Khurram’s Quorum – Ep 049: Louis Tompros on creating adjacent bets

Khurram’s Quorum – Ep 049: Louis Tompros on creating adjacent bets

Judge Richard Linn first pointed me toward Louis Tompros more than 13 years ago, telling me my entrepreneurial approach to breaking into patent litigation reminded him of one of his former clerks. The story the judge shared stayed with me: Louis had created his own chance to argue at the Federal Circuit by stepping into a pro se inventor appeal he spotted on the docket. It became a presidential opinion. This episode has been a long time coming.

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

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

Top Insights

Below are the highlights of our conversation:

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

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Full Transcript

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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