I sat down with Paul Grewal, Coinbase's Chief Legal Officer, who has done something few people do: he left a law firm equity partnership to become a magistrate judge, then left the bench he loved for Facebook, then left Facebook for a crypto company that still had to explain itself to his parents. What I wanted to understand was the reasoning underneath those jumps, and Paul walked through each one with a candor I did not expect.
Top Insights
- Paul took a 91% pay cut to become a magistrate judge, and the financial side was the easy part; the harder adjustment was emotional, going from the center of a law firm to the youngest, least-known judge in his court.
- Before he makes a move, he asks whether the upside is merely incremental or whether it could be two, three, or ten times better, because only an asymmetric payoff justifies the risk that it does not work out.
- The skill he was least prepared for as a judge was managing the emotions in the room, calming a witness or reassuring a lawyer, not parsing Ninth Circuit precedent.
- He argues the best trial advocates and the best people on social media share one trait: curation, knowing the two or three things to say and leaving the rest on the cutting-room floor.
- When lawyers ask him about a career crossroads, he tells them to set aside what they enjoy and ask instead what they are genuinely, second-nature good at.
- The regret he optimizes against is never trying the different thing, not failing at it; he has been passed over for a district judgeship and a general counsel role and counts those as the cost of taking swings.
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Full Transcript
Khurram Naik: This is Khurram with Khurram's Quorum. My guest today is Paul Grewal, the Chief Legal Officer at Coinbase. This is one of those interviews that builds and the pieces all come together. I think even people familiar with Paul's story will walk away with a deeper understanding of what makes Paul tick and the first-principles reasoning he uses professionally. Here's Paul. Great to see you. Thanks for joining.
Paul Grewal: Great to see you as well. Thanks for having me.
Khurram Naik: So I want to hear about, you know, we talked last time about your workout routine. And I know you said you've been very consistent with your workout routine for a number of years. But I'm curious, what is your workout routine today and how has it changed over the years?
Paul Grewal: Yeah, it may not be very compelling, but I've tried to be at least consistent. And exercise has been a big part of my life for a long time. These days I'm trying to do a mix of cardio at least three days a week, mix in a little weightlifting. And then, you know, if I can squeeze in a round of golf or a walk or a bike ride, it's been a pretty good week for me.
Khurram Naik: Is it usually first thing in the morning?
Paul Grewal: Yeah, for me, like, if the workout doesn't happen at the beginning of the day, it just doesn't happen. So I'm generally a pretty early morning person; it kind of always happens. So I like to just pop up out of bed, don't even have a cup of coffee, and just get right to it. And then once I'm done, you know, I feel like it's really time to start my day at that point.
Khurram Naik: Yeah, love that. And so has it changed much at all over time? Has it just been kind of the same for an hour?
Paul Grewal: Yeah, it has changed. I think as I've gotten older, I've probably gotten better at being more consistent. I mean, to be super clear, earlier in my career, early on in life with little kids, and managers and senior partners and others who didn't necessarily attach the same importance to my workout routine in the morning as I did, you know, things sometimes fell apart. But I think I've gotten more consistent with it. And then the other thing is, you know, as the body ages, a couple things happen, right? Like, you get slower. Hopefully you don't get too much weaker. But, you know, I've certainly placed much more emphasis on just maintaining my physical strength and my endurance rather than, you know, literally sweating over whether I'm going to shave 10 seconds off my 5K time or whatever the case may be.
Khurram Naik: Yeah. And is there anything else you do for wellness in general, like, you know, how else do you tend to yourself on a daily basis, weekly basis?
Paul Grewal: Yeah. I've dabbled with meditation. I certainly do a fair amount of yoga. I've never been sort of a dedicated mindfulness-practice kind of guy. I have not been one who is a regular at religious services. So a lot of the things that a lot of people do that I think work really well for them have never really caught fire for me, even though I've always been a dabbler, always experimenting with something new, always trying to find a new angle to get a little peace and calm in my day, especially before things start to get much less calm and much less peaceful before things are done.
Khurram Naik: Well, it's interesting because I think a number of people that I've talked to who know you well have observed about you that you are very even-keeled. Something that makes you special or different is that you maintain a pretty even keel and don't tend to get too elevated. And, you know, I know you're a former litigator. I think you know how elevated some people can get in that space. So how do you do that, then? If you don't have some sort of mindfulness practice or something similar to that, what is your approach or principles, like, how is it that you're able to maintain this more or less even keel?
Paul Grewal: Yeah, I like the word "elevated." I'm going to have to start using that, because in my experience, particularly in trial and litigation generally, it's more agitated and elevated. I think for me, part of it's just, you know, my nature, the way I grew up, the way I've kind of approached things outside of the practice of law, it's probably given me a bit of center and focus. And at the same time, you know, I try to eat right, I try to sleep right, try to exercise, as we've just talked about, in ways that I think also literally lower the blood pressure, lower the temperature, and hopefully allow me to, you know, focus on what needs to be done rather than how I feel about it. I deal with my feelings later. My first priority in my situation is to figure out what we need to do.
Khurram Naik: Yeah, that's good. Well, you know, I thought that with that in mind, I feel like your story, lots of what's your story, is well known. I mean, you've got a very substantial social media following. You've done a number of interviews over the years. I think a lot of people know your story in large part. I thought this would be an opportunity to get into all the other bits of your story that I think are less known. You know, what are the other aspects of life that have facilitated the decisions that you've made? And so I thought we could maybe talk about that. So, we'll start with, I don't know, a contrarian version of your story. So maybe the jumping-off point is we'll talk about your experience. We can jump around chronologically. I know your clerkships have been important to you. We can double back to those for sure. But let's say you're a law firm partner and you're trying to decide what comes next for you. And then somehow you make a transition to a magistrate judge. Now, I think a lot has already been told, but what aspects do you think are misunderstood or not understood about that move that you made?
Paul Grewal: Well, one thing that I think sometimes gets confused, at least when it comes to my decision to become a magistrate judge in, what, 2010 or so, is that it somehow was part of some grand plan. There was no plan. It certainly wasn't a plan that was grand. At best, I had a rough sense, a nagging feeling, an instinct that I would enjoy service as a judge. And I certainly had in the back of my mind so many of the positive, formative experiences I had as a law clerk, not once, but twice earlier in my career, seeing how judges worked, what they did. But most importantly, what satisfaction they took from their day. I think that was the thing that stuck in my mind: that for all of the amazing and impressive lawyers and others that I worked with up to that point in my career, the two people who I really felt relished their day more than any other and really seemed to appreciate what they were able to do day in and day out in their professional life were the judges they worked for. And so, maybe simplistically, perhaps even naively, I thought, well, if I ever had the chance to be a judge myself, maybe I would relish my day and appreciate what I was able to do in that same way. And so that was really it.
Khurram Naik: And then, you know, you definitely had the qualifications to be a district judge. Why is it that you accepted or went for a magistrate judge role?
Paul Grewal: Because that was the opportunity that was given to me. It was pretty simple. You know, when I applied to be a magistrate judge, I want to say I was probably 38. So, relatively young, not the youngest ever, but relatively young. And, you know, for me, what increasingly became attractive about the opportunity was this idea I had in my mind, however imperfectly formed, that I could do something with that opportunity that maybe not a lot of other people had done. You know, I think in a very hierarchical structure like the federal courts, we naturally think about the Supreme Court justice as first and foremost. They probably occupy, you know, 90, 95% of our mind space; they certainly consume 90 or 95% of the conversation and oxygen in any room of lawyers. But in the lower ranks of the judiciary, there are incredibly talented people doing incredibly important work. And just as important, at least from my perspective, given incredible opportunities to be very creative, to do a lot of good for real people in real cases, but also to just, you know, expand their professional skill set and have an impact on the world in ways that I think are relatively underappreciated. And so as I thought more and more about what magistrate judges do, what I might be able to do in that role, and, you know, the opportunity in front of me became more and more attractive to me. And I cared less and less about whether it was sufficiently high enough in the hierarchy to warrant, you know, professional praise and command respect that we all, I think, want, even if we're not always all willing to admit it. So, yeah, it was really that as much as anything else. And at the same time, you know, at that stage in my personal and professional life, I had done certain things that allowed me the opportunity to change my life, change my family's lifestyle, in a way that was significant. Going from being, you know, an equity partner at a major law firm to, you know, the lowest-ranked junior judge in the federal government required a bit of, you know, financial and emotional gymnastics as well. And I was ready to do all that.
Khurram Naik: Tell me about that. I think that's really huge. And that, I think, is a major obstacle for a lot of people at every level to make decisions: you know, being able to handle a drop in comp or a change in status. How did you plan for that? Like, how did you know that you were set up? How did you know you were equipped to make that work? And what were the tangible things that you did to put yourself in that position?
Paul Grewal: Yeah. So I think, well, let's start with the financial, because in some ways that's more straightforward. That's more mathematical. You know, at the point I became a magistrate judge, I had been an equity partner in an AmLaw 100 firm. The Howrey firm no longer exists, but in its day was, I think, well respected and certainly was a place where I learned a lot about practicing law. And as a rising partner in those ranks, starting to attract clients, starting to attract really interesting cases, you know, I was at a point where, you know, I could afford a mortgage, I could afford private schools for my kids. I was fortunate enough, and remained fortunate enough, to be married to a working professional. So that provided a certain amount of flexibility as well. And at the same time, as I think a lot of us struggle with, as, you know, the income rises and as the resources grow, so too do, you know, our appetite, our taste, and our preferences. And so one of the things that I think my wife and I were relatively successful at was figuring out what mattered in terms of our cost structure, where we spent our money, figuring out what didn't, so that we were able to maintain a relatively, relatively being the key word here, modest lifestyle that reflected, you know, the way we earned and worked maybe five years before or even ten years before, even though things continued to go better and better for us in our careers. And so with that sort of mental model in mind, you know, it felt less scary for me when I was extended the offer to join the Northern District of California as a magistrate to accept it. I was prepared, I think, financially and otherwise, to take the 91% pay cut that was required in order to pursue that opportunity. And at the same time, I had a certain amount of confidence that things were going to be just fine. There were plenty of people who did just fine living on the salary and compensation package of a junior federal judge, especially with a working spouse. And so that helped. And that made it possible for me to have the confidence to take that leap of faith. On the emotional side, though, I actually found it to be a much bigger challenge, because I think a lot of people, when they think of judges, they think immediately of instant respect, instant authority, an ability to sort of clearly command a room, right, in ways that are not possible for most people. And that certainly was all true. At the same time, you know, for me, I was going from a place where I had associates, I had clients, as I mentioned before. And inside of a law firm, you really are, as a partner, the center of that universe, to a place in the court where, as I said, literally, I was the youngest, the most junior, certainly the least-known judge, not just in my court, but certainly nationally or, you know, on a broader scale. And so you had to sort of adapt to, like, oh right, this is like taking any new job. I've got to start at the bottom and I've got to prove myself. And so, you know, once I sort of put it in those terms and really treated it as no different than, you know, when you get that first job, you know, working at McDonald's or as a junior usher at a theater or whatever other situation, it just became easier for me to, you know, adapt and steel myself for, you know, that learning curve that comes with any new opportunity.
Khurram Naik: And then in that role, I mean, what were the skills that you came in expecting to hone? So maybe you can tell me about, you know, how you in fact did hone those skills. And then what were the surprising skills that you didn't expect to hone that you picked up?
Paul Grewal: Yeah, so for judges, right, like, at least as I thought about it, you know, it's relatively obvious. You have to be pretty good at understanding how to take apart a case. You have to be pretty good at analyzing complicated laws, sifting through messy, imperfect records, weighing and deliberating on, you know, credibility, determinations, all that stuff, I think, is relatively well understood. And, you know, I was confident enough that I had, at that point, enough experience practicing law that I would be able to manage that transition well enough not to make a complete fool of myself. What I think proved to be more challenging in that realm was the fact that, you know, my practice up until that point had been almost exclusively focused on intellectual property disputes, patent trials, trade secret fights, the occasional copyright or open-source software license. And, you know, day one, as a magistrate judge, I was literally, not quite literally, but nearly literally thrown out onto the bench and, you know, thrown into a criminal law calendar where I had very experienced assistant United States attorneys and equally experienced federal public defenders, all there to do their job and all expecting me to know what the heck I was doing. So there was a lot of learning by doing. And I think, importantly, a lot of humility required as to what I didn't know. And that's something that I had to embrace in a pretty direct way. But part of the job, though, where I felt like I didn't appreciate what skills were going to be required in order to be effective and ultimately successful, was managing the emotions of the moment. Right? So in any dispute in court, whether it's a fight over, you know, a software license or, you know, a decision as to whether somebody's going to spend the next 13 months awaiting trial in jail or anything else, you know, all of those situations require, I think, a certain ability to navigate some pretty complicated emotions in the room. And, you know, those emotions extend just from the parties; you know, pretty easy to understand why a criminal defendant in that situation may be a bit agitated or elevated, as you referenced earlier. But the lawyers, right, they're worked up. They've got a range of emotions to work through. If you're picking a jury, you've got a bunch of people in there who don't want to be in there for the most part. Don't understand what's happening. They're confused. They're anxious. In some cases, they're a bit nervous. And so you've got this range of emotions to navigate and manage. And of course, on day one, and from that point going forward, everyone assumes, because you're wearing a black robe, you know how to do that. Those skills, I think, were the biggest challenge for me to understand and then begin to start to learn and ultimately, hopefully, master, as much as the hard skills that have to do with taking apart a Ninth Circuit or Supreme Court precedent or resolving conflicting witness testimony.
Khurram Naik: So what were the, I guess there's two things to that. We'll start with: what are the techniques that you've learned over time? Like, how do you manage people who just have strong opinions, strong feelings?
Paul Grewal: Yeah. Well, I mentioned one thing that I think is at the root of my approach, at least my intended approach, because I fall short of this ideal every single day. I think you start with humility. I think you start with acknowledging, not just to yourself, although first with yourself, but ultimately to everyone around you, that while you know a bunch of stuff, there's a whole heck of a lot more that you don't know, almost in every case, right? And so I think that was helpful, so that everyone understood that whatever their emotional range was at that particular moment in time, I was going through my own range. And so I think it helped to level the playing field in that way. The other thing I think that was very helpful was that, you know, I've never held myself out as the smartest lawyer or the most impressive trial advocate. I've certainly practiced with, against, and had in front of me some of the best, and I'm nowhere near that. I do think that one of the things that I've gotten pretty good at over time is figuring out how to give people the comfort and the confidence that allows them to do their best work. And so whether that's a witness testifying who needs to be calmed, who needs to be assured that they're doing just fine, or in some cases corrected or directed in a way that helps them to elevate their performance, whether it's, you know, letting a lawyer know that even though their argument is going nowhere fast, they haven't lost the moment entirely, there's still a chance for them to persuade me or persuade the jury of their position. I think there are just little touches like that that help people feel comfortable in their own skin. And that's one of the things I've tried to do. Certainly I tried to do as a judge in the courtroom, but even in my current role and elsewhere, that I think has proven to be relatively effective and allows, as I said, you know, the people around me to be the best at what they're there to do, which ultimately obviously benefits everyone.
Khurram Naik: Well, I think the interesting balance that it sounds like you're striking is humility with confidence, because you also have to show, like, hey, there's a reason why you should be tuning in to that; I will help you here. And so how did you establish that confidence? How did you, I'd say, maybe avoid the outcome of, say, imposter syndrome, like, hey, I'm very skilled at IP, but I'm not really knowledgeable the way that an experienced criminal attorney is about criminal matters. How did you establish that authority and ramp up and then put yourself in a position where you have that credibility while balancing that humility?
Paul Grewal: Yeah. Well, I do think that you can be confident and humble at the same time. And I think in many roles in the law, it's really important to be both, right? Because the fact of the matter is, whether it's in a courtroom or in a boardroom or anywhere else, in most cases, people are looking at you as a lawyer, you as a judge, and expecting you to know exactly what you're doing, right? It's a lot like being in a surgical theater, right? You would, I think, be more than a little bit anxious to learn that your anesthesiologist was humble and, at the same time, lacked confidence in what he or she was doing, right? You want that one person to know exactly what to do, even if they understand that there are many other roles that are important to a successful outcome. And so, you know, from my perspective, the number one thing, I think, that helped is that I've shared my genuine curiosity in what others do. It's amazing to me how in a single day, certainly in a courtroom, but I think in many other professional settings in the law, you know, we are just also privileged to encounter, work with, in some cases work against, some incredibly interesting people who've done some even more interesting things. And I think that even if you have, you know, almost no basic or baseline understanding of what it is that a trust and estate lawyer does or why it is that an agent for the FBI pursued an investigation in a certain way, if you have a genuine curiosity and a drive to want to learn more about what they do and why they made the choices that they make, and then you should express and share and communicate that genuine curiosity and enthusiasm for their work and their path. In my experience, you know, most people, most of the time, respond very positively to that.
Khurram Naik: Yeah, like that. Tell me about, you know, on the bench, you observed a lot of the advocacy. What was the prized skill for advocacy you observed?
Paul Grewal: The number one thing that I observed that I think too few trial lawyers appreciate is that almost always the most important questions, or the most important arguments, are the questions or arguments that you didn't make or didn't pose. You know, I think of great advocacy as ultimately about curation, right? And, you know, when I think of great curation, I think of painters, or I think of musicians, who are always thinking about what strokes or notes to drop or to, you know, exclude entirely from their body of work or their piece of work. And I think for advocates in the courtroom, certainly, the very best were almost minimalist by nature, right? They figured out the two or three things they needed to ask or the one or two arguments they needed to make, and then left a whole lot more on the cutting-room floor. That was something I saw, and continued to see, that was very consistent among the greats.
Khurram Naik: I like that. So then tell me some more about, again, with this notion that we're boldly laying out the hidden story of Paul Grewal, the things that people haven't heard about. Because I think, you know, plenty of people heard about your move that I think excited, surprised, wowed a lot of people, to Facebook. So tell me about the things that people don't appreciate about that move.
Paul Grewal: Well, one thing maybe that is not easy to appreciate is that I really loved being a judge. And so I think a lot of us, when we make career changes in whatever form, right, are moving away from something we don't like or running from something that is bringing us stress or anxiety or just unhappiness. And in my case, that just was not true. I hope that I was able to communicate effectively day in and day out when I was on the bench that I really just loved the day-to-day. I loved being in the courtroom. I loved the characters that find their way into a federal courthouse day in and day out. I loved the fact that I had no real idea what I would be working on over the course of the day, just given sort of the random and tumultuous nature of most court cases. All of that was fantastic. I certainly loved the relationships I had with my fellow judges. I most of all loved and adored the relationships I had with my law clerks. So it was a wonderful experience. And so it might be quite understandable or reasonable to think, well, then why? And how could it be that you were so happy and that you were willing to give it all up? And I think for me, you know, this was now 2016. I'd been serving as a US magistrate judge for nearly six years at that point. Not nearly as long as many, but, you know, long enough to understand the basics of the job and to have done a lot of interesting things in that job. So that I felt like, you know, there were other professional opportunities that I wanted to pursue and other professional skills I wanted to acquire and develop. You know, at that point in time, I had probably written, I don't know, a couple hundred published opinions. I was very fortunate that in the Northern District of California, where I serve, magistrate judges have the opportunity to try civil cases if both sides of a case consent to the magistrate judge's jurisdiction. And I don't know, I think I was able to do something like 30, 35 civil jury trials in nearly six years, which was a pretty heavy clip. And so, you know, I'd had that experience, I think, to the degree that I had hoped for. And, you know, at the same time, when I learned about the opportunity at Facebook, when I was introduced to the team there and came to understand that what they really wanted at that point in time was someone who understood the court, understood courtroom advocacy. They wanted someone to run litigation who had seen a lot of different cases and worked on a wide range of issues. And of course, you have nothing if not a diverse docket of cases when you serve as a magistrate judge or a trial judge of any type in any federal court. It all just kind of made sense to me for them. And so, you know, as someone who was never afraid to, you know, zig and zag in my career path, it felt like an opportunity that I would very much enjoy and would regret if I didn't take. And then the other thing I would say is that, again, coming back to, you know, an earlier vein you were exploring, I had to sort of, at that point, ask whether I could once again start as, if not a junior person, a new person, in a very, you know, complicated organization. Facebook was stuffed with super-smart, super-talented people. And, you know, no one was going to call me Judge Grewal when I walked around the campus in Menlo, however much I wondered if they would. For the most part, you know, I was just Paul from Building 20 or 23 and, you know, I had my badge like everybody else. I rode my bicycle and locked it in the bike rack in front of, you know, the main campus entrance, just like every other employee. And so, you know, fortunately, having, you know, made that transition at least once or twice earlier in my career, that wasn't the big deal that it might have been for some other people. I was very comfortable, you know, leaving a role at that point where everybody stood when I entered the room, everybody laughed at every joke I made on the bench. 50% of the people who left my courtroom thought I was wise and, you know, brilliant, even if the other half thought I was the opposite. You know, I was just at that point very, very comfortable in my own skin and quite willing to make yet another change because I thought I would grow in a different direction. I think when you stop growing, you stop living. And so that was really as much as anything what motivated my move to Facebook.
Khurram Naik: Were there other roles that had the same profile? And so what was the tiebreaker that made you go to Facebook?
Paul Grewal: Well, I hadn't really considered any other role, certainly seriously, at that point. But for me, it was all of the things I mentioned about the opportunity, but also the fact that I had an instinct, even if I couldn't quite have predicted how much this turned out to be true, that the company was about to enter a very different phase of life. You know, at that point in 2016, Facebook still largely basked in the glow of, you know, our adoration for all things tech. And there was still, I think, a perhaps naive view that most of the things tech did, most of the time, were, you know, in pursuit of human progress, and that, you know, tech was a force for good. It was becoming increasingly clear, certainly by early 2016, that that view was starting to look a bit naive or simplistic. And the company was about to head into some, I think, very challenging legal issues that I would have a chance to play some role in. And so that was also super attractive to me. And, you know, I don't know, it took maybe three or four weeks after I joined the company in 2016 for that to become abundantly clear. And so at least I got that call right.
Khurram Naik: And so then, you know, again, you had a certain set of skills that you expected to gain out of the role. And then maybe there were some that surprised you that you weren't expecting to pick up. What were the surprises? What were the things that you, you know?
Paul Grewal: Well, yeah, I mean, look, at that point in my career, I'd tried a lot of cases. Not only as a trial lawyer, but at that point as a trial judge. I mentioned that I worked on a bunch of different kinds of cases. I'd had privacy, intellectual property, competition issues, you know, whatever the case may be. So I had a lot of confidence, much more confidence, definitely, that I could not only draw upon my experiences working on these different cases, but orient to new types of cases altogether that would come up, in a way that I think would be effective. What I had never done, or what I'd never done, was lead an organization. You know, as a law firm partner, you don't really lead an organization in the same way as you do in other settings such as, you know, inside of a company or in the military or elsewhere. You know, you have a group of associates that, you know, you sort of assemble on the fly, you form these coalitions of the willing that, you know, move forward managing these cases, and in a handful of them, you take the cases to trial. And then you break up the band, right? And you look for the next case or the next project and assemble a different team, even if some of the same characters repeat themselves. That was certainly true as a judge. I had a couple of law clerks. I had a courtroom deputy. And that was about it. You know, whereas by the time I left Facebook, you know, I was leading an organization of several hundred people. I had, you know, teams literally all over the world. Those were all challenges I had never taken on before and required a whole new set of skills in terms of, you know, managing that complexity, understanding what the business and its priorities were, and making sure that, you know, my litigation team, my regulatory team, my corporate team, whatever the case may be, were focused on those priorities day in and day out. I had to manage compensation and performance, you know, issues, just like any other, you know, leader of an organization inside of a company. I had never done that before. Oh, and by the way, I had to go back to a world where I had a boss, like everybody else. And, you know, I had to make sure that my boss thought my work was great. As a judge, you kind of have a boss in the form of the chief judge of your court. Maybe you can think of the appellate courts as supervising your work. But at the end of the day, you really don't have anybody who really tells you what to do or cares beyond a certain point how you do it. And so I had to, you know, adapt back to that world, or really adapt to it for the first time. And those were a lot of skills that I had to develop that were new and certainly challenging for me.
Khurram Naik: And then I think you can see where this is going with your next move. So then, you know, same thing, the move to Coinbase was, you know, a lot of attention for that. You know, it was obviously a company that a lot of attention was being given to, but it was still a remarkable move. And so what's the story that people haven't heard about the calculus in that decision to do that?
Paul Grewal: Well, look, I think one thing that was very consistent in my move to Coinbase with my move to the court, and even in my progress in my firm life before that, is that I've always been a huge believer that, you know, when the opportunity comes, when the ball crosses the plate and it's time to swing, you better be ready and you better not miss. And so, you know, I only applied to be a magistrate judge when I felt confident that I could not only do it, but do it very well. And the same was true when I went to Facebook to take over litigation and then, with time, other areas of the legal department fell to my responsibility. But in each of those cases, I was not the top dog. I was not the number one. I was not the district judge or the Ninth Circuit judge or Federal Circuit judge in my time on the bench. When I went to Facebook, I was not the general counsel. But by the time it came for me to decide whether to accept the opportunity at Coinbase, I was being asked to serve as the Chief Legal Officer. And for me, that was something that I finally felt I was ready to do, having led, you know, a complicated organization at Facebook, dealing with, you know, a whole range of super messes for the company, everything from Cambridge Analytica to all sorts of different class actions involving data privacy and intellectual property and regulatory fights with the FTC and elsewhere. You know, by the time it was time for me to step up into the Chief Legal Officer role at Coinbase, I felt like I had the grounding, I had the experience. And that all gave me the confidence to think, you know what, I'm ready to do this. And, you know, you asked about what might have been less obvious in all of that. Well, I think a lot of people, you know, when they think of digital assets or cryptocurrency, they think that you've got a group of people who are not just passionate, but maybe even fanatical and delusional about, you know, sort of the ideological or other underpinnings of Bitcoin and, you know, all the other tokens and assets that we deal with. I had none of that. I'd read the white paper. In fact, the first time I believe I read the Satoshi white paper, which laid out the thesis for Bitcoin, was when I was a magistrate judge on the bench and I was asked to review a Rule 41 search warrant from an FBI agent looking to seize some Bitcoin in an investigation. This was back in, like, 2012, maybe, maybe even 2011; it was early days. But I had not, like, immersed myself in that universe, and I was not, you know, yearning to be a part of a movement or a revolution. I wanted to help some very smart and good people do some interesting and important things. And I had a sense, once again, that this company, like my last company, was about to enter a very different phase of legal life. And I've just been a huge believer as a lawyer that it certainly is never a bad thing, and I think can often be a huge catalyst and accelerant in a legal career, to put yourself in positions where the major questions, the major fights, you know, the major opportunities of the organization are all grounded in law. Because at that point in time, you know, you will be not only an important part of the work and an important voice in the conversation, you're also going to be, I think, uniquely positioned to assume leadership. And, yeah, that was essentially what I thought about Coinbase in 2020. And once again, my vague instincts that the company was about to enter a huge number of early, messy fights turned out to be pretty true, at least if I take a look at my to-do list this morning in 2023.
Khurram Naik: So, going back to the decision to join Facebook. I mean, I think, you know, your role now, the role of resolving regulatory issues, seems to be essential to the business. Like, the overlap between product and your role is huge. And it seems to be less the case in your role at Facebook. And so what made you take the leap to Facebook, knowing that IP issues weren't at the centerpiece of the organization? What made you think that you would skill up and level up from that move? Aside from the company's trajectory, what made you think that that function would be good for you?
Paul Grewal: Yeah. Well, I actually think in 2016 litigation and regulatory issues were about to become fairly existential for Facebook in a way that wasn't true before. To my knowledge, Facebook had only had one jury trial up until that point. Certainly it was true that Mark Zuckerberg had never testified in any court case. And, you know, fast-forward just 18 months after I joined when the Cambridge Analytica scandal blew, and suddenly Mark and others were being hauled in front of Congress to account for and explain what had happened in that situation. And those were all very novel experiences that proved to be quite searing for the company. And so as it turned out, actually, you know, what was once, I want to say, a quieter function, because Facebook's always had a share of litigation and regulatory investigations, but what became a very public and strategic challenge for the company, necessarily meant that things I was working on, like helping to put the Cambridge Analytica situation to bed, or at least at rest, or making sure that when we went to trial in these billion-dollar cases that the outcomes were at least neutral, if not positive, most of the time, it meant that I would have an opportunity that I don't think I would have had five years before in the same role. And maybe I wouldn't have even today, five years later, just given how much the company has changed over that period of time.
Khurram Naik: And can you be a little more specific about how you came across that opportunity at Facebook? Did Facebook approach you directly? Tell me a little more, because it's kind of unusual for a magistrate judge, I would think, to be approached by a company. Tell me some more of how that happened.
Paul Grewal: That's pretty unusual. We don't have on-campus recruiting in the federal judiciary. It works a little bit differently than many young lawyers would probably be more familiar with. Now, for me, as I think back to it, a number of my friends who were still practicing law, very much practicing law, told me in late 2015 or early 2016 that Facebook was looking for a new kind of leader. I think the general counsel, Colin Stretch, was very forward-looking and understood quite well, as a very talented advocate and litigator himself, that he needed some additional expertise in the company, that he needed expertise in particular when it came to courtroom advocacy and strategic planning and direction-setting through some very intense regulatory investigations. So, when my friends mentioned to me that Colin, and the leadership beyond Colin, was looking for this new kind of leader for the company, the more I thought about it, the more intrigued I was. I realized I presented an atypical or unusual profile in terms of people interested in that. But if they actually came to learn my story and what I could do and what I had done, maybe they might be interested. So, at their encouragement, I reached out to Colin. We had a couple of coffees, and, just like, you know, so many jobs and so many opportunities for all of us, right, one cup of coffee led to a lunch, one lunch led to a dinner, a dinner led to a series of conversations and meetings and interviews. Before I knew it, I was, you know, hanging up my robe literally and, you know, signing up for a very different kind of life at the company.
Khurram Naik: Earlier, you referenced this concept of seizing opportunities, you know, like, hey, here it comes, you've got to be prepared for it. And so I want to kind of explore that theme in some of these other moves you made. With your friends, how did they know to come to you with that? Did you tell your friends, hey, by the way, I'm open to other opportunities, or, you know, was there something you messaged in that way? Not, like, waving a flag saying, I need to get hired, whatever, because you said you were happy. Tell me how people knew to talk to you, to tell you about this.
Paul Grewal: Yeah, I mean, I think it was really not much more complicated than a conversation or two in which, you know, my friends basically said, you seem very happy, Paul. You seem to enjoy the public service life. You know, obviously there were further potential opportunities within the judiciary available. And yet, it seems like, in a strange way, everything you've been doing up until this point in your career is exactly what Facebook is looking for or could benefit from in this new role. And so, you know, I can't say that, like, immediately I thought, oh my gosh, yes, this is the next, you know, thing I need to go do. I tend to be much more, I don't know, circumspect, incremental. And so I said, yeah, I'll have a cup of coffee. And then I'd hear more about it, and it just sort of built upon that, as opposed to, you know, maybe for some people, like, there are grand revelations, like, you know, Moses coming on down from the mountain with tablets, about what they want to do or need to do next in their professional or personal life. That just hasn't been my experience. It's been much more about, you know, seeing something that catches my eye, learning more, and then thinking through. And this is also something that I've weighed very heavily: is the upside of the new opportunity, whatever it may be, not just incrementally better than what I have right now, but does it possess the potential to be two, three, ten times better, however you define it and according to whatever metrics you use, in a way that makes it worth taking that leap of faith and risking that it doesn't work out and that you're not only not much more happy, but happy at all, and, God forbid, much less happy. So I think you have to think about, at least I've always tried to think about, like, are there those big leaps and are those big increases, however you define it, available, or at least potentially available, in a way that makes it worth pursuing.
Khurram Naik: And then, you know, with the move to Coinbase, how did that opportunity, there's the aperture, there's you, how did those two converge?
Paul Grewal: Yeah. So Coinbase was, you know, again, like, I know a lot of people talk about how, you know, they are tapped on the shoulder, or someone whispered that, you know, people are interested. Like, my process was much more pedestrian and mundane. I got a call from a recruiter, just like everybody else. And, you know, at that point in time, Coinbase was still a private company. I think we had maybe 500 employees. We now have something like 3,500 and we are publicly listed. We have been for several years. It was a smaller, more chaotic place. And yet, I think by 2020, it was clear, at least to me, that cryptocurrency and digital assets were not going away. They were not some, you know, fad or fraud that, you know, would just sort of disappear as quickly as they appeared. But this was for real. There were real opportunities with this technology and real markets to build and develop. And yet, you know, there were also very real challenges that were largely rooted or grounded in law that could benefit from someone who had spent a lot of time in the courtroom, but at this point in time also managed very complex litigation and, or rather, investigations for a major tech company. And critically, for them, someone who had, you know, at that point, learned and understood how to navigate the corporate world, you know, how to marshal resources inside of a large, complicated organization where lots of other people want and need resources for what they're there to accomplish, how to exercise influence and even maybe power on occasion with no real explicit authority. You know, these are skills and talents that I think are also critical to success. And having, you know, learned a certain amount about how to do all those things inside of Facebook, I think there was an opportunity for me to really apply those lessons in a pretty significant way at Coinbase, given that Coinbase, at that point in time, was less than 10 years old, was, you know, a generation or two earlier in its development than, say, Facebook was. And so it just made a lot of sense. And then, you know, as I went through a process that you and many others, I think, are quite familiar with, of interviews and conversations and more lunches and more dinners, I just came to really, really like the people at Coinbase, in much the same way that I really, really liked the people I worked with at Facebook. I've just been very blessed and lucky that I've never really had a terrible boss. I've had many great bosses. I've never really had co-workers that annoyed me or frustrated me, for the most part; you know, people I've worked with in each of my jobs in my career are people that I still consider friends to this day. And so I saw that same sort of spark and magic here at Coinbase that I experienced at Facebook and elsewhere in my career, and added to that, again, the instinct or the nascent thought in my mind that this company was about to enter some pretty serious legal fights and confront some serious legal challenges. I just thought, like, I think this could be perfect. I think this could really be the right next move for me. And so once again, you know, I took on a new job, I started as the new guy, I had to prove myself once again, and, you know, still have to prove myself even to this day in many ways.
Khurram Naik: And then how did you think about, you know, the risk profile of the role is very different from Facebook to Coinbase, right? Facebook was here to stay at that point. Like you say, it was pretty much here to stay, and any of the legal issues it was facing was from the fact that it was here to stay. Coinbase is a very different scenario. So then tell me about how you thought about those two risk profiles. Was it the case that because you had, let's say, you know, skillfully managed your personal finances, you felt like, hey, that's all very sound, I can take a flyer here? Or was the basis of it because, hey, I've kind of seen it all, I've done, you know, I enjoyed the work as a partner, got a variety of experiences as a magistrate judge, took on this role with this different set of properties at Facebook, and now I can enter a new phase? It could be both of those, but tell me about, you know, what made the risk profile of this move attractive for you?
Paul Grewal: Well, I think in terms of, you know, my professional risk appetite, again, I've been very lucky that, you know, throughout my professional life I had the support of my wife, Gauri, who has been quite successful in her own career. That provided a certain amount of downside protection. I've also been fortunate enough to have experienced for myself that you don't enjoy large asymmetrical upsides without taking on asymmetrical downside risks, right? And, you know, having seen that to some degree at Facebook myself, but more importantly, you know, gotten to know people who had truly experienced that, having been a part of the Facebook journey from the very beginning, that was very appealing and attractive to me. Just to be very clear, the number one risk I had to confront and work through is, how do I tell my parents that I was going to work for a cryptocurrency company? My desi mom and dad were certainly aware of what Bitcoin was and, you know, what Ethereum and other digital assets promised to do, but they were much more skeptical, I'll put it that way. And at the same time, you know, like a lot of great desi parents, they were absolutely in love with Facebook and WhatsApp and everything else. And so, I was leaving a company that they literally engaged with several dozen times a day, every day, with the people that were closest to them, to go to this cryptocurrency company that, like, sold Bitcoin. What's that all about? So, thinking through that narrative, that was, like, much more of a challenge for me, you know, how I was going to make that phone call to mom and dad, than anything else I had to worry about.
Khurram Naik: Yeah, okay. And, yeah, explaining things to your parents is definitely a big obstacle, always, doesn't matter how senior or seasoned you get. That's always still the most important call to make. You know, I'm curious, in your story so far, I haven't really heard you talk about the role of mentors and talk about models for decisions. I haven't heard you say, well, I saw someone make a move like this and that seemed interesting, or maybe this move didn't work for this person for this reason, so I learned from a negative example. In these different moves you've made, were there models for you that you looked to for a gut check, for guidance, for rules of thumb, or was it really just saying, hey, I'm feeling this out on my own?
Paul Grewal: Well, I certainly think that I have had to reason through a lot of these decisions and opportunities largely based on first principles or, you know, fundamental values. But to be super clear, like, I've had incredible role models and mentors really at every stage of my career and really every stage of my life, starting first and foremost with my parents. Like a lot of our parents, mine, you know, took a leap of faith to the United States. They, well, my father came to the US in 1963. He left a sunny, warm place called Punjab with a huge, massive, loving family and landed in the frozen steppes of northern Minnesota, probably wondering what the hell he just decided to do when he came to the US for school. And eventually my mom and my older brother filled out after that. You know, when I think to the leap of faith that he and my mother had to make, you know, deciding between one amazing opportunity in a legal career in the US versus another seems somewhat childish, right? Like, it's just, like, oh, do I go be a federal judge or go be a law partner or go be a chief legal officer? Hardly the challenge that, you know, the people closest to me have had to confront several times in their lives. But even within the law, like, you know, I mentioned the judges that I worked for; you know, their joy in their work had a tremendous imprint and impact on me in ways that I mentioned, but, you know, continue to this day. And so that's always been an important touchpoint for me in thinking through new opportunities. I don't expect to be, like, giddy and on cloud nine every day. In fact, most days, you know, these jobs that you and I and others do are super hard, they're stressful, they grind you down, and in some cases they beat you up. But over the course of many of those days, and hopefully, you know, many months and many years in those kinds of roles, I think it's important to ask yourself periodically, am I growing, am I learning, and am I finding joy in what I'm able to accomplish? And so, you know, assessing that potential has been an important framework, in a sense, for me as I thought about new career opportunities. And then, you know, I think another thing that really helps is I've never tried to assume or presume for myself that I get another day or another week or another year in the future to reassess or reconsider, you know, a choice that I have. I don't want to say that I'm a complete fatalist, but even when I was a much younger person, I've always had this nagging sense that, like, you know, there's just a bus on a street corner waiting to run me over, or, you know, a change in circumstance in my life that comes in another way that could mean that I don't get to do this anymore. And so I try not to take for granted that I have these opportunities. And so if something catches my eye or intrigues me, I'm going to go do it, even if it means I'm going to stumble and bumble along the way.
Khurram Naik: It's totally fair that, you know, compared to, say, your parents, the magnitude of the decisions they're making and the different outcomes, that pales in comparison to a person in the privileged position of this great opportunity. But in the position of having those opportunities, how did you, did you look to any other guideposts? Did you see, like, other decisions, like, say, I'm thinking particularly of the move from Facebook to Coinbase, you know, from an agency role to a CLO, were there people that had taken similar moves with the, you know, you use the asymmetric bet, you know, similar asymmetry bets that either paid off or didn't pay off, that you looked to for, okay, that's a gut check, and that's how I'm going in the right direction?
Paul Grewal: Yeah, I mean, look, there are plenty of law firm partners who aspire to a life as a federal judge, whether it's a circuit judge, a justice on the Supreme Court, or a magistrate judge or anything else, for that matter. And so that was not all that hard to sort of understand, and it was very easy for me to picture myself following that very tried-and-true path. What was, I think, much harder was identifying role models in terms of judges who had left the bench, not just at, you know, the peak of their careers, but, you know, really in the heart of their careers, and, you know, had gone not back to a law firm where, you know, you largely sat in the corner office and gave advice about what, you know, your former court did or you did mediation, but, you know, as a working professional inside of a corporation where, you know, you're subject to performance reviews and bonus assessments like everybody else. And there are a handful of judges who have done that, but certainly very few had done that by going into tech, which is something I was particularly interested in. And then, you know, leaving what I think some charitably call big tech to go to what was still then a startup, a private company, in a very controversial, complicated space, like cryptocurrency. Yeah, there weren't a lot of people, I think, who necessarily did that, at least in the way that I did. And so, yeah, I really had to sort of reason a lot of this out on my own. And, you know, again, applying some pretty simple, maybe even too simple, you know, standards. Am I excited by this? Is this something that I will look back on in three or five or ten or twenty years and be proud of the work that I've done, whatever it is, however it turns out? And then the other thing for me, Khurram, has always just been, like, you know, the lawyers especially who I have admired more than any other have typically tended to be the ones who have engaged the law in a number of different ways over the course of their career. I've just, you know, while I've respected the heck out of the lawyer who goes to a fancy law school or not a fancy law school, joins a law firm as a summer associate, and thirty-two years later gets a gold watch, that was never what I wanted to do. I always wanted to be one of those people who was able to climb different mountains and engage with the law, which I've always loved, but in different ways, and be successful to some degree in each of those circumstances. So that was always, like, for me, what defined success. And so that's been useful in sort of sorting through different opportunities at different points in my career, because, you know, the fact that I'd been successful at something for five or ten years before didn't really weigh very much in my calculus.
Khurram Naik: And you mentioned that you love the practice of law, you love these deals to your past. Is it possible to have a rewarding career, or a rewarding legal career, and not love the law?
Paul Grewal: Yeah, I mean, I think you and I probably know, between the two of us, dozens, hundreds of people who, you know, from the outside and on the surface are, you know, enjoying all kinds of rewards from the practice of law, financial rewards, rewards in terms of prestige. But they don't have the rewards in terms of knowing what it is you're supposed to be doing on any given day, right? Like, law allows you to sort of compartmentalize what it is you're there to do and avoid having to sort of, you know, start each day or each week or whatever, figuring all that out. And yet, are they happy? Or even if they're happy enough, are they as happy as they could be? Was their work meaningful? Did they actually accomplish things that matter? In some cases, the answer is yes. And those are the people that I tend to admire and enjoy being around. But in many cases, I think among lawyers, the answer is either no or just disconcerting: I don't know. I don't know if I'm happy. I don't know if I've accomplished everything I set out to do. And so, yeah, I always wanted to be one of those lawyers who looked back with no regrets. And, you know, we've talked a lot about my successes and I'm grateful that you have focused on a number of them. But I've stumbled and fallen in many different ways. You mentioned, you know, the judgeship; yeah, I was a magistrate. Well, what we didn't talk about is I was at one point considered for a district judgeship and had my, you know, proposed nomination pulled, you know, at the very last minute. That was devastating to me. It was embarrassing to me. And yet, I had to pull myself back up. We didn't talk about the fact that when I went to Facebook, about 18 months or two years after I joined, the general counsel left, and I was considered to replace him, but I was not picked, I was passed over. That was embarrassing. That was frustrating. That was challenging. And, you know, more recently, you know, I've won a few cases and we've done pretty well in some investigations here at Coinbase, but we've also lost others. And I've had, you know, to make the difficult call to our CEO or to our board and explain that things were not going well or that we had not succeeded in the way that they had hoped for and frankly expected. So, you know, I'm stumbling along the way as much as anyone. And yet, you know, I don't really ultimately care very much that I failed. I think I would care much more at the end of my professional life if I never tried to do some of these different things. That's the regret I'm most afraid of at the end of my career. And so that's the regret I try to optimize against, to the degree it's within my control.
Khurram Naik: Yeah, I think that is worth commenting on, because I feel like I've definitely known a number of BigLaw partners over the years who, you know, talk about, you know, some entrepreneurial move that they've observed, maybe me, maybe someone else, and said, oh, I thought about doing that at one point, I would like to do that, you know, but, you know, they're just, I don't even know if it's necessarily financial, golden-handcuffs related, but they're just so tied to that identity of that one path they're on.
Paul Grewal: I think it's much more that, I honestly do. I, you know, for some cases, for some people, it may just be like they've got a certain lifestyle, they need to be in finance, and they're worried about their ability to do that in the short to medium term if they pursue a more entrepreneurial opportunity. But in most cases, at least among the lawyers that I spend the most time with, it's much more about their identity. I've been not just a lawyer, but a senior lawyer or a partner in this organization for a very long time, and with that comes a certain status, with that comes a certain amount of deference. But most importantly, with that comes a certain amount of defined purpose. You know what you're there to do, and it can be very scary to go from a world in which you know exactly what you have to do in order to be viewed as successful, to a world where, like, you don't even know what it is, like, you're aiming for. I mean, that's the life of most entrepreneurs I know. Or even people who pursue new opportunities where they have to learn that landscape all over again. I think it's that fear, as much as anything, that holds too many lawyers back. And, you know, I'm not immune from that or immune to that, but I hope that more and more people who practice law come to understand that it's a huge, wide world out there. There's so much interesting stuff happening. And as inspiring and impressive as the practice of law can be, it just barely scratches the surface in terms of all the other things that, you know, talented people can do in this world if they just set their minds to it.
Khurram Naik: And tell me about, you know, with risk-taking, in your experience, it sounds like, my impression of you is that you are definitely, if there's a spectrum of risk-taking, you're definitely much more on the risk-taking side. And I'm curious, do you think that it's something just, like, innate, someone's disposition, just the way that some people are inclined to be in the outdoors or whatever, just some people are happily drawn to that, or drawn to the arts or something like that? You know, of course it can be cultivated, but, can we say, largely speaking, some people are just more driven in a certain way, and that's just how it is? Like, do you think that risk-taking is a cultural issue that can be mitigated, or is it just inherent in people, and some people, like you, take risks and some people don't?
Paul Grewal: I think, you know, what you're ultimately asking about is the classic nature-versus-nurture thing. And I do think that there is a certain nature that defines or describes, I think, certainly among lawyers, those that are more willing to take risks or more willing to adopt a new sort of view of, you know, their professional life and their set of professional opportunities. But I think there are important ways in which that instinct, or that maybe even that talent, if I can use that word, can be developed and nurtured. You know, one of the things I think that kind of amazes me is, you know, if you think about it, right, think about how we recruit and attract people to the practice of law. You look at the sort of amazing range of experiences and interests that defines, you know, the entering class of every law school I'm aware of, right? And the fact that we encourage and really prioritize a wide range of diverse interests in selecting, you know, members of any given entering law school class. And then what happens over the course of the next three years, right? We sort of chip away at and winnow and beat down all the ways in which all these different people are, you know, special. And ultimately turn out, you know, a very similar profile, for the most part, of finished law-student product. And then from there, it only gets worse, right? Think about, like, what an entering class of associates looks like at any major law firm. Incredible range of interests, incredibly diverse talents. And we sort of define what it means to be successful and competent in a way that sort of standardizes that in ways that look very different, you know, when you finally get to the very small number of them who make partner or build successful practices inside the firm. So I do think that resisting that wherever possible is important. I think that having a bit of perspective and understanding our history is also something you can nurture that will, I think, lead to a greater appetite for risk or a greater appreciation that, you know, the choices that most of us in practice have to make are really, you know, choices that are extremely similar and really don't vary very much in terms of risk or potential downside, when you look at the grand arc of what most people in our society and our community have to deal with on a daily basis. And even if that's too abstract to really kind of engage with, again, I come back to, you know, our own families, our own stories, our own histories, where, in almost every one of, you know, our own families' stories, there are decisions that make, you know, the difference between, you know, BigLaw firm A and BigLaw firm B look comical, right? These are not, you know, life-altering choices. I just think having an understanding of history and an appreciation for it is also something that's really, really important.
Khurram Naik: You know, when you talk about risk, it seems to me that you've been taking risk with these career leaps; it's kind of this all-in risk that you take, necessarily, every time you do this. Are there ways that you could have, or that other people can, take smaller risks? Are there other ways, doing something on the side of some kind, that, you know, is a way to stretch yourself, challenge yourself, not as risky, but exposes you to, gives you the benefit of the exposure to new experiences and new perspectives that you're talking about?
Paul Grewal: Yeah, I love your curiosity. Yeah, I mean, that's how it is. An idea comes to mind, right? So a small example: you know, I think of risk and exposing yourself to new people, new ideas, as maybe the most important elements of developing a different approach to career choices. So, you know, it can be something as basic as, instead of, you know, flying to Maui like everybody else does for a week or 10 days when you're, you know, a hardworking law firm associate and sitting on a beach and relaxing in a way that you totally deserve and have earned, you know, maybe you spend that week or 10 days of vacation taking a pottery class at your local community college, where the people you're going to be interacting with are going to be very different, by and large, from, you know, the people who tend to go to the same resort and same island at the same time of the year. Maybe it's, you know, instead of moving up from a two-bedroom with your roommate to a three-bedroom, maybe it's, you know, staying in actually your own one-bedroom at least, and then taking the amount of money that you would have spent on the additional rent and dabbling in a little bit of real estate with ten of your friends, you know, starting with, you know, a little one-bedroom condo purchase that needs a lot of work and building it up and starting to develop a taste or appetite for real estate. You know, there's just a thousand different examples like that. Maybe it's instead of, you know, billing 2,400 hours a year at your firm in order to qualify for the next level of bonus, maybe it's only billing 2,200 hours a year and either taking on pro bono work that exposes you to different ideas and different kinds of clients and different kinds of legal issues, or, God forbid, spending those extra 200 hours a year reading a book or a series of books, right, continuing to educate yourself in literature and art and music. That's another way to take different risks and expose yourself to different ideas than a lot of people think about. So, yeah, I mean, at the end of the day, we all have to make choices and trade-offs. I just think that sometimes, and I'm guilty of this, I do this every day, you know, we imagine or come to convince ourselves that the choices in front of us are the only ones available, when if you just take half a step back, you're like, no, like, there are all kinds of different alternatives out there. It's just, you know, you have to take the blinders off sometimes.
Khurram Naik: You know, you talked about exposing yourself to people with different sets of ideas, and I'm struck that, you know, when you tell this story, you're telling about the magistrate role, is that more than when one friend came to you with, hey, you know, there's this opportunity that could be a fit for you, you know, who knew you so well and wanted to help you. How have you cultivated that quality of friendship and relationships, and what role has that set of relationships played in your career?
Paul Grewal: Well, I'm actually going to focus on the word "friendship" that you used, because that's actually the most important type of relationship. It certainly has been for me, because it's the one that's often the most neglected, right? Like, we all, I think, instinctively understand that inside of our families, we have a responsibility to our partner, and certainly to our children and to our parents. And so, you know, I think that's generally well understood, and some of us are better at that than others, but at least we all, I think, generally appreciate that that's just part of what you do in order to build a healthy and happy life for oneself. I think friendship tends to get ignored. I think, and I'm speaking now as a 52-year-old guy, I think older male friendship in particular tends to get ignored far more than we maybe want to admit. And so, you know, in my personal and professional life, I've tried to resist that. I tend to, you know, be friends with a lot of lawyers, like hanging out with lawyers, like people who practice law, although not exclusively; those tend to be my people. And, you know, throughout my career, you know, one of the things I've been proud of is that whether it was when I was a law clerk or a young associate, even on the bench, and even to this day, I feel that, you know, some of the most meaningful impacts I've had on other people come through my friendship with not just other men, but other women and others, who, you know, to varying degrees, I've remembered even when, you know, my own life gets very busy, and I have competing demands on my time in much the same way as we all do. So, to answer your question about how that's impacted, you know, my career, you know, I think that, you know, the fact that I've tried to be as helpful to my friends, and people I wouldn't consider friends but that I've just come to know, in giving them a piece of advice or thinking of them when I get a phone call about an opportunity that's not necessarily a great fit for me but could be a great fit for them, and, you know, with no expectations, just, you know, trying to help other people navigate this hard, crazy life as best as they can. And, you know, on occasion, sometimes I suppose that does come back, and I've been grateful for when it has, but I don't have an expectation. I don't think any of us should have an expectation in any of our successful friendships, because it's something that is much more valuable in the giving than in the receiving. I guess that's how I'd put it.
Khurram Naik: I understand what you're saying about, you know, the ways in which you think friendship is neglected, because my understanding is that family is well understood. And I think investing in, say, professional relationships, like being part of a bar association or something formal or informal, investing in client development, you know, I think those are well understood or discussed as well. You can go take a course on that. Family stuff is, you know, there's a lot of support for that, religion, lots of support for family-related things, lots of support for networking and professional stuff. You know, you can take a course on business development, you can hire a coach, but relatively little in the way of, hey, here's how to focus on your friends and here are reminders about your friends. So that occupies this valley between those two, is how I'm hearing you talk about this.
Paul Grewal: Yeah, and it's the hardest thing, because, you know, especially for lawyers, because, you know, we have pretty demanding schedules and lives, right? So professionally, you know, personally, like, there often isn't a lot of extra time or extra emotional space for time with friends or commitments to friends. And yet, you know, maybe I'm getting a bit more philosophical as I get older and reflective as my children, you know, move through school and ultimately out of the house into their own life, that, you know, you ultimately have a chunk of life, I think, professionally and personally, where friendship is really, like, all you have, whether you have a life partner, whether you have an extended family or not, because, you know, it's just, it's interesting that when we're younger, right, when we're in school, certainly, like, in high school and even in college, right, like, friendships are so central to how we spend our time and, you know, whatever joy or satisfaction we get out of the globe. And yet, I think that's as or even more true much later in life. And yet, I don't think we make the necessary investments along the way, necessarily, that set ourselves up for success. And I'm trying to resist that and avoid that, again, with very mixed success, but it's something I think a lot about.
Khurram Naik: You're going back to something you were talking about earlier, you're talking about, you know, difficult decisions that you've grappled with. And something I'm curious about for you, what was a decision you made that you're not sure you got right? There's a decision you made where you said, you know, I could have gone one way, I could have gone another, I went this way, but I'm not sure I made the right call.
Paul Grewal: Yeah, well, I'll start with a professional example. I don't know for sure whether it was, quote unquote, the right call or the best call that I made when I left the bench in 2016, in large part because I was so happy doing that work. And there just was a unique satisfaction in seeing the tangible results of my labor day in and day out, right? I could see individual parties in my courtroom. And these weren't, like, you know, the big fancy tech companies or others that, you know, a lot of people associate with my time on the bench. These were just regular people in court for either the first time or the hundredth time. And, you know, when I made a decision and it was the right decision, it was incredibly gratifying to see that look on their face. And, you know, would that satisfaction have only increased or grown had I stayed on the bench? I don't know. And, you know, would that have ultimately been more meaningful to me than whatever else I've been able to accomplish, you know, since I left the court, at Facebook or here at Coinbase? I don't know. So, you know, I think that will always be an open question. But, you know, I don't tend to be someone who dwells on it, only because, like, in many ways, those are unknowable questions, right? The answers are never going to be completely revealed. And fortunately for me, you know, there are many other things I have been able to accomplish instead that wouldn't have been possible had I stayed in that role. You know, a personal example that I think a lot about is that, you know, when I grew up in the Midwest in the '70s and '80s, I grew up in a very small town in Northeast Ohio, a place I'm very proud to be from, I felt compelled that I had to go away for school. And then, even though I returned briefly at the start of my legal career to clerk for a judge, I felt I had to move to California to pursue my professional dreams. And, you know, a part of me thinks a lot about, you know, the implications of that decision on, you know, the ways I've been able to spend time with my family. And, you know, the connections I felt to my local community, as, you know, I've essentially been living this immigrant life in California now for 20-plus years; I've never really felt at home here. So I think a lot about, you know, those choices, as well. And, you know, I think it's important to be reflective, but I think if you dwell on them too long, you ultimately end up right where you started, having traveled in a big, large circle, because, you know, there's really no way to know the answer to it. I think, you know, it's just much more productive and satisfying to think about what you've been able to do and accomplish that wouldn't have been possible had you not made that choice.
Khurram Naik: Well, it's right, because last time I saw you at a conference, in workout gear, you're the Chief Legal Officer of a high-flying tech company with a major regulatory component, you know, just at the bleeding edge of tech and financial issues. And so it's very funny to me to hear you say that you feel out of place in California. So tell me some more about that.
Paul Grewal: Well, you know, I've been now living here in California for roughly 25 years. I've lived here longer than I've lived anywhere else. And yet, like, I think a lot of immigrants feel, even though you may have spent decades in a place, if you're not of that place and from that place, you sometimes feel a bit like an interloper or a visitor or an outsider in some way. And that's just true for me here in Silicon Valley as much as anyone else. I appreciate that I present in a way that suggests I have overcome, you know, those obstacles, but, you know, in my heart of hearts, I'm still a little Indian kid growing up in a small town in Ohio, rooting for the Cleveland Browns, and finding no greater joy than, you know, Friday nights at our local pizza place after a Little League baseball game. That's still how I think of myself and how I see myself when I look in the mirror every morning. It's not, you know, some guy trying to, like, you know, solve the world's cryptocurrency problems or fight the latest tech fight as a chief legal officer.
Khurram Naik: Well, you've met my wife a couple of times, and she's got a question for you that is good. Look, you're in California at this, you know, this crypto company. There's got to be something that's woo-woo about the guy. There's something woo-woo about him. So what is it? What's the most woo-woo thing about you?
Paul Grewal: I don't know. I hate this question. I'm a pretty dull guy in many ways. I don't know. I suppose it's a little off-base for me that, you know, in my professional job, especially in cryptocurrency, I don't shy away from the darker corners of the internet. I have to spend a lot of time on Twitter. I spend a lot of time on Discord. I spend a lot of time on subreddits. And as many of your listeners will know, those portals can take you to some very crazy, dark places, particularly in terms of conspiracy theories. And, you know, all kinds of rank speculation about who's running the world and what's the secret government behind the government. Well, while I've never really subscribed to many of those theories, I am drawn to a good conspiracy theory. So maybe that's something I can confess on this podcast that a lot of people wouldn't guess about me.
Khurram Naik: What's one conspiracy theory you can't shake?
Paul Grewal: Oh gosh. Well, I've always been interested in the idea that extraterrestrial life exists and that our government has had a strong interest in managing that narrative for its own purposes. Now, I don't necessarily believe that there are, you know, skeletons or specimens of little green men in the desert in New Mexico. There were some recent congressional hearings about this that I found fascinating. But do I believe that extraterrestrial life exists? Absolutely. And would it surprise me or shock me to learn that if there was, you know, contact with extraterrestrial life, that one or more world governments would have, you know, been instinctively inclined to try to cabin or limit, you know, our understanding or knowledge of that? No, I wouldn't be. So maybe that's something I'm a little woo-woo about.
Khurram Naik: Yeah, you know, that is interesting. I'm fully buying into all the premises that you just laid out there. My only question is, you know, obviously by definition, if a government, if anybody is hiding something, by definition you don't know what's being hidden from you. But, you know, of course, over time, some things leak out, right? Some things leak out of some kind, you know, one secret is no longer secret. You know, the Tuskegee experiment, these kinds of things were once secrets and then, you know, I feel like there's just, like, you know, using this, like, say, physics or chemistry metaphor of an equilibrium, where there's such a strong density of something on one side and a vacuum on the other side, it's going to find its way out, right? There's something that's so potent, it's just two powerful a thing to keep hidden. There's just too much incentive for any individual to break from that, because there's such a huge payoff to that. So what is some precedent where we've seen that breakdown, or, if you haven't, how can you make sense of the most incredible, like, if someone was sitting on information, the unbelievable incentive and motivation you'd have to tell everyone, here's the craziest thing, there's extraterrestrials?
Paul Grewal: Yeah, well, I would say a couple things. One is, I'm not necessarily saying this is probable. I am saying it's plausible and most definitely possible. And I think the other thing is that, you know, when it comes to extraterrestrial life as one example, right, I think, again, like, yes, it's possible, it's highly unlikely that any small group of people could keep the secret. But what I do think is equally true is that, you know, as you highlighted with a couple of examples, you know, human beings have kept some pretty dark things quiet for a very long time until they weren't. And, you know, without being too morbid about it, I think there are plenty of examples, even in our recent history in the 20th century, where things that seemed utterly implausible were kept secret for a fairly long period of time, and then were revealed. And so, all that I am saying is that we shouldn't dismiss entirely the possibility that, you know, there are other beings out there, and certain people on Earth aren't necessarily assented to want to make that as publicly known as it should be. How's that for woo-woo?
Khurram Naik: That satisfies the woo-woo, I think. I think that's satisfyingly woo-woo. Well, you really love lawyering, so I don't want to miss out on that, so I want to pick up on that shortly. But you mentioned social media, so we can start from there. So tell me, you know, you're highly active on social media; you've got, like, 50,000 followers on Twitter, something like more than 25,000 on LinkedIn, so a large social media following. And that's, I think, probably, you were active on social media before you joined Coinbase, but certainly I think it exploded as a result of that. So tell me about, you know, I think so many lawyers are very averse to being active on social media, particularly, I think, somebody who, another lawyer who is in a company that faces such regulatory scrutiny, might be even more averse to having a public face and just, you know, making sure that every minutia is adequately messaged and lawyered. So tell me about, you know, I know risk has been a running theme, and so maybe that's just the simple answer, but tell me about the decision to be so active on social media, and, you know, what does it do for you? What do you get out of it?
Paul Grewal: Well, my, you know, my appetite for interviews and social media goes back well before my time at Coinbase. I, after all, did work for a social media company of some repute, of course, for half a dozen years before I came over to this company. But even before Facebook, when I was a sitting judge in a federal district court, I was on social media. I had a modest Twitter account. I was certainly posting a lot on Facebook itself, and elsewhere. And it was largely because I was just, again, curious and interested in how these new technologies could reach different audiences and allow you to have a different kind of voice than maybe was possible just before that. So, you know, when I came to Coinbase, I was certainly well aware that the cryptocurrency community tended to thrive on Twitter, on Reddit, in Discord channels, and elsewhere. And so it just, I think, was quite natural for me to look to those channels when trying to explain what it was we were doing here at the company, how I thought about the law and how the law applied to what was happening in crypto. And so it was just a very, you know, obvious and natural place. And at the same time, you know, I've tried to share a bit about sort of how I think about the practice of law and the profession in a way that goes well beyond just, you know, my particular industry, because I do think that there is an interesting conversation to be had out there among lawyers about how you navigate some of these challenges that you and I have been talking about, or, you know, just deal with the day-to-day struggles of the job. And so, you know, I have, again, found that by sharing sort of how I've looked at things or lessons that I've learned, certain people have found it, you know, useful or interesting in their own work or in their own lives. And that's very gratifying. But mostly, you know, it's not some grand plan on my part. It's mostly just about me wanting to spread the word about what we're doing here at Coinbase, encourage other lawyers to think about their professional journeys in ways that maybe they haven't before, and, you know, maybe even just kill a little time while I'm brewing my coffee in the morning. And there's nobody else to talk to because my children and my wife have left for the day, and I just need some other person, or a group of people, to communicate with.
Khurram Naik: Why is it important to message, you know, you have an outlet for, you know, if there's changes you need the SEC to make, to consider something, or a court to consider something, you have outlets for that. Why is it important for the public or the crypto community to be bought in?
Paul Grewal: Because these are ultimately public institutions, you know, whether it's the Securities and Exchange Commission or the Department of Justice or any other part of our government, they are ultimately there to serve the public interest. At least, you know, that's my perhaps somewhat naive view of how government's supposed to work. And, you know, just as I think it's critical that people understand what it is their government is doing or not doing in their name, I think it's just as important that these institutions understand what the people that they purport to serve think about these issues. And, you know, for all of its flaws and even risks and dangers, I think social media offers a very powerful and unique way to kick-start that conversation. And, you know, I'm certainly well aware of all the ways in which that conversation has taken off in unproductive and even harmful directions. But in my experience, Khurram, like, day in and day out, I have wonderful, you know, experiences and incredibly valuable conversations when I engage on Twitter or post on LinkedIn or whatever the case may be. And I think that as a result of that, and, you know, also the contributions of many, many more people that go far beyond just me, I think we have a much more informed conversation happening right now about the legal issues in crypto, about the legal profession that we all work in. And I think that's a generally good thing.
Khurram Naik: Has there been any, you know, the same question I've asked you about these different roles, an expectation for things you learn or relationships you make, what were the surprises along the way? Like, what's something that you've been surprised to learn in the course of being active on social media and building a large following, or, you know, the people that you've met along the way?
Paul Grewal: Well, I don't know if I was surprised by it, but I've been delighted by the fact that, particularly when it comes to the legal issues that we are confronting right now in crypto, whether it's securities law issues, issues involving sanctions, whatever the case may be, that so many good ideas come from people who I don't think in an offline conversation would be given, you know, the time of day by most other lawyers, right? You know, there's an old trope on the internet that when you're on the internet, nobody knows that you're a dog, right? Because there's a famous New Yorker cartoon to that effect. And I just love the fact that, like, most of the people who I pay the most attention to on Twitter, on Reddit, and elsewhere are people whose backgrounds I don't even know, and frankly, I don't even care about. I don't particularly weigh very heavily what law school somebody went to when it comes to debating the right way to think about, you know, the meaning of an investment contract under the 1933 Securities Act, for example. I just want a clever idea or a different way to think about the problem. And, you know, particularly in law, where we are still bound to traditional ways of weighing and evaluating the worth of someone's contribution, right? Where did you go to school? Who did you clerk for? What firm have you worked at? Is the company you work for a Fortune 100 company or is it a company I've never heard of? Like, those are all signals that have some value in certain situations, but for the most part, they have nothing to do with, is the thing that you're saying smart? Do you have a good idea? Is your comment something I should be paying attention to? And I love the fact that in an online space, the ideas tend to be at the center of how we value people's contributions. And I just love that, because more often than not, I get really good ideas or a different way to think about a particular legal issue that I'm wrestling with from individuals who I suspect wouldn't garner a lot of attention in traditional places and spaces in the law. And I think that's awesome. I just feel like that's a much fairer and much more interesting way to operate and a place to live. And so that's as much as anything that has surprised me about my experience talking about law and talking about crypto on social.
Khurram Naik: Are there groups of lawyers, or are there niches of lawyers, or all lawyers, who have a reason to become more active on social media? For most lawyers, you're in a unique position. There's a key benefit to messaging around these topics. These topics are at the bleeding edge, they're changing, they're relevant to a lot of people. And so maybe you're in a very distinct position, and then also the chief legal officer. So short of that unique set of circumstances, does it make sense for more people to be involved in social media? Is there a profile in your mind of a kind of lawyer who should be more active on social media?
Paul Grewal: Well, I mean, I'm not one to tell anybody else what to do or how to do it. I will say that the first rule I generally tend to try to apply when I think about how I communicate with others, whether it's on social media or anywhere else, is, do I have something interesting to say? One of my pet peeves about lawyers on social, but also in communicating more generally, is that more often than not, they skip past the "do I have something interesting to say" and focus on "how do I say it?" So I think that is where I would begin, and would encourage others to begin. And then I think that, at the same time, and this touches on something I was saying earlier, I think sometimes as lawyers we presume that what we know or what we do is utterly uninteresting to anyone other than ourselves. And the fact of the matter is, there's something interesting happening in just about every lawyer I know's life every day. And the only question is, how can you package it and present it in a way that's compelling and interesting to others, even if they have no idea what it is you do or how you do it? So that's the piece, I think, that sometimes people miss. They either presume that it's interesting to everyone, or they don't take even a brief moment to think about, how do I present and frame this in a way that is compelling? And I think the best way to do that is something, again, that you and I talked about earlier, which is, when we were talking earlier about the best trial lawyers and what makes them so effective in court, and a key element of their toolkit being curation and deciding what not to say and what not to argue, I think that's just true for social. Less is generally more. And I think a lot of lawyers, too many lawyers, when they try to engage with social, try to accomplish too much or say more than they have to, instead of just really focusing on what it is that is compelling and interesting in whatever it is that they do.
Khurram Naik: You know, I think also it sounds like the story of Coinbase and what it's looking to do is essential. And I think it's been common, or new but valued, among high-performing tech companies, companies where founders have a clear message. And so I think that's something that Paul Graham has underscored for a number of years, the storytelling component, and Coinbase and others are, I think, influenced by Paul Graham in that way, or in that sphere of influence. So tell me about, lawyers, of course, litigators, are natural storytellers, but in the course of being at this cutting-edge company that's got a story to tell, and flexing your muscles on social media, what is it about storytelling that you've learned? What are storytelling principles that you've learned?
Paul Grewal: Oh gosh, I think that a couple of things have just become clear and clearer to me over time. And this is true whether it's LinkedIn posts, this is true whether it's a closing argument in a federal district court trial, or anything in between. I think the most important elements of a great story are the people, the characters. It's less about what they do or even how they do it, and much more about who they are and ultimately why they have made the choices that they've made. And, again, this doesn't have to be some great piece of literature that we're talking about. This could literally be four lines in a tweet. I think focusing on the people generally tends to make for a much better story than anything else. I think another element of storytelling that's super important is to try not to accomplish too much, again focusing on the notion of curation. There doesn't have to be a grand unifying point or theory necessarily to a great story, but there does have to be a point. And so I think sometimes people who struggle with storytelling overlook the fact that you should be able to answer the question, so what is the point? Whether it's a tweet, a novel, or anything else you might compose. And I suppose one other element of storytelling that I try to focus on is, am I offering something new or fresh, you know, compared to what I've said before or what others are saying? Because I do think that, as humans, we are wired to the novel, right? We are always looking for the next thing. And so rehashing or repeating points or narratives that have been made or laid out over and over again before, also I think tends to take a pretty good story and turn it into a not-so-interesting story pretty quick.
Khurram Naik: And I also want to go back to something you were saying about how you don't look to tell people what to do. I fully appreciate that. But I'm curious for you, I mean, I feel like there are so many recurring scenarios in the practice of law that lawyers find themselves in. And especially for the reasons that you identified, where, you know, so much about the legal training and the practice of law is conforming and then standardizing. And so then you have these kind of averaging effects. So I think that makes it, for the reasons you identified, all the more challenging for people at a key juncture of their career to make decisions. I think, you know, all the canonical key junctures that people are at, you know, one is your mid-level associate who says, I don't know if I want to keep on, you know, the partnership serum. And I don't know if I want to make partner at my firm. I don't know if I want to go in-house. I don't know if I want to do something completely different. I'm sure you run into people like this all the time. You know, what do you, and recognize this is not necessarily advice, maybe questions you're asking, what do you say to someone to help them sort through that? How do you help someone sort through that canonical issue that a lot of smart people find themselves in?
Paul Grewal: Well, gosh, there's all kinds of ways out there on this topic. So applying my own standard that I just articulated a moment ago, maybe I'll focus on a slightly different take I have on this. The number one thing I ask someone who comes up to me with that kind of question is, forget about what you want, forget about what you enjoy, what are you really good at? Like, if I asked ten of your friends or five of your professional colleagues, what's the number one thing you think of when you think of this person in terms of what they really, really excel at, what are they going to tell me? What are they going to tell you? And I start with that because, again, this is just sort of the way I've thought about my professional career. I have found that being really, really good at something in the practice of law tends to be pretty satisfying, even if it's not necessarily something that I particularly enjoy or aspired to. And so it's not the be-all and end-all to, I think, the very important and hard questions that you get asked and that people confront for themselves in their own careers over and over again. But really being candid and honest about what you're good at, I think, is something a lot of lawyers overlook. I think a lot of us imagine ourselves to be very good at certain things we're not actually very good at, and completely overlook or ignore areas where we are extremely talented and accomplished, but, you know, are so second nature that we don't really focus on them. That's maybe a different way I look at that question than some other people.
Khurram Naik: I really like that. So now I'm going to apply it to you. But you have two audiences. So you, as you said, you like associating with lawyers and you've got plenty of contact with lawyers. What do you think the lawyers in your life would say for you? What is it that Paul Grewal is particularly good at?
Paul Grewal: I think I am quite good at managing chaos and dealing with emotional overload in moments of crisis. I think that was true when I was in a courtroom and a defendant had an outburst or a witness broke down on the witness stand, or where a juror would lie to my face about why they couldn't serve and it turned out that wasn't true. I think that was true in my law firm life when junior or mid-level associates would suddenly break down or not show up for work or walk out in the middle of trial. All of those things have happened to me. I certainly think that's true in my current role at Coinbase, where, as the Chief Legal Officer, every single day I am confronted with some completely out-of-left-field crisis either at the company or in the industry as a whole. And my first instinct is to pause, to figure out what needs to be done, as we talked about earlier, and to focus on the here and now and deal with the emotional aftermath, you know, only after we resolve a situation or put something to rest. I think those experiences, that talent, is probably what I'm best at, relative to my peers, as much as my ability to write, my ability to speak, or really think about legal issues. That's sort of home.
Khurram Naik: Okay, that's good. And then I want, that definitely ties into running themes you've been talking about, you know, those are notable moments like stepping into the magistrate judge role, managing the emotions was a key part of your roles, that makes a lot of sense. But now I'll switch, I'll ask a question. So now you report to a board of directors, and these are people like Marc Andreessen, Fred Wilson, Toby Lütke, you know, people that are successful software entrepreneurs, VCs. So what would that audience say is your alpha, your euro, your expertise?
Paul Grewal: I would hope that that audience would say that I am uniquely able to identify paths forward and avoid being so sucked into the classic lawyer's posture of, we can't do this, we shouldn't do that, there's no way around X, we're never going to pass Y. I think I'm able to identify paths forward that may not have been immediately or readily apparent to others. And I think my board would call that the same thing else that I do. I hope they would.
Khurram Naik: And now, like, with looking at that board, what have you learned from them? What have you learned about how they approach decisions? Definitely skillful lawyers, jurists, you know, what can we learn from that group? Because, you know, fewer of us as lawyers have contact with people in those roles. And there's a lot of success, you know, in different domains; there are quite different kinds of decision criteria. But what can we learn as lawyers from that group? What have you learned?
Paul Grewal: Yeah, the self-made founder tech billionaire is definitely a species that I am much more familiar with than I ever would have guessed when I graduated from law school in 1996. It's certainly been the case here at Coinbase. You've mentioned several of our board members. Obviously our CEO Brian Armstrong, who also serves on the board, fits that bill. Mark Zuckerberg, my previous boss, I think also qualifies on that score. One thing I've learned from working with all of these people, and they're very different from one another, they're not uniform by any stretch, but they do share certain qualities, is that they are insatiably curious. They generally want to know why something is happening as much as what is happening or what needs to be done about it. That curiosity is something that is extraordinary. They are certainly all fearless in that, you know, these are all people with lots to lose on any given day. And yet they are very comfortable taking outside risk when they are convinced that they are right. And then the last thing I will say is, I think that a lot of people have a somewhat stereotypical image of that type of successful person as being rapacious or indifferent and even hostile to the people around them or the people who are impacted by what they do. And that just hasn't been my experience. Over and over again, I have been impressed that the people that I've worked with who fit that bill that you just described really do care deeply about the wider world, and what kind of world they're going to leave behind when they leave. And I can appreciate maybe some skepticism around that, and these are not saints by any stretch. They're just as human as the rest of us. But there is, you know, I think a genuine, not just interest, but commitment to, you know, figuring out a way to do interesting things in this life and leave the world a better place than, I don't think, always gets understood when we look at these captains of industry, making these grand decisions that impact billions of people. So that's something I just think about.
Khurram Naik: I'm trying to trace, you know, with all the things that you've learned so far, I'm trying to trace, you know, there are these data points for, you know, what makes Paul make a move. What is it that Paul is looking to love? And I think extrapolating from here, you know, you're already in the Chief Legal Officer role at a company that's had a lot of success financially, and, you know, that's, you know, benefiting you personally. And so that dimension sounds pretty, it seems pretty sound. You know, you're working on cutting-edge legal issues. It would be hard to imagine something more at the forefront of, you know, public disputes with, you know, a regulatory body, and trying to be on the side of what you think is right. So it would be hard to top that. You know, what company could give you, you know, more challenging legal objectives to attain, or compensate you in some way, you know, more significantly for that? So I feel like that would be hard to top. So it's got to be something else, right? And so maybe, you know, obviously it could be, like, flexibility, maybe, you know, you've worked as hard as you can. Actually, that's not true, you're a very spry 51-year-old.
Paul Grewal: Fifty-two, as of yesterday, just to be clear.
Khurram Naik: Right, fifty-two as of yesterday. Okay. So it can't be that. So I wonder if the answer is, you know, maybe it's something along the lines of impact. So, you know, I think that's the thing: if there's anything that seems like close to regret, if you want to put it that way, it's, you know, looking back and saying, what would a life in the judiciary have been? Because, you know, the range of impact you have on society is very stark. So it could be something that joins a lot of impact. I don't have an answer.
Paul Grewal: So I'm not going to speculate, but I'll ask you this instead. You know, I've observed that there are certain, you know, GCs, chief legal officers, or even law firm partners who have had a lot of success in what they do, but then taken on these non-legal roles. So I saw, you know, recently, Jason Kwon of OpenAI moved into the chief strategy officer role at OpenAI. And then you've got Gordon Moodie, who just moved into the chief policy officer of Harvey, a legal AI startup. And, yeah, Brad Smith, the Microsoft former GC, is now a president. There are, I think, many examples like that, for sure.
Khurram Naik: There are certainly examples. Maybe you're familiar with so many that you can call them many. But so I'm curious, you know, what would it take to make that attractive for you? Or what do you think makes it attractive, or is it a path that more lawyers should consider?
Paul Grewal: Yeah, I think lawyers should definitely consider it, because I think that a lot of what makes people really effective as lawyers would serve them extraordinarily well and make them just as effective or more effective in other roles, whether it's serving as a chief administrative officer, a CEO, a president, or something outside of the law or corporate life altogether. Yeah, for me, that might be something in my future. I don't know. I think, though, that, like, less important than the title or sort of the organization is the problem set and the collection of challenges that I would have an opportunity to engage with in that kind of opportunity. I just think that, and one of the things that I really am proud of as a member of the legal profession, and I think a lot of lawyers are really, really excellent at, is dealing with uncertainty, orienting to problems where there is no obvious answer, being able to reason from first principles. I just think these are all tremendously valuable skills that lawyers develop each and every day, no matter what kind of practice you have, and they could serve them very well in other roles that go well beyond the law. So, you know, I do think, though, that, like, to be successful in that type of different opportunity, any lawyer would have to, again, be willing to shed their own skin a little bit, express and genuinely embrace a certain degree of humility that there are lots of things out there that we don't know, and also just sort of get excited by the fact that you're doing something very different from what you've done before, as opposed to being intimidated by it or turned off by it. I think if you have sort of that mix of perspectives and attitudes, I think as a lawyer, you could do very well in other roles. Of course, we haven't even talked about all the things outside of corporate life where I think lawyers bring a lot of unique experiences and attributes that could lead to some amazing success.
Khurram Naik: It would be hard to think that there's a better point to stop at than that. I feel like that's a really good summary of themes in your life and in your career, so yeah, that's a great place to stop right there. Awesome. Well, Paul, thanks for the time. Happy belated birthday.
Paul Grewal: Thank you. I appreciate it. This is a fun conversation. I appreciate you having me on. I've enjoyed it.