause that may not be financially rewarding?

Randy Gaw: Yeah, well, you know, yes. We don't gratuitously do like, you know, low-margin work. So, you know, we certainly when we're taking on a case we want to make sure like, "Hey, it has at least the prospect of making money for us." But you know, we certainly recognize there are some cases that are unlikely to be particularly rewarding, you know, maybe we'll break even, but we still do it because we think we're in a position to help somebody and others won't do as good a job or are unwilling to do a job. But you know, I don't want to make it seem like we're these crusaders out there. For example, we don't deal in immigration law or civil rights or things of that sort because that's just not our background, that's not our skill set and there are a lot of other people doing like really good work in this field. And as much as sympathetic as we might be, we're just it's too much for us to like learn like this whole area of law or other sets of procedures potentially that we just don't know anything about. But within the kind of realm of work that we do, we will sometimes go out of our comfort zone if we feel we're in a position to help people.

Khurram Naik: How should boutiques think about opportunistic versus strategic, niche versus diversification?

Randy Gaw: I think every owner has to decide for themselves, really, because it kind of goes back as to what it is they want to get out of owning their own law firm. Is it just about like making as much money as they reasonably can? Or not? Because the decisions are different, right? Like if you wanted to maximize your revenue, you probably are better off just kind of really specializing in one or two, holding yourself out as an expert in one or two areas and relentlessly marketing that and not getting distracted with other stuff. Which is, by the way, perfectly valid. I think there are people who are doing a great job of that and I admire them very much. But if your kind of goal is to also just sort of keep yourself intellectually stimulated about something, the work that you do, then your decision-making calculus is different. It's not just "Oh, am I making enough money from this?" It's like "Is this an area of law that I'm doing that can actually keep my creative juices flowing for one reason or another?"

And I'll just use our firm as an example. We obviously do business litigation; that's bread and butter, like every—most civil litigation firms do business litigation, right? Like that keeps the lights on and it can certainly be very interesting in its own right. We take on, we selectively take on personal injury cases, catastrophic injury cases, that are high value. And we take them on partly because, I mean even though the law's not particularly complex in those areas, they have like really interesting human stories. And so working on those cases kind of goes back to almost like when you're in law school in the first place, like thinking "Why do I want to become a lawyer?" Well, you know, this person was injured because of the wrongful conduct of another person and I'm in a position to tell their story and to help them get some justice for the ills that have befallen them. So personal injury kind of satisfies the interesting facts component. And then we also do antitrust work. We have a particular expertise in this real niche area called the Robinson-Patman Act; it's the federal price discrimination. And that kind of is an intellectual exercise for us because it is an area of law that involves a lot of economics, for example. It involves like the application of some very esoteric laws regarding that particular statute. And that's intellectually interesting, just kind of dealing with sort of these almost policy-type arguments in the law and keeps things kind of interesting for us. And it can certainly pay well too if you know what you're doing. So it kind of checks off all the boxes for us.

Khurram Naik: Yeah, it's really interesting to identify these different practice areas not by necessarily the economics of them or from any anything structural to that area. Privacy is just there's no reason to think privacy is going in any direction but becoming more important and higher stakes. But it's interesting to talk in terms of motivations and personal motivations and the feel that you get from these different practice areas. I think that's a very interesting lens to choose work.

Randy Gaw: Yeah, I mean one could say it's a way we choose work, one could say it's a way that work is chosen for us, right? Like if you're kind of just getting solicitations for certain types of work, it's low-hanging fruit and so you're kind of like, "Okay, well let's like really look into these kinds of cases more and more," and you kind of maybe unintentionally develop an expertise in them and it becomes self-reinforcing at a point, I suppose.

Khurram Naik: So yeah, I think that motivation sounds like an important criteria. But like heading into a year, I mean, going back to this business/entrepreneur mindset, how do you plan ahead for the year? What are your time horizons for your goals? How do you define goals for your firm?

Randy Gaw: We're not huge into concrete goal setting and perhaps we should be; we're still very much learning about optimizing the business of law. But I would say for us, we just more have abstract ideas of, you know, okay, we're working on like these nine cases, right? So the goal for this next year is to "How do we get good results in those types of cases?" Like what do we do, how do we set up ourselves to get the best possible result in those cases?

But then beyond that, the next case that I mentioned earlier: where are we getting our next cases from? Our goals are probably be more loosely abstracted to "What cases do we want to get in the future? What do we do to position ourselves to try to get those cases? How do we get cases like that of higher value as opposed to lower value?" Like do we need to go out and talk to people more in order to do that? Do we need to maximize our results in these other cases and publicize that in order to achieve this outcome? So we're kind of like thinking about our goals, the only kind of goals that our firm has as typically speaking is "What can we do to maximize our opportunities to get the kinds of cases that we want to work on?" because we don't set goals in terms of head count, we don't set goals in terms of revenue or whatever. Like that stuff works itself out. We just set goals on what kind of work we want to get and how do we get it.

Khurram Naik: If you execute on the ideas and the work that you're doing now, how will your firm be different two years from now?

Randy Gaw: Well, probably a little bit bigger. Like if we successfully do what everything that we want to do, then naturally we'll get bigger and bigger cases to work on, which means that we have to get more and more people to work on them. And then kind of like there's a positive feedback loop in that you're getting even bigger and more interesting cases to work on, which means you have to get even more people to work on those cases and so forth. And so that's why I say like the revenue and head count thing, you know, all that stuff, it works itself out. If you're doing what you want to be doing, you'll naturally make more money, you'll naturally have more people because you need the more people to make the more money in the first place.

Khurram Naik: And when you picture having more people to work on those cases, what will be different about the cases that you're doing? Is there something specific that you can picture as an expectation for the mix of work you'd be doing, the stakes of the cases?

Randy Gaw: I would say, so on the business litigation side, it would be… we're kind of pretty consistently working on seven-figure, eight-figure type cases, and it would be getting to the nine-figure level, right? Consistently working on nine-figure cases, whether that's 1v1 or a class action type cases. In the Robinson-Patman Act field, similar thing: like we are typically working on high seven-figure, low eight-figure type cases. Going to mid eight-figure type cases, maybe even like high eight-figure type cases in this particular world. Or taking on really, really big targets in this particular field. So far, the people that we've sued have largely been manufacturers of well-known products, but they're not necessarily the products that every household has. And so kind of going on to the next step would be those defendants that are making the products that every household has.

Randy’s evolution into LinkedIn storytelling as a business development tool is exactly what Sunny Kim teaches. She helps lawyers build authentic personal brands and turn existing content into trust-building posts.

In the personal injury context, it's like the types of cases where there is just some massive harm that was perpetuated on a large group of people and you're getting redress for that all at once as opposed to a 1v1 type of harm. Although I will say in the personal injury field, I don't think we ever necessarily want to get into the mass tort field or something that involves like multi-district litigation, MDLs. That's a level of administrative complexity that I don't know if we necessarily want to deal with since we just sort of do this stuff on the side. But for the other two cases, that's certainly what I could set out as goals and visions for the next five to ten years.

Khurram Naik: And you've talked about the skill of identifying interesting fact patterns and then the role that motivation has for you for finding work that's compelling that way, then also the importance of storytelling—that’s a recurring theme. Can you talk some more about storytelling in your trial work? How have you developed the principles of storytelling that you use? Are there recurring principles? Is there a technique, a formula, a process that you use for arriving at effective storytelling?

Randy Gaw: Sure. I mean, when you get to trials, that's all about telling a story. There's the story that the plaintiff has to tell about how the plaintiff was wronged by the defendant and then the defendant's story is like, "No, you're not hearing the whole truth, this is the real story." And so when you're at that point, it is incumbent upon you to figure out a way to present your story as cogently, as compassionately as possible so that the jury wants to go for your client instead of the other client. Trial is about motivating the jury into wanting to support your side as opposed to the other side. Because that ultimately colors how they view the law and how they view the facts. Because if they want to go for your client, when they're looking at a set of facts, they'll be interpreting it in the light that's favorable to your client as opposed to the light that's favorable to the other side's client.

So I think effectively telling the story is… at least how we would go about doing it is done through one of certain ways. One, at the very start of the case, you kind of need to have a sense of what the story is. We as lawyers are trained as to like legal analysis; we're like, "Okay, so this is the cause of action or this is the affirmative defense," which is all great, but you have to kind of go beyond that and just say, "What is the core narrative that is driving this story? What do I want the decision maker to be thinking about when the time comes for them to make the decision?" And at least for us when we analyze a case—unless it's strictly a numbers-based kind of thing, which sometimes happens like when you have a claims that just involve accounting or whatever—at the end of the day when we are taking on a case, we have in mind there is this story to be told, this is what we want people to know.

And when you kind of have figured out like the story to be told—which by the way is kind of what helps us decide whether to take a case on contingency or not—because if you're thinking, "Oh man, this is a terrible narrative for a jury, the jury is not going to like our client even if the law may be on their side," that definitely cautions you about taking the case. When you kind of have in your mind what the ultimate narrative is, then you start thinking, "Well, what do I need to do? What do I need to develop both on the legal and the factual side so that I can tell this story at trial?" And so kind of like when you're thinking of that story at the very inception of the case, that drives your strategic decision making for the rest of this case: what you choose to pursue, what you choose not to pursue, why you're bringing this claim and not that claim. And so kind of like when you have like this end goal in sight, it helps you make decisions as to what to do in the first place.

And then also, I do not pretend that we know everything about everything, especially storytelling. There are some very good experts out there who are much better at telling stories than we are, and because we know there are other people out there who can do it, we get their help too. Jury consultants, for example. We go to trial once or twice a year on average, which is kind of a lot for a firm that does sophisticated commercial litigation. But a jury consultant is going to trial like 20 times a year, more, and they've done it for decades. They know all the stories out there, they know everything that resonates. So at least what we typically do is as we're getting close to kind of like the jury trial phase, we hire the jury consultant and say, "This is what our case is about, what do you think? What should we pursue? What resonates most with the jury?" and we get great insights from the people who are in the business of predicting what juries like and don't like. And that usually helps us hone the message quite effectively.

Khurram Naik: When you say "what you pursue," what do you mean by that?

Randy Gaw: I didn't mean that in terms of the jury consultant; it was just more at our stage, early stage, when we kind of envision the narrative. You may choose to make certain claims and not make certain claims because you realize it's inconsistent with your narrative.

Khurram Naik: Have you ever taken a claims-first approach, a legal issue-first approach over a storytelling-first approach?

Randy Gaw: Sure, because some cases don't involve particularly sophisticated themes. And so you have a narrative, but the narrative is like, "Well, you have a contract and this person breached." Like it's clear-cut: there is a contract, service was supposed to be provided or good was supposed to be provided, they didn't do it. This is not one where you're going to be searching long and hard for like particular narratives and themes at trial, so certainly you kind of go for a claims-first approach.

And then when you're on the defense side, sometimes you do do a claims-first approach because if you feel like this case has severe deficiencies, you can knock it out before it gets to a jury. Then yeah, you absolutely analyze it from a technical perspective because your job is to make sure it never gets to the jury.

Khurram Naik: Yeah, that makes sense. Would you think all things considered contract disputes are more amenable to a legal approach as opposed to say tort claims, which are much more amenable to storytelling?

Randy Gaw: But tort claims sometimes frankly are the easiest to go from a simple claims perspective. If there's clear negligence or clear wrongdoing and someone was harmed, the claims write the narrative almost—like you don't have to deep-dig into those. We had recently a claim where we handled the unfortunate case of a woman who died because her fertility doctors gave her the wrong medication and clearly breached standards of care in doing so. It was like an awful story. We had a great narrative for it—like our complaint and our mediation brief especially—the mediation brief was like, you can move someone to tears from it. But, you know, I don't want to pretend that that was what caused it. It was just like, "Look, that's just a simple legal claim issue. There's clear negligence, there's clear harm." And we—any number of other lawyers probably could have gotten the exact same result as us. I'm underselling our capabilities there because sometimes the harm is so clear and sometimes the legal claims are so clear that it's kind of silly to argue that one law firm's skill is going to get a materially different result. All I can tell prospective clients is how we would approach this case, how we would work it up, how I would personally give my personal attention to this as opposed to delegating it off to somebody else. And you decide for yourself whether that appeals to you or doesn't appeal to you. Because sometimes the facts are so compelling that it's just a question of whether the client works better with one approach as opposed to another approach, as opposed to any inherent skill by a lawyer.

Khurram Naik: Yeah, and I have come to appreciate in my work and the work of other skilled professionals is that there is plenty of room for skill and plenty of room for personal preference because, again, much of any kind of white-collar work is inherently ambiguous and so there's many potential paths to success and different approaches that resonate with some people over others. Having factored that in for looking at comparably skilled litigators maybe in boutiques, maybe with comparable experience as you have, what do you think does differentiate your approach over a comparably skilled peer?

Randy Gaw: I would say just at least based on my personal experience, we're a little unique in that, like I said, we look at the narrative first. We look at the end result, we kind of how we look at it is: what will it be like to be at trial? Is this a case that we can win at trial? Is this a case we want to take to trial? Is this a case we're comfortable taking to trial? And so I would say we kind of look—we have a further time horizon in terms of evaluating the case and presenting it. And I would say also another thing that differentiates us is that we tend to kind of present matters to the client in terms of strategy with framing and with long-term goals in mind as opposed to, "Well, what's the next step? What's the next step? What's the next step?" You know, sometimes when you're in litigation, you're literally just kind of working on the next procedural step and you don't think too much further beyond that. But we tend to try to like predict, "Well, this is what we think will happen and so we do this and then that leads to this and that leads to that and then they're going to do this and that leads to that," and so on and so forth. And so we're just trying to map things out as much as possible and make sure that the client is kind of informed and aligned with us every step of the way.

Khurram Naik: I talk to people who use ideas from different disciplines. I was at a conference recently and a keynote speaker was formerly a consultant who's very successful then got really into chess, studied it for a couple years and now applies ideas from chess strategy for coaching as an executive coach for sports teams. I had Tim Yu of Bird Marella on the podcast and so he talked about his love of professional wrestling and the ideas that he's learned from there about storytelling. So there's different disciplines that we can draw on for our work. Are there disciplines that come to mind or principles or that you draw on into your work?

Randy Gaw: I like that question because for whatever reason I've been reading a fair amount of opinion pieces and thought pieces about, "Well, I really like X and that have helped me practice law for the following reasons." It's always interesting to hear all this stuff. I would say like first I'll give a global answer: it's like whatever works for people, whatever works, right? It's like ultimately my kind of takeaway from it is if you are passionate about something, you can always find an application of your passion to make yourself better at whatever it is you do. It could be a better parent, to be a better lawyer, to be a better whatever. Because there is something that we always can learn from doing something and we can apply to other things. Because there are principles that are universal, like there are ways of dealing with unfavorable outcomes or favorable outcomes in one activity that we can apply to others because it's like the process of coming to understand, coming to coming to accept certain outcomes or the your learning what your decision-making process is that helps you realize I can apply that to other activities to help drive a better outcome.

I haven't read the or heard the anecdote about professional wrestling, but you know, I'm sure it works for this individual in a really good manner. For me, there is nothing in particular that I could honestly say I referenced this or I derived my personal experience from that to help me become a better lawyer. I would just say there is a lot of things that I just try to take from what I do in my kind of day-to-day life or in if I'm just doing something for fun that I realize has application to my job. For example, going to school and talking to other parents, very mundane stuff, right? All of us do it. A lot of the other parents at school are not lawyers; they have no idea what it is that we do other than some mythsized version of what they see on TV. How does that help me? It's my storytelling exercise. It's my storytelling muscles. Like, I have to take a complex idea and reduce it to a level where people can understand but also want to understand more. Like people want to have follow-up questions and engage and do it a way that's not condescending to other people, to explain it to them with respect, with sincerity, with authenticity, and get their interest, get them wanting to learn more.

I love playing poker, Texas Hold'em. That's kind of like the quintessential litigator's kind of practice because you're anticipating what people are doing. You're trying to model out outcomes and probabilities. You're trying to bluff. You're trying to calculate the best kind of value proposition for yourself: "Well if I take this action, what's going to happen here?" And you have to come to grips with disappointment, knowing that sometimes you have your decision-making process was correct and you get outcome a bad outcome, sometimes a really bad outcome. And then you just have to pick yourself up and realize that, you know what, sometimes these things happen and you can only learn from the experience and figure out whether there's anything you could do better. And if you conclude you did most of the things correct or you couldn't do anything better, then have the conviction to do it again because you have to have confidence in yourself that ultimately you do this long enough, you will get the right outcome most of the time because you're following the right process. And at the same time if you sometimes luck into winning a hand, you play it horribly but you get like a huge jackpot through sheer luck, having the humility to recognize that that was because of luck and you realize "I need to improve in this and this and this and this so that I'm not in a position again where I need blind luck to bail me out." In trials, there have been times where we've done everything that we thought we could have done and we didn't get the result we wanted but, you know, you just have to like say, "Well, we got to do this again because we know this was the right process." And then there are times where we got a result and it's like, "Oh, you know, this we didn't necessarily anticipate this and so we probably need to figure out how can we do a better job of anticipating this in the future or what can we do to kind of exploit this particular kind of tendency or predilection by the jury." Learning from it and adapting so that the next time we're better positioned.

Khurram Naik: Let's take somebody who is a commercial litigator, 10 years experience in Big Law, has quality substantial experience, someone in a similar situation to you at the time that you left your firm. What counsel do you have for that person for how to think about the decision to open a firm and an approach?

Randy Gaw: Do you want to be the decision-maker or not? If you want to be the decision-maker, then make it happen. Just do the research, all of us can do the research, talk to people, educate yourself, but then make sure you find reasons to go forward as opposed to reasons to not do it. Because ultimately if you want to be the person who drives decisions, who architects litigation strategy from start to finish, who's the one who tells a client "I think we should do X and not Y," the one who's giving the opening statements or the closing arguments at trial, then yeah, start your own firm because for most people in Big Law—not all people, but for most people—that will accelerate your ability to become the person who makes the decisions as opposed to having to wait your turn. But if you do not want to be the person making those calls, then don't do it because starting your own firm is not conducive to your skill set, to your mindset, and you're not putting yourself in the position to succeed. We have to have an honest conversation with ourselves: what am I good at, what do I want to do? And there are some people who are—will I think find that they are very happy not being in the driver's seat. They're very happy being the second chair, they're very happy executing someone else's stuff and that's great. I think that's a great career and there are people who are very fulfilled and do an excellent job at that. And there are times where when I see the profits per partner metrics of these Big Law firms, I’m like, "You know, to be a service partner at some of these firms doesn't sound so bad at all!" You just sit down and do the work and have fun. But yeah, you just need to have an honest conversation with yourself as to what you want and what you're capable of doing.

Khurram Naik: Well Randy, thanks for sharing your experiences. It’s really interesting to hear some of the recurring themes around particularly around motivation and how you've really reverse-engineered work that you find motivating. I think that's—I don't know a lot of people thinking about work in those terms, so I think that's a really helpful additional lens on work. And so thanks for taking the time to sit down and share your story.

Randy Gaw: Appreciate it, Khurram. Very happy that I was able to talk about some of these issues.

As a partner at HWG who specializes in legal ethics and malpractice, Hilary sees patterns most lawyers never notice: the junior partner who takes firm templates because they're terrified they can't succeed without them, the equity partner who solicits clients early because they fear losing portability, the associate who stops billing time before giving notice because they feel the firm treated them unjustly. In this conversation, Hilary breaks down why 90% of clients fall into two buckets (they're either coming with you or they're not—and timing rarely matters), why confidence is the underrated trait of successful rainmakers, and how her middle school debate training prepared her to think on her feet in high-stakes ethics conversations.

We discuss the Rules of Professional Conduct that lawyers misunderstand most (client confidentiality is much broader than attorney-client privilege), why trust accounting violations lead to presumptive six-month suspensions even when no client loses money, and how Hillary's work is fundamentally about helping lawyers navigate the emotions—fear, perceived injustice, attention scarcity—that drive risky decisions.

Keep reading below for the full link to the episode and the full transcript of our conversation.

Top Insights

Below are the highlights of our conversation:

• Fear, Not Greed, Drives Most Ethics Violations: Hilary rarely sees lawyers intentionally stealing from clients or acting maliciously. Instead, most violations stem from fear—fear of losing business, fear of not being equipped to succeed at a new firm, fear that clients won't follow. That fear leads junior partners to take proprietary documents, equity partners to solicit clients before giving notice, and associates to stop billing time because they feel the firm owes them something.
• The 90% Rule for Client Portability: Most clients fall into two buckets: they identify you as their lawyer (and will follow you anywhere) or they're loyal to the firm (and won't leave no matter what you do). Hilary estimates this covers 90% of books—meaning the timing of when you talk to clients rarely moves the needle, and the anxiety-provoking risk of early solicitation usually isn't worth the minimal upside.
• Client Confidentiality ≠ Attorney-Client Privilege: Rule 1.6 (client confidentiality) is much broader than privilege—it covers any information learned during representation that the client doesn't want disclosed, even if it's public or just the fact that you represent them. Hilary sees lawyers violate this constantly because they conflate the two concepts and don't realize how wide the net actually is.
• Confidence (or Projecting It) Separates Rainmakers: The most successful lawyers Hilary works with exude calm, self-assured energy—a "I've got this" vibe that makes clients feel protected. Many are deeply insecure underneath, but they project confidence because clients need to believe their lawyer will anticipate problems and handle anything that comes up.

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Full Transcript

Khurram Naik: This is Forum with Khurram's Quorum. My guest today is Hilary Gerzhoy. Hilary is a partner at HWG and she focuses on legal ethics and malpractice issues. Hilary is a frequent speaker on legal ethics, and so that's how I learned about her practice. I find she has such a thoughtful approach to advising on the intersection of the business of law and the ethical duties of lawyers. It’s also a fascinating niche to occupy, so I was really curious about how she came to this niche as well. So, a lot to explore here. Here's Hilary.

Khurram Naik: Hilary, I'm so excited to have you on. Since the first time I saw you speak, you're a dynamite speaker, and so… I didn't think probably the very first time that I’d have you on the podcast, but the second time I saw you speak, I definitely thought about it. So, excited to have you on. We've been having some conversations about your background, and so one part that is really interesting in your journey: you always knew you wanted to be a lawyer from as soon as you learned about what a lawyer is. You said, "That's me, that's what I want." And but interestingly, your first job after college was in sales at Google. And so I’ll be interested in hearing about that experience and then how it tied into now your work as a partner—and as a partner, you have business development to do. And so I’d be curious to hear about what that first foray into sales was like for you, and then the maybe somewhat surprising return to sales in your career now.

Hilary Gerzhoy: Yeah, for sure. Well, thank you for having me on. I, so as you said, I always knew that I wanted to be a lawyer. I went to U Chicago undergrad, which I absolutely loved, and met my husband there, and some of my best friends are from U Chicago. And I… but it was an intense academic experience, and I knew that I wanted to go to law school, but I wanted to take a year between undergrad and law school so that I could rest a little bit. And so I had been applying to paralegal positions in DC. That's what I thought would be interesting for me. And Google came to campus and they were interviewing, and I got an email saying, "Do you want to interview?" And so it seemed like it was worthwhile to go and interview. And so what they were hiring for were college—recent college grads—to go and sell AdWords, which at the time were on the left-hand side of your screen is where you had the list of all your AdWords ads. And so I took the job because it seemed like, "If I'm going to do something for a year, this is a really cool thing to do. Google's a super cool company. This is a unique opportunity to do it. Maybe I want to stay for more than a year, maybe I want to stay for a few years. Living in California is awesome." So I went and being at Google was pretty amazing because being at Google—and this was in 2010—so being at Google in 2010, Larry and Sergey still gave their talks to all the Google employees. And so every Friday, like, you could go and just sit and watch Larry and Sergey talk about what they were doing and what the company was up to. And but I realized very quickly that I was really not good at this job. The job was to… I was working for financial in the financial services vertical, and my job was to call potential leads and try to sell them ad space. And I… I wasn't good at it in multiple ways. I was… I found it really hard to get motivated to do it because I didn't find it to be all that interesting. And I think that was sort of the biggest factor. But I also just felt really uncomfortable selling things—like selling something to somebody. It didn't… it just didn't sort of speak to any natural strength that I had. And I just didn't… didn't do a good job and realized I like really, really dislike being in sales. Which sort of goes to your point sort of initially, which is things have… there is a sales element to business development. It feels very, very different to me though, because selling ad space, for example, or selling a product versus selling your expertise: I feel very confident in my expertise. I did not have that and so it all feels very genuine because I'm just talking about what I like to do and what I do and what I think is interesting and what value that I truly believe I can add. Which I think is like what the best sales people do in other ways, right? Like they do it in… they don't just do it about selling, you know, "hire me to do something." So it doesn't feel that way. And but I… it’s interesting that you that you phrased it that way and that you sort of said it that way because it makes sense. You were… I mean, business development is sales in some way. I just never sort of thought about it like that.

Khurram Naik: And today, are there any principles you learned in business development… I imagine they had a fairly structured process or set of principles you used. Do you find yourself drawing on any of those? Was any of the things you learned in Google in that way beneficial to you today?

Hilary Gerzhoy: Yeah, well, I think like being systematic about how you're doing things. So thinking about: where do you get… where do you get your business from? Where and where do you get repeat business from? What are some of the maybe unexpected places that you get business? And really mapping that out and thinking about how to be targeted in that. Like that is… that’s what the job really was. And so I think that's a nice lens through which to think about business development now is really trying to be targeted in the way that I approach it because doing sort of what's effective. But also the things that are effective can surprise you, right? And the avenues that you think maybe wouldn't be worthwhile are incredibly worthwhile, and some of the avenues that you thought would be really worthwhile are not worthwhile. And trying to be objective about that. Because I think a lot of times lawyers… well, you gravitate towards what I think you enjoy doing and what comes naturally. I think those two things often are the same thing, but sometimes they can be different things. But you sort of want to do the thing that comes naturally, the thing that you enjoy doing or speak to the audience that is motivating to you in that way, for example. But some things don't lead to business and other things do. And and I think like where when it comes to what I do, there's a bunch of different pieces to this. There's developing sort of industry expertise, which is just useful in general. And so that's more marketing, right? But having the… so doing things like writing articles, which I love to do and I write a lot of. But do they lead directly to business? Not really. It’s much more indirect, right? It’s not… there have been a couple cases I've gotten that people have said, "I read… I read your stuff. I have an ethics issue." But if I did sort of pure time of writing articles to business leads, that's not the way to spend most of my time, but I really like to do it, so I continue to do it. But I think that's one of the takeaways that I had is being… having a systematic approach to it all.

Khurram Naik: Can you say some more about like what is systematic about your approach now? Is it scheduled? Is it… you are thinking about, you know, "Hey, I like writing, I like giving speeches, let me make sure I'm doing one of each a month." Like tell me what are the ways in which you are systematic.

Hilary Gerzhoy: So I've found that speaking is much, much more effective. And so I still write, but I write a lot less than I used to. And I've found that a lot of one-on-one conversations are really… can be very useful and and good as a way to develop business and and keep that going. And so being targeted in communications with people—like having sort of the people that I speak to regularly and staying in touch with them, that's another piece of it. But if I could sort of purely do just like what I think is interesting and fun to do, I probably would have more of the writing in terms of the ratio of what I do. But now it’s more of the speaking, more of the one-on-one meetings with people, lunches, coffees, that kind of thing.

Khurram Naik: To what extent are you repurposing the content of the things that you're writing for presentations, etc.?

Hilary Gerzhoy: Not really that much, which is I think a potential to do. I'm trying to do it more. What I have done with speaking is I've been… where I'm asked to speak about things. I haven't done a lot of like pitching, "Can I speak at this thing?" And so then I speak to whatever that audience wants. So there… it runs the gamut from, you know, law firms around the country to companies, industry associations—like just, you know, all over the place. And like what they… what they care about with respect to ethics and what they need to know. So a lot of times it’s things like, you know, "What are my malpractice risks as a law firm? How can I avoid them?" "How do I use AI effectively in my practice? What's available? What are the ethical potential… what are the potential ethics traps there?" "How do I navigate outside counsel guidelines?" So a lot of it is sort of answering those questions, whereas the stuff that I write about is all current events. So if something has happened in the news that implicates an ethics issue, and then I write about that because I think it’s interesting. And so a lot of that stuff is sort of not great for then turning into a talk because the audience… it could be interesting for the audience, but when people want to listen to me talk, it’s usually because they want something very practical, which is: "How do I do this thing consistent with the rules? What is my risk? How do I mitigate risk?" versus when I write it’s about sort of, "Here's this thing that's happened in the news and and why is it relevant? Why should we care about it? What does it mean for lawyers more broadly?"

Khurram Naik: And I think that's where, in watching you speak, that's where you really shine is in the being able to address questions off-the-cuff. And you know, there's any number of fact patterns that seem… that are familiar. Sometimes there's some edge cases like, "Hey, I'm not really familiar with it, but here's how I think about it." And so I think you do definitely have a good instinct for a concise, thoughtful take on how to mitigate the practicalities of what someone might be dealing with. I've observed you in the context of talking about ethical issues for partners in law firms and lateral moves. And so yeah, I think that is definitely a competitive advantage you have—is to be able to translate: here are the rules, and then here's the sources of ambiguity, and then what are some takeaways that you have. How did you hone that?

Hilary Gerzhoy: I've always loved speaking. I've always loved debate. I always loved debate. I was in starting in fifth grade, I was in the middle school debate club and and I never stopped. I didn't do any sports in high school because I just did debate as a sport, which I think is a sport, but you know, most people would beg to differ. And then in college, I actually coached middle school debate in Chicago to to kids who lived in on the south side. And I think it's a powerful skill. I think being able to speak in front of a group of people is… is very can be very useful and very powerful, and I enjoy doing it. And I think part of what I liked about debate is I liked the thinking on my feet piece of it. Like the most fun was the fact that you constantly had to adapt. It wasn't just sort of giving a speech, it was you have to anticipate what your opponent is going to say and respond to it in real time. And then that sort of within being a litigator, that happens in in all kinds of contexts where you have in real time to be able to articulate a response. And I found that that just was something that came more naturally to me. That wasn't as… there are things that… that was one of the categories that I felt came more naturally. And then when it comes, I think, to doing it in the context of of my job and what I do, because what I do all day every day is help lawyers, law firms, companies navigate the ethics rules and all things that go along with that, I have seen so many permutations of these problems. So, you know, as relevant to the the talks that you've heard me give about partner recruiting and and how it impacts firms, how it impacts the partners. I've seen this so many times that I've seen where where things fall apart or how you can mitigate risk or how you should think about it. And I think part of… and that's I think just incredibly useful to responding to folks' questions about how to do it—is like I've seen it and so this is what I think works and this is what I think doesn't work. I also think an important piece of this is what I'm doing with with my clients is giving them a roadmap and giving them a series of options. So here is what the framework that you need to think about and here are the potential risks and here's the ways to mitigate the risk. But here's the way to also think about what that risk is and the risk that you're willing to take. So there's different… people's risk profile is can be dramatically different. So I have clients who are willing to take much, much bigger risks and clients who are willing to take no risk at all, right? And so I think also being able to adapt to what your audience is interested in and giving them sort of the range of options so that they can make an informed decision about what they're going to do.

Khurram Naik: How do… do you think that clients tend to know what their risk profile is? Do you think risk-averse… I feel like risk-averse people tend to know they're risk-averse. Do you think people who think they're risk-seeking… it seems to me people who are risk… think they're risk-seeking are often mistaken about that, or can be mistaken about that, more than risk-averse people are mistaken about being risk-averse.

Hilary Gerzhoy: I think that's definitely true. So risk-averse people know they're risk-averse, right? And they will come to you and they will say, "I'm risk-averse, I don't want to do anything that's even close to being risky. Could get me in trouble, could get, you know, my current firm angry at me, I could get an angry email from the GC… like I don't want to do anything like that." People who have risk tolerance, I have almost never seen acknowledge that they have a greater risk tolerance. They don't… I don't think that lawyers ever want to ever really see themselves as as risk-takers. We follow the law, we're rule-followers, right? And we help other people follow… we make creative arguments about what the law is, but like our profession is rule-based. And so I think when I see that, it’s always… it’s interesting to me when people have taken huge risks and I'm like, "I just want to make sure that you know that what you did was a huge risk." Because a lot of times folks come to me after they've done things, right? So there's actually a… it’s not just "How… what do I do in anticipation of this decision that's going to implicate a bunch of ethics issues?" It's "I've done something already, I'm afraid of what the ramifications are. What are the ramifications? How do I get out of it? How do I navigate?" All of that. And so much… I’d say, you know, 95% of the time, people will come to me and say that they've done something, and I will be shocked at the way that they perceive what to me is an enormous risk. And sometimes it’s… it’s usually one of two things. It’s usually one, they don't know—like they don't actually… they weren't thinking in real time that this was such a big risk. They were… because they don't know the rules as well, they weren't sort of thinking about what the implications of the rules would be. So I think that's… that’s a decent category is like "I made a mistake, like I took a risk without really knowing it was a risk." And then I think the other category is "I took a risk but because my reason for doing it was so good, it doesn't really count as like me being a risk-taker," right? It's that the motivating reason was so… so top of mind for me that like I could sort of… I don't even see the choices that way anymore, right? It's like a no… "I have to do this." Right? There's a lot of people who I speak to who feel like they have to do things. And the truth is you don't, right? You have lots of choices about how to… how to do things, but they sort of have framed it such that when they have taken a risk, it was a necessity.

Khurram Naik: You know, this… this came… this came up for me recently because I, you know, I practice law, and so yes, you you're trained in following rules. And so now I'm a business owner, and so in many ways there's context switch you have to do where you feel like comfortable with using things like, "Hey, this I'm getting 80% of the returns for 20% of the effort in this way." And so yes, I could run down every single detail, every single comma, but it’s just… it’s just not a good spend on investment. So there's some things that I feel very comfortable making that switch where, you know, that was parts of the parts of the practice that chafed for me was that that what felt like an excessive attention to detail that just didn't really move the needle, right? So I feel very comfortable there. It’s interesting because, so I ran into… not a terribly obscure… a common tax issue that, you know, upon a read of a of an ordinance seemed to create some ambiguity. And so I talked to a tax lawyer about it recently who agreed, "Yes, there is ambiguity, and here's how to…" You know, and this lawyer just happened to have just run into this issue for an another similarly situated recruitment agency. And so it was very top of mind and she was able to speak to this in great detail. And it was interesting because like, I was in a position to make a risk assessment of whether I was comfortable with taking a risk here. And so part of it, some of the training you have to undo as a lawyer in this context—and I'd be curious to what extent you feel that equity partners have to go this analysis too where they're both a lawyer and then also a business owner—where you have to say to yourself, "Okay, yes, I could take a risk here." What I'm finding is that actually the analysis of a risk and taking a low-risk option can actually… on one hand I'm trying to train myself to say it’s okay to take risks, but actually another constant I'm finding is actually it's totally fine to take low-risk options because in any number of scenarios the low-risk option in this case—that’s my conclusion—the low-risk option here will involve the certainty of some small, relatively small payment and I'm okay with doing that because I don't have to think about that. What's most important to me and what's most scarce is my attention, and so I don't want to distract at all from my focus. But what… an instinct that I do have to unlearn is sometimes proving a point, like "Well, I'm a litigator, I know how to take a dispute." So that's the instinct to unwind in any number of cases. But it's interesting because I'm starting to discover very, very recently is that sometimes the low-risk option is just the best option because yes, you can prove a point and and make some new law maybe or something like that if you want to take that risk, but it's a distraction. So unless it's core to your business, core to your practice, you know, you don't have to do that. So I don't know if you… if that's some of what you've seen or advice that you've you've given that that's on point.

Hilary’s thesis that fear drives professional missteps is something Joe Ahmad has observed from the trial side — he told me that fear of loss prevents young lawyers from trying cases and being authentic.

Hilary Gerzhoy: I've definitely seen it, and it makes me think of two two primary instances where this comes up. The first is the equity partner category which you which you mentioned. And then the second—and I can talk about both of them—and the second category is focus—just putting people's attention back on like that what you said: you don't have to think about this anymore. If you take the riskier option, it’s going to be in the back of your mind constantly, right? You're going to wake up, you're going to be nervous about it, you're going to think, "Oh no, like what if, you know, somebody figures out that I did this thing I wasn't supposed to do?" And so for people that I talk to who are tempted to take the risk—because the temptation to take the risk is is usually from what I've seen born of two things. One, a fear that you're not going to keep business or continue to make money, or fear that you won't be equipped to continue to do your work. So like some people feel tempted to take proprietary documents with them when they go from one job to another job, right? Because they're afraid, "Oh, I've been trained up in in this, I know these templates, I know how this all operates and the reason I'm really good at my job is because I have all of this. I have all this material." Well, it’s firm proprietary material, it’s not your material, but there's a huge temptation to take it. Why is that temptation? Usually what I see is the temptation is not because people are being greedy or thinking "It's mine," it’s a combination of two things. It’s feeling like "I worked a lot on it," right? There's a piece of it, but a lot of it is fear-based. Like, "If I get to this other job and I don't have all the things I had at this other firm, I'm… I can't be successful." And that but you have to weigh that fear against the "Do you really want to be waking up in the middle of the night worried that the firm is going to know that you took documents that you're not allowed to take?" Like this… do you want that to hang over your head? Because it will continue to hang over your head. And a lot of folks are like, "You know what? That makes sense. Like it’s not worth it." And the other piece that I always say to people, and I'm sure you have a lot of experience with this, is if you're getting recruited to go to another great job, great firm, it’s not because you had templates at your old law firm. It’s because you're a really good lawyer. And what makes you a really good lawyer is yes, you had access to these resources, but it's all the skills that you've developed. And so like don't sell yourself short in thinking that you need all of these things to do to do your job and to be effective at your job. With respect to the equity… and that tends to be a much more junior person thing, right? So like a junior partner, somebody who's counsel, who's sort of just getting started and feels very unsteady in their position at a firm because they don't have a big book of business. And your power in Big Law is the size of the book of business that you have. It's your power and it's your autonomy. And if you don't have that, you're on shakier ground. And so that you see that happen much, much more frequently in the context of folks who are more junior. In the equity partner camp, it’s the risk-taking that comes up is talking to clients before you told the firm that you're going to leave, for example, right? Which is a breach of your fiduciary duty and you can't do it. And the reason that people do it is because they're afraid that the clients are not going to come with them. And that can come in a bunch of different ways. Like they're afraid, like "Maybe this client hates the law firm I'm potentially going to, and I have no way of knowing that they hate that law firm unless I test the waters and say, 'How do you feel about that law firm?'" "What about if… if I don't sort of set it up in motion, somebody else is going to swoop in? As soon as I give my notice, they're going to swoop in and take take that client from me." "I need to give assurances to the new firm that I'm bringing this client. How can I possibly bring… give… give them assurances?" Right? The target firms put a lot of pressure on candidates to make commitments about how much money they're going to bring in, honestly from the jump. And so how can… for a lot of people they're like, "Well, how can I truthfully say I have X as my book of business if I haven't talked to these clients and these clients haven't actually told me that this is portable work, that they're coming with me, right? So I… do I have to… I lie on my lateral partner questionnaire? Because I don't know. I'm sort of guessing. Like, what am I supposed to do there?" And so a lot of it is like they take a risk because it feels like it’s a necessity, right? Like "I can't answer these questions and make a move unless I have violated my ethical and fiduciary obligations." What I have seen and what I tell people is that I think 90% of clients fall into one of two buckets. They are either… they identify the lawyer as their lawyer, and it… that lawyer can go basically anywhere and they will come with the lawyer. Or they view they have loyalty to the firm. And and it doesn't… and they work with the lawyer and they think the lawyer's great, but the loyalty is really to the firm. I think most clients fall into the first category, but I think 90% of all clients are like easily bucketed into one or the other. And so and it's really that 10% in the middle where maybe if you talk to them first, maybe when the order in which you speak to them, maybe that matters. But 90% of your book is either like with you or not with you and it has nothing to do with the timing of when you say it, right? And if somebody from your existing firm talks to the client first, it’s not going to matter. And that's what I've seen over and over again. And so for people who sort of try to to take these risks and solicit the clients when they're not allowed to solicit the clients, there's not a lot of upside and there's a huge amount of downside risk. And I've represented lawyers in like arbitrations that ultimately result where firms will sue lawyers for leaving, for doing things like violating their solicitation… violating anti-solicitation provisions and it is… it's ugly, it is… it’s not a pleasant thing that anyone lawyer… any lawyer wants to be in because it’s literally your former colleagues coming up against you and like as witnesses, right? And like testifying against you like somebody that worked down the hall from you for 15 years. Your professional reputation is impugned. It stays with you. It… it takes an emotional… it’s not just money, it’s an emotional tax to do it. So and that's if… if the whole thing ends up in litigation. But like there's lots of stages before then that are incredibly anxiety-provoking. And so is it… is it ultimately worth it? I don't think it is when it’s not going to move the… it doesn't move the needle in my… in what I've seen.

Khurram Naik: For that 90% bucket, do you feel like lawyers tend to have… this is kind of similar to the question of like, "Do you know your own risk profile?" Do you think lawyers tend to know gut-level like, "Hey, like is a client really going to go with you?" My guess is most lawyers know, but like what do you think?

Hilary Gerzhoy: I think most lawyers know. I think most lawyers know. I think most lawyers when they talk to me can say like, "I can tell you that 90% right now." And then there's this 10% and I'm not really sure exactly what to do. And the question is, how important is that 10%? Right? Is it 10% of your total book of business? Or is it 10% of your clients, but they're the most important clients? And but I think a lot of it is lawyer… there are a wide range of personalities at play, but there… I speak to a lot of folks who are like, "I don't want to say that this is going to happen with certainty and that my compensation is tied to an expectation I am going to do X, Y, and Z unless I feel really confident that I can do X, Y, and Z. And because I am a risk-averse lawyer and because I have to, you know, dot my I’s and cross my T’s about everything, I can't be sure unless I… unless the client tells me, right?" And so "I want to be… feel confident that I'm giving a truthful answer and that my…" and then that I'm not setting expectations in a way that is not realistic. Both because I think people feel uncomfortable—like if, you know, if your target is to bring in a certain amount of money and you clearly can't do it, that's an awkward position to be in—but also to go down in compensation psychologically is very hard for people. So like you go in with this very like competitive compensation package and then the next year you make a lot less. And I think people just do a lot better with small incremental gains versus a big jump and then back down even though back down is still better than what you had before. It's hard for folks. I think that's what… when we talked a little bit about remote work, I think it comes up in remote work. Like taking away a benefit is a lot harder than if people just sort of like gradually got… okay, you can work from… If you told lawyers five years ago, "You could all work from home one day a week," people would be like, "That's amazing," right? Like that was a huge appeal of working for the government was that you could earn days to work at home. And I… we would talk about in private practice all the time that we were like, "Oh my God, government lawyers can work… like earn a day to work from home. That's so amazing." But then people get used to what they have and they get used to what they have really, really quickly. Like almost instantaneously is how fast it is. So then you cut compensation, you cut benefits, even if they're better off than they ever had been before, it hurts and people… and I think a lot of people want to avoid that.

Khurram Naik: I feel like we're really… this is such an interesting delve into psychology, professional psychology because like you just touched on this like loss aversion kind of principle. And I was about to ask you about… I think two things you've already identified as emotions or or emotional beliefs that are recurring are fear—so identified fear as a big one for the lawyer who's going to try to take the firm templates or whatever that they worked on. And then you also identified attention—you know, something I was talking about, something you're talking about is the importance of "Hey, like do you really want this as a distraction?" So I feel like we're starting to identify some of the fundamental underlying emotions or beliefs that are really govern… there's so many different kinds of ways you can challenge ethical rules or run afoul of a contractual provision. Do you think in terms of this this kind of this ontology of of of emotions? Like are there other fundamental emotions that you think of that that recur in the same way that we've already identified a few of?

Hilary’s description of BigLaw as a “greedy profession” — trading a huge portion of your life for high compensation — made me think of Patti Burris, who found a way through it. Billing over 2,400 hours, Patti maintained a 7:2:3:1 wellness ratio that protected her non-negotiables.

Hilary Gerzhoy: Absolutely. And I think so much of my job deals with people's emotions. Like it's a huge part of of conversations that I have. A disproportionate… like if I sort of think about other people's practice and their legal practice, I would imagine I have a really disproportionate number of conversations about how people feel about things. And I think that's honestly one way in which I have an advantage—is I think I'm good at talking to people about how they feel, and I think I can understand how people feel and I… can… what I have been told is that I that people feel comfortable talking to me about things that they don't necessarily feel comfortable talking to other people about. And getting to sort of the core of what's motivating you can be hugely helpful in thinking about the problem, right? Because the problem is framed by what you care about and what is… what your drivers are. I think another big driver, so I think fear is a big one. I think, you know, how you spend your time and energy. I think a sense of equity and justice is huge. And I think that is… so when people do things like, for example, you know, solicit clients when they can't solicit clients, or when they… they know they're making a lateral move and they stop billing their existing work—like they stop invoicing clients, they stop recording their billable time. That's a breach of your fiduciary duty, right? You're an employee for a law firm. You can't just stop billing the time that you spend. But they feel like they've been mistreated. And they feel like there has not been equity because other people have gotten paid more than they have and they deserve to get paid more, or other people have been treated better, gotten practice group chair, gotten whatever sort of highlight from the firm and they haven't and that was unfair and unjust and therefore they want to get some sort of revenge to feel like there's there's more equal footing, right? Like "I've been treated unfairly, therefore I can treat you unfairly." And I think that's a big motivator for for just human beings in general, right? Like it's even even if you don't care so much about the thing, the fact that you've been not treated equally irks people at a fundamental level. And you'd be surprised like how how small those things can be. Like to an outsider, they can be like, "Really? Like that? You're so upset about that?" But it's because like people have a visceral reaction to being treated to perceiving themselves to be treated unjustly. And part of like compensation structures—but it becomes so hard in that context because most law firm compensation structures are pretty black box. And so you don't really know, and I think a big reason that they are black boxes is because when they are more open systems, it lets everyone say like, "Wait, but my hours were this, my receivables were this, my, you know, all how is she getting more than I am?" And when it’s black box, you sort of take that piece away. But then what you introduce is sort of this sense of suspicion among everyone. Like this is what I I talk to lawyers about this all the time—is always feeling just a little unsure and a little bit like you have you got the raw end of the deal. Basically every lawyer I talk to like thinks that that's prop… something like that might be at play. In part because like the way that that the private practice of law operates is: Have you ever heard of the idea of a greedy profession? I think there was like a New York Times article about this a few years ago, and it listed a few greedy professions. The law was one, being a consultant was one—like a management consultant, you know, you like work for Bain or BCG and you travel five days a week—professions where there's people who you get people who have specialized skills. It usually takes a a lot of expensive education to get them to a position where they can participate in a greedy profession. It is highly… it is really well compensated, but it takes from you. It it demands from you. It is the profession is greedy in what it demands of the people who work for it. So you get to have this fancy job where you're doing really intellectual… intellectually stimulating work and you're making a ton of money. But in return, you're going to give us a huge portion of your life.

Khurram Naik: And I'll add to what you're saying is, in contrast to let's say you were a real estate agent and you sold a thousand homes in a year, there's much more ambiguity about the nature of your work product.

Hilary Gerzhoy: Absolutely. Yeah. I think that's absolutely right. Like you can do because in those professions too, you can do… it’s a little bit more "choose your own adventure" than it is in something like consult… management consulting. You know, there's a very specific path. This is what you're supposed to… and and the law is that way in a way that like very few other like very few professions are, right? Like you start in as an associate, you work as an associate for X number of years. Then at most firms you become counsel. Then if you become counsel you can become a non-equity partner. Then after non-equity partner, you become an equity partner. But even if you go before that, right? You start you do really well in college, then you go to a competitive law school, then you try to get a clerkship, right? Like there's this path that is laid out that is the the front getting in the front door, right? And that doesn't mean that people don't get in on the side doors and there's other ways to achieve that. But there is this sort of like "Here's how you do it to end up at the place that a lot of people want to end up." But there are sacrifices that are involved in that, right? Which is really that you're giving up a huge amount of your time. And so I think all of the… the reason I bring this up is because I think all lawyers—not all lawyers—I think a lot of lawyers who work in Big Law feel like they've given too much and that they sacrifice too much. And that and so and because of that, that money becomes such a huge piece of the puzzle for them—it’s an outsized piece of the puzzle because they feel like they've given the firm more than they should have. And I think that's part of the nature of of Big Law is that's the way it operates. And I mean, it’s not for no reason at all, right? It’s you have clients that are incredibly demanding, right? And the market is incre- is super competitive, right? Everybody's competing for a finite amount of work at a really high level, right? And so you have to be availability becomes incredibly important because if you are not available in that way, the client can find another law firm that is, right? And so why is it taking from you in that way? A lot of it is just the practical nature of who the clients are. This is client services, right? Client services are demanding. I think that's a piece of it. And then I think the other piece of it is, you know, mandatory billables, right? We have to you have to bill X amount. That's where I think where people get more frustrated and have sort of more bad reactions versus I think folks know like clients can be demanding, right? And I if I have to be available on my vacation, I have to be available on my my vacation. But it's where it feels arbitrary. So like the senior partner is insisting that I be available, but nothing's actually happening right now. That's when people start to to be motivated by to do things that maybe they otherwise wouldn't do.

Khurram Naik: There's there's a lot of interesting things you just talked about and there's a few jumping-off points. One jumping-off point is when you're initially, so you mentioned that you have really resonated with the emotional core of this and and helping people express and communicate and identify those emotional underpinnings and then using that to guide action. So one question I have is, was that part of the role apparent to you earlier on, or were you drawn to the work for some other reason?

Hilary Gerzhoy: It was not apparent to me before I started doing the work. I started… I had just done general general litigation, right? Doing and I did sort of probably half appellate stuff, half half district court work. And then some white-collar stuff, but mostly in the commercial space. And then I came to the firm I'm at now, and I started working with Tom Mason who had founded our practice group. And his his pitch was just "You like litigation, this is litigation for lawyers." And I did not appreciate initially how much it involved sort of thinking about the human being and not just the lawyer behind all of it. And and it also became much more apparent to me the more senior I got because now I have my own clients, right? And so when it… when you're working with somebody else's clients, there's always sort of there's a level in between, right? I'm doing the… I'm drafting the memos, I'm drafting the briefs, I am sometimes getting relayed what the client cares about and what the client wants, but I'm not the one having those phone calls as a junior person. But now, it's they're my clients, right? And so I'm talking to them and so I I sort of see it in a very different way. So it was not something that was obvious to me at the beginning, but it is definitely something that makes me love doing what I do because I find it very motivating and satisfying to try to help people figure out like "What's the right thing for you to do? What's going to make you feel like you came to the right answer?" And how do I solve your problem? That's the other piece is like litigation… this is one of the reasons I like the ethics work so much is litigation is adversarial. And so and that's draining for me, right? Like there's some people who just like the fight. I like the things that the the things that you do to be a litigator, like research, writing, oral advocacy. I hate the fight. So like the thing about debate that I loved was I liked thinking on my feet. I liked that that like it pushed me to be creative, but it’s not that I liked like "I'm going to fight someone." That is just I don't have that. That's not enjoyable to me. And with the ethics work, some of it is litigation, right? Like sometimes we've got to fight. We're we're, you know, in a disciplinary proceeding, it’s a malpractice suit—like that's what we got to do. But a big chunk of it is: I can solve the problem. And we can come up with a solution, and there's like so little in the world of litigation that actually falls within the "Let me come up with a solution" category that there's something really nice about that.

Khurram Naik: It also seems to me that what you're helping people do is make decisions that are, I think, at their core everyone… most people have an ethical compass, and sometimes it gets compromised and then but then I think people regret that and you can they can go pretty far down that route but then and just of just consistently makes decisions in life that compromise some ethical value they have. But I think at their core people want to help be guided to ethical action. And so I imagine it’s a gratifying part of your process. What what's the principle you use? So let's say somebody communicated to you, "Hey, I'm operating out of fear," "Hey, I'm operating out of out of feeling unjust." Like, how do you then say, "Hey, I get you're feeling those things. How do you use those as like, now I understand that's your framing, how do you get them back on making decisions that are consistent with their ethical compass and so they have autonomy, agency to that… that is the motivation, not like the fear of the rule and getting, you know, the stick" or whatever?

Hilary Gerzhoy: Yeah, I think it’s it’s understanding what the… what the risk is of doing the wrong thing, not in terms of the stick of getting disciplined, but that you are taking on this risk and you don't need to be, right? And I think it’s like so people understanding that the fear is they feel fear that is not proportional to what the actual danger is. And that and and I think that can be relieving for people to sort of understand to put everything into context. And I think the other thing is for people to know that every… that other people feel that way too. Because I talk to lawyers all day, and I talk to lawyers who are similarly situated to one another—and and that means like I've talked to lawyers of all, like solo practitioners to working in Am Law 5 firms to government lawyers, public interest lawyers—like but I've talked to enough of them that I can say to people like, "I know you feel this way. You… this is not unusual, right? A lot of other people in your position feel this way." And I think that is hugely satisfying to people because that's just like human nature, right? When you feel like you're not alone. One of the… I had an interesting call with a client the other day where because I've just seen how this works and I see how the market operates, I… true… he’s at his current firm thinking about moving, thinking about all the things that are associated with that. And what I said, like he explained his compensation to me. And I said like, "You… your ratio of hours toward hours versus what you take home, your origination, your hours, what you take home is a better deal than I've ever seen anybody get." And that like just fundamentally changed the way he thought about his current job. And nothing else changed, right? Nothing else… he worked with the same people, same clients, same type of work, same hours, all that. But knowing that it was a good deal in comparison to others was satisfying to him and made him feel a lot better. And I think the other piece of that is knowing that like other people feel that they've been treated unjustly in this circumstance or that I honestly think that nobody ever feels like it’s completely fair how compensation happens, for example. That is also I think very helpful for folks.

Khurram Naik: You know, you spend a lot of time thinking about ethical rules and I imagine a lot of that: what percentage of the ethical rules that you're thinking about are like the Rules of Professional Conduct?

Hilary Gerzhoy: Oh no, so that's it. That's what I'm thinking is the Rules of Professional Conduct. So that's the ethical restrictions—like it's rare… it’s that the lens through which I'm seeing things. So like when I get hired, it’s because lawyers have questions about what they can do, they've been accused of doing something under the ethics rules that is improper. When with any malpractice suit, ethics stuff comes into play because the the central argument in a malpractice suit is that you fell below the standard of care, which is you didn't zealously and diligently represent me, which is implicates all the ethics rules. Um, so it's always thinking… it’s either litigating with respect to the ethics rules or giving advice with respect to the ethics rules or defending somebody who's in a disciplinary proceeding, for example, which is purely about the ethics rules. There's no monetary sanctions, for example, in a disciplinary proceeding versus a malpractice suit is obviously done for monetary damages.

Khurram Naik: You know, I haven't given a death of thought to the Rules of Professional Conduct since, you know, taking the MPRE, and I imagine that's true for any number of lawyers. You, especially if you're at a bigger firm—like, "Hey, we kind of have like largely guidelines for how to progress here and how we do our work and there's guard rails." And so just there's plenty of ways to not be thinking about those issues. Of course, I think there's plenty of ways to run afoul of them in ways you don't realize—like "Hey, I'll just download this material from, you know, from the firm and, you know, what's the difference?" But so are there… is I'm curious how you think about this. Do you feel that there are… um… I can imagine someone, let's say a trial lawyer, might have an opinion that "Hey, there's underrated rules of evidence" or "underrated hearsay exceptions" or something like that that, you know, if you're just thinking about them all the time like "Here's… here's something in your repertoire that you may not really appreciate." Do you feel there are underrated or underappreciated Rules of Professional Conduct that affect lawyers more than they realize?

Hilary chose speaking over writing as her primary business development channel — and so did Jaimie Nawaday, who built Disrupting Drinking as a speaking venture rather than writing a book. Both found that talks are faster to iterate on and create deeper audience connection.

Hilary Gerzhoy: Yeah, I think there's there's different ways to think about that question. One is like: Where do people run into trouble? And if it was top of mind, they wouldn't run into trouble. I think that's one avenue. And then I think another avenue is: What do the Rules of Professional Conduct say about X such that I could do X more and then be better at my job, right? So not that the risk is that I don't do it and I get in trouble, but I could do it more. With respect to like where people get into trouble, the… so where people get into trouble in the disciplinary process is extremely different from where people get into trouble in the malpractice world. Um, so disciplinary proceedings are about… anybody can file a bar complaint, and disciplinary counsel can can institute an investigation on its own based on anything, right? Like they can read an article in the New York Times that talks about a lawyer doing something that seems shady and they institute an investigation. They've subpoena power. It much… it really mirrors the sort of criminal justice system a lot more than it does civil litigation. I mean, like there's a lot of due process, all of that. But what do lawyers get in trouble for? I mean, disproportionately small firms and solos get in trouble. Why? Because client money is a big concern, right? It’s a big concern of the bar of disciplinary counsel for good reason, right? We don't want lawyers stealing client money. But the trust accounting rules—the rules that govern like how you deal with client money—no lawyer at any big firm has any idea, right? Like they don't… do they even know what an IOLTA account is? Like why would you because you're not touching client money. You maybe are the one sending out an invoice, but that's it. Um, and so you sort of have the the freedom to not care about it because there's a whole infrastructure that does care about it and that is tasked with doing it as a full-time. But if you're solo or a small firm, you're absolutely dealing with client money and there are so many opportunities to make mistakes in this process. So I'm not talking about the client who like intentionally steals from there… the lawyer who intentionally steals from their client. I basically never see that is the truth. It’s the lawyer who made a mistake in the process. Either… so in in DC, for example, the rule—it’s 1.15—is incredibly draconian. If you commingle any client money with your money—with the firm operating account money—even if the client doesn't lose a dollar, it’s a presumptive six-month suspension. And that's huge, right? Like what does a presumptive six-month suspension do? So you made… you truly made a good faith mistake, right? You used the wrong checkbook and we are presuming six… six-month suspension. So that's one aspect—like if I ever… when I talk to small firms and solos about what to do, I always say like, "Make sure that that is as perfect as possibly can be because that's something that you're going to run into trouble with." In terms of an under… where people where lawyers I find don't don't appreciate what the rules say, it comes client confidentiality. So Rule 1.6 is what governs client confidentiality and it is much, much broader than attorney-client privilege. So lawyers all know attorney-client privilege. They all think about attorney-client privilege and they think about work product privilege, right? Um, but client confidentiality is any information that's learned in the course of the representation that a client doesn't want you telling people. And it could be… and it doesn't have to be learned from the client, right? It’s in the course of the representation. It could be public information. It could be the fact that you even represent the client. So like if somebody could go on Pacer and see that you represent a client, if the client doesn't want the world knowing, that's client confidential. And so a lot of… of sort of ethical issues that happen is because lawyers have revealed information without appreciating that confidentiality is much broader than attorney-client privileged information. Um, with respect to like sort of tools in one's toolkit that can be used more, because that was your question about sort of like, you know, evidence: I think so 1.4 is your communication obligation. You basically have an obligation to keep clients reasonably informed about matters. The key one that everyone always thinks about is like if there's a plea… if there's a plea offer, you got to tell the client there's a plea offer, right? Or like if you're in some kind of negotiation and there's a counter-offer, you got to tell the client, right? You can't just say no without talking to the client. But I think so many problems could be avoided for lawyers if they embraced that obligation more um consistently with what it actually says, which which is keeping clients reasonably informed. When clients get angry, a lot of times they get angry because they don't know what's happening and they don't know what's happening in real time. And so simply just like giving them a little bit of information as things go on can actually avoid a whole host of problems down the road. So like a two-sentence email can avoid a lot of issues. And if that’s sort of regularly part of your practice is keeping clients updated and informed. The other thing is when you make a mistake, and that's the hardest. And that's the hardest, I think for particularly for lawyers in Big Law with all the credentials and all the fancy things. Every person makes mistakes. We are all fallible. We make mistakes every day. But it becomes… when the stakes are really high because there's a lot of money on the line, because you are making a lot of money, because um getting to that position took… took a lot of money, right? You had to spend a lot of money to get educated to get there. Making a mistake and the human desire to make it go away is very, very powerful. To not tell other people that you've made a mistake, to figure out if you can fix it before anyone finds out. That piece, and like creating a work atmosphere where people feel comfortable to say they've made a mistake, another area where you can avoid a ton of problems. Because you haven't… if you make a mistake and it’s critical to the matter in some way, even if you fix it, you still have to tell the client about it. And clients can be… some clients can be unforgiving, but a lot of clients are… you know, can understand that people make mistakes. But I think that's a really hard one, and I've seen it be harder sort of the the fancier you you are and the more you have the all the fancy things, the harder it is for folks to say, "I made a mistake."

Khurram Naik: Are there any instances of with… with both of these rules with respect to any of them, where you feel that people are unnecessarily taking obligations that don't actually exist, where people are making it harder for themselves?

Hilary Gerzhoy: Oh, well so that's the sort of the opposite of the rule the 1.4 issue is some lawyers feel like they have to tell their clients every… they have to be responsive all the time. That's… that’s a way in which I think the practice of law becomes super greedy. If and lawyers—and it will be as greedy as lawyers let it be—because particularly there are clients out there that do not respect the time of their lawyers, right? They think, "I'm paying you a lot of money and therefore you are perpetually available to me at any given time." Nothing actually requires you to do that, right? And so nothing requires you to be… being responsive to a client does not mean being available all the time. And I think setting boundaries a lot of the time is respected and you can… I think lawyers have more freedom to set more boundaries with their clients than they often think they do. Which again, I think is a lot of the fear motivator, because they're afraid, "Well, if I'm not responsive all the time, there's somebody, you know, there's another law firm down the street, they'll be responsive at… at all hours." Um, but if you're good at what you do, like having confidence in that and saying like, "I'm not… you know, I see that you emailed me on a Saturday. I'm going to email you back on Monday morning," unless it’s truly urgent. And the category of things in the law that are truly urgent is very small. And like recognizing that it’s actually very small. I think it’s much easier said than done in general, but it’s also much easier for those who have the direct client relationship. Where it becomes really hard is if you don't have the direct client relationship and you're working for other lawyers, then like what your boss says is what your you… your boss is really the client that you're thinking about is the person that you work for at the firm. And if they have unrealistic expectations and demands, setting boundaries can be really hard. But you see the next… you know, the next generation is doing that a lot more. Um, but I I wonder what the… you hear I hear all the time from senior lawyers that they're frustrated with that generation because for them, like you had to be available all the time. That was just the nature of working in Big Law—like that's what you signed up for. How come they don't get it? And how come they don't want to do that? And I think they just have they're different values and they're different priorities that are placed on things. But that is one area in which I feel like lawyers feel they have to be responsive to to a degree that nothing requires them to be, and that they probably could set more guard rails and be happier as a result.

Khurram Naik: Yeah, I love that. What… what Rule of Professional Conduct would you change?

Hilary Gerzhoy: Oh, the one… the trust accounting rules, for sure. So I'm uh the Vice Chair of the DC Rules Committee, so that's the committee that proposes changes to the Rules of Professional Conduct that then go to the DC Court of Appeals. Um, and that was a proposal and there's been a lot of pushback um on it. But I think it’s incredibly important because I think you do not want to have penalties… the penalty has to fit what the crime is and the severity of the crime, right? And when somebody makes a mistake and nobody's hurt, having a presumptive six-month suspension, that can destroy somebody's career. Like if you're a litigator, every time you pro hac into every into any court, you have to say if you've been disciplined before. And there are lots of courts out there that will not let people pro hac in if they've ever been subject to discipline. It it is public—it’s public record—like at the the Washington Lawyer magazine and every every jurisdiction has their magazine, it has a list of everybody who's gotten disciplined. Um, it’s out there, right? It’s a… has huge career ramifications. And if it was really a a mistake that was not because you were being reckless, but was just because you're a human being who made a mistake and nobody was hurt, I do not think it is appropriate that we have a presumptive six-month suspension.

Khurram Naik: What's rule number two? Rule number two that you'd change.

Hilary Gerzhoy: Well, I don't know that I'd change it, it’s just it’s a really hard one to navigate, which is 8.3—which is your obligation to report when other people do things that violate the rules. That's a really, really tough one for people. Um, and I don't know what the answer is. And I think that the rules have… I think where we have landed is is sort of the best you can get, but it’s not very satisfying because it’s when somebody has done something that calls into question their fitness to practice law. What does that mean? That means very different things to different people, right? So like I was… so I teach legal ethics to professional responsibility at Georgetown. Um, and yes, my class was yesterday or two days ago. Um, and we were talking about reporting obligations and and somebody said, "Well, if you know that a lawyer is like consistently unfaithful, right? And cheating on his wife and cheating on his wife with tons of different people. Like doesn't that mean he's like not a trustworthy guy? Shouldn't I report him?" Right? And I mean, that's a hard question, right? I think the answer is no, that doesn't trigger a reporting obligation, but I could see why you might think that. Um, or, you know, somebody has a drinking problem, for example. Do I report somebody who has a drinking problem? What are the ramifications of reporting somebody who has a drinking problem? Um, the thing about 8.3 too is the reason that it’s sort of it’s hard to navigate—it’s also really, really hard to discipline people as a result for violating it. So it becomes a little bit toothless because you see basically no prosecutions for like, "Oh, you knew that he was forging documents and you didn't report him to the bar." That fact pattern comes up basically never. So that's a hard one for for people to figure out—like "When do I actually have to do this?" is… can become a very tricky question.

Khurram Naik: I'm curious in… you know, you see successful partners and you you see an interesting cross-section of their circumstances and and get really gritty into finances and that kind of stuff, and so you see patterns and commonalities. I'm curious apart from working hard and being great with relationships and thinking in terms of business, apart from those qualities that somebody could possess in in in as a as a rainmaker, what are commonalities you've observed among various successful lawyers that… and let me qualify as say um not just ones who are successful monetarily, but ones you think big picture are good lawyers, good ethical compass, you know, just overall like good people like who are very successful. Like what are commonalities that you're seeing among those people?

Hilary Gerzhoy: Note, I would I think of two categories that go to each each of those things, because I think that there they're two different answers. I think for somebody who's successful in being a rainmaker and successful at what they do and has a big book of business and is well-regarded, one quality other than the qualities that you mentioned, I think is confidence. And or at least projecting confidence. Um, because you meet a lot of people who actually are are deeply insecure, but they project confidence. Because the thing is that clients are hiring… they want to feel like they've hired somebody who's going to protect them, right? In whatever way that is, right? If you're in a transaction, if you're a personal injury lawyer, if you are um doing, you know, a private equity deal, right? You just clients want to feel like their lawyer knows what's… knows what's happening, knows what's going on, is going to see problems before they happen and is going to protect them. And so if you give off that just energy in life, that I've seen that as a very, very consistent thing with the people that I talk to who have very successful law practices is they sort of give off this air of confidence, confidence, like self-assuredness and calm. Like a calm energy about… because it’s sort of like a "I got this" vibe, right? I think that's one piece. Now with respect to like what sort of sets people up for being ethical um and being sort of compliant with the rules and staying on the right side of things, um I think thinking about the client is the most important thing. The lawyers who think about the client first because, as I said, like we're a client services profession and I think sometimes lawyers don't think about that in quite the way that that is contemplated by the Rules of Professional Conduct, which is all of this is designed to have the public have faith that lawyers are held to a certain standard. And so when a lawyer says something or does something that we can have trust in them, right? Like that a lawyer's not going to get in front of a court and lie. That a lawyer when they're when you're interacting and negotiating with a lawyer, that they're going to be truthful in those negotiations. It's sort of the… there's lots of jokes about lawyers being liars, but the way that the profession actually looks at it is because you occupy a position of power and therefore there are certain restrictions that are put on you and certain expectations. And I think the lawyers who think about their role as being an advocate for their client first don't fall into so many of these traps. Because if you're focused on what's in the client's best interest, you're not going to… you're not going to make a mistake that's going to be a mistake that amounts to a violation of the rules. You might make a mistake because we make mistakes as human beings and you might get sued for malpractice, uh but lots of folks can get sued for malpractice when they didn't commit malpractice. Uh, but you're going to stay on the right side of things if that's the perspective that you occupy.

Khurram Naik: That's interesting. I wonder how you'd also consider scenarios where there's any clients who don't have full appreciation for ethical conduct or um and then also aren't repeat players in court or or otherwise in the practice of law, where there's scenarios where lawyers have to challenge their clients or or or decline representation as as necessary, where clients are expecting… saying, "Hey, like this is fine," then they expect and the lawyer's saying, "Hey, like I know that that's a departure from what's right." So I don't know how often you run to observe that as a pattern. Because I totally understand what you're saying with like having a client-centric focus and that is a good North Star for saying, "Hey, am I doing the right thing here? Am I just looking out for myself or looking out for the client?" It seems to me there's sometimes situations where the inverse is is the most ethical path and and so that's also a tool mindset that lawyers have to keep in mind too is their reputation, the firm's reputation, and and the profession's reputation. And so um I wonder about that.

Hilary’s discussion of government lawyers facing ethical dilemmas in the current political moment connects to my conversation with Judge Vince Chhabria about public service as the north star of a legal career.

Hilary Gerzhoy: Absolutely. Yeah, I think I mean it’s absolutely true. Um, and I think it can come up in all kinds of contexts. But one way that I'm seeing it happen now is politically. And lawyers who are involved in in politics um and with this administration and being pressured to do things that they know are unethical. So I I have a lot of clients that are government lawyers, uh recent recently departed government lawyers, currently government lawyers that that may or may not be government lawyers for very long, and a big chunk of of the conversations that I'm having are: First of all, the general counsels from my agency have been fired, there's no general counsel to to talk to, so I need to hire an outside ethics lawyer. And I am being asked to do something that I don't think is right. What do I do? And the answer is for every client representation: if you are being asked to do something that violates your ethical obligations, the answer is withdrawal. You have to withdraw from the representation. Now, first you try to persuade your client to not do that thing, right? And but if your client insists on a course of action that requires that you violate your ethical obligations, you have to withdraw from the representation. And I think that is easier in certain circumstances and harder in others. Um, but I would imagine that there are plenty of lawyers right now who are working in the administration who feel deeply conflicted. And I think there's probably plenty that don't feel conflicted at all. Um, there are plenty that were there and just, you know, immediately, you know, resigned. But I think that there are lawyers who feel deeply conflicted about what to do, um who their client is too, right? When it’s the government, that's also like the government when you when you work for the government, the client is not the president. The client is the head of the agency is the agency that you work for, right? Like the Justice Department. Uh, so what is in the best interest of the Justice Department? Um, but I think that that is sort of a has come to the forefront because of where we are in history, um in a way that it sort of never… I don't think it has before.

Khurram Naik: Hmm. Can you give us a breakdown… I we haven't talked about the big picture breakdown of your practice to help people understand the context of of the mixture work that you have.

Hilary Gerzhoy: Yeah. So I do um a big chunk of my practice is serving as outside general counsel, um which means that I get hired by firms of all sizes—from solo firms, small firms that don't have a dedicated general counsel to basically be that person for them. Um, or get hired by big law firms that have just sort of a dicey weird ethics question that needs somebody to do a deep dive. A lot of times that goes to things that deal with conflicts of interest because those are… that can be really hard to to navigate, um and they can get particularly when there's lots of um lots of clients with competing interests with where there's overlap, there's subsidiaries, affiliates, there's outside counsel guidelines, there's lots of things to navigate sort of what the answer is there. Um, so I do a lot of outside general counsel work that deals with with that and also with just managing clients—like "Looks like there's going to be a fee dispute. What do we do here?" And then I do the litigation aspect of it, which I think of in two categories, which is the malpractice litigation and then also litigation with respect to the disciplinary conduct. So representing lawyers and firms that have been accused of violation of the Rules of Professional Conduct in that whole process, which results in… it’s an investigation and then if it if you ultimately don't get it dismissed or have negotiated discipline, which is sort of like a plea deal, um then it goes to a trial and then it can and then it goes to an appeal. And so litigating that those cases. Um, so that's like the combination. And then within the sort of general counsel stuff, a lot of it is just like one-off ethics things that lawyers are dealing with. So like the context in which we met, which is lawyers who are making lateral moves, there's just a lot of ethics issues that come up in that. And so some people wanting guidance about "How do I… how do I do this? What tell me what I don't know what I don't know." Um, "I took professional responsibility 30 years ago" or even "I didn't ever take professional responsibility because 30 years ago we didn't even do that." Um, "and I basically remember none of it other than 'don't steal from your clients.' So like tell me here what I need to be thinking about."

Khurram Naik: So in your capacity, you see lots of things that work and lots of things that don't work, and I wonder if you think of your work the same way that I do. So, you know, something that I've come to appreciate in my role as a in a recruiting agency is we see recruiting practice in lots of firms. We see how lawyers think in terms of making moves in lots of instances. And so that that helps inform us in a couple tangible ways. So it comes to things like agreements. So things like a recruiting agreement, there's terms in there that I've come to have an appreciation for, there's market terms that you can kind of understand like "Hey, across firms there's maybe variations in some ways on some of these terms, but there's a a abstraction away across these firms of the market terms." And so part of what I do is guide firms on "Hey, what is market terms? You may not appreciate what are market terms. Even really large law firms may not have an appreciation for market terms." But more fundamentally, I think what's really helpful in my capacity explain why these are market terms. What is it that is beneficial to the firm for using market terms? And um and that what benefits a firm is not zero-sum to what benefits the recruiter, not zero-sum to what benefits the candidate. What do you mean by market terms? Uh, terms of say like how much recruiters are compensated, the structure of their compensation, payment terms, things like guarantees for how long, you know, that a lawyer is going to be at a firm. There's those I think are the three most important terms you might find in a recruiting agreement. And that would be the recruiting agreement between the law—like a law firm who's hiring you to be their dedicated recruiter to place a place a certain like "We need somebody for this role, go find them." Yes, that's right. Yep. Okay. And so my question was again… I'm curious so I'm making the observation that what what I am finding is that's the key part of what I think is a lot of the value that I bring is to explain: A, here are market processes, so apart from this tangible recruiting agreement, generally processes for firms have a goal: bring in the best talent. Okay, here's what I’ve observed are the best processes to do that, and some of it is reducible to the mechanics of the terms in an agreement and showing, "Hey, here's why there's there's standard process across firms and here's the benefit to you to comporting to these market terms." And the benefit to you is not zero-sum to the benefit to the recruiter to the lawyer. Okay. I'm curious if you see an analog in your work where you're able to observe patterns across law firms in in and how they structure things like partnership agreements or in terms of how equity partnership is structured—is it lockstep, modified lockstep, etc.? And I'm curious if you have takes on "Hey, like what are fair market terms in partnership groups, what are fair market terms in in law firms that is most effective for for structuring partnerships?"

Hilary Gerzhoy: Yeah, well, so I I think it’s a great question and I think it runs the gamut. I think the what has changed dramatically in just the last like five to eight years is this new class of non-equity partners. Because what it was for so long is partnership was partnership, as in you owned part of the law firm. And so that came with a lot of huge benefits, which is like we all when the firm is doing really well, we all do really well. There's like general buy-in to the success of the firm. Um, and it makes it makes people feel like they're part of a collective and that they have pride in the institution, right? And that like a win for someone else is a win for them too. It’s not a zero-sum game. It’s a we all sort of share in the upside. And then I think now that almost every firm, right? I don't think there's that many Am Law 100 firms left that don't have a non-equity tier. I think that has really changed the way that people who join the partnership sort of feel. It… you become a partner, you're sort of a partner in name only because you don't actually own… you don't actually have, you know, you don't get a benefit from the upside that's a direct benefit of having equity in the firm. Um, and in a lot of ways it it feels to folks kind of like a trap because you are now the only… the only path to becoming an equity partner is to generate a book. But to be sort of viewed as in good standing at the firm, you have to continue to bill at a certain level that makes it really, really hard to generate a book unless you want to like never sleep, right? Like doing business development takes a lot of time and it’s not as though like you just get this whole chunk of time that everyone's like, "Okay, great, you're fine, you're doing business development," right? You're at a at a hugely profitable company, right? If we think about law firms as companies, you're at a hugely profitable company that expects that everybody's contributing. And so the way out for a lot of people becomes… like the way to like the thing that gives you more freedom, which is being an equity partner, feels kind of impossible in a way that it didn't before, right? Like it would be you did your seven or eight years, you did superlative work, now you share in the equity. And and that means that you feel differently about… you don't feel this rush to generate your own business. And if you do, great, but there's plenty of folks out there that don't that are also equity partners and also feel valued. So I think that's a big change that has made it harder for people who are sort of coming through the ranks to feel valued. The other piece to like what I see where there's more harmony among the partnership is more transparency. More transparency about how compensation works. And every and firms do it all they all do it differently in terms of how things are um how factors are weighed in terms of how you get equity. But I think everyone understanding what the process is and having a process, right? Not and making it so that there is transparency not just about what the outcome is, but what the inputs are. Because then people feel like they can change their priorities, right? And so I think one way in which people feel unfairly treated is: it’s a black box compensation structure, the firm says that they care a lot about time that you spend devoted to the firm, devoted to mentoring associates, serving on committees, but nobody ever feels like that’s tied into their compensation. They feel like they're supposed to do it and it's valuable, but it’s not tied to their compensation. And "I think the Jimmy down the hall, he I know he doesn't do any of it and I know he makes more money than me." That so like knowing what truly what the inputs are and the firm articulating what those inputs are and then having transparency around it, I think that's a big driver. Um, I think not having billable hour requirements fundamentally changes a law firm in ways that I ultimately think are so much better for clients too. Because when you have an arbitrary requirement, it makes people feel it it incentivizes people to do things that we do not want to incentivize lawyers to do. Which is to to maybe one lie, right? Say they're they're spending time doing something that they're not, or more often just being inefficient, right? And take because I have to get to this number and if I have to get to this number like "All right, I’ll read that deposition transcript again." That's not in the client's best interest. And so it should be that you do the work that’s needed to get the result for the client and do the A+ product, right? But like once you get there, stop. And when you have the billable requirements, it makes people feel like that's not possible. Because you're always sort of afraid for like what next week looks like. "Well, maybe everything drops off next week, so I got to like keep it up," right? Or in any given moment, like "I've been slow for this week, what does that mean for the future?" And that like creates a sense of panic and urgency that is makes people feel terrible, one, and ultimately I don't think is good for for for lawyers generally. So I think firms I've seen where there really is no requirement um and they but your compensation is tied to your contribution to the firm in a way that that's articulated to you. So your contribution for some firms is just purely what you originate, right? And that can actually make people feel quite happy because they know if I if I bring in X, I will make Y, period end of story, right? That can actually just be very satisfying to people. Or there's other factors, but I know what those other factors are and they feel in my control to some extent. Versus a billable hour requirement for a lot of people does not feel like it's in their control if they're not generating their own work.

Khurram Naik: And then in terms of the structure of equity partnership—in terms of things like lockstep or all the variations there are—do you have any point of view on one um one format that is more conducive to success holistically of the law firm?

Hilary Gerzhoy: I think lockstep works really well when everyone feels like they're they're sort of bought in, right? Like the when when lockstep doesn't work is when you feel like other people you're working harder than everyone else, right? Uh, and you're sort of pulling and you're not making a differential salary to compensate you for that fact. But when it is lockstep and everyone is a hard worker and you feel like your peers and those like in lockstep with you are pulling their weight, I think it works incredibly well because what it does is it basically gives people more runway to actually develop their practice in a way that’s like more long-term successful for them, right? So like you know you're going to this is what the compensation is going to be for these years and then you can decide how you want to spend your time um in terms of how you want to develop business, what expertise you want, uh what relationships with particular clients are going to be really important for you to be take take the lead on—that kind of thing. So I think it works it works really well until it doesn't work, until somebody feels like they they got the raw end of the deal. Um, but a lot of firms are getting rid of lock… I mean, there's very few firms left now that are really doing true lockstep equity. Lockstep for I mean it’s for associates it’s the market is the market, right? And it’s there's some deviation but not very much. And there's actually like incredible transparency about that in the way that in like a lot of professions there's not. Like you can literally look up: "What does a 7th year associate make at an Am Law 100 firm?" And like you will find out. Like I can't I couldn't look up like "Random Fortune 500 company, what does like somebody who's worked there for seven years make?" There there could be like an enormous range, right? But so there's something very strange about going from a place a structure where there's complete transparency and everyone makes the exact same amount of money other than bonuses, which are as a as a percentage a pretty small percentage of your sort of ultimate compensation in terms of differences um to a system where you have no idea what anybody else is making. Um, and and often what like the basis is for what you're making. Because a lot of times with firms too, the bonuses it like if you hit the hours target, then you get the full bonus. And the full bonus is X. But even with the partner like with the equity partner situation, it’s not unless it’s really a you get a percentage of what you bring in, then you sort of have no idea what I worked this amount of hours, this is how much I billed, and like I don't know what the compensation committee's going to tell me I made. That's where most people live, and I think it's not super pleasant. But there are things with… but there are reasons why firms do not want transparency um because it gives them a lot more power to make decisions.

Khurram Naik: And you mentioned, you know, I've seen you previously speak about partnership agreements and some of the somewhat punitive terms that can be in there that don't really come up until they come up, kind of like what you're just saying. And do you think upstream there's any issues? I mean, like what does it speak to something else about the firm—the firms that have these kinds of terms? You know, it’s probably not these these firms that have these other high-quality aspects of of harmony among partners uh even if there's differences in in terms of work product and compensation. Can you speak to the impact of a fair partnership agreement and what are some of the terms you think should be in a fair partnership agreement?

Hilary Gerzhoy: So the vast majority of partners I think don't know what their partnership agreements say. Because when you are offered to join the partnership, the answer is yes. And it’s sort of "Whatever you want me to sign, I'm going to sign it." And partnership agreements can be hundreds of pages long. Um, so I don't think that they impact the culture in anybody's lived experience at the firm until they want to leave. And I don't and in basically any way at all. So like a a really unfairly drafted partnership agreement that has a lot of punitive terms I don't think impacts somebody's day-to-day existence basically at all until the moment that they leave. And so if they never leave, they spend their, you know, entire career at a firm that the firm has a bunch of provisions in a partnership agreement that that would if they knew about them would would be unfair, they have they don't have any ramifications on their existence. The firms that have and like what are the punitive things that we're talking about? One of them the one of the most punitive that I've seen is that your capital contribution can be used to count against your accounts receivable. So if clients haven't paid, that the amount that they have not paid can be deducted from your capital contribution. Capital contributions are supposed to be money that you give the firm for a period of time up until the time that you leave so that the firm can stay afloat and there's not cash flow issues, right? And almost every partnership agreement has a payback period, just because partnerships don't want to be in a position that say 50 lawyers leave and then all of a sudden they can't pay their lease or they can't pay their staff. Um, but there's a payback period, right? But the idea is that you get your capital contribution back. It’s not money that you are giving it’s not a donation. Um, but with firms—and I've seen this, and it’s not super common, but I've seen it a few times—where "If your clients don't pay, we're going to deduct it from your capital contribution." I think that because… and the reason it’s so unfair is because as any practicing lawyer knows, you do not have control over whether or not your client pays. There are some clients that just do not pay. Um, and what's your recourse? Your recourse is to initia- to sue them um to try to collect fees. What's the consequence of that? You will get sued for malpractice. Basically every time I've see- so many of the malpractice cases I see are because you tried to collect on unpaid fees. Because what does a client… a client who’s not going to pay you in the first instance, that's obviously not a client who's being fully, you know, fair. Pro- honest about things. Fair, right? Like you've performed a service, you need to get paid. And if somebody thinks, "Ah, they performed a service but I'm not going to pay them," they may might also be disproportionately the type of person that says, "Well, I'm going to then sue you so that you go away." Um, and so all of that is to say that we have very little control as lawyers over whether or not our clients pay, uh and very little power over what to do if they don't. So that's a that's a harsh measure. But I think the answer to your question is that for in most circumstances, I don't think it really impacts people's day-to-day existence if they have if there are provisions in their partnership agreement that are that are pretty unfair.

Khurram Naik: Well, I know that we're right up on time here and, you know, there's just so much more about, you know, your backstory that we didn't even touch. Um, so we might have we might have to do a round two here. But I think you've, as always, had lots of food for thought for lawyers and um yeah, it’s just super interesting to hear about your practice because as you say, I think you know the having an ethics practice you were talking about the emotional core like "I think I think about things in a job that probably other lawyers or litigators don't." And so yeah, I think you're right about that. So a lot more to mine in that, hopefully in another conversation.

Hilary Gerzhoy: Yeah, great! Well, thank you so much for having me on. This was great.

Khurram Naik: Thanks, Hilary.

In this conversation, Jaimie breaks down why drinking culture binds lawyers to work (caffeine to power through the day, alcohol to shut down at night, repeat), how Gen Z's shift away from alcohol is finally forcing the legal profession to catch up, and why her white-collar defense practice—built on deeply personal storytelling and credibility—made launching Disrupting Drinking feel inevitable. She also shares the trial that transformed her from a terrified junior AUSA reading trial technique books on the subway into a confident partner, why her daughters' wrestling careers inspire her to take risks ("I'm not getting pinned in front of people—much less at stake"), and how she's challenging the story that lawyers have to play it safe with their reputations.

We discuss why listening is Jaimie's differentiator in white-collar defense, how the best advocates frame seemingly preposterous theories ("You've got target and victim in the wrong buckets"), and why she chose speaking over writing a book—because discrete talks let you iterate, get feedback, and build an audience before committing to a manuscript.

Keep reading below for the full link to the episode and the full transcript of our conversation.

Top Insights

Below are the highlights of our conversation:

• Drinking Culture as a Control Mechanism: Jaimie argues drinking in law isn't just about stress relief—it's a tacit way to bind you to work. The cycle of caffeine to get through the day, alcohol to shut down at night, then collapsing exhausted means you barely survive, let alone thrive. You don't have energy to work out, show up extra for family, or pursue anything outside work—so work becomes your only priority by default.
• From Terror to Transformation: The Trial That Made Her: Jaimie's first major trial as an AUSA—representing the government against Bank of America with 3-4 AUSAs facing 100+ defense lawyers, a Brendan Sullivan-led team, and Judge Rakoff's breakneck schedule—was so high-stakes she was reading trial technique books on the subway. But winning that case gave her the confidence to think "I can learn anything, I can do anything" and set the foundation for her partner-level practice.
• Credibility Is the Differentiator in White-Collar Defense: In a field full of excellent ex-prosecutors with similar backgrounds, Jaimie's edge is being earnest, listening patiently, and building trust with both clients and the government. When she advanced a "preposterous" theory—that the government had target and victim in the wrong buckets—her credibility got her a hearing that others wouldn't receive, and she flipped the case.
• Why Speaking Beats Writing (for Now): Instead of committing to a book, Jaimie chose discrete keynotes and workshops—faster to execute, easier to iterate, and you get immediate audience feedback. You can do a dozen talks, learn what resonates, and then write the book once you know there's an audience and you've refined the message.

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Full Transcript

Khurram Naik: This is Khurram with Khurram's Quorum. My guest today is Jaimie Nawaday. Jaimie is the head of Seward & Kissel’s Government Enforcement and Internal Investigations practice. I learned about Jaimie from a post she made on LinkedIn about cutting out drinking and her new venture to disrupt the role of alcohol in the practice of law. I myself cut out alcohol more than five years ago as an associate, so her venture seems to really capture the moment. I think you'll enjoy learning about how a seasoned white-collar lawyer is finding space for entrepreneurship. This is a great episode for exploring the nexus between personal and professional growth. Jaimie, thanks for coming on. I was really struck by your LinkedIn presence. You did something that I've never seen before, which is, it seems to me, took the effort to share your story in a skillfully produced way about your experience with drinking and then choosing to no longer drink, and then sharing that story about your work as a lawyer in this new format. So you have this new business venture called Disrupting Drinking. I was so struck with that, and I'd love to hear a little bit about what Disrupting Drinking is and so we can talk some more about the impact it has on you and what you see for the legal profession.

Jaimie Nawaday: Sure. Disrupting Drinking is my new speaking venture. And it's also just an initiative to get the word out in corporate America about the high-pressure drinking culture, which to some extent has eased in the last few years. But there is the expectation, certainly in law, in finance, in consulting, in law enforcement, in all of these adjacent fields, that the professional world requires drinking, and often drinking hard liquor, in the case of say prosecutors in certain areas of law in particular. I would say especially trial law work and criminal law work, we see especially high levels of drinking and drinking hard liquor. And I sort of was the first lawyer in my family and had a certain amount of imposter syndrome, as we all do. And when you have imposter syndrome, you look around and see what everybody's doing. And in the legal world, that was drinking. And so I really wasn't a drinker before I was a lawyer. But I, you know, started out with wine. And then when I switched to the US Attorney's Office, I noticed that everybody was drinking Scotch and bourbon, and I started drinking bourbon whiskey as well. And over the course of a few years, I just noticed that I was drinking too much too often. It was basically a nightly habit. It wasn't that I was drinking so much at any given time—I wasn't a huge binge drinker or anything like that—but I knew it was too much and I knew I was too attached to it and it was holding me back. And it was hard for me to quit on my own, and I didn't feel like I could tell anyone about it. Certainly, with background checks and things like that that you have at the US Attorney's Office, it just felt like something I had to keep secret. I had to quit sort of through willpower alone. And that was really tough. And so I looked around just in media, on YouTube, in bookstores for stories of people who drank like me and had quit on their own. And I really couldn't find that story. And after I quit in late 2020, I started thinking about how much better my life had gotten once I quit. And I started thinking back on that period of time when I was trying and failing to quit and how a story like mine would have really helped me back then. And I used to just write in my journal New Year's resolutions and things like that, you know, resolve to drink less or only drink twice a week or something like that. And I just kept failing. And I think I would have quit years earlier had I heard someone share a story like mine earlier. So that's what led to Disrupting Drinking.

Khurram Naik: Yeah, so much of that resonates for me. I quit drinking roughly at the same timeline, about a year earlier. And so for me, it was definitely connected to practice. I mean, so I was too broke before law school and in law school to drink much, and then finally could afford alcohol and I noticed my first year was definitely a stressful year. And I was going through like a bottle of bourbon a week and I had the weight gain to show for it and I was just like blown away by that. But so then I kind of pulled back from that and it was fine for a while, but then yeah, in 2019 I noticed I was really in the cycle of caffeine to get me through the day and then alcohol at the end of the night and just the cycle wouldn't end. So then I cut out both at the same time. And yeah, I very much agree with you that there's just not a variety of stories about not drinking. I think first it's very abstract, like when you're in law school or in practice like there's some CLE you go to or whatever they say, "Hey, by the way, you know, too much drinking in the profession." Like, okay, one in three lawyers has an issue with drinking. Like, okay, I get all these numbers but it's just not tangible. And so yeah, I think hearing stories from successful lawyers like yourself to say like, "Hey, like you thrived in government practice, you're thriving in private practice." Hearing stories from lawyers like yourself would definitely change a lot. I'm curious if you think that—how much has changed since the pandemic? You know, of course, there was a lull, I think any number of people were drinking a lot at home. I think there's lots of figures that showed drinking went up a lot, which you know, is not surprising. And then so since then now people are of course—it's been at least a couple of years if not several that people have been getting back together for conferences. Do you think anything—have you noticed a change before and after, pre-pandemic, post-pandemic in terms of how much drinking seems to be part of legal culture?

Jaimie Nawaday: I mean, during the pandemic, just anecdotally, it seemed to be going way up. Just I guess just the way people were joking about it, sort of drinking at a much earlier hour in the day and sort of throughout the day. And you know, people having a lot of wine tastings, like Zoom wine tastings and things like that to socialize. And then I saw just statistics on how much worse problem drinking was during the pandemic and emergency room visits around drinking and things like that. So during the pandemic, it seemed to be getting a lot worse. Then I guess it wasn't immediately after the pandemic, but just the last few years, it seems like there has been a shift because we hear more and more about Gen Z drinking in much lower numbers. Dry January seems to be getting more and more popular every year. I just seem to hear from more and more people now that they've quit drinking or have cut way back on drinking. I notice that the mocktail menus are getting better and better. It seemed like it was really hard a few years ago to find—even in Brooklyn—to find real mocktail menus, and now we have non-alcoholic bars, there are non-alcoholic spirit stores, and pretty much every restaurant seems to have a decent mocktail menu.

Khurram Naik: Yeah, definitely notice that and there are still vestiges of it. I mean, I was at a conference recently, and so my wife was with the conference with me and my wife is pretty clearly visibly pregnant. And so someone—so I—she had seltzer, I had seltzer, someone walked up to me and said, "Oh, are you not drinking out of solidarity?" You know, just the default assumption is that you would be drinking. That that is the assumption is that what you would be doing.

Jaimie Nawaday: Right, and that's especially true at conferences. So to go back to your original question, I think I've seen changes in society, but I think the legal profession in particular is still lagging way behind. I think a lot of firm events, networking events, conferences are still—they're starting as more people are making noise about it and making the requests for non-alcoholic options, they're starting to include them more. But still, the socializing still revolves around drinking.

Khurram Naik: Yeah, I wonder if—I don't think there's going to be any clear answers to why there's this connection between drinking and law beyond the obvious: "Hey, it's a stressful job." There are many stressful jobs. And yes, we have enough income and so to be able to afford alcohol. So there are lots of answers for it. But I wonder if part of—you mentioned I've consistently understood that Gen Z is drinking less, and from my experience with people that are of that generation, yeah, they drink way less. And I'm so struck with it because I know that at that age I was trying to drink as much as possible, and so was everyone else that I knew. It was just a given and an assumption. And so I think some of it has to do with just a general interest in health that is, you know, a secular trend in health, you know, that people are more and more interested in health as we go along. But I also wonder to what extent drinking culture is tied to work culture in kind of binding you to work in every sense. And so, I mean, the extreme version of it is you see this in Japan and I think South Korea as well, where in Japan there's the concept of a "salaryman." And so the salaryman culture is like it's a—from I think the US advantage point—a very extreme culture where you're expected to work long hours for sure, but then also spend a lot of time after hours socializing and drinking a lot.

Jaimie Nawaday: Right.

Khurram Naik: And so probably from seeing something that seems like a more extreme example, you can understand how it works on that spectrum at all. And I think part of—it seems to me part of the history of the reason that drinking and law legal practice was so tied together was to bind you to your work. So it was a way of like, "Hey, like just the same socialization we were just talking about," but then also like, you're not—you're just—you're barely able to get by, right? You don't really—you're not able to thrive, you're not able to—so you're just—you just survive that day of drinking and now like the only thing that you have, you don't have energy to work out or maybe show up in an extra way for family or friends or whatever. So work is going to be the number one priority. So it's like a tacitly perverse way to like bind you to work. But I wonder if you've observed that, because that's something that I've noticed.

Jaimie Nawaday: That's interesting. I mean, it resonates especially in the trial context, I think, because you know, alcohol, of course, it doesn't—it doesn't really reduce stress or anxiety, people now understand. But it feels like it does in the moment, right? For the first hour, first half hour, right? So if you're working long hours at a trial, you're so high adrenaline and your nerves are so high all day long. And what's going to shut that off immediately? It feels like, well, a really strong drink, right? And so you can see how the culture would start is, you know, it's—it's the way you can power down very quickly once you're done with trial prep for the next day. But then you have that and you become worthless very quickly, so you, you know, you go home, you collapse asleep, you just get up and you do it all over again. You're not—you're not going to have—you want to shut down quickly. It feels like the quick fix, but then you're not going to be doing anything else productive. You're not really engaging with your family in any meaningful way, you're not going to go exercise or anything else, you're just going to collapse and then do it all over again, like you said.

Khurram Naik: Yeah. And so tell me about how you're approaching this. So you—you are a partner at a—at a litigation boutique, and so you've got a—a busy practice. How are you working this venture into your practice?

Jaimie Nawaday: Um, you know, I guess around Memorial Day, I just started setting aside time on evenings and weekends. And I'm, you know, I'm fortunate, my kids are teenagers now, so and they get around on the subway, so I don't—I don't spend, you know, all evening having to chauffeur them around to different places. They get around on their own. And I have a super short commute, about 10 minutes from downtown Brooklyn to downtown Manhattan. So I'm—I'm fortunate enough that I have a little more free time than I had when, say, the kids were younger. And just kind of mapped out little by little what it would take. And it felt much more realistic, I guess, and much more compatible with a legal practice to plan talks and workshops, to do sort of a speaking gig as a side gig, as opposed to say writing a book, which just felt much more daunting and would have taken a lot more time. To sit down and draft an hour keynote is a—is much more realistic when you have a full-time job.

Khurram Naik: You know what I also like about that is like, there's just—you don't have any clue like what the demand is for this book. But like a—you know, a talk is something that is—it's discrete and then you can quickly get some feedback from an audience and then learn what resonated in that and maybe you do a dozen of those, a hundred of those. At some point, you will understand, "Okay, let's see, there's a book to be written here." Then—then now I understand there's an audience for it and, you know, some of them have already heard me speak before on this. And then you're also able to like iterate on exactly on—on what we were talking about is just like what people are looking for. And so can you say some more about some of the—the groups that you think would be—your message would be helpful for?

Jaimie Nawaday: Um, I think law students for sure, because we all heard about in law school the rates of problem drinking among lawyers. And I'm head of associate recruiting now at my firm, and so I was—I was at a recruiting event recently at a law school and the—and we got to talking about drinking and Disrupting Drinking also. And a lot of the students I spoke with don't themselves drink for one reason or another and they were saying that they now have law school classes where you get the old "look to your left, look to your right." I think it used to be something like "one of you will drop out of law school," but now it's like "one of you will develop a problem with alcohol." And I said, "In what—what guidance were you given in terms of how to avoid this?" And they said, "Well, we didn't really get any." Just sort of the cautionary tale, the cautionary statistic, that sort of thing. So definitely I think law schools can benefit from this because we're scaring them, but we're not really giving them the tools yet. And I think to hear relatable stories and "here's what happened to me" and "here's—here's what I wish I had known and here's how I could have set myself up for a different trajectory in terms of that lifestyle," I think are super beneficial. Also incoming classes of associates or employees. You know, it's—I mean, I'm a lawyer, so obviously my initial audience is—is lawyers. But people in other industries face the same kind of pressure, especially other long-hour high-stress jobs like, you know, finance is another obvious one, consulting is another obvious one. But I would say it can be bar associations, firm retreats, groups of partners, team-building exercise, you know, wherever you're getting a group of people together in the professional setting, that's potentially my audience. Anybody who cares about mental health, wellness, any of those issues, drinking is tied into that. So if you're getting a group together to talk about any of those issues, I think that's a group that I can add value and speak to.

Khurram Naik: You know, what I like so much about that is the drinking is—there's definitely a key part of it that is solo, but of course, so much of the drinking is in a group context. So probably speaking to a group about, "Hey, here's an awareness for every single person here about the influence of this group on you," it allows all these people to individually and collectively choose different behaviors. And so it just—it's so timely, like you're speaking to them in the moment when it's most—that information is most relevant. It's just-in-time information that's the most relevant to them.

Jaimie Nawaday: Right, and there's, I mean, there's an obvious value proposition for firms and companies because, you know, drinking is just costing them all a ton of money. Not just in terms of actual alcohol that they're spending at events or on after, you know, firm-sponsored after parties and things like that, but just, you know, sick days, loss of productivity, workplace incidents. Almost, you know, throughout my career, every workplace incident I've been a part of on a case or seen it at some, you know, wherever I was, always involves alcohol, things like that. And—and women are so often on the receiving end of that, and of those incidents. And so it's also just important for kind of diversity and inclusion, you know, retention initiatives as well.

The Bank of America trial that transformed Jaimie is the kind of experience Joe Ahmad has had over 100 times. He told me trials are a “risk sport” — if you need certainty, don’t go to trial.

Khurram Naik: Yeah, I—I was searching through my phone through a conversation and I stumbled on an old thread with a former coworker. And so I just was immediately plunged into—to just like, you know, our world years ago. And I was—I was just scrolling through it and just, it was amazing how much, like we were talking about poor behavior of partners and just how much of it was associated with alcohol. It was just—that just happened this past weekend. It was just such a stark reminder of—of the associations you're talking about. Could we talk a little more about—so you mentioned some of the context, you know, for you personally in terms of, "Hey, like my children are a little more self-sufficient, so I—I have some space to take on." Can you say some more about, you know, you've been in—you've been at several firms in private practice, you've been in government practice, so you've had, you know, a rounded professional career so far. I don't know many or I—I'm just not thinking of any lawyers I know that have developed this sort of speaking bureau engagement platform venture. And so can you tell me more about how you came to—you talked a little bit about to say, "Hey, you know, I realized there wasn't a book here, but there was a, you know, a potential speaking opportunity here." I see so little of practicing lawyers doing something like that. So how did you even come up with the idea of like, "Hey, this is a thing, you know, like I can do this, I can speak and—and get paid to speak and add value in that way?" Like, how did you come to that idea?

Jaimie Nawaday: Um, that's a good question. I think some of it was—it was probably a combination of things. I mean, some of it was going to partner retreats and, you know, we—as all firms do, you bring in outside speakers on a range of topics. And so, you know, I knew it was a thing for law firms and elsewhere. And then just sort of seeing public speaking courses and gigs and things like that. I—I must have been talking about it or something because suddenly my social media feed was full of it. And then I started poking around at some of those classes and kind of seeing what the—I wanted to see, you know, what does the market already have in terms of people speaking on this topic. I started looking around on TED talks and other things, and it really seemed like there are obviously lots of resilience speakers, grit, all these wellness speakers, but I did see that there was a gap around drinking. And I thought with my background doing trial work, doing a lot of public speaking, it just seemed like a natural fit.

Khurram Naik: And then what is the—so you saw the opportunity for how your skillset would be valuable to other people. What did you identify as the payoff to you? And of course, it will change over time, but at this—heading into the venture, just I—I want to replicate that decision for anybody else that has an entrepreneurial instinct and looking for, you know, inspiration from what you're doing right now. You know, what was—what was the early value that you identified that you would get out of this?

Jaimie Nawaday: I think it was—it just felt like something I had to do, I think, just in order to be fulfilled. It's very satisfying to me when somebody says, you know, "When you told that story, it had this effect on me. It gave me hope. It inspired me in some way." And I've had that in different contexts. For instance, since I quit drinking over the past few years, I would sometimes post on social media different athletic things I was doing as part of different health kicks, but I wasn't really sharing the drinking part of my story at that point, I was just—I mentioned that I had stopped drinking sort of as part of a health kick or a health challenge. But a lot of people would tell me, "You know, I've been inspired by your social media posts and I started doing this or I started…" and that's always been very gratifying to me, super meaningful, and… and then I was at a conference last spring, it was a diversity conference, and we talked about—one of the panels was on socioeconomic diversity. And there was a panel on that we don't give enough airtime to people who grew up with—without money. Like we're sort of focusing on racial diversity and all these other things that we should be focusing on, but we don't often talk about what it's like to enter the law firm world when you grew up without money and how foreign that world can feel when you don't know the types of food you're eating, when you're not—when you don't feel sophisticated at these fancy restaurants that you go to suddenly as a summer associate and that sort of thing. So I told my story about growing up, you know, maybe barely—we'll say barely middle class in central Pennsylvania and what it was like when I was a summer associate and not, you know, not knowing how to eat the food and what it was and sort of feeling a little bit like a hillbilly. And the—and again, like when people came up to me after that panel and said how much my story resonated, how they felt seen and understood, I just—I just love those moments of connection. Like that's what I enjoy so much about getting up in front of people and telling a story. So just knowing that stories can really help someone change their own lives. And so what I got out—I guess what I saw myself getting out of it was just knowing that I could help someone or give someone else hope because I know what it was like when I was trying to quit and it was just—it was a very scary and lonely place to be. And so if I could help someone else out of that, that would mean the world to me.

Khurram Naik: Where in central Pennsylvania did you grow up? I went to school in Pittsburgh.

Jaimie Nawaday: Oh, I grew up in a small town outside of Allentown.

Khurram Naik: Okay, not so far away from Pittsburgh.

Jaimie Nawaday: Right.

Khurram Naik: Yeah, I think you're right. I think stories are what help people really change their minds. We are really, you know, most influenced by stories and not data, right?

Jaimie Nawaday: Right.

Khurram Naik: And in terms of, you know, you're already exercising skills that you already have from, you know, the public speaking skills are things that you already have. Are there—are there any other professional benefits that you see for yourself from pursuing this?

Jaimie Nawaday: Um, that's tough to say. I mean, potentially, right? I mean, apart from the obvious, somebody can pay me to come speak. But really I think it's a huge benefit to all of us if we start to change the legal industry and everybody feels a little more included and they don't have to stress about "How am I going to navigate this event?" And when I was at this recruiting event recently, some students told me that they've been secretly stressed out about how they're going to navigate the law firm world as a non-drinker. And they shouldn't—they shouldn't have to worry about that. I mean, there's enough stress that you deal with as a young lawyer, just, you know, the hours and whether I make a mistake and a privileged document goes out the door and all the things that you worry about as a junior associate. The last thing you should have to worry about is, "Are people going to—am I going to be held back in some way if people know I don't drink alcohol?" That's just—that's crazy.

Khurram Naik: I think what I really like about this, adding this to the conversation of legal practice, is because, you know, so many interviews you see in, you know, major media legal media publications or bar—you know, if you go to a bar association kind of interviews to do, it's, you know, fairly formulaic about the career decisions that somebody makes. And so it's just based on the analytical qualities of one option or another. Like you and I could—could jump in that right now. You and I can ask you, "Well, tell me about, you know, why you went to Seward & Kissel and tell me why you went to the US government." And those are definitely a key part of, of course, the career decisions we make is, you know, some analysis of the payoff we're doing right now talking about Disrupting Drinking: "What's the payoff?" So yes, these kinds of things are part of our careers for sure and helpful to share. Um, but what I like what you're doing is, you know, you've identified drinking as this nexus of all these different forces in law and all these different—so I mean, like why do we drink? We drink, you know, in key part to relieve the stress of the kinds of work we're doing. Okay, what—what is stressing you out? You just said, "Well, okay, like am I going to blow some privilege issue? Or, you know, am I going to…" You know, just like, "I—I'm—I'm really worried about this brief and there's only—there's only so much I can spend time on writing on it." And so it's a juncture point to say, "Okay, how are you practicing? Is there some other way that's better to practice? Is it inconceivable the only way to practice is pressure, pressure, pressure, do an amazing job?" Like there's got to be other ways that we can relate to each other and get excellent work, meaningful work. And so I think it is a useful touchstone to—to hit on a lot of areas of fulfillment and excellence in the practice. So I think there's… yeah, I think adding this will really be I think very enriching for just getting people to have conversations and take pressure off and figure out other solutions for what's really driving this behavior of drinking. Well, I think it would be helpful for a little context for your practice to understand how you got here. And—and of course, you know, talking about experiences you had with drinking could be relevant to that, too. Um, but I guess we can start with going into government. Could you talk a little bit about why you went to the US Attorney's Office? Like, what were your goals heading into this and—and talk about some of your experiences there? Because you mentioned—you mentioned in the context of drinking that was kind of a, you know, you felt like you're joining a new culture and, you know, wanted to fit in. Um, so tell me—tell me about that—that change, because you were already in private practice, exposed to that world, found a new world in government practice. Tell me about the differences that you saw between those two worlds even as an experienced litigator at that time.

Jaimie’s journey from barely middle class in central Pennsylvania to leading a BigLaw practice resonates with Patti Burris, who had two kids and an associate’s degree before she started the path to law school — and ended up at the top of her class.

Jaimie Nawaday: Yeah. Um, I guess I thought about—I'm not sure my early stage career choices were the most thoughtful. I think a lot of it was, right, opening up the Vault, looking at rankings, and then you know, somebody tells—you know, or having certain mentors who said, "Here's what you need to do, and you need to go to this type of firm, then you need to go to the US Attorney's Office, then you should make partner." And so I sort of marched through Law Review, clerkship, white-shoe firm. Um, then I decided I need to go to a different firm to get more kind of stand-up-and-argue experience. So I changed firms with the eye of going to the US Attorney's Office. And you know, some people have really great stories about why they chose to go to the US Attorney's Office. I think mine was less thoughtful. It was, "This is kind of what people who I respected had done and suggested I do." And it sounded really cool, and so I thought I would—I thought I would give it a try. And when I got there, I mean, it was—it did feel sort of like a dream come true getting the job. And I was just immediate, you know, you show up and you feel like you have so much responsibility right away. I started on the civil side. I was in the civil side and then I later moved over to the criminal division. But you start and you just have no idea what—how to do anything. I mean, you're assigned all these cases, you don't really know the first thing about kind of running your own case start to finish. I was a mid-level associate at a firm just before that, but you still, you know, you get very specialized in firms very quickly, you're kind of doing the same things over and over again. And suddenly you're kind kind of running the whole show. You're almost like a solo practitioner when you join the US Attorney's Office. And um, you know, the camaraderie's great, but I think one of the most stressful things at first is you go into court, the judges are very hard on you. They tend to defer to the government a lot. You have a lot of credibility when you walk into court, but the—the trade-off there is that they're holding your feet to the fire constantly and they feel like they—they have to. And so you feel, you know, inexperienced, a little bit bumbling, you get screamed at a lot by judges and—and it—it's hard, you know. I'd go back to my office and cry. I mean, every—every junior AUSA has that experience of walking into court, um, getting blasted for something or other. Maybe it wasn't even something that was their fault, but whatever it is, like the government is always responsible. You learn early on that you have to take responsibility for everything. And so there are a lot of very humbling moments, and then you go—go back to your office and you beat yourself up again and again and again, at least I did, and a lot of people do. And—and then you look for a way to kind of clear your head from all of that. And so we would have, you know, Scotch Fridays, we, you know, liquor cabinets or—file cabinets full of liquor. And we'd break it out and we'd tell stories and that was kind of the way of decompressing from the week, you know, telling the war stories from the week, telling the humiliations of the week, bucking each other up. Um, and—and in a way that's—that's kind of how the hard drinking started.

Khurram Naik: And then what was the experience of being in government that transformed you as litigator? Like, what was, you know, you went through this experience and you came out on the other side. What was different about Jaimie at the end of that experience compared to the beginning of the experience?

Jaimie Nawaday: What was different was, I would say, my first major trial when I was in government was so high stakes. It was a case against, um, it was a case against Bank of America. And it was before Judge Rakoff, who's known for moving cases very, very quickly. And it started as—as a qui tam, as a whistleblower case. And the government often gets a very long time to investigate whistleblower complaints, especially against a large financial institution, because you could imagine that takes—it could take years to do an investigation like that. I was given six months to investigate before I had to make a decision to either resolve the case or file suit. So six months of investigation, and then we filed suit against the bank and Judge Rakoff set the trial date for less than a year from the filing of the complaint, which is extraordinarily fast for a civil case of that size. And I later found out that we had—they were something like… we knew that the—that the team on the other side was large just based on the number of attorneys on the docket, but of course, there was an army of lawyers behind the attorneys on the docket as well. And so at our largest, we briefly expanded I think to five AUSAs on the case, but typically we had a three-to-four AUSA team. And we had roughly 100 lawyers on the defense side. And so we were, I mean, we were just unbelievably outgunned. We had this impossibly fast litigation schedule. And so there was absolutely no room for error, because we had numerous experts in the case. If an expert report were not done properly, if the sampling of the—the case dealt with defective loans, we had to sample loans and evaluate them—if the sample size was not drawn correctly, there would be no time to redo it given the pace of discovery and how quickly the trial was approaching. So I worked just the most grueling hours of my life for that really entire year period. And I—I just remember being nervous all the time because so many of the things that I was doing for that trial, I was doing for the very first time. And it was my very first trial. And I was against Brendan Sullivan, who is this, you know, he represented Oliver North in the '80s, he's this huge giant of the DC bar. And leading up to the trial, I was reading a book on trial techniques on the subway, like how to lay a foundation for a question. Like the basics of trial practice, and I thought, "This is so crazy." And this—not everyone at the US Attorney's Office has an experience like that, where it feels like you feel so inexperienced and you're against such experienced lawyers out of the gate. But you have this dramatic moment where you're like, "This is—this is how you grow up as a lawyer. This is how I became an adult lawyer, and this is when I developed the skills that carried me forward." And after that point, I felt like, "Okay, I can—I can do anything, I can learn anything." It might be scary, but I made it to the other end. We won the trial and it was a completely transformative year for me professionally.

Khurram Naik: Tell me some more about that because you enter, like so many lawyers, into government. You enter as an associate and you've come out as a partner. What is that transformation? Can you say some more about like, you know, it's—it's… I don't think it's as reducible to say like, "Hey, a mastery over the Federal Rules of Evidence" or something like that. Like, what is—is it some attitude in you, some—some perspective that, "Hey, like," I think you were just saying it, you know, that "I can—I can take on any problem"? That's some of it internally to you. And then what is it, you know, that firms in assessing you are looking to see to say, "Yes, you are in fact a partner"? You know, I'm sure it's not reducible to how many trials you had or just anything quantitative like that. What do you think is that quality or—or what do you think, apart from this trial, like what was the inflection point in you in terms of how you saw yourself and approach work? Is there something you can speak to that that's just different that somebody else can assess?

Jaimie Nawaday: Yeah, I think it's—I think a lot of it's just a confidence game. I mean, there's—there is a certain level of experience, skill set, obviously that's going to be a necessary component in that, but it's never sufficient for somebody to regard you as a partner, of course. I think it's really having that confidence and being able to inspire that confidence in others, where you can command a room and you can tell the client, "I can handle this for you. Here's what I propose to do. Here's the result I believe we can get," and you inspire that trust and confidence. I think that's—that's what firms look for in making a partner.

Khurram Naik: And then were you active in the white-collar bar as US Attorney, or did you get active in that after you became a partner?

Jaimie Nawaday: After I left.

Khurram Naik: Is that common? I don't—I don't know if it's common at all for US Attorneys to be part of white-collar events, or maybe they'll speak at them, but I'm not really familiar with—with the level of…

Jaimie Nawaday: Right, it's typically people in the defense bar, but they'll have sometimes some supervisors from the US Attorney's Office sometimes come and speak or attend select events. But they're—but they're not often there because a lot of times we're talking about the challenges of dealing with the government.

Khurram Naik: We had talked a little bit before about the white-collar bar and, you know, I practiced in a—in a pretty small bar, the Hatch-Waxman bar, which is like a subset of patent litigation. And so um, there's a lot of advantages to being in a specialist bar. Um, but I'm curious to spend a little more time on that because I think um, it was very interesting um to learn about the nature of the white-collar bar and the work. Um, I think it'd be exciting for a lot of people who are earlier or—or somewhere in the middle of their—of their experience to start thinking about how they fit into that. Um, so can you talk a little more about, you know, compared to your commercial litigation counterparts down the hall, you know, what are some of the differences that you've observed in the white-collar bar versus commercial litigation?

Jaimie Nawaday: The commercial litigation bar is just much, much larger. So I think you—they're fewer—you don't have the repeat player factor the way you do in a smaller bar like the white-collar bar. So your reputation just follows you much more easily in the white-collar bar. You have a lot of repeat players. Um, prosecutors will always ask, you know, if somebody come—when I was an AUSA and somebody calls me up and says, "I represent so-and-so, you know, can we talk about this case?" I would always look them up. I would see were they in the US Attorney's Office, I would ask my friends about them. "Do you know this person? How are they to deal with? Are they credible?" Right? You want to know is this—should I give this person a meeting? And if so, how much time should I give them? Are they going to try to play me? Are they going to be straight with me? That sort of thing. So your reputation really matters. You want to deal with people fairly because you are a repeat player with the government, with your fellow defense counsel in a joint defense group, things like that. You—the joint defense group only works if the fellow members of the group trust you to share information with you. And if they're sharing information with you, you can better advocate for your client, obviously. But in the commercial litigation context, I mean, sometimes you have joint defense agreements, but it's just such a sprawling bar that I think it's… you can get away with being sharp-elbowed um for a longer period of time.

Khurram Naik: Can you say some more about that dynamic of what it is that a—a white-collar lawyer can engage the government on to learn about, you know, and then what are some of the gamesmanship involved that you're looking to avoid? Tell me some more about that dynamic because I think that's, for people outside of white-collar practice, I think that's um kind of a black box. They don't really understand, "Like, what is there to learn?" You know, like for myself I only did commercial litigation, so there's a complaint, it's a publicly filed document unless it's, you know, there's something, you know, that needs to be redacted or whatever. Um, but broadly speaking, it's a public process and transparent in that way. So can you speak some more about, you know, what it is that these lawyers are looking to assess and—and tell me some more about how credibility and um reputation play in—in both among members of—of the—of the bar and then between the government.

Jaimie’s decision to launch Disrupting Drinking as a speaking venture — building a business around her authentic voice — is similar to what Sunny Kim did after quitting BigLaw. Sunny now teaches lawyers how to build personal brands by combining vulnerability and insight.

Jaimie Nawaday: Right. So especially if you are primarily doing investigations, which is what I do, so the whole game is to prevent somebody from getting charged. Because once your client is criminally charged, they already suffer—even if they go to trial and they prevail, right, they've already suffered so much reputational damage. And so that's really what especially white-collar defendants generally want to avoid is getting charged in the first place. But when you're at the investigation stage, there's no discovery that you can engage in. If you—it's such an information game and the only way you're going to get information out of the government at that stage is basically by having a relationship, having rapport, convincing them to just voluntarily share information with you. They don't have to share anything with you at all. So I can call them up and say, "I represent Jane Doe in this matter, you know, what—what can you tell me?" They might just say, "Well, you know, we can't really share anything at this point." And I can't—I can't force it. Then that's—that's where we are. I go back to my client, they're not going to be very happy. Like, "What do you mean? You can't—you can't tell me anything at all that they're looking at?" Or, it can be, "Well, Jaimie, let me tell you. We've, you know, we've spoken to a lot of people, we think your client's in a bad spot and here's why and blah, blah, blah," and share all this information with me um to just give me a sense of the strength of the case. And they can say—they can do what's called a reverse proffer where they call you in, especially if they want to resolve the matter in some way. Uh, they can call you in and basically share, you know, in detail the evidence against the client, which allows you to then consult with your client and make a much more informed decision. They can say, "All right, we'll do a reverse proffer and then we're happy to hear from you." Some sort of counter-presentation of why you think that we shouldn't charge. And again, they don't have to allow you to do that. They typically will allow that as a courtesy, especially if you are an alum of that US Attorney's office. It's sort of a professional courtesy that they would extend. But all of those little things, it's kind of um as, you know, just a system of—of courtesies that they don't have to allow, but they will allow if they think you're not going to abuse the process, if they think that you are a credible person um and you're not somehow going to twist it against them. So that's why all of those little things just—they really matter, especially if the government is pretty dug in and you want to go in and tell them, "I know you guys have spent a year on this case, but here's why you've got it all wrong and here's why you shouldn't charge." Right? Like, that's—that's a pretty big ask because, you know, there's sunk costs and all of that that—that might be at play at that point. Agents can be very dug in, even apart from how the AUSA feels about the case, and the agents can be pushing the AUSA really hard. So you just want everything that you can get that will allow for you to get additional information out of the government and for the government to give you a fair hearing before they make a charging decision.

Khurram Naik: What's the payoff to a US Attorney for sharing this information? So, you know, I'm in private practice, I'm looking for the government to share some information. How do I frame it for the benefit of the government to share that information?

Jaimie Nawaday: Um, if they're—I mean, for a responsible AUSA, they—they want to get it right, too. I mean, some people can just be hyper-aggressive and dug in no matter what. But generally, they want to get it right and they don't want to be embarrassed. They don't want to charge a case that's going to blow up in their faces. And so if they think you have something that will allow them to reach the right result, that's—that's in their interest, too. Right? The flip side, but, you know, cynically, I mean, sometimes they might want to know their weaknesses to see if they can then make their case stronger, which is why some people don't like to share a lot of information on the defense side with the government because their view is, "Look, they're—they're just—whatever holes I poke in their case, they're just going to plug through other means and then still bring the case."

Khurram Naik: Sure. Yeah, then the same commercial litigation analogy might be rather than deposing a witness and, you know, making clear like the reason—you're just inferring the fault lines that you're trying to establish for that witness, just examine them at trial to, you know, to show right then and there, "Here's the weaknesses with this person's credibility or theory."

Jaimie Nawaday: Right.

Khurram Naik: So then um, there—you know, so you—you return to private practice and um you're part of a small bar, but there certainly is competition among your peers. How do you differentiate yourself? So what—what has differentiated your approach compared to other peers with comparable experience?

Jaimie Nawaday: Hmm. I—I mean, I'm not sure I've ever done anything intentionally to sort of pitch in—in terms of as compared with my peers from the US Attorney's office. Like I can't think of a pitch where I've said, "Here's why you should hire me instead of so-and-so," you know, somebody else. And I don't—I don't tend to pitch in white-collar defense work anyway. Um, I think because I guess what I—what I've always said to clients is it's just a very personal choice. There are lots of excellent white-collar lawyers out there with very similar and—and I think this is true, with very similar backgrounds, right? There are lots—I mean, the US Attorney's office is a very big place. There are lots of us who come out every year with great credentials and I think ultimately the decision for a client is, "Do I feel comfortable with this person? Am I going to be able to share everything I need to share with this person so that they can really advise me? Do I trust their manner, demeanor, messaging that I think they can properly represent me and represent me the way I want to be represented?" Right? And for everybody, that's going to be different. Some people want a softer approach, somebody want—some people want like bulldog from start to finish. And that's just going to be a personality fit.

Khurram Naik: It sounds like that is highly unique to that—like I can't think of another practice that's so personal in that way. And it makes sense, right? Because so many of the people that are charged, you know, this is their liberty is at stake here, their credit, their reputation, which as we say, you know, even if a charge isn't proven, it just—it still has a stain. Um, and yeah, so it makes sense that it's an intensely personal process then. So um, I guess and that means that you're probably leaning in more to yourself and—and how you are as a person. You know, there's just probably such a nexus between your personality and your practice. So can you say some more about what is your personality then? When—when somebody is considering, you know, you mentioned maybe one person's a bulldog, one person isn't. Okay, those are different dimensions. What is it you think that people tend to be drawn to you and—and really resonate with you on?

Jaimie Nawaday: I think um, I think people find that I really listen to them. And I think that's—that's really important, that I will listen patiently to their account of what happened and think very, very hard about all the angles in terms of how to message to the government. And so I think people often want a lawyer who really listens and understands their perspective. Um, and I think that people find me earnest and credible and they expect that the government will view me the same way and that—and that judges view me that way as well, that I'm straightforward and candid and that that—that if the same things come out of my mouth that come out of someone else's mouth that might be a little bit less trustworthy or be regarded as a little bit less earnest, that obviously I—I can be a more effective advocate for them. But I would say it's—it's really just being myself, that they connect with the fact that—that I will listen to them, I will take their strategy ideas very seriously as well and I will package them as—as earnestly and effectively as I can.

Khurram Naik: I can tell that you do that from this conversation because if I ask you a question, you'll pause, you heard me, you're thinking about it, and then—and then you're willing to say, "Oh, I hadn't thought about me some aspect of this" or whatever. So that really tells me you are listening to me. So yeah, I—I find that effective. You mentioned storytelling, um, and so I'm thinking of I—I did another podcast interview with Neil Chatterjee, who's a patent litigator, um, he's had a number of jury trials. And so he's been on both sides of the V in patent litigation. And he says, "No matter what side of the V that I'm on, um, my position is that we are always representing the innovator. Like, we are always going to tell a story about how we are the innovator here." And so are there principles of storytelling that you have for your clients that—so that's a story that maybe a jury would find persuasive: "Like, okay yes, that's the innovator and that's relevant for this legal cause of action." Are there patterns of stories that you find helpful for the government for um persuasively, you know, seeing your—your client in a beneficial way?

Jaimie Nawaday: Um… yeah, I—I mean, there are. I'm sort of hesitating to say it because I think, "Well, if somebody from the government hears this, are they going to think then this is—this is somehow a ploy? This is just her pattern." But I would say I have had a number of cases in recent years where I was—I was advancing a theory and a message that on its face would seem quite far-fetched. Um, where it was—it was essentially a version of the "you've just got it all wrong. The person you're looking at as the target is really the victim here." Some version of that story. But I 100 percent believed that that is what happened. And I had success in turning the government's view based on just building, you know, receipt by receipt why that was the case. And it took some time. But I would say even though it was sort of a seemingly preposterous theory to advance to the government, right, to tell them, you know, when they think they're rarely wrong, "Like, you've got it all wrong and you have the wrong—you have target and victim in the wrong buckets here," uh, that would also be something that would be very embarrassing to get wrong to the government. And so I think in those cases, my credibility really helped that I got any kind of hearing at all in those cases.

Khurram Naik: You know, it also seems to me that, you know, reflecting now on the nature of your work and how much it is about doubling down on your persuasiveness and authenticity, it just seems like in that context it almost seems obvious, Disrupting Drinking. Because I mean, just like that is just, you know, you by profession are somebody who deeply personalizes stories and contextualizes and says, "Hey, this is a real person's life at stake here," and then um helping the government understand what's at stake for this person and—and what they—what they did or didn't do. Um, so that sense, like these like hyper-personal stories that are persuasive, like it just—it just seems, well obviously that—that would be helpful for you to do that in other contexts too. So just, do you see a connection between your approach to work and how you're thinking about communicating through Disrupting Drinking?

The fear and imposter syndrome Jaimie describes — adopting drinking norms because she felt like she didn’t belong — connects to Hilary Gerzhoy’s core observation that fear, not greed, drives most professional missteps among lawyers.

Jaimie Nawaday: Yes, yes. I'm not sure I did before you said that, but I think I think that's sort of… yeah, I mean—I mean, now that you've said that, I think that's almost a theme through my life, sort of stories that I grew up on that really impacted me or just sort of the power of storytelling through my childhood. Because um, my parents—I grew up in a pretty religious household, and so you know, my parents really wanted us to read the Bible and stuff like that. There was, you know, church every Sunday, so I had sort of that world of Bible stories. On the other hand, my father was really into pro wrestling. So I grew up really on like the stories of the Bible and the pro wrestling, right? And in some ways, like both of those kind of came together in my trial work, too. Sort of the concept of showmanship and the good versus evil narratives and all of that. And I think—but I think that's sort of the power of storytelling, as I'm reflecting on it, that's—that's been kind of a theme of my life.

Khurram Naik: I was just picturing in my head like, and then Vince McMahon the begat, and then just, you know, going through that list of begats for that family. Um, yeah, that's—uh, yeah, I think um… so I guess I'm curious now, in this stage of your career, what story about yourself—it sounds like historically you've challenged stories about yourself or the stories that you accepted from the world. Um, can you share some of those stories that you challenged over time? Like, what were some of the stories about yourself and how you fit in that you challenged? You mentioned, you know, in terms of fit, fitting into, "Hey, like I'm now in the world of big law as a summer associate," so so maybe there's some stories there, um, and then some stories that you had for yourself, you know, heading into the US Attorney's office and making sense there. Is there—are there in these different eras of your life, can you think of stories in the past that you challenged then found a—a new story on the other side of that?

Jaimie Nawaday: Yeah, I mean, I think—I think the biggest one was I grew up um just temperamentally I'm very shy and introverted. Or—or was, growing up. And some of that has faded over time, but you know, I just would—I just avoided public speaking wherever I could growing up and—and really through college, you know, dropping classes that required speaking or trying to skip if it—if it was a high participation class. And even—even early in my, you know, I tried to kind of fight through it in—in law school, tried to participate and things like that. But because I sort of had this feeling that I could be good at trial work, but I was just was so petrified of public speaking. And I would, you know, battle just not just nerves, but like nausea and nightmares and, you know, really felt kind of phobic about public speaking. And when I was a junior associate and we had a mock trial exercise at my first law firm, and my partner mentor said, "You should—you should really do this, it would be great for you." And I said, "Okay, I'm going to do this." And then I just got so wound up with nerves that I just sort of told the program organizer, "I can't do it. I'll do it next year," whatever, I made up some excuse, "I'm too busy," and just sort of dropped out of it. And I could tell my partner mentor was disappointed and I thought, "All right, well, I guess that's it, you know, I'll never be a trial lawyer, I'll never go to the US Attorney's office," and I just thought, "I'll just be a quiet behind-the-desk lawyer, I guess that's—that's what I'm meant to do." And then I don't know, and then I—I can't really think of a clear pivot point, but I just decided, "You know, well what if I just—what if I just did it anyway? What if I just kind of got over it? What if I just applied and did it little by little?" And of course, you know, that's—that's all it takes. And the first time I did an oral argument, I was up most of the night with nausea and was, you know, worried about my voice shaking in court and all that. But I got through it and the adrenaline on the back end was so great that it sort of made all the nerves worth it. And I think that's when I then started to get hooked on, "Okay, I'm—even though I'm much more outgoing now than I was as a kid, I, you know, everybody battles nerves with public speaking, but I—I guess I just—I see the reward. I see the reward both in terms of connecting with the audience and how meaningful that can be, whether it's jury or law students or whoever, but also just that—that excitement and that adrenaline on the back end is so, so satisfying."

Khurram Naik: You know, it's interesting because I also have always historically, I have thought of myself as being very introverted, and through—I just—I was just talking to my wife this weekend about how funny a profession I've chosen as a legal recruiter, because um, I—I'm on phone calls all day. As a litigator, I'd just be—I'd have my door shut mostly and just be working on whatever discovery issues or briefs or whatever, just it was very solitary. I enjoyed connection through, you know, bar associations and that kind of stuff, um, but I was uh very solitary historically and not—didn't have any training beyond tons of phone calls. So I'm just on tons of phone calls all the time and it's um and it's intensely social in that way in a way that um I—I don't consider myself to be an extroverted person who um… and then you know, my role also involves um persuasion, uh sales. And so that also is—is… I'm not natural to those things at all. I'm not like a charisma-driven person who just naturally is, "Oh, of course, that person's in that function." So um, I—I have also had to—to work, I've chosen to—to work inside, but I'm really proud of myself for doing that. Um, and it's funny because you mentioned connection with your audience, and that's a really interesting takeaway from public speaking because it could be very surprising to think that, right? It's a very distant experience where there's a public speaker, audience, and there's a very separateness, and you're speaking to this general large room and your voice is booming and it's just—it's a one-way street largely. Um, but I, you know, in my history going back to say even high school, I found that even though I was and then way more introverted, I have always enjoyed public speaking because of what you just described, is that intimacy. And so I should also add like, hosting podcasts, this is a one-on-one conversation. This is like probably my favorite, two or three people is like my favorite format for communicating, uh for really understanding other people. And but yeah, I've found that public speaking is a surprisingly good way to do that at scale where um it wouldn't seem obvious that an introvert could really enjoy public speaking, but I—I think that's what you're communicating, that you've experienced that as well.

Jaimie Nawaday: Right. Yeah, because you're talking really to a bunch of individuals at the end of the day when you're in the moment in public speaking. And what you look for is that—that recognition on someone's face when they go, "Oh," you know, when you see a little bit of an emotional shift in them or something resonating, and it's—and it is like you're back having a one-on-one conversation.

Khurram Naik: So we're talking about stories and—and how we challenge those stories over time. So today, what is the story about yourself that you're challenging?

Jaimie Nawaday: Hmm. I guess that I'm not exactly sure how to frame it, but I think as lawyers we're very often safety seekers and sort of, you know, reputationally conservative and all that, sort of concerned what the market will think, what people will think, all—all of those sorts of concerns. Um, and I feel like I've—I've sort of dropped that, and I kind of had to drop that in order to do this whole project. And some of it was just—it just sort of felt like the next chapter of my life. And I've been listening a lot to—I don't know how I got into this—but I started reading and listening to death doulas, who are just like birth doulas but they, you know, they guide people basically in hospice who are getting, you know, are very near death. And they're very positive people and they have all these great life lessons about, you know, what people say at the end of—of life and what their top regrets are and things like that. And one of the top regrets that comes up again and again that this one death doula mentioned is that people say, "You know, I just wish I hadn't cared so much what everyone thought." You know, I cared so much what other people thought and I was never authentic as a result. And—and I think as lawyers, it's—it's very easy to be like that. We're in such a conservative profession and it's not like I've just thrown caution to the wind or I don't care what anybody thinks, but when faced with a choice of "I can do this thing and maybe there—there will be some reputational blowback," but there really A) shouldn't be, and B) whatever is the blowback to me, I am 100 percent certain that this can help other people. And so I'm going to make the choice to help other people. And I don't know that I mean in—and I have a certain amount of luxury, I'm at a point in my career where I can do that too. You can't ask somebody who's up for partner to make the same choice. It's just not realistic. But if those of us who are sort of in leadership positions now in firms can't do that, can't share these kind of stories, then who can in the profession? Really no one. You know, do we have to wait until we retire to tell these kind of stories? That seems really unfortunate and doesn't send the right message. I want to be able to say, "You can share this story and the world, you know, an anvil won't fall on your head, your clients won't run out the door, everything's fine. We can have these conversations and it's so beneficial to the industry."

Khurram Naik: Yeah, I really like that. I think the North Star of, "Hey, as long as I'm being helpful, there really can't be any risk in that," is—is a great message. And then I also think it's a great message that um this can be this incremental approach, this isn't—this isn't all or nothing. Um, and yeah, I think, you know, in your role, it could cut in both directions where people could feel they have a lot to lose now. "Like, hey like, now I've worked—I worked so hard to become partner, and now this is the thing I have to lose." So I actually think you deserve um recognition for that, that you are—you are taking this step in a phase where others would actually I think um could choose or—or maybe we've even observed choose to—to be more conservative about it. Um, yeah, I felt for myself, you know, I went to a law school that uh Big Law recruits out of and I ended up in Big Law and always felt for myself that was such a blessing for me because I didn't have the attachment to that identity uh that other of my peers… Like if I went to Harvard or Yale, I—I could imagine all the pressure I'd be putting on myself based on my peers, based on my perception of myself to say, "Hey, why did you do that thing? Why did you achieve that credential? It was to—for this narrow set of options for you." And so um, yeah, I think there's a lot of of um gratification for removing identity. Um, there's a—a writer and investor Paul Graham who—who talks about, he's got a great essay, I think the title of the essay is "Keep Your Identity Small." And uh haven't read it in a while, but I—that's my recollection and takeaway of it is, is the fewer things that you um connect yourself to… Um, I think Bruce Lee also talked about this in Jeet Kune Do. I think that's the—the empty fist he's referring to is if you've got a knife in your hand, you do knife things with it, but if you have an empty hand, you can do anything with it. Um, and so on that topic, I saw that you are also part of a board for wrestling. I think it's encouraging women to wrestle. Can you—can you talk some more about that? Because that also seems pretty iconoclastic, um, and uh tell me some more about your—your role in that in—in your advocacy for—for women's wrestling.

Jaimie Nawaday: Yeah. Um, so I—I mean, I love strength building overall for women. I just find it very physically empowering and I like lifting weights and have tried since I quit drinking, did different um like a—kind of women's fight camp in DC and some Krav Maga and stuff like that. And—and raised my daughters in CrossFit for a while and then we—we tried different sports, but I think that gave them some early strength and confidence. And my older daughter was having—she was like 13, 14 during COVID and was having a pretty tough time like a lot of teen girls were. And initially I got her some—she had mentioned before COVID about trying boxing lessons. And so I got her some boxing lessons with a female trainer and she very quickly like I noticed a—a change in her after just a couple lessons. It seemed to really be pulling her out of, you know, some of what was bothering her during COVID. And then when she started high school, I encouraged her to try out for the wrestling team. And—and she got on and it completely transformed her. I mean, she—she had some talent in it, but she loved just this crew of women who were all, you know, obviously all different body shapes and sizes because you have all these different weight classes. So it sends the message of "you can be strong and powerful and athletic in a variety of sizes, not everybody's trying to be 100 pounds or 110 pounds." Um, she's, you know, taking pride in her big strong legs and stuff like that. She's not, you know, when I was growing up in the '80s everybody wanted to have like thin thighs and stuff like that, and this was a whole different mindset that I thought was so positive. And she just changed, you know, just the way she moved through the world was different. She just started moving through the world with such confidence. And so my younger daughter who's now a sophomore in high school, she ended up when she got into high school trying out for wrestling as well and had the same experience with it. And I've just—I've just watched it, the effect it's had on both of my daughters who were also super shy and introverted just like I was, like really take on this both physical and social confidence that they didn't have before. And the wrestling, the girls' wrestling community is just—it's just an incredibly empowering place. You know, it's like there's so much nonsense that teen girls have to deal with in terms of, you know, looking a certain way or whatever, and I feel like wrestling is such a great antidote for that and such a confidence builder. So um, so I got involved with Beat the Streets, which is a um it's a nationwide organization. I'm involved with the New York chapter and it—it's basically a free wrestling club um for um middle school and high school wrestlers around the city. And they have just fantastic coaches and a fantastic community and that's why I wanted to be involved with it.

Khurram Naik: Yeah, I guess what—first thing I thought about, I mean, it's obvious because we're talking about a handful of things so I'm going to connect it to other things you're talking about. But I—I'd also be curious there if there's some connection between your experience with that organization, which is taking a new message for a group of people to say, "Hey, like, you know, maybe historically women have not been in wrestling, but hey, this is really beneficial for all these different reasons for how it influences how women, girls think of themselves." Um, that, you know, maybe you just at least tacitly got, "Hey, there's new ideas and new ways that we can present um new ways to relate to each other in these communities that are about uh improving ourselves" that, you know, maybe had some foundation for you for—for for ideas in this in Disrupting Drinking.

Jaimie Nawaday: Right. Can you say that again?

Khurram Naik: Well, it's possible that, you know, picking up ideas for new ways for people to relate to each other in this one community where just the benefit was pretty clear, but it's a new story. It's a new story for women in wrestling, so that's a relatively new story. That there's ideas from there that's influenced you to say, "Hey, you know, maybe there's new stories in my practice that I can share and help people relate to each other a little bit differently."

Jaimie Nawaday: Yeah. And I mean, I—to be honest, I also am just super inspired by—by watching them wrestle and watching these girls wrestle in general. Whenever I feel nervous about something, I often think about it. I think, you know, what—whatever, whether it's starting Disrupting Drinking, sharing my story and "Oh well, what will people think and what—what might be the fallout," and I think about my kids just stepping in this circle for physical combat about somebody and they often wrestle boys too, you know, somebody who is bigger and stronger than they are and knowing, "I—I'm probably going to lose. I'm probably going to get pinned" or whatever in front of all these people, but I'm just going to fight my heart out no matter what. Like, that's—that's incredible. And that's so moving to me. And I think, "Yeah, I can—I can take this risk."

Khurram Naik: Yeah, no one's coming for me physically.

Jaimie Nawaday: Yes, much, much less at stake. Uh, not getting pinned in front of other people.

Khurram Naik: Right. Well, Jaimie, thanks for coming to share your story. Uh, it's really—it's really admirable what you're doing. I think it's very interesting, I think it's very compelling and uh it's early days for you, so it—I'm really excited to see where you take this and where else you take uh your story in your career.

Jaimie Nawaday: Thanks for having me.

In this episode, we dig into the decision to switch to the other side of the v., how Vishal researched the opportunity by interviewing dozens of lawyers before launching, his approach to building a national trial practice on referrals alone, the unique collegiality of the plaintiffs' bar, and how he thinks about case selection, co-counseling, and the business development strategy that keeps his firm growing.

Keep reading below for the full link to the episode and the full transcript of our conversation.

Top Insights

Below are the highlights of our conversation:

• Research Before You Leap: Before launching Shah Litigation, Vishal interviewed 35 to 45 lawyers and compiled their lessons into a single document. He collected their challenges and failures so he could preemptively address them in his own business plan.
• Cash Flow Is King: The most memorable advice Vishal received was "cash flow, cash flow, cash flow." He structured his practice with roughly 60% contingency and 40% hourly or flat-fee work so that money keeps coming in while the bigger contingency cases work through the system.
• Referrals as the Lifeblood: Every single case at Shah Litigation has come through a personal or professional referral. Vishal sees each referral as more than a business lead. It is a personal vote of confidence that carries social obligation and trust on all sides.
• Case Selection Over Volume: Shah Litigation turns down roughly 95% of intakes. Vishal evaluates cases on the merits, the defendant's profile, and whether the plaintiff can tell their story convincingly. Quality over quantity is the foundation of the firm's approach.
• The Plaintiffs' Bar Is Uniquely Collaborative: Unlike the defense side, plaintiff-side employment lawyers freely share case law, brief drafts, and mediator recommendations. The driving principle is that rising tides raise all ships, and better outcomes in one case create precedent that benefits everyone.

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Full Transcript

Khurram Naik: This is Khurram with Khurram's Quorum. My guest today is Vishal Shah. Vishal is the founder of Shah Litigation, a plaintiff-side employment law firm. I've been friends with Vishal for years and he and I both launched businesses at the same time. This is a really unique opportunity to hear how a biglaw lawyer launched a plaintiff-side firm. We'll dive into the business and the strategy of the law firm. So if you have any interest in launching a law firm or are just curious about how that works, this is a great one to listen to. So here's Vishal.

Khurram Naik: Vishal, you're one of my good friends and so I am very happy to have you on here because your story is very compelling and we both started businesses at about the same time. And so I've been excited about your growth. You've been cheering me on and so I am really interested in diving into how you're running the business of your law firm, the business of law. And we'll get to that and your approach on litigation as well. But first I want to start with, you are, would you say you're a good old boy from Alabama? Is that fair to say?

Vishal Shah: You know, good old boy comes with certain connotations so I might not accept that but I'm definitely a Southern boy at heart. I'll definitely agree to that.

Khurram Naik: Okay. So I want to hear how a Southern boy from Alabama ended up in Boston with his own law firm.

Vishal Shah: Yeah, well, Khurram, thanks for having me. I'm really excited to be here and to speak with you just about my journey as I've gone through this whole process. And you know, coming from Alabama, I didn't really have a choice. My parents moved there for their business. I grew up there. I spent the first 26 years of my life in Alabama in a small town called Dothan. And just before that, a town called Eufaula, which was about an hour away. And I had an incredible childhood. I lived in a community where there were a lot of South Asian people, believe it or not. And my parents were heavily ingrained in that environment and in that community. So we were heavily ingrained and involved in that community. And a lot of it was family but there were other folks too who have become really, really close friends of mine over the years.

Vishal Shah: And when I was probably 14 or 15, that's when I really decided that I wanted to be a lawyer and I was really interested in it. Not because anything in particular had happened and that I really was driven to the law. But it was just always something that interested me. I loved courtroom scenes, watching Matlock, watching movies where lawyers were on TV. And I thought it was a neat job. And so I always told my parents I want to be a lawyer.

Vishal Shah: And so I went to undergrad down South, went to law school down South. And then after I worked at a place for about a year, a small litigation boutique in Birmingham, Alabama, I moved to Philadelphia for work at a firm called Drinker Biddle. It's an AmLaw, I think 100 or so firm at that time. And I was doing commercial litigation within the insurance space. So life insurance policies, long-term cash insurance policies dealing with litigation surrounding those. And worked there from about 2015 to 2017 and close to that 2017 timeframe, I decided that I wanted to change.

Vishal Shah: And I had a friend who was working at Morgan Lewis. He's actually still there now in their employment group. He was also a commercial litigator like I was. And we were just talking about potential opportunities over lunch one day. And he recommended that I apply. I never wanted to be an employment lawyer. I'm not specifically drawn to that field by any means, or I wasn't at the time. But it was litigation. And I knew I liked litigation. Morgan Lewis certainly has an incredible brand. And there are some great lawyers there. And so I made the leap and was at Morgan Lewis from 2017 through 2023. And then in 2020 moved from Philadelphia to Boston for a variety of reasons. But I've been in Boston since 2020 and it's been fantastic. It's certainly much, much different than small town Alabama.

Khurram Naik: Well, so I'm imagining that at some point you became aware that, of course, I'm sure you recognized early on, hey, it's unusual to be South Asian in Alabama. And yes, it sounds like there's a community there for sure. But what would you say now that you're in Boston, you were in Philadelphia before that, urban areas with plenty of diversity, maybe plenty of South Asian lawyers certainly in Boston. What would you say in your trajectory shaped your worldview in a way that maybe some of your peers who grew up differently didn't experience? I grew up in Texas the first 10 years and from there in New Jersey, went to college in Pittsburgh, and both high school and college were very diverse with a large Asian population. What would you say is different about your worldview?

Vishal Shah: There's probably two points to that. One is that I am what I'll call stupidly optimistic. I realize that there are risks in certain things, but I try to look at the positives and try to focus on the positives more than anything. And the second piece is that we as people certainly have way more similarities than we have differences. And so I think at an early age, that was something that I believed in, and I still believe in it today. But that sort of approach, that stupid optimism and this view of having more similarities than differences, I just jumped right in. I played sports, I was really active in school, I had friends come over, I went over to friends' places and just really tried to make my life for what it was. I didn't view it as a Black thing or a white thing or a Hispanic thing or an Indian thing. It was just the way life was. My friends would come over, we would play, and we would hang out when we got older, and it was just part of growing up.

Khurram Naik: So tell me about the path that took you from, you know, Morgan Lewis, a very strong labor and employment defense-side firm. What took you to jump to the other side of the v.?

Vishal Shah: So my plan since I was in law school was to always be a partner at a biglaw firm. That was my goal. And ever since before I graduated, that's what I was working towards. Getting the right sponsors internally to say your name in the rooms that you're not in, getting the right exposure to clients and other opportunities so you can elevate and build your brand both internally within the firm and externally. And then the third was having the right clients.

Vishal Shah: Partnership, especially at a place like Morgan Lewis, timing plays a big part of it. The clients that are your key clients as you're coming up, where are they from a business perspective as it relates to the firm? Are they one of the head companies giving a lot of work to the firm or has the work dwindled over time? And I think that's a really important thing. And so I was always trying to make sure that I had a diverse set of clients that, no matter what happened, I could bulletproof the timing issue as much as that was in my control. And a lot of it wasn't.

Vishal Shah: And so in the summer of 2022, I had had a number of really awesome successes. We had won a two-week jury trial in an eight-figure employment case in Delaware against a lawyer from California who was probably one of the best trial lawyers I've ever seen. And it was the first case I was assigned to when I started at Morgan Lewis in 2017. It's one that I handled from stem to stern. It was me and the partner primarily doing the work for five-plus years.

Vishal Shah: And so in that summer, we won the jury trial at the beginning of June and then within two or so weeks, I received a decision from a federal court where we had won a motion for summary judgment, which basically says, hey, judge, there's no disputed facts here and given the law, we win. And it basically ended the case right there. And it was a case that we were not expecting to win summary judgment on. And so the client was ecstatic and I was on a really, really professional high.

Vishal Shah: But we know that life isn't just all peaks, there are valleys that come with it. And so just two days before I got the summary judgment decision, I learned that two close family members had passed away. And that happened on the same day at the end of June. And then that was kind of very surprising. But then we had two more deaths in the next two months.

Vishal Shah: So in the beginning of August, my cousin's daughter, a super smart young woman who was traveling on a study abroad trip in Costa Rica, had an unfortunate accident and passed away. And she was just incredibly full of life, incredibly hungry for changing the world and making it a better place. All these idealistic ideas that you have, and she was going after it and she was super, super capable.

Vishal Shah: And then within a month, my first cousin who I was extremely close with passed away from an unexpected heart attack. He's much older than I am. My family has a wide range of ages on both my dad's side and my mom's side. And he was a very successful businessman. He was just starting to enter into what I'll call a cooling-out period where he was going to start traveling more and doing the things that he really wanted, but he wasn't able to. It was just all sort of tragically taken away from him when no one expected it.

Vishal Shah: So when all of this happened, we're now mid-September of 2022. It just so happened to coincide with the end of the fiscal year at the firm I was at. I was well beyond my hours requirement because of the trial, because of the summary judgment briefing. And so I decided to take a short leave. And I wasn't in this state where I thought I needed the time. I wasn't feeling down or depressed. I could still focus. I still had the same hunger. I could still do the same work. But something inside of me said, just take some time. Take a couple of weeks. It's not going to change anything in the grand scheme, but you might be in a state of shock and you need to just have a little time where you can think and sort of process what's just happened to you because these kinds of things don't happen often. And you want to make sure you appreciate them for what they are and not just breeze past them, because that would have been my other natural tendency.

Vishal Shah: So ultimately I took the time off and during that two weeks, I started thinking about where my priorities were, where they should be, and where there was alignment. And I realized that I no longer wanted to spend 80 hours a week on the road bouncing from airport to conference room to hotel and back. I wanted to do something where I was in control of my destiny more than anyone else.

Vishal Shah: And so this leads to the next obvious question on why plaintiff-side employment law. I didn't wake up one day just thinking, hey, I should start a law firm today. Nobody does that. Well, maybe some people do, but nobody I know has done that. And it wasn't like that for me. I started thinking about the various things I could do. I could go in-house, which is what most of my contemporaries do after they leave firm life. But I know that I love to litigate cases and I love to go to trial. So I knew that in-house would not be the right fit for me. I could move to another law firm, but I quickly realized that the same set of challenges would exist at any law firm in terms of being at a certain place at a certain time or having others in control of your destiny.

Vishal Shah: And so that was an option. But then I started looking at the plaintiff side and I knew a few people who had made the leap from the management side to the plaintiff side and they were doing great. They were enjoying it. They were practicing law at an extremely high level. And look, I had been trained by one of the best employment law firms in the world. And if I could leverage the training that I got to help level the playing field for individual employees, that was really neat. And I could try cases, I could do things the way I wanted to do them. And so I just quickly started to learn more about it.

Khurram Naik: Can I ask you something about going back to the realization that you want to have more control? Is there something about the other experiences you had with your family members that made you reflect on your trajectory? Like, you mentioned your cousin who had success professionally and then was now looking to shift to experiences and focusing on himself and other things that are important to him. And then that got cut short. Is there something about that discrepancy that influenced you to say, hey, it's really all about control for me? Because I'm trying to understand where that motivation for control over your destiny came from. You were doing well at the firm, making great progress, had a huge win that was tied to your hard work. So what was it? That system was working just fine for you. Tell me some more about what went into that realization that there was a values gap for you.

Vishal Shah: Well, I think I quickly realized that life is short and you might have your own plans for what you want your life to look like, but the universe will punch you in the mouth and tell you what your life is supposed to look like, whether you like it or not. And when I was facing these experiences, I realized that I could sketch out the next 5, 10, 15, 20, 30, 40 years of my life, but if I don't take some active control of that, it may not ever get there. Oh, and by the way, I might not see tomorrow. Anything could happen.

Vishal Shah: And so I think by understanding the fact that being at a big firm, there's a lot of institutional parameters that you're living by and navigating. And things don't happen in terms of what's best for you. Things happen in terms of what's best for the firm and what's best for the brand. And so when we were talking about having the right clients at the right time, that's something out of your control. But if the client that you've invested and poured hundreds of hours into for years suddenly gets a new GC and they change their law firm and they go to another law firm, well, what's your business case then at that point? Now, none of that happened to me, but I realized that I wanted to drive my career more than riding the bus of the biglaw brand.

Khurram Naik: Okay, yeah, that's helpful. Okay, so then fast forwarding, realizing that, hey, this skill set that I have from the defense side is going to be very good on the plaintiff side. What did you do then? What was the next step? You had this realization. What was the step from realization to action?

Vishal Shah: Well, it went into a deep research period and there are really two parts to that. I would read articles, I would listen to podcasts about just the business of having your own law firm, how to start, what does marketing look like, what does client acquisition look like, all of those things. And then I would speak to other lawyers and just vet my ideas and try to use them as a sounding board to get their real thoughts about what it would look like to start a firm. Do you think this is a good idea? Do you think it's a bad idea? For the people who had already started their own firm, I wanted to learn from them. What would you do again? What would you not do? What is something that you wish you knew when you started that you know now?

Vishal Shah: And I collected all of that information from about 35 or 45 different people and put it into a document. And then I just started bulletproofing all of those things. And so it was really helpful to kind of get everybody else's challenges and then try to navigate them in my own approach. And I thought that was super helpful. And it helped me frame out a really decent and solid business plan for when I started.

Khurram Naik: All right, so tell me, give us the insights. What were the key findings you made from those conversations?

Vishal Shah: I still remember vividly sitting on a Zoom call. A plaintiff's lawyer in Alabama told me, when I asked him what was the most important thing you wish you knew when you started that you know now, he said cash flow, cash flow, cash flow. You got to make sure that every month there's some money coming into the firm because that's what keeps the lights on.

Vishal Shah: And it made a ton of sense. My practice, most plaintiff-side practices, and I'm talking about personal injury or employment, a lot of it is focused on contingency cases. "We don't get paid unless you get paid" type of advertising that you see all around town. But I took on a good segment of hourly and alternative fee work and maybe even some hybrid work that could help some cash come into the firm as some of the bigger, more lucrative contingency cases were working through the process.

Vishal Shah: And so by having these two tranches of matters, the ones that you're in for the long term and then the others that are short-term engagements where you're in and you're out but they're continuing to have some money flow, I think that was really, really helpful. And money is a necessary tool. It helps alleviate a lot of stress on a business owner because when you're not worried about where the next paycheck is coming from, you can focus on how to do things the right way and how to do things in the way that they should be done. And I think overall that provides for a better experience for everybody. I don't want to be flippant and make it sound like money doesn't matter. It is super, super important, but when you're not worried about it, it gives you the freedom to focus on things that really move the needle.

Khurram Naik: So what were other strategies that you considered at the time of launching? What were some different jumping-off points that you vetted in that period of time, and what was kind of the consensus on how to start?

Vishal Shah: Well, one of the first questions I would get when I told people I was starting my own law firm is, well, how are you going to get clients? And that is the first question my dad asked me, that is the first question most people asked me.

Vishal Shah: And so there are a number of ways to skin the cat. You have folks who are marketing in traditional ways, think billboards and radio advertisements, commercials, things of that nature. You have folks who are using the internet and they have Google ads and other ad campaigns going on as well as search engine optimization or SEO where they're trying to make sure that their firm comes up on the first couple of hits on Google when somebody is searching for their type of law firm. Both of those require a lot of money.

Vishal Shah: And so when you're starting a firm, you have to be very smart about where you're spending your dollars. For me, number one, I didn't have the infrastructure to deal with a high volume of intake calls. And number two, I didn't want to spend a lot of money getting it set up, at least initially. Now we will start doing that at some point, maybe not the billboards, but certainly the Google ads as well as the SEO. But that stuff takes a good amount of foundational investment from the firm and we weren't prepared to do that at the very beginning.

Vishal Shah: And so we trusted our network. It could be a personal network, it could be a professional network in terms of people that I know, but it could also be something like LinkedIn where I'm connected to so many people just because I've met them at a conference and then we've just stayed in touch or they've come across my profile and we've connected that way just through an informal Zoom or whatever the case might be. So I think client acquisition and marketing was a big piece of what I was focused on in those early days.

Khurram Naik: And then what about the potential strategies for subject matter? Did you know it was going to be specifically employment litigation or did you consider other options, and what was the consensus for you on how to approach that?

Vishal Shah: I wanted to eliminate variables to the extent that I could. I'm not a personal injury lawyer. I've never handled a personal injury case on the plaintiff side. And I certainly could learn it, but should I learn it? Should I spend the time to open my practice up to a different area? And for me, the time-value proposition wasn't there to learn a different area of the law at that stage. So I wanted to focus on employment law. I had that background coming from a place like Morgan Lewis. I had the training and I thought that there was a real value that I could provide to folks because I've seen it on both sides now. And I think being able to look at something from all angles really gives you a great perspective. And so that was why I stuck with employment law.

Khurram Naik: And so is there anything about the early days and how you thought you would build the law firm that your perspective today has changed on?

Vishal Shah: You know, nothing is coming to mind immediately. I think there is a significant amount of investment coming back into the operation side of the law firm itself. We are always thinking about how do we improve the experience for our clients. What makes it better? What removes obstacles to communication? Because I think the number one complaint that individuals have who hire lawyers is that they don't hear from their lawyer that often.

Vishal Shah: And so we have a really robust, awesome legal practice management software called Filevine. It's incredible and it's super customizable, which is really great. And everything that we do is run through that, from cases to administrative to payments. We're now working on putting together a client portal so clients can just log in and see where cases are, see where their matter is from time to time and what's coming up. We've also just signed up to revamp our entire intake system. So it's a constant focus on how to be better, how to improve, how to reinvest and just make the firm as operationally sound as we can.

Khurram Naik: And so what makes you, I guess we're diving more into the business of the law firm, which I think is really valuable. There are plenty of outlets that will talk about the substantive aspects of practicing law, but I really appreciate how we're diving into the business side. So how did you know that now, at this stage, you should allocate resources, time, and capital to the website and building out your SEO presence? How did you make that determination?

Vishal Shah: It's all an iterative process. So I knew when I started that we would be as lean as possible. This is an entrepreneur's story, a small business owner's story, but I didn't even sign up for Westlaw when I first started my firm because that comes with a significant cost. And until I was making some money, I didn't want to just sign up for something that would be a constant overhead cost. But I did sign up for something called the Social Law Library here in Boston, which for $455 a year, as opposed to a month, you can have access to Westlaw, LexisNexis, a bunch of different online resources. They've got a ton of books that you can check out. And I thought that staying lean in those early days was really, really smart. I think within two months, I realized that this is ridiculous and I don't need to be traveling downtown every week to go research. And so I quickly bit the bullet.

Vishal Shah: But that's just one example of how we started off lean and then did what we had to do. And then as we progressed, as we got some more matters under our belt and resolved them successfully, we just took those funds and started putting them back into how to improve the firm. So it's always been a plan to do it iteratively.

Khurram Naik: And so with the work you take on, if you think of it as a portfolio, you broke down this concept of a portfolio of contingency cases versus cases that are alternative fee or some sort of hourly fee. Do you have a rough rule of thumb for how much you want to have in terms of the breakdown between those in any given month? I recognize it changes month to month. No one can say I want exactly 20% this and 40% that. But do you have a rule of thumb for how you're allocating your time to those different kinds of work?

Vishal Shah: Well, once the cases are in, it doesn't matter whether it's hourly or contingency. We work up the cases according to our standard. And that doesn't change just because of the way that the financial model is structured. But in terms of the actual breakdown month to month, I like to do 60% contingency and then 40% on the hourly or flat fee side. And that shifts depending on what's coming in and what's going out, a lot of which is not in my control. But ideally, I think that breakdown is a solid one because you still have money coming in every month. And you still have tremendous upside in those contingency cases because it's just an investment. It's an investment in that case that you're putting in "free" time into until the case is resolved, if it's resolved.

Khurram Naik: And help us understand the financials. How would you help someone who's prospectively thinking about this wrap their head around the financials of a law firm and what you can expect?

Vishal Shah: You can start a law firm today for very, very little money. There's only a handful of things that you really need. You need the correct corporate structure for your given state. You need to make sure your bar licenses and whatnot are active. Malpractice insurance, which even if your state doesn't require it, you should get it. And actually you should also get cybersecurity insurance, but that's a topic for another day.

Vishal Shah: From a financial standpoint, there's not a lot of money that is outgoing if you don't want it to be. You can be lean if you want to. And then you just need to decide, well, based on the value that you're offering, what types of clients do you want? And how are you going to structure those engagements with them? For me, it's easy. It's a litigation-focused practice. It's either contingency or it's hourly, flat fee, or some sort of hybrid among those three options. But if you're doing something different, like counseling work or IP transactions, it's just really thinking through what the folks coming to you need and then how you offer that in a way that makes sense so that people want to go to you when they need legal advice.

Khurram Naik: And then apart from the breakdown of contingency versus hourly, is there some other way that you're thinking about how your work is structured as far as diversification goes? Are you thinking about having diversification of clients geographically or in different industries? How do you think about that aspect of your business? Because it could be a risk to say, hey, I focus all on Boston life science companies and that's my expertise. I don't have the expectation that employment lawyers focus that specifically on an industry, but I'm using that as an illustration of the risks of being specialized in one area where there's a downturn and you're really tied to it. How do you think about that?

Vishal Shah: Yeah, on the management side, there's certainly that specialization where you're the IP tech transactions lawyer within a particular industry. That certainly exists. On the plaintiff's side, you have people who niche into certain practice areas. They might be medical malpractice lawyers. They might be toxic tort asbestos lawyers or they might do employment law. And even within employment law, they might focus on wage and hour laws that are available at the federal level and sometimes state level. Or they might do discrimination cases where there's federal law but then certain states have their own law too.

Vishal Shah: I don't have a certain specialty in terms of only taking wage and hour cases or only taking discrimination cases. I take on cases that I think are really strong. And we are not a volume shop. We will never be a volume shop. That's not our goal. That's not related to our vision in any way. So we look for strong cases and there's a very rigorous process that we go through where we're looking for certain key indicators of a case. We're looking at the merits, of course, and making sure that it meets the elements and that it's going to pass certain stages within the litigation where it could be challenged.

Vishal Shah: And ultimately, if it passes that summary judgment test that we were talking about earlier, if I think that there's going to be a way for us to survive that, that's a great marker for me. That's something that I really focus on and love to have in all cases and really strive to have in all cases.

Vishal Shah: The other factor is who is the actual defendant? Who is the company? And where do people view them within just normal day-to-day living? Right now, given recent events, the insurance industry has not really been looked upon kindly. And so that might be a defendant where you want to think about external pressures as you're going through and evaluating a case.

Vishal Shah: I also look at the individual plaintiff themselves. Is this a person I like? Is this a person that I would go and have coffee with? Is this a person who can tell their story convincingly? That doesn't mean that they're the nicest person ever or that they're all warm and cuddly. They might be kind of prickly too. But are they telling their story in a convincing way? And is this person likable? Because ultimately, what you're going to ask a jury to do is believe your client over a whole host of defense witnesses and defense employees who are going to say your client is a liar, a cheat, and a thief. So thinking about the cases that we're bringing as a whole is really impactful because it needs to meet those markers for us to take it on. Otherwise, it just doesn't make sense.

Khurram Naik: And so you're focusing more on the quality of the case and not so much on any sort of prospective specialization. Do you expect to ever specialize, or is that a product of what's come in the door today? Do you think there could be a payoff to focusing on, say, wage and hour work or something like that?

Vishal Shah: The answer is I don't know. I do a lot of sexual harassment and assault cases within the workplace. I do a lot of discrimination cases of any type, whether it's race, gender, disability, any of the protected characteristics. And I do a lot of cases involving pay practices of companies, whether they're paying folks the right way or paying them on time the way that they need to be paid. So those are the three buckets of expertise that I have. And those are the same types of cases that I handled at Morgan Lewis. Handling them for so long, you get some insights and trends into how these cases are worked up. And I think that's really helpful.

Vishal Shah: Would there be a day that I branch out into the personal injury world or into civil RICO cases? Yeah, maybe. I think if the right opportunity presents itself, I'm always open to that. And I'm not necessarily wedded to only being an employment firm. The firm is called Shah Litigation. It's not called Shah Employment Law. And so the vision is for it to be nimble and be open to any opportunities that come along.

Khurram Naik: So on the topic of Shah Litigation, tell us about litigation. Tell us about how you're approaching, you know, switching yourself from biglaw defense lawyer to plaintiff-side trial lawyer. How is that process of self-education and training coming along?

Vishal Shah: So this is the absolute best part of the job. Litigation and preparing for trial is what I absolutely love. And as it relates to litigation, I see it as something that's far more nuanced than just filing complaints and going through the typical process of most cases.

Vishal Shah: Employment, aside from your health and your family, is the most important thing to most people. It represents a person's dignity, their sense of purpose, and often their entire identity. I think we all have folks that we know whose profession is really their personality. And so for us, every case that comes through the door represents someone's life story, their professional journey, and it's usually a pivotal moment in their career, and it's a moment that, if they're reaching out to me, hasn't been a pleasant one.

Vishal Shah: The way that I approach litigation reflects this understanding. I think many firms on the plaintiff's side take what I call the assembly-line approach to cases. They're filing similar complaints with slightly modified details and they're just going through the motions. We have a completely different philosophy. We believe in something called strategic precision. Think of it like a chess game where every move is carefully calculated and considered. It's not just considered for the immediate impact of that move or the next move. It's considered within how it shapes the entire trajectory of the case. If we take this position, how does it affect these other five things that we're not thinking about?

Vishal Shah: And so it's really using, by the way, the same approach that the really, really good defense firms use. And that's one way where the training hasn't changed. I still absolutely love the nitty-gritty details of a filing in terms of how to make it look polished. And that's something that I've just taken from biglaw that was really important to some partners that I worked for and it's become important to me. And I think it reflects well on the firm.

Vishal Shah: But going back to our litigation process, before we even file a complaint, we are really diving deep into the intake process. It's something that I call a blueprint for each case. It's the pre-litigation analysis that we do. We're looking at documents. We're talking to folks who we think matter. That may be an expert, that might be a witness. And that helps us understand the actual human story. It helps us understand what are the dynamics going on between these people at this workplace. What are the facts we know? What are the facts that we don't know? What should we be asking for? It just gives us a bigger holistic view of what's going on.

Vishal Shah: And I think when you couple that with legal research and you can identify theories that have landed and stuck with courts, I think that really makes the difference in employment cases. And this process might be a little surprising to people. I haven't looked at the exact numbers yet, but we turn down like 95% of the intakes that come our way. And that's not because we're some big bad exclusive firm. It's about being effective. When we can focus our resources on what we need to do for that particular case, it is a much better outcome for everybody. And I would much rather focus my time on a handful of cases than have hundreds that I'm trying to corral and just trying to get to the next stage. That's not really how I'm geared.

Khurram Naik: And so as you're thinking through these cases, how are you doing research to figure out how to position them and find precedent for cases that are really on point? Because it seems incredibly fact-intensive. How are you researching cases based on those kinds of fact patterns to really build the case? I'm assuming part of the diligence is, hey, what sort of legal precedent is there for prevailing under similar circumstances. So maybe you can speak to what drives your approach in finding that alignment of precedent.

Vishal Shah: The good news for employment cases is that there are many, many jurisdictions where the law is very similar. Now the way courts interpret that law and the way judges implement it can be different from jurisdiction to jurisdiction. But at the federal level, you have a ton of laws that apply in every state. And then some of those states have state-specific laws that largely track the federal laws or they might be more protective. Like Massachusetts, where state law is super protective on discrimination, retaliation, and harassment issues for employees.

Vishal Shah: And so there is a lot of law out there, a lot of circumstances factually that could be similar to the ones that we're evaluating. We're looking for key terms, just doing general Westlaw research. But a lot of it is also just discussing the issues with other lawyers, other plaintiff-side lawyers. And I do it with plaintiff-side lawyers and management-side lawyers. It doesn't really matter to me what side of the v. you're on. I just want somebody else's take to brainstorm how we attack a certain issue that we're facing. Whether that's at the intake stage or something that comes up later, it's usually just trying to leverage the resources that you have, whether that's Westlaw or people.

Khurram Naik: Tell me more about the people component, because I think running your own business can be very lonely. And then also, your biglaw friends are just not going to understand the process you're going through because they haven't experienced it. So how are you finding a network of plaintiff-side lawyers or other business founders to run these ideas by?

Vishal Shah: It's funny you say that, because when I left my old firm, my mentor said, when you go out on your own, it's going to be lonely. Make sure that you find times to meet with other lawyers and go to lunch, go have coffee, go to dinners, do all of those things to maintain a social professional life. And I took those words to heart because that guy is one of the smartest, strongest lawyers I've ever met. His name is Steve Wall at Morgan Lewis. And when he told me that, I took it to heart.

Vishal Shah: And so I try to go have coffee or lunch or dinner or grab drinks with people just to check in. It serves a dual purpose. One, it helps me stay top of mind whenever an employment issue comes up for a plaintiff. That's kind of a secondary piece of that. The other one is the social interaction piece of it. I really like hanging out with folks. And so meeting with people, learning about what's going on with them, bouncing ideas off of them and getting some insight is really, really helpful.

Vishal Shah: So aside from having these one-on-one meetings, I will also try to go to bar association events, South Asian Bar Association. We have a Massachusetts Employment Lawyers Association, MELA, and then there's a national level as well called NELA, National Employment Lawyers Association. And I'm really involved with those as well. So I'm going to conferences and trying to meet people and make sure that you're not on this solo island of one.

Khurram Naik: Yeah, I think that sounds very essential. And then tell me about referrals. What role have referrals played in the business, and how do you think about that channel of client development going forward?

Vishal Shah: So I mentioned earlier that we don't do any traditional advertising and we don't do any internet advertising or SEO at this stage. So what do we do? We focus on our network. Referrals play a massive, massive part of that. They are essentially how I've gotten every single case that I have ever had at my firm, through somebody that I know who has said, oh, you have an employment issue, you should talk to my buddy Vishal. He's an employment lawyer and he can possibly help or direct you in the right place.

Vishal Shah: So referrals are the lifeblood of my firm. That's how we operate. That's how we get cases. I don't expect that to ever change. I hope it never changes because to me, a referral is an even stronger connection to the client and your network than any of those other methods we were talking about. Because number one, somebody that they know, like, or trust has had an employment issue and they have thought of you as the person to help resolve that issue. And so there's a personal feeling of responsibility there. Oh, Khurram has referred his buddy to me, I need to do a good job for the buddy and I need to do a good job for Khurram because he's my boy. And like you said earlier, we've gone through this entire business-building process basically walking in it together. So I hope it never goes away. It's a vital source. And that's what we are always trying to focus on, making sure that referrals and the networks stay alive.

Khurram Naik: Yeah, that makes a ton of sense. And for my business, referrals are enormous. It's just like you say, there's that social connection and obligation that creates this triangle of obligations that everyone is aligned on in making this a success. And it's also just gratifying to help people that you know or people in your network.

Vishal Shah: Well, look, I think we all have moments of self-doubt and we have moments of fleeting thoughts, and maybe not so fleeting thoughts, of, can I really do this? Did I make a huge mistake? And I think when people you know send you cases because they trust you to be able to handle it, that is reassuring. And it does more for me personally and mentally than it does for me financially. Because oftentimes a referral doesn't even play out into something that's actually generating revenue for the firm. But every referral, regardless of whether it's a legit case or not, is a stamp that, hey, I trust you, I trust you to take care of my buddy, go do it. And I know you can do it. And maybe that's not what they mean. Maybe it's more simple than that. But that's how I like to think of it because it helps me sort of process and keep going. Because for the reasons you explain, it can be lonely, it is somewhat like an island at times. And so to look for those little bright spots is really, really important.

Khurram Naik: Tell me about personal satisfaction. You're talking about both servicing the client and the professional competence of taking something to trial and prevailing. Those are two sources of gratification. Then there's the money. That's another source of gratification. So three sources. How do you think about those? And would you ever counsel someone that a strong reason for launching your own firm is for the income potential? Is that itself a reason to do it?

Vishal Shah: I think that it can be extremely lucrative if done the appropriate way. I think plaintiff-side practices in general are feast or famine. There are people who are scraping by to make it month by month. And there could be multiple reasons for that. And then there are folks who are really, really crushing it because there's a method to their madness in terms of how they go about litigating cases and how they handle them.

Vishal Shah: I've been really fortunate to see how some really great firms litigate and I've just taken those tools and put them in my pocket. I used them when I was at Morgan Lewis and then I use them now. And so I think learning from others can be really important in terms of how you're going to drive your own business. But I would never just say, hey, you should go be a plaintiff's lawyer because there's a ton of money to be made. There is money there, but there are easier ways to make money, and I think the money is not always there because it depends on a lot of circumstances that are outside of your control.

Vishal Shah: For example, I was vetting a case last month where everything looked great. What happened to this individual was extremely terrible and they had suffered a lot of both financial and emotional damages. The defendant would have not been a likable company, neither would the lead wrongdoer. But that company was not doing well financially and they were about to file bankruptcy. And so even if we took that case and worked it up all the way for three or four years and put our very best foot forward as we do in all of our matters, there may not be any money at the end of the road.

Vishal Shah: So there's a significant amount of risk, but I think if you're thoughtful and methodical and smart about your approach, I absolutely think that there is a way to make more money having your own firm than you would ever make at a biglaw firm.

Khurram Naik: I'm curious about mindset shifts in moving from largely billable-hour work to larger contingency work, because as a legal recruiter our work is contingency as well. You only make money upon placements. And so I've observed that a misapprehension a lot of lawyers have when you're at a big firm is you're largely getting paid by the hour and you're getting paid to do hard things. And so the skill in your work as a lawyer lies in your ability to prevail despite bad facts, let's say.

Khurram Naik: As a legal recruiter or anyone working contingency, the hard work you're doing is in finding outstanding people to work with that have strong credentials, a strong story, who are accomplished people that law firms are excited to work with. That's the hard work up front, getting that talent. And then when you have that talent, things are easier from there. There are still challenges on the way, like talented lawyers can have very particular needs, or maybe they're in a really strong position and really getting a firm to meet them requires skill in negotiation. But largely the challenge is getting the very best talent and then things are easier from there.

Khurram Naik: But what we don't do is take the edge-case person where the story is really hard to tell. Maybe they've made a few moves and you can maybe help the next firm understand why they need to make one more move, or maybe their credentials aren't very strong but they've got really strong experience. But that's a much harder road and you get paid the same either way, whether you take the outstanding candidate that's easy to explain or the person with a really hard story to tell. So you don't take the harder case, which I think is really counter to how litigators think, where it's like, hey, I'm getting paid to take on really hard facts. Have you encountered any challenges in transitioning from that billable-hour mindset to a contingency model?

Vishal Shah: Yeah, look, on the management side, the benefit is it doesn't matter what the facts are. They could be absolutely terrible. You're getting paid every single month. Bills go out, bills get paid, your salary is coming, your check is hitting the bank account on its regularly scheduled days no matter what.

Vishal Shah: On the plaintiff's side, the case really matters. If you have a dog of a case, you're not getting paid because it's a dog. And so you really have to be smart about the case selection process. That is the most important thing on the plaintiff's side.

Vishal Shah: And that's where I think you hear a lot of times, oh, this case is super weak, you're just filing it to file it. And then they try to offer some lowball amount, $5,000 or $10,000 to settle the case. And I always laugh at that approach because there's one law firm in particular where it does not matter what case I bring. I've brought four or five cases against this same firm, different offices, and every time I get the same response. This case is weak, we don't see any merit. Here's five or ten grand to go away.

Vishal Shah: And at first, I used to get frustrated. What do you mean this case is meritless? Are you serious? Look at all these allegations that are well detailed. Here's some supporting documents, here's some supporting evidence. And then I realized that it's two things. One, it's a tactic to get me to say okay, I'll take it, because other people have taken it in the past. And two, I think it is part of a playbook which underscores a bigger problem in that management lawyers are too busy. They have too much to do. And so they're not really looking under the rocks like plaintiff-side lawyers do. They're just going through the motions a lot of the time.

Vishal Shah: Now the really good management firms don't do that. But the vast majority just play through the playbook. And it's a matter of knowing what that playbook is. Thankfully, I do have a good sense of that. But also making sure your own plan as a plaintiff-side lawyer preemptively addresses those issues so you can navigate them.

Khurram Naik: Yeah. And maybe the point I had in mind is to what extent are lawyers referring you matters and maybe not comprehending the contingency component because they're so stuck in the billable-hour mindset that they can't really appreciate, hey, the case has to be strong, I don't get paid unless the case is strong.

Vishal Shah: Yeah, so I tell all of my network whenever this comes up, send me anything you have related to employment law. I don't need you to vet it. I don't need you to take a lot of time to do an investigation or have a discussion with somebody. It's an employment issue, okay, here's my buddy Vishal's information, give him a shout. And then I can take it from there in terms of evaluating whether it's a strong case or not. That's my field.

Vishal Shah: If I had to do something with recruiting legal professionals, you're the first person I would go to talk about what that looks like. And so I don't want referral partners to feel like they're obligated to only send me good cases. The only thing I ask is if it's employment, think of me and send them my way and I'll take care of the rest. Whether I can help them or get somebody else to help them, I'll do whatever I can to make sure they are taken care of in the best way that I can.

Khurram Naik: And now tell me about co-counseling. Have you co-counseled with other lawyers? And if so, how did that come about?

Vishal Shah: Yeah, absolutely. So plaintiff-side work is different from the management side in a lot of ways, like we've talked about. But one of the ways is the firm size and structure. Plaintiff-side firms on the employment side are necessarily much smaller than a lot of their defense counterparts. And so there is a ton of collegiality among the plaintiffs' bar, much more than on the management side.

Vishal Shah: On the management side, there's collegiality within the firm, but Firm A is not going to Firm B to talk about issues that they're having or what they're doing on AI, for example. In most cases, that is your competitive advantage. If you're sharing that information with a competitor, you're losing it. And you're vying for the same clients. The same is not really true on the plaintiff side. And so there's a much bigger, warmer sense of let's work together, let's go through this entire process. You need case law on this issue? Happy to provide it. You need a draft brief? Happy to provide it. Whatever it is, there are a lot of open hands willing to help you when you need that help.

Khurram Naik: I just want to pause there because that is extraordinary and rare to have. I mean, as a plaintiff-side employment lawyer, the potential number of people you can work with is in the hundreds of millions. So the odds of two lawyers literally chasing the same client are infinitesimally small. And so the structure you're describing of being able to communicate, collaborate, and learn from peers, that's got to be really special. A small universe of professionals that are all highly trained, and yet you are almost guaranteed not to be competing for the same clients. That is a really unique structure to fall into. And I think that itself is, if I was choosing different lines of work, I wouldn't have thought about that in advance. But that is a huge differentiator in choosing this line of work versus other kinds of work.

Vishal Shah: Yeah, I think one of the things I thought I was going to miss leaving the institution I left was we had this internal message board system where you can put up questions, like hey, does anybody know so-and-so as a mediator, and you get feedback from your colleagues within that one firm. I thought I was going to miss that because what am I going to do, message myself and try to get some information from me?

Vishal Shah: But the plaintiffs' bar has an organization, like I said, called NELA, where there is that same type of message board where you can say, does anybody know this mediator, let me know what thoughts you have. And people are really, really happy to share insights because one of the fundamental things that drives the plaintiff-side practice in terms of collegiality is this concept that rising tides raise all ships. If I do better in my case because somebody gave me some information, that's great. That's the precedent for them to then use what I did in my case for their next case. And it just builds and builds on top of each other, hopefully resulting in better outcomes for everybody on the plaintiff's side.

Vishal Shah: But so you were asking about co-counseling. I do co-counsel because of that collegiality. Sometimes you need help. Usually I am jumping onto other people's cases to help them. So in March, I have a trial in the Eastern District of Pennsylvania, and that is with a really, really good friend of mine whose wife and I worked together at Morgan Lewis for a while. He was also a biglaw lawyer who left and started his own firm a couple years before I did. And he and I are going to try this lawsuit together, which is going to be a ton of fun.

Vishal Shah: And then I have a co-counseling situation in April, which is when my next trial is. That's in San Antonio, federal court. And that is a situation where a guy that I know through this organization says, hey, you really like to try cases, you really know this stuff, do you want to come try this case for me? Now, it's a little crazy going back to back in trials that are far apart in the country, one is in Texas and one is in Pennsylvania. But this is the stuff that I absolutely love to do. So I'm more than happy to do it. This is a lot of fun.

Khurram Naik: You mentioned co-counseling and some of it can involve splitting fees. So how does that work? Is there a typical fee structure? Is it typically a third of recovery? Generally speaking, how do fees work?

Vishal Shah: So generally how fees work on the plaintiff side, assuming that it's not a flat fee or an hourly arrangement, it's contingency. When the case resolves, at whatever stage it resolves, a certain percentage of that amount goes to the lawyers. It depends on the jurisdiction, the types of cases, and the market. That percentage can be anywhere from 25 to 40%, maybe even more in other jurisdictions.

Vishal Shah: And then if you're layering on a co-counseling piece, there's a certain percentage of that contingency percentage that gets allocated towards lawyer one and then towards lawyer two. That allocation depends on where you are in the case, where everybody's expected to pitch in, and how much time is going to come into play. And a lot of it is just an upfront agreement. I like to have it all in writing. Hey, this is what we're doing, we're going to work together on this, and here's how we're going to split fees. Because I don't want to have any confusion later on where we're having a fight over money that we shouldn't be having.

Khurram Naik: To help me understand, I have a two-part question about how employment law has changed and the trajectory it's on, because what's top of mind for any lawyer is what's happened in my field. Am I in a field that's going to be growing and rising, or are there threats to it? Right now we have an administration change, and areas that have been very busy in the past number of years, things like antitrust or energy, there are questions about what those look like under the new administration. And aside from administration changes, there can be changes that impact the plaintiffs' bar. Can you give us a sketch of how employment law has changed in the past five years, which incredibly now encompasses the time of the pandemic? Have rights for employees become strengthened? Give us a sense of the trajectory.

Vishal Shah: That's a really good question. Employment law is similar to alcohol in that when times are good, people drink, and when times are bad, people drink. The same thing is true with employment law. There are issues that come up when the economy is booming and there are issues that come up when the economy is struggling.

Vishal Shah: For example, when COVID hit in 2020, most of the world was shutting down. M&A deals were shutting down. People didn't know what was going to happen in the near future. We were still trying to flatten the curve within those first couple of weeks in March and April of 2020. But we were incredibly busy as employment lawyers. We were monitoring every single court closure, every single stay-in-place mandate. All of these new things that were coming out hour by hour, we were super busy. Companies were laying off employees. So we got busy helping with that.

Vishal Shah: When the economy is bad, companies lay off folks. There's certain legal attention that's needed for plaintiffs at that time. And then when you're hiring folks, it's the same sort of deal. You're reviewing employment agreements and compensation packages and structuring things in a way that makes sense for your client.

Vishal Shah: So generally speaking, we're really, really busy and have enough to do on our plates, knock on wood. What we're focusing on changes over time. In the 2019 to 2020 period, there was a change and shift in the culture of the American people where it felt like there was a bigger anger towards big business. There was a bigger skepticism towards what companies were telling us, what the news was telling us, and how people were navigating those issues. And there was also a rise in being more sensitive and more mindful of people around you and how you approach conversations with certain people.

Vishal Shah: And I think the law tracks some of those changes. There were implementations of local laws at the state level that covered hairstyles, covered weight, covered all sorts of issues that weren't traditionally thought of as protected characteristics like race or gender or disability or age. And so there were evolutions in the law that came about in that way. Most recently, you've seen a lot with the NLRB striking down certain provisions and certain types of agreements like non-competes and stay-or-pay type agreements. It shifts and it changes. Staying on top of those trends is really, really important. And the EEOC does a great job of that. There are a ton of people on LinkedIn that post about great developments in the law. And just reading the news and looking at publications like Law360 to make sure that you're seeing where the trends are.

Khurram Naik: But what do you think is the biggest existential risk to the plaintiff side? It sounds like everything is really strong and it doesn't seem like there's going to be any rolling back of protection for employees. It's been a ratchet upward of more and more rights granted and the expansion of protected characteristics.

Vishal Shah: I think one of the biggest threats to the plaintiff-side employment practice is this concept of damages caps. For example, under Title VII, which is the primary discrimination law at the federal level prohibiting all sorts of discrimination, there are caps on how much money you can receive from a lawsuit. No matter what a judge says, no matter what a jury says, if you have this type of claim and the employer is of a certain size, it's capped at a certain amount. And the highest level for the biggest employer is $300,000. That figure has not changed since the 1970s. It hasn't adjusted for inflation. It hasn't accounted for the value of money and how people are experiencing these situations.

Vishal Shah: You will see these massive awards against companies who have done really bad things and a jury has found that they've done really bad things and awarded multiple millions of dollars to plaintiffs who have suffered. Remember, these are the folks who have seen the documents, listened to the witnesses, sat through a trial, and come to this decision while the company is telling them to do the exact opposite. So it's a considered approach. They value the case. They sign off on the damages number. And then a judge comes in after the fact because they're required to and has to lower the amount.

Vishal Shah: And I think $300,000 sounds like a lot of money. But when you factor in the cost of an attorney, when you factor in what happened to you, $300,000 just doesn't go the same length that it used to back in the 70s. And I think that's one of the biggest fears and biggest threats to the plaintiff-side practice. In Massachusetts, we're fortunate to have a state law that doesn't cap damages in that context. Some states don't have it. So my friends in Texas and my friends in Alabama, when they have a big verdict in a case that deserves a big verdict, it gets punched down because of these caps that haven't been adjusted for 50 years.

Khurram Naik: So let's switch gears here. Tell me about how you are thinking about counseling other people, because I'm sure you get people who reach out to you all the time from biglaw, curious about the path that you've struck. It is unusual to walk away from a big firm to launch and to jump to the other side of the v. So big picture, how should someone think about this? If someone is a first-year associate at a big firm and they're thinking about whether they prefer the biglaw platform, because there are plenty of great things about big firms, and you have the credibility you have now in part because you've been at a big firm, not to mention some financial capital you've set aside over the years. So there are a lot of things in favor of spending time in biglaw. But of course, there are plenty of opportunities outside of it. You and I are both operating outside of it and thriving. How do you counsel someone on the path through biglaw and success there, versus saying, hey, if you want to go plaintiff side or launch your own firm, here's the path?

Vishal Shah: So I think there is a ton of hate on biglaw generally. And maybe that's just the LinkedIn people that I see and follow or maybe it's on Reddit or whatever the case might be. But there's a lot of hate and I think some of it's deserved. I think a lot of it is not. I think biglaw is a great place to cut your teeth and to learn how to do things the right way and to learn how to do things in a way that moves the needle. Both from a business perspective for corporate clients but also from a litigation perspective.

Vishal Shah: Because the fundamental difference is, and we were talking about Apple so I'll use them as an example, Apple doesn't care about Ms. Jones' discrimination lawsuit. Apple cares about the portfolio of discrimination lawsuits that it has within certain geographical jurisdictions. Most companies tend to think of cases as a portfolio of risk, as opposed to, this is Ms. Jones, something terrible happened to her at work and now she's trying to seek some recovery for that, some justice for that. The way you view it is fundamentally different from the management side to the plaintiff side.

Vishal Shah: I think going back to biglaw in particular, if you're at the right firm, they should be investing in you, they should be pouring into your development, both as a business person and as a litigator or transactional lawyer or whatever your specialty is. So yes, you should be learning the nuts and bolts of an M&A transaction and the things that you need to be looking for and things that you need to be wary of. All of those things on how you do your job day to day, you should be number one learning that on the job and number two getting specific training towards that.

Vishal Shah: The second piece is the business side. What are the measures? The law is one piece of it, the business is another. How is the business functioning? How are we structuring this case on a financial model? Why do we do it this way? How do we make it the most profitable? What is utilization? And how do we use that? What is leverage? All of these terms are things floating around in biglaw business departments, but they're not being explained to the individual associates because they say, we don't want you to worry about that. Do the best job you can do on the task in front of you, and that's that.

Vishal Shah: But I think that's short-sighted because when that person makes partner or is getting close to that senior role, they have no idea what any of this means. And you're learning it then, as opposed to learning it on the front end. I think there are a lot of great training opportunities that you can get in biglaw. Less hands-on in most cases, but still training.

Vishal Shah: When you come over to having your own firm, it's deciding what you want to invest in. In my case, the day-to-day nuts and bolts of litigation, I don't need that type of training because I've done it for so long. What I do need more training on is how to take my trial practice to the next level. What are effective ways that some of the really, really successful trial lawyers are implementing? And how can I take that and put it into my practice? Thinking of it in a more nuanced approach helps in terms of how you're developing.

Khurram Naik: Yeah, I think those are great observations. I remember I had a client call with a partner and after the call I said, hey, what comes next for you today? I already worked on some non-billable stuff, some business development. And I said, if you enjoy that. He said, not really. I didn't really have any experience with that. Then I said, well, I guess I should start learning that now. And he said, nope, you should just focus on doing good work. So that less-than-learned approach, right? Those are great things to be thinking about ahead.

Khurram Naik: And we're at time. This conversation flew by. I think there are so many questions I had to learn more about your business because it's fascinating to me, and to dive more into your trial preparation approach. But yeah, best wishes on those coming trials. I think you're going to crush it. And thanks for sharing your story about how you got here. I hope we can revisit this a year or two from now and talk about all the other successes you've had.

Vishal Shah: Man, from your lips to God's ears. I really, really appreciate the time. I've learned a ton in just talking about this whole process with you. So I probably gained from it as much as you gained from it or the listeners gained from it. So thanks for having me and really happy that we did this.

There are plenty of places you can learn about advocacy as an appellate lawyer, and we certainly cover some of that here. But this is a rare opportunity to explore three underdiscussed topics: the market for appellate litigation, the business of appellate litigation, and the seismic shift in appellate practice over the past couple of decades. We also dig into how to make decisions about the kind of practice to join and build, and the role that mentors and relationships played at every turn in Pratik's career.

Keep reading below for the full link to the episode and the full transcript of our conversation.

Top Insights

Below are the highlights of our conversation:

• Mentors Open Doors You Cannot See: Pratik's career was shaped by a chain of mentors starting with a chance encounter at a law school luncheon. Judge Chabria connected him to Judge Breyer, who connected him to a Supreme Court clerkship, which connected him to the Solicitor General's office. None of these steps were visible from the outside, and none would have happened without someone taking an interest in a first generation law student.
• The Market for Appellate Law Has Transformed: Thirty years ago, specialized appellate practices in the private sector barely existed. Today, the Supreme Court bar has expanded into federal courts of appeals and regulatory litigation, driven by increased specialization, sophisticated clients, and a judiciary more skeptical of agency action. The number of Supreme Court arguments has shrunk, but the overall demand for appellate advocates has grown.
• Choose the Goldilocks Model: Pratik describes three models for appellate practice at a firm: the mega practice led by a former Solicitor General, the solo transplant building from scratch, and what he calls the Goldilocks model, a small but established group with room to grow and shape its direction. He chose the third, and it allowed him to build culture, develop associates, and make four homegrown partners in a decade.
• Build a Narrative the Court Wants to Follow: At the Supreme Court level, the court can do almost anything it wants. Your job as an advocate is to craft a narrative that makes the justices want to rule for you, using whatever tools are strongest, whether that is precedent, text, policy, or equities. Distill to one, two, or at most three issues, and lead with your strongest argument.
• Pro Bono Is Not a Side Project: At Akin, some of the heaviest matter hours in any given year come from pro bono Supreme Court cases. Pratik views this work not as something done in addition to the job but as an integral part of what makes appellate practice rewarding and valuable to the firm.

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Full Transcript

Khurram Naik: This is Khurram with Khurram's Quorum. My guest today is Pratik Shah. Pratik is the head of the Supreme Court and appellate practice at Akin. Pratik has about as padded a resume as you can get, but I'm struck from our conversation here about the perhaps unlikely path he took to get here as a first generation lawyer. And there's plenty of places you can learn about advocacy as an appellate lawyer. We certainly cover some in that space, but this is a rare opportunity to explore the market and the business of appellate litigation. Here's Pratik.

Khurram Naik: So, I'm excited to have you here, Pratik. Your lens on practice is fascinating and you have a pretty unique story for someone who came from maybe an unlikely place to end up where you are now. And so it will be interesting to get into that part of your roots and Akin later on. But I want to begin with, you have a really unusual story that I think you've told in some smaller venues and I'll be excited to share it here about some surprising impact of some early conversation you had in law school and how that led you down a path that had a big impact in your career later.

Pratik Shah: Yeah, I would start in my first year of law school. I was at Berkeley and like many first year law students trying to figure out what I was going to do for that summer afterwards and I stumbled into one of those summer luncheon sessions. And this one was about judicial externships. And there was a panel of clerks who were currently clerks in California courts and I needed to establish California residency at Berkeley. So I knew I would stay there. And one of the panelists was someone named Vince Chabria, now known as Judge Chabria on the Northern District of California. And he was then clerking for Judge Breyer on the Northern District of California and talked about the opportunities to be an extern for the summer. And I ended up submitting my resume and Judge Chabria was kind enough to share it with Judge Breyer and I was able to have that opportunity for that summer.

Pratik Shah: And that summer, maybe more than any other experience or job I've had in the law, may have had the biggest impact on me. For a variety of reasons. One is because Judge Chabria and Judge Corley, who was Jackie Corley, was also the other clerk for Judge Breyer that year. So all three of them are now somewhat fortuitously on the Northern District bench as judges. But they went out of their way to be great mentors and help a first year law student along, and Judge Breyer was a fantastic boss. I mean, most people wouldn't be taking interest in unpaid first year law students who are externing. But I recall vividly that one day I came into chambers. I had been assigned to do some sort of memo in a bankruptcy case on a due process issue, which sometimes arises in bankruptcy cases. And I think I was somewhat nervous about it because I hadn't taken constitutional law yet. Typically that's taught in the second year. And so I'd written this memo and submitted it to the judge and the judge said, why don't you come up to chambers to discuss the memo. And I came up to chambers, his office, and he said, well, Pratik, I haven't yet had a chance to read this memo closely yet. But my brother has and he has some questions. And then he kind of gestures off to the side and I turn my head. And much to my shock, I see Justice Breyer sitting on the sofa there with a copy of my memo in his hand.

Pratik Shah: And that may have been the last clear memory I have of that morning. I may have blacked out, I don't know. But we had a roundtable discussion. I remember the justice sitting there, the judge sitting there, Judge Chabria and Judge Corley kind of smirking there. And it was obviously a very memorable experience for me. And I share that story, I guess, for a couple of reasons. One, obviously it had a profound impact on me to have that opportunity as a student and believe that, okay, look, I can be in these circles and think bigger about future opportunities. But also I think it said a lot about the people in that room, Judge Corley, Judge Chabria, Judge Breyer, and Justice Breyer, all of whom made that possible. They did not have to do that at all, to give that opportunity to a first year law student who hadn't taken constitutional law. What benefit are they getting out of talking to me about it? But I think it speaks to their willingness to be mentors, to be educators. And obviously it had a big formative experience in my life. I have no reason to think the justice ever remembered that encounter. Obviously I went on to clerk for him a few years later. But maybe I got the confidence to apply, and obviously I'm sure some help behind the scenes from Judge Chabria and Judge Breyer along the way.

Khurram Naik: What was the impact after that? Did that, like after you got out with the initial shock, I could easily see something like the ego meter might go through the roof. We all met people like that in law school after just like their first semester that did well and, oh wow, now they're just like swaggering down the halls. Did that happen to you? If not, why didn't it?

Pratik Shah: Yeah, I guess you'd have to ask the people around me to see if that was true. Hopefully that didn't happen to me. No, I think I just remember being mostly thankful for having that opportunity. And I think something that has been a big part of my career has been the role of mentors. And it wasn't just that experience in isolation. It was Judge Chabria taking an interest and saying, hey, look, I know your background. I know how you did. Here are some judges you need to apply to for clerkships. Most law students don't have a great idea of how the clerkship process works. But especially law students coming from families without any lawyers, probably like a lot of South Asians, at least of my generation, that made a big difference. And that gave me the confidence, hopefully not overconfidence, but at least the confidence to apply to clerkships. I went to clerk with Judge Fletcher on the Ninth Circuit after that, which was just a wonderful experience because he is just one of the best human beings on the planet, forget judges. And then later on to Justice Breyer. So I think it had an impact in that way.

Khurram Naik: Let's start with Judge Fletcher. What's one or two practice points, maybe something very practical or bigger picture with career and how to think about it, maybe either direct or indirect? Because I can think, I externed for two federal judges in law school. And there's things that they directed to the other externs that was helpful. But it's also things that they just incidentally said to us as well that they didn't even necessarily know the impact it had on us. So I'm just opening the spectrum of kinds of things you could have learned. What's one or two things that you take away from that experience?

Pratik Shah: Yeah. So I'll give you one very concrete lawyering tip that I still remember from the very first project that I had there that has stayed with me and that I share with other young lawyers. And then one kind of bigger picture thing that I think is more impactful. But the very concrete lawyering tip, since you ask for concrete things, is it was a statutory case, I remember. And those of us, I think I'm old, but I'm not so old such that we didn't have Westlaw and stuff when I was in law school. So a lot of us kind of do legal research, especially as young lawyers, using Westlaw or whatever and even looking up statutes online. And you read the provision and you go about it. And in that case, I remember you read the provision and you think it means one thing. And I remember Judge Fletcher telling me, yeah, this analysis makes a lot of sense and all of that. But here, if you pull the book. And he comes in with the book and he flips through the surrounding provisions, and it kind of puts it in a context that maybe, look, there's another way to read this. And so when I have statutory cases, I actually try to get the volume of the statute. And I look at books probably more than most of the younger lawyers. But I think in that specific context, there was actually value to having surrounding context that you can't just get through quick online research, but it's much easier to flip through a book and do that. So there was that sort of concrete tip that I still use in practice now.

Pratik Shah: But more broadly with Judge Fletcher, I mean, he just shows you, no matter how brilliant someone is or how accomplished, he's an Article III appellate judge on the Ninth Circuit and all of that. There just isn't a more down to earth person that you'll meet. And so you ask that question about ego. When you have models like that early on, you see someone who's so prominent and accomplished. But yet you would never know it if you saw him on the street. The one rule in chambers we had was you can't dress better than the judge. And that was a hard bar to meet, to be honest with Judge Fletcher. He just did not have any airs. He would eat lunch with us every day and talked with us, just as you would talk to anyone else or maybe how we would talk to his kids. So that has certainly stuck with me.

Khurram Naik: And so you had this early connection with Justice Breyer. And so of course, it was obviously you could apply to the Supreme Court to clerk with him. What heading into it though, what did you think you were going to get out of a Supreme Court clerkship? I mean, it's obvious, of course, it's just what an incredible credential to get, experience to have. What a unique experience. And so there's obvious things about that, but specific to you, why, what made you say I want to do that? And what's the payoff going to be for you?

Pratik Shah: Yeah. So at the time I was thinking maybe academia. I really liked law school and they tell people, look, if you really like law school, maybe you'd really like being a law professor. And the other thing I was thinking is, maybe becoming an appellate advocate having clerked on the Ninth Circuit. That was the area of law I was exposed to, and I really enjoyed it. And so for those paths in particular, a Supreme Court clerkship becomes very helpful just because that is a credential that, whether it's in academia that law schools value, or if you're going into appellate practice, is valued. And so for me, it made a lot of sense based on those being a couple of the paths that I was thinking about beyond the fact, obviously, it's just an incredible experience.

Pratik Shah: Even if you wanted to do nothing related to that, even if you didn't even want to practice law, the Supreme Court clerkship is just a special year. You're two years removed from being a law student. And then you're kind of sharing chambers and talking about legal issues with the best legal minds in the country and the justices who are just legal giants. And because of the weird way in which the Supreme Court works, I mean, it's a pretty isolated existence for the justices, even probably more so back then than today, where their interaction is really with their four clerks and maybe some informal interaction with the other justices, but not a whole lot, and formulating their views. And so you have this unusual interaction where you have people who are really going to be making important decisions for the country and then discussing them with folks who are two years out of law school. So to have that vantage point and be able to start grappling with some of the biggest legal issues of the day at that point in the career is just an experience that you can't really replicate. And so that, I think, is a reason for anyone to want to do it regardless.

Khurram Naik: What do you think is the single most misunderstood aspect of the Supreme Court?

Pratik Shah: Yeah, that's a good question. What I'll say is that, and this is something that I think different people may have different views, I don't think it's as true today. It was a different court when I clerked on it. That was the 2003 term. So you can see how old I am, over 20 years ago. And I guess what I'll say about that court is, it was a court of relationships. Obviously you still had a lot of five-four decisions. At that time, it was Justice O'Connor who was the swing vote. But think about that time. Justice Scalia and Justice Ginsburg, polar opposites, but their relationship is well chronicled. And for those who clerked at the court, that's not just made up. It is a true relationship.

Pratik Shah: The fact that Justice Breyer would go and talk to Justice Kennedy. Not always would he be able to influence him, but sometimes he would. They would have a real dialogue. Even Justice Breyer and Justice Scalia, you're talking about folks who had opposite schools of constitutional interpretation. And yet they went on a road show for the country to see, hey, look, here is how we have two different views, but here's the common ground, here's how we're different. And you could just tell that the relationships mattered. Justice Thomas said publicly that he looks back fondly on that court because he felt they really trusted each other.

Pratik Shah: And in some ways, I had the privilege of clerking for Justice Breyer, who I think in a lot of ways embodied that court. He's not someone who's interested in debater points. He's not interested in zingers. He puts a premium on relationships. He often talked about how nine people with different views managed to be so collegial. They would have these weekly conferences where they decided cases and sometimes they didn't go your way. But no matter how it came out, he would come back and he would continue to be optimistic that the process is working. We had the dialogue and maybe we didn't get this one, but the next time around, maybe we'll be able to persuade a majority. And it speaks to his personal fundamental decency, fair mindedness, and optimistic outlook. I think qualities that I've tried to bring into the practice that I do, but quite frankly, it's qualities that I think all of us could mirror more today. And I think a lot of the divisiveness you see in court opinions today, in writings about the court, is a big change from back when I clerked.

Khurram Naik: What is it that most surprised you about Justice Breyer?

Pratik Shah: Yeah. I mean, I don't think there's anyone I can think of that truly, genuinely believes to his core in our system of government. And that really embodies kind of his entire jurisprudence, his being. And I'm not just talking about the judicial process, that the judges are just trying to come to the right answer. And people have different perspectives, and it's not all result oriented. I'm not just talking about that. He certainly believes that, but more broadly, he believes in our system of government. That everything should be designed to kind of strengthen the democratic processes so that people can participate in government, get their views heard. He talks a lot about law bubbling up. And it's really something to the core.

Pratik Shah: And I think in today's world, even back then, but certainly now today where everyone is jaded and everyone believes that government's dysfunctional, that little good comes out of it, that judges are just politicians in robes, all of that. That is something to his fiber that he doesn't believe. And he's not someone who hasn't been exposed to everything. He was on the Senate Judiciary Committee as chief counsel with Senator Kennedy. So he's been in the legislative branch. He's been at the highest levels of the judiciary and still he believes that today. And so that's, I guess, something surprising, but also admirable.

Khurram Naik: And what have you found, what's a perspective that you have that differs from him, a disagreement you have? Where does your worldview depart from his?

Pratik Shah: Yeah, it's a good question. I think it's hard for all of us to have that same level of optimism and faith in the system when we're confronted with today's world. And so I guess, to me, it's become more complicated in trying to have that same faith. But I try to keep some of that same optimism.

Khurram Naik: Okay. And then tell me about your path from the Supreme Court to the Solicitor General's office.

Pratik Shah: Yeah. So I taught constitutional law for a year. I was thinking about that. I then ended up at WilmerHale in Boston for a couple years. And after maybe two years there is when I applied for an opening at the Solicitor General's office. And if I had to pick, right now we've touched on perhaps the two most formative experiences early on, the third one has to be my tenure at the SG's office. I think for any young appellate lawyer, it's hard to imagine a better job to learn how to be an appellate lawyer. Much like in the Supreme Court clerkship, I was talking about being two years removed from law school and you're there. Well, in the Solicitor General's office, you might be two years removed from a Supreme Court clerkship, and you show up at the Solicitor General's office. I had only argued one other case in any court, and that was an intermediate court of appeals, a state court of appeals in Maryland. And then you come to the SG's office and your next argument is going to be in front of the Supreme Court.

Pratik Shah: But you're not thrown in there completely blind, because you get the privilege and the opportunity to learn from really the best, in my opinion, the best Supreme Court advocates in the country. The deputies, the Solicitor General, are obviously always very esteemed appellate practitioners. I was the last hire of Paul Clement, which I think speaks to the truly bipartisan nature and institution of the SG's office. But there are career deputies. When I was there, Ed Kneedler is still there. Michael Dreeben was there, the criminal deputy. Both of them have well over 100 Supreme Court arguments each. And when you watch them at work, I mean, just their substantive knowledge, the way they go about it, you're really not going to get a better education in how to be a Supreme Court advocate. And so for me, that was a transformational time, from being an aspiring appellate lawyer to actually becoming one and doing it.

Khurram Naik: And we've talked before. I know there's actually, somebody might see your resume and see this kind of march of progress and miss out on some of the behind the scenes action that happens to get there. So I actually think, let's double back to that one externship, because I think that's where the story starts of how you started making connections and then how you started learning that skill set of networking, which was, I think, new to you. And so many people, but particularly as somebody without, as a first generation law student, tell me about how that journey started and I want to pick that up as you progressed in your career.

Pratik Shah: Yeah. Now, I am not a natural networker. I think those who know me well would know that. I don't think it's something I've ever really shared with a group of people, but I'll say it now. It was so kind of foreign to me that I remember at the beginning of law school, you have those receptions or career workshops when firms or other people came, I would actually, because I just wasn't comfortable approaching people and talking, I would literally write down beforehand to myself on a little scrap of paper, kind of like three bullet points of things that I thought people might find interesting or things to talk about in that context, just to make me more comfortable and not be on the spot.

Pratik Shah: And so I think I've gotten past that at least, but there are little things along the way. Like you said, go back to that first year. Judge Chabria, I do feel like I owe him a lot because he did take that interest in me, and not only with facilitating that interaction with Judge Breyer and Justice Breyer, but helping me with the clerkships when I clerked for Judge Fletcher and then later for Justice Breyer. And then it didn't end there. Along the way, I mentioned the SG's office. Someone had put me in touch with now Chief Judge Sri Srinivasan, who was just an assistant in the Solicitor General's office at the time when the opening had come open, and he was leaving the SG's office. And someone set up a phone call and I had a phone call with him about the job and then I applied for that opening and got the job there.

Pratik Shah: And then when I joined the office, there was another assistant still there who was a few years ahead of me, Kannon Shanmugam, who's one of the country's best Supreme Court advocates. And so I got to know him there. And lo and behold, as he leaves, in comes Neal Katyal as the principal deputy. And I got to form a strong relationship with Neal. And then when Neal leaves, who comes back, Chief Judge Sri Srinivasan becomes the principal deputy. Neal was the principal deputy under Justice Kagan, who was then Solicitor General, and then Sri became the principal deputy under Don Verrilli. And so I got to come full circle from that very initial conversation I had with him to actually working with him and forming these relationships.

Pratik Shah: And those folks happen to be brown, happen to be Indian, which, I think honestly it made me more comfortable to form those relationships. It doesn't obviously mean your mentors have to be of someone of your same ethnicity by any means. But for me, at least someone who might not naturally form those relationships, it made it easier to have that common ground. So I think there is something to the fact of having folks like that. I think it does make a difference and forms a path. I've tried to do the same for those coming after me.

Pratik Shah: I think it's an interesting niche of the bar. Obviously South Asians are growing in the law, but the Supreme Court bar is one where we've been long established now as a strong community. All the people that I mentioned, Chief Judge Sri Srinivasan before he became a judge, Neal Katyal, Kannon Shanmugam, myself, Deepak Gupta, and before all of them, and now many after me. Easha Anand, who argued like three cases last term, Jagannadha Sai, Vivek Suri, so many folks. And so here you have this little corner. And I don't think it's coincidental, a little corner of practice where through the SG's office, there's been a chain and a network of folks who've been able to support each other at least in some way or another.

Khurram Naik: Then building on that, can you speak to how the process of professional growth and mentorship at the SG's office compares? I mean, of course, when you're a Supreme Court clerk, that's a term. It's terminal in that way. But can you compare the experiences of training, mentorship, and so on, for the SG's office as a training ground versus the Supreme Court?

Pratik Shah: Yeah. So clerkships, I think, are great grounds because you don't have to have any stint working or any ability to do anything. It is natural mentorship. I think many judges view that as a critical part of their role. And so that's why I highly recommend clerkships, even if you have no interest in the public law, even if you have no interest in litigation. Do a clerkship because that is the easiest way to form this relationship with someone who knows a lot more than you, has been accomplished, and will really become a backer for you for years and years to come in your career. And that just happens organically through the process. And so that's a really nice natural thing about clerkships, whether that's a district court clerkship, a court of appeals clerkship, or a Supreme Court clerkship. I don't think that that is a differentiator. I think that is something that happens with all of them.

Pratik Shah: In the SG's office, it's obviously not structured in that way. This is your job. You're a fully formed lawyer, you're going out and practicing. But it's a small office. And I think that makes it very comfortable to form these relationships and learn. I mean, the office, I think for those who aren't familiar, is shockingly small. Sixteen assistants, four deputies, and the SG. You're talking about 20 attorneys. That's it. That do Supreme Court litigation for the entire United States executive branch and oversee all of the appellate litigation in the courts of appeals for the federal government. And so when you're in that small environment, I just think it's easier to thrive, to learn from others, to form relationships, have conversations after an argument. Hey, you were awesome. Here's one thing you could have maybe, here's one way to handle that question differently, or you could have done this. Those are conversations that happen in the SG's office after every argument. Everyone's very supportive, but at the same time, you're kind of learning from each other as well.

Khurram Naik: Are there any advantages you can think of to training in appellate advocacy at a firm as opposed to government, for instance, the SG's office?

Pratik Shah: Yeah. Look, they both have great value, and at different points in your career, one might make more sense than the other. I mean, the advantage of the firm for very young lawyers coming out, and this is what I did. Early on at WilmerHale, I had the opportunity to work on the Boumediene case in front of the Supreme Court and be one of the primary drafters of that brief along with one of my co-clerks at the Supreme Court, Julian Mortensen. We got to do that with Seth Waxman. So you get these great opportunities to learn from great folks and be involved early on.

Pratik Shah: I think the differences in the government when you go out, you can get oral argument opportunities. They're more plentiful and you don't have to worry about paying clients authorizing a very junior person to do significant oral arguments. The government, that's just how it's done. And so there's opportunities there. That's something, quite frankly, in our practice, as I've come over to the private sector, that I've realized. We put a big premium on trying to get oral argument opportunities for our associates, because I've always found that to be the one lagging part of big firm appellate practice. And I've tried to take the lessons from government and realize, look, if you want to be an appellate lawyer, it's important to get oral argument opportunities. And so that's something we try to put a big premium on, getting at least one oral argument for each of our associates every year. And then naturally it happens, and they build more over time on their own, but it takes some work to do that in the early years. So that's, I think, one of the differences between government and private practice.

Khurram Naik: Yeah. And going back to the SG's office, in one of our earlier conversations, I asked you, hey, what was an inflection point in your career, and you talked about the Defense of Marriage Act and its course at the Solicitor General's office. So can you talk a little about that?

Pratik Shah: Yeah. So the Defense of Marriage Act arose while I was an assistant in the SG's office. And up until that point, in the Bush administration, and quite frankly in the Clinton administration, the federal government had always defended the constitutionality of the Defense of Marriage Act. And just to remind everyone, the Defense of Marriage Act was the federal law that said the federal government would not recognize any same-sex marriage, even if it was lawful under state law. So for purposes of social security benefits or any million other federal benefits, there was a federal law that said the federal government would not recognize same-sex marriages. Like I said, it was defended during the Clinton administration, defended during the Bush administration. And then when President Obama came into office, he and Attorney General Holder made the decision that they would no longer defend the law because they believed it was unconstitutional.

Pratik Shah: And so the Justice Department put a new team, including in the Solicitor General's office, to reflect that change in position. And I was part of that Solicitor General's office team along with Chief Judge Sri Srinivasan, who was then the principal deputy. And so we worked on that case together for the federal government, in briefing. I wrote the brief challenging the constitutionality of the Defense of Marriage Act in the Windsor case, which went on, with Robbie Kaplan arguing for Edith Windsor, and Don Verrilli arguing for the United States. The Supreme Court struck down, as everyone now knows, the Defense of Marriage Act as unconstitutional, and then that formed the basis for the decision a few years later in Obergefell that recognized marriage equality as a constitutional right.

Pratik Shah: So that was a formative experience for me for a lot of reasons. Some of the obvious, it was a landmark case. But also, it was the first time I was part of a case where there were so many interested people, not just in the public at large, but even within the government. People had been defending this law for a long time. It wasn't an easy decision. It's not something the government often does, to attack its own federal law. So there was that, dealing with that constituency. There were a lot of people who felt strongly on the other hand. The meetings on the law were filled with people from different agencies. Watching how Don Verrilli navigated all those dynamics was a true learning experience. Working closely with Chief Judge Sri Srinivasan and developing our arguments along the way. Working with Robbie Kaplan, the great Robbie Kaplan, along the way.

Pratik Shah: And then personally, obviously, at least of that generation in the South Asian community, it's not something that was easily discussed, but I've had since I was very young an uncle who is gay and has lived with his same-sex partner ever since I was a little boy. And my grandparents came to accept that. I'm sure I was too little to know the struggles to get there. But we remain very close and I know it was incredibly meaningful for him and our family when they got married shortly after those decisions in the state of Washington. And so professionally, personally, all of those things, a meaningful case for me.

Khurram Naik: And then, I think part of what we talked about before was, the significance of that case for you was really coming into your own as an advocate and as a professional. To kind of understand your potential and understand what it felt like to be steering your career to be a leader. Can you talk a little more about that legacy for you?

Pratik Shah: Yeah. I wasn't steering the ship in that case by any means. That was Don, that was Sri. I was the one writing the briefs and developing arguments. But that did lead, you're right. It was born in the sense that that was towards the end of my tenure in the SG's office. And that's honestly what led me to start thinking about what's next. I'd been there over five years at that point. And it felt like, gosh, it's going to be hard to top this experience working on that case. I loved the job. I loved briefing and arguing Supreme Court cases. I've already talked about what a great institution the SG's office is. But the one piece that's missing from that is you aren't the one steering the ship. You're not the one ultimately making what's going to be the government's position in the case. And what are going to be the major strategy calls? That's ultimately not your call as an assistant. That's the SG's call.

Pratik Shah: And so as I was thinking about it at that point in my career, it was, hey, look, am I ready to try to take that next step and kind of be the one who's making those strategy decisions, making the ultimate calls, taking more of a leadership position in my cases and in the practice? And that's one thing that you're limited in your ability to do in the SG's office as an assistant, as great a place as it is. And so I think that's what probably got me thinking, what's the next step?

Khurram Naik: And so the next step for you was a return to private practice. Tell me how you assessed the landscape and how you made a decision about what the properties were that you were looking for, and what were the right conditions for you for success.

Pratik Shah: Yeah. So when I left, which is now over a decade ago, when I left the SG's office, as I kind of viewed the landscape of appellate practices in DC, it struck me that there were kind of three different models or types of practices. One was kind of the large mega practice where I had been an associate, for example a WilmerHale with Seth Waxman, or a Carter Phillips at Sidley, or the late Ted Olson at Gibson Dunn, right? Big built-out practices with a former Solicitor General, a very prominent person with maybe a half dozen partner deputies or more and then senior associates, mid-level associates, junior associates, built out. So that was one model. Probably not the right model for me because I was looking to go somewhere where I could be in the leadership capacity, driving the bus, and you're not going to do that when there's Seth Waxman, Carter Phillips, Ted Olson already at those practices.

Pratik Shah: The opposite end, the second model, is the kind of free agent model, or really a firm that's interested, doesn't have an appellate practice, but wants to bring on an experienced Supreme Court litigator to either have one or to build one. And if you think about some of the New York firms that didn't historically have those, there have been a number of people who've gone on and done that very successfully. Kannon Shanmugam did it. Williams and Connolly originally. Jeff Wall now at Sullivan and Cromwell. Doug Hallward-Driemeier at Ropes. We were assistants together. And they've all been incredibly successful. And the upside there is you build it in your vision. But there is, I'm not going to talk about the stories that did not work out, because that's a big risk at those places that haven't had it. And also, you don't have that group. You might be able to do the practice, you're the person, but you're working within a general litigation group, and you don't have that same tightly knit, well-defined group that you might have in a clerkship or in the SG's office or in one of those bigger firms that I had mentioned before.

Pratik Shah: So I think there's pros and cons to each of these, but that's how I saw it. And then there is what I view as the third, what for me was the Goldilocks model, which is, look, a well-defined appellate group, but it's small. It's not led by a former SG, it's small, it's strong, but there's room to build, there's room to grow, but it's got a foundation and it's got established appellate credentials. And I think a number of folks I would put in that category. Akin obviously is where I am now. I would put in there Jenner, Morrison and Foerster, all places like that with super high quality appellate practices and people that I think fall in between those two other extremes that I mentioned.

Pratik Shah: And for me, that seemed really appealing. You have a real group of appellate lawyers that you can be part of, a small community within these big mega firms, and yet it's not so big such that you need a hierarchy that you might at some of the bigger firms. You can really work with everyone. It can be very collegial, very horizontal rather than vertical, and you can shape its direction, you can grow it.

Pratik Shah: And so at the time I was coming out, President Obama had just nominated, now Judge Millett, Patty Millett, to the DC Circuit. And so Akin was looking. She was head of Akin's Supreme Court and appellate practice at the time. And I believe she had reached out to Judge Sri Srinivasan, who was then the principal deputy Solicitor General. And he put us in touch. I did not know Judge Millett at the time, but he put us in touch and I ended up hitting it off with Judge Millett in terms of kind of how we viewed things. We had both come from the Solicitor General's office. She had spent even a longer time there before my time. I think we had just a very similar vision. She had hired a group of folks who were very down to earth, super smart, talented, Supreme Court clerks and all the like, but also folks who are very down to earth, which is how she is for anyone who knows her. And I just hit it off and felt very comfortable, felt like I could trust her. And that's where I ended up going, to try to build and take the reins from her and build on all the wonderful things she had done and not screw it up and hopefully build and grow it over the years.

Khurram Naik: So, you mentioned a few other peer firms that you are kind of in that same bucket, that Goldilocks spot. You mentioned Morrison and Foerster, Jenner, and I'm assuming there's maybe a few others. How would you differentiate Akin's practice from those peers?

Pratik Shah: Yeah, look, they're all great practices and great folks at them, close friends and others from the SG's office, all folks who I admire. And that's one of the cool things about the appellate community. A lot of us have filtered through the SG's office at one time or another, we do moot courts for each other as favors and all of that. So there's a lot of synergies.

Pratik Shah: What I could say about Akin is, I think we've really tried to build a culture of really putting a premium on people who like working together. There's no doubt about it that we're a big law firm and everyone works very hard and all of that stuff. And so if you're going to be somewhere working hard, let's do it with people you really want to be around. So it's a non-negotiable. We're going to hire the most talented folks, and we've been very lucky because we are relatively small. We hire maybe one person a year, so we're able to get the pick of the very best talent in the country. But that's not enough. Is it someone who is going to fit in with our culture and be someone you really want to interact with? There's very little management I have to do, to be honest, of our group because the people just work together so well.

Pratik Shah: And so that's, I think, been a defining feature. I guess the other thing I'll point out is the fact that we all argue cases, from top to bottom. We had our associate, Margo Rascon, who just argued her first-ever case, not just a pro bono case, but for a paid client in kind of a bet-the-company type matter in the Fifth Circuit and won. And because we are relatively small, our matters tend to be more leanly staffed. And so the clients get to know not just me or one of the other appellate partners, but get to know the associates on the case too, because there might be only two or three of us on the case. And so that gives them the confidence, because it's often hard to talk a paying client with a big thing into saying, hey, I'm going to trust someone to do their first argument in it. But if they've seen that person at work and interacted with them and really learned that they're the brains behind the operation, then I think that happens.

Pratik Shah: And so we try to do that, whether it's through a pro bono opportunity for the first few arguments or like for Margo, a paid opportunity. One of our other great talented, wonderful counsels who came to us from Justice Sotomayor is going to be arguing in the Second Circuit next week for a major case for Kodak, a big case for Kodak. And so these are the sort of arguments that our associates are doing.

Pratik Shah: And so, yeah, it's been a real privilege for me. The one last differentiating factor I'll mention is, in my time here, we have not hired a single lateral partner in my decade at Akin. All homegrown. We've made four homegrown partners. I was the only one after Patty left here in DC. We've made four homegrown partners in my decade or so here. And that's just our philosophy. We're going to hire the very best people we can. And hopefully they want to stay. Not all do. We've had people who go into academia, want to go into the government, have all sorts of different interests. And we support them there. But for the folks who want to stay and make this their home, I think we've been able to do that. And that's not me. That's coming from a lot of support from the firm. There probably aren't a whole lot of firms for a practice of less than a dozen people that would make four homegrown partners in a decade. So that's not leverage that a big firm normally would have. But I think they recognize the value and the talent of the people that we're able to bring in.

Khurram Naik: And then help me understand, let's paint a historical picture here to get some sense of trajectory into where we are today and where we're heading. So help us understand what the market for appellate litigation would look like ten years earlier, before you joined. So you joined 2013. What would it look like in 2003? What did it look like in 2013? And what does it look like today? What are the differences at those three points?

Pratik Shah: Yeah. So I would say a decade or two earlier before I joined, there wasn't a big market in the private sector. And quite frankly, that's why in earlier times, I think people stayed in the SG's office a lot longer. There were a lot of assistants at least at the time that I joined or shortly before I joined that had been there decade plus in the SG's office. And I think part of that is there wasn't a private sector option really for you to do that same sort of practice in the private bar. A lot of Supreme Court cases decades ago were argued by the trial lawyer or by the state government person. There wasn't that large specialized bar, certainly not in the private sector.

Pratik Shah: Folks like Carter Phillips and Andy Pincus and those guys on the vanguard, Seth Waxman, Carter Phillips, they started these practices in some of the DC firms. And I think slowly but surely firms caught on that, hey, wait a minute. This seems to be a high value proposition, maybe not just in the bottom line of dollars and cents, but these are bringing on really talented lawyers that handle high profile cases that can add a lot of value to the firm both tangibly and intangibly. And so those grew over time. All the ones that we talked about and then the new ones coming up.

Pratik Shah: So if you go back whatever 30 years ago, it just didn't exist. And then by the time I'm coming out 10 plus years ago, they're pretty well formed. And you have those different models that I mentioned. Now, fast forward, I've noticed the turnover in the SG's office. Three years, people leave. Two, three years. That was unheard of. That was viewed as no, you shouldn't be coming for that short of a stint. I was there six years. And few people stayed a little shorter, a little longer, but that was within the realm. Now I think people are leaving because there are even more sorts of variations on those models, and other things in between. And so the demand has increased.

Pratik Shah: I think there was always a concern. I even remember when people said I was coming out. They're like, geez, the market looks pretty saturated for Supreme Court appellate advocates and I'm not sure what the opportunities really are. And yet year after year people come out, find great jobs, succeed. And it is interesting because during this entire time, over the decades that I've been talking about, the number of Supreme Court arguments has shrunk. Thirty years ago, before managed docket jurisdiction, there were 150 cases being argued. Back when I clerked, 85 cases. Now this past term under 60. So it's a smaller set. Outside of maybe Paul Clement or someone, there aren't a lot of people arguing half a dozen cases a term anymore.

Pratik Shah: But what's happened is that it's really become a developed practice in the courts of appeals, federal courts of appeals. Now in virtually any high stakes appellate dispute, I'm seeing one of my counterparts from the Supreme Court bar on the other side in circuit courts across the country. And so the Supreme Court bar's primary practice for all of us is in the federal courts of appeals. And then that's become an area where, again, I think in high stakes cases, more often than not, you'll see folks with that background doing it, which firms recognize, which clients have recognized, and that's been a driver of growth.

Pratik Shah: And then the other reason why I think the demand continues to increase is regulatory litigation. Not even appeals at all, but they look a lot like appeals. There's no discovery. And that area has really exploded. And honestly, with all the changes, both in terms of how the agencies have been acting, but also the changes in the Supreme Court jurisprudence, no Chevron, major questions doctrine coming along, the judiciary much more skeptical of agency action, federal agency action. So clients challenging agencies' rules, regulations, in all sorts of areas, healthcare, trade, environment, securities, labor, all of that. Now if you look at it, it's almost always someone like me or one of my counterparts that's involved in those litigations, even though they often start in the district court. They work just like appeals, all oral arguments. And then they work themselves up the chain fairly quickly. So the practice has diversified. I've seen that even in my 10 years doing it. I did virtually none of that in my first five years at Akin. And now we do a whole lot of it. And so I think that's all been part of the evolution.

Khurram Naik: So let me make sure I understand the evolution right. So part of it is substantive, that there's a new frontier of disputes around regulatory disputes. And part of it is there was an existing matter, let's say appellate work, there's less Supreme Court matters to argue. But I haven't seen numbers on appellate activity. Has appellate activity changed much, say in the past decade or so? Of matters going to the appellate courts?

Pratik Shah: Yeah, I don't know the statistics on that. What I would say, though, at least anecdotally, is that clients have become more sophisticated about hiring for high stakes disputes folks from appellate practices like ours rather than just sticking with your trial counsel. I think that was probably, and obviously that still happens today, but that was probably how it happened much more often in prior times. You stick with whoever, win or lose, you stick with them, especially if you won. But nowadays, especially the more sophisticated clients and especially in high stakes disputes, as I said, I'm seeing more and more of my counterparts on the other side or the same side of those types of cases. So I think that's been a related development.

Khurram Naik: I think it's interesting to note that in so much of the story you're describing here is one of mobility. It's the SG's office and how tenure is dramatically shorter than before. That's a story of mobility. And then there's also a story of client mobility, of hey, let me send this matter to sophisticated appellate counsel. That's interesting. That's just an interesting story to note. You see this in the legal market as a whole, there's a lot of mobility. Associates, some counsel, some partners, just in every aspect of legal practice and private practice, you're seeing just greater mobility of lawyers and of matters it looks like.

Pratik Shah: Yeah, I think that's right. There's no doubt about it. I mean, you know better than me, but yeah, you see big name partners leaving firms, changing firms. True in the associate ranks as well. And yeah, with matters as well. And it's also with the increasing specialization, that's not unique to appellate law. It's in the law in general. But I think the appellate practitioners have benefited from that in that I think clients want to go to the experts for appeals, and it even gets more segmented. Patent appeal specialists, or people who do administrative law appeals, and all of that. So I think that has also been a contributing factor, increasing specialization for sure.

Pratik Shah: The one other area I would mention probably why firms have found it valuable and you've seen this increase is in pro bono cases. I think firms do find value in being part of that, both as a part of the professional duty of being a lawyer, but also in terms of those being often cases that get a lot of attention and bring positive attention to the firm. I mean, we've historically, and we're not unique among appellate practices, although I do think we tend to emphasize it a whole lot here at Akin, but we've always litigated kind of big pro bono cases over the years, whether it's in, and depending on the firm's bent and maybe the leadership's bent, that might look different, what you define as your pro bono cause. But for us, it's been civil rights, immigration rights, LGBTQ rights.

Pratik Shah: I had the privilege just two days ago to second-chair an argument, which I haven't done in a while, but at the Supreme Court at least, second-chair an argument for Chase Strangio, the trailblazing ACLU lawyer, who's the first openly transgender lawyer to argue in our challenge to Tennessee's ban on gender-affirming care for adolescents. Which was honestly just an incredible experience for me, just being able to work with Chase closely and play that supportive role for a younger lawyer. And he's truly a trailblazing lawyer. He's been litigating these cases around the country. But to work closely with him, and he did an incredible job, and our Solicitor General Elizabeth Prelogar did an incredible job arguing that case.

Pratik Shah: But from the firm standpoint, it's just, to be somewhere where that, I feel really lucky to be an appellate, Supreme Court appellate lawyer. And our practice, I think, feels really lucky because that's just a part of it. It's not like we do that in addition to our job. Often the hours, if you look at our hour-matter hours, some of the heaviest matter hours are Supreme Court cases that we've taken on along the way. In any given year it might be a pro bono, non-billable case in that sense, but that's just part of the practice. We don't differentiate. That's just part of the practice and it's one of the best parts of being an appellate lawyer.

Khurram Naik: Well, you hear from some lawyers a lot of the time that there are firms that have policies around pro bono hours and credits, but at least tacitly and sometimes counter to those rules, there's overt communications about, hey, just limit how much pro bono you're doing, this is too much. So it sounds like your practice is really unique in so clearly being expected to contribute in that way. But a firm is still a business. And so then how do you communicate and get buy-in from the firm just to confirm that, hey, I'm confirming this is still valuable to do? The practice group, that we are still getting compensated for this in every sense. How do you do that? It's such a unique position to ask for substantiation of something that is not revenue generating.

Pratik Shah: Yeah, I think the firm sees the value in it. We've been doing it for a long time and they keep making partners in our group and keep investing as well. So I think they see the value. But I don't want to take it for granted. You're right. Not all firms make that calculus. That's why you don't see marquee appellate practices at every firm, or even firms that have them, you don't see the level of pro bono stuff that we do or some of our peers do. Because I do think we have a leadership that is extremely supportive, that truly believes in it. The chair of our firm is on the board of the LDF. And so I think there is that. It's going to depend firm to firm. And so I think if you're thinking about which firm to go to as a lawyer, that's something to think about, the track record and all of that, because it isn't a given that that's going to be viewed as a high value proposition.

Pratik Shah: Now, of course, we're adding value in all the other ways that I said. The high stakes disputes in the courts of appeals, those are not pro bono cases by any means. When you're getting hired to do those cases by the NFL or SpaceX or whoever it is, McDonald's, whoever our clients are, those are important cases for those clients, important for our firm. And we're able to do stuff that strengthens the other areas. You may say, okay, well, our practice might not be the most profitable, but what we do strengthens the most profitable practices at the firm. I argued the Purdue bankruptcy case, the opioid bankruptcy case, for the victims of the opioid crisis. That is a representation that our bankruptcy group, one of the largest in the country, had been doing for years and years. And in the trade practice, we have the largest trade practice in the country at Akin. And we in the appellate group are leading the challenge on the China tariffs, in the largest section 301 trade litigation in the history of the Court of International Trade. So we're able to add value to the marquee business, profit-generating practices that I think the firm can see in that way, even if we at the end of the day aren't ourselves generating it matter after matter.

Khurram Naik: And then can you speak to origination, because you talked about at least one matter was a product of matters referred from other practice groups. Tell me about the landscape of other practices that are destination practices for appellate matters, because you talk about this concept of now more than ever you're seeing that trial counsel is not necessarily becoming appellate counsel. So it sounds like there's becoming a market for appellate counsel for certain kinds of matters. And certain courts especially require more expertise, like the Federal Circuit has got its own jurisprudence and quirks, and there's a beneficial subset of knowledge of say patent law. So how do you see appellate practices approach business development, just broadly speaking? I guess that's the big picture question, and this question of originating work is part of that.

Pratik Shah: Yeah, so I think appellate is unique in that sense in that I view it as there's two bases to business development. There is internal and external. A significant part of what we're doing, I would say at least half, is still internally generated. Matters that folks in our various other practice areas at the trial level are handling, whether that's IP, like you mentioned, or trade, or labor, or Indian law. We do a lot with our Indian law practice. So forming very close relationships with some of those strongest practice groups within Akin that generate high value work at the trial court level. And so that's an important part, forming relationships within your firm with the people and groups that have the sort of work that is going to generate and justify hiring a high end appellate shop to do it, or that will even be pursued on appeal, whether that's to the court of appeals or Supreme Court. That is an absolute important, critical part of, I think, success of any big firm appellate practice, forming those relationships.

Pratik Shah: And it works, I'm sure, differently within each firm. Like I said, I had the blessing of coming after Judge Millett here who had formed a lot of great relationships and credibility within the firm for us. And I think we've been able to build off of that and expand those relationships. That is a huge part of it. And then the other part is the external part. Over time you develop clients, even if they don't use Akin for some of those other practices. When they have a high stakes dispute or an appellate dispute, or quite frankly regulatory litigation, I mentioned that. That originates in the district court. So they may just come to us. A lot of industry associations, we have relationships with the Chamber of Commerce and others, might come to us directly to handle those. And then of course, there's the occasional pitches you get invited to and based on referrals and all of that. So that's part of it like any other practice. But yeah, the big difference is I think we, at least I view it as, I have this internal and external business development that's necessary to really have a successful appellate practice.

Khurram Naik: And what do you do personally for external business development activities?

Pratik Shah: Yeah, it's different now than when I first started. When I first started, I had never been a partner at a firm, let alone leading a practice or anything like that. Judge Millett was hugely helpful in that and flying around with me to meet all the clients. I just remember the first six months being a blur because I was always meeting clients and giving talks and doing that. And quite frankly, in the government, no one knows who you are. Nobody publicizes anything you do when you're in the government, at least back then, before all the blogs became prominent. People just don't know who you are. So a lot of it is just getting out there, getting people to know you.

Pratik Shah: Now I've been doing this 10 years. And so that part of it becomes easier. You don't have to be out there promoting and meeting with clients. People start to come to you, which makes that easier. But still, I'm doing a lot of talks, especially at the end of the term, beginning of the term, that summer season where the Supreme Court is in recess, DC Circuit is in recess. The nice thing about appellate practice is it does typically dip down in busyness over the summer, which is great. You have families and all of that. There's still briefing and all that going on, but argument prep time goes down. And I replace that with doing talks on the Supreme Court, on appellate advocacy. I really enjoy that. It also happens to have the benefit of getting you in front of lots of different groups, clients, whatever it might be, bar associations, law schools. It exposes you and things happen in mysterious ways. You would never guess some of the ways in which work ends up coming back to you. And so I think that's all part of the process.

Khurram Naik: What part do you enjoy the most?

Pratik Shah: Oh, yeah, probably doing the talks on the Supreme Court. It's an area of, basically my entire career, I've been watching the court and doing it. It's still something I find fascinating and I really love what I do. Don't tell the firm this, but I would do this probably for a lot less. And so it's something I really naturally enjoy. I'll be, for the first time actually since I taught constitutional law after my Supreme Court clerkship, I'm going to be teaching a class this spring at Georgetown Law School on constitutional litigation and the executive branch with Josh Matz. And so it's something I really just enjoy.

Khurram Naik: Is that a lot of work to prepare an outline for constitutional law now?

Pratik Shah: Yeah, we'll see. It starts this spring semester. I mean, it's not going to be a true first year constitutional law class. It's going to be a seminar that talks about case-specific examples of constitutional litigation against the executive branch. And I will certainly be incorporating some of my own cases, which hopefully will help in reducing prep time and still making it more interesting for the students, since I can share some actual firsthand experience.

Khurram Naik: How has the experience of teaching impacted your career? Compared to someone who hasn't taught the way that you have, how is your practice different than somebody who wouldn't have had that experience?

Pratik Shah: Yeah, I mean, probably not a lot. There are some, I'm not going to say it categorically, there are a few academics who can be and make good appellate practitioners. I think Toby Heytens is a great example. We were in the SG's office together. He was a professor at UVA, came over to the SG's office. He was a phenomenal advocate, appellate advocate, now on the Fourth Circuit. But sometimes academics don't make the best appellate advocates because they're thinking big thoughts, concepts, trying to harmonize things, where when you're in an appellate court, you're trying to win a case, or at the Supreme Court, you're trying to reconcile precedent and history, the things that the court is interested in, not necessarily your academic theory. And so I'm not sure that teaching has a big impact on how I practice. Having taught, and again, it's been now gosh almost 20 years since I last taught. So I can't say that. But we'll find out, maybe it'll make me a better appellate practitioner after reteaching this spring. So we'll see.

Khurram Naik: So I want to, speaking of education, I want to go back to your early experiences because there was an inflection point that happened for you, even before you went to college for your education. So can you take us back to your roots a little bit about those early influences and the true threads that sent you on your way? Because I think in many ways, learning about the earliest years helps us understand that your outcome was, it seems like, less predetermined and subject to some early luck and some benefits you received then.

Pratik Shah: Yeah, yeah, and I'm happy to talk a little bit about that. I grew up, as you I think mentioned at the beginning, in Akron, Ohio. And that's where I was born and raised. Like many folks in our generation who grew up with parents who immigrated from South Asia, my parents from India, grew up in a working class neighborhood in Akron, stayed in the same house all the way until after I left for college. Not great schools in our area. I was the only Indian kid in my elementary and middle school. I had a great experience, I will say, and there were challenges along the way. But my brother, who was five years older, I think had the foresight. He went to the high school in our area which really wasn't doing well. And I'm thankful for his foresight. He told my parents, you can't send Pratik there.

Pratik Shah: And so I ended up going to a Catholic high school in Akron, even though I'm not Catholic, never been to a church, and I'm raised Hindu and Jain. But for the education, I ended up going there. And I do think that had a big influence on where I ended up after that. It was a great academic experience there. I ended up applying to Princeton and going to Princeton for college. A large part of that was the fact that my Masi lived in Sayerville, New Jersey. And so that gave everyone comfort that we had someone close by. But I did end up going to Princeton from there.

Pratik Shah: And in a lot of ways, having grown up in Akron where I was the only Indian kid in my elementary and middle school, but we had a small Indian community, on the order of maybe a dozen Gujarati families who lived in Akron who kind of spent the weekends together growing up. I'm still in touch with some of the kids who I grew up with back then on those weekends. It was kind of a second world almost. Princeton felt a little bit like that to me. Not just in the South Asian versus non-South Asian sense, but just in the cultural sense, in that it felt a little bit like I was entering a new world there. Obviously, there were a lot of kids like me from small towns or more disadvantaged backgrounds. But there were also a lot of kids from boarding schools and elite schools and all of that. And so it was an adjustment there. But like anywhere you find your community, you find your people. There was also a small South Asian community of friends at Princeton. I'm sure it's much larger now, but back then, a small group.

Pratik Shah: You find the other folks there. And I did chemical engineering there. And it was a great place to do that. It was a small department, which I found very helpful just given my personality, and allowed me to grow and think about other things. A lot of people who do engineering there don't go on to be engineers. And I was kind of in that boat. I did engineering but didn't want to be an engineer. And it wasn't the most certainly educated decision. But after that is when I ended up in law school. So it was an unlikely, I guess, trajectory in some ways.

Pratik Shah: But if I had to pinpoint, my big brother back then saying, hey, let's send him to this school and open up some opportunities. Made it to Princeton, opened up more opportunities. It's not a story unique to me by any means. All made possible by the parents taking the true leap and coming to this country. And allowing those other much smaller leaps or steps to happen. But my story is not by any means unique. I know a lot of people who probably listen to your podcast can relate to it in a bit. But yeah, that's a little bit about how I got to where I ended up.

Khurram Naik: And look, I mean, you went to Princeton and there's many people who came from very privileged backgrounds. But that one particular part of your story is that you happened to make a list with one Judge Breyer who knew another Judge Breyer. So those are, what are the odds? These two siblings both had the position they had in society. So there's pools of people that had these kinds of outsized performance and we can spend a lot of time talking about whether that's nature or nurture or whatever. But the point is that there's some groups of people that do have some advantages in terms of relationships and networks. And some of what you were talking about early on is that, hey, you were not a natural networker. You had to kind of figure this out from scratch and you had this early version of three bullet points you wrote down to have these conversations with. So I guess I'm curious as a big picture question. Compared to some of those pedigreed peers, the peers who did have the ties to lawyers and did have some insights into, here's how you choose a law school and here's how you think about feeder judges, and all these other kinds of insider information that among comparably talented peers is a differentiator in terms of outcomes. What are the advantages of not having those advantages?

Pratik Shah: Yeah, I mean, I guess one thing you have when you don't have all of that kind of background coming in is you are coming in as a blank slate in a lot of ways. And so you don't have preconceived notions. Like, I had no idea when I ended up at Berkeley law school what I would eventually be doing. I didn't know that appellate law was a field. I didn't know what the Solicitor General's office was. I didn't know about clerkships. I just didn't know that. And so I didn't have any preconceived notions. Whereas I guess if I had come in with a lot of people who knew about things and maybe, I want to be some corporate securities litigator and I wouldn't have considered anything else. I would have gone down that path and done the things that led there and not kind of stumbled into this path that put me on a trajectory to become a Supreme Court appellate advocate. And so I think there are advantages. You do that.

Pratik Shah: But it is, and I'm sure it's true in every field, the law is the one that I know. It's an opaque process, like clerkships. How do you go about even deciding who to apply to? How do you make that happen? And it can start pretty early on with your grades from the first year. But I think when we were in law school, I think you applied just after your first year. So you only had a year of grades. How do you figure out how to do that?

Pratik Shah: And so finding mentors is, I think, a hugely important thing. And we had at Berkeley, like all law schools, our affinity groups, which were strong. It was in the aftermath of when they had ended affirmative action. So the affinity groups placed particular emphasis on those communities. And that played a role with me, as I mentioned, meeting Chabria and having his input and other students there. I think it is super important. Now we have, I think, many more formalized ways in which to do that. There's the Appellate Project, a great organization that matches up first generation law students and law students of color with more senior members of the bar. I'm sure law schools have more formal programs and all of that. But I do think it's an important thing to help shed light on what can otherwise be a pretty opaque process.

Khurram Naik: So, speaking of opaque processes, I think a lot of people don't understand the behind the scenes about how the Supreme Court makes their decisions, how ideas are socialized, and how they end up drafting their opinions. And so you, as a clerk, have a unique perspective on the court. And I recognize the court has changed in terms of how they worked together and worked on their opinions. But it would be hard to miss this opportunity to ask you about advocacy and your principles for advocacy. So let's start with briefing and oral advocacy. Let's start with briefing. Tell me about, at the highest level, what are the three bullet points, if you will, for your principles for appellate briefing?

Pratik Shah: Yeah, so I mean, I think the overarching thing about briefing is, you want to build a narrative so that the court wants to rule for you. And here we're talking about Supreme Court briefing. Almost never do they have to rule for you. They're the Supreme Court. They can change the precedent. They can do anything they want as broadly or narrowly as they want. So if we're talking about Supreme Court briefing, you really need to come up with a narrative that makes them want to rule for you.

Pratik Shah: Now, how that's done is going to depend a lot on the case. There are a finite set of tools that you're working with. In some cases, it may be the precedent on your side. In other cases, it may be the text on your side. In other cases, maybe neither of those are on your side, but you've got policy and common sense and equities on your side. So depending on what sort of case it is and which tools are going to be strongest for you, it's shaping that narrative around whatever tool is going to be most effective for you to get the court to want to rule for you. And so that's, I guess, at the highest level, that's kind of how I think about it at the outset of a case at the Supreme Court, which is maybe different from briefing before the lower courts.

Khurram Naik: And then in terms of, you've got this raw matter from the trial court. And so maybe we can expand this conversation to appellate briefing as well as Supreme Court briefing. You've got this raw matter. How do you shape that to go to the appellate level? What is a high level principle you're using for prioritizing arguments? And at a really high level, how do you sit down? What is your order of tasks, your approach to understanding the subject matter you're working with and how you're going to present it?

Pratik Shah: Sure. So I think what most appellate lawyers will tell you, and certainly I'm a believer in this, and again this is not true for all cases, but generally speaking, you're looking for legal issues. Issues of law. A lot happens in trial. And I think this is really the value of appellate lawyers. Sometimes it's easy to get stuck into the facts and the morass of what happened and wait, this was found wrongly against me or my client, or that's not how it actually happened and all of that. I think cutting through that to get to legal issues, appellate judges are much more comfortable when it comes to deciding pure issues of law. So trying to figure out, okay, here's everything that happened. What is the best legal issue that I can present? And I can weave in the equities and the facts and all of that. Let me distill this to two, and I don't want ten, I don't want eight. I want like, give me one, two, max three, in terms of questions presented in an appeal so that the judges can really focus on distilling what might have been months and thousands of pages, if not tens of thousands of pages, of record into a 50 page brief.

Khurram Naik: And then when you think about how to prioritize arguments, are there any principles you're using there? Like let's say there's three arguments, what is a further principle you might use for organizing?

Pratik Shah: Yeah, a lot of that's going to depend on the case, but at the highest level, and this is not rocket science, always start with your strongest argument. Even if it might not logically always be in that way. But judges have limited time, these appellate courts are busy, they get a lot of cases. On any given day they might be hearing four or five arguments. Let's come out with what is our strongest argument and let's make it. And even in that, like I said, I want one, two, or three max issues in an appeal. And then that gets even funneled further by the time of argument. I want to be trumpeting my best argument now. Maybe there are times to pivot if a judge happens to be interested in one of the other arguments. Great, you do that. But usually by the time through that briefing process, through the opening brief and then by the reply brief, if you have a reply, you can funnel it, you get a better sense of funneling it. And then by argument, the idea is to have it really distilled to what is your best argument.

Khurram Naik: And do you have a formula for how you prepare for oral argument?

Pratik Shah: Yeah, that's changed over the years. In the early years, in the SG's office in particular, when you're getting ready for argument, I used to, for example, one of the things I used to do is I used to write out questions. And I would do Q and As. And I still do that to some extent, perhaps less than I did then. You would write out all your Q and As. But the thing that was different back then is I would actually put those questions, write out those questions on pieces of paper or note cards or whatever. And I would give them to my wife, who is not a lawyer. She's a pediatric oncologist, has little patience for legal discussions and even less patience for me.

Pratik Shah: And so I would give them to her. And this was in the pre-kid era, before we had kids. And she would randomly pick out one of the cards, ask me the question. And without fail, after about 20 seconds of me talking, she'd be like, I'm bored, move on. And so it would force me really to crystallize my answers into succinct nuggets.

Pratik Shah: Now I'm going to sound really old, but I'll say, back in the old days of those Supreme Court arguments, before the post-pandemic changes where they changed the format of arguments, that was truly the challenge, because the questions were relentless. There are still a lot of questions in Supreme Court arguments if you listen to them, but they were really relentless in those pre-pandemic days before you had this protected round of questioning at the end. And so you really needed to be able to succinctly answer things and then pivot on to something else because you really just didn't have that ground. So again, I sound like an old man, but back when Supreme Court arguments were really hard and challenging. They're still hard and challenging, but that was a particular skill.

Pratik Shah: And so that was something I used to do, answer questions that way. And then now, once we had kids and all of that, that all fell by the wayside. And I fell into my preparation and doing a lot of the same things. Obviously, I'm going to reread the briefs closely. I'm going to come up with my few key Q and As. All of that I still do. The most important part of preparation, though, which is true then and true now, I'm a strong believer, and this is the Solicitor General's office model, is moot courts. That's now become ubiquitous, I think, in the appellate bar. But it really started in the SG's office. We did two moot courts for every case in the SG's office. I still do that now today for any case that I'm arguing here in private practice. And we do that for all our cases. We do two moot courts, whoever's arguing, doesn't matter. And we have people asking questions who have not worked on the case previously. They pick up the briefs. They read them just like the judges would. And you do an hour of Q and A, and then debrief to do it better. There's no better practice I found for preparing for argument than that.

Khurram Naik: Well, on the topic of what you trained at and learned at the SG's office, and you trained with people like Seth Waxman, you trained with people like Sri Srinivasan, how does your style differ from some of these key influences?

Pratik Shah: Yeah, there are different styles, obviously, of Supreme Court argument. You've got to be true to what you're comfortable with and your personality. I mean, Paul Clement, who hired me, who's kind of one of the best Supreme Court advocates of his generation, I think Justice Kagan described, I think the words she used are heaters and chillers. He tends to amp up in an argument, amp up the energy, a very lively argument style. And then on the other side of the coin, there are people who tend to be very tempered, very measured in the way that they're arguing cases. I think of Leondra Kruger. We were assistants in the Solicitor General's office together. She's now a justice on the California Supreme Court. But if you go listen to one of her arguments, very soft spoken, brilliant arguments, but just bringing the temperature down and calm, cool, and collected no matter how pointed or how aggressive the questioning might be.

Pratik Shah: So I've tried, I've learned from watching all of those folks. Some things you can imitate, some things you can't, and some things you have to be true to your style. I guess others would probably be better suited to describe where I fall in that spectrum.

Pratik Shah: I will say though that sometimes you have to adjust for the case, the type of case that you're arguing. The example that comes to my mind, which I think was out of my normal style, out of my comfort zone, was the Purdue opioid case that I argued last term. I was arguing on the same side, and I think there are different variables you have to keep in mind when you're an advocate, but I was arguing on the same side with Greg Garre, who's representing Purdue. And Greg by personality, Greg is a phenomenal advocate. He was one of the five Solicitors General who I served under. And just an awesome person, very low key, that is Greg, measured, methodical. And quite frankly, representing Purdue, that probably fit appropriately with the demeanor there, answering questions in a low key, methodical way, sticking to the law.

Pratik Shah: I was arguing with him on behalf of all the opioid victims and all of that. And so I knew that my role was really to channel the victims' voice. And so I think it's Justice Kagan who said during that argument, wow, Mr. Shah, you're being very emphatic. And so I think she recognized that it was not my normal style, but I think it was the right thing to do for the clients there. And the right message to send for the court, to get across the equities and the importance of the case there. So I think there are going to be different styles. Great advocates have different styles. So there is no one style. You have to see what fits your personality, what you're comfortable with, and go with that.

Khurram Naik: Maybe this is a dumb question. Justice Kagan knows your style. What do you think is the actual impact of you varying how you approach the case? Okay, you're choosing an emphatic style, which makes sense. It matches the demographic you're serving. And just so too, the corresponding, Purdue is chastened by all its impacts it's had. There's no dispute about the negative impact that opioids have had. And the only question is what to do about it. So it makes sense that you chose that style. But what do you think actually was the impact of choosing a different style in that moment?

Pratik Shah: Yeah, well, I don't know, you'd have to ask the justices. We still came up a vote short. But I think it allowed us to communicate some very important points that were reflected, unfortunately for us, in the dissent, but came through and I think impacted the questioning that the justices did. You never know, obviously it's hard to know how it would have turned out otherwise. I think it was the right call in that moment. But yeah, you've got to kind of do what makes sense to you and hope that that resonates with the justices.

Khurram Naik: Well, maybe, and again, with the repeated caveat that the court has changed over time and in composition and how it operates. But at the time of your clerkship, what was the practical impact? Help us understand what really happens at oral argument and the practical impact that has on shaping judges' decisions.

Pratik Shah: Yeah, I think different judges will say different things. I think what you typically hear, which is what I tend to agree with, and this may differ a little bit between the Supreme Court and lower courts, is that I think oral argument generally makes a bigger difference in the courts of appeals than it does the Supreme Court. And you can kind of probably see why. In the Supreme Court, these are justices who have very well formed views. Now, I think there are a subset of cases in which oral argument can make a difference and does make a difference and certainly makes a difference in a much bigger number of cases as to how the opinion is written. But as to the ultimate result, I think briefing ends up being much more important than oral argument, generally speaking, in the outcome of cases.

Pratik Shah: You can lose a case at oral argument pretty easily by making bad concessions and making mistakes. I think it's less common for you to be winning cases at oral argument. But it does happen. And so obviously, you want to be as well prepared and positioned as you can to maximize the odds of that happening.

Khurram Naik: With that in mind, your approach to oral argument then is playing defense to make sure you're not giving up anything?

Pratik Shah: Oh, no, no, not at all. I think that's just something that you don't want to do. I don't think you prepare not to give away the case. I've seen it happen a fair bit. But I think that just comes with the territory as an advocate. No, you're trying to frame the case in the best possible light for your client, for your position. That's what oral argument to me is about. And of course, addressing the hardest questions and the biggest vulnerability in your case because judges will ask about that. And so you have to take that head on. So I think that's the biggest role, your biggest role in oral argument.

Khurram Naik: Look, I mean, from what you describe about your appellate practice, it seems like even with all the changes you described, increased mobility and then increased competition, all things considered, an appellate practice still seems very glamorous. So what are the reasons why a skilled litigator, maybe someone who clerked Supreme Court, let's say, what are reasons why someone might pursue a trial court practice rather than an appellate practice?

Pratik Shah: Yeah, that's a better question for the trial court litigators who you interview. Whatever I've heard over the years is some will say, oh, well, appellate litigation is like playing tennis without the net. I mean, you don't have that challenge of all this stuff that goes on in a trial court and the back and forth and the cross-examination, and all those kind of, I guess, My Cousin Vinny moments or whatever.

Pratik Shah: To me, at least from my perception and understanding of trial practice, what I appreciate is not having to deal with all the hassle that litigators often have to deal with, real litigators who do trial court litigation, have to deal with in terms of, gosh, discovery disputes or nasty grams between lawyers over all sorts of things. That is by and large absent from an appellate practice. Usually the only things you're procedurally fighting over are like briefing extensions, which usually everyone agrees to, or things like that. There just isn't that much to fight over other than the substance of the case.

Pratik Shah: And so, now, the one change for me, as I mentioned, the last few years doing regulatory litigation in the district courts, I've now encountered that more. And that's reaffirmed my belief that I chose the correct path being an appellate lawyer because I don't enjoy those fights over procedural things and timing and preliminary injunctions and all of those things that seem much less orderly and don't really go to the substance of the legal issues in the case.

Pratik Shah: The other benefit, I guess, in the appellate bar is because it tends to be a lot of repeat players, especially in the Supreme Court bar in particular. But as I mentioned, I often see them in the courts of appeals. You have that personal relationship. And so that also, I think, makes it much easier in communicating, and there's a lot less of the games and nastiness and all of those things that I think are more common in other types of litigation.

Khurram Naik: Okay. So still basically only reasons to be an appellate lawyer. Okay. Got it. So for all the associates who are listening to this, or maybe law school students or even earlier, who are considering a path to appellate litigation, how do you even think about guiding someone about that? So we already know someone has the intellectual prerequisites and dispositions to enjoy the kind of subject matter of appellate litigation. We've already covered why to pursue it. Maybe more tangibly, how to pursue it.

Pratik Shah: Yeah. Appellate is a field in which there is, in many ways, kind of an established track. And so it's a pretty known path that you can follow and embark on if that's something you want to do. Clerkships are the starting point. And in particular, clerking for some sort of appellate court is, I think, an important step in that process. And so I always emphasize to anyone who's interested in becoming an appellate lawyer to really think hard about clerkships and doing a clerkship and taking it from there.

Pratik Shah: Now, there have been circumstances, but they're unusual. I mentioned Margo Rascon earlier, one of our associates who argued in the Fifth Circuit. And she came to us from Georgetown directly having not even clerked yet. She had done night school at Georgetown and gotten some bad advice that, oh no, night students aren't going to be able to get good clerkships or whatever. But then she took a class with Judge Millett, who was teaching there. And I think Judge Millett told me like, she's the best writer she's ever had in any of her classes. And so we brought her on. She was fantastic. And then once she was here, she applied for clerkships and got an A-plus clerkship, Judge Colley and Judge Kethledge on the Sixth Circuit, and then came back here. So there are ways to get around it.

Pratik Shah: But the typical path, you do your clerkship. And then you'd think about joining one of those appellate practices. Obviously, a Supreme Court clerkship would be great. And then joining one of those appellate practices. But there are other opportunities as well, either at the outset of your career or once you've done this for a few years. The Department of Justice, outside of the Solicitor General's office, has stellar appellate components in the civil division, the criminal division, environmental division. Various components within the Justice Department have their own appellate sections. They have an honors program to take young lawyers. And you get to start arguing cases very early on in the federal courts of appeals.

Pratik Shah: State Solicitor General's offices, now that's another new development. Didn't exist when I was coming out of law school. But they have now developed, much in the mode of the federal Solicitor General's office. The states having very sophisticated and high quality Solicitor General's offices, that's opened up a whole number of opportunities for young lawyers in the appellate space. So I think in some ways there are more opportunities than there used to be.

Khurram Naik: Why did state Solicitor General's offices arise? Why didn't they happen before?

Pratik Shah: Yeah, same development. Increased specialization, realizing the value of having these. And now you'll see a whole bunch of states with former Supreme Court clerks and others as their state Solicitor General. Often pretty young lawyers as well, which is opening opportunities for younger lawyers to take leadership opportunities in that avenue. And that's red and blue states. You've seen that phenomenon in both. And that's been part of the trajectory in this increase. In the Trump administration, blue states taking the lead in challenging Trump policies. In the Biden administration, red states taking the lead. Those suits by and large being led by the state Solicitor General's offices, who have now become pretty high powered appellate shops.

Khurram Naik: Well, so it sounds like, you make all these joking references to how old you are and how ancient your experiences. But what I'm struck with is, I think probably Justice Breyer did have an impact with your optimism. You really are someone who any number of people would be tempted to describe changes as for the worse. But I haven't heard you describe the overall trajectory of the appellate bar in any of those words. There are challenges and there are things maybe that you disagree with. But overall, it just creates more and more opportunities for litigators to develop their craft and develop business. So I think I'm struck with that optimism that you have. And I'm glad we sat down to talk.

Pratik Shah: Yeah, it's been a lot of fun. Thank you, Khurram.

In this conversation, we go wide. We talk about how lawyers can borrow storytelling and character-building techniques from professional wrestling, why low-variance decision-making is the key to sustainable success in litigation, how the second fundamental theorem of calculus connects to neutral thinking under pressure, and what Tim learned about deliberate strategy from watching a Korean entertainment conglomerate achieve its global vision. We also get into emotional intelligence, the value of debriefing with opposing counsel, and how golf has reshaped Tim's self-talk.

Keep reading below for the full link to the episode and the full transcript of our conversation.

Top Insights

Below are the highlights of our conversation:

• Lawyers Are Storytellers, Just Like Pro Wrestlers: Tim draws a direct line between what professional wrestlers do in the ring and what litigators do in the courtroom. Both professions require you to build a credible character, maintain consistency, and command your audience through delivery, not just substance.
• Low-Variance Decisions Compound Over Time: Tim caps himself at roughly 20 high-quality decisions per day and deliberately avoids high-variance choices in litigation. Over the course of a trial, a series of steady, low-risk decisions compounds into a more reliable outcome than swinging for home runs.
• The Second Fundamental Theorem of Calculus and Neutral Thinking: Drawing on the book "Getting to Neutral" by Trevor Moad, Tim explains that before you can move in a positive direction, you have to pass through zero. When something goes wrong at trial, the goal is not forced optimism. It is getting back to a level-headed assessment of what is still possible.
• Client Satisfaction Equals Expectations Minus Outcomes: Tim uses a simple formula: your client's satisfaction is determined by the gap between their expectations and the actual result. Since you cannot fully control outcomes, the highest-leverage move is constantly managing and resetting expectations throughout the life of a case.
• Debrief With Your Opponent: After a settlement or trial, Tim regularly sits down with opposing counsel to exchange feedback. What worried you about the case? What did we do well? This habit creates a learning loop that most lawyers never access.

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Full Transcript

Khurram Naik: This is Khurram's Quorum. My guest today is Tim Yoo. Tim is a partner at Bird Marella, and he's one of the most well-rounded lawyers I know. It's not a lot of lawyers who could reference the second fundamental theorem of calculus and The Undertaker. We ran pretty wide on topics here. I'm hoping we can bring Tim back for a second round.

Khurram Naik: All right, Tim. Well, I am really excited to sit down with you. This has been brewing for some time now, and we are, I think we could riff for a really long time on a wide range of topics. I'm super excited to see what we have time to get into.

Tim Yoo: Likewise, I've been looking forward to this for a while as well. I know that when we first sat down for lunch, and just, yeah, like you said, riffs, I think we were talking for a long time, and it just felt very natural. It felt like I knew you for a really long time, so I'm looking forward to this as well.

Khurram Naik: Cool. All right, so you have, I think just big picture, something that strikes me that's so interesting about you. We were just talking a little bit, and we'll get into it later on, about some of the quantitative approaches you took to finding your spouse and how that worked out. But so, you know, you went to Caltech, you were this applied math guy, so in many ways you are a product of that training, but you also are very eclectic in the kinds of ideas that you pull from, the disciplines that you pull from. I think one of the most interesting ideas, or set of concepts, that you riff on are the parallels between your work as a litigator and the practice of pro wrestling. So can you tell us a little more about your love of pro wrestling?

Tim Yoo: Sure, absolutely. Well, first of all, I think it originated from when I was a child growing up, so it's very similar, if you ever seen the movie Minari, that was a critically acclaimed film a few years ago, starring Steven Yeun. There's scenes where he's basically a Korean American growing up in the 1980s, which was very similar to my upbringing. And one of the memorable scenes I think in that movie is that the child is spending time with the grandmother and they're watching professional wrestling together, because there's something about that, there's something about the theatricality of that, that appeals to, I guess, both young and old. So that was actually right on the nose in terms of, I think, how I grew up, where I remember spending a lot of hours on the floor, where my grandma was on the couch in Texas and we were watching pro wrestling on Saturday mornings. So I think that's where the genesis of that, I guess, lifelong interest kind of grew from.

Tim Yoo: But yeah, to your point, I definitely see a lot of parallels between what we do as lawyers and especially as litigators versus what pro wrestlers and the performers in that world do, because first and foremost, I think that, look, they are storytellers and we are storytellers. I think the big difference is that, look, they tell stories with the action in the ring and with their bodies and how they interact with each other. And similar to our world as lawyers and certainly trial lawyers, we're trying to tell a story because we use our words and sometimes we use body language and our intonations and our facial expressions and things like that. So I think there's a lot of similarities in that regard.

Tim Yoo: I also find it fascinating that if you listen to any of them speak, like for instance, if you listen to a podcast or if you listen to any mainstream media or appearance in which a pro wrestler appears, they're excellent storytellers, first of all, because I think there's a very strong oral tradition in that industry. Because if you think about it, they spend the bulk of their time in cars where they're trying to go to 300 shows a year. So a bulk of that time is making towns, going from, let's say, LA to Sacramento, Sacramento to the next town, and they're spending hours in cars. So they're just sitting there telling each other stories, working on their delivery and working on the payoffs and things like that. So if you listen to them speak, I find them to be really the best storytellers around.

Tim Yoo: And the other thing that strikes me is that they also have, they care a lot about their profession. They care a lot about their jobs and how to be effective at it and how to get better at it and how to improve what they call their presentation. And their presentation consists of a lot of different things. It can consist of, most basically, their appearance. Obviously they spend a lot of time in the gym, but they also think about the other aspects of their presentation in terms of their outfits, how they walk to the ring, how they walk out of the ring, how they move, sets that they use that are parts of their character.

Tim Yoo: So I think that's very similar to what we do as lawyers because if you think about it, I mean, even from the very first client intake meeting, you're trying to project something. And hopefully the thing that you're trying to project is a level of credibility. And that credibility can come from the words you say, but also how you say them, how you conduct yourself, how you command a room or read a situation. So all of those things I think go into engendering credibility at your first client meeting. I think that extends all the way to the time that you're ready to stand up in front of the jury and say, good morning or good afternoon, my name is Tim Yoo and I represent Acme Corporation. The jurors or whoever it is or the judge is going to make a snap judgment on you about whether you're credible or not. So I think all of that is part and parcel of the presentation, which is very similar in my view to the pro wrestling world. I could wax on for a long time about this, but certainly, if you want to ask me specific questions, I can expand further.

Khurram Naik: I do, because I know you have more to say about wrestling and the structure of the storytelling in wrestling for sure. So we'll pick up on that shortly. But something you just said is, you know, establishing credibility in, let's say for instance, a client intake meeting. So yeah, I've observed, you know, like if you're a litigator, you go to lots of status hearings, you can observe how litigators establish credibility in a courtroom. So I think that's, I mean, you can see a lot, observe a lot, and it's free, it's public. I think what's more difficult is to get information or insight into how people establish credibility with clients. And so do you believe that you have a set of principles or techniques that you use to establish credibility with clients? I'd be particularly interested, you know, if that's different things in person, different things over phone call. Tell me about that.

Tim Yoo: Yeah, I think, I don't know if it's like a technique, but I think, and this is very simple, but a lot of it is just listening to what they say. You know, I worked very briefly in a sales job, where I used to sell phones for a time, but a big part of sales is they say that, look, you need to qualify your customer, meaning you need to figure out what their issue is and what they want to accomplish. And hopefully you can do that as soon as possible. So a lot of that is asking a lot of questions, sort of, what do you use your cell phone for? Do you take a lot of pictures? Do you play games? Do you call your grandkids? Do you do video calls? Things like that. So you're qualifying the customer.

Tim Yoo: So I think client intake is similar where you're asking them a lot of questions about what their particular issue is, and that means that you're necessarily going to be a good listener. I think you have to be a good listener. So that almost goes without saying. But in terms of the credibility, it's also, I think it's a combination of, hopefully they're consulting you in an area in which you have a level of expertise. So I think that needs to come across, that this is an area where you have a lot of experience, a lot of knowledge. And for me, I'm not afraid of the "I don't know" answer. So I think a lot of times when you have a discussion and you're supposed to be one of the foremost people in a field and a client asks you a question, I think sometimes you may lose credibility by fumbling around and hemming and hawing. So I'm never afraid to say, I don't know the answer to that question. It's an easily knowable question, hopefully. If it's not a knowable question, it's not something that can be readily figured out, then I'll tell them that as well.

Tim Yoo: So I think that ties back into this notion of, you need to project credibility and you need to foremost have confidence in what you're saying. And I think that from the listener's perspective, the amount of conviction that you have when you're delivering your advice or your recommendations is proportionate to how much confidence they're going to have in that recommendation.

Khurram Naik: So I think going back to the wrestling analogy, it sounds like there's two dimensions of practice that are interesting: credibility with your client and then credibility with, say, opposing counsel and the judge. And of course there's overlaps between these, but in some ways these are just different functions. And so maybe going back to your wrestling analogy, can you parcel out the ways in which a wrestler builds his audience, builds his supporters, while also establishing who his enemy is and what differentiates him from his enemy and why he should prevail? Because it seems like the oral, I mean, I'm not particularly familiar with wrestling, I've seen some of it, but it seems to me that it's not about athletic expertise or prevailing that way. It's about who has the better story and having that story prevail. So can you speak more about that, how you build your audience and then how you think about opposing counsel and judge, and how you build credibility with all of these?

Tim Yoo: Yeah, 100%. So I will let you in on a secret, and I'm hoping I'm not divulging or spoiling anything for the audience that's listening, but yes, pro wrestling is not a genuine athletic competition. It is essentially like a live action morality play in which things are predetermined and things are largely choreographed to a degree. So you're absolutely correct. It's not a genuine contest of who is trying to win. But I think what's important about that, though, once you acknowledge that and once you sort of recognize and appreciate the premise of it, is that it's still very important to maintain the credibility of a character. Because the big conceit of that is the audience members, including me, we want to suspend our disbelief for that amount of time. We want to be completely enamored and completely lost in that world for whatever amount of time that we choose.

Tim Yoo: So it's important for the characters and the performers to stay in character, not do things that would take you out of that moment. It'd be no different than if you're watching Mission Impossible and Tom Cruise playing the Ethan Hunt character and you've invested into this Ethan Hunt character and you believe the world that they're in, if he all of a sudden stops and says something as Tom Cruise and it takes you out of that. I think it's very similar. So it's important for the performers themselves to maintain consistency and continuity in their characters.

Tim Yoo: So for instance, if you have someone just as an example, let's say The Undertaker, who is essentially the walking undead or somewhere in between mortal and immortal, there's certain things that that character is going to do and certain things that the character is not going to do. And he in particular has done a great job of doing that for close to 35 years now. When he was an active performer for close to 30 years, he never gave any interviews, never, because he always stayed in that character. And he would talk about how when he was walking through airports, he was always going to be that character, whether it was 3 a.m. in the morning or 2 in the afternoon and some children are seeing him. He's always going to stay that way because he wants to make it easier for the audience to buy in and not make it known that this is not a real thing, this is really a gimmick.

Tim Yoo: And you mentioned the role of villains and protagonists in that world. So the protagonists are known as babyfaces and the villains are colloquially known as heels. So there's a dynamic between heels and babyfaces, and just like anything else, you need to have a very dynamic, imposing, threatening heel to allow the protagonist or the babyface to have a worthy foil. So I think another thing they're good at is setting up the conflict. The way that they set up the conflicts is, you make the villain someone who is very imposing, perhaps indomitable. So when the babyface actually wins, then that win means something.

Tim Yoo: I think they're very important about treating their opponents with the appropriate amount of fictional disdain. And what I mean by that is they're very good about, when they say something, they never say things like, "Hey, you're washed up, your moves are terrible, I could beat you easily." They never say that. If you listen to them, they'll say things like, "Hey, I think you're a rotten person. I didn't like the way you did that, but I respect you in the ring. You've been doing this for however many years, you're one of the toughest SOBs walking God's green earth. And I hope I can beat you." And that's really how they set up that conflict. Because at the end of the day, if you beat a nobody, then what does that make you? So I think they take that aspect of it very seriously.

Tim Yoo: But I think the performers that tend to be more successful, and we talked a little bit about this in this arbitrary world, no one wins the title in the ring. Someone selects you to be promoted, so to speak, to be able to win that title. And it's not unlike any professional setting. It's a lot like a lot of professional settings, including a law firm setting, where people look at how credible you are, how dependable you are, how you are relating to your audience, whether that's clients or in the pro wrestling world, the paying fan, and how effective you are at that. Those performers who are the most effective, whether that's being the best performers in the ring with technical ability, or the ability to attract a large audience to the live shows or TV, those are the rainmakers, so to speak. Those are the ones who tend to get promoted. And in that world, that's called being pushed. They get pushed, or their storylines are elevated and prioritized. So I think that's another interesting parallel.

Khurram Naik: So is there something, I mean, in law, we have a tendency to take ourselves very seriously. You know, we're working on these weighty issues, we're in these courts, which are very formal, judges wearing this black robe, you don't see that in any other parts of society. So there certainly is a theatricality to it, but it's also very serious. And I guess I'm struck with what you're saying about these professional wrestlers, especially the ones that have endured the most, like The Undertaker, in that the gut level reaction society has to pro wrestling is that it's trivial, ridiculous. And notwithstanding that silliness, it's possible to take something ridiculous very seriously and still proceed with that as a professional. And I wonder if you see any parallels to law, and I wonder if that's had any impact on you.

Tim Yoo: It is. And maybe not to put too fine a point on it, but I think going on what you said about it's a serious profession, there's serious issues, and there's issues that are important to the principals that we represent, and by the principals I mean with P-A-L-S as well as P-L-E-S, so the agent-principal context. For the clients we represent, look, these are very important issues. And this is oftentimes the most important thing going on in their lives, certainly the foremost in their mind. So I think it's incumbent on us, it's mandatory for us to take those things seriously. And there's a lot of parts of the process that are serious. Like you mentioned, we go to court and there's someone deciding these issues and they're wearing robes and it's a very august situation in a lot of ways.

Tim Yoo: But I think that is a little bit different than taking yourself too seriously. So I think there's aspects of it that I think you should allow yourself as a lawyer to enjoy certain moments of levity at times. And to be clear, I don't mean to suggest, I actually have a strong opinion on this, I'm not a fan of humor in the courtroom. I think it's fine to break up a tense moment, maybe with a quip or a one-liner, in very sparing circumstances. But I'm not at all a proponent of trying to cut up and trying to say something clever or even sarcastic or funny because it just doesn't read well on a record. I don't think it plays particularly well.

Tim Yoo: So in the situation of a courtroom, I think it's similar to being like The Undertaker. I'm sure the man himself is a very charismatic, funny guy, but when he's in that ring, there's certain things that he will do and certain things that he won't do. He certainly won't cut up and laugh because he's the very serious undead character. I think that's similar to the courtroom. But I also view it as distinct from, I'll put it this way. Absolutely take the issues seriously and your client's concerns and the legal disputes that they're facing seriously, but give yourself some grace to not take yourself seriously at all times. And if you want to indulge in silly hobbies or silly content, have at it.

Khurram Naik: Yeah, I think that's an interesting point because that comes up for me in the context of how I present myself on social media. So I use LinkedIn a lot and I post very often and have for some years now, and so that's been a growing audience. I mean, that's actually how you and I met. You had a comment on my post, and I thought your comment was really thoughtful. So we just started having a phone call from there, and it just kind of snowballed from there.

Khurram Naik: And so you raise a really good point because I feel like my persona, let's say in law school, I think I was definitely serious about law school but I really liked having fun and making fun of the circumstances. And there were some friends of mine who were just hilarious in law school, and of course there's so much pressure and so much opportunity to have a lot of fun and laugh a lot. And I find myself, I don't really access a lot of that. I don't think I'm as funny anymore, to be honest. And definitely my LinkedIn persona is, there's definitely some people in legal spheres whose persona is "I'm a funny person." These kinds of people get a lot of attention and engagement. And certainly some of them also have serious, substantive, intelligent things to say.

Khurram Naik: For me, I think I might take maybe more of The Undertaker approach. I'd rather have a consistent persona that people know. I'd seen somebody else who has been very prolific and cutting edge in using the internet to grow businesses and media, Tiago Forte, and he had made an observation about a newsletter. He's like, well, a newsletter, you should treat this as a TV show, right? It should be on at the same time every week. And you know what you're getting in that newsletter. Just like with a TV show. Seinfeld's on at 7 p.m. on Tuesdays, you know what you're getting when 7 p.m. rolls around. And so I try for that consistency of persona on LinkedIn, at the cost of, yes, having some fun, cutting loose, whatever. But I'm in favor of that because I think it's increasing a uniformity of experience.

Khurram Naik: And then it also helps me understand. It's kind of like maybe that parable of the cat and the tiger, where the tiger's like, hey, I'm going to teach you all my ways. Tiger taught this cat, cat's like, oh my God, show me your ways. You know so many things. Tiger's like, oh yeah, I got this trick, I got that trick. And hey, I'll show you this one trick. You jump up to the top of the tree. Okay, cool. So then the cat learns that trick from the tiger and then a hunter comes along and is coming at both of them. And the cat's like, oh my God, I'm just going to do the one thing I know, and jumps in the tree. And the tiger's like, okay, how am I going to handle this hunter? I got so many good options. And the hunter nabs the tiger.

Khurram Naik: So yeah, I think I favor having fewer options, which I actually think ties into something really interesting about your practice. You try to make 20 decisions a day. So I wonder if you'd make the connection. I think something really interesting that you've observed about your practice, the ways you litigate, the ways you present yourself in the courtroom, and approaches you take maybe with clients as well, because you talked a bit about client intake and maybe you just have a limited set of tools, which is, hey, I'm primarily here to listen, or whatever. Does that all tie together with this 20 decisions a day? Can you tell us more about the 20 decisions a day?

Tim Yoo: Yeah, absolutely, right. It's become somewhat of my gimmick at this point, but I think the origin of that is that I'd read somewhere that once you make a certain number of decisions a day, you start suffering decision fatigue and therefore the quality of your decisions sometimes degrades. So I can't remember if that number was 20 or 25 or whatever it was, but I decided, look, I'm going to try to keep the number of decisions I make below 20. And obviously that's not possible. You make a lot of choices in a day. But I think it's useful to think about in terms of limiting the number of quality decisions.

Tim Yoo: So for example, I guess an extreme example of this is I remember I went to a boba tea shop once and they asked, okay, would you like a small, medium, or large? Okay, would you like boba or no boba? Do you want 30% filled boba or 60% filled boba? And then, okay, do you want sugar? No sugar? And that's when I said, look, just give me a drink, just make me my drink. And obviously that's an extreme example, but the point is, I think I try to be very deliberate about what I would call the high-leverage decisions I make, and I try to make low-variance decisions where I can.

Tim Yoo: Because over the course of litigation, over the course of trial, and I tell my teams this, I think we should try to the extent possible to make low-variance decisions where the outcomes don't swing wildly. So that means for me, I guess I'm a little bit risk-averse in terms of making a decision that could be a huge home run if it goes well, but at the same time, if it doesn't go well, then it's a complete disaster. So let's say that you make a decision to call a certain witness that you're on the fence about, if he or she hits that piece of testimony or says something about your case, that could be a home run. On the other hand, if that person gets obliterated on cross-examination, it could ruin the case. Then I think that's something I would have to think really hard about, and to me, that would probably fall in the category of a high-variance decision. I'm not saying I'm never going to make that call, but I try to avoid those to the extent possible, because over the course of whether it's 20 decisions in a day or 140 decisions in a week, over the course of a trial, those high-variance decisions tend to compound.

Tim Yoo: So obviously, hopefully by the time you get to trial, you feel enough strength and conviction in your positions that you don't need to rely on these high-variance decisions. But sometimes maybe you're in a position where you're not as strong on the strength of the arguments or the evidence, and you need to rely on these types of decisions. It's similar to, I'm not a gambler myself, but if you go to Vegas and play certain table games, you need to be able to take advantage of these high-variance swings and leverage that in order to have success, because over the course of time, as the sample size increases, the house edge is always going to win. So I view it that way in terms of the decision-making process, and I think that's a way of saying I give a lot of deliberate thought to how those decisions are made.

Khurram Naik: So I wonder if part of that is, somebody who influenced me early in my career as a litigator explained that the key part of what a lawyer is selling is, and it just goes back to earlier where we're talking about credibility, a key part of what a lawyer sells is peace of mind. And so I think, particularly for litigators, litigation is inherently unpredictable, and that's maybe arguably a feature and not a bug of litigation, that unpredictability forces parties to get serious about saying, okay, what are the issues you really want to pair down to and get resolution on? And so in that way, in litigation being so unpredictable, you can't project or fully control outcomes, but what you can communicate to clients and sell clients on is this idea that, hey, we took a risk-adjusted approach on this, and having factored in the variance of the different decisions we can make, this is the best risk-adjusted path we could have chosen. So is that part of your thinking, in terms of client management, to say, here's what to expect and forecast for this case? Is that part of the rationale for choosing those low-variance decisions?

Tim Yoo: It's not only part of the rationale, I think that is the rationale. I think if you captured it in one pithy statement, that's how I would capture it. You're right, you can't control outcomes. So I tell myself this, I try to follow this, I tell my case teams this, but I say, look, our job is governed by, in my opinion, one formula. So I studied applied math in college, dealt with a lot of formulas, but I think in the job that we have, one formula applies. And that formula is: the level of your client's satisfaction in any given situation is going to be equal to the level of expectations they have, minus the outcomes.

Tim Yoo: So as you said, we have a lot less control of the outcomes than we would like to think. So let's assume, let's cede control of that and say we have very little control of the outcome. I think what you have the most control over, not 100% control, but certainly in my view more control than the outcome, is managing the level of your client's expectations. So that's to say that if their expectation is that they're going to hit a home run at trial and win every issue, and that's their expectation going in, and you deliver that outcome and you do great and you hit every issue and the jury loves you and sides with you and you achieve that outcome, well, guess what? Those two things are equivalent, so your client is maybe not going to be that jazzed regardless of the job that you did.

Tim Yoo: So I think that, and that's not to say, I'm not sitting here and saying that I think you need to not be 100% genuine about the expectations, but I do think you need to be very realistic and constantly resetting those based on every situation that arises, because that could change over time. So let's say over the course of litigation, depending on how the ruling on a motion goes or how a certain testimony goes, I think you have to constantly revisit that and update the expectations and adjust them. So I do think that's part and parcel of why, again, in my opinion, the prudent path is to take these low-variance, series of low-variance decisions, because a high-variance decision necessarily means that the outcome could swing wildly, the expectations could swing wildly. And if it's not worth it, it would have to be very calculated. So to your first point, I think that's what permeates everything, abiding by that formula that I just mentioned. I think in any client services business, you have to do that. And foremost is always managing the expectations of the principals that you work for.

Khurram Naik: You mentioned earlier this concept of qualifying in a sales context, which in sales is really just another form of communication and influence. And as a lawyer, you are communicating and influencing your clients. So there's a nexus between sales and client management. And so in a sales context, you mentioned the concept of qualifying. And I also think more in terms of disqualifying. And so as a legal recruiter, I talk to people who are at outstanding firms and doing great work at those firms routinely. And so an early question I have that I revisit is, hey, look, it sounds like you're getting great experience, you've got a great team, and you're at a great firm. Why would you even consider making a change? And so that helps manage expectations and really ensures there's a clear narrative for them for why they would even make the change. And that's something that we can hone in on. And then, okay, so if that is the goal, then let's maintain that goal. Really clarify the narrative there.

Khurram Naik: And so I'm wondering, for you, as you progress in the course of a case, new information arises that can change expectations. I just used this concept of disqualifying, saying, hey, here's all the reasons why maybe you won't make a change. And by the way, in practice, it's almost never the case. It is extremely rare that somebody does not make a change if they are in this path and making a change when they work with me in particular. But I'm curious for you, what is the communication principle or technique you're using for setting expectations and communicating with clients?

Tim Yoo: I think a good start is what I talked about in terms of qualifying your client. So at the very outset, I think one of the first questions I always ask is, what is the home run outcome for you here? That's one of the first or second questions I ask after "tell me what happened." What is the outcome? If I had a pen and paper and this is a script, and or if this is a pro wrestling match and I could book the ending of the match, how do you see this ending? And I think that you have to listen to that and internalize it. And hopefully all the recommendations and the actions that you take are consistent with that, and to the extent practical I try to do that.

Tim Yoo: So I think constant communication is right because obviously if you're not communicating and having an open mind, an open ear and listening, then you're not going to always be attuned to things that could be changing every day. Because obviously, whether it's an individual client or a company that has a lot of different stakeholders with a lot of different interests, their whole paradigm could change day to day. Their expectations at any given piece of litigation could change and their objectives. There could be management turnover and therefore certain things are prioritized. Certain things might be prioritized this quarter that aren't prioritized next quarter. For an individual client, there might be circumstances in their life that change. So their expectations and what they want to get out of it are not going to be fixed and static.

Tim Yoo: So I think it's a mistake if you think that the information you have at initial intake is going to be the same throughout a typical piece of litigation, which typically lasts between two and a half, three and a half years. So at some point during those two and a half and three and a half years, or if it goes to trial it could be longer, those goals and objectives are almost necessarily going to be different. Certain aspects are going to be more important, certain aspects are going to be less important. But I think the point is that you want to always be attuned to what your client wants. So that goes to the basic thing of asking them, having conversations with them, seeking feedback. Let me know your thoughts, asking a lot of questions.

Khurram Naik: Can you go back to, you mentioned you're an applied mathematics major, and so you're using this concept of low variance, you've got this formula. I wonder when you talk about low variance, that's a statistical principle that's effective for understanding outcomes. And so I wonder, are there any other fundamental mathematical principles that you use in thinking through decisions, litigation or otherwise? Something that comes to mind for me is a concept like reversion to the mean. It's a fundamental property of numbers that I think you need to understand. Or you just talked about the law of large numbers as well about the compounding effects of either high-variance or low-variance decisions. Are there any mathematical principles that you think you rely on heavily, or ones you think that more lawyers should be aware of and use?

Tim Yoo: I think reversion to the mean is a great one. I like that. One I thought about recently, and I don't want to get too abstract about it, was perhaps the, I might be messing this up, but as I recall it, the second fundamental theorem of calculus. And I think about that. I thought about that a lot lately in the context of, I read a book recently that I really liked called "Getting to Neutral" and it was written by a guy named Trevor Moad and he was the performance coach for, among others, Russell Wilson, who was a Super Bowl-winning quarterback for the Seattle Seahawks.

Tim Yoo: His whole concept was, it wasn't, hey, you should have this positive mental attitude at all times and have this rah-rah mindset. It was, to the extent possible, always try to get back to neutral thinking. So it's the notion that even if things are going horribly wrong and things are going bad, I think the example I use was Russell Wilson had thrown three interceptions in the first half of a football game. Negative thinking is obviously, we just don't have it tonight, we got to pack it in. Positive thinking would be more like, there's nothing that we can't overcome, we can overcome this if we just try really, really hard. Neutral thinking is more like, okay, I've thrown three interceptions, is the game out of reach? No. Okay, so the game is not out of reach. That means we still have enough time to score enough points to win this game. Then thinking backwards, what do I have to do to score those points? So if I'm two touchdowns behind, I need to score two touchdowns and a field goal or three touchdowns, certainly three more touchdowns than the other team is going to score. So what do I do? What are the things I can do to adjust that?

Tim Yoo: So I think that is the shift to neutral thinking. And the whole philosophy behind that is, if you have negative velocity before you get to positive velocity, you necessarily have to shift to zero velocity, which is where the second fundamental theorem of calculus comes in, that at some point in time, something's moving backwards and you have to have it move forward, and at some point in time the rate of change of position is going to have to equal zero. So I really like this notion of getting back to zero, getting back to neutral, because in the course of litigation, in the course of trial, things like that are always going to happen. And I think you need to have a level head and say, this bad thing happened, this witness or my key witness just gave away the farm, they just admitted to something devastating, or they just produced this document that is not helpful, that has things that are very damaging to my case. Let's get back to, after I dog-cuss myself or whoever that is, let's get back to, well, is this still a winnable case? Can I still prove what I'm supposed to prove? And if the answer is yes, you can still proceed and do that. Then it goes to, okay, then what are all the things I need to do to achieve that outcome?

Tim Yoo: So that's a very long way of answering your question. I think about that a lot, trying to arrest momentum if it's moving backwards, negative momentum, and then steering it in a positive direction, but getting to that neutral place first where you can have a level-headed, objective view of the world, hopefully making a lot of low-variance decisions along the way.

Tim Yoo: So a funny story about that. It's funny, but I happily joke about it. When I'm hosting opposing counsel for a deposition at my office or something like that, I always make sure to offer them coffee or tea, do you want water? Do you want ice with that water? Do you want a mug? Do you want a cup? So I've already burned up half of their decisions before we even go on the record.

Khurram Naik: That is diabolical. But so, actually, I'm interested, when you mentioned reversion to the mean, the first thing that came to mind was that concept, I don't know if it's biblical or not, of "this too shall pass." And what's interesting about that concept is that it applies to both poor outcomes and positive outcomes. And so I wonder, how would you use neutral thinking even when you're doing really well? So you're up, doing really well, and oh man, it looks like we're getting some really damaging admissions at trial or whatever. Do you still do that level-setting, saying, okay, things are going well, but let me make sure, what else could go wrong here? Let me proof against that.

Tim Yoo: I try to, because I think I try to the extent I can to be process-oriented more than outcome-oriented. So I try to focus on what was correct about a certain process and not so much about outcomes that you can't always control, like we talked about. We like to think that we can and we like to think that a certain outcome was a direct byproduct of our inspired thinking or our preconditioned decision-making and things like that. But I think if you're realistic and honest with yourself, you recognize that that's not always the case.

Tim Yoo: So to the extent possible, I try to focus more on the processes. And for instance, if there's something wrong about the process or suboptimal and yet notwithstanding that the outcome was positive, despite perhaps poor preparation or something I didn't anticipate, then I try to think about it in terms of things that could be better about the process. And also at the same time, not throw the baby out with the bathwater when there's a bad outcome, and look more in terms of were there things about that I could have controlled.

Tim Yoo: As you know, in a trial, we don't create the evidence. We can't control people talking about what they saw, we didn't create the underlying events. So to a large degree, we have to work with what we have. Meaning that if you apply the same principles and the same processes to every trial, the outcomes are not always going to be the same. One way I like to think about it is, I've been playing more golf lately, but sometimes I might have a bad swing, I might hit the top of a golf ball, and it might just roll for 150 yards right down the middle of the fairway, which is a good outcome. Other times, I might have a really good, solid swing, have a really good committed swing to it and just not make center-face contact and it might go astray, or maybe I strike the ball really well, and I hit it exactly how that ball is supposed to be hit by that club at that distance, and it happens to go into the water because there's a water trap on this course where there wasn't one at another course.

Tim Yoo: So all I have to say is, I think that you have to look at the way that you're doing something more so than what actually happened, and I know that's difficult. Obviously that's against human nature. But I think in the profession that we have, to a large degree, we have to have that mindset, because I don't think you can go in and have a mindset and say, well, this outcome wasn't good, so therefore I must have done something wrong or I'm no good as a lawyer. And that's not to say that you shouldn't have a level of self-reflection, because it could be that both the outcome and the process were not optimized. But I think if you focus more on the process and how you optimize that, that is key to our profession. And frankly, as part of the job I really like, this notion that you have to always look at your process. I find rewarding endeavors that require a lot of routine and repetition in terms of trying to get better at it. So I think that's a big part of what appeals to me about what we do for a living.

Khurram Naik: So tell me about, it seems like there's an interesting relationship between this low-variance, process-oriented approach to working a case with the practice orientation of challenging yourself by taking on new kinds of cases. And I know you recently had a trial and that was new subject matter for you. How do you think about that? Because that's risky, right? That's risky to take on some unknown new kinds of work. A low-variance approach to the work itself is, Tim, you're a patent litigator by training, so just focus on that, only do patent litigation, maybe even niche more into that. Maybe you're the pharma patent litigator or whatever. Tell me about the relationship between that low-variance, process-oriented approach with challenging yourself, and also keeping yourself interested in the field as you progress, by taking on new subject matter that you're not familiar with that you want to do well with.

Tim Yoo: Yeah, absolutely. And I would say, with very few exceptions, and I think you mentioned some of them, like even within our IP industry, there are certain specialties that even people who have been in it a long time, you would need that specialized training, like FRAND or like Hatch-Waxman litigation or something like that. But aside from those very specific niches, I think that you can abstract any dispute to a principle that spreads across all cases, right? At the end of the day, what we do is we're litigating over a breach of a legal duty. And that legal duty might be conferred by a patent that says that you can't do something for a certain period or others can't do something for a certain period, or it could be conferred by a contract, a piece of paper that says you will do this in exchange for that. And what we're litigating at the end of the day is a breach of that legal duty.

Tim Yoo: So I'm not trying to be glib about that point and say that means all lawyers can do all manners of dispute. But I think you can abstract it enough. And if you abstract it in a way and you tell yourself, is that something that I can do, then I think that's a good way to push yourself. It might not be necessarily in the wheelhouse of things I've done all the time, but if it's something that at the end of the day, we have to go and figure out who's telling the truth, who is making more sense with their positions, how did people treat each other, what legal duties did they have among themselves, who didn't perform that legal duty? I think that's at the core of every legal dispute. So I try not to cabin myself necessarily, but yeah, to your point, there's got to be aspects of it, a subject area that you haven't picked up, or a piece of technology or an industry that you're not as familiar with. And that's also the fun part of it, getting in and doing a deep dive and figuring out the things that matter, the things that don't matter. And that's part of the challenge that goes into this very dynamic profession that we call the legal profession.

Khurram Naik: On the topic of exposing yourself to different kinds of work, I think something really interesting in your background is you're an IP litigator at two great firms in LA, and then you took the unusual step of going in-house to an entertainment company in Korea. Can you tell us some more about how you came to that decision and the impact that's had on your career?

Tim Yoo: Absolutely. I think in retrospect, it turned out to be the most important decision I made in my life, the best decision I made in my life. Categorically, I'll just say it was the best decision I ever made in my life. That said, at the time, sitting there and making that decision, I can't sit here and say it was the byproduct of a ton of precise calculation. That's not to say that I didn't give it some thought and weigh the pros and cons and things like that. I think foremost, I had an open mind about it, and it wasn't a rash snap decision. It was something that was percolating for a few years prior to that, which is this notion of, I'm a Korean American, my parents immigrated here in the 1970s, so I was born and raised in Texas. I grew up here my entire life. I traveled back to Korea frequently to visit my grandparents, and then at some point my dad moved back to Korea, so I had a lot of occasions to go back and spend a lot of time there, but I never lived there. And for that matter, I never lived outside of the US ever. So I figured it was a good time period where I told myself, some time in the next few years, if the opportunity presents itself that I could go live and work in Korea for some period of time, I would have a very open mind to that.

Tim Yoo: So it turned out back in 2013, so it's been 12 years or so, at CJ they had a very specific opportunity where there was a piece of securities litigation, and it was high priority within the company, and they needed someone specific. They wanted someone that had experience litigating in California, because it was pending in California. They reached out to their networks and asked around to see if anyone would be potentially interested, any experienced California litigators who were willing to consider relocating to Seoul, Korea, and taking the job and being responsible for that piece of litigation. So I think it was one of those situations of being in the right place, right time, having enough of an open mind to consider that opportunity.

Tim Yoo: So I took a look and I said, like you said, I worked at two great law firms in LA. Part of the calculus was, law firms will always be there. At least that was my gamble or my projection, and maybe that was prudent or imprudent, but I figured, look, law firms are always going to be there. This opportunity seems fleeting. This is a time in my life where there's not as much inertia to overcome. I didn't have family at the time. I wasn't married at the time. So it was in a lot of ways easy for me to port myself over halfway across the world. So I decided to just take the opportunity, and there's the aspect of YOLO to it as well, right? You only live once, so figured why not. And in retrospect, it turned out to be the best decision for myriad reasons.

Khurram Naik: Well, let's get into some of that. Maybe a first jumping off point is, there was something, there was like a motto emblazoned on the wall there. I'm not sure what that was, but tell me your thoughts on it.

Tim Yoo: Yeah, absolutely. So as you mentioned, CJ is probably the biggest entertainment and media conglomerate in Korea, but it also has a lot of different business units. So it has a logistics affiliate that does shipping and moving, it has CJ Foods where they package a lot of the foods and create a lot of the foods that you might be familiar with in your supermarket. They have a lot of different business lines. But for CJ, I worked at the entertainment side of it, and at the time, this was 2013, they had, like you said, emblazoned on the wall, every wall, every hallway, every workspace, every bathroom, every stall, there was this notion of the great CJ Vision 2020, the 2020 vision. Kind of a cheesy, what I thought was a marketing gimmick, this great CJ 2020 vision. But if you read what it said, it said, look, our mission as a company is that the objective is, by the year 2020, we want every citizen of Earth to consume one piece of K-pop content a week, watch one Korean drama a month, eat one Korean meal a month, or something like that. That was the metric and the standard for success that they wanted, and everything that they did was driving toward that outcome.

Tim Yoo: And at the time, I thought it was silly, I thought it was a gimmick, and frankly, probably snickered about it and thought it was unrealistic. But seven years on and by the time you actually got to the year 2020, I think they either achieved that outcome or got as close to it as anyone probably had the right to expect. And I think to me that was impactful because it showed me that those things don't happen by accident. You don't sort of set out to do something and then just land there. I think it showed me that it was the product of a lot of deliberate thinking and actions behind those thoughts. And if you look now, if you go on Netflix and you see a lot of the top content is Korean content, a lot of the top performers on the Billboard charts are K-pop music acts. I think a lot of that wasn't by accident. A lot of that was a lot of smart and talented people working a lot of hours with a lot of strategic thinking behind that and a lot of effort. And that's the outcome of all that. It wasn't this lightning in a bottle or some phenomenon. It was more of, I view it as more of a byproduct of large-scale strategic action. To me, that was very impactful to see that in action.

Khurram Naik: So what else is the legacy of having this stint in-house? How did that change the perspective? If someone had never worked in-house and just did great work at a great firm, what's the difference in perspective that you have, or the set of tools that you have, that somebody who didn't have that experience doesn't have?

Tim Yoo: I think in a lot of ways, it changes your perspective and your whole paradigm because fundamentally, we're all service professionals. So as outside counsel, we more often than not work for in-house lawyers at companies. So they're your clients, they're your customers if you want to think about it that way. So viewing it from the customer side was very eye-opening. I like to joke that I'm probably the only lawyer at my law firm who's both been a provider of my law firm's legal services as well as a consumer of those services.

Tim Yoo: So if you view it from the consumer-side perspective, I think it's very informative because you recognize, what are the things that make a lawyer user-friendly, so to speak, easy to work with, a pleasure to work with in a lot of ways? What are the things that are important from the in-house perspective? Because when you go in-house, you have a lot of different stakeholders and those stakeholders are different than when you're an associate at a law firm, where those are the law firm partners that you work for. When you're in-house, a lot of times there's folks who are on the business side, a very particular business unit. Whether at CJ Entertainment, we had a lot of different business lines. So at any given moment, you're talking to the folks who are in charge of film production or film distribution, music distribution, figuring out what to do with the next K-pop act or the next piece of content. I think CJ produced "Parasite," which won the Oscar a few years ago. So they had a very robust film division as well and live performances.

Tim Yoo: So at any given point, you have a lot of different stakeholders in a lot of different industries. And you recognize that at a law firm, you have a very focused objective in a sense. And you have tunnel vision about that, and all of your efforts and the time that you spend is driving toward, in my case, handling a piece of litigation. But you realize that when you're in-house, the objective of a company is to make money in a different industry, whether it is to sell out a concert or sell movie tickets or something like that. So thinking about it in terms of how you support them and how your legal function is really only an aspect of that larger enterprise was eye-opening to me.

Tim Yoo: It was also eye-opening in terms of the sense of proportionality, that not every dispute requires the same scorched-earth approach. So there could be a very tailored approach. Sometimes the objective is to be more measured, to be more collaborative, to try to impel an outcome that maybe preserves your relationship. Sometimes you want to, yeah, right, unleash the junkyard dog and take a more aggressive approach. But that whole experience gave me a different perspective on that.

Tim Yoo: And then taking a step back, just having literally a perspective from the other side of the world was very interesting as well. I think that changed my entire paradigm of thinking in terms of "something's better or worse." So after my time there, it was always "things are different," not "better or worse." Different in some ways and similar in other ways. That goes all the way to, there's aspects of living in Korea that I enjoyed more, there's aspects of living in Korea that I enjoyed less. It was just different, not better or worse. Same thing with working in-house or working at a law firm. I think there's aspects of working at a law firm that I personally prefer, there's aspects that I don't prefer as much. So it's just a different experience. But having that different experience was invaluable to give you that perspective.

Khurram Naik: You're interesting about being in-house, and I recognize you weren't in-house at a US-based company, but of course you service US-based companies as well. And I'm curious about, when I hear about these Korean conglomerates, it's very interesting. The United States had its conglomerates phase in like the 60s or whatever. And so in South Korea, they're very successful today, apparently and clearly. But it's definitely not invoked anymore in the US, right? US companies are much more focused on fewer verticals. And I'm curious, is there anything that you think American companies can learn from South Korean companies and what their success was?

Tim Yoo: Yeah, that's a great question. Having lived and worked there and observed it, I think what was striking to me is this notion that most everything is routinized. They have processes and they follow those processes and they're very deliberate and strategic. I'm not saying that US companies don't do that. Obviously, they do. But I think the degree to which I observed it was eye-opening in terms of how deliberate, like I said, deliberate and rote. They're going to chart a direction and they're going to go in that direction and they're going to work really, really hard to get there. So to see that number of capable and talented people working that hard at that scale, it just wasn't surprising to me that they were able to achieve their vision.

Tim Yoo: And then in terms of Korean conglomerates and what they represent in Korean society as a whole, I think that's clearly the reason why Korea was able to pull itself out of a bad situation where 30, 35 years ago, in my lifetime, it was a developing country. You go back to the time when my parents immigrated from Korea to the US, it had a gross domestic product that was lower than Vietnam. It was definitely a developing country and now it's G13 or G14, and I think it's directly a product of that approach and that collective movement.

Tim Yoo: And again, I'm not saying that this is better than or worse than, it's just different, but there's more of a collectivism than there is individualism. And I think there's drawbacks to that as well, but definitely in terms of rote movement, applying something and using the dint of repetition and effort and brute force to get to an outcome, I think that was something that I saw that perhaps there's aspects of that US companies could learn from.

Khurram Naik: And you talked about the 20 decisions concept and trying to have lower-variance decisions and more routines. Is that a legacy of your experience there, or is that something in parallel that you developed?

Tim Yoo: If I trace it back, I think so. I hadn't quite connected the dots in that way before, but obviously, look, I graduated law school in 2007. And I can't quite remember if I viewed the work and the world in that way. So I think you're right. I think it was that time in Korea and seeing it from that perspective and seeing how things were very deliberate.

Tim Yoo: I'm talking about, I remember one of the shows that CJ Entertainment produced was an American Idol style contest, but for rappers, to find the best Korean underground rapper. It was a show called "Show Me the Money," which I really liked. And the way that the judges were so scientific in terms of coaching up and analyzing the contestants was humorous to me in one aspect, but very insightful. They'd have a contestant come up and do their rhyme. And the breakdowns of those were clinical, in a way. They would say, yes, so you should be more mechanical with your breathing, be more consistent with your breathing, especially when you're hitting these rhymes. So your flow could be better. Your swag, your swag was quite good. So your level of swagginess was excellent. And then they would be like, oh, your drip was on fire. And the way that you sort of break that down, where I think if you saw it in a US program, maybe it'd be more ephemeral and more holistic about feel as opposed to a scientific approach to what comprises a good hip-hop artist or a rapper. So it's just a different approach that was interesting.

Khurram Naik: I think you're correct. I think you probably adopted a lot of that about being strategic in your thinking and your outcomes and your strategy. But you have an interesting principle, and you're not the only one who's articulated this, but I'm very curious about how you framed it, that EQ, emotional intelligence, is at least as important as IQ, if not more important. So can you say some more, notwithstanding this systematic and rote and organized approach, about the emotional component? Tell me more about how this concept of EQ differentiates successful lawyers from the table stakes of smart lawyers.

Tim Yoo: Yeah, 100%. You hit the nail on the head. My view of this has definitely evolved over time, whereas before when you say, oh, that person's a very smart person, I would think about it purely in terms of IQ, which is a measurable and is more like a brute force attribute or a measurement that you're born with or you're not born with. I think that EQ, like you said, is at least more than half of the component of intelligence. And I view that now because I think as lawyers, our number one job, by far, everything else is secondary and tertiary by a large margin, is you want to get the fact-finder, the ultimate decision-maker, to want to rule in your side's favor. That's the number one job we have.

Tim Yoo: And that requires, I think, a lot of things. Reading the room, getting a sense of who your decision-maker is and getting a sense of what's important to a jury, what's important to a judge, what's important to opposing counsel, the other side's clients, your clients. I think a lot of that is emotional intelligence. It's astounding to me a lot of times, and I'm not trying to be patronizing here, how you see, if you're in court, sometimes you see people who are not reading the room correctly. So they're pounding a certain argument or they're blowing past the stop sign, the judge is telling them and giving them indications of how they're going to rule and why they're going to rule, or maybe they're on the fence, maybe they haven't decided yet, but someone is not being helpful to their client and pushing a point and not quite reading the room about what the judge in that particular case finds important. So it's actually astonishing to me to the degree that I see that.

Tim Yoo: And that's not to say that I never do that, but I think as lawyers, that's an important part of it. I think an important part of it is recognizing what levers to pull, because as much as we like to think that we're governed by laws and legal principles, and of course we are, but a legal principle, a judge can decide that, look, today I think this legal principle is going to take priority, or I'm going to focus on this case law that you cited because it supports this side winning, or I'm going to decide to focus on this evidence and credit that piece of testimony and not credit this piece of testimony because I think this is the right outcome in this case.

Tim Yoo: And we can have a long discussion about which judicial philosophy makes sense, but I think fundamentally, there's a world that we perhaps ought to live in, and then the world that we actually live in. And that world is predominantly occupied by people who rule and make decisions based on who they want to win. So there's a lot of aspects of that, but I think a big part of it is knowing your audience. And I think knowing your audience starts with having a certain level of emotional intelligence. And I think unlike IQ, that seems to be something that you can develop and hone over time, by having a lot of different interactions, having a lot of client contacts, having interactions and communications with opposing counsel.

Tim Yoo: I think a big part of it is, obviously part of what we do is having, we're necessarily going to be adversarial and we have an opponent. But I think you can also learn a lot from your opponent as well. So for me, I always looked at litigation and trials like a tennis match, maybe because I'm a big tennis fan, but I say that in the following respect: in tennis, you're trying to win zealously, you're trying to compete on every point, you're trying to beat the other's brains out, frankly, within the context of the 78 feet or 90 feet that you have across from your opponent, and within the lines of the court. But at the end of the day, you shake hands with your opponent, and you say, well done. And that's kind of how I view it too. So you certainly have an opponent, but I think there's a level of civility and gentlemanliness that you can approach that opponent with, and you can also learn a lot from that opponent as well.

Tim Yoo: So one thing I like to do is, more often than not, I like to have a debrief. Like if we settle a case, I'll call opposing counsel, or after we have a trial, or if there's a summary judgment or something like that, I'll usually have a cup of coffee or sit down or talk to opposing counsel and essentially pick their brain about, hey, what are the things that worried you about the case? What are the things that you think we did well, or maybe even, what did I do well? What were some of your takeaways? Because I think you can always learn by having this feedback loop. So it could be opposing counsel, it could be your own clients, it could be your own colleagues. But the point is, I think emotional intelligence is the one aspect that you can work on a lot in my opinion, and the one that I think correlates to having successful outcomes.

Khurram Naik: That's a really remarkable idea. I don't know if I've ever heard a litigator do something like that. That's actually a really effective way to learn from opposing counsel in a way that, in a settlement, you're all aligned. And so why not share and debrief on the experience? It's just a free lunch. So yeah, that's a really cool concept. And I wonder if the synthesis between the strategic, analytical techniques that you described here and these EQ components, I want to think about and synthesize another one of your principles, which is that the most effective lawyers are ones that don't think in a straight line. Can you say some more about that?

Tim Yoo: Yeah, and I think that's part of having relationships with your opposing counsel as well, and I'll get to that. But correct, I think our conduct and our profession is guided by the rules of civil procedure or the rules of evidence or things like that. So there's a way to litigate a case in a straight line where you abide strictly by the code, things are due when they're due. I'm not suggesting that you disregard that, but I think that sometimes you can do a disservice to your client by thinking too much in a straight line, by having a level of rigidity.

Tim Yoo: And by that, I mean, it could be, hey, the other side did not abide by the code, these aren't conforming with code, they didn't do this within the 30 days that they were supposed to. We should immediately, or let's say like noticing a deposition, I can notice a deposition within a reasonable time that's not going to work for you, then I'm going to appear, I'm going to take a notice of non-appearance, and we're off to the races because my conduct is consistent with the code of civil procedure. So I think that's what I'm referring to when I say there's ways to do things in a straight line.

Tim Yoo: And then there's ways to do it with more non-linear thinking about what are the outcomes that are mutually beneficial? What are, in this prisoner's dilemma, how do I optimize utility for both sides? And a lot of that is having communications and having a good relationship with your opposing counsel. It's also realizing, thinking backwards, this is the outcome that you want to achieve, and what are all the different ways that are available to achieve that in a mutually beneficial way.

Tim Yoo: A lot of times, especially when you start out as a young lawyer, I think it's easy to set out these long meet-and-confer letters or set your position and cite all the case law that supports your position. I think these days, more often than not, if I get one of those letters from opposing counsel, I will go immediately to the last sentence. And I would say nine times out of ten, it says something to the effect of, "Notwithstanding the positions stated above in the prior five pages, and without any prejudice to our ability to change our position later on, okay, we will agree to your proposal." So that's to say that, look, I think there's a straight-line way of citing the right cases and the right civil procedure sections and things like that. And in a way, I'm minimizing that, but I don't mean to minimize it. I think foremost, those are in service of our objectives. They shouldn't be the tail wagging the dog. They should be used as a guide to govern our conduct to a large degree, but I don't think as lawyers we're necessarily doing a service to our clients by indiscriminately following them without any level of discretion. I think that's a big part of our profession too, to exercise your discretion and your judgment, because at the end of the day, we're getting hired by our clients to exercise our judgment and to make recommendations. And that's something that they can't look up in the rule book.

Khurram Naik: Is there an example that comes to mind where you presented a non-linear solution and that was well received or was otherwise effective?

Tim Yoo: Yeah, I think in a recent trial I had, there was a discovery deadline that we were coming up against. And this is a case that I had come in late in the game, actually after fact discovery. So we were talking about expert discovery and there was something like 20 experts that we needed to depose and figure out the schedule on, and there was limited time. So it was almost like an LSAT puzzle. And I think the prior approach had been sort of, hey, you're supposed to do this, I can't remember if it was three days in advance or seven days in advance, but the point is there was some code provision that said you needed to be done with it a certain time. And I think if you limit yourself to those strictures, there's no way that it could have gotten done.

Tim Yoo: So I remember, I called opposing counsel and said, look, at the end of the day, we need to get these things done a certain amount of time before trial. And for me, I don't care if it's within that prescribed period before trial, we just need to get it done. So how do we do that? So we were able to have a collaborative discussion about, okay, I'll be flexible. I'd say, okay, I can't make that work, but I'll make this work. Not horse-trading in a sense, but it was a real sense of, this is a collective problem for us that we need to solve together. And we were able to do that.

Tim Yoo: So I think that's an example of, it would have taken a lot of letters, it would have taken a lot of threats to seek court intervention or seek relief from the court if we can't resolve this ourselves, which I don't think was going to be a productive use of the client's time. And a lot of times you can cut through that by just having a direct A-to-B conversation with the other side. So I think that's something I would cite as an example of this non-linear approach.

Khurram Naik: I want to double back. You mentioned golf, mentioned tennis. And it strikes me that you are, going back to what you said about wrestling, you are observing top performance in these different spheres. So I want to start with golf. What is it that you've observed? And I know that we've talked before about the rise of golf in South Korea and how much that's a big part of South Korean culture now. So you might have more exposure than other people. Can you say what you've learned from great golfers?

Tim Yoo: I think it's the approach as well. Just like with pro wrestlers that care a lot about their jobs, if you look at golfers, and I don't know if you've seen the show on Netflix, "Full Swing," which was fascinating to me, they profile these different tour-level golfers at different stages. The top guys as well as people who are fighting and competing for their tour card. But I think what strikes me about golfers, as well as all athletes in general, is that they care a lot about the process that goes into performance.

Tim Yoo: All of that, everything that goes into the moment where they step into the tee box on the first tee of a tournament and they swing the golf club and they hit the ball, that's about 10 seconds from the time they go into the tee box and by the time their tee shot is off. But the things that go into preparing for those 10 seconds is fascinating to me. The decisions that they make in terms of where to live in the off-season, a lot of golfers live in Florida or Texas because the ostensible reason is that there's better weather, more wide-open spaces, more access to facilities. The nutrition decisions that they make, the staff that they have around them in terms of their physios and making sure that they have a certain level of flexibility and strength in certain areas. And the way that they track their progress, they track their progress in terms of how much clubhead speed am I generating, how much clubhead speed do I need to generate to hit this ball a certain distance.

Tim Yoo: And if you watch these pro golfers carefully, they're very meticulous about it. There's this funny interview that Phil Mickelson did where he's talking about the science of hitting his wedges and he's talking about, oh, sometime early in the morning, when there's some dew on it, it's not going to come off your club face the same way. So you've got to discount that by five yards. You've got to figure out where you're going to choke down an inch and take another two or three yards off of it. Different types of grass, it also depends on how the ball is lying relative to that grass, whether the blades of grass are going this way or the other way. All of this goes into the calculus of it.

Tim Yoo: So I'm really fascinated by people who take those processes very seriously. And the goal of that is to have maximum performance at one very specific window. So 365 days out of the year, their goal is to make sure that when they're swinging that club for those 10 seconds, they have a certain amount of clubhead speed going in. And in order to generate that amount of clubhead speed, they recognize that they need to move their hips and their arms at a certain speed, meaning they need to have a certain level of strength in their trunks and their legs. And working backwards from there, it's very fascinating to me. So that's kind of how I view it in terms of what are the things that go into optimizing your performance and thinking backwards from there about how you can optimize those different opportunities.

Tim Yoo: And I think fundamentally what appeals to me is this notion that I play tennis as well, and I can hit a good forehand if I have enough practice and repetition. But to me, that's similar to this notion of taking a good cross-examination or taking a good deposition, which is to say that those are products of the amount of time and preparation that you put into it. So when I say I hit a decent forehand, that doesn't mean that I haven't picked up a racket in six weeks and I can go out to the court and immediately be grooved in and hitting good forehands. I need to practice and drill and hit a certain number of shots.

Tim Yoo: And I think no matter how many times you've cross-examined witnesses at trial, how many times you've taken depositions, you've got to take that process seriously as well because it's very process-oriented. And in my opinion, the effectiveness of an examination is directly proportional to the amount of time that you spend preparing for it. So these are all fluid concepts. I would never sit here and say I'm a good examiner or I'm good at taking depositions. I would phrase it as, I know what it takes to take a good deposition. I know what it takes to take a good cross-examination. I know the level of preparation that it takes to do that and the discipline required. So that's kind of how I would view it and phrase it.

Khurram Naik: And then with, I know you've been playing more golf lately, I wouldn't expect, given that you, again maybe similar to the 20 decisions a day, it's impossible that you could be directing the same energy to your work as you are with golf. What are you getting out of playing more golf? What's the impact that's having on you?

Tim Yoo: A lot of benefits, I think. Foremost, it's an outlet, right? We have high-pressure jobs, high-leverage jobs where the stakes matter. And that's great because, I can't remember who said it, maybe it was Billie Jean King, great tennis player, she said pressure is a privilege because if you didn't feel pressure, that means no one gives a damn about what you're doing. So I think golf for me is a good outlet in terms of stress relief. It's also, to the extent that you're walking on the course, a good way to get your steps in. And then the other part of it is having more of a sanguine attitude about things in general.

Tim Yoo: Having more grace with yourself, foremost. I think one thing I told myself in the last couple of years is that before I'd go out there and I'd have a shot and maybe I didn't hit a good shot, more often than not I didn't hit good shots, and I would dog-cuss myself and say, you're terrible at this, why did you do that? I thought to myself, look, if I'm not out there every week on the range practicing that exact shot from that distance with that club at that angle, then I have no right to have an expectation of myself that I'm going to hit that shot well. If it happens to be that way, then great. But unless I'm out there processing that very specific shot, I should have more grace with myself. And therefore the conversations that you have with yourself, be kinder.

Tim Yoo: And I think that helped. And that's contrasted by, look, if I have 140 yards with a seven iron in my hand to the pin, that's a shot that on the range you're practicing basically every time. That's the shot that you practice when you go to the range. You have that club at that distance. So I'm darn sure going to have an expectation of myself to make that shot. And maybe that's different. But those other shots, you just got to have more grace with yourself.

Tim Yoo: So I think my takeaway of that is it just gives you a more sanguine attitude about things, about how, and not to get too philosophical, but look, you got to hit the ball as it lies. So even if you hit a terrible shot and it's sitting in the sand, or it's just a foot off the water, and you have a playable shot, you have to hit the next shot at that spot. Meaning you have to deal with the circumstances and reset. So it doesn't matter how many shots preceded it or how many shots are going to follow, you have to focus on executing that one shot.

Tim Yoo: It doesn't matter how poorly you've played. I think what I like about it is that during the time that you walk to your next shot, and that's a lot of time usually for me because it's probably way off the fairway, you have a chance to reset yourself and say, okay, well, going back to neutral thinking, I've sliced my tee shot way right. Do I have a shot at the green? Can I play this club? Can I hit a shot, get a shot off here, and get it back into play? Okay, if that's yes, then what do I need to do? I need to pick the club and then commit to that shot. And make the shot.

Tim Yoo: So I think that's been good in terms of general mental approach, which I think is a big part of it. I listen to audiobooks, and there's obviously a plethora of these, but it was the mental aspect of golf, and I think there's a companion one for tennis, the mental game of tennis, which I think you can apply across your job and your profession. So that's been great.

Tim Yoo: I mean, look, by no means am I a good, well, you know what, let me qualify that. I recently shifted my mindset on this as well, because I recently read "Atomic Habits," and the big takeaway is that, look, you can set milestone goals of saying, hey, I'm going to break 100 this year. Or you can set habit goals and say, look, to get that, I'm going to play however many rounds. But they say the most important driver of that is to kind of see yourself as a person who does those things.

Tim Yoo: So when I started out, I think for a number of years my New Year's resolution every year was, I'm going to break 100 consistently in golf, and I didn't achieve it. And then I set a milestone goal of, okay, so I'm going to play this many rounds a month to try to get better at it. And I think very recently, I shifted the mindset to, I wouldn't say I'm a good golfer, but I'm a competent golfer. I somewhat know what I'm doing out here. So therefore, before when I have a bad round, I would say, you have no idea what you're doing, you have no clue, you're just a complete duffer, shots are going wayward, and you have no way of figuring out how to get back on course. But now I tell myself, no, you're just having a bad day, or you're having a good day, but the point is, you know what you're doing out there. You know how to swing a golf club, you're a competent golfer. And I think viewing yourself that way has been a powerful mindset.

Tim Yoo: And I think that goes back, I mentioned the book by Trevor Moad, "Getting to Neutral," and he tells a story about, possibly apocryphal, I don't know, but there was an executive that he worked with, and that person thought he was a bad student all throughout high school. So he kind of goofed off and cut classes and things like that. And then he took the SAT, and it turns out that he got like a 1,400 on his SAT. And that changed his whole paradigm, where he said, oh, I guess I'm not a screw-up. Turns out I'm a pretty smart guy. So he decided to go to class and apply himself and study. And then he did really well for the rest of high school, went to a good college, got a good job.

Tim Yoo: And then a number of years later, as the story goes, he gets a letter from the College Board, and it says, oh, look, it turns out that during your testing year there was a mistake, and we counted your verbal score twice. So it's not that you got a 1,400, you actually got a 700. But by that point, it was too late. He had already internalized that, look, I'm a good student, or I'm a smart person. So he started doing the things that smart people do, or in his view, that good students do. So that's kind of how I view it. If I tell myself, look, I'm a good putter, I shouldn't say that unqualified, I think I'm a good putter. And part of the reason is because I have a small little putting area that I try to hit a certain amount of putts every day. So I like to tell myself, look, you're a good putter. You should be able to bury this. You should be able to put this in the back of the cup. And I think that mindset helps a lot, seeing yourself as someone who has certain habits.

Khurram Naik: Yeah. The first thing I want to mention is, you said the word "dog-cuss" a couple times. That's how I know you really are from Texas, because when I moved to New Jersey as a kid, I was so confused. I'm like, oh, these kids are talking about cuss words? What are cuss words? But yeah, look, I think a couple things you said resonated for me. The practice that I have is a yoga practice. And so a couple things you said resonated with me. One is that you observe that you shouldn't talk about, hey, I'm great at depositions or whatever. And the more effective way to frame that is, hey, I know what it takes to be good at that.

Khurram Naik: I've observed that really experienced yoga practitioners have a similar mindset, where it's not, oh, I can do handstands. Handstand practice is a practice. It requires a lot of work, even for an experienced practitioner who is conditioned, and there's a lot of specific muscle groups that you're using for that, and mindset as well. And so I would think that a number of experienced practitioners would not say, oh, I can do handstands. They'll think about, a month before I could do it consistently, it took long practices every day. So that resonated for me.

Khurram Naik: And another thing, at the studio that I'm at now, they do emphasize self-talk a lot. Particularly when you're progressing through class, you're warming up but you're still not in the swing of things, you've not fully warmed up and challenged yourself. And maybe you start to have expectations of, well, especially for someone like myself who has a regular practice, I should be able to do a certain thing today. Well, first of all, there's a lot of variability in our bodies. Our bodies are asymmetric. And on any given day, our body may be responding to something in the world, and our bodies may perform one way or another way. And so the self-talk is important.

Khurram Naik: And it's important to also, I think to your point, rather than saying I'm great at this, putting all this pressure on myself, say, I'm competent at this. I know what it takes to get even better at this. I'm also satisfied with the level of performance given that this is just one part of my life, I'm not a full-time student of yoga or practitioner. And so yeah, I also think one of my big takeaways from "Atomic Habits" was this identity component, that you don't just go through the motions. For some time, I cut out drinking almost five years ago. And if I recall right, early on I was saying, oh, I'm not drinking right now. And then the shift became, oh, I just don't drink. And so just that identity shift, as I recall, made it so much easier to sustain the habit.

Khurram Naik: Actually, I'm just remembering, it's not the alcohol component, it's the caffeine component. That was a harder identity switch for me, because alcohol was much more clearly having a detrimental impact on me. Caffeine was like, I cut the two out at the same time. And I was like, well, I don't know, I kind of like coffee. Everything in society says coffee is a good thing to have. So that was the harder identity shift, going from, oh, I'm not drinking caffeine right now, to, I just don't drink caffeine. So yeah, I think the identity shift is important.

Khurram Naik: But I think a subtle point that you're making is, rather than putting all this pressure on yourself to be, hey, I'm great at this, say, hey, I'm competent and I'm good at this. I know what it takes to be better. And I am good enough that if I'm having an off day, that doesn't dent me. I know that I'm good at this and I keep on at it and keep going.

Tim Yoo: Bingo. So I think you hit the nail on the head. You believe, you have conviction that you're competent at this. And if you're competent at something, like anything else, just like you said, the way that you respond to things happening in the world, you have good days and you have bad days, but it gives you the self-assurance that it's not going to shatter you. Trust me, I've taken a lot of suboptimal, let's just say, cross-examinations or depositions, or not focused on the right arguments in a motion, had a bad day. That doesn't shatter my self-belief or this notion of being self-assured. It's just, it wasn't the best day at the office.

Tim Yoo: I think when you're a young associate or young attorney coming up, that can be similar to a lot of people in their early yoga practice or an aspiring golfer. But if something happened that you could have done better and you tell yourself, man, and you beat yourself over it and you have this self-flagellation about it, I think that's not as productive as just having the right identity of, no, I've earned my stripes on this. I've been around the block enough times. I've done this enough times to know that I know what it takes to be good at this.

Khurram Naik: And you mentioned a few books by now. So I'm curious, as maybe a parting question for you. Are there any books that you've read in the past year, past five years, that have had an impact on how you think about yourself and your progress professionally?

Tim Yoo: I have a few on my nightstand that I revisit from time to time. One of them was "The Credibility Code." That's a lot of what we were talking about earlier, in terms of the takeaway that people make snap judgments about you based on nonverbal cues, in terms of how you conduct yourself, how you hold your head when you're speaking, how rapidly you speak or not, how articulate you are with words, things like that. So I always try to keep that top of mind in terms of what I project into the world and how I want the world to perceive me. And hopefully there's an identity between those things, and I try to get as close as possible. So that's one that's been a helpful guide.

Tim Yoo: I think also reading "Extreme Ownership" by Jocko Willink, the former Navy SEAL, that talks about how the takeaway is this notion of there's no bad teams, there's only bad leaders, and talks about leadership principles and taking ownership of those things. So I would say those are things I think about a lot because more often than not these days, and I don't know if you can see it, but there's a picture of Dan Marino in the back, and I'm not particularly a fan of Dan Marino, but it's really the notion of, I like to view myself identity-wise as the quarterback of my case teams and the one who more often than not has the ball in their hands at critical moments.

Tim Yoo: So just kind of viewing that, that's for me why I think reading books about leadership appeal to me. The credibility side of it is something I'm constantly thinking about. And to bring it back to what we were talking about at the very top of the conversation, pro wrestlers are great at thinking about how their characters come off. One of the big influences in that regard, and one of my favorite performers of all time, is Jake "The Snake" Roberts. And if you hear him talk about how important it is to present a certain image by the way that he walks through the curtain, the way that he saunters to the ring, the way that he has a level of coldness and remorselessness, and how he's trying to portray this very evil character, and the thought that goes into it and the choices he makes to do that are just fascinating to me.

Tim Yoo: So I try to think about that, and I tell my case teams this too, in terms of think about that, like your character essentially begins at the check-in line at security. The way that you put your bags through, the way that you conduct yourself and talk to staff, talk to other people at the courthouse, talk to your teams, and the way that you conduct yourself as you walk into the courtroom. Are you sauntering? What kind of presence do you have? How are you reacting to things that come out during the course of that trial? I think that all plays. So those are things that I think about a lot and try to apply.

Khurram Naik: Super fascinating range of ideas that you've drawn from. I'm glad we had this time to talk. Our time has just blown by. And I know that we would probably have another hour or two in us. So hopefully there'll be a round two another time. Super fascinating, Tim, and it was a real privilege to have you on.

Tim Yoo: I appreciate it. Thanks for having me, Khurram. And yeah, I can talk to you at any time. I really enjoy the conversation. So I'm hoping to do it again soon as well.

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Me and My Wife

Lora and I dig into what it means to take ownership of your trajectory, how fear can become fuel, and why trust is not just a nice idea but a competitive advantage. We also talk about the power of being strategic, the importance of pursuing what energizes you, and how first-generation professionals can create their own networks and opportunities from scratch.

Keep reading below for the full link to the episode and the full transcript of our conversation.

Top Insights

Below are the highlights of our conversation:

• Your Father's Masking Tape: Lora's father worked as a lithographer for 44 years, marking every repair he made with a piece of masking tape bearing his initials and the date. That image of quiet dedication became a model for Lora's own approach to work and care.
• Fear as Fuel: As a first-generation lawyer, Lora channeled fear and uncertainty into motivation. Rather than letting the absence of a legal network hold her back, she used it as a reason to work harder, take ownership, and find creative paths forward.
• Trust Is a Competitive Advantage: Lora explains that high trust makes practice more enjoyable and sustainable. The opposite, not being able to trust anyone, is a dark place that undermines collaboration and career longevity.
• Take Ownership of Business Development: Working with a business development coach, Lora learned that client development does not have to depend on a partner choosing you. You can create your own networking events, build your own contacts, and take control of your professional trajectory.
• Pursue What Energizes You: Lora pays attention to the problems that light her up, from depositions to oral argument, and allows her career to grow around those things rather than forcing herself into a mold.

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Catch the full episode on your favorite podcast platform.

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Apple Podcasts

https://embed.podcasts.apple.com/us/podcast/030-fear-as-fuel-for-first-gen-lawyers-lora-krsulich/id1536579571?i=1000681053968

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Full Transcript

Khurram Naik: This is Khurram, it's Khurram's Quorum. My guest today is Lora Krsulich. Lora taught me a whole new dimension to the practice of law, and that's about trust. She is one of the most high-trust lawyers I've met, and it shows in her career success. After clerking in the Central District of California and the Ninth Circuit, Lora litigated at Susman Godfrey before joining Goodwin as an associate. She is the first associate on the podcast, because Lora is a rising star. Here's Lora.

Khurram Naik: Okay Lora, I am very excited to have you on here and you have one of the most unique stories of anyone I know in law. One of the parts of your story that I still think about, because it's such a vivid picture in my mind and it says a lot about your trajectory, was the day you went in with your dad for his last day of work. Can you share something about that story?

Lora Krsulich: Of course, and I'll just say, I'm very thankful to be on the podcast and to you for taking the time to get to know me and to ask questions in the way that you do with so much insight and care. So my dad, he worked as a lithographer when he first arrived in San Francisco. He had a community of people who were also working in that same lithography company and who placed him there. He was a printer and he worked there for 44 years before he retired when my sister and I were in high school. So he had us come to work his last day to see where he'd been working. We didn't go there regularly at all. It was this printing plant and I walked in. The thing that stood out to me was he worked on the same printer for the majority of his career, and on that printer were little pieces of masking tape that he'd put everywhere. So this printer was just covered in masking tape, and every piece of tape had his initials on it, like RK, and then the date. And when my sister and I asked him what that was, he said, well, that's just reflecting all the repairs I've made to this printer over the course of my time here. And I love that because it's just such a great picture of what he's done.

Khurram Naik: It really is. And you yourself have been repairing and building all along the way. What was your path into law? Because you're a first-generation lawyer. How did you even come to think about law as a career?

Lora Krsulich: Yeah, so I grew up in San Francisco. My parents are immigrants. My dad is from Croatia and my mom is from Hong Kong. And neither of them went to college. They didn't have lawyers in the family or even people who had the means to hire lawyers. So law wasn't really on my radar growing up. But I was always interested in reading and writing and arguing, I suppose. And I had a teacher in high school who encouraged me to think about law. So I went to UC Berkeley for undergrad and then to Loyola Law School in Los Angeles. I didn't really know what being a lawyer meant until I got to law school and started to see the different paths.

Lora Krsulich: And when I got to law school, I was really drawn to litigation. I liked the idea of being on your feet, being in a courtroom, advocating for someone. And then I clerked for Judge Gutierrez in the Central District of California, and that was really formative for me because I got to see so many different types of cases and different styles of lawyering. And then I clerked on the Ninth Circuit after that. And those clerkships were really where I started to build confidence in myself as a lawyer and understand what kind of lawyer I wanted to be.

Khurram Naik: And then from there you went to Susman Godfrey. What drew you there?

Lora Krsulich: So Susman Godfrey was a really special place for me. What drew me there was the trial culture. They have this reputation for actually trying cases, and as a junior lawyer, you get a lot of responsibility early on. I wanted to be in depositions, I wanted to be standing up in court, and Susman gave me those opportunities. I was there for about four years and got incredible experience. The people were wonderful, the cases were fascinating, and it was a place where I really grew as a litigator.

Khurram Naik: So let's talk about trust, because that's something that really stood out to me about you. You operate with a very high level of trust. Where does that come from, and how does it show up in your practice?

Lora Krsulich: Yeah, I think trust comes from my upbringing. My parents, they built their lives here by relying on a community of people who trusted each other. My dad got his job through that community. And so trust was always a value in our household. In my practice, I think being a good litigator and working on larger teams now, you often find yourself working with other lawyers and need to figure out, you need to take the time to identify who those people are and learn about them so that you can trust them when you're doing assignments. And I think that translates over into everything. It's something that I like to do, meeting people. It comes sort of natural to me.

Lora Krsulich: And I guess another thing I would say is the opposite, right. Not being able to trust anyone is sort of like a dark, dark place. The question is, do you really want to practice like that? For me, I want to be a litigator. This is my career. I really enjoy it. I do not want to be in a place where I'm not trusting the people around me, or opposing counsel. I'm going to verify when I need to verify, I'm going to check, but I'm going to trust that the people that I'm with, or the people that I've surrounded myself with, are going to act with integrity and advocate for the clients and do all those things we're supposed to do as lawyers. So it makes practice more enjoyable and sustainable for me.

Khurram Naik: I think part of it too for me has been that I've been able to trust more, the more confidence I have in my skill set. I didn't really have a lot of confidence in myself as a patent litigator. I was mediocre at best. But as a legal recruiter in particular, I think it's been a culmination of my interests and skill set, being very people-centric and community-centric. And so I think there too is a virtuous cycle of confidence in your abilities and then ability to trust other people. Because I think a lot of low trust stems from an insecurity about not wanting to be seen as a fraud or incompetent or whatever. And so then not being able to trust other people and putting walls up because you don't want to be seen. The wall is intended so people don't see that you're not doing your work, but then it's a two-way street because you can't see them and connect and coordinate with them.

Lora Krsulich: Yeah. So for you, I mean, it sounds like you got some early feedback that you were good at what you did. You were taking that position very early on.

Khurram Naik: Did you feel, if mastery is maybe, I think mastery is a process, not an outcome. There are stopping points along the way, you know, on a journey there's a stopping point for scenic views to look out from. But would you say that you started to feel mastery pretty early on?

Lora Krsulich: Yeah. There were certain skills that I felt more competent at earlier in my career and some that I needed to build. I felt very competent at depositions early on. It felt like a natural fit to me. If you talked to my friends from high school, they'd say, Lora's always been into this one-on-one interrogation thing. It was something that I enjoyed doing. But some of that maybe was false confidence, because the more and more I practiced depositions and reviewed my transcripts and talked to other people who were more senior than me deposing witnesses, you learn there's a lot of room to grow. So yeah, there was some comfort in that skill, but recognizing there's room to grow there too.

Lora Krsulich: And some of the skills that came less readily were something like standing up in court and doing oral argument. For a while, I just didn't understand what the purpose of oral argument was. I understood the court had the briefs. The court could ask questions if they had them. But we've put everything into the briefs that the court needed to know. What's the purpose of oral argument? And I think as a junior lawyer, I would try to memorize the law and have it readily available and kind of run through the law for the court.

Lora Krsulich: The more times I've been able to stand up in court and do oral argument, I realized that I was overcomplicating it. The point of oral argument is to simplify the message. Where a brief is 30 pages, oral argument is, I mean, really, the court has a limited attention span. So you need to pick, it's your opportunity to highlight strengths of your client's case and to simplify it and make it easy for the court to understand. Just make your client's case make sense. And so it did not come easily to me early on. But I've gotten more used to it and I really like it now. I really like being able to stand up in court.

Khurram Naik: Let me make an analogy. So in a brief, maybe you have several arguments and you've organized them in terms of importance and that's clear. But then as you say, there's something about oral argument where you can really simplify and clarify your stronger arguments, and maybe that's your approach. Is there an analog to career? You mentioned, hey, there's something you're strong at, something that wasn't as strong at. One approach would be shoring up the things you aren't as strong at. Another approach would be doubling down on things you're strong at and making for yourself a simple story about who you are. Here's a simple story about who I am and what I'm good at, and that's the thing I'm pursuing. So is that the route that you take professionally, or has it been more multi-pronged?

Lora Krsulich: Yeah, it's been a multi-pronged approach to professional development. So what I've started to do is think through, I don't know if it was on your podcast or another podcast I was listening to, but someone said you have to pay attention to the problems that you work on that energize you. If you're working on a problem that you just feel like, I don't want to do this, and you're struggling with engaging with it, then maybe that's not the type of work that you should be doing. But if you have a problem where when you're working on it you're energized, you like doing it, you like focusing on it, that's where you should focus your attention.

Lora Krsulich: For me, depositions, obviously I really enjoy that process, figuring out how to deal with a difficult witness and get admissions. That's something I could do in my free time. I really like that stuff. And then oral argument, standing up and presenting and simplifying an argument, that also motivates me. So I'm not focused on one thing in particular in terms of the way I advocate, but I've been paying attention to the things that I really enjoy doing. And I'm allowing my career to grow around those things.

Khurram Naik: I don't know if that answered the question, but that's really an answer. I think that explains what I'm doing myself. Before law school, I was the president of my undergrad alumni chapter. And in that, I cared about meeting people. I was pretty new to Chicago. So it was my way of meeting people. It was a small enough group of people, wasn't an overwhelming number. So it was in many ways ideal. I had organized events and I had to learn how to network with professionals, peers, or other alums with varying professional success and seniority. And so that was my first exposure to the concept of networking. I taught myself networking through that.

Khurram Naik: Because of that, when I went to choose law school, I was able to choose a law school where I had a full scholarship in Chicago. And so I said, okay, well, I can do that or the partial scholarship for the very strong state school that we have in Illinois. So I went with the Chicago one because I'd be downtown Chicago, I'd be able to network, this new thing that I'd learned. I was excited about putting that into action. So I networked my way into big law. And then I networked my way from there to my lateral move to my current practice. So this core skill set of networking has been with me for years. And of course, it's the core skill that facilitates my work today as a legal recruiter. I could be getting better and better, and there's so much room for me to be getting better in that. But I think to my surprise, I found I didn't ever expect myself to be a manager, but now I've made a couple recent hires. So now I've found myself to be a manager. And yeah, that is energizing me.

Lora Krsulich: So you've just explained to me why you're making the decisions that you're making, because you didn't really understand it yourself. So why are you pursuing these things instead of doubling down on things that are already strengths?

Khurram Naik: I think because I've got to say 80% of where I'd want to be. And yeah, there's a lot more value I could be getting out of pushing it up to 100% or 90%, and arguably that's a higher ROI activity given how far that skill has gotten me. But we're human beings. We have to be motivated by things. I have found something else that is higher ROI in a different dimension. And I think we can be surprised at what turns out to be high ROI in the long run. You don't know in advance. So I think it is a good idea to round out some of your skills.

Lora Krsulich: Yeah, so again, I think I really like your idea of pursuing what is interesting to you in that phase, because a career is long. And so there's no need to feel like it's some sort of whack-a-mole thing where you just have to master everything all at once. You just pursue something for some period of time and say, okay, what's the next thing.

Lora Krsulich: And I think I put a lot of pressure on myself earlier in my career to be the best litigator and present that way. And then over time, I've been giving myself more grace and realized, like you said, careers are long. A group of us were talking about this case and pointing out that the lead lawyers were all in their mid-60s. And so you think, to get to the peak of your career, it takes some time to build up the comfort, the connections, the facility with the law and where you're arguing. Giving yourself the grace to do that. But recognize that it's going to be a long time. So if you're just constantly hitting your head against the wall, not enjoying what you're doing, that's misery. You don't want to practice that way. You have to think about what you're going to enjoy and then give yourself the grace to get better at it.

Khurram Naik: I want to go back to your approach for getting admissions out of a hostile witness. Can you share some of your trade secrets? What's your approach?

Lora Krsulich: Well, let's see. I think patience is very important, and knowing the documents is very important. And also following, listening and following up on the answers. I'm just throwing things out now. And also watching the witness's body language and whether they want to tell you more from their answer. I found all of that very important. I also think it's really important to be in the room with the witness. This is something that people have been debating more in the post-pandemic period. I do think it's really important to be in the same room.

Lora Krsulich: Khurram may not believe it, but I once had a witness where I was so in tune with them that I knew when they needed to go to the bathroom. We just kind of looked at each other like, okay, can we get a break? We were very in tune. And that witness actually asked me to go out to lunch after the deposition. Just on the same page. I think that ability to read body language, get in the same headspace as them, understand where they're coming from, read all their documents, I think you can be very effective at getting good admissions from that. So that's what I've done. I think it works.

Khurram Naik: I think something else that ties in is, like, hey, there's no reason why you have to wait to acquire skills. Something that you haven't waited on is business development. That's something you've taken seriously. You've originated clientele and work. Tell me about how you came to want that and then how you pursued it.

Lora Krsulich: Yeah, so great. As I got further along in my career, I looked around at the partners that I was working with. And I recognized the confidence that partners had when they were able to develop their own business, their own client relationships. And I knew that I wanted that. I wanted to be the person that a client could call, and I'd be their contact. If they had an issue, they knew they could call me. And I thought I'd be good at it because I'm calm, I'm understanding.

Lora Krsulich: So I knew I wanted to do that. And I'll do an aside. When I was clerking, my co-clerk Abigail Orcutt, her dad is Bill Orcutt, and they were extremely generous. Her dad, who's passed, was extremely generous. He'd have us clerks over, and the way they opened up their house was very moving to me. The way her dad talked about client development was like bringing people in to be part of the family. That always stuck with me, and how important that is. That was my first kind of personal interaction with a big law partner while I was clerking, and to witness what he did and how he handled that with his family was really inspiring to me. I always kept that in mind as something that I wanted to do when I was thinking about client development.

Lora Krsulich: But being a first-generation lawyer, I didn't have people in my family who were lawyers or even people who had the means to hire lawyers to do the type of work that we did. So looking forward in my career, it was a huge question. How was I going to do this? I wanted to do it, but how? I didn't think I had a network that would just organically feed me business.

Lora Krsulich: So I had this great fortune of a friend from college who referred me to her friend Megan Senese at Stage, where she has her own business working with senior associates and junior partners, figuring out how to develop business and how to network. And some of the ideas that have come from my meetings with Megan, I just love them. It makes networking make sense to me. In the way that we talked about doing things that you find joy in and that you like doing, working with Megan has become one of those things.

Lora Krsulich: One of the things we talked about was this idea. I used to go, I mean I still go, to these big bar association events. And you sort of feel like, there are tons of people in the room, how am I going to get to know anyone? But this is how I'm supposed to network, I'm supposed to meet people. With Megan, her idea was, okay, let's set some specific goals around those big events. Maybe it's two or three people I want to get to know well enough at that event to follow up with and network. That's the goal. It's not meeting everyone in the room or passing business cards. It's having a tangible goal when you go there.

Lora Krsulich: And then also, how can we develop our own networking events? You don't have to rely on the bar association to develop your networking events. You can invite people over to your house for dinner. You can organize a prix fixe dinner at a restaurant and coordinate people to come together. Taking ownership of some of that networking. It was like a light bulb. As a first-gen lawyer, this is something that I can do. I can definitely do this. I like going to dinner. I like having people over my house. I like all these things. So once I started to work with her, I recognized that client development was something that I could do even as a junior lawyer. And I like doing it. So I've been doing it more regularly.

Khurram Naik: Yeah. And I have to thank you again on the topic of high trust. I have to thank Megan because she's the one who introduced us. She was high trust in that she had identified me based on my LinkedIn posts. We didn't know each other at all. And then you in turn trusted her and trusted me when we connected. So it was just a really nice experience of this virtuous cycle of trust that we all experienced.

Khurram Naik: Was there any relationship between the things you learned from Megan or generally in business development that have impacted how you practice?

Lora Krsulich: Yes. So there's this concept of taking ownership. Taking ownership and being proactive. That has been very important for how I practice. Take something like client development. I had always thought that client development meant a partner taking an interest in you and introducing you to their clients, and you building a relationship with them through that. And then when that partner leaves the practice, you would take on that relationship. That's what client development meant to me. And it didn't feel like I had a lot of control over that process at the time. The partner had to see something in you through something that you've done. The client had to like you, but maybe they just had to like you for who you were. You didn't have to do anything.

Lora Krsulich: Working with Megan, I've realized there's a whole lot more that you can do if that's the path you choose to make that successful. You could be the one that is reaching out to the partner and reminding them of the things that you've done or the things that you want to do. Telling them, hey, I'm thinking about this particular contact, do you have any ideas for how to connect with them? You being the one that's putting that on your plate to reach out. And apart from that, just not relying exclusively on someone to take an interest in you. Starting to develop your own network and personal contacts, posting on LinkedIn, becoming a person who talks about the issues that you care about. All of that is within your ownership, your ability to do that.

Lora Krsulich: And I think that's so important. Things don't happen to you. You can take them on yourself. I've learned that through the process of iterating with Megan and figuring out what's going to work for me. And applying that to litigation, you can think the judge knows the law. In patent law, they know patent infringement law, they know the way it works. But the way you present it, the aspects of the law that you highlight, can influence that person. So what can you do to influence the way that the judge thinks? Taking back some of that ownership. Advocating in every way that you can. Working with Megan has allowed me to realize how much ownership I have over the trajectory of various aspects of my career.

Khurram Naik: And then tell me about what led you to Goodwin. I mean, you were growing and progressing at Susman, getting this great trial experience. What even had you considering making a change, and then how did you land on Goodwin and patent litigation?

Lora Krsulich: Yeah. So the person I talked to you about earlier who kind of introduced me to Susman told me at the time, think about your career in three-year chunks. Think about what you want to get from your career in those three-year chunks. When you're thinking about different career choices, think about them in that way. Which choice will best position me after this period of time? Three years is an arbitrary number, but think about it in a chunk.

Lora Krsulich: When I had my second son, Bennett, I committed to myself that I was going to start that process of thinking through the next stage of my career. I had been at Susman for about four years at that point. I was in my fifth year. And I committed myself to thinking through, okay, I want to make partner, and I want to litigate. Where will I do that, that will make me the most effective, that will let me grow?

Lora Krsulich: So I did a lot of that conversation in the year. Bennett was born January 1st, so I kind of let that be my motivation. And then I did a lot of thinking with friends and colleagues and partners and different people. I don't think we started working together until like November at the end of that year. So it had taken some time.

Lora Krsulich: There were things that I wanted to look for from the next part of my career that were really important. One was this idea of being a partner to business. Having, being a lawyer that understands the way that business works, that can help a business from various aspects. This idea of partnership and getting to know the people at the client that you're working for was really important to me. The second thing I was looking for was collaboration within the organization. Multi-faceted teams, teams of science advisors, people at various parts of their career, and this emphasis on collaboration and mentorship. I thought that would help me grow as a lawyer from where I was and into a long career. And then the IP focus. I'd always been very interested in science and technology. Having done a couple of IP cases at Susman, it was something that I wanted to do a deep dive in and focus on. Because it was interesting, and I also recognized that if you become really skilled at the law, you can go far with that in terms of client development. I saw my expertise as being someone who could translate technical terms into simpler concepts. And that process lent itself well to IP litigation where you often have to translate technical concepts in a patent to a jury.

Lora Krsulich: Those are the types of things that I was looking for, and I was sort of open to that when we started working together. Through that process, you introduced me to different firms and helped me think through the strengths of some of the firms, the people that I was hoping to connect with in the different departments and units. And Goodwin was just a great fit for those things that I was looking for.

Lora Krsulich: Having such a large business law department that takes companies from their early stages all the way through IPOs and all the growth, and that collaboration between business law and litigation was something I was like, oh, this could be a really nice fit. Because I could see myself as a counselor, as someone helping long-term clients. The collaboration is a focus at Goodwin on cross-unit collaboration and mentorship and promoting professional growth. There are tons of workshops and trainings as you come along. I've at least done a public speaking workshop and then this transition to leadership workshop. So I can see huge benefits from that in my career, growing and growing.

Lora Krsulich: And then the IP focus. The IP litigation unit at Goodwin is just very tight-knit. We do a lot of different cases, trademark, patent, copyright. I remember talking to Neil and Brad about wanting to develop a litigation unit that has a lot of people who are focused on science, but also has these general litigators who can go in between. The fact that you have this mix in this business unit has been really nice for me. So it just worked out. It was a great fit. It was very difficult to make that decision, having felt at home at Susman and loving the people there and loving my colleagues there. But I did take the leap and I'm really happy.

Khurram Naik: It seems to me that part of your story is inverting things that on their face really seemed like weaknesses into strengths. The fact that you're first-gen, then, okay, heavy community bent, then you said, well, I want to create that. So then with business development, same thing. I don't have somebody who's just going to hand off business. Whether or not this concept is a fiction that someone's going to hand out business, there are some who do come with relationships or are embedded in some sort of social ecosystem that's going to facilitate that. And then also this point about not having a technical background. Any number of other patent practices would just say from the outset, we don't want anyone who doesn't have a technical background. But you have inverted that into a strength to say, hey, the fact that I don't have a technical background means I'm not going to get hung up in the minutia and the details. I can see the big picture and simplify the story. So it seems that this has been a recurring theme throughout your career, inverting weaknesses into strengths. I don't know if that resonates for you.

Lora Krsulich: I think yeah, I guess so. But the other thing is you see a problem. I see a problem in IP litigation for jury trials in particular. Maybe you need technical litigators if you're at the PTO and you have patent examiners and you're talking to them. They have science backgrounds and they're steeped in the science. But if you are talking to a jury of 12 people who are randomly selected, who have no background in patent litigation or the specific science that you're talking about, you need people who also are new to the science and have a fresh perspective to translate that over. So I guess it's an opportunity.

Lora Krsulich: And I listened to a podcast where someone said to me, you're highly strategic. And I took offense to that. I was like, what does that mean? I'm not calculating. I'm not Machiavellian. And that's the way I had interpreted that word. And she's like, absolutely not. You have to own that word. You have to take that word back. Being strategic just means being thoughtful and thinking through what your skills are and how they match up to what you want to do.

Lora Krsulich: And so I would absolutely say that I've done that work. I've thought about going back to what I enjoyed doing as a kid and what I value for my own work. Thinking through those skills and matching them to the type of work that I want to do. I want to do, and I've narrowed it and narrowed it as we go. Being an IP litigator who focuses on jury trials is a strategic decision that I've made based on an evaluation of my personality and my particular skill set. I could have done any number of things, and this is where I've landed because I thought through it. And maybe later in my career, I'll think about something different. But I think this is a great match for where I am right now.

Khurram Naik: What about ambition? Being ambitious.

Lora Krsulich: Yes. You know what comes to mind is this idea of being a gunner in school, in law school, and you never want to be the gunner. So it's like, oh God, am I going to just admit to being a gunner? But you have to be ambitious to stay this long in big law. You have to want something more for your career. You have to have a vision. And so yeah, I do think I'm ambitious.

Khurram Naik: What do you see for yourself in the next six months? What are you excited about?

Lora Krsulich: I'm very excited about continuing to build relationships with other lawyers at Goodwin in the IP litigation unit and in our business law department. It's very important for me to feel at home someplace, to continue to build those relationships. So that's where I'm focused. And then more and more training, more and more exposure to jury trials. I'm looking for any cases that are going to trial. I've been thinking about how to take advantage of my proximity now being downtown to the district court. Thinking about spending some time there, continuing to network with Judge Gutierrez who's now moved to JAMS and picking his brain about different things. And I'm also going to take a NITA training, the national trial advocacy training, in February to continue to develop my trial skills. So I'm excited about all those things.

Khurram Naik: That's a great mix. Lora, I'm glad that we sat down to talk and share your story, because I think it's so inspirational for so many, first-gen or otherwise. I really admire the way that you approach practice. You are extremely hardworking and down-to-earth. But then also you do have this strategy and ambition as well. So it's an amazing cocktail. I'm really excited to see what your future looks like in the coming years.

Lora Krsulich: Thank you so much, Khurram. You said you were putting your bet on me, and I just want to make you proud. So thanks so much for taking the time to sit with me and interview me. I've really enjoyed it. And I regret that our time was up, but I'm glad we did it too.

In this conversation, we dig into the relationship between gut instinct and formal analysis in legal decision-making, why a weakness early in your career can become a strength if the right people push you, how to find your own voice when none of the senior mentors in the room look like you, and what it actually looks like to take a risk and bet on yourself twice in a decade.

Keep reading below for the full episode and the complete transcript of our conversation.

Top Insights

Below are the highlights of our conversation:

• Playing Lawyer vs. Being a Lawyer: Sonal's early deposition struggles came from trying to mimic senior lawyers she admired rather than listening to the witness. The breakthrough was realizing she was playing lawyer instead of being one. Once she trusted her own judgment about what the follow-up should be, depositions became one of her favorite parts of the job.
• Gut + Process, Not Gut vs. Process: Sonal believes strong legal instincts already contain a pro-con analysis underneath. The formal framework, listing options, weighing secondary and tertiary consequences, ranking against end-goal priorities, is often a way to express what the gut is already doing. The job is not to suppress instinct but to understand what it is telling you.
• Bet on Yourself When Things Are Going Great: Sonal's two biggest career moves, leaving WilmerHale for Durie Tangri and later returning to WilmerHale, both happened when nothing was wrong and everything was working. Each move required an internal push to see what she could do with a different set of resources and without the safety of the team she had grown up with.
• Find Your Voice Without the "Hey, Buddy": With no senior women to watch as role models early on, Sonal had to invent her own way to build rapport with opposing counsel. The senior partners around her started calls with "hey, buddy, you catch the game last night" and that was never going to work for her. She had to figure out a version of rapport that was hers, and she did.
• Grab Mentorship From Anywhere, Including Opposing Counsel: Twice in Sonal's career, senior opposing counsel reached out after hard-fought matters to offer career mentorship. Her advice to younger lawyers: do not draw a narrow line around who you think your mentors should be. If someone invests in your success, take it.

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Full Transcript

Khurram Naik: Sonal, I'm so glad that we are having this conversation. I know you're skeptical that you had an interesting story to begin this episode with, but I'm excited to jump in with this story of your first deposition.

Sonal Mehta: I'm not sure it's that interesting, but it was pretty mortifying. I was a young associate. I was taking a deposition of a witness who we weren't sure what he knew about a particular topic. So we needed to take his deposition just to figure that out. I go into this deposition, and the guy was so mad that he was being deposed. I think what particularly angered him was that this kid was taking his deposition. So I show up, I take the deposition, he's super hostile. Turns out he doesn't know anything. So fine, it's a very short deposition. I report to all the people on my team that it was a short deposition and a non-event, and the guy was kind of a jerk to me.

Sonal Mehta: Then later one of the more senior lawyers was reading the transcript. He came to me and said, so I know it was your first deposition, but when you asked those questions at the beginning, does the witness understand that they're under oath and are they able to testify truthfully and accurately, and is there anything that would preclude them from testifying truthfully and accurately, you can't just say all of those things and then move on to your questions. You have to stop and ask a question, and then have the witness answer before you move to the next point. I was so mortified, because it turned out I'd taken this deposition that ultimately ended up being a total waste of time, but I couldn't even get the five questions at the beginning that came out of the deposition textbook correct. I totally screwed that part up. That was quite the experience, and I now actually know how to ask those questions. Everyone knows that I know how to confirm at the beginning that the witness knows they need to testify truthfully and accurately. The deposition can get through those questions before I start my depositions.

Khurram Naik: How did your second deposition go?

Sonal Mehta: That part went better. I will say that part went better. We could talk about this more, but I at the beginning of my career definitely struggled with depositions. There was a deposition not long after that, probably a few months after, that I took and a partner was with me. Afterwards, he said to me, you know, you're so good at everything else in this job, it's really strange that you're so bad at taking depositions. So that was a really affirming moment for me in my early practice as an associate, that I was so bad at taking depositions that I was getting that comment back. It did turn around, and I would like to think now that I'm actually much, much better at it. It's actually one of my favorite parts of this job. It just goes to show that you could be good at some things and be really bad at others.

Khurram Naik: What do you attribute early on to the challenges around depositions for yourself?

Sonal Mehta: I actually spent a lot of time trying to figure this out. I realized I was trying too much to emulate other questioners. I had examples of people I thought were really great deposition takers, and I would go in and try to do the deposition the way I thought they would do the deposition. I would get in my head about it, and it would be awkward for me. I wasn't really connecting with the witness or being able to read the witness properly. I was more focused on, okay, now how would this person ask the next question? It ended up just becoming this weird vortex of me trying to figure out, predictively, what someone else would do in response to answer, instead of listening to the answer and then thinking about, as the human sitting across the table from the witness, what's the appropriate follow-up, or what's the admission I want to try to get. If I go back now and think about what I was doing, I was playing lawyer as opposed to being a lawyer. Once I got out of that, it got a lot easier and a lot better.

Khurram Naik: How did you make that transition?

Sonal Mehta: I wish I had some trick for how I did it. Candidly, I had just weird rhythms in my cases, where there was a period of a year where I had no depositions at all. Then I went and took another deposition, and it was completely different. Some switch had been flipped. I suddenly felt like I knew what I was doing, and I could do it. I remember the deposition. I remember where I was. I was like, oh, I can do this. I know how to do this. This is great. Maybe it was the year in between that had me distancing myself from trying to mirror people, that somehow made it better. Then suddenly I was comfortable and I could do it, and from then on it's been great.

Khurram Naik: You're still taking depositions today, right?

Sonal Mehta: Yes. I mean, I try very hard to give the younger lawyers on my team as many opportunities as I can. But I love taking depositions. I don't think I'll ever give it up.

Khurram Naik: Do you have a preference between fact and expert depositions?

Sonal Mehta: My favorite are expert depositions. If I could just take expert depositions every day for the rest of my career, I would be so happy. Unfortunately, there are other parts of litigation you also have to do to get there. But that would be my absolute favorite. I enjoy taking damages expert depositions. I also really love taking technical expert depositions. I've recently done a bunch of economist expert depositions, absolutely love taking expert depositions. Fact depositions are great too, don't get me wrong, but the material you have to work with with an expert makes it especially fun.

Khurram Naik: Describe at a high level, what's your philosophy around expert depositions? What's the strategy in terms of how much time you're taking, what other kinds of admissions or work you're getting, how you're thinking backwards from trial strategy?

Sonal Mehta: It's a little bit of knowing what I need for either cross-examination at trial or for dispositive motions. Often there's a substantial amount of overlap between the set of admissions you want for those two things. What I'm really thinking about when I go into a deposition, especially an expert deposition, is what are the admissions I want in sound-bite form that I could block quote in the introduction to my summary judgment motion to establish that their expert has conceded something that means my client wins. That's the frame I want to think about an expert deposition in. Once you do that, you're also getting the material you need for the cross at trial. I also want to have modules that are more jury-focused in terms of the cross we might do of the expert at trial.

Sonal Mehta: I'm usually not wedded to an outline. I'll have the expert reports in front of me. I'll have some form of an outline with the different topics I want to cover. But I'm a much more instinctual depo-taker. I start on a topic and then I see where the expert goes, and then I'm going to follow that. Often it's about creating tensions or inconsistencies in the expert's opinions with other things that are happening in the case, with the record. Often it's about forcing them to take a really extreme form of the position. Okay, well, if that's your opinion, then this must be true, and then this other thing must be true, and if those things are true, then really what you're saying is this crazy thing that no judge and no jury would ever believe, which means everything else falls apart. A lot of it, to me, is listening and then the follow-up, much more than what's on the piece of paper. There have been expert depos where I've had an outline but I actually haven't really even spent much time with it at all. I really just looked at the report and the back and forth, and followed what the expert said to its logical conclusion to get the admissions I want.

Khurram Naik: Do you have an approach for different categories of experts? I think about two kinds of experts. One is the highly credentialed big-ego expert, and there's definitely ways they can trip up. Then there's also the very sophisticated, has-been-deposed-multiple-times expert who is very good at not saying anything. Maybe there are other categories as well. Can you share the kinds of experts you work with and techniques you use?

Sonal Mehta: Those are two good categories, and a lot of experts fall into both. The other one, which in some ways is more challenging, is the first-time or relatively new-comer expert, where they're being called upon because they might truly be experts in that field but aren't litigation pros, don't really understand the process. All of those categories have different challenges and I would take different approaches for all of them. With the newbie expert, someone that's really steeped in a field that hasn't been in litigation before, one of the challenges is they don't understand the litigation process. While there's some advantages to the taking attorney from that, one of the disadvantages is they're often really reticent to answer questions. It's like they're kind of paralyzed by the fact that they don't totally understand the process, and they're afraid that something they say is going to be a problem. You sort of have to break them out of that and get them to start actually engaging and feel comfortable enough that they're not worried every question is a trap. Maybe it is, maybe it's not, but they're not worried about that. They're starting to feel comfortable they can actually just answer your questions.

Sonal Mehta: With the big-ego experts, and with those guys or gals, but often guys, every question is going to have a different approach. My approach is, look, maybe it would be effective to feed the ego, but I have a really hard time doing that just in general in life. I don't have a lot of patience for people with big egos. So I don't really feed the ego, but I try to neutralize it. I'm not going to go in and start challenging this person's credentials or opinions and get them all defensive and get the ego all worked up. Instead, it's going to be more about, what are the things we can all agree on, maybe let's start there. Maybe it's about making that person feel like, oh, she doesn't really know what she's doing, she's asking me softball questions, maybe kind of soften the ground, get to some points of agreement, some points of consensus, and then start to build from there on what's the logical next step down the line. If you agree with this, then you'd have to agree with me that the other thing, and then you'd agree that the other thing, and you sort of let it go that way. If they're not feeling super challenged and you can get them to agree to that, the good thing about a witness who has a big ego is that they're also really worried about their credibility. When they feel like their credibility is on the line, they will concede, because they can't possibly be in a situation where another whoever they view to be their peers thinks they're not being credible.

Sonal Mehta: I suspect my style is actually not that different across these different modes of experts. I'm sure there's some degree of phrasing a question and friendliness and warmth that probably changes a little bit. I've heard stories about lawyers that go in and they're playing like, oh, I don't know what you're talking about, teach me everything. I just can't put on a fake personality. I just kind of have to do my thing with more tweaks around the edges of my questioning style than totally different questioning styles.

Khurram Naik: You used the word intuitive for how you approach it. Is there something about time that you're tracking? Benchmarks for what stage you want to be at at different hours?

Sonal Mehta: It really depends on how much material I have to cover and how much I feel like I'm going to be compressed for time. Usually I don't feel super jammed for time in depositions. I think I'm a pretty efficient questioner, and I'm pretty good at gauging relatively early in the deposition how much the person is just going to talk to fill the time. If I know there's a witness that is going to filibuster, that their whole strategy is the middle category you mentioned earlier, where they've done it enough to know they can dance around the question and not answer, if I know I'm going to be dealing with that type of witness, I will sometimes go in and say, okay, here are the four topics I'm going to cover, and I need to be through these three by X time, because I need an hour and a half for the last topic. I also usually will go in, when I know there's going to be time constraints, with a rank ordering of priorities of the different topics I'm going to cover. Then if I feel like time's getting tight or the witness is just rambling and eating time, there'll be things I'll skip because I know it'll just be a time sink and I don't need them.

Khurram Naik: When it comes to dealing with opposing counsel, I think of two categories of challenging behavior. One is lawyers with a strong reference to coaching the witness. Another is lawyers that are very hostile, making the expert feel this is a very adversarial proceeding. It is the adversarial process, but feeling like there's something to be gained from overtly being hostile. How do you deal with those?

Sonal Mehta: In some ways those issues are actually worse with fact witnesses than with experts, because most of the experts we all deal with have done it enough that they don't need the lawyer to be super involved in the drafting and really guiding the deposition, the defending lawyer. I feel like in my experience, the lawyers tend to be a little less involved in the deposition when it's an expert deposition. Regardless, whether it's expert or fact deposition, yeah, it's really unfortunate, but there are lawyers where you feel like it's clear that statement was made with a direct intent to suggest to the witness what they should be saying.

Sonal Mehta: Courts these days I think have done a really good job setting out, through local rules, through judge standing orders, through local practice and expectation, some real strong incentives for lawyers not to do the coaching and not to do the obstruction during deposition. So that helps a lot. Pointing out that if that behavior continues, it might get taken up with the judge and the judge is not going to have a lot of tolerance for that kind of behavior, usually ends up working. But my thing is I'm not going to make a big deal out of it and yell back. I probably will let it go the first time or two, especially if it's a younger lawyer who maybe is just trying to get their sea legs and figure out how depositions go. But if it's someone really senior, or it's happening over and over again, you just have to politely call it out. I've literally said in a deposition, quote, cut it out, you know what you're doing, you know what you're doing is wrong, stop it, end quote. And it didn't happen again. There was no more coaching, there was no more commentary and colloquy between the questions and the answers. That statement was made, the person actually looked a little embarrassed, and it went quite smoothly after that. There's an element of just calling it out, and when it's called out, sometimes people realize they need to stop.

Khurram Naik: What's one of the most surprising moments you've had in deposition?

Sonal Mehta: I don't know that it's one, but I've got to tell you, I have had some experts that have just given up the farm in ways that, you have to ask, were you prepped? Did you write the report in this case? How is it possible that that's the answer to the question? The only implication of that answer is that your client's case literally cannot stand any longer. I've had that with technical experts in IP cases where the technical expert has admitted something that would, maybe not in exactly those words, mean non-infringement, but basically in response to a hypothetical, where it was like, okay, well, assume X, Y, and Z, would the answer be yes or would the answer be no? And they got it wrong and they said no, which meant my client wins. Then we took that admission and we went to the judge and we won summary judgment. It's a little surprising actually when someone that's spent so much time on the case, worked on a report, presumably went through the report multiple times with their lawyers to prepare for the deposition, just gives you the absolute wrong answer from their client's perspective. I find it surprising. Now I find it awesome, and those are really, really good days, and I have some really fond memories of those days. But I still can't believe it when it happens.

Khurram Naik: What's so interesting is you went from deposition being one of those challenging things to one of your strengths. Do you feel like that's often the case for people? For myself, I would say things like being oriented to growing a network or being in a sales capacity or even writing, these are things that historically I didn't perceive to be strengths of mine, but in pursuing them I worked on them and found my own ways to practice them, and now I perceive them to be strengths. Do you think that's much more common than we realize, that the things that lead someone's career become their strengths as something that started as a weakness?

Sonal Mehta: I hadn't actually thought about it that way until you just phrased the question that way. But as you were going through those examples, I was going through my own examples of things that I struggled with or parts of this job I struggled with and that now I think maybe are among my strengths. I think you're right, it is true for some people that those areas of weakness end up actually being the areas in which they're stronger, because they put in the time to improve on them. If it's pointed out to you that it's an area of weakness, or you realize it's an area of weakness, it becomes something you're then thinking about and you're conscious of, and you're trying to improve.

Sonal Mehta: I also think there are some people where those are some areas in which, for them, it might be a weakness, but you don't have an incentive to try to improve it, or you don't want to improve it, or you think you can't because it's not consistent with your personality. So it's a little bit of a wishy-washy answer, but I do think you're right. Another area for me that was such a challenge, and I still hate it to be fair, I hate it, but I think I'm getting better at it, is network building and business development. It was awful. I hated it. I never thought I'd be able to do it. I never thought I'd be able to have any clients because I never thought I'd be able to meet any clients, because I just found the whole thing to be, there was this mystique around business development. When people talked to me about how they did it, I thought it was all super awkward social interactions that I would never want to have. Now I think I'm fine. I don't love it and I'm not great at it, but I know enough people that I can keep myself occupied and out of trouble. I had to spend a lot of time working on it, and people had to kind of push me actually, in some ways maybe more than I had to spend time working on it. People that were my mentors, people I was working with, had to push me to do it really kind of aggressively, because I was really resisting it. Thankfully they pushed me to work on it as a young lawyer, and it got better. There's an element of both the self-internal motivation and drive to improve areas of weakness, and then there's the element of people pushing you to improve. For me, I have a bit of that self-drive, but I also have been lucky to have people at every stage of my career pushing me to improve.

Sonal's experience of finding her voice as an early-career lawyer without any senior women to model resonates with what Lora Krsulich shared in her episode about coming up at Susman Godfrey as a first-gen lawyer, and how she found her own confidence to take up space. Listen to my episode with Lora Krsulich.

Khurram Naik: It's remarkable to hear someone as accomplished as you say you're having a challenge around something that would be perceived as a core function. You're a partner, that's a core function. You're also on the management committee of WilmerHale, which is a very well-regarded firm. Can you share what's working for you, how you're thinking about progressing through this and making it more tractable?

Sonal Mehta: It's been a journey, to use the cliche. When I was a senior associate and a young partner, I was given some coaching. I made partner while I was at WilmerHale, and they identified for new partners these business development mentors. They were senior partners very successful at the firm, usually in different practice areas and in my case even a different office, whose relationship was to mentor me in business development. I'm so thankful. He made me write up a business plan as a first-year partner, and I hated every minute of it. I hated the process of making the plan. I hated everything I thought I might have to do to execute on the plan. I would write down things I was going to do, and as I was writing them down, I'd be like, I can't believe that I would ever have to do this, this is going to be so awkward with people. So it really went from being forced, thankfully, to think about it and plan for it and confront that I hated it.

Sonal Mehta: The way my thinking has evolved is realizing that actually, even though I went through that whole process, that wasn't going to work for me. Having a formal business development plan, here are the people I'm going to check in with every month, here are the articles I'm going to write, I'm going to go speak on X number of panels, I'm going to go to Y conference and go to this cocktail party, that kind of formality was never going to work for me, because after writing it all down I just wasn't doing any of it. The journey has been realizing that, at least for me, what works, to the extent it works, is actually getting to know people that I like. It's amazing how many of the opportunities I've had, and the really great connections and great work, have been ones where there was no intentionality behind it at all. It was just somebody I struck up a conversation with, or somebody that asked me for a favor and I did them a favor and I never thought I'd hear from them again, and then lo and behold, something happened. It sounds oversimplified and maybe a little bit naive, but just putting good things out into the world and coupling that with doing good work has been really successful for me, to the extent anyone would say I have success in that area. It's also just a lot easier for me than doing anything formal. A lot of the people I work with as clients are people I was an associate with. That's the other thing I think people don't realize when they're growing up in the law, for those of you that are a little more junior in your career, the person down the hall that's your peer today, they will get more senior in this business as will you, even if they're not at the firm anymore. Those people end up wanting to work with you in the future when they become clients. I teach a class at Berkeley, and a number of my clients are former students from the class, who then years later went in-house and had a problem and called me. For me that's just been much more successful than any kind of networking plan I could then go execute on.

Khurram Naik: I want to go back to you talking about when you were early in your deposition journey and noticing, oh, I'm really trying to respond like this other lawyer I admire or had learned from. The way I'd phrase that is finding your voice. Were you able to find your voice elsewhere at that time, or is that just part and parcel of generally finding your voice? Can you talk about that process?

Sonal Mehta: I actually think that was maybe the most acute example of the overall process of finding my voice, because I definitely had that in other places too. I think every lawyer goes through this. For me, it was especially difficult because I did not have many women, really any women mentors, or senior women to look up to as I was growing up as a young lawyer. I had tremendously talented, off-the-charts talented mentors and senior lawyers to look up to, don't get me wrong, but they were all men. My examples of very basic things, like how do you start a meet-and-confer call with opposing counsel and build that rapport, they were all men.

Sonal Mehta: I often give this example to younger lawyers, but probably one of the biggest struggles I had was figuring out how to build a rapport with opposing counsel that's organic and genuine, when the examples I would sometimes see would be like the senior partner getting on the phone with opposing counsel and the start of a call being, hey, buddy, you catch the game last night. You know, the hey, buddy, you catch the game last night, I can't start a meet-and-confer call that way. First of all, I don't know what the game was. I definitely didn't catch it. Everybody knows that. There's nobody that would think that I caught the game last night. It'd be a miracle if I knew what sport we were in in terms of the season. So that was a big struggle for me, how do I do that thing, which is really important, developing a relationship and a rapport with opposing counsel is critical to being able to serve your client's needs, how do I do that if I don't have the hey, buddy? I just kind of had to figure it out. There are people that are better at that now than me. There are definitely people that have more of an ability to connect on that kind of thing than I do, but I've figured it out well enough that I can do it, and it serves my clients' needs. That's true for courtroom advocacy, it's true for depositions, it's true for business development interactions, it's true for when I go and pitch a case, it's true for when I'm interacting with opposing counsel. In every aspect of this job, I think there was a learning curve for me to find my voice.

Khurram Naik: Can you speak to the learning itself as far as legal decision-making judgment analysis? How did you come into your own voice there? It's easy to say, how would you think about this case? But there's a lot to be said for how you approach your own case. This is something I just covered with Silpa Maruri, and that was something that was a hallmark of her early on, following her own instincts. I'm curious where your thoughts are on how you found your voice in legal judgment.

Sonal Mehta: Okay, so now this is going to sound arrogant. I don't mean it to be arrogant, but that's actually not somewhere I felt like I struggled as much. Even from when I was a very young lawyer, rightly or wrongly, for better or for worse, I always had a pretty high degree of confidence in my judgment about things. I almost always had a pretty strong, early instinctive reaction to what the right thing was. Of course, I would need the factual and the legal inputs to that. I needed to understand what the legal frame is that we're looking at, I needed to understand what the facts on the ground were. But what we should do after we know what the facts are and what the law is, and we've laid out the different options, here's the, should we do A, B, or C, which of those things we should do and the why and how we should execute on them, rightly or wrongly, and probably a lot of instances naively, I always just had a gut of, okay, I thought about A, I thought about B, I thought about C, I can see the pros and cons, we should do B, here's why we should do B, and here's how we should execute on B. That was a place where I needed to find the skills to do the execution, I needed to gain the credibility to convince people I was right, but I didn't struggle with figuring out what I thought the answer should be.

Khurram Naik: Let's take someone who has the inverse problem. Early in their career they were told, hey, you're really great at deposition, but you have a challenge around exercising your own judgment, around confidence in your own decision making, around applying frameworks. How would you counsel that lawyer?

Sonal Mehta: This is hard for me, because for me it is more instinctive. But what I would counsel them to do is essentially what I said my gut does for me, which is, the baseline for all of this, of course, is knowing the law and knowing the facts. Once you have that, I would counsel them to think about what are the options, what's the menu of options, what are the pros and cons of the menu of options. There I think you have to think expansively. There are obvious pros and cons in any decision, but there are often secondary or tertiary pros and cons that are less obvious, that require some effort and some experience to really think through. I would encourage people to think about first-order pros and cons, but also secondary and tertiary order pros and cons.

Sonal Mehta: Then it gets hard. Okay, so now I looked at all the pros and cons, how do I make a decision? For me, it would be priorities in terms of end goal, because those priorities are going to let you weigh the pros and cons. If you have a bunch of pros and a bunch of cons, and you're like, there's a lot of pros and a lot of cons here, how do I make a decision? One of those, either in the pro column or the con column, is going to go to whatever the most important goal is of a particular project or a particular matter or a particular business. You're making a judgment based on, I have to do something here, even when I don't have perfect knowledge. Let me go with something that, based on what I think the priorities are, is going to help me optimize to the outcome that I want.

Sonal Mehta: The other thing I would tell people that are struggling with that is, you're not always going to get it right. If you are paralyzed by the desire or the need to know with certainty that the decision you're making is going to work out the way you think it's going to work out, you've got to just get over that. We make decisions in law, but in life, you can only make the best decision you can at the time you have to make it with the best information available to you at that time. That's all we could ever ask for from anyone. You don't always have all the information. Circumstances might change. But you've got to just make the decision, and then you've got to be able to live with the consequences, and trust that you're doing the best you can now, and that your future self will be in a good position to deal with whatever the consequences are. Hopefully it all works out exactly how you wanted. But if not, you have to trust that you'll be there to deal with the consequences, and your future self will exercise its judgment to optimize at that moment in time.

Khurram Naik: That's a jumping-off point to explore another moment in your career. I'm going to flag back that you're saying, you don't always know if you're going to get it right. You've got a certain set of facts before you, the world is uncertain, you may not have all the relevant facts, the world will change, but you just have to move forward and you have to apply your judgment based on pattern insights to move forward and make decisions in the face of uncertainty. I think that's a very powerful concept, because in my role as a legal recruiter, I see this routinely with lawyers, big law lawyers who are so used to what's largely driven by the billable hour, so used to mining for more and more facts, more and more analysis as the solution, as a legal advisor. How did you apply that concept to your career change, when you were moving from WilmerHale to Durie Tangri? Did you apply that decision-making tool to make that change?

Sonal Mehta: Yes, I did. But again, in the way that I make decisions, which I think part of it was my gut, too. I would say that decision, still to this day, it's been almost 10 years now, is the single hardest decision I've ever made in my career and maybe in my life, honestly. It was an agonizing decision. It took me a really long time to even be open to thinking about it. Then it took me a really long time once I was open to thinking about it to make up my mind. Then there was a period after I made up my mind where I didn't think I'd made up my mind, and I was agonizing over whether that was really the right decision. It was a long process. There were a lot of sleepless nights over that.

Sonal Mehta: The decision-making process that I went through was funnily enough formal. It was a more formal decision-making process than what we've been talking about. It was along the lines of what I just talked to you about, pros and cons and evaluating them and thinking about the importance. I actually wrote it down, and I had a spreadsheet. This is so not-Sonal, the most non-Sonal way to make a decision, to have a matrix of all the factors and the pros and cons, and I weighted it and everything. When I said it was sort of funny you asked that, I had this super formal process. But honestly, if you put me back in the headspace I was in at the time, everything about the process was really ultimately being driven by my gut. What I mean by that is, I had all these factors, and it was this agonizing decision, and at the end, the way I weighted them and the way I came to the decision was really based more on instinct than anything else. That really just goes to the point we were talking about earlier, which is, my instinct in some ways just inherently does the pro-con analysis I'm talking about. Or maybe the pro-con analysis is a way to manifest what's happening when I make a gut decision. I think that's probably true for everyone. Maybe when we talk about people that are more instinctive and people that are less instinctive, it's really less about, is it a different decision-making process, and more about how much you trust your instinct in an express way. I know that I can trust my gut, versus people that feel like they want to go to the more formal process, and so they're not calling it instinctive, they're saying that they're going through a process. In a lot of cases, it reduces to the same thing. Anyway, that was my process. It was an agonizing, awful process, worst year of my life, and hardest decision I've ever made, and then I ended up going with my gut.

Khurram Naik: What even prompted this decision? You started out at WilmerHale, you made partner there, so things clearly were going well. What even got you thinking about making a change?

Sonal Mehta: Like I said, it actually was a process to even get me to be open to the idea of leaving. I loved my time at WilmerHale. I genuinely had the best experience. Could not have asked for a better place to grow up as a young lawyer. Felt like I got such amazing experience and opportunity and mentorship and training from the best in the business. The people that were there at the time that I was working with are just so incredible, and I'm so grateful for the time I had there. I honestly thought I would be there my whole career. I wasn't thinking about leaving.

Sonal Mehta: What got me thinking about it, or got me to be open to the idea, was the Durie Tangri opportunity came up. It was a new thing for them too. I was the first lateral partner ultimately that they had, and they hadn't really ever thought they would do that, because they formed as a boutique of people that knew each other professionally but also were really close friends. So it was, in some ways, kind of like a family firm. They were all so close and they'd all worked together for so long. They were thinking about whether it might make sense to bring someone else on. When that opportunity presented itself, it was the kind of thing that never had occurred to me would be something I could do, because they had never had a lateral partner before. Suddenly there was a conversation, and I was like, oh, I guess I should think about this, because I never would have thought about this before.

Sonal Mehta: I think it was a combination of, sometimes I need a push. This push actually came from myself, not from other people, but it was an internal push to bet on myself and do something that was not the safe, obvious thing to do. Things were going great at WilmerHale. I loved it there. I'd worked with the same people for 12 and a half years. I loved those people, I still love those people, they're still friends. I still respect them as lawyers and as people and consider them close friends. So it was such the safe, easy thing to do to stay. But I felt like I needed the internal push of, okay, maybe you need to try to go do something a little bit different and take a little bit of a risk here, even though things were going great. To have that independence, to see how I could operate as a lawyer without the same set of people I'd been working with for 12 and a half years, without the comfort of knowing exactly who was going to be on my teams and who the clients were. That push to bet on myself and see what might happen if I went out and did something different ultimately was the instinct that drove the decision.

Khurram Naik: When you say bet on yourself, what was the potential upside and what was the risk?

Sonal Mehta: At WilmerHale, I was a very young partner. I had a few of my own matters, matters where the clients were primarily coming to me, but not a lot. I didn't have a huge set of matters and a huge track record as a first-chair lawyer. I had done a trial as co-lead with someone, and I had a few small cases where I was first chair, but it was all sort of new. The potential upside was, I would be able to go and be the lead lawyer. I don't mean that in a your-name-at-the-top-of-the-caption kind of a way. For me, it was more about, it's my strategy and my judgment that is going to guide the outcome in this case. That was really appealing to me, to be able to think about, how do I see this case, how do I see us winning this case, trusting my gut on that, and being in a position to steer the outcome of the case. That was the potential upside. I could maybe do more of that if I was at a place where I wasn't with the same people I'd been working with forever, and where there were new clients too, where the clients didn't already have people they had worked with and teams they'd worked with forever, but there would be potentially new clients and new people to work with.

Sonal Mehta: The downside is the obvious downside. Nobody would ever hire me or want to work with me. I'd show up and have no work and nothing to do. The notion that I was going to be able to lead cases was a delusion. That was the risk, that that was all totally delusional, and nobody would trust me with their matters. Thankfully, people did trust me with their matters and it worked out okay, but that was the risk.

Sonal's decision-making framework, formal spreadsheet on top, instinct underneath, reminded me of my conversation with Rakesh Kilaru, who walked through the decision tools he honed at the White House and uses now at Wilkinson Stekloff to simplify trial strategy and career moves. Listen to my episode with Rakesh Kilaru.

Khurram Naik: Tell me about the spreadsheet. Were there three top factors? How did your spreadsheet work?

Sonal Mehta: Oh, Khurram, there are so many more than three factors. There were three tiers. In anticipation of this, you prompted me to go back and look at it, which I hadn't done in nine years. There were three tiers of importance. In each tier, there were multiple factors and they were given weights. Tier one had a 50% weight, tier two had a 30% weight, tier three had a 20% weight. Then there was a point value assigned to each factor from one to five.

Sonal Mehta: I'll give you a couple of examples of the ones in the different buckets, so you can see what was driving it. In the first tier, the highest-importance tier, independence was one of them. Going back to what I think ultimately drove the decision in a lot of ways. That was a really important factor. Collegiality and collaboration was really important to me as well, and that was not something pushing me away from WilmerHale. If anything, that was weighing in favor of staying, because I had a family there in terms of the people I'd worked with. But that's super, super important to me, working somewhere where I was on the team, I was part of the team, the team had my back and vice versa, and there was no internal competition. Easy-to-work-with clients was on there, because the quality of life you have as a lawyer depends a lot on the clients. Having clients that are collaborators and partners and respect their outside counsel and view it as a long-term partnership is super important. There are some clients that are easier to work with than others, and it was important to me, from a quality of life perspective, that I would have clients that would fall in the easier-to-work-with side of the scale. Practice reputation, those were kind of in the top tier in terms of importance.

Sonal Mehta: The second tier, I'm not going through all of them, just examples. Second tier was tranquility and lack of internal politics, competition, drama. Feeling like you're at an institution that's a stable institution, where everyone's generally rowing in the same direction. That was important and that was in tier two for me. Senior lawyers that would be mentors to me was on the list. As much as I was looking for independence, I definitely didn't want to be in a situation where I didn't have access to high-quality, high-caliber senior lawyers who could mentor me. The size and complexity of the matters I would work on was in that category as well. It was important to me that the quality of my peers would be incredibly high, both from a collegiality and interpersonal perspective and from a, these are all lawyers that I think are amazing and really talented, and learning from them, and I'm proud to be at the firm and be their colleague.

Sonal Mehta: The third tier included things like location and my commute. It included things like firm economics and stability, which I'm not sure should really be a third tier, but it was at that time for me. It was a little bit more of a structural question at that particular time, because I was deciding between a big law firm and a boutique. So there was less about sort of evaluating the financial stability of the individual firm, as more of the model question. Work variety and diversification was also on my list in that third tier. What you would find interesting, maybe, is that comp, like compensation, was in the third tier, and it was also expressly termed as compensation over five years, because I wasn't really focused on compensation in the first few years at all. Even over five years, it was only a third-tier consideration for me.

Khurram Naik: Looking back in terms of doing a post-op of that decision, were there factors that turned out to be almost irrelevant? I ask this because there's another partner I know who made a move and worked with a skilled recruiter. The recruiter explained to him, let's figure out what's important to you in advance. As he was going through interviews, this partner would rank the different firms by this criteria and also rank which firm he was enjoying the most. And then the recruiter could have pointed out, hey look, the things you said at the outset were most important to you aren't in fact the things that you're valuing most in the firm. What you thought was important is not as important as you thought it was. Did you experience that in life? Or was it pretty validated that the things you knew in advance to be important turned out to be the things that were really important to you?

Sonal Mehta: The things that I thought were important to me, I think did turn out to be important to me. But part of the reason for that is there are literally like 25 things on here. So it's hard to miss anything. I covered every single possible factor you could have. It was not the case that as I was going through my process, I was like, oh, I didn't have that on my list, but now I'm realizing that's really important. Everything was on my list, important or not. What I did find that's consistent with what you just said is, looking back at it, it's very clear to me that the numerical values I assigned for these different things are not in any way objective, and were completely driven by what my gut was telling me the decision should be. That was driven by independence. As much as I loved WilmerHale, the thing that drove me to go was feeling like I kind of needed to do my own thing and see, sink or swim, what it would be like just to be me. Everything about this matrix and the values I filled out, I think were colored by that. As much as I thought I was doing this super-rigorous diligence process and very objectively assigning these point values, I don't think I was.

Khurram Naik: Did the fact that the WilmerHale team was your family, did that cut in the direction of, oh wow, I shouldn't leave, as equally or did it just as equally factor into, hey, they're always going to be in my life in some way?

Sonal Mehta: You're right, that's what turned out to be the case. The people I was close with, I stayed close with. I'm still their cheerleader and I root them on and want them to be successful. At the time, though, when you're in that moment, you don't have the clarity to know that the people you're going to be friends with, you'll be friends with forever. At least I didn't. Part of it was, that's the only real job I ever had. I had a summer internship in college, and I was a paralegal for six months between college and law school, and I taught LSAT and GRE classes through the Princeton Review. But the only real job I'd ever had was working at WilmerHale, and I'd been there forever, and I had been with these same people forever. At the time, the people I was closest with, I knew we would still be in touch, but I just thought it was going to irrevocably change the nature of our relationship. I thought they would be mad at me. I had a lot of guilt around leaving. So it wasn't a comforting thing that I was really close with them. I think it actually made the decision so much harder. If I'd had a little more separation from them and hadn't felt so close to them, it would have been easier, and I would have made the decision a lot faster than I did.

Khurram Naik: What led you to move from Durie Tangri back to WilmerHale?

Sonal Mehta: Again, this was a similar process, which is, these are things that at least for me are more about external or internal pushes to take risks. Things were going great at Durie Tangri. It was a great firm, really, really, I mean, talk about punching above its weight. The caliber of the lawyers and the matters that small San Francisco boutique was handling was really kind of amazing. It no longer exists in that same form, but at that time it was really kind of amazing. Things were going great there. My practice was booming. I went from in 2019 wondering if anyone would ever hire me to be their lawyer, to having this booming practice, having all these amazing clients, and trusting me with things that frankly I'm not sure I was qualified at the time as a younger partner to be entrusted with, but I was learning and growing and rolling with it, and I was able to deliver great outcomes for some of these clients.

Sonal Mehta: The internal push this time wasn't independence, but it was, wouldn't I be able to do more if I had more resources? If I had more people, more expertise across different practices or different areas, couldn't I help clients solve bigger problems? Some of that was internal, and some of that also was from clients who were like, you know, such a great firm, you guys are awesome, but there's sort of a cap on what we can give you in terms of the scale of the matter because you just don't have the resources. Have you ever thought about what your practice could look like if you were back on a bigger platform? It was the coupling of the internal and the external push of, everything's going great, why would I take the risk? Well, maybe I should take the risk and see if the practice can expand into more complicated, more interesting matters or bigger-scale matters if I have the resources of a firm with broader expertise.

Khurram Naik: Why WilmerHale and not WilmerHale again?

Sonal Mehta: I had been working with WilmerHale on some matters as co-counsel and was really impressed by the lawyers. We had a lot of common clients. So the client map really kind of worked out well. There were a couple clients where unfortunately the conflicts wouldn't make it possible going forward, but by and large it was almost complete overlap in clients. That was really attractive. I'd been working with WilmerHale lawyers in a co-counsel capacity and had just a tremendously positive experience. Very often when you're co-counsel with another law firm, there are sharp elbows, competition, attempts to one-up one another in front of the client. With the WilmerHale lawyers, there was none of that. We were all one team, genuinely, and I was the outsider and felt that way. So that was really attractive to me. That was the pull to WilmerHale.

Sonal Mehta: Maybe this is just, someone said this to me later, and I don't think I was processing it at the time, but when they said it later, I thought, huh, that could be part of it. They said, you know, wouldn't you be worried that if you moved back to WilmerHale people would perceive that as a failure? Like, you tried to go out on your own and then you couldn't make it, so then you went back to the comfortable. I never thought that expressly, but maybe that was subconsciously part of it as well.

Khurram Naik: Part of what I'm interested in is some of what's made you successful as a lawyer. We've been talking about your core competencies. What would you say are the two or three things that you feel really drive your success?

Sonal Mehta: Given the way this conversation has gone, it won't surprise anyone to hear I think my gut and my instincts are pretty important. I also think, God, this is hard, I don't like talking about this sort of stuff because it makes me seem braggy. If I were hiring myself, if I were in-house counsel and I was like, why would I want to hire Sonal, if I had to come up with a list, I do think my instincts are pretty good. I am pretty good at figuring out what's going to matter and what's not going to matter. If we're dealing with a complex set of facts or issues, going back to my gut, I usually am like, okay, these things are going to matter, we need to spend a lot of time and attention. If it's a litigation, these defenses are going to matter, so we really need to develop our defenses here, or this witness is going to matter a lot, or this set of meetings in 2022 is going to matter a lot. For some reason, through gut or whatever experience or combination thereof, if you kind of lay out everything, I'll be able to tell you usually, here are the things I think are going to matter in the end, and here are the things I think are going to fall away over the course of the case.

Sonal Mehta: The third is, I may not be the best lawyer, but I do care a lot. There are a lot of really fantastic lawyers out there, and I'm not suggesting I'm one of the best. But if you hire me for something, or if I take on a client's problem, I am going to sweat it to the last detail. I am going to lose sleep over it. It's going to be the thing on my mind when I'm brushing my teeth in the morning. It's going to be on my mind when I'm driving to the grocery store on Sunday. Probably in a way that's unhealthy, I really, really, really, really care about my matters. I live and breathe them. They become my life for whatever period of time I'm involved in them. It's probably unhealthy for me as a person, but it probably does serve my matters well.

Khurram Naik: It does make sense, because you can't become really good at something if it isn't on your mind most of the day. And that was part of my criteria for being okay with pursuing patent litigation, because I just knew, I'm never going to be thinking about an expert report in the shower. I'm just not. The things you think about in the shower are such a great measure of what you're driven by. As for sitting in front of a laptop, there are only so many hours that even the most elite worker can do that. The real competitive advantage is if that's just always going on in the back of your mind, or at some point in the front of your mind, pretty much all day.

Sonal Mehta: Yeah, I do think that's right. I think it's also sometimes where the creative ideas come from. Sometimes I'll be in the car going somewhere and I'll be like, what if we did this crazy thing, and I'll call my colleague and be like, hey, I know this is totally random, but what if we did X, Y, or Z? And they'll be like, oh my god, yeah, and then we could do this, and then it's like that. It's not even maybe a concrete thought process. I wasn't sitting in the car like, okay, now I'm going to think about this case. Your mind just wanders, and mine never shuts off, ever. The most creative things come to me when my mind is just wandering. A lot of the brilliance when you see someone do something really brilliant in this profession is not the playbook. It's something that came up kind of totally out of left field, or someone's creative idea. I aspire to do that more than I do. I would love to be the person that's always coming up with brilliant creative insights.

Khurram Naik: Tell me about the parts of your work that you enjoy the least. Depositions you love. What do you dislike about litigation?

Sonal Mehta: This has changed over time, as you might expect. When I was a younger lawyer, I used to love discovery, which is a weird thing to say, I know, but I used to love it. I used to love the meet-and-confer with the other side and the letters that you write back and forth, the sort of, it was fun, it was outsmarting the other side on a discovery issue. I used to really, really enjoy that. As I have gotten more senior, or just older maybe is really what it is, I find so much of the back and forth of litigation to be unnecessary and focused on things that don't really matter. There's so much posturing that happens. There's so much lack of civility that goes on. Maybe it's that it's getting worse, maybe it's just luck of the draw of the people I'm interacting with, maybe it's me having less tolerance for that as I get older and grumpier, but that part of this job I could definitely do with less of. Discovery is necessary and appropriate and we have to do it, but a lot of the incentives people have are really perverse in the discovery context, or in litigation generally. There's not as much discipline as there needs to be around that, and it's really a shame, because it's such a tax on our system and such a black mark on our system that we all spend so much time and money fighting over things in non-productive ways, and people end up becoming uncivil or completely unreasonable in that context. I'd say that's one thing I like less.

Sonal Mehta: I hate doing bills and time entry and all that stuff. I have said to many people, this job would be perfect if you didn't have to do any of the money associated with it. If I didn't have to go out and do budgets or enter my time or submit bills or follow up on bills, if I were infinitely, independently wealthy and could just be a litigation partner for free and never had to think about any of the money associated with it in any direction, I'd be very happy.

Khurram Naik: There's another role you've taken on. You are on the management committee, which is a lot of responsibility for an institution, a big institution. A couple questions on my mind. One is, I've talked to other people I've interviewed, like Moez Kaba, who's a managing partner of Hueston Hennigan, and Kalpana Srinivasan, who is the co-managing partner of Susman Godfrey. Both are trial lawyers with very busy dockets, and then also in this management capacity. How do your trial preferences inform your approach to being on the management committee, and vice versa?

Sonal Mehta: One thing is, thankfully, I'm just one of many members of our management committee. So unlike Kalpana and Moez, who have to balance their trial practices with actually running the firm, we have a real managing partner and deputy managing partner who do the work, along with a tremendously talented executive team that do all the hard work. The way I think about it, I'm on the management committee of the firm, and I'm involved in leadership of the litigation department, and I'm also now the partner in charge of our Palo Alto office. So thinking about management from a few different angles.

Sonal Mehta: The way my litigation background influences the way I think about management, and I think it really annoys people to be honest, and probably rightly so, is I ask a lot of questions. The way my mind works as a litigator is to interrogate everything. We have to make a decision about something, and my first instinct is, okay, well, what about this, and what's the basis for that, and what's the fact that supports X, Y, and Z, and where do we get that data, and what's the other data, and what's the source for that data. I start to ask all the questions you would have if you were a litigator either getting a position ready to present, or if you were the judge going through and trying to make a decision. I interrogate everything. Sometimes I interrogate things that probably don't matter. It's my instinct to ask a lot of questions. That's how I think my training as a litigator influences the way I think about management, because I have a small role among a lot of super-talented people that have tremendous judgment and wisdom, and I'm just trying to add some value where I can. The way I think about my value is asking all those questions, because maybe a lot of them are obvious or a lot of them don't matter, but maybe every once in a while, I will ask a question that's a different way of thinking about it, or make an underlying point someone else hadn't thought about, or elicit new information or data that contributes to the conversation in a way that's helpful.

Khurram Naik: Has your role on the management committee influenced how you litigate?

Sonal Mehta: I think it has, in ways that I could sort of concretely express, but also subconsciously. One is that the people I'm on the management committee with are people I might not otherwise get to spend a ton of time with, because our management committee includes people from other practice areas and other offices. I would know them, but I wouldn't really know them well, and I wouldn't get to work with them. I get to sit in a room with them and talk to them and hear how they think about things and how they go about making complicated decisions. There's a perspective I'm able to gain from these incredible lawyers I would never otherwise get to see, that has really been valuable for me. I don't know that the last time I had a decision to make in litigation, I was channeling someone from the management committee, but I do think we all absorb things we learn from other people, and being surrounded by these brilliant leaders, I have to be absorbing from them, and that's making me better.

Sonal Mehta: The other thing, in the same vein, is taking a step back and thinking about the big picture, taking a step back and thinking about the perspectives of people that don't have the same experience as you. We always have to do that as litigators and trial lawyers, because we're going to ultimately have to present our case to a judge or jury that doesn't have the same perspective we do, or the same information we do. But when you're thinking about running a firm that has a lot of different people in a lot of different geographies with different practices and different clients, every decision you make, you have to affirmatively step back from your own perspective. While you want to contribute your perspective, because the reason we're elected presumably is so that all these different perspectives are reflected, you also have to very consciously say, okay, but that's great, how does that impact this other office, or this other practice area, or this other set of clients, or this other industry? As a litigator, and especially someone getting more and more senior, dealing with really complicated webs of considerations and problems and legal challenges, and doing a lot of advising clients even outside the courtroom on those kinds of problems, the muscle memory of forcing yourself to take a step back and think about it from the perspective of other constituencies has been really valuable. That came from management, and I think it's now a big part of how I think about how I advise clients as well.

Khurram Naik: Speaking of looking outside for inspiration, is there a firm that you really admire?

Sonal Mehta: There are so many firms I admire for so many different things. I was thinking about this question, and I predicted you might ask it. This is like a totally apples-to-oranges comparison, but that's part of why I was thinking about it. You mentioned earlier Kalpana, that you interviewed Kalpana, who is co-managing partner at Susman Godfrey. That firm is so completely different from our firm. I think it has to be. Our system only works if there are firms like that, and firms like ours, and different types of matters and different types of clients. We just are operating in different areas of the industry, and the industry needs both. I really do respect so much of what a firm like that does in terms of the way they think about the business, the way they think about recruiting and retaining talent, the way they structure their trial teams, the tremendous trial successes they've had, the business successes they've had. We could never be that firm, and it would make no sense for us to want to be that firm in every respect. But I do really respect a lot about what I've observed about that firm from the outside. We should always look for learnings from firms that are a lot like ours, but also from firms that are really different, to see what parts of the way other people are doing it we can steal.

Khurram Naik: Is there a lawyer whose career trajectory you really admire?

Sonal Mehta: I really hope that they don't listen to this, so we're going to try to avoid ever mentioning I did this podcast, so that I don't embarrass them. Someone that's been really influential in my career is Paul Grewal, who I suspect a lot of your listeners are familiar with. I knew him when he was on the bench, and I appeared before him as an associate, and have very fond memories of that. Then I knew him when he was at Facebook, and know him now that he's at Coinbase. Part of this is, I couldn't be more grateful to Paul than I am. In terms of impact on my career, he's probably one of the top three most impactful people I've ever worked with as a mentor, and he was really largely responsible for the expansion of my practice to move beyond just IP litigation to also covering all types of complex litigation matters, because he gave me my first non-IP matter. I can't imagine why he thought that was a good idea, but he did, and then it grew from there.

Sonal Mehta: Setting gratefulness aside, objectively thinking about why I admire him so much, there are a couple things. One is he is in some ways the epitome of the, everything's going great and then you break it anyway and go do something else. If you think about his career, he's a great IP litigator, and then he takes the judgeship, and then he's one of the most well-respected judges anywhere in the country, and people were desperate to be in his courtroom as much as possible because they loved being in front of him. And he gave that up to go take this really hard, complicated job at Facebook, and then he's running litigation at Facebook and is in the thick of it, dealing with the most sophisticated, most complex legal issues, and it's going great. And then he goes to be the CLO at Coinbase, and is now in crypto, as if it was going to be easy to be the CLO of Coinbase in the current environment related to crypto. It's really hard to walk away from something when it's going great and go into something that's going to be harder and more uncertain. He's the epitome of someone that's done that over and over again, and just jumped in and then killed it when he went to the next place. I admire that so much.

Sonal Mehta: The other thing I really admire is, we were talking earlier about civility. He is really tough as a judge and as a client. He's super smart. He asks hard questions. He's not giving anyone a free pass. But he's so unfailingly kind. I remember being in his courtroom and I was waiting for a discovery hearing, and there was a matter before ours. I think it was a traffic violation or parking ticket on federal land, so it actually went to a federal judge. I was there for this massive discovery fight, a really consequential discovery fight in massive IP litigation, big tech companies, big law firms on both sides, high stakes. And then there was this small matter, probably a few hundred dollars at most. I think it was a parking ticket. They were before us, and he was just so respectful. It was an individual, it wasn't even a lawyer. He was so respectful to the individual, welcomed them to his court, went through the process, gave them full airing of the issues, full opportunity, explained the process to them. And then he came in and did the exact same thing for our big fancy high-stakes patent dispute. I was thinking, that kindness and respect, which I've seen him have in every context, God, I wish we had more of that. I wish we had more of that in the law, I wish we had more of that in the world. I wish we all had that kind of respect for every single person we encounter. I admire that a lot too.

Sonal's description of Paul Grewal's courtroom, tough on the merits, unfailingly kind to everyone in the room, echoes how Judge Vince Chhabria talked about running his docket: process and civility as the substance, not the packaging, of justice. Listen to my episode with Judge Vince Chhabria.

Khurram Naik: I observed that from a great judge in the Northern District of Illinois, Chief Judge James Holderman. Routinely he had people pro se, and there's a selection factor for the kinds of people who have a pro se. They tend to have no case, they tend to be, shall we say, cranks, or potentially have some mental health issues. I observed, just like you're saying, that character of how he approached those people and those conversations and those hearings. He said of that, my approach is, I'm a public servant, and part of why I'm here is to give people an outlet so that they don't take out their anger on the world in some other format. I think that was beyond his job. He went beyond the call of his job as someone who's genuinely interested in the public well-being and policy. It sounds like Paul is the same way. Part of what you're talking about in admiring Paul is his willingness to bet on himself and invest in himself. Can you share some tips for people at any stage of the career, could be geared more toward junior people, but at every stage of the career we're all trying to grow something, right? You talk about business development, that's the frontier for you. We all have something we're developing. In terms of advice on investing in yourself or betting on yourself, what frameworks or tools do you want to impart on people for identifying opportunities and investing in yourself to make the bet?

Sonal Mehta: Part of this is, you have to kind of get comfortable that you're going to do things that are not always going to work out perfectly, but you've got to be willing to take risks. Some of the best things that have happened in my career have been risks I've taken, or things I've done where I was like, I don't know why I'm doing this, but I'm just going to go with it, and great things can come from that. So part of betting on yourself is getting comfortable with the risks.

Sonal Mehta: I also think part of it is, it's easier to bet on yourself when you know you have the safety net of support. I think that comes from mentoring and from people that are your advocates and your supporters. I've gotten incredibly lucky in that arena, from so many different people at different stages of my career. But the thing that's really important about that, looking back, is it's easier to bet on yourself when you know you've got those people. It's easy to have preconceptions about who those people are going to be or what they're going to look like. I would just urge especially the younger lawyers to not worry about that. Anyone that's willing to invest in you and your career and your development, grab that person. Try to get them to engage with you. Try to get them to invest in you as much as possible, because if they invest in your success, it's amazing how much more successful you have, right? If all these brilliant successful people are invested in you, they're going to want to see you do well, and that's going to help you.

Sonal Mehta: For me, I didn't have really any women or people of color as mentors when I was a very young associate. But I had amazing mentors who were men. It was great. They went out of their way to help me in every way possible, with no reward for themselves, give me opportunities and support my career. If I had been really focused on finding a woman of color mentor and closed myself off to that, I would have cut off all this mentorship and support.

Sonal Mehta: Another example: I had this really hard-fought case against another firm for many years. There was a senior partner on the other side. Now that I'm thinking about it, this has happened to me twice. There's a senior partner on the other side, who, as much as the cases were hard-fought and litigated aggressively on the merits, in both of these cases, the senior partner on the other side after the case was over reached out to me and said, they were both men, by the way, neither were people of color, they were both white men, and they were a lot older than me, and they both reached out to me, a decade apart, and said, I think you're really tremendously talented. If there's anything I can ever do to support you in your career, I really hope that you'll reach out to me. These were my opposing counsel. We should grab that mentorship and support anywhere we can get it, because it will allow you to take those risks and bet on yourself.

Khurram Naik: I think we have a lot of food for thought here, and I think, notwithstanding your initial counsel, there are very interesting stories and ideas you have throughout your career. I'm really glad we took the time to explore those.

Sonal Mehta: Thank you so much for having me. I'm not sure that that's true, but as I told you when we first embarked on this, if there's even one younger lawyer that actually made it all the way through this and listens to it and found a nugget or two that might be helpful to them as they're navigating their career, then it was a joy for me to do it, and it was well worth it. I'm grateful to you for the time and the opportunity.

In this conversation, Silpa walks us through the specific techniques and principles that shaped that rise. We dig into how growing up as the child of immigrants trained her as an advocate from a young age, the creative legal arguments that built her reputation at Quinn, why being underestimated is a gift, and what it actually takes to launch a firm from the ground up with a one-tier partnership and a trial-first culture.

Keep reading below for the full episode and the complete transcript of our conversation.

Top Insights

Below are the highlights of our conversation:

• Childhood Advocacy as Legal Training: Growing up as the child of immigrants, Silpa frequently spoke up for her mother in everyday settings because her mother worried about being treated differently because of her accent. That early experience of advocating for someone else, and of translating complex systems for people who had no context for them, became the foundation of her work as a litigator today.
• Take Up Space, Get Given More Space: Silpa's breakthrough principle was to volunteer for hard assignments early, even when it felt risky. On one case with a tight budget, she took essentially every deposition herself as a junior associate. The experience compounded, each opportunity earned the next one, and her willingness to jump into spots other people would not occupy became her biggest differentiator.
• Being Underestimated Is a Gift: Young and South Asian in an industry where that combination was rare, Silpa sometimes had adversaries who assumed she would be easy to run circles around. Her answer: if the other side does not see you as a threat, they never see you coming. Time and again she turned that underestimation into a tactical advantage.
• Creativity Needs Both a Person and a Culture: Silpa believes creative legal reasoning requires two things: the lawyer's willingness to voice ideas and a culture that invites them. She credits Quinn for fostering that early in her career, and she has built the same expectation into Elsberg Baker Maruri by asking associates what they think about strategy on every case, not just the narrow piece in front of them.
• A One-Tier, Trial-First Boutique: Elsberg Baker Maruri was intentionally designed to stand apart from the market: fully equity partnership with no tiers, litigation only, trial focused, and nimble enough to run expedited matters from pleading to trial in five weeks. Silpa argues the demand for boutiques this year reflects a broader truth about the market, clients hire lawyers, not law firms.

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Full Transcript

Khurram Naik: Silpa, I'm so glad that we're sitting down to talk today.

Silpa Maruri: I'm very honored to be here.

Khurram Naik: Okay, so Silpa, we have a common experience growing up. We both have immigrant parents. And something I've heard from other immigrants, not just from South Asians but elsewhere, is this common experience of children as advocates for their parents and as intermediaries, being asked to explain things or translate things beyond just the literal words. It's more advocacy for your parents, and parents rely on their children for that. I think you have some stories about growing up and your parents asking you to step into that role.

Silpa Maruri: Yeah, definitely. One of the stories I was telling you about is pretty straightforward. We'd be in a Costco or a Walmart, and we'd need to ask a question about something, just a really straightforward question. Do you have this in another size or another color, something like that. And my mother would always ask me to do it. Sometimes I would push back because I was a young kid, and I'd say, you should be the one asking, they're going to look at me like I'm crazy because I have this little kid asking them questions about inventory. And she would always say she didn't want to, because she felt they would be rude to her because of her accent. So she would very frequently make me occupy that role instead of her.

Silpa Maruri: She's very good at English, actually. She's very well educated. Nobody would ever have a problem understanding her through her accent. But she was just worried that people would treat her differently, and she thought that me having an American accent would mean I'd get very different treatment from her. In a way it was good, though, because what it did was teach me to be very comfortable speaking with adults, even as a child, and even adults I didn't know, because I had to out of necessity. That was one of the ways I served as an advocate for her. I think that happens a lot with children whose parents have accents, or children of immigrants, because sometimes there's a level of discomfort. The parent knows the child is going to be accepted in a way the parent isn't. And it was good for me in terms of gaining experience I used later, because from a very young age you learn to be that advocate for somebody else. When you get into a job that is pure advocacy, like being a lawyer, that was training from a very, very young age I wouldn't give up for anything.

Khurram Naik: I think there's lots of career paths you could have had. Maybe you would have been a doctor or a business owner or some other path. So you didn't have to be a lawyer. It's easy to look back and cherry-pick experiences that impacted you later on. But that seems like a pretty reasonable one that would have big impact on your skills as an advocate. Is there anything else from your childhood where, looking back now, you feel there's a legacy or an impact from those early experiences?

Silpa Maruri: Sure. Another thing I frequently had to do, that I think a lot of people in my position have to do, is translate things that were going on in my everyday life for my parents, because it wasn't a part of what they experienced when they were growing up. The school system here is really different from the school system in India, where my parents grew up. There would be a lot of times where some project was due and they just had no context for why, because they had never gone through a similar school system. A lot of my childhood was spent translating what was going on and making it understandable to them, making it something they could digest and get their arms around.

Silpa Maruri: That is something we do as lawyers every day. We have to take something complicated, something that seems foreign, something outside the mainstream of what a regular person has to deal with, and we have to translate it into something that your everyday juror can understand. That teaching I had to do even as a young kid is something I find very useful as a litigator today. If I go in front of a jury, or even in front of a judge, there's a lot of translating that happens in terms of taking something complex and distilling it to its core essence. That's something I've had to do all my life. It comes pretty naturally to me.

Khurram Naik: Did you have any early inclination that you were going to go to law school?

Silpa Maruri: Certainly not as a young child. I don't think that's something I thought I was going to do. But by the time I was in high school, it was of interest to me because I loved writing. I loved this sort of teaching translation role I've described to you. And I loved the art of argument. It was something that was always on my mind as a possibility. It crystallized for me more once I went through college and saw a little bit more of what you could actually accomplish as a lawyer and understood a little bit more about the legal system than I did at a young age.

Khurram Naik: And when you went to law school, you didn't expect to be on the track you're on now, right?

Silpa Maruri: No, and we spoke about this. I actually went to law school thinking I was going to be a public interest lawyer, interestingly enough. I had done Teach For America, and I had a very significant body of nonprofit experience when I was in undergrad. I had done some basic tutoring for underrepresented youth and that sort of thing. So I went with a real public interest focus. It was actually by luck that I ended up in a law firm environment. I went through OCI and thought, let me give this a chance and see what it looks like in real practice. I wound up going to a firm thinking I would really leave in a short period of time.

Silpa Maruri: What I discovered while I was there was that I really loved complex corporate litigation. I didn't think I was going to have the same experience in a public interest environment. The work public interest lawyers do is obviously extremely laudable, and I have deep admiration for that. But what I found in a law firm environment was I loved the complexity of the problems. I loved looking at really complicated transactions and trying to figure out a creative angle. I loved the complexity of the litigation itself, the subject matter, the legal problems presented in corporate transactions. And I loved being around an environment filled with intelligent, hardworking people deeply engrossed in wrestling with that sort of content. And I was very good at it. The combination of those things really made me stay. Strangely, I'm not in this job because of the money, I'm not in this job because of the glory. I'm in this job because I'm the bizarre person who really loves grappling with these thorny corporate questions.

Khurram Naik: Your trajectory is pretty astonishing. You graduated from law school in 2011, you became partner at Quinn, and now you've launched your own law firm. That does seem like a remarkable set of accomplishments in a short period of time. What do you attribute that to? What differentiates you? There's lots of smart, hardworking lawyers, but you've had exceptional success. It's not going to be a single answer, but what do you think were some of the early experiences in practicing that set you on this pathway?

Silpa Maruri: Yeah, I appreciate that. I think it was a combination of things. My early experiences in particular were that I found the more I put myself out there to take up space, the more people wanted me to take up the space I was taking up. So I proved myself to be very skilled very early on, and I always threw my hat into the ring by volunteering for opportunities, even difficult ones. For example, I was on a case where there was a really restrictive budget. I was very junior at this point. The client didn't want to pay to have a partner take every single deposition or most of them. So I very willingly took essentially all of the depositions in the case, even the most important ones. It was difficult because there was a very restrictive budget, I hadn't done it before, and I was doing a lot of them back to back. But as a result of that case, I got tremendous experience taking high-level depositions very early on.

Silpa Maruri: My work ethic was really a big differentiator between me and other lawyers, because I was always willing to do things to go beyond the ordinary, which always resulted in me getting more experience early on. And I was good. I was skilled, and I applied my intelligence in a direction that helped me. I wouldn't have been able to succeed on intelligence alone. I don't think anybody enters a law firm environment and succeeds on intelligence alone, because that's the price of entry. But combined with my willingness to really throw my hat into the ring every time, and to do a little bit of that self-advocacy I was talking about earlier, it helped me get a lot of experiences early. It was cyclical, once I got one experience and did well with it, it lent itself to me getting a different experience later, and so on. It evolved very naturally at the time. Looking back, the thing that really helped me was being willing and able to jump into spots other people couldn't occupy.

Silpa Maruri: A lot of younger attorneys will shy away from opportunities like that because they're a little bit worried about the amount of work it entails, or they don't feel like they have enough time to do the thing they're being asked to do in the way they want to be able to do it. I really embraced a little bit of risk in that way. There were times I didn't know if I was going to be able to take a deposition for the first time and excel at it, but I did it because you have to do that in order to be a good lawyer. You have to force yourself to take the next step. You have to force yourself to take the opportunities as they come. All these tiny doubts I had about whether I'd be able to do something well the first time ended up being largely unfounded.

Silpa Maruri: The other piece of the puzzle was putting in the work to excel. You're not going to excel just because you want to excel. You're going to excel because you really dig in, learn the facts, learn the law, and map a strategy every time you're doing something. I was very intentional about always doing that for every big project I was working on.

Khurram Naik: That's something a lot of lawyers early in their career find challenging. It's enough to learn the substance of the work, how to communicate with partners and clients, and just that alone is plenty. But then advancing to a more strategic role, to say, hey, beyond the task, here's what I have, not only maybe the partner's big contribution in mind, but also potentially my own vision of what should be done here. I think that was challenging for me as an associate, and I think that's challenging for other lawyers who are very good at doing the work but have a challenge around saying, hey, I can be creative, I can be a creative legal reasoner. How did you make that leap?

Silpa Maruri: It's a good question, and I think there are two components that have to be there to make it possible. One component is you have to be willing to do it yourself. The other component is you have to exist in a culture that allows for it. I just happened to be at a place where people really fostered that. As you know, I came up at Quinn Emanuel, and people really invited a lot of creative thinking from their younger associates. A lot of the folks I worked with early on realized I was this very good creative legal reasoner, and they would come back to me time and time again because they knew I would be able to see things other lawyers didn't see.

Silpa Maruri: That's something we also try to be very intentional about at our own firm. We're very interested in developing our young lawyers and not just treating them as functionaries or cogs. We always try to get input from the younger members of our team on even minor aspects of strategy. That's twofold. One reason is it benefits us, young fresh thinking is never a bad thing, particularly when you're dealing with, for example, financial products that change all the time. The other piece is it also develops the lawyer. The more somebody's being asked to flex their legal reasoning muscles and to think hard about big, important legal problems, the better they're going to be at it when they are in more of a leadership role. That's something we really try to foster here, and part of the reason is because each of us, even though we're coming from different places, did have people in our spheres who did that for us. It yielded dividends for us, and it also yielded dividends for them, because oftentimes we would come up with a case-breaking theory.

Khurram Naik: You mentioned creativity. When did you notice creativity in yourself early on? What's an inflection point where you felt like, wow, I just realized I did something really creative here, where you got some feedback in that way?

Silpa Maruri: That actually happened to me fairly frequently. Like I said, that was something I was good at even early on, because I like legal reasoning and I like complex problems. I would frequently look at something and see an angle somebody didn't see. An example that comes to mind: I was on a case where there was a contract dispute, and our client had one interpretation of the agreement and the adversary had another. A lot of the adversary's documents about what they really thought the contract meant were behind the veil of privilege. Meanwhile, we knew they didn't actually believe in their interpretation. So we had to find a way to get at these other documents they were hiding under the cloak of privilege.

Silpa Maruri: I looked at the communications that had gone back and forth and realized they had not drawn a real line about privilege. They had kind of woven in and out of privilege if you really looked at the documents in a way that suggested they had treated us as if we were within the privilege, or waived the privilege. I came up with a very complex argument about why the privilege actually didn't apply. The end result was that the court found they had waived privilege. They had to produce all of their privileged communications, so much so that at the end of the litigation they didn't even have a privilege log, because they had literally produced every single document they had called privileged that was responsive. And the end result was that we were right. They didn't have the interpretation of the agreement they said they had. It was something they came up with for litigation. The documents we got from them showed that was true. It was devastating to their case. That's an example where, if I hadn't been asked as an associate what I thought the strategy should be, that never would have happened. That's why we value it so much here, because ourselves had so many experiences as associates where we came up with case-breaking theories.

Khurram Naik: So it sounds like you were taken seriously internally, where you were consistently treated seriously. By counterparties?

Silpa Maruri: No. And I don't think there's a lawyer in America who will say they have been, particularly as a young lawyer. As I said, I had a lot of experience very early on, and I had a lot of responsibility early on. Sometimes that resulted in my adversary underestimating me, because sometimes people say, oh, this is a young lawyer, I can wrap them around my finger, I can run circles around them because I have so much more experience than they do. I would say the lesson from that is that the best gift your adversary can ever give you is underestimating you. If you don't think anybody's a threat, then you never see them coming. I proved time and time again, when those situations arose, that I was up to the challenge, and usually I think people ended up regretting it.

Khurram Naik: Is being underestimated something you've encountered in your career generally?

Silpa Maruri: Look, I'm not going to say it doesn't happen. But I will say one thing I really enjoy about practicing law is that ultimately it is a merits debate. You're arguing about whether the law and the facts conform to a set of rules. That experience has been really gratifying, because yes, you will encounter some amount of nonsense all along the way, everybody does in every single litigation, but I think the beautiful thing about being a lawyer is that at the end of the day you're debating about something that has a clear set of defined rules and a clear arbiter supposed to resolve all those rules. You may not always love the result you get. Every litigator worth their salt has litigated a case they've lost that they felt they should have won. If you're not doing that, then you're just not taking the hard cases. But at the end of the day, for the most part, we've created a system founded on impartiality and on applying a set of rules. In my experience, that has largely been true, and it's been gratifying, because that's not true in every walk of life.

Silpa's take on being underestimated as a tactical gift reminded me of my conversation with Priyanka Timblo, who talked about how being doubted shaped her preparation heading into the trial that delivered a $101 million verdict. Listen to my episode with Priyanka Timblo.

Khurram Naik: I think that's our favorite part of the practice, that there's creativity to me, but there's also a set of rules, and that's a really interesting axis. At the end of it, there's a merit component. But I wonder how much you think there is an edge with understanding the judicial system. Let's say a judicial realist approach, how much do you buy into that? Let's say this judge, maybe you had some inkling this judge would find this nature of procedural dispute to be persuasive. Maybe this judge is more willing to rule on things or is just a little bit edgy. In any given district, there are judges that have more risk tolerance for things that could be overturned or not. How much is there a skill or an edge in understanding the judicial system in that way?

Silpa Maruri: I think it's there. I don't think anybody can really deny that these things make differences at the margins. But what I'd say is they make differences at the margins because of the way the system is designed. To those who say it's not a good system, I challenge you to define something better. It's very hard to design a perfect system in an imperfect world. It is not perfect, I will say that. Those things will matter, those things will make a difference. But fundamentally it is an elegant system and a very good one.

Khurram Naik: Going back to your progress at Quinn, then you're having all the success and you make partner. You're young to make partner, that's impressive. Had you, at the point of making partner, identified what in particular you enjoy the most?

Silpa Maruri: Yeah, for me, I loved most of the things you do as a lawyer. I obviously loved the stand-up work. I loved doing arguments. Oral arguments were something I really thought were fun, and I had a real skill at putting things in perspective, boiling things down to their core, simplifying complicated concepts. That was something I was really good at. I also loved doing depositions. I loved writing briefs. I am a lawyer's lawyer, and what I found by the time I was going up for partner is I liked doing all of the core components of the job.

Silpa Maruri: What I would say to somebody who's about to do that is you really have to think about whether this is something you truly love. Because it's very easy to take the road of least resistance and say it's the easy path to try to continue to be a litigator, try to continue to be a lawyer. But the people who really have the best experiences, and frankly who are the most successful, tend to be the people who have a genuine affinity for the job. They like doing the strategizing, they like doing the legal thinking, they like doing the work. Because at the end of the day, you work so much in this industry that you really have to love what you do, or you can really make yourself miserable.

Khurram Naik: By the time you're a partner at Quinn Emanuel, what's a part of the job you didn't enjoy?

Silpa Maruri: That's a tougher question. I generally enjoyed everything, and by the time I was a partner, I was doing a lot less of the things people don't like. I can't say I loved every time I had to do some doc review. I don't think anybody likes doing that. But by the time I was a partner, I obviously wasn't doing that sort of thing, or even when I was close to being a partner, I wasn't doing that sort of thing. That's a good lesson for the folks who are coming up, that some of the things that are less glamorous about the job become less of a core component of the job as you get more senior.

Silpa Maruri: At our firm in particular, we're very intentional about making sure associates get to do the things that are more fun. We want to make sure associates get stand-up experience. We want to make sure associates do get to do arguments. We want to make sure associates do get to do depositions. It's front of mind for us. Every time we're in the midst of a case, we think what can this associate do, what opportunities can we give this person. As a younger lawyer, when you're thinking about the menu of options in terms of law firms, that's a very important thing to think about. Is this a place where, when I look back in 10 years, I'm going to be happy I went from an experience-gathering point of view? We try very hard to be that place. I tried very hard to be that person even when I was at Quinn. I try even harder at it now, because it yields dividends for the firm. It's impressive what young lawyers can do. They come in with a set of skills, and I think oftentimes young lawyers are underestimated in terms of what value they can bring to the table. We don't want to make that mistake of underestimating them. We really try to give them opportunities very early on.

Khurram Naik: What would it take for you to take the leap? Partnership at Quinn is one of the best litigation-oriented firms in the nation, a very strong litigation practice. In some sense it was risky, and you had a lot to lose. At what point did you know you'd be willing to even do something like that? Or did it just take you by surprise as a partner, saying, I can't say no to this? How far back do the roots of that entrepreneurial venture and that risk taking go?

Silpa Maruri: Yeah, it's a good question. Let me start by saying I have deep respect for Quinn Emanuel. I left there on very positive terms, and I have a lot of close friends who are still there. It wasn't as if I didn't like it there. The reason I left was because I saw a real opportunity to be an entrepreneur and to build something that was a true reflection of me. A lot of the ways I've described to you during this podcast about a culture of mentorship, about creating a firm that is trial focused, about creating a firm that has a certain type of culture that I really wanted to build from the ground up.

Silpa Maruri: We've also talked a little bit about who I am and where I came from. It's been really gratifying to now be able to serve as a mentor to people coming up who look like me, who weren't necessarily always around when I was coming up 10 years ago. It's nice to finally be in a position to help other people in that way. Those were a lot of the reasons why I decided to go in the direction I did. And I'm very happy, because the firm is doing exceptionally well. We've got really great recruits. We've picked up some fantastic exemplary candidates. We've got a number of trials we're headed into this year. We have six trials in our first year, which is incredible for a firm that's only existed for four months. We've created what already feels like a very positive culture around mentorship and giving opportunities to associates early on. On one of the trials we just finished, associates played a huge role in examining witnesses at the hearing. That's something we're very proud of. It's something we openly tout. It's also something clients really like, because, as I said, often associates and younger lawyers are underestimated. But once people see them on their feet, they're really astonished by what they can do.

Khurram Naik: How did you come to this idea of taking this risk? Another lens on this is, you're South Asian, you're a woman. There hasn't been a lot of influence in the legal industry from that demographic. How did you come to realize it? It sounds like there's this wedge where you started reshaping the firm. You took up space, as a phrase you were saying. How did you feel like you could take up that space, in being this minority, in whatever sense you want to use that, in the law? How did you feel you could start to take more and more space, such that eventually that seems to be part of the roots of departing and launching your own firm?

Silpa Maruri: Yeah. I would say from early on I adopted the mindset that the client was my client. The client is of course a firm client, but the client is also somebody that every single lawyer on the team has a responsibility to. I always felt the weight of that responsibility, even as a very young lawyer. I felt very much that my role was as an advocate for that client. If I saw an angle, I saw an idea, I saw something I felt would be valuable, I voiced it. You always have to find a way to voice things respectfully. You don't want to go off on your own and run up a huge bill looking into something the partner has already thought about or doesn't think is valuable. But I found ways to offer my ideas in a respectful manner, and in a manner where I didn't run off the reservation and just do a bunch of work myself. I would say, I see this really interesting angle, we should take a look at it. More often than not, the reception I got was, yeah, take a look at it. The more I did it, the more comfortable I became. The more I did it, the more people trusted me, and the more space I had. It was an iterative process that took time. It took a little bit of initiative in the beginning to get comfortable doing that. As I said before, you also have to exist in a culture that allows you that space. I happened to be at a place where people were receptive to me offering those ideas. Were there times when people said, no, we've already thought about that, thank you very much, we don't need you to look at that? Sure. And in those instances, I listened. But I always took a shot.

Khurram Naik: Taking a leap from the certainty of partnership at an established firm to launching your own, there's plenty of reasons I think it was de-risked. It's not like you're just winging it, no idea whether you could launch a law firm. You had lots of reasons you thought you could. But still, there's a risk, the comfort and status of being at Quinn Emanuel versus launching your own. From a staffing perspective, from a financial perspective, what was the basis of taking that leap?

Silpa Maruri: There were a few different things. The folks I was partnering with are people I have the utmost respect and utmost faith in. David Elsberg is a tremendous lawyer and a tremendous talent. And Rolo is also just an exceptional lawyer and an exceptional talent. I've worked with both of those folks for years and years. I knew the three of us together would be able to do the work, bring in the business, and create something really exceptional. I fundamentally have faith in the fact that great lawyers will get hired, because that's what we do. We sell our legal services, and both of those lawyers are too exceptional not to get hired. That was a piece of the puzzle.

Silpa Maruri: The other piece was, I also had faith that they were going to build something good for associates and good for lawyers to work at. Not just a place where everybody is financially secure, but also a place where I could really be proud to come into work every day, because I knew we were creating the environment we wanted to create from a mentorship perspective and from a cultural perspective in terms of giving associates great opportunities. That has borne itself out, because the firm really is doing exceptionally well. More and more matters are coming in the door every day. I think that is because the market really understands the value each of us as individual lawyers has, and also the absolutely exceptional talent that exists at all different rungs of the firm, even today at close to its inception. Every single partner we have is an exceptional stand-up lawyer and an absolute monster intellectual talent. That is also true among the associate ranks. I've been exceptionally impressed by every single person I've worked with here. So the market understands, the market sees the work we're putting out, the market sees what we're doing, and I think the thesis is really bearing itself out.

Khurram Naik: If I remember right, your name partners were at Selendy Gay, and Selendy Gay is largely a number of ex-Quinn Emanuel lawyers. At the time those lawyers left to form Selendy Gay, had you thought about joining that firm?

Silpa Maruri: I hadn't. I was at a very different point in my career, and for a lot of different reasons that didn't make sense to me. This made a lot more sense to me in terms of the folks doing it. David and Rolo together were a different package to me than the folks at Selendy. I respect Selendy as a firm. They're a very good firm. I don't have anything negative to say about them. For me that wasn't really the right fit.

Khurram Naik: So you, David, and Rolo are the name partners. Why are there three name partners, not two or four? What is it about the three of you? What's the division of labor? Why is it the three of you?

Silpa Maruri: You could ask that question at any firm, except at some firms everybody who's a name partner is deceased because they've existed for that long. The reason is because the three of us are senior, have the experience, have the book, and also bring the right maturity to bear on the direction of the firm. That's not to say every single partner isn't valuable. We have three other partners, Michael Duvivier, Vivek Tata, and Jared Rocco. Each in their own right, they are absolutely exceptional talents. But they're a little bit earlier in their careers.

Khurram Naik: What's the division of labor between the three of you? How do you function together? What are your individual strengths as partners, either as firm administrators and managers or as litigators?

Silpa Maruri: Right now the partnership is small enough that a lot of the decision making is collective among the partners. That might change once you're massively bigger, because once you're massively bigger as a partnership, that becomes a less functional model. For now, most of the decision making is actually collective among the six of us. There are pockets of areas we've carved out for particular partners to be in charge of. For example, we have a partner who deals with some of the management of tax-related decisions. Those offices are largely occupied by folks who expressed an interest in wanting to be in charge of a particular area and who have strengths related to that area.

Silpa Maruri: We also have a CEO. Her name's Josette Winograd. She's great. What is wonderful about having a CEO is that the lawyers focus on the lawyering, and she does a lot of the more business-level decision making. Obviously the partnership has a very heavy say in the high-level things, but there's a lot you have to do to run a business on a day-to-day level, and fundamentally a law firm is a business. We would be lost without her.

Silpa's decision to leave the security of a Quinn Emanuel partnership and build something new echoes what Vishal Shah shared in his episode about going plaintiff-side and launching his own firm, including how to research the opportunity, pick your partners, and design the culture you actually want to work in. Listen to my conversation with Vishal Shah.

Khurram Naik: When you're forming the firm, did you figure out how to structure all this from scratch, or did you have any blueprints from other firms? How did you come up with even the most initial stages of forming a firm?

Silpa Maruri: David had a body of experience because he had done this at Selendy Gay. He had worked on forming a firm in the first place. Josette also had some experience because she came into Selendy Gay relatively early, in the early days. Both of those things were very helpful, because they had a wealth of experience I didn't have when I started at Quinn. It was a very well-established firm. Then there was the body of experience we had just because we had already been partners at other law firms. A lot of law firm administration is something you see on a day-to-day basis as a partner. You see how the accounting works. You see some of the more functional aspects of the firm work. We had that body of experience to bear.

Silpa Maruri: It frankly didn't hurt that a number of us, including myself, do a lot of breach of fiduciary duty and corporate governance-related disputes, because we have a bit more of a business mindset in terms of how to set things up. We also had advisors who helped us along the way in particular areas where we needed advice. What has been surprising to me is not the complexity, it's actually how in a lot of ways simple the model for a law firm really is. Fundamentally you sell legal services. You're not making anything, you're not producing anything, you're not extensively relying on any third-party supplier. It's actually a much simpler business than a lot of other businesses. You hire the right people, and then you sell their services. We had to navigate recruiting. We had to figure out how to bring the people whose services we would sell in the door. But that value proposition actually turned out to be easier than I thought. A large part of that is going back to the question of why Rolo and David. Because of who we are, because of how people in the industry know us, and because of all of the things the market already knows about us, people were drawn in. We got a number of resumes we never even solicited. People saw the press that we were opening a firm, and they started launching resumes at us, because they were so excited by the concept behind what we were founding and the people that were founding it. Recruiting has been easier than I thought it would be.

Khurram Naik: What's novel about the structure of the firm, compared to Quinn, compared to Selendy, some of the predecessors you're drawing on? In terms of structure, what's a departure?

Silpa Maruri: A few things. Number one, we're obviously smaller than Quinn. Number two, we have a completely equity partnership. There's no division between equity and non-equity. There aren't tiers of partnership. Everybody who becomes a partner is a partner, and there's no multi-tiered status. Beyond that differentiator, there's also just a general culture of mentorship. When I differentiate us from other firms, I'm not thinking of any particular firm. I'm thinking about the market in general. Market-wide, there's been a real trend towards a division between equity versus non-equity partnership. We've really stepped completely in the other direction and said, we don't want that type of division. What we want is a one-tier partnership. There may be valuable and important reasons why a lot of firms in the market have gone in the other direction, but for us it's very important to be a one-tier partnership.

Silpa Maruri: That differentiator is reflected in the overall values of the firm. We really want to foster mentorship. We really want to foster early participation in stand-up roles and strategy by younger lawyers. We think a one-tier partnership is a reflection of that. That is very important as a core ideal to us.

Silpa Maruri: Another thing that differentiates us from a lot of other firms is that we are a trial-focused litigation boutique. We are litigation only. A lot of firms out there are litigation plus corporate practice, and you'll see that reflected in their cultural norms around where lawyers sit and around how cases come in the door. We are more trial focused. We've actually been hired for a number of expedited trials, which is an area of particular specialization for us. We thrive on doing that. Whereas a lot of big firms can be clunky, can move slowly in situations where you need to move quickly, we're nimble, we're lean, and we can move very, very fast in those situations.

Silpa Maruri: Another big differentiator is just the level of talent we have. We've recruited exceptionally selectively. We are probably more selective than a lot of the big firms you can think about, because we're very intentional every single time we hire a lawyer. Every single lawyer we've hired is somebody we really think is a stand-up trial lawyer who will one day hopefully become a partner. Can I guarantee that for every single person? Of course not, because when you hire somebody, you are obviously hiring them based on the prospect of what they will do. But when we hire people, we do not hire people to fill a slot. We hire people because we genuinely believe in the talent they've showcased to us. It's reflected in the quality of what we produce. It shows when we pitch against other firms. We've frequently gotten the comment that our strategy and the level of thinking we put into a pitch vastly exceeds anything they're seeing from the other firms they're looking at.

Khurram Naik: Has anything changed about your approach to training lawyers, to associates? Is there anything different about it now than at Quinn?

Silpa Maruri: My approach is really to try from the very beginning to make sure I'm asking people what they think about strategy. Every single time we're doing something, I solicit input. Sometimes an associate coming from a different environment will be surprised by how often I do that. What did you think of this argument? What did you think of that argument? I really try to get people thinking early about the case in a holistic way rather than in a narrow way. There can be a tendency, especially in a big firm environment, for people to become the so-called expert on a particular arcane corner of the case, or to become the master of some minor area of the case. There can be benefits to that in the right type of case, but oftentimes what ends up happening, particularly with very young associates, is they don't have a real picture of the big picture. They've become isolated and start to feel not responsible for the whole case. What I try to do is instill a level of responsibility for the whole case in an associate, because that really yields a lot better work product than if they're hived off in some corner and not really thinking about the case as their own. We as a firm, and me in particular, really try to foster ownership of cases from the ground up, because it really does create a much better work product.

Silpa Maruri: Beyond that, we also try to give people experiences early on, because it develops them and it also increases their investment in a case. How much more invested are you in a case where you're going to be the one actually deploying the work product you create? You're really going to make sure that work product is absolutely excellent. There are a lot of reasons to give people opportunities early, and I would posit there are more reasons to give them opportunities early than there are not to.

Silpa Maruri: Something I've recently tried to emphasize more to people than I had in the past is also just trying to do business development from day one. It's something you'll never regret as a lawyer. It takes time, it takes additional effort. Nobody's really going to pat you on the back for trying to do that and network when you're a young busy lawyer with competing demands. But you will thank yourself later, because the earlier you start, the more you're going to realize the value of it more quickly.

Khurram Naik: What are principles of business development you use, and what are ones you prescribe to others?

Silpa Maruri: As a fundamental precept, you can't reach out to people only in times of distress. Then you're just a person they're hearing from in a time of distress. What you really need to do is foster a more rich long-term relationship with any given client, because then they're talking to you on an ongoing basis. They feel like you know them. They feel like they can trust you. They feel like you know their business. The real key to business development is continuity of contact.

Khurram Naik: What has worked for you in that way? What techniques do you use for sustaining that contact?

Silpa Maruri: For me it's pretty straightforward. Whenever I have an opportunity to reach out to somebody, let's say I see there's an article about them in the paper or some recognition they got, I send them a note. I try to have lunch with them. I try to check in with them. I try to catch up with them. That means you're staying top of mind with them when you're doing those things, when you're exercising those muscles, when you're showing a person you're paying attention to them, when you're showing a person you're paying attention to the company they work for and you really care about it. I think that makes them remember you when they're thinking about who is going to help me in this time of distress, who really cares about me, who's really going to care about my company and navigating it through this litigation.

Khurram Naik: This topic of business development is reminding me that you talked about ownership. I think that's a core principle that's clear in what you are training on, and then also creativity. Of course those two things are related. But I'd like to hear a little more about ambition, because when you first came to the firm you didn't expect to stay. You found yourself, wow, I really like these creative problems, and that really is my primary motivation here, not necessarily the money. So what role did, when did you discover your ambition?

Silpa Maruri: I was actually probably pretty ambitious from day one. That might contradict what I said about, I didn't know if I was going to stay there on a long-term basis. When I came in, I came in with an open mind, which is to say I came in open to the possibility that I would really love a law firm environment and open to the possibility I would really thrive in one. Because I came in with that mindset, I also came in with a mindset of, I'm going to do everything I can to really succeed in this environment and to really make the most of it. What ended up happening was I actually realized working hard was very rewarding to me. At the same time it was also supported by the ambition to get the best opportunities, because the harder you work and the higher the quality of your work, the more useful it is in terms of lobbying to get an opportunity to take a deposition or to pitch yourself to do an oral argument. Those things fed one another. I felt an ambition to get really quality experience, and that ambition forced me to do really quality work. Doing really quality work led to more opportunities, which fostered my enjoyment of my job, fostered my ambition certainly, and also fostered my development. These things are all interrelated. It may sound kind of cheesy, but your attitude can really shape your experience of a space. Having a positive can-do attitude on a lot of things actually made the work really, really rewarding for me.

Khurram Naik: When you think about your new firm, are there other firms that you admire?

Silpa Maruri: Of course there are other firms I admire. I admire Quinn Emanuel. I think it's a great firm, which is proven probably by the fact that I've done so much of my career there. But I don't necessarily know we're trying to exactly replicate one other firm. We're trying to build something different here in a lot of different ways. One way I mentioned is this one-tier partnership, which is a very important value to us. Another is creating and fostering a real environment of mentorship. What we really want to be is a firm that produces the highest caliber, highest quality work, truly premier, and also at the same time does it in the mode I'm describing in terms of having this very equitable partnership and building a positive firm culture. Our hiring standards are very high, because we really want to be a truly elite law firm. We don't ever want to be so big that we are hiring people to fill a space. We will inevitably grow because the demand is there for our services and the associate interest is also there. We repeatedly get interest from the highest caliber attorneys. We really want to create something that's in a class of its own, both in terms of the quality of work product we produce and the quality of the services we provide, and also in terms of the culture. We want to be second to none in terms of the culture we create for our associates.

Khurram Naik: When you think about the kinds of work you bring in, you mentioned you have an edge in expedited trials because of the nimbleness of your firm. How do you think about the kinds of work you want to bring in, whether it's plaintiff, defense, high-grade contingency? How do you think about that portfolio of work in terms of the other criteria you have about culture and quality?

Silpa Maruri: The expedited trials have been great from a cultural perspective, because every single lawyer we hired is somebody who has expressed a genuine interest in trial work. That's what we do. So the expedited trials have been met with a lot of excitement from our associates, because that's exactly what they want to be spending their time doing. It's a real chance, especially for the younger associates, to get very, very quick experience in what a trial looks like. For example, I just first-chaired a trial about two weeks ago that was an expedited arbitration that literally went from pleading to trial within about five weeks, which is absolutely rapid fire by anybody's standards. Every single person in the room said it was essentially the fastest they'd ever gone. It was an exceptionally rewarding experience for me, because I love trial work. I've done a lot of trial work. This was frankly the fastest I'd gotten to trial in any case ever. But it was also a really great experience for the associate who was helping us on the matter, because he got to do everything you do in a normal litigation, but he got to do it over this span of six weeks. He saw the life of an entire case over the course of five weeks. That was a very important learning experience, and one I don't think he'd trade for anything, because when things are happening that quickly, when you look back on it, you can really see how the joints fit together.

Khurram Naik: How do you figure out a mix of work? Hybrid contingency, plaintiff, defense. How do you think about that?

Silpa Maruri: We right now probably have more defense-related work than plaintiff-side work. We do have some plaintiff-side work. We have a mix of both, because both of those things are important from a business standpoint and from a cultural standpoint. The defense-side work is great. The contingency-fee-based work is also great. It presents some real opportunities to get younger attorneys' experience, which is very nice. But we honestly are able to do that even on the defense-oriented cases. From a firm practice standpoint, all of us as litigators have litigated on both sides of the v, so we're very nimble at doing both. I, for example, was the lead on the Dell class action, which was a billion dollar settlement we got from Michael Dell and Silver Lake related to a stock-for-stock exchange that happened in 2018. That was a contingency-fee case. It was a great opportunity, and it was really wonderful because the associates who worked on that case got a lot of really significant opportunities. It also set really important precedent in the state of Delaware and the Chancery Court, which is obviously the preeminent business court today. There are lots of reasons why we want to support a contingency-fee practice. It'll never be everything we do. It'll always only be a piece of the puzzle.

Khurram Naik: It sounds like a theme I was hearing about the launch of your firm is that it's come together more easily than you expected. You expected some challenges, but there have been some great tailwinds. What are some of those tailwinds? You reference the market. What are some market tailwinds you think you're capturing?

Silpa Maruri: No one can deny this year has been the year of the litigation boutique. There have been so many litigation boutiques that have launched this year, and there have been so many that have launched just recently. The real reason you see so many litigation boutiques is because there's a demand for them. People aren't necessarily completely satisfied with the big firm model of, here's a case, it's massive, we're going to put some number of associates on it, and those associates, some of them are going to be very high value, others of them are going to contribute less value. Then we churn the case. It's very expensive and we get to a result. A lot of people are turning to litigation boutiques because, fundamentally, A, what you really hire when you're hiring for a matter is a lawyer, you don't hire a law firm. Nobody really hires a law firm. And B, a lot of these litigation boutiques have a leaner model, where they can create the same value, but they won't necessarily staff the case in a way that doesn't make sense. For us, we hire only people we think are superlative. A lot of times we can do the same thing with three or four lawyers that might take eight lawyers at another firm. We have that brain power, we have that talent Marshall.

Silpa's emphasis on early opportunities and mentorship for associates, and her belief that young lawyers are consistently underestimated, reminded me of my conversation with Lora Krsulich, who as a first-gen lawyer at Susman Godfrey talked about finding her voice and what it took to build trust as a young litigator. Listen to my episode with Lora Krsulich.

Khurram Naik: It sounds like the firm has been even more successful than you expected. With that in mind, what has changed about your initial plans for the coming year? What's changed in terms of ambition or scope?

Silpa Maruri: We're probably going to hire a few more people than we thought we were going to hire. Right now we're at about 20 lawyers. We may hire a few more, because, like I said, both dimensions are met. One is we just have a steady stream of work. A lot of people are hiring us for a lot of different matters. The other piece is we have a lot of interest on the associate side. There are just a lot of people who have really expressed genuine interest in coming and working here. Those two things in concert lend themselves to hiring a few more people.

Khurram Naik: What are you most excited about on a year time horizon for your practice or the firm?

Silpa Maruri: It was really rewarding for me to first-chair that trial. I'm grateful to have had a lot of really amazing experiences as a litigator. I've done a lot of trial work, especially over the last few years, including the trial I just mentioned and a few other trials I had while I was at Quinn. What I really look forward to is getting another opportunity, getting the next opportunity to do more trial work, because that's what I really love spending my day to day doing.

Khurram Naik: Thanks for sharing your story. It's super impressive, your rise. It's been really helpful to break down the components of that. I certainly learned a lot about practice, and I think other people will have some great practice tips here as well.

Silpa Maruri: Thank you for having me.