Khurram’s Quorum – Ep 040: Dai Wai Chin Feman on optionality and business development for career control

Khurram’s Quorum – Ep 040: Dai Wai Chin Feman on optionality and business development for career control

Dai Wei Chin Feman is Managing Director and Corporate Counsel at Parabellum Capital, a litigation funder. This conversation gets practical in breaking down the system Dai Wai has built for career success: a diversified portfolio of relationships, skills, and value-creation mechanisms.

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.