Khurram’s Quorum – Ep 022: Nimesh Gupta on moving from biglaw to bigtech to startups

Nimesh Gupta is the founder and CEO of Briefly, a legaltech generative AI company building software for the RFP and proposal workflow inside large law firms. Before Briefly, Nimesh went from patent litigator at Townsend (now Kilpatrick Townsend) to a business operations role at Apple, then to the founding team at TopProspect, then to founding the sales video company OneMob in 2014, then to running a late-stage secondary investing fund — and now back into legal tech.

I met Nimesh through a mutual friend, and we hit it off — our patent litigation backgrounds overlap, and his career has been an unusually deliberate sequence of jumps in and out of the law. In this conversation, we get into the role therapy has played in his professional development, why he sees the difference between litigation and sales as the difference between telling people what they have to do versus exploring what they want to do, how he sized up which industries to build in, and what generative AI is about to do to the way law firms respond to RFPs.

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

Top Insights

Below are the highlights of our conversation:

• Therapy as Emotional Regulation, Not Self-Discovery: Nimesh frames therapy as a structured way to widen the gap between feeling something and reacting to it. The three-step loop — identify the feeling, sit with it, then decide whether to align with it — has reshaped how he handles cold-email rejections, supplier pushback, and partner meetings. The point isn't to suppress emotion. It's to depersonalize the other person's behavior long enough to respond from intent rather than reflex.
• Litigation Tells, Sales Explores: Nimesh's clearest formulation of why he left the law: litigation is about telling a counterparty what they have to do, anchored to precedent and orders. Sales is about exploring what someone wants to do, anchored to their incentives. Litigation skills (finding sources, marshaling evidence, building to a conclusion) transfer to sales as a competitive advantage — but they aren't enough on their own, because the strongest persuasion makes someone want what they would have had to do anyway.
• Status Is a Contract to Be Unhappy: When Nimesh told his firm he was leaving for Apple, partners asked him when he was going to figure out what he wanted to be when he grew up. He chose happiness over status — and then noticed that every time he was about to make a non-obvious move (EE to law, law to Apple, Apple to startup, founder to investor, investor back to legaltech), the same chorus of "why are you doing this?" reappeared. He's come to read that reaction as confirmation he's onto original thinking rather than consensus thinking.
• Sell to the Incentive You Can Name Out Loud: Nimesh's sales approach with law firm chairs, CMOs, COOs, and CIOs is to surface their motivation explicitly and check it: "It seems to me this is what's important to you — am I right or am I wrong?" That overt frame replaces the standard "I'm a former entrepreneur, here's why you should buy" pitch. It only works if you're willing to be told you're wrong, which is itself a filter on who you should be talking to.
• The Data Moat in Legal AI: Nimesh's bet for Briefly is that the firms and tools that win in generative-AI-driven legaltech won't be the ones with the slickest models — they'll be the ones who capture data inside the firm that no one else has access to. RFP responses are a rich, repeatable, mostly non-billable workflow with proprietary content sitting in scattered places across BD, marketing, and practice groups. The win is helping firms gather and structure that data, then layering AI on top.

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Full Transcript

Khurram Naik: Nimesh, great to see you. And I've only just learned the proper pronunciation of your name, so thank you for correcting me.

Nimesh Gupta: Awesome. I've mustered up the courage in the last decade to correct people about the pronunciation of my name, so I appreciate that. It's kind of sensitive because we're both South Asian American males, and when you come from a country that's a part of the world that's thousands of years old, with dozens of languages and all kinds of histories, it takes so much to learn about each other's names. I feel compelled to be like, oh, I should know everyone's name and how it's pronounced — this mastery of an entire part of the world. But it's a very complicated part of the world. And even in the US there's tons of names. Some names from the South you don't hear in the North. There's all kinds of names that people aren't familiar with, so I try to show myself a little grace.

Khurram Naik: I feel like a lot of South Asians or folks with difficult names are subject to the Starbucks test. When you go to Starbucks, are you giving them your actual name or not? And if you are, how much anxiety do you have about them pronouncing it a different way? A lot of folks, their names have this deep — I don't want to say trauma, but everyone has a story with their name. For those who have a name that isn't able to be pronounced well, when they were younger, it likely was pronounced in a way they didn't want, or that they accepted. Anytime it deviated from how it should be pronounced, it caused anxiety, either in the form of embarrassment or otherwise.

Nimesh Gupta: To close the loop on that, my wife is Indian, and she pronounces my name the way it actually should be pronounced in Hindi. My name is an Indian name and it's pronounced Nimesh — the E is an A sound. So she calls me Nimesh. On my end, I grew up with people calling me Nimesh the other way, so it's this very interesting dynamic. I've grown an appreciation of people's names and really asking, hey, what do you like to be called?

Khurram Naik: One of the earliest chapters of How to Win Friends and Influence People is about saying people's names. Dale Carnegie really believed in the fundamental, primal aspect of someone's name and how important it was. I think you're onto something. It's something that gets overlooked a lot, but there's a big trend toward people getting it right and taking the time to slow down and understand each other better.

Nimesh Gupta: I love that book. The way I described it in our show is, if you can understand the impact your actions have on people, you'll win. And winning is relative — it means different things to different people. But even on the name comment, if you indicate to someone that you know their name by mentioning their name, that has a particular impact. If you understand the impact you have on another person, you can likely get what you want in various situations.

Khurram Naik: There are two aspects of you and your career I really want to get into. We talked about the importance of therapy in your professional development, and you've also talked about sales and what makes for effective sales. I'd like to pick up with therapy though, because it's something that's very under-discussed, and something you and I have talked about before. Tell me about the impact therapy has had on your professional development, when you first started, and the genesis of it.

Nimesh Gupta: I've always been naturally a reflective person — meaning, taking a step back to observe what has happened. I don't think, however, that I really applied that analysis through any kind of structured lens. One reason I wanted to do therapy was to get a more structured way to approach my reflectiveness. I had also just left my company, and the fallout wasn't ideal — or, there was a fallout, and it wasn't ideal. I was trying to process a lot of the emotions that occurred during that time.

Khurram Naik: Can you just say which company, and what time that was?

Nimesh Gupta: That was the company I ran from 2014 to 2021. It was called OneMob, and it was a platform that enabled sales reps to record videos of themselves and send them to prospects as a more effective way to engage. We raised money from Salesforce, from Cisco, and a whole host of angel investors. That's the company I'm referring to. I'd heard a ton of great things about therapy. A lot of my more successful friends — and success I'd define as folks who had achieved professionally what they wanted to but also had a peace of mind to them — those folks had suggested therapy. So I embarked on this journey to find a therapist. I narrowed down who I was looking for to someone who had experienced things similar to me as it related to childhood. A lot of what I remember from childhood is racism, frankly. It was not a diverse area. So I wanted someone who was also a first-generation Indian American, because I felt they'd be able to empathize with a lot of the racial and cultural aspects I was exposed to. I started therapy in 2021 and I've been going since.

Khurram Naik: Where did you grow up?

Nimesh Gupta: I grew up in Milpitas, California, in the Bay Area. I spent the majority of my childhood there — public schools for elementary, middle, and high school.

Khurram Naik: So you're in therapy, you found someone who's Indian American with some shared experiences. What did you discover about yourself?

Nimesh Gupta: I think I discovered that one of the most important things I wasn't doing was regulating my emotions. To me, therapy is the ability to help you regulate your emotions. Regulating your emotions, at least to me, consists of three things. One is being able to identify a particular feeling you're having. Two is being able to sit with that feeling. And three is figuring out whether you want to align with that feeling or not. Typically the period between feeling something and reacting to that feeling is very short. What therapy does is widen that window. You can now inject a period of time between when you feel something and when you react. If you're able to inject time between feeling and reacting, then you're more likely to act in ways that are in line with your true self, as opposed to acting from pure emotion.

Khurram Naik: I'm really curious about the last part — deciding whether you want to align with the emotion. My own experience with therapy gave me this concept that you don't have to identify with your feelings. You can feel a feeling and say, I am not that feeling. I'm curious for you — what is that process like? What's actually involved in deciding whether you want to align with an emotion or not?

Nimesh Gupta: Let's walk through an easy prototype example. You're driving and you get cut off. You're not happy about it. Prior to therapy — and I wasn't necessarily a hothead in that regard — the immediate reaction is yelling at that person, even though they can't really hear you, hoping they see you're angry. And then either continuing with that stream or cutting them back. So you get mad and you do something about it. If you're mindful about regulating your emotions, when someone cuts you off, first you say, hey, that kind of sucked. You're acknowledging that you feel frustrated. Second, just try to sit with it: it's not an ideal feeling, but it's okay to have feelings that aren't ideal. And third, in terms of aligning, you ask: what do I need to do to be okay with this particular feeling? For some people, including myself, when you have an emotion you feel you have to do something — some retaliation, something to make yourself feel better. In the car example, that means cutting that person off so you feel better. But what I do now is accept that it was frustration, and also realize that what that person did has nothing to do with me specifically. A lot of the third piece is removing the personalization from someone else's actions. When that person cut me off, it wasn't about me. It was actually about them. The next layer is not feeling the need to denigrate that person and say, oh, that person did this because they suck. It's more like, okay, this happened. It was completely independent of who I am. I don't know what's going on in their life, but as a compassionate human being, there's probably something. It made me feel frustrated. I felt frustrated, and now I'm going to move forward.

Nimesh's three-step loop — identify the feeling, sit with it, decide whether to align — echoes how Patti Burris described turning fear into focus and freedom in her episode. The same mechanism, framed differently. Listen to my conversation with Patti Burris.

Khurram Naik: Great example. Have you noticed anything change for you professionally? On the subject of personalization specifically — every company involves sales. Does that mean you don't personalize sales objections now?

Nimesh Gupta: I've realized that the same way I personalize things is the same way other people personalize things in their head. Part of my job right now is doing some light outbound — reaching out to potential buyers about my idea — and you always receive that one or two emails in caps: "Please unsubscribe me from this list" or "This has nothing to do with me." It does sting a bit. But now, versus before — and look, I'm not perfect, sometimes I lose my cool, it's also a function of where my headspace is at that given time — I'll say, yeah, it feels a bit shitty that someone is talking to me that way, but it actually has nothing to do with me. I try to understand: what did it have to do with that person that caused them to send such an email back to me that wasn't polite? For me, sales is understanding that as humans we personalize things, and understanding what is personal to certain people and what isn't. And focusing on identifying that — through talking to them, understanding which posts on LinkedIn they've engaged with, what their commenting style is — so that I can better relate to them when I do reach out.

Khurram Naik: Are there top of mind things you've learned feel more personal to some people than others? Some aspects of your professional well-being where you're like, maybe it's how people perceive that I'm intelligent or financially successful or skillful — what are the things you've discovered about yourself? What do you feel the most sensitive around?

Nimesh Gupta: That's a good question. I think — and I don't want to speak for what other people are thinking — but I think everyone wants to feel important. Feeling unimportant is very confusing. The challenge is that everyone has a different way of interpreting what importance is, and it's typically related to an insecurity they have. We all tend to optimize on what we don't have. When we say, oh, that person's lucky, everything's going well for them — what we're doing is taking something that's hard for us and maybe easy for them and saying, okay, well, their life is easy. But we're not taking into consideration the things that are easy for us but hard for them. For example, I played sports growing up. Sports were kind of my jam. I played soccer my whole life. Soccer is a team sport, and team sports require the ability to understand various personalities in real time. So you can get along with your teammates, empower them, and work together to achieve a goal. I think soccer is one of the best things a child can do to teach them to be more empathetic and have higher EQ. And I have an identical twin brother, which is its own thing. Those two combinations — a twin brother and team sports — meant I never really found it challenging to develop new friendships. Because I was empathetic, and I had a brother who was a good icebreaker. So being able to make friends has never been super challenging for me. When I'm looking at someone else, I don't optimize for that. I assume, well, it's easy for other people to do that too. I say all this because everyone wants to feel important, but importance is defined as the thing that is super hard for them — am I overcoming that? Am I getting validation that that piece is not hard for me, or that I've made a lot of progress? So understanding what is important to someone is very key in connecting with them, and understanding that what may be important to them may not be important to you. Projecting your interpretation of importance on others is typically a losing battle.

Khurram Naik: Part of what you're saying is it's important to understand your strengths. There's a concept I've heard that's really helpful for me. What happens so much in our professional life is that we compare. I've seen it with lawyers all the time. I'm part of the South Asian legal community, and you see a literal chain of people saying, okay, I'm jealous of that person. One person says, oh, I'm jealous about this person's success. And the next person says the same about somebody else. The chain goes on. So I'm as much part of that as anybody else. Something that really helps me is asking, would I replace every aspect of my life — who my spouse is, my interests, all those things — with that person's? Every aspect. I'll caveat that with the well-known psychology finding about endowment — you assign inherent value to the things that you have. So maybe that's part of what's driving this from a frame, but you can harness it for a positive sense. So part of what you're talking about is understanding the trade-offs across all of us, and that helps avoid feeling personalized or hurt by disparities on any one dimension. But I don't know if I caught it right — were you also suggesting that part of what we're trying to do professionally is shore up our weaknesses? Because you came from law, where you have a certain skill set, and a system of hierarchy that's well known. And then you stepped out into the business world, which is much more chaotic. You took a certain skill set and challenged yourself to pick up another. Is it doubling down on strengths or trying to shore up weaknesses, as far as personal and professional growth go?

Nimesh Gupta: Thanks for connecting the dots. Quick comment on what you said about being willing to trade your entire self with someone else in order to compare fairly — I completely agree. We may both have listened to Naval Ravikant. He talks a lot about that specific issue. Just an awesome philosopher, even though he's a tech entrepreneur. Having that frame of mind inhibits the mind from going into the realm of comparing, because it reinforces that comparisons are very arbitrary. They can be dangerous, and they can be used strategically to motivate you, but when you're really trying to pull slivers of specific people's lives and convince yourself they're somehow happier or better than you, it's dangerous. On the second piece, I feel it's not necessarily a matter of shoring up your weaknesses. It's understanding that everyone's fighting their own battles. When you're communicating with someone in a potential commercial relationship, you're trying to understand what battles they're facing — not to manipulate or take advantage of them, but to understand their intentions and how evolved they are in their thinking, without judging them. There are some people who don't care to do the work and better themselves from an emotional standpoint. That's something I've learned. It gets complicated when you have family members or people you're stuck with who are in that camp — that's a whole other podcast episode. But I think it's really understanding: who am I selling to, and what's motivating them, and trying to show them that you understand their motivations without judging them. That's been the approach I've taken. I didn't take that in my first company because I didn't do therapy. But now I sell to execs at law firms — chairs, equity partners, CMOs, CIOs, COOs — and what I try to do is figure out, okay, what are their incentives, and communicate to them directly and overtly: it seems to me that this is what is important to you. Am I right or am I wrong? And structure the conversation around that, as opposed to saying, "Hey, I'm a former entrepreneur, now I'm back in legal tech, here's why you should buy from me."

Khurram Naik: How does that process of persuasion — appealing to someone's interest and what motivates them — compare to your experience as a patent litigator? Litigation is this adversarial system, but you're trying to get things done, and so often litigation ends in settlement. Ultimately the two parties are trying to resolve this dispute in some form. How does the process you just described — selling software, growing these companies — compare to the skills you developed in litigation, in that adversarial system?

Nimesh Gupta: That's a complicated question. I don't want to answer it by stereotyping or generalizing the practice of law, specifically litigation. I was a patent litigator for close to four years. One reason I started losing interest was the lack of the people skills involved. Litigators are some of the most charismatic people I know — but in the law, especially in litigation, you have this fiduciary duty to your client over and above anything else. That is confusing for folks who are really trying to help others, because they need to do what needs to be done to help their client. That's their job. If they don't, there are malpractice implications. What I'm describing is — yes, I'm still a fiduciary to the company I own. But there's a subtlety, and maybe you can help me suss this out, that enables you to focus more on the human aspect. You see this in your job too, right? As a business owner helping people create their livelihood, you still have a fiduciary duty to your business as the primary shareholder, but there's more of a human emotional component outside the law than there is inside it. Admittedly, that's a generalized statement. When you're a fiduciary to a company that's paying you a lot of money to do something, and the context is already adversarial, I don't think it's conducive to really get down and adopt the framework I'm describing.

Khurram Naik: I think there's another resolution. So much of litigation is telling your counterparty what they have to do. Anything around sales — I shouldn't use the phrase "the real world," but anything outside of litigation — is about exploring what people want to do. In litigation, you're bound by this format of pointing to precedent as the basis for your position, or pointing to a court order as the basis. It's not an appeal to your counterparty's interest necessarily. The legal system isn't resolved through that other dimension. If you're interested in anything else in the world outside of litigation, you realize the limits of that skill, which is very powerful. I don't want to diminish it — it is useful in other contexts, because litigation is a way of providing evidence, laying out a set of facts, and that naturally leads to a conclusion, and then maybe you tie to policy or law. That formula is a legal formula, and finding original sources that support your position — all of those are skills incredibly valuable in sales. You have a competitive advantage because other salespeople aren't trained that way. But it itself is not enough to really be successful in persuading other people, because ultimately the most successful persuasion is people wanting to do something rather than having to do it.

Nimesh Gupta: That's interesting. I really think this is case by case. I don't like going up against people. I like collaborating with people — and they're not mutually exclusive. There's a lot of collaboration in litigation. I was actually pretty competitive growing up playing sports, but I'd rather bring someone along for the ride than do something myself. Selling software now, there's a very collaborative theme. Hey, I have something that's going to help make you more efficient and/or help you make more money. Let me understand your incentives, then let me best present my offering to you in a way that aligns with what's important to you, so you can test out whether my stuff does what it says. That's how I look at it. And that's why I don't feel like the typical salesperson. I'm not super aggressive. I have a very hard time pinging people multiple times within a five-day period to see if they've gotten my message. I think all of those things are necessary, and there's a ton of talent and content around that. This may be in line with where I'm at in life and what's important to me, but I just want to understand who I'm selling to and why what I'm selling is going to make their lives better. That said — and I'm being brutally honest with myself — sales is about momentum. It is about pressure. It is about being aggressive in certain areas. I'm trying to identify my weaknesses and incorporate them into this kind of mindfulness-related selling.

Khurram Naik: Glad we laid this foundation, because now I'm interested in spending some time on the facts of your journey, to provide some context and narrative for what your path has been out of law. Let's talk about that first transition. There are so many lawyers I know who haven't served themselves or others well by saying, hey, I'm interested in something beyond law, I just don't know what that looks like. You were a patent litigator at Kilpatrick — a great firm — and then you went to Apple in a business operations role. That seems like a completely different role, and nothing that you'd probably encounter in the course of being a patent litigator in a big firm. How did you come to that role?

Nimesh Gupta: I leveraged my electrical engineering background and was slotted into patent litigation. I practiced at a firm called Townsend, which was acquired by Kilpatrick — I still call it Kilpatrick Townsend, but that merger occurred after I left. I don't have any family members in the law. I didn't know that 100% of your grade in a law school class is based on the final exam. I went in in this very naive way. As a side note: I remember one of my first trials, I was out in Tyler, Texas. The only colored suit I had was a black suit. I didn't have a navy or a charcoal suit. I didn't have my father telling me that black suits are typically worn to funerals, you don't go to court with them. I walked into the courtroom in Tyler and I had my black suit on. I immediately noticed that everyone else had a charcoal or navy or tan suit on. So I took my jacket off because I was super embarrassed — but that was actually a huge faux pas because you weren't supposed to go into a courtroom without a jacket on. A partner came literally running to me saying, hey, what are you doing? You have to wear your jacket. I remember that was — I don't want to say it was a low point, but it was a really big realization. I'm in this new thing I never knew existed and I don't belong. But it was also the birth of this courage in me, where I was proud I'd gone this far and done something different. I'd hit a low point, but I was there. I mention that story because it was actually kind of the genesis of me leaving the law too. I practiced for four years. I got a lot of opportunities. As a BigLaw associate I took 14 depositions my first year, which was unheard of. I worked for one partner — he and I got along really well, he took me under his wing, took me to all of his depositions, one day said hey, you're going to take this deposition, coached me. He and I are still good friends. He's 20 years older than me, just a really good guy. I did two trials. And I started realizing I couldn't see myself being an executive at a law firm. The people who were considered successful at the firm I was at were just not folks I could see myself being, if I did become them, being happy. That was the first time in my life — I'd graduated law school with $160,000 in debt that I paid off myself. The first four years I was just heads down earning money. I finally got to the point where I had enough to step back and say, is this what's making me happy? I realized it wasn't, for a few reasons. One, I didn't think there was a lot of collaboration involved — it was very adversarial — and I started seeing myself take that home to my personal life. I was arguing with my girlfriend at that time, trying to outsmart her with various arguments, and I'm like, this is just not me. Two, I just frankly didn't think I was a good writer. There are some litigators who really know how to write a brief. I don't. I felt that was always a weakness I didn't care to or try to overcome. Anytime I'd get assigned to write a brief it would cause a lot of anxiety because I knew I wasn't the best person to write it. Today, with ChatGPT, it may be different — but that just didn't resonate with me. After making that realization, I took the patent bar and started prosecuting patents, and realized even more so that I didn't want to be in patent law. Prosecution is a different animal. You can make a lot of money, it's a stable lifestyle in certain regards, but it wasn't exciting to me. So I stepped back and said, what do I want to do? My twin brother — who also was a litigator who left the law at that time — had started a venture-backed tech company. He was kind of one of the motivating factors for me to realize you could actually do something other than the law. Most people outside the law perceive lawyers as very capable and intelligent, but — generalization — they also don't perceive them to be business-savvy. So if I wanted to do something outside the law, I needed to bridge that perceived gap by developing business chops. I made the decision I wanted to leave the law, and I started searching on LinkedIn under jobs for a JD. I just searched jobs that had JD as a requirement. This was around 2010. There were surprisingly a lot of jobs that were looking for an MBA or JD, and the actual company mentioning that confirmed their interest in hiring JDs in a non-legal role. There were some non-practicing legal roles like contracts manager that seemed appealing, and I applied to a couple. But there were other jobs that had JD as a requirement, and Apple at that time was looking for such a job. It was called business operations manager, and what you would do is ultimately be the general manager for a particular SKU of an Apple product — responsible for making sure all of the components that go into a particular product get delivered to the OEM where it's put together, in China at that time. You're responsible for spearheading the effort of the 400 or so suppliers that supply those parts, both delivery timing and the commercial arrangement between Apple and those suppliers, making sure the price of each was negotiated. I saw that job, I interviewed with 19 different people, I got the job, and that's how I left the law and broke into the business side.

Khurram Naik: What's interesting about that role is that it required a JD, but something I haven't heard you talk about is status. I didn't hear from you the story of, when you're at the firm, the status give-aways were important to you. So much you were kind of a bit — you were a status-y lawyer, you didn't know the rules, that wasn't part of the appeal for you. I know with suits or whatever it was, being a trial lawyer, maybe status was totally not important to you. Now of course being at Apple has its own status, has a lot of cash, all of that. But was that dimension at all a barrier for you? Because I've noticed this is true for many lawyers — the status dimension is a hard pill to swallow. As a lawyer at a big firm you're working a million hours, and you're paid well, but the status is really nice too. People don't realize they're giving that up even when they go in-house, for instance. Was that a dimension for you at all, or just totally not even something you were attracted to in that move?

Nimesh Gupta: That's a good question. When I did tell folks I was leaving for Apple I was met with a lot of bewildered looks, even some chuckles. I remember one partner saying, "Hey look, at some point you have to figure out what you want to be when you grow up. You're 30 years old, what are you doing?" I remember at that time I chose happiness over status, if that makes sense, and realized also that status, at least for me, was very relative. Status is based on consensus thinking. I've kind of adopted this through most of my life — being accepted by someone based on consensus thinking is ultimately confirming that you're unoriginal. Very strong statement, I know, and it can be interpreted in many different ways. But when I was an EE, in the fifth year — I double-majored in EE and economics — my last year I decided I wasn't going to do EE, I was going to go to law school. A lot of my EE peers had a similar reaction to the lawyers when I was leaving law: why, what are you doing? To me, that confirmed I was onto something. I'd rather be onto something based on original thinking than do something that's just confirming what someone else is looking for. Again, very loaded comment, could be interpreted in different ways. But that move I made from EE to law, then from law to business, is a similar move I made from Apple to starting a company, then from a company to raising a venture fund. That's a big part of me. It's also what I try to teach my kids — be confident in yourself enough to look past what someone else will think of you if you do things in a certain way that they're expecting you to. I still seek validation from many people. It's there. I don't think it'll ever go away. But I find that when I do get validation from people I've been yearning for, I'm on cloud nine for a few minutes, then I say, huh, so this is what I was trying to get? I got it. Is this something I actually really wanted or not?

Nimesh's framing of status as a contract to be unhappy mirrors what Sunny Kim described in her episode about quitting BigLaw and owning your own narrative — the same recognition that the status reward loop has a ceiling you eventually have to walk away from. Listen to my conversation with Sunny Kim.

Khurram Naik: It reminds me of Naval's framing of desires as the contract you make with yourself to be unhappy. Status is exactly that way. If you agree that you have some status, you've just handed over a source of happiness to other people. You're literally not in control of that form of happiness. Obviously we all value status in different forms, it's not something we ever fully extract ourselves out of. But what you said reminded me of that. I'm also curious — you've made these transitions from engineering to law, from law to business. There's a concept from Scott Adams, the Dilbert guy, about success. His thesis is that to be successful you don't have to be in the top 5 or 10% of something. You have to be in the top 80% of three things, and then string them all together. For him: I wasn't the best office worker, I wasn't the best cartoonist, I wasn't the funniest guy, but I was a pretty funny guy who worked in an office who could draw an okay cartoon about office politics. That's the basis of the success. I think it's a useful framework. So much in law, particularly, there's a selection bias of the people who made it through that system. They stuck it out, and by definition they were the ones who stuck it out, the ones left standing. It's very easy for them to turn out and say, well, why didn't anybody else do exactly what I did? For a couple of reasons. One, if you've got that Pascal's triangle with balls bouncing through it, they're the ones who happened to end up on the outer end among commonly qualified balls, for randomness of markets and practices and so on. But that aside, I think it also underestimates how much opportunity there is in trying new things, in not sticking with any one thing. Curious how you think about the tradeoff between sticking with a path versus making moves and the benefits of learning new skills that mitigate the costs and risks of those moves.

Nimesh Gupta: There's so much gold in what you're saying — I want to reverse this and ask you a ton of questions. But for me, it's: I've committed to evolving. I've committed to an evolution of others and an evolution of myself. Professionally, one reason I did leave the law was because I didn't think there was that collaborative component. The other was that I didn't think I was the best at it. In today's world, from a livelihood standpoint, you either have to be really, really good at what you're doing, or you have to be very passionate about it so you can continue to learn, put in the hours when others aren't, and ultimately become a master in it. I know there are some really good lawyers. I didn't think I was a good lawyer. I thought I was average. Now, my expectations are higher than I think the average person's. I'm not going to claim I was a good lawyer, and that really gave me a lot of anxiety, because this was supposed to be the profession I'd stick with. So I asked, well, what am I good at? A lot of what I was good at I thought aligned with business — being able to talk to people, relate to people, have a very collaborative mindset. Those skills I thought were more conducive to starting my own business, or at least being someone in a non-legal role. That turned out to be accurate. I went into a business-related role, and that set the stage for me to start a company. Even when I was running my company, OneMob, in 2014 — or at the end of it — I started feeling I wasn't the best person to run that company. I'd been there for about seven years, a lot of my thoughts were stale, I was coming up with the same ideas over and over, there wasn't a lot of newness in what I was thinking. So I stepped back and said, okay, I got to change. I got to course-correct. This actually maps back to my childhood. My dad was an electrical engineer, studied EE undergrad and got his master's in it, worked for big companies his whole life, and was always subjected to multiple layoffs. He was a really smart guy. He's retired now. But he didn't really play the politics right. He didn't have an interest in it. Instead, he coached my soccer team for like 20 years and was the commissioner of the local league. He'd literally volunteered more hours than he actually worked, which is incredible. I always had that fear, from seeing what happened to my dad, that I had to course-correct and be in an area where I felt I was either passionate or really good at it. That's what I'm doing now. I'm a legaltech entrepreneur who's a former BigLaw lawyer but also former SaaS founder and former SaaS fund manager. I feel — and I say this with all humility — that that combination puts me in a select group of people to really give this a shot, specifically selling to large law firms. That's a function of being humble enough to know areas I'm not good at, or industries where I may have lost relevance.

Khurram Naik: We can come back to the company you're founding, but as a preview: what is the skillset you got at Apple, in this huge company in this operations role? Operations is a very different skillset than you get at a law firm. What did you learn from a big-company operations role that's impacting your role today?

Nimesh Gupta: One thing about the law: when you practice at big firms, even though they are big firms, you're typically on small teams. Litigators especially are actually quite entrepreneurial — they don't know it because they have a lot of autonomy. They call a lot of their own shots. Yes, there's a senior partner navigating, but once a senior partner has trust in you, you kind of run your own show. You run your meetings however you want, you develop your strategy at a high level. A lot of my entrepreneurial capabilities were developed in those small litigation teams. When I went to Apple, I realized I wasn't able to — and this is specific to Apple in 2010 in operations, I can't speak to other large companies — I didn't feel I was able to flex my entrepreneurial skillsets, being able to call my own shots and do things the way I wanted. It was the year of the iPad, after the iPhone came out three years prior. There were 10,000 people who wanted to work at Apple. I knew if I didn't do things a certain way, there would be someone else who'd do it better. And that's what happened. I left the company and the market cap has 10x-ed since. Whether I was there or not wasn't going to make a difference. It was a $300 billion market cap company at that time, and now it's a three trillion dollar company. That made me uncomfortable, because I knew I was expendable. Maybe this maps back to what I perceived my dad's career to be like. I knew this wasn't going to keep me in demand.

Khurram Naik: What about operations specifically as a skillset? We've talked about sales, but how does operations help a growing software company? How does that skillset impact what you're doing today?

Nimesh Gupta: Operations — and this is not to marginalize it — is extreme project management. As a litigator, you have that. That's why I think anyone who's graduated law school and practiced at a big firm can literally do whatever they want. I'm so bullish on anyone who's gone to law school, because of the skillset you learn in your formative years — analytical skills, how to ingest a ton of information and package it into outlines for tests. You develop the ability to project-manage. On the operations front, it was managing so many different topics and associated data for those topics. I felt I had those skillsets having gone to law school, and being an engineer before helped as well. The work wasn't hard for me. It was whether the work I was doing had enough of an impact to make me indispensable. I felt very fungible. I could be taken off this project and someone else moved in and the company would do well. My gut read was right — that's what ended up happening. I left and they didn't have any problem filling my role and the company did really well. So to answer your question about operations: I don't think there's a specific skillset that as a litigator you can't have for operations. The only difference really is from a people-skill standpoint — understanding you're not going against someone, you're collaborating with someone. I caught myself, for example, negotiating with suppliers thinking it was an adversarial relationship when it wasn't. They're trying to make money, you're trying to get a product on time and fit it into your budget. You can be friends. It's all good. I quickly realized that when I joined Apple.

Khurram Naik: So then what was the path from Apple to being on the founding team at TopProspect?

Nimesh Gupta: I wasn't a founder there — I was a founding member, which is a fancy way of saying you're one of the early members. At Apple I realized I had no impact. For me it didn't work. There are a lot of people who thrive at Apple, who love Apple, and Apple's done very well. I knew I wasn't going to be relevant there. At that time though, I was at Apple, so I had the business chops. The ultimate goal was: could I have left the law and started a company right away? That's what my brother did. I found I was unable to do that because one, I didn't have an idea, and two, I didn't have my business chops. So now, after eight or nine months at Apple, I knew I didn't want to stay. That was another complicated decision because mentors I was talking to said, "Look, you just left the legal profession, now you've got this job that took 19 people to interview from. Do you really want to leave it? You're going to be kind of a job-jumper." But I stuck to the principle — something felt off about my relevance in the organization, both in terms of whether what I was doing had an impact and whether I was passionate about it. That was the litmus test. I started cold-emailing different startups that were backed by Andreessen Horowitz. They were a well-known firm and have now crushed it. I listen to anything Marc Andreessen puts out. He was writing his blog back then. So I started reaching out to a number of startups backed by Andreessen Horowitz, and the initial outreach was, "Hey, I'm interested in applying to this business development manager job." No one was responding back to me, even though I was a lawyer working at Apple. As you can imagine, that was really humbling — I'd left the law and Apple and now I'm cold-emailing these startups and no one's responding. So I had to change my approach. I started looking at these companies and asking, if I were to go start a business line there, what would it be and why would I be the person to help build this? TopProspect at the time was a social recruiting company. They wanted to help in the referral process — they felt people had robust social graphs on LinkedIn, so how could you find people in your network who were looking for jobs and help refer them to other jobs? I said, this would be awesome for the legal vertical. I know a lot of my friends who want to join other firms. I could refer other people and maybe get a cut of the hefty fees the industry makes. I reached out to the CEO telling him exactly that idea, and he responded and said, "That's cool, let's talk." We hit it off. I actually still stay in touch with him today. He's a mentor of mine, super smart guy. He sold his first tech company in '99, then started a hedge fund, then went back and started TopProspect. We met once a week for about two or three months. I was really interested in what we were doing. He didn't have a position available because they were about to raise their next round. He couldn't commit to hiring me, but there was so much velocity. I actually left my job at Apple without a full-time job at TopProspect. That was super scary. But I just really saw how much I enjoyed what we were doing and how much I was learning. A month later, he hired me on full-time.

Khurram Naik: I'm going to ask you about risk and making leaps another time. But tell me — what made you move into the next role from there? What did you learn about yourself at TopProspect that made you want to take on a different role?

Nimesh Gupta: Two parts — procedural and substantive. On the procedural front, I learned a lot about venture-backed C-corps. What is a C-corp, what is a Delaware C-corp, what are common shares, what are preferred shares, what's this thing called a 409A valuation, how do you recruit talent, how do you build product, how do you sell that product? TopProspect was a crash course in everything about venture-backed C-corps, from a founder who'd done it before — a winner who'd done it before. He brought a finance-related perspective as well. It was a great learning experience. I learned the language that is spoken at startups. Substantively, I learned how to double down on my scrappiness, but in a formal way. I've always been scrappy, and this maps back to litigation days — you hear stories of litigators finding that one document in the haystack, or talking to that one witness no one else wanted to or thought of talking to. That's scrappiness. At startups that behavior is rewarded. So I learned to double down on my scrappiness, to believe in my intuition and act on it. That's what I really took from TopProspect. Then I got to a point where I knew I was ready to start my own company. We had raised our Series A and it didn't look like we were going to raise the next round. I had an honest conversation with my CEO — who again is still really close to me — and said, hey, I think I'm ready to start a new company. And that's what I did.

Khurram Naik: So you launched OneMob. How did you find your CEO for OneMob?

Nimesh Gupta: He and I — I went to Santa Clara undergrad, he went to Santa Clara for his master's, he'd worked at Salesforce for eight years. Super energetic, just a really nice guy, very charismatic. I enjoyed hanging out with him. We started OneMob together. It made sense — it was sales technology integrated with Salesforce, so his background at Salesforce was a big reason the company worked. He and I ran it for about eight years. He's actually still running the company now. He'd run a company before, which was really helpful — this was going to be the first company I was a founder of.

Khurram Naik: What was the legacy of that firm for you? Seven years of one venture is a long time. What made you stick it out so long?

Nimesh Gupta: Being a founder of a venture-backed tech company is exciting, for a multitude of reasons. You're actually building. Building a technology company has so many facets — you need an engineering team, a product team or product manager, designer, etc., plus the sales piece. You're in Silicon Valley building it, so you're around so many other founders trying to build their own companies. It's a contagious, surreal type of environment where you're talking to other folks and they're building stuff, and they're commiserating with you. I feel like you see one side of founders — hey, everything's going well — but a lot of founders are very real with their challenges to other founders. It created a sense of belonging that I kind of never had before. It was just fun. I was learning. No day was the same as the previous day, and that was invigorating. But toward the end, days started becoming very similar. The novelty of my thoughts was fading. That's when I knew I'd have to make a change.

Khurram Naik: What was going to be different in the next role?

Nimesh Gupta: Doing something where I was learning and I was uniquely positioned to do it. While at OneMob I'd started investing pretty heavily. I invested in several early-stage companies, then late-stage companies. There was an arbitrage opportunity in 2018-2019-2020 — and this is no longer the case — to invest in companies about to go public by tender offer or share purchase, then sell them after they went public and the lockup expired. There were variations where you could buy forward contracts for companies that didn't allow transacting. That strategy has faded because of some regulatory issues. At TopProspect and OneMob I did all the legal work and most of the corporate work, a lot of which had to do with purchasing shares and stock purchase agreements. That turned out to be a valuable skillset when purchasing late-stage shares from employees, because I understood how stock transfers worked and what was necessary to navigate board approvals and so on. I leveraged my background in investing, the fact that I'd been a founder, and started a fund investing in these types of companies. The story made sense — I was attuned to what was going on in the startup ecosystem, so I had a unique viewpoint of some of the companies I'd invest in, but I also had the procedural chops to make these deals occur. That's how I raised a fund.

Khurram Naik: Through your fund or your personal investing in early-stage companies, what's been your most successful investment?

Nimesh Gupta: Without naming a name — it was a company I got in at a $3 billion valuation, and they went public at a $30 billion valuation. A 10-bagger, as they say. That created some liquidity for me, which was great. I also — and this is a whole different animal, you have experience in this — I invest a lot out of my IRA. There's this concept of a self-directed IRA. It's what Peter Thiel supposedly used to invest in Facebook. I built the base capital for that IRA through investing in options, which is something my CEO from TopProspect taught me how to do. From that capital, I then started investing in late-stage companies. One company I think was my best investment — I got in at a $3 billion valuation, and it went up to $30 billion, and then I exited at a $15 billion valuation. It did sting that it went down by half, but you can't be greedy.

Khurram Naik: When you say investing in options, you mean options trading?

Nimesh Gupta: Yes. Nothing super crazy — I would just buy a bunch of LEAPs, long-term call options. No straddling or anything like that. But as you know, options are force multipliers for a particular return, and they can also be negative in certain situations, which I've experienced.

Khurram Naik: Do you still trade options?

Nimesh Gupta: I don't. I have kids now, and they keep you busy. It's risky. Especially in the market now, there's just so much uncertainty. Making money trading options today is a lot more complicated and difficult than it was three or four years ago.

Khurram Naik: I'm curious about how going from founder to investor and back to founder — how has the lens of an investor changed how you approach your new venture-backed startup?

Nimesh Gupta: A couple of things. A big part of success for a startup typically is receiving some type of funding. There's a school of thought that says if you can bootstrap your business, that's amazing, and there's truth in that. But typically, to build a technology company, you need to invest a lot of resources upfront in R&D, hiring engineers to get it off the ground. AI may change that — who knows. But fundraising is going to be an important component of your startup. As an investor, I never raised a fund to invest in early-stage companies — I invested early-stage with my personal cash, and the fund was for late-stage. I want to be clear: I'm very aware of not making myself seem like an expert in something I'm not. That's problematic because there are many people who put themselves out as experts in areas where they're not. But I learned what investors look for. For example, at my stage — my company is about six months old — they want to know whether this company can be a billion-dollar market cap company or above. If they were to invest at the seed round, they'd invest at anywhere from a $10 to $20 million post-money valuation. They want to know there's significant upside. Some people say investors just need to see a 10x return, but typically at the earlier stage, because they're taking more of a risk, it's more like 40 to 50x. If you get in at a $20 million valuation and the company becomes a billion-dollar company, dilution aside, that's a 50x return. So you need to convince them that your vision is large enough to get there, but you also have to show some path to get there — revenue projections you've actually thought through, mapping out to a billion-dollar valuation. Typically your companies are valued at 10x revenue, so you need to show that you can be a $100 million a year revenue company in order to be a billion-dollar company. You need to prove you can hire talent — why is someone going to come work for you as opposed to a ton of other companies, especially top-tier talent? You also have to show you're self-aware enough to take feedback. A lot of founders come to the table and it's clear they will not take feedback. These are things I've learned sitting on the other side of the table that I'll be hyper-aware of when I go to raise around.

Khurram Naik: Is there something about financial reasoning that changes how you think about a company, its operations, how you value certain sales channels — anything else about financialization as a skill that impacts decision-making or strategy?

Nimesh Gupta: There are a lot of entrepreneurs who just want to build cool shit and go sell said cool shit to people, but don't have an idea of how much it costs to make it, then how much to charge for it, and if you do charge for it, how much that brings into the bank. It's not to denigrate those founders — some founders just know how to build stuff, and they shouldn't be doing the other thing. I'm a big believer in doubling down on your strengths as opposed to improving your weaknesses, with caveats. But if you come from a finance background, you can quickly figure out, does this business work? And convey that to a potential capital partner. I say, look, my burn is $50K a month right now. That comes out to $600K–$800K a year with additional overhead. In the first two years I'm likely going to spend a lot more than I bring in. By year three we're going to start increasing focus on sales, and by year four or five I can be profitable. A lot of these investors just want to know you thought about that. At later stages it's very different — you have sophisticated investors who can pore through a P&L, build their own bottoms-up models, not rely on your projections. But at this early stage they just want to know you're self-aware enough to have thought about this. That's even more valued in a post-2022 era, where the market's taken a hit and the public markets are focused on profitability.

Khurram Naik: So you're building out a legaltech company now. What made you want to return to law? You escaped BigLaw, you found startups, selling recruiting software and sales software. Why return to the legal industry?

Nimesh Gupta: This is going to sound really weird, but I really feel at home in the legal industry. I have a lot of love for lawyers. I love interacting with lawyers. Lawyers are some of the smartest people I've ever met. I felt like I really gained expertise in being able to relate to lawyers — practicing lawyers, executives at law firms, former lawyers. It's a skillset of mine. As I was thinking about what I wanted to do next, because I'd deployed my fund — the natural progression would have been to raise a second fund or do something else. Fund two wasn't necessarily primed to be raised because our investment strategy wouldn't have been conducive to where the market is now — there aren't too many secondary opportunities that are worthwhile. So I started talking to different folks and realized that generative AI is here. I know that sounds cringeworthy, but I've been in tech for a while, and the way things are changing now is unlike anything I've seen before. I became really intrigued with how it would affect the legal industry. The way I think about it: there's the buy side of legal services — companies procuring legal services — and the sell side — the actual lawyers rendering those services. On the buy side, you've seen quite a bit of innovation, with the Ironclads of the world, with legal ops functions emerging at these companies. Technology has been sold to companies on that side. On the sell side, the law firms, that's where technology hasn't been sold too much. There are leaders in the space, but generative AI has opened the door for law firms to re-underwrite a lot of the technical systems they have or need. Given that I'm a former lawyer who practiced at an Am Law 100 firm, it gives me a unique opportunity to be a trusted advisor to law firm execs — to bridge the gap of, okay, generative AI is here, what does that mean, educate them on my perspective, and then hopefully sell my software to them.

Khurram Naik: What were industries that didn't make the criteria? What were you looking for in an opportunity?

Nimesh Gupta: One thing I really — this was a humbling process — I wanted to do something where I felt a lot of other people couldn't do it. Where I knew I was going to be someone different. Competition is high, and as I said earlier, you either have to be really good at what you're doing or really passionate. With this, I feel like I'm checking both. I feel like I'm really good at selling SaaS software, because I just came off running a SaaS company and then investing in SaaS companies. And passion-wise, I really like folks in the legal community. I enjoy talking to lawyers. Yes, some lawyers fit the bill — I had a call the other day and the guy was really hard-nosed, and I'm like, come on man, you can open up, I'm not gonna bite. But who knows what was going through his day. I tried not to take it personally. The other area I would have ventured into was investing, but I frankly don't think I'm the best at investing. I'm good, but there are a ton of other people who are better, and it would have required me to dig deeper to find my differentiation. I just wasn't interested in doing that.

Khurram Naik: When you mention differentiation — how did you size up the competition and the industry? What role does competition play? Some people say competition is good because that means this is a growing market category. Others say, hey, I want to be the only one doing X. How do you think about those two schools of thought?

Nimesh Gupta: It's interesting because here, AI is only like six months old. Yes, OpenAI has been around for six or seven years, but ChatGPT — everyone's had their aha moment with ChatGPT. It's something we haven't seen before. Everyone's kind of equating this to, well, last time we had crypto and crypto wasn't real. I think anyone who's used ChatGPT is like, wow, this is incredible. So when it comes to competition in this space — not even law, but generally — everything is being rethought. Competition is relative right now. We're in this unique opportunity for the next year or so where I don't think you can go wrong at least immersing yourself in AI, because you'll learn something that will make you relevant going forward. Competition is still being established and developed. The incumbents are saying — you've seen Salesforce's ad with Matthew McConaughey, where he's like, well, who is this sheriff in town? They're positioning it as you need grown-ups to manage AI. But there are so many newer players that are going to emerge that for me, I was thinking about it more not from a competition standpoint but saying, hey, there's pure greenfield opportunity in AI, and in legaltech one area is even more greenfield in terms of selling to law firms. Anyone I spoke to before I started this said, why do you want to sell to law firms? It's super hard to do. And I agree with that. But I think I have the capability to sell to law firms. It takes a certain type of person. Let me build something around the pain point that my co-founder and I identified and sell that to law firms and see where it goes.

Khurram Naik: What is the competitive advantage you have? How do you think about the strategy? You've talked about your background. What about the business itself — are there network effects, flywheels? How do you think about properties that make the business stronger over time?

Nimesh Gupta: We're an AI-first company — specifically a generative AI-first company. My co-founder studied computer science in undergrad and graduate school with an emphasis in AI. He minored in linguistics, because he knew different types of areas he wanted to study with AI. He's been on this generative AI journey with OpenAI from the beginning. He's an expert at this. He's super patient — he explains it to me in a layman's way. His expertise plus my background as a former lawyer makes a good team to sell AI-first technology to law firms.

Khurram Naik: But the business itself — is there a property where, once law firms work with you, that gives you some moat around distribution or network effects? What about the business itself that gets stronger over time? Amazon's famously got a flywheel where as we get more products that gets more consumers and more consumers means more sellers. How do you think about properties that make the business itself stronger over time?

Nimesh Gupta: We have specific viewpoints on what would differentiate us. One is the ability to gather data within the law firm in a secure-first way. It's those players who can gather data unique to them who I think are going to win. Without going into it further, data is going to be a huge moat. We've spent a lot of time thinking about what data we have that other folks cannot. A lot of this ties back to law firms understanding their own data and having their own data strategy, which is going to be a separate issue and need. So data is going to be a huge factor for us. By data, I mean being able to help law firms gather relevant data, and then focusing on specific data that enables our technology to process and analyze.

Khurram Naik: I love that. We've gone for a while and finally explained what the business is. So data, what data — what is the business? What does Briefly do?

Nimesh Gupta: We believe there's a wealth of data in actual legal proposals. We are finding different ways to suss out that data and improve associated workflows in the responding to legal proposals at law firms. We've created a platform that processes legal proposals — RFPs, etc. — and enables firms to respond to them faster and better.

Nimesh's bet on generative AI as the moment law firms re-underwrite their technical systems — and his framing of AI as something to use to gather and shape proprietary data — echoes how Neel Chatterjee described using AI as lawyer-adjacent rather than lawyer-replacement in his episode. The strategic move is the same; the use case is different. Listen to my conversation with Neel Chatterjee.

Khurram Naik: Something that really does resonate with me — if there's one thing law firms have, it's how much time they spend in the office. People say, okay, yeah, this may go a while or so, 2,000 hours, that's just 40 hours a week. But people don't have an understanding of all the other work that you do, including non-billable work. There's also a fairness issue — there's a lack of transparency, because it doesn't count toward the business. There can be inequitable distributions of who does that work, and that impacts your bandwidth for other work. So the thesis makes a lot of sense to me. If you were — so in the short term, law firms aren't looking to use generative AI to reduce the amount of billable work they do, unless maybe they're on a fixed fee. But they're certainly looking to reduce non-billable work, particularly if it's writing in general. That all makes a ton of sense. Are there any other legal tech companies, generative AI or otherwise, that you've found really interesting?

Nimesh Gupta: Just to close the loop on what you said — every lawyer or anyone who's been at a law firm has the frustration of having to respond to an RFP, whether it's a lawyer filling out the legal analysis section or folks in BD or marketing having to corral information from different constituents to meet a deadline. It's a huge pain point. We're excited about innovating in that field. From a legaltech standpoint focused on AI, I think the jury's still out, no pun intended. You have folks like Casetext, which was acquired by Thomson Reuters, and a few other startups innovating in the practice of law. I think the leaders will be folks who incorporate AI into their existing offerings. Incumbents may win on the company side, and we have to be mindful of whether they would win on the law firm side too. On the company side, you have Ironclad — they've gained a lot of trust through their contract lifecycle management process. Can they incorporate other workflows to make processes more efficient for their customers? I'm actually bullish on companies like DocuSign, which have always had some type of legal implication. I don't know what their AI strategy is, but they're kind of like Salesforce for sales — DocuSign is that for legal departments. Everyone uses DocuSign. They could do some stuff there, but I haven't really seen anyone emerge as the leader, and a lot of that is because all of this is brand new. There are a lot of folks thinking about it. The other caveat: when it comes to legaltech innovation historically, the total addressable market for legal has always been not that big. Ironclad kind of pioneered going after it and creating a large company around this. I'm not sure what their recent valuation is. I know they raised at a three- or four-billion-dollar valuation, but that was 2021. I don't know how much R&D effort is being put into innovating in legal — I know more people are than before, so by virtue of that there's going to be more competition. But no one's really come to mind as winning right now.

Khurram Naik: If somebody is a newly graduated lawyer at a big firm, what's your advice for how to think about the changes in the coming years?

Nimesh Gupta: On the work front, try to have as much agency in what you do as possible while still not rocking the boat. Think of yourself as an owner of a business when you are on that small litigation team. Develop courage to call your own shots. Don't always look for the playbook — try to create the playbook. A lot of folks are really good at following directions and rules, but AI is going to commoditize that function, because AI can follow rules. So have a mindset of: I know there's a certain type of system I need to adhere to, I know there are rules I need to follow, but I'm going to have agency to develop my own thought processes and my own playbook. The second part is being brutally honest about what work you're doing and billing out for that can really be done by AI — because eventually that's going to happen. You can't hide under a rock. If there's something you're doing right now that you know you could have stuck into ChatGPT and done it faster, it's eventually going to be exposed. I'm not saying stop working on that. You don't have to go blog about it and expose it. But have a real talk with yourself and say, okay, this response to this cease-and-desist letter I just charged $10,000 to a client for — I could have inputted the actual cease-and-desist letter and asked ChatGPT to write a response. Be real with yourself. Those are the two things I'd advise young lawyers on.

Khurram Naik: That'd hit me pretty hard if I were a first-year associate planning years to come. I think that's a good spot to pause. We'll pick this conversation up another time. Thanks for sharing your story. I'm so glad we started with the therapy and intentionality aspects, because that's been a theme throughout, as has the risk-taking and boldness component. We've covered a lot.

Nimesh Gupta: I had a lot of fun. You're great at this. Your ability to listen and ask specific questions to unpack topics is not easy, and it's an art. I really look forward to seeing where you take this. Thanks for having me.