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

Great to see you. Thanks for joining.

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.

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.

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.

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.

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.

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.

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.

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.

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.

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.

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.

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.

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.

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.

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.

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.

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.

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.

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.

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.

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.

It doesn't matter how senior or seasoned you get. That's always still the most important call to make.

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.