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Paul Grewal
Chief Legal Officer & Corporate Secretary, Coinbase Global

020 Paul Grewal: asymmetric bets, conspiracy theories, and the best question for career decisions

🎥 Oct 01, 2023 📺 Khurram Naik ⏱ 113m
Paul Grewal is the Chief Legal Officer at Coinbase. As the highly visible head lawyer at a company perennially making headlines, much of Paul's story and approach is well-known. This interview explores the lesser-known aspects of Paul's career moves: how Paul thinks about risk, the key question to ask in making a career change, and a conspiracy theory he can't shake.  (09:12) - the financial and emotional changes in leaving practice for the bench (15:30) - the most challenging part of being a judge (22:10) - the most skillful advocacy he observed (48:27) - what made Coinbase an asymmetric b...
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About Paul Grewal

Paul Grewal, Chief Legal Officer of Coinbase, has been discussing the company's legal strategy and the broader regulatory landscape for cryptocurrency. In an interview, Grewal stated that Coinbase's approach to crypto involves following the law, building a licensed and regulated exchange, and advocating for rules, including suing the government when rules are not provided. He also expressed concern that public service is increasingly viewed as a burden, potentially deterring talented individuals from serving. On Coinbase's Q1 2026 earnings call, Grewal expressed confidence that a piece of legislation called "Clarity" would be signed by the end of the summer, describing it as a "significant unlock" for the industry. He noted that the bill would provide regulatory clarity on issues such as rewards and would allow Coinbase to build new products and services. In a separate keynote discussion, Grewal predicted that tokenized equities would be a major topic in 2027, citing an anticipated innovation exemption from the SEC. He also described a White House-led meeting where lobbyists for banks and crypto representatives were brought together to negotiate.

Source: AI-verified profile updated from Paul Grewal's recent appearances. Browse all interviews →

Transcript (100 segments)
H
Host0:00
This is Horum with Horum's Quorum. My guest today is Paul Grewal, the chief legal officer at Coinbase. This is one of those interviews that builds and the pieces all come together. I think even people familiar with Paul's story will walk away with a deeper understanding of what makes Paul tick and the first principles reasoning he uses professionally. Here's Paul.
P
Paul Grewal0:21
Great to see you. Thanks for joining.
H
Host0:23
Great to see you as well. Thanks for having me. So I want to hear about, we talked last time about your workout routine, and I know you said you've been very consistent with your workout routine for a number of years, but I'm curious, what is your workout routine today, and how has it changed over the years?
P
Paul Grewal0:40
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, mix in a little weightlifting, and then if I can squeeze in a round of golf or a walk or a bike ride, it's been a pretty good week for me.
H
Host1:08
And is it usually first thing in the morning?
P
Paul Grewal1:10
Yeah, for me, if the workout doesn't happen at the beginning of the day, it just doesn't happen. So I'm generally a pretty early morning person, 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.
H
Host1:33
Yeah, I love that. And so, has it changed much at all over time? Has it just been kind of the same formula?
P
Paul Grewal1:39
Yeah, it has changed. I think as I've gotten older, I've probably gotten better at being more consistent. 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. And then the other thing is, as the body ages, a couple things happen. 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 10 seconds off my 5K time or whatever the case may be.
H
Host2:26
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?
P
Paul Grewal2:35
Yeah, I've dabbled with meditation. I certainly do a fair amount of yoga. I've never been a dedicated mindfulness practice kind of guy. I have not been one who has been a regular attendee of religious services. So a lot of the things that a lot of people do that I think work really well for them have never really caught fire for me, even though I've always been a dabbler, always experimenting with something new, always trying to find a new angle to get a little peace and calm in my day, especially before things start to get much less calm and much less peaceful.
H
Host3:14
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 maintain a pretty even keel and don't tend to get too elevated. And I know you're a former litigator. I think you know how elevated some people can get in that space. So how do you do that then if you don't have some sort of mindfulness practice or something similar to that? What is your approach or principles? How is it that you're able to maintain this more or less even keel?
P
Paul Grewal3:48
Yeah, I like the word elevated. I'm going to 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, part of it is just my nature, the way I grew up, the way I've kind of approached things outside of the practice of law that's probably given me a bit of center and focus. At the same time, I try to eat right, I try to sleep right, try to exercise 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. My first priority in most situations is to figure out what we need to do.
H
Host4:39
Yeah, that's good. Well, I thought that with that in mind, I feel like your story, lots of aspects of your story are well known. I mean, you've got a very substantial social media following. You've done a number of interviews over the years. I think a lot of people know your story in large part. I thought this would be an opportunity to get into all the other bits of your story that I think are less known. What are the other aspects of your life that have facilitated the decisions that you've made? So maybe we'll start with a contrarian version of your story and start out with your experience. We can jump around chronologically. I know your clerkships have been important to you. We can double back to those for sure. But let's say you're a law firm partner and you're trying to decide what comes next for you, and then somehow you make a transition to a magistrate judge. Now I think a lot 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?
P
Paul Grewal5:46
Well, one thing that I think sometimes gets confused, at least when it comes to my decision to become a magistrate judge in 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 I had a rough sense, a nagging feeling, an instinct that I would enjoy service as a judge. And I certainly had in the back of my mind so many of the positive formative experiences I had as a law clerk, not once but twice earlier in my career, seeing how judges worked, what they did, but most importantly, what satisfaction they took from their day. I think that was the thing that stuck in my mind, that for all the amazing and impressive lawyers and others I'd worked with up to that point in my career, the two people who I really felt relished their day more than any other and really seemed to appreciate what they were able to do day in and day out in their professional life were the judges that I worked for. 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.
H
Host7:07
And then, you know, you definitely had the qualifications to be a district judge. Why is it that you accepted or went for a magistrate judge role?
P
Paul Grewal7:19
Because that was the opportunity that was given to me. It was pretty simple. When I applied to be a magistrate judge, I want to say I was probably 38, so relatively young. Not the youngest ever, but relatively young. 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. In a very hierarchical structure like the federal courts, we naturally think about the Supreme Court justices first and foremost. They probably occupy 90 to 95% of our mind space. They certainly consume 90 or 95% of the conversation and oxygen in any room of lawyers. But in the lower ranks of the judiciary, there are incredibly talented people doing incredibly important work. And just as important, at least from my perspective, they have incredible opportunities to be very creative, to do a lot of good for real people in real cases, but also to expand their professional skill set and have an impact on the world in ways that I think are relatively underappreciated. So as I thought more and more about what magistrate judges do, what I might be able to do in that role, 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 in the hierarchy to warrant professional praise and command respect that we all want, even if we're not always 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, and I was ready to do all that.
H
Host9:41
Tell me about that. I think that's really huge and I think a major obstacle for a lot of people at every level to making 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 you were set up? How did you know you were equipped to make that work? And what were the tangible things that you did to put yourself in that position?
P
Paul Grewal10:06
Yeah. So let's start with the financial because in some ways that's more straightforward, more mathematical. At the point I became a magistrate judge, I had been an equity partner in an Am Law 100 firm, the Howrey firm. It no longer exists, but in its day was well respected and was a place where I learned a lot about practicing law. As a rising partner, starting to attract clients and really interesting cases, I was at a point where I could afford a mortgage, I could afford private schools for my kids. I was fortunate enough and remain fortunate enough to be married to a working professional, and that provided a certain amount of flexibility as well. And at the same time, as a lot of us struggle with, as income rises and resources grow, so too do our appetites or tastes and our preferences. 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 modest lifestyle that reflected the way we earned and worked maybe five years before or even 10 years before, even though things continued to go better and better for us in our careers. 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 financially and otherwise to take the 91% pay cut that was required in order to pursue that opportunity and at the same time have a certain amount of confidence that things were going to be just fine. There were plenty of people who did just fine living on the salary and compensation package of a junior federal judge, especially with a working spouse. So that helped and 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 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, and inside of a law firm, as a partner, you really are the center of that universe, to a place in the courts where, as I said, literally I was the youngest, the most junior, certainly the least known judge, not just in my court, but certainly nationally or on a broader scale. So you had to adapt to, 'Oh right, this is like taking any new job. I've got to start at the bottom and I've got to prove myself.' Once I sort of put it in those terms and really treated it as no different than when you get that first job working at McDonald's or as a junior associate or in whatever other situation, it just became easier for me to adapt and steel myself for that learning curve that comes with any new opportunity.
H
Host13:41
And then in that role, what were the skills that you probably had a set of skills that you came in expecting to hone? So maybe you can tell me about 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?
P
Paul Grewal13:57
Yeah. So for judges, at least as I thought about it, it's relatively obvious you have to be pretty good at understanding how to take apart a case. You have to be pretty good at analyzing complicated laws, sifting through messy, imperfect records, weighing and deliberating on credibility determinations. All that stuff, I think, is relatively well understood. And 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 thrown out onto the bench and thrown into a criminal law calendar where I had very experienced assistant United States attorneys and equally experienced federal public defenders, all there to do their job and all expecting me to know what the heck I was doing. So there was a lot of learning by doing and, 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. But part of the job where I felt like I didn't appreciate what skills were going to be required in order to be effective and ultimately successful was managing the emotions of the moment. In any dispute in court, whether it's a fight over a software license or a decision as to whether somebody's going to spend the next 13 months awaiting trial in jail, all of those situations require a certain ability to navigate some pretty complicated emotions in the room. Those emotions stem not just from the parties. It's pretty easy to understand why a criminal defendant may be a bit agitated or elevated, as you referenced earlier. But the lawyers, they're worked up. They've got a range of emotions to work through. If you're picking a jury, you've got a bunch of people in there who don't want to be there and for the most part don't understand what's happening. They're confused, they're anxious, in some cases they're a bit nervous. 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 Supreme Court precedent or resolving conflicting witness testimony.
H
Host17:08
So what were the techniques that you learned over time? How do you manage people with strong opinions and strong feelings?
P
Paul Grewal17:19
Well, I mentioned one thing that I think is at the root of my approach, at least my intended approach, because I fall short of this ideal every single day. I think you start with humility. I think you start with acknowledging not just to yourself, although first with yourself, but ultimately to everyone around you that while you know a bunch of stuff, there's a whole heck of a lot more that you don't know in almost every case. So I think that was helpful so that everyone understood that whatever their emotional range was at that particular moment in time, I was going through my own range, and so I think it helped to level the playing field in that way. The other thing I think that was very helpful was that 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. 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 elevate their performance, 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 they're just little touches like that that help people feel comfortable in their own skin, and that's one of the things I've tried to do 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 the people around me to be the best at what they're there to do, which ultimately benefits everyone.
H
Host19:36
Well, I think the interesting balance it sounds like you're striking is humility with confidence, because you also have to show, hey, there's a reason why you should be tuning in to me because I will help you here. How did you establish that? How did you maybe avoid the outcome of imposter syndrome? Like, I'm very skilled at IP but I'm not really knowledgeable the way that an experienced US attorney is about criminal matters. How did you establish that authority and ramp up and put yourself in a position where you had that credibility while balancing that humility?
P
Paul Grewal20:10
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, 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. It's a lot like being in a surgical theater. You would be more than a little bit anxious to learn that your anesthesiologist was humble and at the same time lacked confidence in what she 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. So from my perspective, the number one thing that I think has helped is that I've shared my genuine curiosity in what others do. It's amazing to me how in a single day, certainly in a courtroom but I think in many other professional settings in the law, we are just all so privileged to encounter, work with, in some cases work against, some incredibly interesting people who have done some even more interesting things. 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 investigation in a certain way, if you have a genuine curiosity and a drive to want to learn more about what they do and why they made the choices that they make, and then you express and share and communicate that genuine curiosity and enthusiasm for their work and their path, in my experience, most people most of the time respond very positively to that.
H
Host22:00
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?
P
Paul Grewal22:09
The number one thing that I observe that I think too few trial lawyers appreciate is that almost always, the most important questions or the most important arguments are the questions or arguments that you didn't make or didn't pose. I think of great advocacy as ultimately about curation. When I think of great curation, I think of painters or 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. For advocates in the courtroom, the very best were almost minimalist by nature. They figured out the two or three things they needed to ask or the one or two arguments they needed to make and then left a whole lot more on the cutting room floor. That was something I saw and continue to see that is very consistent among the greats.
H
Host23:11
I like that. So then tell me some more about, again with this notion that we're building out the hidden story of Paul Grewal, the things that people haven't heard about, because I think plenty of people heard about your move that excited, surprised, wowed a lot of people from the bench to Facebook. So tell me about the things that people don't appreciate about that move.
P
Paul Grewal23:36
Well, one thing maybe that is not easy to appreciate is that I really, really loved being a judge. I think a lot of us when we make career changes, in whatever form, are moving away from something we don't like or running from something that is bringing us stress or anxiety or just unhappiness. In my case, that just was not true. I hope that I was able to communicate effectively day in and day out when I was on the bench that I really just loved the day-to-day. I loved being in the courtroom. I loved the characters that find their way into a federal courthouse day in and day out. I loved the fact that I had no real idea what I would be working on over the course of the day just given the random and tumultuous nature of most court cases. All of that was fantastic. I certainly loved 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 was a heady, wonderful experience. So it 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? For me, this was not 2016. I'd been serving as a US magistrate 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. At that point in time, I had probably written a couple hundred published opinions. I was very fortunate that in the Northern District of California, where I serve, magistrate judges have the opportunity to try civil cases if both sides consent to the magistrate judge's jurisdiction. I think I was able to do something like 30 or 35 civil jury trials in nearly six years, which was a pretty heavy clip. So I had that experience to the degree that I had hoped for. 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 docket of cases when you sit as a magistrate judge or a trial judge of any type in any federal court. It all just kind of made sense to me. 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, coming back to an earlier theme you were exploring, I had to sort of at that point ask whether I could once again start as a junior person, a new person in a very complicated organization. Facebook was stuffed with super smart, super talented people, and no one was going to call me Judge Grewal when I walked around the campus in Menlo Park. Although one or two did. For the most part, I was just Paul from building 20 or 23. I had my badge with everybody else. I rode my bicycle and locked it in the bike rack in front of the main campus entrance just like every other employee. So fortunately, having made that transition at least once or twice earlier in my career, that wasn't the big deal that it might have been for some other people. I was very comfortable 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 brilliant, even if the other half thought I was the opposite. I was just at that point very comfortable in my own skin and quite willing to make yet another change because I thought I would grow in a different direction. I think when you stop growing, you stop living, and that was really as much as anything what motivated my move to Facebook.
H
Host28:22
Were there other roles that had the same profile, and what was the tiebreaker that made you go to Facebook?
P
Paul Grewal28:30
Well, I hadn't really considered any other role seriously at that point. For me, it was all 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. At that point in 2016, Facebook still largely basked in the glow of our adoration for all things tech. There was still a perhaps naive view that most of the things tech did most of the time were in pursuit of human progress and that tech was a force for good. It was becoming increasingly clear by early 2016 that that view was starting to look a bit naive or simplistic, and the company was about to head into some very challenging legal issues that I would have a chance to play some role in. So that was also super attractive to me. It took maybe three or four weeks after I joined the company in 2016 for that to become abundantly clear, so at least I got that call right.
H
Host29:45
And so then, 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 didn't expect?
P
Paul Grewal29:57
Yeah. Well, at that point in my career, I tried a lot of cases, not only as a trial lawyer but 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. What I had never done though, Coran, was I never led an organization. As a law firm partner, you don't really lead an organization in 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 move forward managing these cases, and in a handful of them you take the cases to trial, and then you break up the band and you look for the next case or the next project and assemble a different team. Even if some of the same characters repeat themselves. That was certainly true as a judge. I had a couple of law clerks, I had a courtroom deputy, and that was about it. Whereas by the time I left Facebook, I was leading an organization of several hundred people. I had 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 managing that complexity, understanding what the business and its priorities were, and making sure that my litigation team, my regulatory team, my corporate team, whatever the case may be, were focused on those priorities day in and day out. I had to manage compensation and performance issues just like any other leader of an organization inside of a company. I had never done that before. Oh, and by the way, I had to go back to a world where I had a boss like everybody else. 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. So I had to adapt back to that world, or really adapt to it for the first time. So there were a lot of skills that I had to develop that were new and certainly challenging for me.
H
Host32:34
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 the decision to do that?
P
Paul Grewal32:59
Well, look, I think one thing that was very consistent in my move to Coinbase with my move to the court and even my progress in my firm life before that was I've always been a huge believer 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. So I only applied to be a magistrate judge when I felt confident that I could not only do it, but do it very well. And the same was true when I went to Facebook to take over litigation. And then with time, other areas of the legal department fell to my responsibility. But in each of those cases, I was not the top dog. I was not the number one. I was not the district judge or the Ninth Circuit judge or Federal Circuit judge in my time on the bench. When I went to Facebook, I was not the general counsel. 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. For me, that was something that I finally felt I was ready to do, having led a complicated organization at Facebook dealing with a whole range of super messy issues for the company, everything from Cambridge Analytica to all sorts of different class actions involving data privacy and intellectual property and regulatory fights with the FTC and elsewhere. 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 asked about what may have been less obvious in all of that. Well, I think a lot of people, 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 the ideological or other underpinnings of Bitcoin and 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 an FBI agent looking to seize some Bitcoin in an investigation. This was back in like 2012, maybe even 2011. It was early days. But I had not immersed myself in that universe and I was not 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. I've just been a huge believer as a lawyer that it 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, the major opportunities of the organization are all grounded in law. Because at that point in time, you will not only be an important part of the work, an important voice in the conversation, you're also going to be uniquely positioned to assume leadership. 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 to-do list this morning in 2023.
H
Host36:46
Well, jumping back to Facebook, the decision to join there. Your role now, the role of resolving regulatory issues seems to be essential to the business. The overlap between product and your role is huge. That seems to be less the case at your role at Facebook. So what made you take the leap to Facebook knowing that IP issues weren't at the centerpiece of the organization? What made you think that you were going to scale up and level up from that move? Aside from the company's trajectory, what made you think that that function was good for you?
P
Paul Grewal37:35
Yeah. Well, I actually think in 2016, litigation and regulatory issues were about to become fairly existential for Facebook in a way that wasn't true before. To my knowledge, Facebook had only had one jury trial up until that point. It was certainly true that Mark Zuckerberg had never testified in any court case. If you fast forward just 18 months after I joined, when the Cambridge Analytica scandal blew up, suddenly Mark and others were being hauled in front of Congress to account for and explain what happened. So the function was absolutely central to the company's future, even if it wasn't as visible at the time. And I saw that coming.
Those were all very novel experiences that proved to be quite searing for the company. As it turned out, what was once a quieter function, because Facebook's always had its share of litigation and regulatory investigations, became a very public and strategic challenge for the company. That necessarily meant that things I was working on, like helping to put the Cambridge Analytica situation to bed, or making sure that when we went to trial in these billion-dollar cases, 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, given how much the company has changed over that period of time.
H
Host39:10
And can you be a little more specific about how you came across that opportunity? Did Facebook approach you directly? Tell me more about that, because it's kind of unusual for a magistrate judge, I would think, to be approached by a company. Tell me how that happened.
P
Paul Grewal39:29
It's pretty unusual. We don't have on-campus recruiting in the federal judiciary, so it works a little bit differently than many young lawyers would be more familiar with. For me, as I think back to it, a number of my friends who were still practicing law told me in late 2015 or early 2016 that Facebook was looking for a new kind of leader. 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, particularly when it came to courtroom advocacy and strategic planning and direction setting throughout some very intense regulatory investigations. When my friends mentioned that Colin and the leadership beyond Colin were looking for this new kind of leader, the more I thought about it, the more intrigued I was. I realized I presented a somewhat atypical or unusual profile. But if they actually came to learn my story and what I could do and what I had done, maybe they might be interested. At their encouragement, I reached out to Colin. We had a cup of coffee, and just like so many jobs and opportunities for all of us, one cup of coffee led to a lunch, one lunch led to a dinner, a dinner led to a series of conversations and meetings and interviews. Before I knew it, I was hanging up my robe literally and signing up for a very different kind of life at the company.
H
Host41:33
Earlier you referenced this concept of seizing opportunities, like here it comes, you got to be prepared for it. I want to explore that theme in some of these other moves you've made. With your friends, how did they know to come to you with that? Had you told them, 'Hey, by the way, I'm open to other opportunities,' or was there something you messaged in that way? Because you said you were happy. Tell me how people need to talk to you about this.
P
Paul Grewal42:02
I 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. 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.' I can't say that immediately I thought, 'Oh my gosh, yes, this is the next thing I need to go do.' I tend to be much more circumspect or incremental. So I said, 'Yeah, I'll have a cup of coffee. Let me hear more about it.' It just sort of built upon that, as opposed to for some people there are grand revelations like Moses coming down from the mountain with tablets about what they want to do next. That's just not been my experience. It's been much more about seeing something that catches my eye, learning more, and then thinking through, and this is something I've weighed very heavily: is the upside of the new opportunity not just incrementally better than what I have right now, but does it possess the potential to be two, three, ten times better, however you define it and according to whatever metrics you use, in a way that makes it worth taking that leap of faith and risking that it doesn't work out? I think you have to think about whether there are those big leaps available, or at least potentially available, in a way that makes it worth pursuing.
H
Host44:10
And then with the move to Coinbase, how did that opportunity come about? How did those two converge?
P
Paul Grewal44:18
Coinbase was, again, I know a lot of people talk about how they were 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. 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. It was a smaller, more chaotic place. And yet, by 2020, it was clear to me that cryptocurrency and digital assets were not going away. They were not some fad or fraud that would just disappear as quickly as they appeared. This was for real. 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 in law that could benefit from someone who had spent a lot of time in the courtroom, but had at this point managed some very complex investigations for a major tech company, and critically, who had learned how to navigate the corporate world, how to marshal resources inside 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 power on occasion with no real explicit authority. Having learned a certain amount about how to do all those things inside Facebook, I think there was an opportunity for me to really apply those lessons in a pretty significant way at Coinbase, given that Coinbase at that point was less than 10 years old, a generation or two earlier in its development than Facebook was. It just made a lot of sense. As I went through a process of interviews and conversations and more lunches and more dinners, I came to really like the people at Coinbase, in much the same way that I really liked 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 co-workers that annoyed me or frustrated me. For the most part, the people I've worked with in each of my jobs are people that I still consider friends to this day. When I saw that same sort of spark and magic here at Coinbase that I experienced at Facebook, and added to that the instinct 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.' So once again, I took on a new job. I started as the new guy. I had to prove myself once again, and still have to prove myself even to this day in many ways.
H
Host47:51
And then how did you think about the risk profile of the role being very different from Facebook to Coinbase? Facebook was a de-risked at that point. It was just pretty much here to stay, and any legal issues it was facing were from the fact that it was here to stay. Coinbase is a very different scenario. Tell me about how you thought about those two risk profiles. Was it the case that because you had skillful management of your personal finances, you felt like you could take a flyer here? Was it because you had seen it all? You joined the work as a partner, got a variety of experiences as a magistrate judge, took on this role with a different set of properties at Facebook, and now you could enter a new phase. Of course, it could be both of those, but tell me what made the risk profile of this move attractive for you.
P
Paul Grewal48:46
In terms of my professional risk appetite, I've been very lucky that throughout my professional life, I've had the support of my wife, who has been quite successful in her own career, providing 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. Having seen that to some degree at Facebook, but more importantly, having 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. To be very clear, the number one risk I had to confront and work through was how to tell my parents I was going to work for a cryptocurrency firm. My mom and dad were certainly aware of what Bitcoin was and what ETH and other digital assets promised to do, but they were much more skeptical. At the same time, like a lot of great DC parents, they were absolutely in love with Facebook and WhatsApp and everything else. I was leaving a company that they literally engaged with several dozen times a day, every day, with the people closest to them, to go to this cryptocurrency company that sold Bitcoin. Thinking through that narrative was probably much more of a challenge for me, how I was going to make that phone call to mom and dad, than anything else I had to worry about.
H
Host50:31
Yeah, explaining things to your parents is definitely a big obstacle.
P
Paul Grewal50:37
It doesn't matter how senior or seasoned you get. That's always still the most important call to make.
H
Host50:45
I'm curious in your story so far, I haven't really heard you talk about the role of mentors and role models for decisions. I haven't heard you say, 'Well, I saw someone make a move like this and that seemed interesting,' or 'This move didn't work for this person, so I learned from a negative example.' In these different moves you've made, were there models that you looked to for a gut check, for guidance, for rules of thumb, or was it really just feeling this out on your own?
P
Paul Grewal51:22
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 at every stage of my career and 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 on the frozen steppes of northern Minnesota, probably wondering what the hell he had just decided to do when he came to the US for school. Eventually, my mom and my older brother showed up. When I think of 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. It's like, 'Oh, do I be a federal judge or go be a law partner, or do I go be a chief legal officer?' Hardly the challenge that the people closest to me have had to confront several times in their lives. But even within the law, the judges that I worked for, their joy in their work had a tremendous imprint and impact on me in ways that continue to this day. That's always been an important touchstone for me in thinking through new opportunities. I don't expect to be giddy and on cloud nine every day. In fact, most days, these jobs are super hard. They're stressful. They grind you down and in some cases they beat you up. But over the course of many of those days, and hopefully 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? Am I finding joy in what I'm able to accomplish? Assessing that potential has been an important framework and milestone for me as I thought about new career opportunities. Another thing that really helps is I've tried to never assume or presume 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 want to say that I'm a complete fatalist, but even when I was a much younger person, I've always had this nagging sense that there's a bus on a street corner waiting to run me over, or a change in circumstance that could mean that I don't get to do this anymore. I try not to take for granted that I have these opportunities. So if something catches my eye or intrigues me, I'm going to go do it, even if it means I'm going to stumble and bumble along the way.
H
Host54:25
It's totally fair that compared to your parents, the magnitude of the decision and the different outcomes pales in comparison to the privileged position of having these great opportunities. But in the position of having those opportunities, did you look to any other guideposts? Did you see other decisions, like for the move from Facebook to Coinbase, from an AGC role to a GC role? Were there people who had taken similar moves, similar asymmetric bets, that either paid off or didn't, that you looked to for a gut check?
P
Paul Grewal55:10
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. That was not all that hard to understand, and it was very easy for me to picture myself following that very tried and true path. What was much harder was identifying role models in terms of judges who had left the bench not 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 sit in a corner office and give advice, but as a working professional inside a corporation where you're subject to performance reviews and bonus assessments like everybody else. 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. Then leaving what 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 who necessarily did that in the way that I did. I really had to reason a lot of this out on my own, applying some pretty simple, maybe even too simple, standards: Am I excited by this? Is this something that I will look back on in three, five, ten, or twenty years and be proud of the work that I've done, regardless of how it turns out? The other thing for me has always been that the lawyers I've admired more than any other have typically been the ones who have engaged the law in a number of different ways over the course of their career. I've respected the heck out of the lawyer who goes to a fancy law school, joins a law firm as a summer associate, and 32 years later gets a gold watch. But that was never what I wanted to do. I always wanted to be one of those people who was able to climb different mountains and engage with the law, which I've always loved, but in different ways, and be successful to some degree in each of those circumstances. That was always what defined success for me, and that's been useful in sorting through different opportunities at different points in my career, because the fact that I'd been successful at something for five or ten years before didn't really weigh very much in my calculus.
H
Host58:08
You mentioned that you love the practice of law. Is it possible to have a rewarding legal career and not love law?
P
Paul Grewal58:19
I think you and I probably know between the two of us dozens, hundreds, thousands of people who, from the outside, 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. Law allows you to compartmentalize what it is you're there to do and avoid having to start each day figuring all that out. And yet, are they happy? Or even if they're happy enough, are they as happy as they could be? Was their work meaningful? Did they actually accomplish things that mattered? In some cases, the answer is yes, and those are the people that I tend to admire and enjoy being around the most. But in many cases among lawyers, the answer is either no, or just as concerning, '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.' I always wanted to be one of those lawyers who look back with no regrets. We've talked a lot about my successes, and I'm grateful that you have focused on a number of them, but I've stumbled and fallen in many different ways. You mentioned the judgeship that I had as a magistrate judge. What we didn't talk about is that I was at one point considered for a district judgeship and had my proposed nomination pulled at the very last minute. That was devastating to me. It was embarrassing to me. And yet I had to pull myself back up. We didn't talk about the fact that when I went to Facebook, about 18 months or two years after I joined, the general counsel left and I was considered to replace him, but I was not picked. I was passed over. That was embarrassing, frustrating, and challenging. More recently, I've won a few cases and we've done pretty well in some investigations here at Coinbase, but we've also lost others. 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 the way that they had hoped for and expected. I'm stumbling along the way as much as anyone. And yet, 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 had 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 that's the regret I try to optimize against to the degree it's within my control.
H
Host1:01:04
I think that is worth commenting on because I've definitely known a number of equity partners over the years who, talking about some entrepreneurial move that they've observed, maybe me, maybe someone else, and said, 'Oh, I thought about doing that at one point. I would like to do that, but they're just so tied to that identity of that one path they're on.'
P
Paul Grewal1:01:31
I honestly think it's much more that. For some people, it may just be that 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. They've been not just a lawyer, but a senior lawyer or a partner in this organization for a very long time. With that comes a certain status, a certain amount of deference, but most importantly, a certain amount of defined purpose. You know what you're there to do. 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 you're aiming for. That's the life of most entrepreneurs I know, or even people who pursue new opportunities where they have to learn that landscape all over again. I think it's that fear as much as anything that holds too many lawyers back. I'm not immune from 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 aspirational and impressive as the practice of law can be, it just barely scratches the surface in terms of all the other things that talented people can do in this world if they just set their mind to it.
H
Host1:03:02,
Tell me about risk-taking in your experience. My impression of you is that you are definitely on the risk-taking side of the spectrum. I'm curious, do you think that is something innate in someone's disposition, just the way that some people are inclined to be in the outdoors or drawn to the arts? Of course, it could be cultivated, but largely speaking, some people are just more driven in a certain way. Do you think that risk thing is a cultural issue that could be mitigated, or is it just inherent in people?
P
Paul Grewal1:03:46
What you're ultimately asking about is the classic nature versus nurture debate. I do think that there is a certain nature that defines or describes, certainly among lawyers, those that are more willing to take risks or more willing to adopt a new view of their professional life and set of professional opportunities. But I think there are important ways in which that instinct, or maybe even that talent, can be developed and nurtured. One of the things that amazes me is if you think about how we recruit and attract people to the practice of law. Look at the amazing range of experiences and interests that defines the entering class of every law school I'm aware of. We encourage and really prioritize a wide range of diverse interests in selecting members of any given entering law school class. Then what happens over the course of the next three years? We sort of chip away at, winnow, and beat down all the ways in which all these different people are special, and ultimately turn out a very similar profile of a finished law student product. From there, it only gets worse. Think about what an entering class of associates looks like at any major law firm: incredible range of interests, incredibly diverse talents. We sort of define what it means to be successful and accomplish in a way that standardizes that, and it looks very different when you finally get to the very small number of them who make partner or build successful practices inside the firm. I do think that resisting that wherever possible is important. Having a bit of perspective and understanding our history is also something you can nurture that will lead to a greater appetite for risk or a greater appreciation that the choices most of us in the practice will have to make are really extremely similar and don't vary very much in terms of risk or potential downside when you look at the grand arc of what most people in our society and our community have to deal with on a daily basis. Even if that's too abstract, I come back to our own families, our own stories, our own histories, where in almost every one of our family's stories, 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. Having an understanding of history and appreciation is also really important.
H
Host1:07:05
When you talk about risk, it seems to me that you've been taking risk with these career leaps. It's kind of this all-in risk 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 that is a way to stretch yourself, challenge yourself, not as risky, but exposes you to and gives you the benefit of exposure to new experiences and new perspectives?
P
Paul Grewal1:07:38
A thousand ideas come to mind. A small example: I think of risk and exposing yourself to new people, new ideas as maybe the most important element of developing a different approach to career choices. It can be something as basic as instead of flying to Maui like everybody else does for a week or 10 days when you're a hardworking law firm associate, and sitting on a beach relaxing in a way that you totally deserve and have earned, maybe spend that week or 10 days of vacation taking a pottery class at your local community college, where the people you're going to be interacting with are going to be very different from the people who tend to go to the same resort and the same island at the same time of the year. Maybe it's instead of moving up from a two-bedroom with your roommate to a three-bedroom, staying an extra year on that lease and then taking the amount of money you would have spent on the additional rent and dabbling in a little bit of real estate with 10 of your friends, starting with a one-bedroom condo purchase that needs a lot of work and building it up. There's just a thousand different examples like that. Maybe it's instead of billing 2,400 hours a year at your firm in order to qualify for the next level of bonus, only billing 2,200 hours a year and either taking on pro bono work that exposes you to different ideas and different kinds of clients and legal issues, or spending those extra 200 hours a year reading a book or a series of books, continuing to educate yourself in literature and art and music. That's another way to take different risks and expose yourself to different ideas. 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, we imagine or 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 there are all kinds of different alternatives out there. You just have to take the blinders off sometimes.
H
Host1:10:01
You talked about exposing yourself to people with different sets of ideas, and I'm struck that in the story you're telling of the magistrate judge, 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 and relationships, and what role has that set of relationships played in your career?
P
Paul Grewal1:10:27
I'm actually going to focus on the word 'friendship' because I think that's the most important type of relationship. It certainly has been for me, because it's the one that's often the most neglected. We all instinctively understand that inside our families, we have a responsibility to our partner, to our children, and to our parents. I think that's generally well understood, and some of us are better at that than others. But at least we all generally appreciate that it'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. 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. In my personal and professional life, I've tried to resist that. 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, but those tend to be my people. Throughout my career, one of the things I've been proudest of is that whether it was when I was a law clerk, a young associate, on the bench, or even to this day, 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 have remembered even when my own life gets very busy and I have competing demands on my time. To answer your question about how that's impacted my career, 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, in giving them a piece of advice or thinking of them when I get a phone call about an opportunity that's not necessarily a great fit for me but could be a great fit for them, with no expectations, just trying to help other people navigate this hard, crazy life as best as they can. On occasion, sometimes that does come back, and I've been grateful for when it has, but I don't have that expectation. I don't think any of us should have that expectation in any of our successful friendships, because it is much more valuable in the giving than in the receiving.
H
Host1:13:10
I understood your comment about the ways in which friendship is neglected. If there's family, which is well understood, and investing in professional relationships like being part of a bar association or client development, those are well discussed. You can take a course on family stuff, there's lots of support for that. There's lots of support for networking and professional stuff. But relatively little in the way of 'here's how to focus on your friends' and reminders on friends. It occupies this value between those two.
P
Paul Grewal1:14:03
Yes, and it's the hardest thing, especially for lawyers, because we have pretty demanding schedules and lives. Professionally and 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 lives, that you ultimately have a chunk of life professionally and personally where friendship is really all you have, whether you have a life partner or an extended family or not. It's interesting that when we're younger, 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. I don't think we make the necessary investments along the way that set ourselves up for success. I'm trying to resist that and avoid that, again with varying degrees of success, but it's something I think a lot about.
H
Host1:15:30
Going back to something you were talking about earlier, you were talking about difficult decisions that you've grappled with. I'm curious for you, what was a decision you made that you're not sure you got right?
Decision you made said, you know, I could have gone one way, I could have gone another. I went this way. But I'm not sure I made the right call.
P
Paul Grewal1:15:56
Yeah, I'll start with a professional example. I don't know for sure whether it was 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 was a unique satisfaction in seeing the tangible results of my labor day in and day out. I could see individual parties in my courtroom, and these weren't the big fancy tech companies that a lot of people associate with my time on the bench. These were just regular people in court for either the first time or the hundredth time. When I made a decision and it was the right decision, it was incredibly gratifying to see that look on their face. Would that satisfaction have only increased or grown had I stayed on the bench? I don't know. Would that have ultimately been more meaningful to me than whatever else I've been able to accomplish since I left the court at Facebook or here at Coinbase? I don't know. I think that will always be an open question, but I don't tend to dwell on it because in many ways those are unknowable questions. The answers are never going to be completely revealed. Fortunately, there are many other things I have been able to accomplish instead that would not have been possible had I stayed in that role. A personal example I think a lot about is that when I grew up in the Midwest in the 70s and 80s, in a very small town in Northeast Ohio, a place I'm very proud to be from, I felt compelled to go away for school. And 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. 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, as I've essentially been living this immigrant life in California for over 20 years. I've never really felt at home here. I think a lot about those choices as well. Yet, if you dwell on them too long, it's important to be reflective, but you ultimately end up right back where you started, having traveled in a big circle because there's no way to know the answer. It's much more productive and satisfying to think about what you've been able to accomplish that wouldn't have been possible had you not made that choice.
H
Host1:18:36
Well, it's funny because last time I saw you, we were at a conference and you were in workout gear. You're the chief legal officer of a tech company with a major regulatory component, on the bleeding edge of tech and financial issues. So it's very funny to hear you say you feel out of place in California. Tell me more about that.
P
Paul Grewal1:19:01
Well, I've been living in California for roughly 25 years. I've lived here longer than I've lived anywhere else. Yet, like a lot of immigrants feel, even though you may have spent decades in a place, if you're not of that place and from that place, you sometimes feel a bit like an interloper or a visitor or an outsider. That's as true for me here in Silicon Valley as anyone else. I appreciate that I present in a way that suggests I have overcome those obstacles, but 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, finding no greater joy than 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 when I look in the mirror every morning. It's not some guy trying to solve the world's cryptocurrency problems or fight the latest tech fight as a chief legal officer.
H
Host1:20:02
Well, you've met my wife a couple times, and she's got a question for you that I think is good. Look, you're in California at this crypto company. There's got to be something woo-woo about the guy. So what is the most woo-woo thing about you?
P
Paul Grewal1:20:21
I don't know. I hate to disappoint her. I'm a pretty dull guy in many ways. I suppose it's a little off base for me that I don't shy away from the darker corners of the internet. In my professional job, especially in cryptocurrency, I have to spend a lot of time on Twitter, Discord, and subreddits. As many of your listeners will know, those portals can take you to some very crazy, dark places, particularly in terms of conspiracy theories and 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.
H
Host1:21:29
What's one conspiracy theory you can't shake?
P
Paul Grewal1:21:34
Oh gosh. 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. I don't necessarily believe 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 extraterrestrial life exists? Absolutely. Would it surprise me to learn that if there was contact with that extraterrestrial life, one or more world governments would have been incentivized or inclined to try to cabin or limit our understanding or knowledge of it? No, I wouldn't be. So maybe that's something I'm a little woo-woo about.
H
Host1:22:28
Yeah, that is interesting because I fully buy into all the premises you just laid out. My only question is, what is there? Obviously, by definition, if a government is hiding something, you don't know what's being hidden from you. But over time, some things leak out. Things once secret are no longer secret. The Tuskegee experiment, these kinds of things were once secrets. But I feel like there's an equilibrium, like in physics or chemistry, where if there's such a strong density of something on one side and a vacuum on the other, it's going to find its way out. It's just too powerful a thing to keep hidden, too much incentive for any individual to break from that because there's such a huge payoff. So what is some precedent where we've seen that breakdown? Or if you haven't, how can you make sense of the unbelievable incentive and motivation to tell everyone, 'Here's the craziest thing: there are extraterrestrials'?
P
Paul Grewal1:23:48
Yeah, I would say a couple things. One is, I'm not necessarily saying this is probable, I am saying it's plausible and most definitely possible. The other thing is that when it comes to extraterrestrial life as one example, 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, as you highlighted with a couple of examples, human beings have kept some pretty dark things quiet for a very long time until they weren't. Without being too morbid, I think there are plenty of examples even in our recent history in the 20th century where things that seemed utterly implausible were kept secret for a fairly long period of time and then were revealed. All I am saying is that we shouldn't dismiss entirely the possibility that there are other beings out there and certain people on earth aren't necessarily incentivized to make that as publicly known as it should be. How's that for woo-woo?
H
Host1:25:08
That satisfies woo-woo. I think that's woo-woo. Well, you really love lawyering, so I don't want to miss out on that, but I want to pick up on that shortly. You mentioned social media, so we can start from there. Tell me, you're highly active on social media. You've got like 50,000 followers on Twitter, more than 25,000 on LinkedIn. I think you were active on social media before you joined Coinbase, but it certainly exploded as a result of that. So tell me, I think so many lawyers are very averse to being active on social media, particularly somebody who is at a company that faces such regulatory scrutiny might be even more averse to having a public face and making sure every minutia is adequately messaged and lawyered. Tell me about the decision to be so active on social media. What does it do for you? What do you get out of it?
P
Paul Grewal1:26:23
Well, my appetite and interest in social media goes back well before my time at Coinbase. I did work for a social media company of some repute for several years immediately before I came 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 posting a lot on Facebook itself and elsewhere. It was largely because I was curious and interested in how these new technologies could reach different audiences and allow you to have a different kind of voice than maybe was possible before. When I came to Coinbase, I was well aware that the cryptocurrency community tended to thrive on Twitter, Reddit, Discord channels, and elsewhere. So it was quite natural for me to look to those channels when trying to explain what we were doing at the company, how I thought about the law, and how the law applied to what was happening in crypto. It was a very obvious and natural place. At the same time, I've tried to share a bit about how I think about the practice of law and the profession in a way that goes beyond just my particular industry, because I do think there is an interesting conversation to be had among lawyers about how to navigate some of these challenges or deal with the day-to-day struggles of the job. By sharing how I've looked at things or lessons I've learned, certain people have found it useful or interesting in their own work or lives, and that's very gratifying. But mostly, it's not some grand plan. It's mostly about me wanting to spread the word about what we're doing at Coinbase, encourage other lawyers to think about their professional journeys in ways they haven't before, and maybe even just kill a little time while I'm brewing my coffee in the morning and there's nobody in my house to talk to because my children and wife have left for the day, and I need some other person or group of people to communicate with.
H
Host1:28:55
Why is it important to message? You have an outlet for changes you need the SEC to consider or a court to consider. Why is it important for the public or the crypto community to be bought in?
P
Paul Grewal1:29:13
Because these are ultimately public institutions. Whether it's the Securities and Exchange Commission, the Department of Justice, or any other part of our government, they are there to serve the public interest. That's my perhaps somewhat naive view of how government is supposed to work. Just as I think it's critical that people understand what their government is doing or not doing in their name, I think it's just as important that these institutions understand what the people they purport to serve think about these issues. For all of its flaws and risks and dangers, I think social media offers a very powerful and unique way to kickstart that conversation. I'm well aware of all the ways that conversation has taken off in unproductive and even harmful directions. But in my experience, day in and day out, I have a wonderful experience and incredibly valuable conversations when I engage on Twitter or post on LinkedIn. As a result of that, and the contributions of many more people that go far beyond just me, I think we have a much more informed conversation happening right now about the legal issues in crypto and about the legal profession. I think that's generally a good thing.
H
Host1:30:42
Has there been any surprise along the way? What's something you've been surprised to learn in the course of being active on social media and building such a large following, or the people you've met along the way?
P
Paul Grewal1:31:02
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 we are confronting right now in crypto, whether it's securities law issues or sanctions issues, so many good ideas come from people who I don't think in an offline conversation would be given the time of day by most other lawyers. There's an old trope on the internet that when you're on the internet, nobody knows you're a dog. There's a famous New Yorker cartoon to that effect. I love the fact that most of the people I pay the most attention to on Twitter, Reddit, and elsewhere are people whose backgrounds I don't even know. Frankly, I don't even care. I don't weigh very heavily what law school somebody went to when debating the right way to think about the meaning of an investment contract under the 1933 Securities Act. I just want a clever idea or a different way to think about the problem. In law, we are still bound to traditional ways of weighing and evaluating the worth of someone's contribution: where'd you go to school, who'd you clerk for, what firm have you worked at, is the company you work for a Fortune 100 company or one I've never heard of? Those are all signals that have some value in certain situations, but for the most part, they have nothing to do with whether the thing you're saying is smart. Do you have a good idea? Is your comment something I should be paying attention to? I love the fact that in an online space, the ideas tend to be at the center of how we value people's contributions. More often than not, I get really good ideas or a different way to think about a particular legal issue I'm wrestling with from individuals who I suspect wouldn't garner a lot of attention in traditional places and spaces in the law. I think that's awesome. It's a much fairer and more interesting way to operate and live. That, as much as anything, has surprised me about my experience talking about law and crypto on social media.
H
Host1:33:29
Are there groups of lawyers or niches of lawyers who should become more active on social media? You're in a unique position. There's a key benefit to messaging around these topics. They're at the bleeding edge, changing, relevant to a lot of people. You're the chief legal officer. But short of that unique set of circumstances, does it make sense for more people to be involved? Is there a profile of the kind of lawyer who should be more active?
P
Paul Grewal1:34:07
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 try to apply when I think about how I communicate with others, whether on social media or anywhere else, is: do I have something interesting actually to say? One of my pet peeves about lawyers on social, but also in communicating more generally, is that more often than not they skip past the 'do I have something interesting to say' question and focus on 'how do I say it?' I think that is where I would begin and urge others to begin. At the same time, I think sometimes as lawyers we presume that what we know or what we do is utterly uninteresting to anyone other than ourselves. The fact of the matter is, there's something interesting happening in just about every lawyer I know's life every day. The only question is how you can 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. That's the piece I think people sometimes miss. They either presume it's interesting to everyone, or they don't take a moment to think about how to present and frame it in a compelling way. The best way to do that is something we talked about earlier: when we were talking about the best trial lawyers and what makes them so effective in court, a key element of their toolkit is curation and deciding what not to say and what not to argue. I think that's just as true for social media. Less is generally more. A lot of 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 is compelling and interesting in whatever it is they do.
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Host1:36:04
I think the story of Coinbase and what it's looking to do is essential. It's been common among high-performing tech companies for founders to have a clear message. Paul Graham has underscored the storytelling component for a number of years. Coinbase and others are influenced by Paul Graham in that sphere. Tell me about lawyers, litigators are natural storytellers, but in the course of being at this cutting-edge company with a story to tell and flexing your muscles on social media, what have you learned about storytelling? What are the principles you've learned?
P
Paul Grewal1:37:02
Oh gosh. A couple things have become clear to me over time. This is true whether it's a LinkedIn post, a closing argument in a federal district court trial, or anything in between. I think the most important elements of a great story are the people, the characters. It's less about what they do or even how they do it, and much more about who they are and ultimately why they have made the choices they've made. This doesn't have to be some great piece of literature. This could literally be four lines in a tweet. Focusing on the people generally tends to make for a much better story than anything else. Another element of storytelling that's super important is to try not to accomplish too much. Again, focusing on the notion of curation. There doesn't have to be a grand unifying point or theory necessarily to a great story, but there does have to be a point. 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, a novel, or anything else you might compose. One other element of storytelling I try to focus on is: am I offering something new or fresh? Either compared to what I've said before or what others are saying. As humans, we are wired to the novel. We are always looking for the next thing. Rehashing or repeating points or narratives that have been made over and over again tends to take a pretty good story and turn it into a not-so-interesting story pretty quick.
H
Host1:39:00
I want to go back to something you said about not looking to tell people what to do. I fully appreciate that. But I'm curious for you. There are so many recurring scenarios that lawyers find themselves in. So much of legal training and the practice of law is about conforming and standardizing, which creates averaging effects. That makes it all the more challenging for people at key junctures of their career to make decisions. You know the canonical key junctures: the mid-level associate who doesn't know if they want to keep practicing, make partner, go in-house, or do something completely different. I'm sure you run into people like this all the time. What do you say to someone to help them sort through that canonical issue?
P
Paul Grewal1:40:20
Well, there's all kinds of advice out there on this topic. Applying my own standard that I just articulated, maybe I'll focus on a slightly different take I have. The number one thing I ask someone who comes up to me with that kind of question is: forget about what you want. Forget about what you enjoy. What are you really good at? If I ask 10 of your friends or five of your professional colleagues, what's the number one thing they think of when they think of you in terms of what you really excel at? What are they going to tell me? What are they going to tell you? I start with that because, in the way I've thought about my professional career, I have found that being really, really good at something in the practice of law tends to be pretty satisfying, even if it's not necessarily something I particularly enjoy or aspired to. It's not the be-all and end-all to the very important and hard questions that I do get asked and that people confront in their own careers over and over again. But being candid and honest about what you're good at is something a lot of lawyers overlook. A lot of us imagine ourselves to be very good at certain things we're not actually very good at, and completely overlook or ignore areas where we are extremely talented and accomplished, but are so second nature to us that we don't really focus on them. That's maybe a different way I look at that question than some other people.
H
Host1:41:53
I really like that. So now I'm going to apply it to you. Two audiences. You said you like associating with lawyers and you've got plenty of contact with them. What do you think the lawyers in your life would say for you? What is it that Paul Grewal is particularly good at?
P
Paul Grewal1:42:14
I think I am quite good at managing chaos and dealing with emotional overload in moments of crisis. I think that was true when I was in a courtroom and a defendant had an outburst, or a witness broke down on the witness stand, or a juror would lie to my face about why they couldn't serve and it turned out that wasn't true. I think that was true in my law firm life when junior or mid-level associates would suddenly break down, not show up for work, or walk out in the middle of trial. All 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. My first instinct is to pause, figure out what needs to be done as we talked about earlier, focus on the here and now, and deal with the emotional aftermath only after we've resolved the situation. Those experiences, that talent, is probably what I'm best at relative to my peers, as much as my ability to write, speak, or think about legal issues.
H
Host1:43:51
Okay, that's good. That definitely ties into running themes you've been talking about. Stepping into the master judge role, managing emotions was a key part. That makes a lot of sense. Now I'll switch. You report to a board of directors. These are people like Marc Andreessen, Fred Wilson, Toby Lutke. Successful software entrepreneurs and VCs. What would that audience say is your alpha, your expertise?
P
Paul Grewal1:44:32
I would hope that audience would say that I am uniquely able to identify paths forward and avoid being sucked into the classic lawyer's posture of 'we can't do this, we shouldn't do that, there's no way around X, we're never going to get past Y.' I think I'm able to identify paths forward that may not have been immediately or readily apparent to others. I think my board would call that as much as anything else that I do. I hope they would.
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Host1:45:12
Looking at that board, what have you learned from them? How do they approach decisions differently than skillful lawyers or jurists? What can we learn from that group? Fewer of us as lawyers have contact with people in those roles, and they've had a lot of success in different domains that require different kinds of decision criteria. What can we learn as lawyers from that group? What have you learned?
P
Paul Grewal1:45:39
The self-made founder tech billionaire is definitely a species I have much more familiarity with than I ever would have guessed when I graduated from law school in 1996. That's certainly been the case at Coinbase. You've mentioned several of our board members. Our CEO, Brian Armstrong, who also serves on the board, fits that bill. Mark Zuckerberg, in my previous role, also qualifies. One thing I've learned from working with all of these people, and they're very different from one another, not uniform by any stretch, but they do share certain qualities. 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 extraordinary. They are certainly all fearless. These are all people with lots to lose on any given day, yet they are very comfortable taking outsized risks when they are convinced they are right. The last thing I will say is 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 those impacted by what they do. That just hasn't been my experience. Over and over again, I have been impressed that the people I've worked with who fit that bill really do care deeply about the wider world and what kind of world they're going to leave behind. I can appreciate there may be some skepticism around that. These are not saints by any stretch. They're just as human as the rest of us. But there is a genuine not just interest but commitment to figuring out a way to do interesting things in this life and leave the world a better place. I don't think that always gets understood when we look at these captains of industry making grand decisions that impact billions of people. So that's something I've seen.
H
Host1:48:00
I'm trying to trace, with all the things you've learned, what makes Paul make a move? What is Paul looking to level up on? You're already in the chief legal officer role at a company that's had a lot of success financially. That dimension seems sound. You're working on cutting-edge legal issues. It would be hard to imagine something more at the forefront of public disputes with a regulatory body, trying to be on the side of what you think is right. It would be hard to top that. What company could give you more challenging legal objectives or compensate you more significantly? So it's got to be something else. Maybe flexibility. Maybe you've worked as hard as you can. I suspect that's not true. You're a very spry 51-year-old.
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Paul Grewal1:49:19
52 as of a day before yesterday, just to be clear.
H
Host1:49:23
Not enough. Okay. So it can't be that. I wonder if the answer is something along the lines of impact. That seems like the thing closest to regret, if you want to put it that way. 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. I've observed that there are certain GCs, chief legal officers, or law firm partners who have had a lot of success and then taken on non-legal roles. Jason Kwon of OpenAI moved into the chief strategy officer role. Gordon Moody moved into the chief product officer role at a legal AI startup. Brad Smith at Microsoft, former GC, is now president. There are many examples. I'm curious, what would it take for you to make that attractive, or what do you think makes it attractive? Is it a path more lawyers should consider?
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Paul Grewal1:50:48
Yeah, I think lawyers should definitely consider it. 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 corporate life altogether. For me, that might be something in my future. I don't know. I think that less important than the title or the organization is the problem set and the collection of challenges I would have an opportunity to engage with. One of the things I am really proud of as a member of the legal profession, and I think a lot of lawyers are really excellent at, is dealing with uncertainty. Orienting to problems where there is no obvious answer, being able to reason from first principles. These are tremendously valuable skills that lawyers develop each and every day, no matter what kind of practice you have, and they could serve them very well in other roles that go well beyond the law. I do think that to be successful in that type of different opportunity, any lawyer would have to be willing to shed their own skin a little bit, express and genuinely embrace a certain degree of humility that there are lots of things out there we don't know, and get excited by the fact that you're doing something very different from what you've done before, as opposed to being intimidated or turned off by it. If you have that mix of perspectives and attitudes, as a lawyer, you could do very well in any of those other roles. And we haven't even talked about all the things outside of corporate life where I think lawyers bring a lot of unique experiences and attributes that could lead to some amazing success.
H
Host1:53:06
It would 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 your career. That's a great place to stop right there.
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Paul Grewal1:53:17
Awesome.
H
Host1:53:19
Well, Paul, thanks for taking the time. Happy belated birthday.
P
Paul Grewal1:53:22
Thank you. I appreciate it. This was a fun conversation. I appreciate you having me on. I've enjoyed it.