Khurram’s Quorum – Ep 041: Rakesh Kilaru on White House decision tools and “trial by subtraction” for high-stakes cases
Rakesh Kilaru is a partner at Wilkinson Stekloff. In a few years, Rakesh has resolved headline-making disputes, including defeating a $21 billion challenge to the NFL’s media model, defeating the FTC’s challenge to Microsoft’s $68.7 billion acquisition of Activision Blizzard, and negotiating an innovative settlement over the NCAA’s compensation rules. And he's barely over 40.
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."
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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.