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Deep conversations with underrated lawyers.
This is Horum with Horum's Quorum. My guest today is Paul Greywall, 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 a tick and the first principle to reasoning he uses professionally. Here's Paul.
Khurram Naik:Great to see you. Thanks for joining.
Paul Grewal:Great to see you as well. Thanks for having me.
Khurram Naik:So I wanna hear about know, we talked last time about your workout routine. And I know that you said that 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. 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, mixing a little weight lifting. And then if I could squeeze in around a golf or a walk or, a bike ride, it's been a pretty good pretty good week for me.
Khurram Naik:And is it usually is it 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. I'm generally a pretty early morning person, kind of always have been. 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, 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 formula?
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 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. Things sometimes fell apart. But I think I've gotten more consistent with it.
Paul Grewal:And then the other thing is, as the body ages, a couple things happen, right? You get slower. Hopefully you don't get too much weaker. But I've certainly placed much more emphasis on just maintaining my physical strength and my endurance rather than literally sweating over whether I'm in a shape ten seconds off my five ks time or whatever the case may be.
Khurram Naik:Yeah. And is there anything else you do for wellness in general? Like how else do you center 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 has been a regular attendee of religious services.
Paul Grewal: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 from 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 that know you well have observed about you is that you are very something that makes you special or different is that you maintain a pretty even keel and don't tend to get too elevated. And I know that you're a former litigator, and 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? 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 gonna have to start using that because in my experience, particularly in trial and in litigation generally, it's more agitated than elevated. I think for me, Quam, part of it's just, I think, 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.
Paul Grewal:And at the same time, I try to eat right, I try to sleep right, try to exercise, what we've just talked about, in ways that I think also literally lower the blood pressure, lower the temperature, and, hopefully allow me to focus on what needs to be done rather than how I feel about it. I deal with my feelings later. You know, my first priority in most situations 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 there's feel like your story, lots aspects of your story are well known. You've got a very substantial social media following. You've done a number of interviews over the years.
Khurram Naik:Think a lot of people know your story in large part, and I thought this would be an opportunity to get into all the other bits of your story that I think are less. What are the other aspects of your life that have facilitated the decisions that you've made? And so I thought we could maybe talk about that. So maybe we'll start with I don't know, a contrarian version of your story start out
Paul Grewal:with Sure.
Khurram Naik: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 that to a magistrate judge.
Khurram Naik:Now, I think a lot of aspects of that have already been told, but what are the 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 think, Hurrem, I had a 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.
Paul Grewal: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 up to that point in my career, you know, 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 that I 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, and then, you know, were definitely had the qualifications to be a Discord judge. You know, why 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. When I applied to be a magistrate judge, I wanna say I was probably 38. So relatively young, not the youngest ever, but relatively young. And 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.
Paul Grewal:I think in a very hierarchical structure like federal courts, we naturally think about the Supreme Court justices first and foremost. They probably occupy 95% of our mind space. They certainly consume 90 or 95% of the conversation and oxygen in any room of lawyers. But in in the lower ranks of the of the judiciary, there are incredibly talented people doing incredibly important work. And and just as important, at least from my perspective, given incredible opportunities to be very creative, to do a lot of good for for real, 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.
Paul Grewal:And so as I thought more and more about what magistrate judges do, what I might be able to do in that role, and the opportunity in front of me just became more and more attractive to me. And I cared less and less about whether it was sufficiently high enough or high enough in the hierarchy to warrant 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, 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 an equity partner in a major law firm to the lowest ranked junior judge in the federal government. Required a bit of financial and emotional gymnastics as well, I was ready to do all that.
Khurram Naik:Tell me about that. I think that's really huge. And that's, I think, a major obstacle for a lot of people at every level to make decisions is being able to handle a drop in comp or a change in status. How did you plan for that? How did you know that you're set up?
Khurram Naik:How did you know you're 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 I think well, let's start with the financial because in some ways, that's 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 one hundred 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.
Paul Grewal:And, you know, as a rising partner in those ranks, starting to attract clients, starting to attract really interesting cases, you know, was at a position and 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. And so that provided a certain amount of flexibility as well. And and at the same time, as I think a lot of us struggle with, as the income rises and as the resources grow, so too do our appetites or tastes 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, and figuring out what didn't so that we were able to maintain a relatively, being the keyword here, modest lifestyle that reflected 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.
Paul Grewal:And so with that sort of mental model in mind, it felt less scary for me when I was extended the offer to join the Northern District Of California as a magistrate judge 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 don't have a certain amount of confidence that things are gonna be just fine. There were plenty of people who did just fine living on the salary and compensation package of a of a of a junior federal judge, especially with a working spouse. And so that that helped.
Paul Grewal: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 literally command a room, right, in ways that are not possible for most people. And that certainly was all true. At the same time, for me, I was going from a place where I had associates, I had clients, as I mentioned before.
Paul Grewal:And inside of a law firm, you really are, as a partner, the center of that universe to a place in the courts where, as I said, literally, was the youngest, the most junior, certainly the least known judge, not just in my court, but certainly nationally or 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 gotta start at the bottom and I've gotta 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 associate or in whatever other situation, it just became easier for me to, you know, adapt and steel myself for that learning curve that comes with any new opportunity.
Khurram Naik:And then in that role, what were the skills that you you probably had a set of 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 so so for judges, right, like, at least as I thought about it, you know, it's 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 and deliberating on, you know, credibility determinations. All that stuff, I think, is relatively well understood.
Paul Grewal: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 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 on day one, as a magistrate judge, I was literally not quite literally, but nearly literally putting thrown out onto the bench and, you know, thrown into a criminal law calendar where I had very experienced assisting 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 in that setting that I had to embrace in a pretty direct way.
Paul Grewal:The part of the job though, Krum, where I felt like I didn't appreciate what skills were gonna 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 a, you know, software license or a decision as to whether somebody's gonna spend the next thirteen months awaiting trial in jail or anything else, all of those situations require, I think, a certain ability to navigate some pretty complicated emotions in the room. And those emotions stem not just from the parties. Pretty easy to understand why a criminal defendant in that situation may be a bit agitated or elevated, as you referenced earlier.
Paul Grewal: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 wanna be in there for the most part, don't understand what's happening. They're confused.
Paul Grewal: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 of 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 learned over time? How do you manage people with Just have strong opinions, strong feelings?
Paul Grewal:Yeah. Well, I mentioned one thing I think that 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. 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.
Paul Grewal: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 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 sort of elevate their performance.
Paul Grewal:Whether it's 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. 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, 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 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 into me because I will help you here. And so how did you establish that comp how did you, I guess, like, maybe avoid the outcome of, say, impostor syndrome? Like, hey. Like, I'm very skilled at IP, but I I'm not really knowledgeable the way that, you know, experienced US attorney is about criminal matters.
Khurram Naik:How did you establish that authority and and and ramp up and then and then put yourself 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. Because the fact of the matter is, whether it's in a courtroom or in a boardroom or anywhere else, like, 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?
Paul Grewal:It's it's a lot like being in a surgical theater. Right? You you would, I think, be more than a little bit anxious to learn that your anesthesiologist was humble and at the same time lack confidence in what he or he was doing. You want someone who knows 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 from my perspective, the number one thing, Corinne, that's, I think, helped is that I've shared my genuine curiosity in what others do.
Paul Grewal:It's amazing to me how in in a single day, certainly in a courtroom, but I think in many other professional settings in the law, you know, we are just all so privileged to encounter, work with, in some cases, against, is some incredibly interesting people who've done some even more interesting things. And I think that even if you have almost no basic or baseline understanding of what it is that a trust and estates lawyer does or why it is that an agent for the FBI pursued an invest you know, pursued an investigation in a certain way. If you have a genuine curiosity and and a drive to wanna 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, I like that. Tell me about, on the bench, you observed a lot of advocacy. What was a piece of skillful 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 are or the most important arguments are the questions or arguments that you didn't make or didn't post. I think of great advocacy as ultimately about curation. Right? And 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 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.
Paul Grewal: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 that, and continue to see that is very consistent among the grades.
Khurram Naik:I like that. So then tell me some more about again, with this notion that we're we're we're building out the the the hidden story of Paul Graywald, the things that people haven't heard about. Because I I think, you know, plenty of people heard about your move that I think excited, surprised, wowed a lot of people from the best through 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 love 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.
Paul Grewal: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 of what I would be working on over the course of the day, just given sort of the random and tumultuous nature of most most court cases, all of that was fantastic. I certainly love the relationship I had with my fellow judges. I most of all loved and adored the relationship I had with my law clerk. So it a heady, wonderful experience.
Paul Grewal:And so might be quite understandable or reasonable to think, well, then why would you leave? And how could it be that you were so happy and yet you were willing to give it all up? And I think for me, was this was not 2016. I'd been serving as US magically judge for nearly six years at that point. Not nearly as long as many, but 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 there were other professional opportunities that I wanted to pursue and other professional skills I wanted to acquire and develop.
Paul Grewal:At that point in time, I had probably written, I don't know, a couple 100 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 thirty, thirty five civil jury trials in nearly six years, which was a pretty heady clip. And so had that experience, I think, to the degree that I had hoped for.
Paul Grewal:And at the same time, when I learned about the experience 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 stock of cases, when you sit with a magistrate judge or a trial judge of any type in any federal court, it all just kind of made sense to me. And so, as someone who was never afraid to 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 an earlier theme you you you were exploring, I had to sort of, at that point, ask whether I could once again start as, if not as a junior person, a new person in a very, you know, complicated organization.
Paul Grewal:Facebook was stuffed with super smart, super talented people. And, you know, no one was gonna call me Judge Greywall when I walked around the campus in Menlo Park. Although one or two did. For the most part, you know, I was just Paul from Building 20 Or 23. And, you know, I had my badge with everybody else.
Paul Grewal:I rode my bicycle and locked in the 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 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, and brilliant even if the other half thought I was the opposite.
Paul Grewal:You know, I was just, at that point, very, very comfortable in my own skin and and 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 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 there was you know, what was the the tiebreaker that made you go to Facebook?
Paul Grewal:Well, I hadn't really considered any other role, certainly seriously at that point. 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 would turn 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 tech was a force for good. And it was becoming increasingly clear, certainly by the early twenty sixteen, that that view was starting to look a bit naive or simplistic.
Paul Grewal:And the company was about to add 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, 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's some that surprised you that you weren't expecting to pick up. What were the surprises? What were the things that you
Paul Grewal:Yeah. Well, yeah. Mean, look, at that point in my career, I mean, I tried a lot of cases, not only as a trial lawyer, but at that point as a trial judge. I mentioned that I'd worked on a bunch of different kinds of cases, data privacy, intellectual property, competition issues, whatever the case may be. So I had a lot of confidence, much more confidence at that point, 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.
Paul Grewal:What I had never done though, Quoram, was I never led an organization. As a law firm partner, you don't really lead an organization the same way as you do in other settings, such as inside of a company or in the military or elsewhere. You have a group of associates that you sort of assemble on the fly. You form these coalitions of the willing that, you know, move forward managing these cases, and then and then a handful of them, you take the cases to trial. And then you break up the band, right, and and you 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.
Paul Grewal: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 100 people.
Paul Grewal: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 comp, compensation, and performance issues just like any other leader of an organization inside of a company. I'd never done that before. Oh, and by the way, had to go back to a world where I had a boss like everybody else.
Paul Grewal:And 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 adapt back to that world or really adapt to it for the first time.
Paul Grewal:So there 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 same thing. The move to Coinbase was a lot of attention for that. It was obviously a company that a lot of attention was being given to, but it was still a remarkable move. So what's the story that people haven't heard about the calculus and 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 was I've always been a huge believer, Hoham, that 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, yeah, 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. 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.
Paul Grewal: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. 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 messy issues for the company, everything from Cambridge Analytica to, you know, all sorts of different class actions involving data privacy and intellectual property and regulatory fights with the FTC and elsewhere.
Paul Grewal: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 may have been less obvious in all of that.
Paul Grewal: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 or other underpinnings of of Bitcoin and, you know, all the other tokens and assets that we deal with. I had none of that. I had 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 an MJ on the bench, and I was asked to review a rule 41 search warrant from a FBI agent looking to see some Bitcoin in investigation. This was back in, like, 2012 maybe, maybe even 2011.
Paul Grewal: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.
Paul Grewal:Because at that point in time, you know, you will be, not only an important part of the of the work, an important voice in the conversation, you're gonna you're also going to be, I think, uniquely positioned to assume leadership. And, yeah. That was that was essentially how I thought about Coinbase in 2020. And once again, my vague instincts that the company was about to enter a huge number of really messy fights turned out to be pretty true, at least if you look at my my to do list this morning in 2023.
Khurram Naik:Doubling back to to Facebook, so decision to join there. So there, I mean, I think we you know, your role now, you know, the the the role of resolving regulatory issues is seems to be essential to the business. So your role is, you know, the overlap between product and your role is huge. That seems to be less the case 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?
Khurram Naik:What made you think that you're gonna skill up and level up from that move? Aside from the company's trajectory, what made you think that that function good for you?
Paul Grewal:Yeah. Well, I 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, was true that Mark Zuckerberg had never testified in any court case. And if you fast forward just eighteen months after I joined, when the Cambridge Analytica scandal blew, and suddenly Mark and others were being called in front of Congress to account for and explain what had happened in that situation, Those were all very novel experiences that proved to be quite searing for the company.
Paul Grewal:And so as it turned out, actually, what was once, I think, I wanna say it was a quieter function because Facebook's always had its share of litigation and regulatory investigations. But what became a very public and strategic challenge for the company necessarily meant that the 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, you know, how much, the company has changed over that period of time.
Khurram Naik:And can you be a little more specific about, like, how you like, how is the option here for the Facebook? How did you come across that opportunity? Did Facebook approach you directly? Tell me tell me about a little more of the because it's kind of unusual for a mastery judge, I would think, to be approached by a company. Tell me some more how that happened.
Paul Grewal:It's pretty unusual. You know, we don't have We don't have on campus recruiting in the federal judiciary. So 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 twenty fifteen or early twenty sixteen that Facebook was looking for a new kind of leader. I think the general counsel, Colin Stretch, was very forward looking in his view, 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 throughout some very intense regulatory investigations.
Paul Grewal:And so when my friends mentioned to me that Colin was the leadership beyond Colin was looking for this new kind of leader for the company, the more I thought about it, you know, the more intrigued I was that, you know, I realize I present a somewhat atypical or unusual profile in terms of, you know, 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. And so at their encouragement, I reached out to Colin. We had a cup of coffee. And just like you know, so many jobs and so many opportunities for all of us.
Paul Grewal: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. And before I knew it, I was, you know, hanging up my rope, literally, and signing up for a very different kind of life at the company.
Khurram Naik:Well, earlier you referenced this concept of seizing opportunities. Know, like, hey, here it comes. You gotta be prepared for it. And so I wanna kind of explore that theme in some of these other moves that you made. And so there, let's say with your friends, how do they know to come to you with that?
Khurram Naik:Did had you told your friends, hey. By the way, I'm open to other opportunities, or, you know, was there something you messaged that way? Not, like, waving a a flag saying, I need to get hired or whatever because you said you were happy. Tell how people need to tell you about this.
Paul Grewal:Yeah. I mean, think it was really not much more complicated than a conversation or two in which 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.
Paul Grewal:And so, you 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 or incremental. And so I said, yeah, I'll have a cup of coffee. Let me 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 sort of what they wanna do or need to do next in their professional or personal life.
Paul Grewal:That just just stopped in 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 weigh 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, 10x 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 not only much more happy, but happier 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, are there those big leaps and and are those big, you know, increases, however you define it, available or at least potentially available in a way that makes, you know, makes it worth pursuing.
Khurram Naik:And then with the move to Coinbase, how you how did that opportunity there's the opportunity, there's you. How did those two converge?
Paul Grewal:Yeah. Yeah. So Coinbase was again, I know a lot of people talk about how they are tapped on the shoulder or someone whispered that people are interested. My process was much more pedestrian and mundane. I got a call from a recruiter, just like everybody else.
Paul Grewal: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.
Paul Grewal:And yet and yet, I think by by '20, '20, 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. That, you know, there there were real opportunities with this technology and real markets to build and develop. And yet, 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 had, at this point in time now, managed some very complex litigation, or rather investigations, for a major tech company.
Paul Grewal:And critically, Hurom, who had, you know, at that point in time, learned and understood how to navigate the corporate world. 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. And how to exercise influence and even maybe power, on occasion with no real explicit authority. You know, these are these are skills and talents that I think are also critical to success and having, you know, learned a certain amount of 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 in a in a pretty significant way at Coinbase, given that Coinbase at that point in time was less than ten years old, was, you know, a generation or two earlier, in its development than, say, Facebook was. And so it just it made a lot of sense.
Paul Grewal: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 like the people I'd 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 coworkers that annoyed me or frustrated me for the most part. You know, the people I've worked with in each of my jobs in my career are people that I still consider friends to this day.
Paul Grewal:And so when 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, 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.
Paul Grewal:I had to prove myself once again and, you know, still have to prove myself even to this day anyways.
Khurram Naik:And then how did you think about, you know, the the the risk profile of the role is very different from Facebook to Coinbase? Right? Facebook was was a derisked at that point. Like you say, it was just pretty much here to stay. And any of the legal issues it was facing was from the fact that it was here to stay.
Khurram Naik: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, know, skillful management of your personal finances, you felt like, hey, like, that's all very sound. I can take a flyer here. That was basis of it.
Khurram Naik:Was 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. Of course, could be both of those. But tell me about what made the risk profile of this move attractive for you.
Paul Grewal:Well, I think in terms of my professional risk appetite, again, I've been very lucky that 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 or outsized risks. Right? And, you know, having seen that to some degree at Facebook, but 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.
Paul Grewal:Just to be very clear, Kareem, the the number one risk I had to sort of confront and and work through was how do I tell my parents to go work for a cryptocurrency firm? My my Daisy mom and dad were certainly aware of what Bitcoin was and, you know, what ETH 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 DC 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.
Paul Grewal:What's that all about? So I'm thinking through that narrative, probably, much more of a challenge for me. I was gonna 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 to
Paul Grewal:Always. Doesn't matter how senior or a seasoned you get. That's always still the most important call to make.
Khurram Naik:You know, I'm curious. In your story so far, I haven't really heard you talk about the role of mentors and talking about models for decisions. And 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 look 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 fundamental values. But to be super clear, 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 took a leap of faith when they came to The United States. 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 steeps of Northern Minnesota, probably wondering what the hell he just decided to do when he came to The US for school.
Paul Grewal:And eventually, my mom and my older brother showed up after that. You know, and I think to the leap of faith that he and my mother had to make, deciding between one amazing opportunity in a legal career in The US versus another seems somewhat childish, right? It's just like, Oh, do I be a federal judge or go be a law partner? Or, Oh, do I go be a law partner or go be a chief legal officer? Hardly the challenge that the people closest to me have had to confront several times in their lives.
Paul Grewal: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 and impact on me in ways that I mentioned, but, you know, continue to stay. And so that's always been an important touchstone for me in thinking through new opportunities. I don't expect to be, like, giddy and on Cloud9 every day. In fact, most days, you know, these jobs that you and I and others do are super hard. They're stressful.
Paul Grewal:They they 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 at what I'm able to accomplish? And so assessing that potential has been an important framework and milestone for me as I've thought about new career opportunities.
Paul Grewal:And then, you know, I think another thing that really helps is I've never, I've tried to never assume or presume, Quorum, that I get another day or another week or another year in the future to reassess or reconsider a choice that I have. I don't wanna 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, there's just a bus on a street corner waiting to run me over, or 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 gonna go do it, even if it means I'm gonna stumble and bumble, along the way.
Khurram Naik:Well, it's totally fair that, you know, compared to, say, your parents, you know, the the magnitude of the decision they're making in the different outcomes that pales in comparison to the privileged position of this great opportunity or this great opportunity. But in the position of of having those opportunities, how did you did you look to any other guideposts? Did you see, like, other like, say, I'm thinking particularly for the move from Facebook to Coinbase, you know, from from an AGC role to a GC a CLO. Then, you know, were there people that had taken similarly moves with the you use the word asymmetric bet, you know, Similar asymmetric bets that either paid off or didn't pay off that you look to for, okay, that's a gut check, that's something 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 the peak of their careers, but really in the heart of their careers, And had gone not back to a law firm where you largely sat in a corner office and gave advice about what your former court did or you did mediation.
Paul Grewal:As a working professional inside of a corporation where you're subject to performance reviews and bonus assessments like everybody else. You know, there are a handful of judges who have done that, but certainly very few had done that by going into tech, which was 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. 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.
Paul Grewal:And, you know, again, applying some some pretty simple, maybe even too simple, 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, regardless of how it turns out? And then the other thing for me, Haram, has always just been like, I've you know, the lawyers, especially who I've 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 I've just while I've respected the heck out of the lawyer who goes to a fancy law school or not so 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.
Paul Grewal:I 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 in each of those circumstances. So that was always, for me, what defines success. And so that's been useful in sorting through different opportunities at different points in my career because, you know, the fact that I'd been successful in 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
Paul Grewal:I do.
Khurram Naik:Angles to your post. Is it possible to have a rewarding career a rewarding legal career and not love law?
Paul Grewal:Yeah. I mean, I think you and I probably know, between the two of us, dozens, hundreds, thousands of people who, from the outside or on the surface, are enjoying all kinds of rewards from the practice of law, financial rewards, rewards in terms of prestige, 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?
Paul Grewal:Or even if they're happy enough, are they as happy as they could be? Was their work meaningful? Did actually accomplish things that mattered? In some cases, answer is yes. And those are the people that I tend to admire and enjoy being around the most.
Paul Grewal:But in many cases, 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 look back with no regrets. And, you know, we've talked a lot about my successes, and am I'm grateful that you have focused on a number of them.
Paul Grewal:But I've stumbled and fallen in many different ways. You mentioned, you know, the judgeship that I had as a magistrate judge. Well, what we didn't talk about is I was at one point considered for a district judgeship and had my proposed nomination pulled, you know, at the very last minute. That was devastating to me. It was embarrassing to me.
Paul Grewal:And yet, I had to pull myself back up. We didn't talk about the fact that, when I went to Facebook, about eighteen 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.
Paul Grewal:That was frustrating. That was challenging. And, you know, more recently, you know, I've won a few cases, we've done pretty well in some investigations here at Coinbase, but we've also lost others. And I've had 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 a way that they had hoped for and frankly expected. So, you know, I'm stumbling along the way as much as anyone.
Paul Grewal: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 equity partners over the years who are talking about some entrepreneurial move that they've observed, maybe me, maybe in someone else, and said, oh, I thought about doing that at one point. I would like to do that, but they're just, I don't even know if it's necessarily financial and 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. Some people, it may just be like they've got a certain lifestyle they need to continue in finance, and they're worried about their ability to do that in the short or 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.
Paul Grewal:And with that comes a certain status, with that comes a certain amount of deference. But most importantly, with that comes is 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 you don't even know what it is you're aiming for. I mean, that's the life of most entrepreneurs I know.
Paul Grewal: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 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 inspired and impressive as a practice law can be, it just barely, barely scratches the surface in terms of all the other things that talented people can do in this world if they just set their minds to it.
Khurram Naik:And tell me about, 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 is something just it's just innate, someone's disposition, just the way that some people are inclined to be in the outdoors or whatever, just some people just happily drawn to that or whatever, or drawn to the arts or something like that? You know, of course, with any of this, of course, it'd be cultivated, but we can say largely speaking, some people are just more driven in a certain way and just that's how it is. Like, do you think that risk thing is a cultural issue that could be mitigated, or is it just inherent in people and just some like you take risks and some people don't?
Paul Grewal:I think what you're ultimately asking about is classic nature versus nurture debate. 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 their professional life and their set of professional opportunities. But I think there are important ways in which that instinct or maybe even that talent, if I can use that word, can be developed and nurtured. One of the things I think that of amazes me, Cora, on this, if you think about it right, think about how we recruit and attract people to the practice of law. If you look at the sort of amazing range of experiences and interests that defines the entering class of every law school I'm aware of, right?
Paul Grewal:And the fact that we encourage and really prioritize a wide range of diverse interests in selecting 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 special and ultimately churn out a very similar profile, for the most part of a finished law student product. And then from there, it only gets worse.
Paul Grewal:Right? Think about 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 a successful accomplishment in a way that sort of standardizes that in ways that looks very different 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 will have to make, you know, are really, you know, choices that are extremely similar and really don't vary very much in terms of risk or potential downside.
Paul Grewal: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 and even if that's too abstract to really kind of engage with, again, I come back to our own families, our own stories, our own histories, where and almost every one of our own family's story, there are challenges that make the difference between big law firm A and big law firm B look comical. These are not life altering choices. So I just think having an understanding of history and appreciation is also something that's really, really important.
Khurram Naik:When you talk about risk, it seems to me that you've been taking risks with these career leaps, this all in risk 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 ways of doing something on the side of some kind that 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, opportunities?
Paul Grewal:Yeah. I mean, a thousand ideas come to mind. Right? So a small example. You know, I think of risk and and exposing yourself to new people, new ideas as, maybe the most important element of of of developing a different approach to career choices.
Paul Grewal: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 ten days when you're, you know, a hardworking, you know, law firm associate and sitting on a beach and relaxing in a way that you totally deserve and have earned, maybe spend that week or ten days of vacation taking a pottery class at your local community college, where the people you're gonna be interacting with are gonna be very different, by and large, from, you know, the people who tend to go to the same resort and the 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 an extra year on that lease and then taking the amount of money that you would've spent on the additional rent and dabbling in a little bit of real estate with 10 of your friends, you know, by starting with, you know, a 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.
Paul Grewal:You know, there's just a thousand different examples like that. Maybe it's instead of, you know, billing twenty four hundred hours a year at your firm in order to qualify for the next level of bonus. Maybe it's only billing twenty two hundred 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 two hundred hours a year on 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 that a lot of people think about.
Paul Grewal: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, 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 realize like, no. There are all kinds of different alternatives out there. It's just you have to take the blinders off sometimes.
Khurram Naik:You talked about exposing yourself to people with different sets of ideas. And I'm struck that when you're, say, the story that you're telling up at The Mastery Judge is that more than one friend came to you with, hey, there's this opportunity that could be a fit for you. People knew you so well and wanted to help you. How have you cultivated that quality of friendship relationships? And what role has that set of relationships played in your career?
Khurram Naik:Well,
Paul Grewal:I'm actually gonna focus on the word friendship that you use. I think 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, have a responsibility to our partner or certainly to our children and to our parents. And so I think that's generally well understood, and some of us are better at that than others.
Paul Grewal: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'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 in my personal and professional life, I've tried to resist that.
Paul Grewal:I tend to be friends with a lot of lawyers. I like hanging out with lawyers. I like people who practice law. Although not exclusively, know that those tend to be my people. And throughout my career, you know, one of the things I've been proudest of is whether it was when I was a law clerk or a young associate, even on the bench.
Paul Grewal: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 I've, to varying degrees, remembered even when 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 my career, I think that the fact that I've tried to be as helpful to my friends, and even people I wouldn't consider friends, but that I've just come to know, and 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, try to help other people navigate this this hard, crazy life as best as they can. And on occasion, sometimes I suppose that does come back, and I've been grateful for when it has. But I don't have that expectation.
Paul Grewal:I don't think any of us should have that expectation in any of our successful friendships because it just, I think, is something that is much more valuable in a giving than in a receiving, I guess is how I would put it.
Khurram Naik:And I understood you saying, your comment about the ways in which you think friendship is neglected. Because my understanding is that's the kind of stuff there's family, which is well understood. And I think investing in, say, professional relationships like, hey, I'm part of a bar association or something formal, informal, investing or client development, I think those are well understood or discussed as well. You can go take a course on family stuff. There's lots of support for that religion, lots of support for family related things, lots of support for networking and professional stuff.
Khurram Naik:You know, you can we'll take a course on business development. We hire a Yep. But relatively little in the way of, hey. Here's how to focus on your friends, and here's reminders on on friends. So that that's the it occupies this value between those two is how I'm hearing you talk about this.
Paul Grewal:Yeah. And it's the hardest thing because especially for lawyers because we have pretty demanding schedules and lives. Right? So professionally, personally, there often isn't a lot of extra time or extra emotional space for time with friends or commitments to friends. And yet, maybe I'm getting a bit more philosophical as I get older and reflective as my children move through school and ultimately out of the house into their own life, that you ultimately have a chunk of life professionally and personally where friendship is really all you have, whether you have a life partner, whether you have an extended family or not.
Paul Grewal:Because interesting that when we're younger, when we're in school, certainly in high school and even in college, friendships are so central to how we spend our time and whatever joy or satisfaction we get out of the goal. And yet I think that's as or even more true much later in life. And yet I don't think we make necessary investments along the way necessarily that set ourselves up for success. And I'm trying to resist that and avoid that, again, with varying degrees of 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 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 that said, it could have gone one way, it could have gone another, I went this way, but I'm not sure I made the right call.
Paul Grewal:Yeah. I well, I'll start with a professional example. I don't know for sure, Hram, 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 of my labor day in and day out. Right?
Paul Grewal: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 are 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?
Paul Grewal:I don't know. And, you 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, I don't tend to be someone who dwells on it only because, like, in many ways, those are unknowable questions. Right?
Paul Grewal:You just 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 would not 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 seventies and eighties, 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.
Paul Grewal:And a part of me thinks a lot about the implications of that decision on the ways I've been able to spend time with my family and the connections I felt to my local community. I've essentially been living this immigrant life in California now for twenty plus years, I've never really felt at home here. So I think a lot about those choices as well. And yet, you know, I think if you dwell on them too long I think it's important to be reflective, but I think if you dwell on them, you ultimately end up right back 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, 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 funny because last time I saw you, we were at a conference and you're in workout gear. You're the chief legal officer of highly there's a a tech company with a major regulatory component, you know, just so the bleeding edge of of 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 tell me some more about that.
Paul Grewal:Well, you know, I've been now living here in California for roughly twenty five years. I've lived here longer than I've lived anywhere else. And yet, like, think a lot of immigrants feel, even though you may have spent decades in a place, if you are 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 as true for me here in the Silicon Valley as anyone else. I appreciate that I present in a way that suggests I have overcome, you know, those obstacles.
Paul Grewal: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, you know, 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 what I see of 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, this so you've met my wife a couple of times, and she's got a question for you that I think is good. She says, look. You're you're you're in California at this, you know, this crypto company. There's gotta be something that's woo woo about the guy. There's something woo woo about him.
Khurram Naik:So what is what is it? What's the most woo woo thing about you?
Paul Grewal:I don't know. I hate to disappoint her. I'm a pretty dull guy in many ways. I don't know. I suppose it's a little off base for me that I don't shy away from the darker corners of the internet in terms of In my professional job, especially in cryptocurrency, I have to spend a lot of time on Twitter.
Paul Grewal:I've spent a lot of time on Discord. I have to spend a lot of time in subreddits. And as many of your listeners will know, those those portals can take you to some very crazy dark places, particularly in terms of conspiracy theories and all kinds of rank speculation about who's running the world and what's the secret government behind the government. 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 not a lot of people would guess about me.
Khurram Naik:What's a conspiracy theory you can't shake?
Paul Grewal: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, 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?
Paul Grewal:Absolutely. And would it surprise me or shock me to learn that if there was, you know, contact with that extraterrestrial life that one or more world governments would, you know, being incented or inclined to try to cabin or limit, you know, our understanding or knowledge of that? No. I wouldn't be. Maybe that's something I'm a little woo woo about.
Khurram Naik:Yeah, is interesting. I fully abide to all the premises that you just laid out there. My only question there obviously, by definition, if anybody is hiding something, by definition, you don't know what's being hidden from you. But of course, over time, some things leak out, right? Some things leak out of some kind.
Khurram Naik:Things like one secret are no longer secret. The Tuskegee experiment, these kinds of things were one secrets and then Sure. But I feel like there's just like, using this, like, say, physics or chemistry metaphor of an equilibrium where if something is just that 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. There's something that's potent. It's just too powerful a thing to keep hidden.
Khurram Naik: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? If you haven't, how can you make sense of the most incredible like, if someone was sitting on that information, the unbelievable incentive and motivation you would to tell everyone, here's the craziest thing. There's extraterrestrials and and Yeah.
Paul Grewal:Well, I I I would say a couple of things. One is I'm not necessarily saying this is probable. I am saying it's plausible. It's and most definitely possible. And I think the other thing is that when it comes to extraterrestrial life, as one example, right?
Paul Grewal:I think again, yes, 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 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. You know, without being too morbid about it, I think there are plenty of examples, even in our recent history in the twentieth 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 incented to wanna make that as publicly known as it should be. How's that for woo woo?
Khurram Naik:That that satisfies woo woo, I think. I'm always satisfied that that's woo woo. Well, look, you you really love Loring, so I don't wanna to miss out on that. But so I wanna pick up on that shortly. But you mentioned social media, we can start from there.
Khurram Naik:So tell me, you know, you're you're highly active on social media. You you've got, like, 50,000 followers on Twitter, something like 25, more than 25 on LinkedIn, so 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 I think so many lawyers are very averse to being active on social media, particularly, I think, as somebody who I think another lawyer who is in a company that faces such regulatory scrutiny might be even more averse to having a public face and just making sure that every minutiae is adequately messaged and lawyered. So tell me about I know risk has been a running theme, and so maybe that's just that's the simple answer.
Khurram Naik: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 and interest in social media goes back well before my time here at Coinbase. After all, I did work for a social media company of some repute for several years immediately 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 and and elsewhere.
Paul Grewal:And it was largely because I I was just, again, curious and interested in how these new technologies could reach different audiences and allow you to have a 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 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.
Paul Grewal: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 or, you know, just deal with the day to day struggles of the job. And so, I have, again, found that, by sharing sort of how I've looked at things or or or lessons that I've learned, Certain people have found it, you know, useful and interesting in their own work or in their own lives, and and that's very gratifying. But mostly, you know, it's it's not some grand, you know, 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 chill a little time on brewing my coffee in the morning and there's nobody in my house to talk to because my children and my wife have left for the day, and I just need some other person or group of people to communicate with.
Khurram Naik:Why is it important to message? You have an outlet for if there's changes you need, you need the SEC to make to to 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 Whether know, 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 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 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 of the ways in which a conversation has, taken off in unproductive and even harmful directions.
Paul Grewal:But in my experience, from, like, day in and day out, I have a wonderful, you know, experience and incredibly valuable conversations when I engage on Twitter or a 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 in crypto, about the legal profession that we all work in, and I think that's a generally good thing.
Khurram Naik:Mhmm. And has there been any, you know, same question I've asked you about these different roles. You had expectation for things you learn or relationships you make. What were surprises along the way? What's something that you've been surprised to learn about in the course of being active in social media and building such a large following or 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? There's an old trope on the internet that when you're on the internet, nobody knows that you're a dog. Right? There's famous New Yorker cartoon to that effect.
Paul Grewal:And I just love the fact that 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.
Paul Grewal:Right? Where'd you go to school? Who'd you clerk for? What firm have you worked at? Is the company you worked for a Fortune 100 company, or is it a company I've never heard of?
Paul Grewal: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 wouldn't garner a lot of attention in traditional places and spaces in the law.
Paul Grewal:And I think that's awesome. I just feel like that's a much fairer and much more interesting way to operate and way to live. And so that 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 where all lawyers What are reasons 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.
Khurram Naik: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. But 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 the kind of person who should be lawyer, who should be more active on social media?
Paul Grewal:Well, 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 I 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 actually to say? Right? Like, I'm sort of one of my pet peeves about lawyers on social, but also in communicating more generally, is that more often than not, they sort of skip past the do I have something interesting to say question and focus on how do I say it. So I think that is where I would begin and urge others to begin.
Paul Grewal:And then I think that at the same time, and this touches upon 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, though, there's something interesting happening in just about every lawyer I know's lives 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? Right? So that's the piece, I think, that sometimes people miss, right?
Paul Grewal:It's 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. 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 as true for social. Less is generally more. 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 the story of Coinbase and what it's looking to do is is essential. And I think, of of course, it's been common for common or maybe not common, but valued among high performing tech companies are companies where founders have a clear message. And so I think that's something that Paul Graham has underscored for a number of years is the storytelling component and Yeah. 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.
Khurram Naik: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 clearer to clearer to me, you know, over time. And this is true whether it's, you know, a LinkedIn post. This is true whether it's a closing argument in a Federalistic Court trial or anything, you know, in between. I think the most element the most important elements of a of a great story are the people, the characters.
Paul Grewal: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, you know, 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.
Paul Grewal: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 about a tweet, you know, a novel, or or anything else that you might compose. And I suppose one other, you know, element of storytelling that I try to focus on is, am am I offering something new or fresh, either as compared to what I've said before or what others are saying? Because I do think that, you know, as humans, we are we are wired to the novel.
Paul Grewal:Right? We're we're 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 that you don't look to tell people what to do, and I fully appreciate that. But I'm curious for you. I mean, I feel like there's so many there's recurring in the practice of law, there's, like, recurring scenarios that lawyers find themselves in, and especially for the reasons that you identified where so much about the legal training in law school within 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 key junctures of their career to make decisions.
Khurram Naik: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 wanna keep on, you know, the practice here I'm in, and, I don't know if I wanna make part of my firm. I don't know if I wanna go in house. I don't know if I wanna do something completely different. I'm sure you get you know, run to people like this all the time.
Paul Grewal:You know? What do you how how what what do
Khurram Naik:you say to someone? And I recognize it's 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 through that canonical issue that a lot of smart people find themselves in?
Paul Grewal:Well, gosh. There's all kinds of advice out there on this topic. So applying my own standard that I just articulated a moment ago, maybe maybe I'll focus on what maybe 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.
Paul Grewal:What are you really good at? Like, I ask 10 of your friends or 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 gonna tell me? What are they gonna tell you? And I start with that because, again, this is just sort of the way I've thought about my professional career.
Paul Grewal: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 aspire to. And so it's not the be all and end all to, I think, the very important and hard questions that you know, I I do get asked and that people, I think, confront for themselves and their own careers over and over again. But really being candid and honest about what you're good at, I think, is something that a lot of lawyers overlook. Again, I think a lot of us imagine us to be very good at certain things we're not actually very good at and completely overlook or ignore, you know, areas where we are extremely talented and accomplished, but, you know, are so second nature to us that we don't really focus on. That's that's maybe a different way I I I look at that question than than some other people.
Khurram Naik:I really like that. So now I'm going to apply it to you. But with your two audiences, so as you said, you like associating with lawyers and you've got plenty of content with lawyers. What do you think the lawyers in your life would say for you? What is it that Paul Grailwell 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 witness broke down on a witness stand, or where a juror would lie to my face about why they couldn't serve, 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 the things of which 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, you know, 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, only after we resolve the situation or put something to rest.
Paul Grewal:I think those experiences, that talent is probably what I'm best at relative to my peers, as much as, you know, my ability to write, my ability to speak, my ability to think about legal issues, that sort of thing.
Khurram Naik:Okay. That's good. And then I want I want and that that definitely ties into running themes you've been talking about about, you know, those those are notable moments, like stepping into the mastery judge role, is managing the emotions. That was a key part of your role. That makes a lot of sense.
Khurram Naik:But now I'll ask a question So in now you report to a board of directors, and these are people like Marc Andreessen, Fred Wilson, Toby Lutka, people that are successful software entrepreneurs, GCs.
Paul Grewal:They are.
Khurram Naik:So what would that audience say is your is your alpha 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 gonna get past 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 as much as anything 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 do they approach decisions differently than skillful lawyers, jurists? You know, what what can we learn from from from that group? You fewer of us as lawyers have contact with people in those roles, and we've had a lot of success in different domains that require different kinds of decision criteria. But what can we learn as lawyers from that group?
Khurram Naik: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. That'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 role, I think, also qualifies on that score.
Paul Grewal: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, have 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 outsized risks when they are convinced that they are right.
Paul Grewal: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, have been impressed that, you know, the people that I've worked with who sort of did that bill that you just described really do care deeply about the wider world and what kind of world they're gonna leave behind when they leave. And, you know, I can appreciate there may be some skepticism around that. And these are not saints by any stretch.
Paul Grewal:They're just as human as the rest of us. But there is a, 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 that 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've seen.
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's data points for, you know, what makes Paul make a move? What is it that Paul is looking to level up on? And I think extrapolating from here, you know, you're already in you're in the chief legal officer role at a company that's had a lot of success financially and, you know, and that's, you know, benefited you personally. And so so I think that dimension sounds pretty seems pretty sound. You're working on cutting edge legal issues.
Khurram Naik:It'd be hard to imagine something that would be more at the forefront of public disputes with a regulatory body and trying to be on the side of what you think is right. So it'd be hard to top that. It'd be hard to top what company could give you more challenging legal objectives to attain or compensate you or reward you in some way more significantly for that. So I feel like that's gotta be hard to top. So it's gotta be something else.
Khurram Naik:Right? And so maybe obviously, it would be, you know, flexibility. Maybe you you you worked as hard as
Paul Grewal:you can.
Khurram Naik:I suspect that's not true. You're a very spry 51 year old. So no, I don't
Paul Grewal:52 as of yet. 52 as of the day before yesterday, just to be clear.
Khurram Naik:Turn it off. Okay. So it can't be that. So I wonder if the answer is maybe it's something along the lines impact. So I think that's the thing.
Khurram Naik:If there's anything that seems close to regret, if you want to put it that way, it's looking back and saying, what would a life in the judiciary have been? Because the range of impact you could have on society is very stark. So it could be something that generates a lot of impact. I don't have an answer, so I'm not going to speculate. But I'll ask you this instead.
Khurram Naik:I've observed that there's certain 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 recently Jason Kwan of OpenAI moved into the chief strategy officer role at OpenAI OpenAI. And then you've got, Gordon Moody who just moved into the chief product officer of part of a legal, AI startup.
Paul Grewal:Yeah. Brad Smith at Microsoft, former GC, now the president. There are, I think, many examples like that for sure.
Khurram Naik:There there certainly are 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 for you to make that attractive for you? Or what do you think it makes it attractive for?
Khurram Naik: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 less important than the title or sort of the organization is the problem set collection and of challenges that, you know, I would have an opportunity to engage with that kind of opportunity or with that kind of opportunity. I just think that, you know, one of the things that, I really am proud of as 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.
Paul Grewal: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 it could serve them very well in other roles that go well beyond the law. So, you know, I do think, though, that 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 generally embrace a certain degree of humility that there are lots of things out there that we don't know. And also just sort of be 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, could do very well in any of the other roles. Of course, haven't even talked about all the things outside of, as I said, corporate life, where I think lawyers bring a lot of unique experiences and attributes that could could lead to some amazing success.
Khurram Naik:It'd be hard to think of a better point to stop at than that. I feel like that's a really good summary of themes in your life and and your career. So and and, yeah, that's a that's a that's a great place to stop right there.
Paul Grewal:Awesome.
Khurram Naik:Well, Paul, thanks for taking the time. Happy belated birthday.
Paul Grewal:Thank you. I appreciate it, Hormad. This was a fun conversation. I appreciate your, you're having me on. I've enjoyed it.