Recharge with Legendary VC Bill Gurley and David Ko, CEO of Calm

Hey, everyone, and welcome to Recharge, the podcast. I'm David Ko. Today, my guest is one of Silicon Valley's most legendary investors. He's a venture capitalist who's backed some of the most transformative companies of our time, from Uber to Zillow to Grubhub. But he's not here to talk about tech deals or billion-dollar exits. He's here to talk about something much more fundamental: how to build a career you actually love, one that energizes you instead of draining you. And his new book, Running Down a Dream, is his roadmap for avoiding that trap. So let's recharge with Bill Gurley. Welcome, Bill. Hey, Bill. Thank you for joining us.

Thanks for having me. I really appreciate it.

Well, I'm so appreciative for you being here today. I know you are deep in book mode right now with your newly released book, Running Down a Dream. And I got to tell you, I so appreciated reading it. I could not put this down. And I am really looking forward to our conversation today to talk more about this incredible book. Awesome. There's a question I love to ask all my guests. And it's really the premise of this whole podcast and my own book here, Recharge, where we just take this topic around mental health and we try to equate it to a phone battery to make it a lot more approachable. And so I wanted to ask you, how is your battery and why? Yeah.

It's pretty good. It might be a little stressed from book launch mode. When I made the commitment and decision to write a book, I think I thought the minute the pen went down and when there was no more editing that the job was done. But that's not the case. There's a whole bunch of other stuff you got to go do, including the audiobook. Did you do your own audiobook? We did.

We did an audio piece. I didn't use my voice. I don't know if you did.

Yeah, I did my own. It's not easy. But I feel pretty good. I'm excited about the book and what it might mean for the world.

Well, I'm excited to get into all of this with you. And it really all started around 2018 or earlier when you were at your alma mater, the University of Texas McCombs Business School. And you really studied a lot of journeys of successful people, luminaries in different fields. And you say you noticed this pattern. Can you just talk to us a little bit about what that is?

Yeah. So just to give listeners some context, you know, during my entire venture capital career, I wrote a lot and I did a lot of analysis and I wrote a lot of blog posts. And I would analyze mechanisms, you know, and try and break down frameworks, you know, for what was going on in the world. And I think I built a little bit of a mental framework for that. And I had all these notes for blog posts unwritten and that kind of thing. And I was finishing a biography and in my brain I was comparing it to a few other biographies I'd read. And there was a through line. And interestingly, the three biographies that kicked this whole thing off, one was a folk singer, one was a restaurateur, and one was a basketball coach.

And what I love—I really love one element of kind of unlocking themes to success against those particular careers because they're the kind of careers your parents would tell you to stay away from. You know, they're not your prototypical computer scientist or McKinsey consultant kind of thing. They're off the beaten path. But in each case, you know, there was a story of an individual that started with intent from the very beginning, so the first rung of the ladder, and found a way to the top of the ladder. And I just noticed several patterns that were similar. The first one is just being a voracious learner in your field. And the reason this one took on such meaning to me is that I realized it was also a test for whether you were tilting against something that you have true passion and curiosity for.

Because if being the most learned person in your field seems tedious, then you're probably not in the right field. Like, you're not leaning against that thing that... really drives you, you know? And I use the phrase, you know, what would you do instead of watching the next episode of Breaking Bad? Is there something you're so interested in that it competes in your free time, you know, for things that you would consider to be entertainment? And I think we all know, I mean, we all know stories of people that just couldn't stop fidgeting with something that have gone on and turned it into greatness. But it comes at a time, you know, David, we did a survey with Wharton where we asked people, "If you could go back and start your career over again, would you choose a different field?"

And six out of ten said yes. Wow. And I think everyone knows, I think it's extremely well-intentioned, but we've been pushing kids through a bit of a conveyor belt or meat grinder towards college. And a lot of people are just starting to ask, do we really allow the type of roaming and exploration that gives the child time to figure out what they really would love to do?

I started this podcast and I wrote the book, I really wanted to normalize this conversation around mental health in the workplace. It's probably the most approachable it's ever been out in the wild, but when we get to work, it's not as approachable. And that was really part of the crux of the conversation. What inspired you at this time to put pen to paper? Because you've got so much you could have written about. So why now? Why write this book now for you?

Well, I had two early careers, and I pivoted and found my dream job, and I spent 25 years in venture capital. And it's funny, when I went out to pitch this book to publishers, the vast majority of them wanted me to write an investing book or a venture capital book or a tech book. They didn't want me. Absolutely. They didn't.

Absolutely. Why wouldn't they? Yeah. Makes complete sense.

But I was more motivated by this. I don't want to sound cliché-ish, but the sixth principle in my book is always give back. And I feel like this book has an opportunity to have a much bigger impact than any of those books could have had. I'm not sure we need more well-educated venture capitalists in the world.

Like, I'm not sure it's going to solve many problems.

But I'm hopeful. I'm very hopeful that this book can help unlock human potential. I hope that there's a whole bunch of latent potential that's kind of sitting on the sidelines because people don't have the conviction to just jump out and get started, especially in fields where, you know, once again, where a well-intentioned parent's not likely to encourage you to go. Yeah. And I think if people step into those fields with the right enthusiasm, they're going to be way more satisfied in their career and they're going to have far more impact, not just on their own lives, but on other people's lives as well. So well said.

You know, I want to talk a little bit about your personal experience, because there's a lot that obviously is written about yourself and we can, we can obviously read about that online. But what I really enjoyed about this book was the fact that you were just really so candid about your own journey. We got to see a real different side of you. And I got to see a different side of you. I feel like I know enough about you on the business side, but I really learned a lot about you on the personal side. You talk about... You know, kind of after college, you landed a job in tech and, you know, something that really should have been your dream job, right? As you talk a little bit about the resume building and everything else.

But you found yourself in your dream job, surprisingly bored. And you call that essentially what you call, like, the career regret trap. And, you know, what I'd love to just unpack and learn a little bit more from you is how did you recognize that? And then what shifted for you?

Yeah, I got an engineering degree. I loved engineering. I was working on these products at Compaq. But by the time I got to the third product, there wasn't much different than the second one. And I found I was in my free time... I was reading about investing. I had read Peter Lynch's book, One Up on Wall Street. I had opened a Prodigy account. I was trading stocks. And so this is a test. Like I said, if, in your free time, you're doing something different now than than your daytime, like maybe maybe that's a calling to push you in a different direction. And so, yeah, I just quickly took a leap. You know, I used MBA school. I think it's a wonderful pivot tool if you have the opportunity and the resources to do it.

And so I used that and ended up spending... From there, I went to Wall Street. I spent three years on Wall Street, had a great time, very successful. But the same thing, at some point I woke up and I asked myself a single question. And I think anyone could do this, which is, do I want to do this for the rest of my life? And if the answer is not yes, I think you need to start creating opportunities and optionality to go try something else. And you may go through three or four of these. We have a chapter in the book called Never Too Late about people that started their dream jobs after 40. One thing I would caution young people about, and I saw a lot of this in New York, if you build your lifestyle...

to the full use of the money you're earning, you can get stuck. Taking on a mortgage too early, like getting a second home too early, you might get stuck to where you can't pivot. So I would be careful. I would just caution young people to be conservative about spending so they have the maximum flexibility for career navigation and exploration.

Again, great words of advice there. I want to shift a little bit because you've mentioned this now in terms of your six principles. And I really enjoyed how thoughtful and how you laid them out, starting from chasing your curiosity to, at the end, always giving back. As you look at your six principles, and they really became almost like a structured roadmap for you, can you give us an example—and I think you already have a little bit—but of how one of these principles really played out in your own career? Do you hear that over and over again of any one of these principles? Has there been one principle you've gone back to more than the others, or they've been all equal to you throughout your career?

I think the one that I feel most strongly about and that I think is most unique relative to the others that I talk about is about peer relationships. I think that most humans don't take advantage of peer relationships as much as they can. And I think they worry about giving away trade secrets or personal advantages of some kind. And they worry about competition with these individuals. And I just think it's the wrong approach. I think it's not a zero-sum world. Rising tides lift all boats. And the more people that you can connect with that are on your same journey... You start to co-learn, you start to share networks, you share connections, and everything kind of gets exponentially easier. But it's not a natural human tendency.

I talked to—as a venture capitalist, I talked to a few founder CEOs and tried to encourage them to have each of their direct reports find four peers externally and meet with them once a year and come back.

I love that.

And it's not natural. I know from asking people to go do it, they feel awkward about it. Yet we uncover many stories. I had this in my own life, but some of them are just amazing. If you read the chapter about the athletic directors, there were like eight of them that all met when they were at the very beginning of their career, and they're all now at the top of D1 schools and are considered a threat because of their relationship. And they all rose together, and it's just a fascinating story. And so anyway, that's the one that just speaks to me the most because I think it's the one that's not leveraged enough. You know, you probably have—I assume you have—peer CEOs that you talk to all the time.

Absolutely. And we talk about this a lot as well, how we at one point were all together in a company like Yahoo, for example, or Zynga, which I was in. And a number of us then kind of split into different industries. I think the part that has held us together is the fact that we've held a lot of diversity of thought along the way and we've helped each other. One thing I've been very grateful for. So I really appreciate, appreciate that point because a lot of times people will talk about mentors, which you mentioned as well, and others. But I totally agree. That peer part is difficult sometimes because you feel like you're going to give away too much. And can you be as open and as honest with other individuals?

And one of the advantages of a strong peer group is that you can be more honest and vulnerable than you might be with a mentor. Like, you're going to be worried with a mentor that you're kind of exposing weakness or letting them down. And the peer group can also be there, like, when you're having a bad day. And great peer groups do this extremely well, and they have your back. They recognize what you're going through, and they get behind you.

Yeah, I often find, too, in a lot of my peer networks, that is, that many of us have the same types of struggles. Once we start to open up, once you find that trust and that bond where you don't feel it can be used against you in some manner, you're much more open and you realize we're kind of all in that same boat. We're having the same struggles sometimes with, you know, how do we manage employees in this world? How do we just do certain types of business? Oh, man.

Yeah.

Then it goes to, like, how are we handling our own mental health and how are we managing kids, families, you know? So it becomes—it really becomes—important for one's success.

I believe that. I totally believe that. You know, another one that's fun that I think is also not leveraged very much at all is I think there's huge value in studying the history of whatever industry you're diving into. And I think in addition to the fact—well, one, it's a good test whether you love it or not, because if it's boring to go do that, once again, you might be in the wrong place. Two, it's extremely differentiating to you as a candidate when you go out and interview. If you imagine 20 people interviewing for some, I don't know, a marketing job, and one of them can espouse the three original, you know, great marketers of all time and why they're great, it makes you look like you really care about the category that you're coming from.

Well, I mean, speaking of, like, in a way, about networks and examples and everything else throughout the book, you share all these real-life stories, just like you are right now. You're sharing it about individuals you meet and others. And you interviewed athletes, gaming, hairstyling. I mean, it was very, very broad. How did you pick and choose which stories would actually make the book? Because I just have to imagine that had to be one of the hardest things for you to go do, was to pick which stories.

Yeah, and it was part of why it took so long. I probably read 100 biographies. There were two things I was looking for. One, I wanted in each story to start with intent and to start on the bottom rung. So that part was hard. We wanted to find, you know, examples where people started on the bottom rung and had an intent to go do this new thing, because I felt like that was essential for the reader to believe they could go do the same thing. Right. And then I had favoritism towards careers that are atypical. So I didn't write about somebody that became the most successful Wall Street hedge fund manager of all time. There's nothing like that, because I fear we've been pushing too many people towards the same jobs and opportunities and not allowing people to go anywhere.

With unbridled enthusiasm, go chase what they love. And there's another element. In almost every one of those cases, these people ended up doing very well financially, even though none of them entered it for that reason. And so if you do something you love, you rise to the top of your field, I think you're going to be just fine from a financial standpoint.

That's good to hear. And actually, I want to go back to something that you spoke about right in the beginning of the interview. And that was a stat you shared from Adam Grant, where, you know, six out of 10 people experience career regret. If I just go back to that for a second. And, you know, in that one stat, sometimes there is a cost. There's a cost. Sometimes you go into a job and you're not really there. You're not present. And there's a mental health cost, not only to yourself, but to that employer where you're spending time, your coworkers, for example, who may worry about you as well. In your opinion, what is that cost of being on that wrong career path?

I mean, it's everything you said. The Gallup data is like staggering. It's like 23 percent of people are thriving or engaged. Fifty nine percent are quietly quitting and 18 percent are loudly quitting. They're like being intentionally disruptive in the workplace. And that's that's not a good sign. Like I just you know, and it's it's not healthy. And so I do think getting people in the right place. I use a phrase life is a use it or lose it proposition. Like, if you recognize you're in the wrong place, I would start finding a way to move. Like, it's okay, you know?

That actually flows really well into this next question just around, again, as we talk about where work doesn't feel like work, where that hustle doesn't feel like you're hustling, where work can really energize you rather than deplete you on a daily basis. If you're keeping kind of score, how do you know or what advice do you give to people when they've actually found it? They may not even know it. They may not know they're in the moment where they've actually found it. Or what are some of those signs that you would say?

I think there's one clear one, and I mentioned already, but like the fact that you spend your spare time learning about the job. And so many people enter their career and I think assume the learning's done. So, "I did that at college. I'm just going to show up and do the work now." And there are a few occupations—medical is one—where they kind of require continuous learning. But I've always found the best—and just imagine some of the founders you know—they don't stop learning. How could you even go implement AI at your company? This didn't exist when you were in college. That's right. You have to go study it.

And speaking of, of basically like what you just mentioned, there's a notion of mentorship there as well. And so let me ask you, it's really hard to get to a place alone, especially if you are a CEO or different fields. There's always people there that are helping you along the way. Why do you believe mentorship is so critical? And the second question is, who mentored you?

Yeah, okay. Well, let me start by just—I think there are two types of mentors you can have. One I call aspirational mentors. So sometimes we have this weight of mentorship and this anxiety about, 'Oh, how do I get so-and-so to take a meeting and have a coffee?' And I think they can be virtual. And then for the ones that are more local, I think you just don't start on the top peg. Like start with someone who's a little bit above you. And that person's not getting that call. If you study them and are respectful to them, they're going to be blown away that you recognized who they are. And you're going to have a much higher success rate than you could possibly imagine.

I just want to double-click on something you said there. So often, and I do this as well, we talk about mentors as being folks who are like CEOs and others. So really high-level people—just brought up such an important point, and a flood of names just started coming in—is the people right above you. When I had started Yahoo, I was in product, I was on the bottom. And I sought out people not at the top, but literally, just like you said, there were actually, some of them were peers and some of them were like one rung right above me. That actually kind of started the motion of how to find someone to seek advice. And I—and I totally agree because if I shot really high right there, I think people would have been like, 'Yeah, maybe I'll meet you once, but I won't meet you again.'

These people continuously met me throughout the year, which I actually thank you for. Thank you for reminding all of us that our mentors can be right above us or they could be peers of ours as well.

Yeah. And you asked about my own case. I think probably the most fortunate thing that happened to me was getting invited into Benchmark because it had this very unique—the venture capital firm where I work had this very unique equal partnership policy, and they would, we always have, invite someone that's in their late 20s to the table and able to have an equal voice. But the founders of Benchmark that I worked with had a good five or 10 years more experience than I did. So I had this really unique situation where they were rooting for my success because they were going to share equally in anything that I achieved. But I had four amazing mentors, you know, right next to me every single day, which was like an unfair cheat code almost.

Well, I wish I had one of those, too. So as you've talked about continuous learning and we've been talking about this off and on throughout this conversation, one thing actually I don't think a lot of people recognize is how much you advise people to read as many books as possible.

Maybe in this era of all these different things you could go do, why books?

It was books for me. I don't know that it has to be books. You could question why I believe it or whatever, or you could recognize that almost all—you know, Warren Buffett's just a constant reader. You know, there's so many people. And you start to borrow things from farther away, too. Like, the big innovations that you might make might come, you know, from someone in an entirely different field, you know. And—and it just requires kind of infinite curiosity is what I would say.

Love that. Love that. Totally agree. Listen, here at Calm, we talk a lot about sleep. I talk about this as well and how my relationship has changed with sleep over the years. Yeah. You know, how is your relationship with sleep, and how has that changed over the years as well?

It's something I think a lot about and I value quite a bit. The things that have been effective for me that are borrowed from some of the better writing and books—like complete pitch-black darkness, 68 degrees or lower, which not everyone does—but those things and relative quiet, you know, if possible.

Before we wrap here, and we could just keep going on here forever, I like to end our episodes with three final questions. I don't call them a speed round because I like to take my time here, but they're pretty quick. So the first thing is, what's something about you that might surprise people?

They might have seen this in a podcast, but they might not know what a big music fan I am. I probably see 40 or 50 live shows a year.

What? Wow.

Yeah, a lot. And yeah, it's just a passion of mine. And it's probably the fact that I can't do it that makes me appreciate it.

Is there a favorite artist you go to time and time again here?

Well, I'm a big fan of a very narrow genre of music called alternative country, which most people may not know. But there's a few bands that are breaking out in that category right now. Red Clay Strays is probably one worth mentioning. And there's an album out of Ireland this summer by Amble called Reverie that is phenomenal. I can't stop listening to it. So there you go.

There's a few people behind me you can't see right now who are like literally going, yes. And so I didn't know that myself actually of some of these individuals, but that's great. So you inspire so many people. Who inspires you?

You know, it's funny. I'd say almost every one of these stories that I had the opportunity to write about. And for many of them, we had an opportunity to sit down with the individual. And I'll give you just a great example. In the Jen Atkin chapter, this hairstylist, she would fly to Paris during Fashion Week and sneak in the back door and just stand in line and volunteer to style people. And the audaciousness of that, I just can't imagine. It's like Dylan hitchhiking to go meet Woody Guthrie. I just, I can't imagine a human having the wherewithal to, like, one, to do it, to pull it off, like, and she was doing it for free to build reps and build her network and to make connections. And I, like, when I hear stories like that, I literally get goosebumps.

Like, they really do. Um, they really do touch me. And so, um, part of the discovery of writing this and finding these anecdotes has been very rewarding, like, because I just, I love, I love those kind of moments so much.

That's amazing, Bill. And finally, what is your favorite way to recharge?

I really like road biking. It was a lot easier in the Bay Area. I find it's just such an intense workout from a cardio perspective and I can get lost in thought. I even, like, oddly found myself solving problems while I'm out riding and not feeling exhausted by it. But, like, you disconnect, you ruminate on one thing while you're going and, and maybe come up with something. So it's always been my go-to. I just adore it. It's harder here. That's harder here.

I've heard that about you. I've heard you've packed your bike and gone with it where you've traveled. I have done that.

Because that's just part of your core routine, right? Yeah, yeah.

Amazing. Amazing. I want to say again, thank you so much again for your time. For all of our listeners out there, please, please do us the solid of going out and getting Bill Gurley's new book here, Running Down a Dream. It's available today, wherever books are sold. And lastly, for our viewers and subscribers, please, if you haven't already, subscribe to our channel so you can catch all these great episodes of Recharge. Thank you all again for listening, and we'll see you next time.

Thank you.