Bill Gurley on Career Regret, Finding Your Passion, and Why Most People Stay Stuck Too Long

What's up, man? How you doing? I'm doing great, Josh. How are you? Good. Um, I know we're supposed to do this live and we got the, uh, blizzard bonanza apocalypse of '26, but, uh, I think I'm going to see you. I think it's going to be okay. The sun's coming out. I agree. You're, you're actually a natural optimist. I'm generally more of like a cynic or skeptic, and I admire your, uh, I, I, I think—

If you ask around Silicon Valley, they'd put me in the cynic camp, but, but maybe I get a little bit of both.

I actually think you, you have more faith in people than I do. I think you—ah, okay.

I am cynical of the, uh, of the mass freak out of the potential blizzard apocalypse. And I think I was right. You were.

Let's start at the beginning. I first got to know you from a distance when I was literally obsessively reading your column, which was Above the Crowd, apropos, because I do think not only you're a towering individual, but a towering intellect who I feel grateful to call a friend, and I've learned so much from you. You've given me a lot of advice that I've not always followed about not being tight with people and thinking about the heroes that certain entrepreneurs and founders celebrate. But, um, you've, you've really surrounded yourself with just incredible operators, incredible peers, and, and capital allocators. Um, your career started, and, and you said that you sort of landed a job, I think, at a famous tech company after school, and you were surprisingly bored, I think was the quote you used. And what was that moment of realization like, and, and how close did you come to just staying on that conveyor belt?

i don't think i don't think there was much probability of that and i what i would tell you is um so i fell in love with computers at a young age like many people in our industry did um i had a commodore vic 20 that's how old i am television mine was a commodore ford asterisk comma eight comma one but i'm with you and um and i went and got a computer science degree and i was i was blown away like writing software in college was so much fun the fact that you could make stuff that actually would go do things was like i thought magic and i just got out and was in the world and working on product cycles and we started our third product which looked like the second and looked like the first and i want to add

Now, in the meantime, I had started reading industry trade magazines. I had read One Up on Wall Street by, um, Peter Lynch, and I had opened a trading account on, you know, Prodigy, and I was trading stocks, and I'd gotten a Value Line thing. Oh, as a hobby. Like, I wasn't doing that as my main gig, but, I, one of the things I talk about in the book is maybe your hobby should be your main gig, you know? And so I had these other things going on in my brain that seemed more interesting than what I was doing. And I don't—I think it's really important to highlight that engineering may be someone else's passion. It just came to a realization it wasn't mine. And I did this exercise, which I only reflected on as I wrote the book.

I don't know that I said, "Aha, I'm doing this exercise," kind of like Bezos did when he started. But I said to myself, "Do I see myself doing this 30 years from now?" And you can look around the org and see the people that have been in that type of job that long and look at their life and just say, "Is that something I would enjoy?" And what Bezos did was he said, "What advice would my 80-year-old self give me?" But I think they're going at the same thing. Like, is this what you want for your whole life? And for me, I didn't know it was venture at that moment. I knew it wasn't what I was doing. Um, so I went to business school, which is an easy place to repot from. Um, I got—I thought about venture while I was there. I liked the fact that I'd learned about stock options at Compaq. That was intriguing to me. Um...

I knocked on doors, and it didn't seem like there was any reasonable path to venture as a business school student. I started reading a lot of Fortune and Forbes and the Journal, and these gentlemen at Goldman Sachs, their tech team back at the time was incredible. They're sell-side analysts. And they were being asked the questions about these industries I was most fascinated by. I loved my corporate strategy class. And so I was like, maybe I could be one of those guys. And I went and knocked on doors up here in New York City and, and, and met the Goldman team. Even though I was a silly, you know, first-year student at University of Texas, they let me in the door, and I eventually got a job as a sell-side analyst, and that's where I became even more aware of what was going on in Silicon Valley, the young companies that were disrupting things. I realized

Like if I had a chance to follow a new company that had just IPO versus say DEC or HP, like I was drawn towards what was on the edge and eventually made my way to Silicon Valley. I had that same discussion with myself as a sell side analyst about two, three years in. I walked around the office late one night, about 10 PM, Park Avenue Plaza and the 36th floor and the corner offices were the most senior offices. sell-side analyst. So I could, I paused in front of each of their office. They were lifers in the role and it gave me the ability to say, is that what I want? And again, I got to a note pretty quick and started moving in a different direction.

You, you mentioned Compaq, and when I was starting Lux, you know, I went around to older venture guys and tried to learn some lessons, and, you know, they didn't feel threatened, and maybe they thought I was naive and ambitious, but I met Ben Rosen. Sure. And I remember he, he gave me advice, uh, of, of Sevin Rosen, for folks, for folks that don't know. And, and, uh, and his advice was, was very simple. It was, like, few words: 'You just need one.' The whole take was, like, Compaq for him was a success when he was able to parlay.

And by the way, I ended up following Compaq on Wall Street, ended up getting to know Ben really well, who was chairman, who was active—like, talk about active as a chairman—and even spoke at the Sevin Rosen LP meeting before I ever became a venture capitalist. So those experiences helped pave the way for where I would spend a quarter century.

Well, I want to start with, like, the genesis of the book. I want to go into a few of the principles, which I think are going to be timeless ones that people are going to absolutely love. And then I want to go into some contrarian takes, some real talk. The book itself was sort of, you know, this decade-long project. You said it started in part when you noticed that there was this pattern across three different biographies. You had a restaurateur, you had a basketball coach, you had a folk singer, and you connected these threads. And I know you've always liked this idea of, like, far analogies. And I think that was a Stanford guy, and these analogies in their lives between these things. And what was that thread that you pulled that connected those three?

So one thing I would say is, you know, as a blogger my entire venture career, and one of the things that you do with a blog post is you're trying to tear apart some new thing that's happening in venture and create a framework for understanding it. And so when I finished that third biography, I had this aha where I was like, 'Look, these people are all in very different fields. They're all in fields your parents would probably tell you not to go into. They all started on the very bottom rung, and they all did a lot of similar things. Like, they used a lot of similar processes and, and principles that could be borrowed by anyone, but not necessarily that everybody does.' And that's when it kind of hit me, and just as this would hit me on a blog post, I'd jot down some notes and then leave it alone for a while and come back to it. And in this case, that's...

It was sitting there, and then I got asked to speak at my MBA school, and I asked, "Can I do this presentation?" They posted it on the internet. Some people noticed. One of those people that reposted it was James Clear—I don't know how he found it—who's probably the most successful writer in the category by far with Atomic Habits. Eventually, a couple of different people like really got into my head as, "This is what you have to do. You have to go do this." Um, and I give them both credit. There's a saying that life begins where your comfort zone ends, and writing a book about venture investing wouldn't have pushed me to that place. I wouldn't have gone to a different place. This pushed me to a different place.

And, and I, uh, I approached it as a new hard project. So I hired a researcher, a co-writer. We read 100 biographies. We went through all the academic literature. We ran our own academic study with Wharton. We took it very seriously.

And so the idea that this was a talk that had gone viral, which probably, because you are pretty humble, exceeded your own expectations, is my guess. But then the idea to make this a book, combination of some external validation, some encouragement. And I like this point that I think you're making, which is it was at the edge of your comfort zone.

I found myself at this unusual conference put together by Chris Sacca and his wife. And they invite a bunch of—this is kind of like, for an analogy, they invite a bunch of people who would otherwise never meet one another. And Brian Koppelman was there, the writer—I suspect you know Brian—for Billions. He had this thing, I think he did it with everybody, not just me, where he says, "Try and do something you've never done before. Try and do something creative. What have you ever done that's creative?" He was like needling me, you know? And he needled me quite hard. And him and Tony Fadell were the two people that convinced me I had to lean into this as a life experience. It's interesting, you know, he's acting on The Bear now, which he had never done, so he's doing it to himself as well. He's a good character on that, and I agree. Maybe we'll talk about it later, but, but, um, I'm hearing some rumors that Tony might take a big job one day soon. I don't know. I might have spread those rumors because I could, I could only—I think it'd be pretty predictable what that might be, but, uh...

But yeah, let me finish that thought. So the listeners may not know, Tony Fadell did the iPod, was VP of engineering on the iPhone, and then started Nest, which he sold to Google for $4 billion. Probably one of the top three designers alive today, I think people would say, maybe even one. He wrote this book, Build, and he, he said to me, "It's the best thing I've ever done," and I just listed his accomplishments. And, um, I think he meant—well, I know he meant, because I talked to him about it, he just meant from a life fulfillment standpoint, like that it meant, it meant a lot to him, the feedback he got from sharing that knowledge. And so, uh, he was the other one. Those two people were the ones that really pushed me over the edge.

Well, life fulfillment, you know, the antithesis of that is life regret. And you've talked about this where something like 60% of adults, you know, are basically unsatisfied with what they do. So they're not happy.

We did a survey with Wharton and said, "If you could go back and start over, would you choose a different career path?" And 60% of people said yes.

And so you call it career regret, right? Consistent through line, Bezos' framework of regret minimization. Is the problem that people choose wrong or that the systems never really let them choose?

I think it's all those things, and I think it's gotten worse. So I think that the college matriculation industrial complex has gotten very grindy. I think everyone knows it. I think everyone would admit that people in our generation—and I'm a little older than you—but had way more free time when they were young to explore and learn and make mistakes and just, like, challenge themselves, whereas today, by the time you're in sixth grade, a parent's worried about your college application and they're filling your schedule immensely. These kids are way over-scheduled, over-programmed, and many people, you know, Jonathan Haidt calls it a resume arms race. There's a couple paragraphs in Rick Rubin's book where he just says he doesn't think children have enough time to fascinate, play, and... and there's... so there's a lot of people that are pointing to that.

And then, you know, you and I have discussed many different forms of bias and psychological biases. And one of those things is sunk costs. If you grind, you know, from sixth grade to graduation from college, all to get this degree in computer science, you feel pretty invested and not want to move away from that right away. It feels like, 'Oh my God, I've put in all this time.' And I meet a lot of young people today who come out of college burned out on learning. And they're almost like, 'Whew, I'm so done with that now.' And I think that's a problem as well, because the very best and the brightest, including the folk singer and the restaurateur and the basketball coach, are lifelong learners. And...

Parents have a very well-intentioned instinct to worry about their children's economic stability. And so they're very willing to encourage a career path or a major path that may not be what the kid is obsessed with or is fascinated by for that very reason. And I don't... In no way, shape, or form should anyone think I'm saying they're bad parents. I think they're extremely well-intentioned, and I think it's instinctive. I think it's in your DNA to do that. And I think it's very hard to do. I've got a couple of stories of parents—the parents that let them go try the crazy thing. I think that's very hard to do that.

I think it's also really important. And you, you highlight a few in this, but being exposed to sort of a panoply of heroes, you know, a pantheon of people that you can look up to and be like, 'Oh, I could be like that.' My mom wanted me to be a doctor or a lawyer when I was young, then it became a doctor. And you know, that was the conventional thing, right? To your point: stability, predictability, income, especially if you came from nothing. And it wasn't until I started to be exposed to these heroes that I was like, 'Wait, I want to be like that. I want to do what they're doing.' I, you know... And you find this passion.

I have a chapter on mentors, and people talk a lot about mentors, but I try and split it into real mentors and what you just described, which I call aspirational mentors. And I borrowed this from Danny Meyer, the restaurateur, when his uncle convinced him to completely pivot. I mean, he was not doing this at all, and his salary dropped by 10x to go work in a restaurant. He made a list of 10 people he felt were changing the restaurant industry at that point in time and started studying them. And you can just imagine anybody that's on the first rung of the ladder looking up and seeing people that they find aspirational, as you just described, and just start studying them. If you are on an intentional, high-agency career path, AI is a superweapon.

Because everybody wants to talk about AI and jobs, but if you're doing this, okay, I'm going to go create 10 profiles of these people. How hard is that? It's super easy. You can find YouTube videos and podcasts with these people, and then you can even just tell AI, "Pretend you're this person," and you start throwing questions at them. It's unbelievable what you could go do and what you could go learn in this modern world. So I think that's ironic that if you're a sitting duck, if you're in a job you don't like, if you felt like you're a widget and one of a hundred, AI is a problem. But if you're crafting your own path, it could accelerate you. And I don't know how to get people on a high agency path if it's not something they're fascinated with.

It's got to feel so easy to run at it.

Something has to also be, just as people have different genetic predispositions for risk-taking or for fitting in or for standing out, so many of the entrepreneurs that I've backed, you've backed, are very comfortable standing out. They're very comfortable basically failing. They're comfortable disagreeing with the consensus. And some of that might be wired. Some of them might be young experiences. You know, I say that chips on shoulders put chips in pockets. They're the people that—I've used that phrase so much on my tour. I always reference you, by the way. I appreciate it. But, but it's true. It's like, you know, like you take Palmer Luckey—uh, didn't go to college, you know, dropped out high school.

Like he's got such a chip on his shoulder and, um, he's got the competence to back it up and a good ethical moral compass, but, like, he's still picking fights with people that wronged him on Twitter 12 years ago that are, like, totally irrelevant and he won't let it go. And people are like, "Just let it go." And I'm like, "No, keep going because it's a fuel that empowers him to create companies." All right, one of the principles you have is Chase Your Curiosity, which is different than so much advice where people are like, "Pursue your passions," you know, "Chase your passions," but it's a distinction. And in venture, you see people who are, like, obsessively curious, but you also see people who confuse curiosity with, like, restlessness.

And so how do you tell the difference between

those two? I mean, one of the things I did, so the first principle, Chase Your Curiosity. I admit that the hardest part of figuring this whole thing out is just identifying that. And a lot of people don't get there. Angela Duckworth didn't figure out she wanted to be a—this type of professor that she is until she was 30. And I didn't make it into venture until I was 30. You have to be willing to explore and admit and test and not view that as failure. I went through two other careers and I didn't—I don't regret doing that. They were stepping stones for where I ended up, but I didn't view it as failure to leave them. And so I think, you know, one of the things I did is I went and found, like, 10 different methodologies for that process.

I think when you get there, you'll know. But the thing that will be the most obvious sign is this pursuit of information and pursuit of learning. And it will come very naturally. I like to throw out the comparison of comparing it to binge-watching your favorite Netflix show. Would you go read about this instead of doing that? And I think for the people that are the most curious about certain fields, they do that constantly. You know, "Would you rather—" Yeah, the Danny Meyer story, which is in the book and is in his own book, Setting the Table, um, his obsession with learning in his industry—like, if you think you're, you know, as good as Danny at that, go read, like, through how he goes about it. It's exhausting.

And he's still doing it. Like, we talked to him right before the book came out, and he had just come back from a trip to Europe with all his top chefs, and they're just on a learning tour. Now, that's a better learning tour than most industries, but, but a learning tour nonetheless. Um, it's just innate in what he does.

By the way, I've seen you do that, right? Like, you come into cities and you meet with interesting people in different fields, and it could be famous macro hedge fund managers, could be restaurateurs. I admire that a lot, actually. There's a humility, maybe comforted by the fact that you might have the access to be able to do it, but that sort of beginner's mind about all these adjacent sectors.

We have a principle on "own your craft." There's a principle on mentors, and there's a principle on peer groups. And in all of those cases, as you start to climb the ladder and get to a higher and higher rung, I think there is a—it's a more difficult course, it's not 101, it's more of a 400-level course, but you start to expand your learning, your peer network, and your mentors outside of your field. It's noisier, it's harder to gather insights, but when you do, they might be more impactful. And the second half of David Epstein's great book, Range, gets into how a lot of the biggest innovations come from people that cross-pollinate in that way. It's hard to do. I think I've seen you do it, but it's not something everybody—that's an advanced-level course.

I personally just have sort of such a wide range of interests that come from—and it doesn't come from a virtuous pursuit. It comes, arguably, from an insecurity that I want to be smarter than the next guy. Sometimes that is a liability. Sometimes I come off like a jerk or arrogant or something. But when somebody knows something I don't know, I'm like, "Oh, shit, I've got to know what they know." And then I, you know, and then you end up connecting dots in these disciplines, but probably most inspired by Charlie Munger on that.

And one thing you said right there, like, that is a, is a mindset of FOMO about knowledge. And one thing I would tell very young people is, especially when you're on that first rung and that second rung, if someone says something you don't understand, tell them right then. Like, say, "What? What do you mean by that?" I mean, yeah, I like—because there, there's an instinct that you're going to look like you don't know and therefore you're dumb. And, but, but, but, and all the greats talk about this, ask the question. They're going to respect you for asking it. You're not going to ask it twice. And you're going to learn faster. You just passed up an opportunity to learn something you didn't know. And if you ask it the right way, you look

You look appropriately humble. You don't look, you know, it makes you look good too.

And curious because, yeah, when you encounter situations with uncertainty, I would trust somebody that's like, okay, they're not going to just pretend and BS that they know how to get through it. They're going to interrogate it.

Yeah, and you can say like, 'Hey, maybe I should know that. I don't. I really want to make sure it's part of my knowledge set. Can you tell me more?'

great advice. One of the other principles you have is go where the action is, you know, and it's not where the puck is or where it's going to be. It's go where the action is. And some of that requires a little bit of EQ to understand, you know, because I don't know what one of my partners has a a bunch of friends that he grew up with and they're counter indicators. You know, they were the guys that, uh, in early 2000, we're doing the day trading and oh seven, we're doing the mortgage trading. Then they went to like life insurance settlements, you know? So there's a, there's an EQ between the people that really know where the action is. The eight plus eight caliber people versus like the transactional hucksters.

But, but either way, that's, it's generally arguably great and easy advice for the 22-year-old.

Um, maybe, you know, those people typically have no obligations. Maybe they got student loan debt, but what do you say to the 40-year-old, the 44-year-old that—well, let me make sure I, I, uh, ground it properly. The, the title of the chapter is "Go to the Epicenter," and the point I would make, and I probably got the most surprising amount of positive feedback from the early readers about this chapter—Tim Ferriss was fascinated by it—but, um, it basically says, like, if you are entering a career that has an epicenter, you know, theater in New York or movies in Hollywood or songwriters in Nashville or advertising's probably New York or Silicon Valley for high tech, if you take yourself to that place, um, once again, three of the, of the principles in the book, um, continuous learning, embrace your peers, and mentorship all get easier.

Like, and they don't get easier by a little bit. They get easier by maybe 10x or more. And, you know, if you're in Silicon Valley, and you have time, you can find an event every night. And at that event, you might meet a peer. You might make a connection you didn't have. You might hear about a company you didn't know about. And you can do it. The opportunities to do that are daily, daily. And on top of that, many people that are wildly successful will tell you two or three stories about a chance encounter that led to something that led to something and that they wouldn't be where they are if that didn't happen. And some people can push back on that and say, well, that's just luck, you know, but

The number of potential opportunities for luck go up tremendously if you're in the battlefield where everybody else is.

There's a great story of David Geffen told in his book or the book about him, which I think he didn't love, called The Operator. And his mentor, Ahmet Ertegun—I forget if it was Arista Records, but one of the major record companies—and he gets up and walks over to David Geffen, who's seated across from him, intentionally, dramatically, very slow. And David's like, "What the hell are you doing?" And he gets up and he walks back very slow, and he does it again. And he's like, "Ahmet, what, what are you doing?" He's like, "I'm teaching you that when you walk in New York and Hollywood, you walk slow because you increase the probability that you will bump into somebody that will change your life."

It's true. It's true. And not everybody can do that, but like, man, if you can and you're young, it's going to pay off. And there, I think, the, the counterargument is rationalization, which is you say to yourself, "Well, I'll be, I'll be the biggest fish in a small pond." And it's—I, I just don't think that works out. If you want to practice a field in a second-, third-, fourth-tier city, I would still say go to the major city first. Willie Nelson was in Nashville for a long time before he moved to Austin. Like, like, still, like, if you can and you're young, be in that place. All right. So, so you're, you're close with Michael Dell.

You've known him a long time. Yeah. He didn't go to Silicon Valley. It's true. But, but, but, you know,

You know, as a statistical guy, I think you always find one-off examples. Yeah, I think there's way more people that have fallen into Silicon Valley and, like, had amazing things happen to them. But it's true in these other places as well. There was a documentary on songwriters on Netflix that I watched. And just like Silicon Valley, apparently in Nashville, you could be, you can be there for two months and show up at some in-the-round thing and walk up to someone that's written, you know, gotten three, you know, awards for their music. And they'll still talk to you. Like, they'll still give you advice if you do it the right way. And it's just, it's my favorite thing about Silicon Valley is the number of people that will take the time if you ask them.

It still shocks me today how easy it is to do that there.

Um, Wired magazine editor, who I think is one of the great tech philosophers, Kevin Kelly. I don't know if he coined it or Brian Eno coined it, but this idea of scenius, you know, the scenes where genius assembles in, in clusters. Buffett didn't know that word when he was talking about it, but when he wrote, you know, "The Superinvestors of Graham-and-Doddsville," it's like, what do all these people that are outperforming and compounding the market have in common? They're all going to Columbia and taking, you know, Graham or Graham's class. Right. So yeah, the, the Buffett-Graham story we have in our mentor chapter, a small version of it, but you, you, you, you've called the, the, um, the thing we were talking about before the career-industrial complex.

Um, so you got universities, recruiters, the corporate structure, they're all funneling people towards these like mismatched roles.

And even, even if not mismatched, they look a lot alike. When, when I wrote the book, I thought a lot about the career placement experience at a campus. And you're signing up on a list with like 30 other people to all get 15 or 20 minutes with this recruiter. And I said to myself, one, I remember thinking this back both at undergrad and grad school. One, what are the odds that my dream job company is interviewing here? And two, what are the odds I can differentiate myself in that type of framework? And, you know, I went to New York and knocked on doors and begged for a job that didn't exist. And by the way, I don't blame the schools. They have to do something that is equivalent to mass production.

They can't help every single individual do a career-craft experiment. It's impossible.

So I'm going to ask the question, but just as a side anecdote, but the guy who runs my IR and our fundraising, you know, he's got like balls of steel when he goes up to everybody and it's just a great virtue I don't have. And he wanted to work for Steven Spielberg when he was graduating college. And there was no recruiter for that, you know, so he figured out, okay, this is where he works. And there's some other offices in the building and he stood at the elevator and just waited until Steven Spielberg would come out and then pitched him and was so persistent and presumably annoying that he was like, "Fine," and brought him on.

The Tony Fadell story of his first job in Silicon Valley is that on steroids. Tell me. I don't actually know it. It's in the book. He was entrepreneurial in Michigan. He knew he needed to be in the epicenter. He read a Rolling Stone magazine article, which I just sent, I found the copy on eBay and sent it to him, that mentioned the stars of Apple. These were the individuals of Apple. And they had all left to go to a company, General Magic. He didn't know what they did. He did not know what the company did, but he read that article and basically stalked them for six months, passed up every other job offer he had, including one at Apple, waiting and hoping to get inside those walls. And your listeners should

walk, not run, after this is over and watch the General Magic documentary and see, you see a very young Tony Fadell. There's a ton of video in there, and the company failed, but the people in that movie went on to do some pretty amazing, great things. And so it just shows you like putting yourself in that place. But once again, the hustle level is unworldly, you know. And, you know, Dylan hitchhiking to New York to meet Woody Guthrie is pretty up there as well, probably the boldest mentor pursuit ever, ever started. Wow. Um, Jon Haidt blurbed your book, mutual friend, and, uh, you know, he, he's talked about young people basically

Arriving in their twenties and being totally ill-equipped, you know, full of anxiety, less ability to focus. He attributes it, of course, you know, to tech and social media. Do you, you know, you, you have seen older entrepreneurs, you've seen, you know, mid-career entrepreneurs, you've seen young people, you know, I feel like you have literally an Above the Crowd view, vantage point. Do you think that Gen Z right now is more or less equipped to follow your playbook than my generation or, you know, older folks?

I mean, if I read what he's written, not just in The Anxious Generation, but in Coddling as well, you're not setting someone up for high agency. And I do think that the book requires a pivot towards high agency. You have to believe you can be successful. And I hope that the way we wrote the book and the inclusion of the stories, it was all very intentional to get you to that place where you believe you can do it. If you're completely of a mindset of being a victim of, of, 'I can't win, you know, it's too bad. It's everything stacked against me,' I don't know that you'll, I don't know that you make it to the end of the book. I hope you would, but it would be a transformation, for sure. Um, you know, yeah.

I think you need agency, for sure.

You mentioned this before that it was pervasive or surprising. People would be surprised how pervasive it is in the Valley of giving back, which is one of the principles, always give back. What's the version of giving back that you think people underestimate?

The thing I think they underestimate the most is how early you can start. They assume it's something you save for retirement or the last five years, because they think of giving back solely as a form of philanthropy, something you would do with money. And the truth of the matter is that you can, you can express gratefulness from a very early stage of your career. And I think if you get practiced at that art, you will do it a lot. And you'll just find yourself, you know, when there's an opportunity to drop a handwritten note or send a gift, or, you know, I—one thing I tried to do on my way up, whenever I hit a, some type of success point, a new career, a new job I landed, I would think of 10 or 20 people that, you know, were helpful to me getting there and send them a note with a bottle of wine.

"I just landed at a new job. I think you were a key part of me getting here." And, um, I think if you make that a habit, I think you'll be exposed to a much stronger, more vibrant support network. And I also think there's just good karma that comes from it, to kind of pay-it-forward style. And if someone gave you advice on the way up, take the time to do it back the other direction. And I just think you'll have a more fulfilled life. I think you'll be more successful. One of the things that's amazing about Danny Meyer is how many people you'll meet if you talk to chefs around the country who rolled through New York and hadn't had a chance to work for them and what that means on their resume to them.

You know, like they were a part of that thing. And if you get them talking about it, you see this huge smile come on their face. So he's had this impact—I call it like a boat wake—on the industry based on all the people that he's touched along the way. And I can make an argument that's a better sign of success than even awards and accolades, like how many people you touch in the industry.

Um, I want to talk about a few of the characters real quick and then, and then I want to ask a few more questions. But, um, one of the things that I thought was interesting with the Danny Meyer, um, focus was, um, he remembers viscerally like this, this meal he had right before the LSAT. Yeah. And, you know, he's doing really well, he's making a lot of money, and then he quits to open up this restaurant, and you open up with the—you open the book with this sort of anecdote. Um, what does it tell you about the way that people in the book particularly remember the moment that they almost took the wrong path more vividly than the moment that they might have taken the right one?

Well, I'm sure, you know, there's this, when we go to bed at night, like we ruminate a bit about things and the, as I mentioned earlier, like, when we make mistakes, we're very easy to let ourselves off the hook. But when we miss out on something, it weighs on us, like it weighs on us heavily. And so I actually, in that case, I think Danny's that way about every meal he eats, especially if there was some reason to remember it. And when he went through Europe working as a stagiaire, he kept massive journals. And my takeaway on all that is, I think almost any career pursuit can be considered a craft. And I think if you are truly passionate and fascinated by something, you will want it to be a craft.

And nuance matters for craftsmen.

On the craft, you've got Magnus Carlsen, you've got Seinfeld, you've got Buffett, all people who clearly have honed their craft over a very long time.

But I'm making a different point real quick, Josh, and—and then I want your question. Danny cared about the details at a level that most of us wouldn't. And if you are obsessive about something, the—those details are super interesting to you. Jobs, in his graduation speech at Stanford, talked about the calligraphy class that he taught—or he took—and how much it weighed on his brain. Now, most of us, if we took a calligraphy class, wouldn't, like, we'd be like, "Eh, that was okay." But it fascinated him, right? And so that's my point is, like, it's possibly a sign of what you should go do if you—if the details of something matter to you. That's what I was getting at. That's a good, profound point.

I was mentioning Magnus Carlsen and Seinfeld and Buffett who, you know, were nobodies and then just compounded literally and figuratively. It feels at odds with Silicon Valley, where it's a culture that largely values speed, moving fast, breaking things and, you know, to sort of absurdity, you know, ad absurdum, but ship fast, iterate, move on, fail fast. Are those two things at odds?

Well, I mean, the one thing they all do do, Josh, is they all learn about the new disruptive thing, like in an obsessive way. And the way the best entrepreneurs have shifted on AI. I mean, look, I mean, one, I'm such a huge fanboy now of Bret Taylor, and like his whole evolution. But just go listen to the recent podcast he did with Jack Altman and listen to—he's repotted himself as an AI expert. He wasn't one, like, when the AI starting bell went off. Like, anybody could have done that, right? But so I do think the entrepreneurs are obsessive learners about disruptive technology. And I think it's instinctual to them. You know, they just run at it.

I want to ask about not just chasing curiosity, but purpose. I've got a friend who, um, at dinners on Friday nights in his home, it was a really beautiful thing that he said, you know, I, we wish they, they say a prayer for their kids at Shabbat, but they were like, uh, and I'm not religious as you know, but they said, you know, we say a prayer every Friday and we wish our kids a life, not of success, but of meaning. And I thought that was a really profound teleological end goal, you know, that I never really thought of. I don't care. I don't want my kids to be bankers, lawyers, conventional stuff. But I want to ask you, your parents, what did they expect of you? What did you feel they expected of you?

What did you expect of your kids? Did you want them to be... And then at some point, you know, you started later as a venture guy, but you achieved extraordinary success. Did your expectations for them change as your success changed?

Yeah. I mean, my parents did not put overt pressure on me in any way, shape, or form. What did your mom and dad do? Um, my mom was a substitute teacher and mostly a stay at home mom after that, but, but didn't really got into civics. So she, the last 20 years of her life, she was an Alderman in the city and ran the school board and all those things. Um, my dad, uh, took a flyer. He, well, first of all, my dad had a dream job. He fell in love with gas powered airplanes when he was a kid, like fell in love with, and. I've got an aeronautical engineering degree and was working in a wind tunnel in Langley Air Force Base. So he was doing it like he was doing what he loved. And then he took a flyer, a version of go to the epicenter.

50 of the people at Langley got offered a job at the beginning of NASA in Houston, and he took it. And I don't think he ever once said to me, 'Oh, go take a leap like that.' But having known he did, you know, most of my friends didn't leave the state, you know, and I thought nothing of it, you know, thought nothing of it, you know. And I think, yeah, I think if you, if you live in a family that's been in a place for a very long time, you probably don't feel like you have the permission to leave, or you might be intimidated by the notion of it, and, and I didn't have that, so I credit—

I do think that mattered, you know? And for your kids' expectations? Yeah.

I mean, I'm trying to live the book as much as I possibly can. So we'll see. Um, I don't think any of them are right on top of their dream job yet, but one of them got a Mech E degree at Carnegie Mellon and came to us the summer before his graduation. He said he's convinced he wants to teach, and he's in Teach For America now. So, so that—I hope I'm living it.

Let's wrap talking a little bit about SFI, the Santa Fe Institute, where we're both trustees. And I've admired your—and you've highly recommended to many people—Complexity, the Waldrop book.

Someone posted today that they hope my book wasn't as dense and hard to read as Complexity. So I will tell people that they are very different. I think my book's very readable and approachable. They are very different.

But what drew you to SFI, and do you see any of the principles from your book? You know, obviously chasing curiosity and peers.

Yeah, I mean, I got drawn to SFI because I met a lifelong peer who's a friend of ours, Mike Mauboussin, when I started as a sell-side analyst in New York.

To me, it's like the epitome of a lifelong learner, you know?

Yeah. Oh, and we became book sharers. Like we would, after I left New York, we would touch base every month or two and say, 'What have you read lately? What have you read lately?' and just exchange. We're going to get to that. We're going to get to books and movies. And so I, um, I did that with him for so long and we devoured, um, complexity. And at that very moment, he was introducing me to Bill Miller and we visited back then. I mean, I was 30 and he stayed with it and Bill did. I got drawn away into chasing my dream career, but was able to come back. And I was also, you know, the Brian Arthur piece, the Brian Arthur piece really did impact my whole career.

People that don't know Bill, Bill Miller, um, was one of the great outperforming mutual fund managers, like Legg Mason, but, but was really into SFI for figuring out what are some of the timeless principles of complexity and emerging phenomenon that could be in power laws and earthquakes or how ants forage and find things that might inform the investment process and give him an edge.

I think it's all a search for edge, but, but, you know, also just raw curiosity. And, um, it is this advanced level course thing. You're trying to learn very far away. And, um, anyway, the Brian Arthur piece that ended up in Harvard Business Review, I was already reading Brian before that was published because— On increasing returns. Yeah, that impacted my venture career. I mean, I became known as the marketplace investor and it's all tied back to having a raw confidence in that philosophy. So I think I discovered something at SFI that had a direct role in how I approached my whole career. I'm not saying everybody would, I mean, but I did. So, yeah.

My wife was interviewing Paul Singer at this conference a few weeks ago, and she had gotten some inside scoop as a story that he was pitched for $2 million. I think he could have owned 10%, maybe it was more, of this little business from this D. E. Shaw guy that was starting up, and he passed on it. He didn't see it. That was, of course, Amazon. The irony is Elliott, I think today, is the largest physical bookstore owner in Barnes & Noble. Was there an investment that you— Oh, sure.

that you passed on that you look back and you're like, 'I just...' The pattern recognition or... Um, I think pattern recognition got in our way. So I had Larry and Sergey present to the Benchmark partnership shortly after I joined Benchmark with—

The company had 25 employees, Google. Was it a friend at Stanford that tipped you off?

No, I think I was using the product. I think it was just being one of these people. My whole career as a venture capitalist, if there was a product that was... anybody was talking about and I didn't know, I had immense FOMO. And, you know, one of the reasons I left was I kind of felt worn out by that FOMO. I couldn't take it anymore to even download another app. My phone has like 14 pages of apps. But, um, yeah, so I think that the—the flip side of this, so anyway, our mental models that, you know, two PhDs want to be co-CEOs, uh, Yahoo had fallen from 82 to 10, Excite was in bankruptcy, there was a lot of ways to get yourself in trouble. But Doerr and Moritz did it, like the top two VCs did it. So I think that I came out of that with a little bit of your chip-on-shoulder situation and a little bit more having a higher recognition of an asymmetric risk in venture.

And that missing an outlier cost you a thousand X or more than a loss. And you've got to rewire your brain that way. And Bruce Dunlevie in our shop started saying, 'What could go right?' as a theme. And I will tell you, from that day on, we never spent much time talking about the failures. We never beat up a partner because a deal didn't work, but we would once a quarter study the deals we didn't do ad nauseam and talk about why we either didn't see them or passed on them, or like that was the error that we wanted to minimize.

Yeah, the permanence of regret is painful, such that we implemented a decision-making process where everybody gets one in a fund of the partners, where if everybody else doesn't want to do it and one partner is so table-poundingly insistent and passionate—because in our case, it was Cruise, Cruise Automation. Right, right, right, yeah. And one of my partners was insistent to do it. I think we offered him... 12 of 20 at a 40 pre, 60 post. Sam Altman was in there. He was like, 'You can get a better price.' Spark offered money at, I think, 20 at 100. And I was like, 'That's too much. This is nothing yet.' And I was opposed to it. During diligence, we introduced him to GM. And GM was like, 'Yeah, it's pretty interesting,' or whatever.

Anyway, fast forward a few months, um, nine or nine months, ten months, GM says, um, 'You know, we want to invest in the company.' And so Kyle, who's a very good guy who's running it, said, 'Uh, all right, well, you know, we'll take 50 million.' And, um, and they left blank the ownership percentage, and Kyle filled it in and wrote five percent and sent it back, implying a billion-dollar valuation up from 100. And GM then said, 'Well, if that's the price, then we should talk about buying you.' And it would have been an 11X in nine months or whatever. Anyway, my partner, Shahin, who really was responsible for that, was so pissed that we made that decision—you know, discipline, don't pay the high price for it, missed it.

He would pound the table every time, you know, demanding this sort of heightened credibility. And so we implemented this process like, 'All right, you get one from now on. We don't want to hear about it anymore.' 'Yeah, that's what it is.' 'Yeah.' All right, books and movies. What have you become obsessive, curious, or conversely, what can you not believe people are obsessed with and watching? Let's start with tech. Landman, yes or no?

yeah but i mean part of that's because i'm uh i've been a lifelong alternative country music fan like big time and the woman whose nickname is avon that works for for the producer um she picked all the music for yellowstone and all the music for landman and like really good yeah and like there's this kid out of dallas tanner usury that i've had perform at a few events three of his songs are in landman like like she just has a way to find this stuff that is amazing and and billy bob's a badass i mean It's not for everyone, I'm sure. I really like Pluribus. I didn't know I was going to like it. And I like the sci-fi part of it. This notion that everybody knows everything everyone knows. There's a

certain part about AI where I think most humans don't realize they can ask it in so many different places. People ask me questions all the time where I just say, 'Well, did you ChatGPT that? Like, why would you ask me?' Like, and so I think it's good. I think it'll be a different world when everyone realizes the information's at their fingertips. I don't think people have really embraced the notion yet. We, we've talked about, you know, as a society forever, right, this global brain, but it really does feel like we do now have this global brain, and yeah, it's interesting.

So I enjoyed that one. The art imitates life. I just put out my quarterly letter. And one of the things I had in there was in the '20s, you had The Great Gatsby, which was really around '23, '24, '25, but it was four years before 1929, which Sorkin just chronicled amazingly. Then you had Wall Street, which was, I think, '85, '86, but before the '87 crash. You had The Social Network, which presaged and preceded the Facebook IPO. You had, uh, then the tail end, the bookend of that sort of moment, right, um, was, uh, uh, Super Pumped and, and WeCrashed and, um, uh, The Dropout. Uh, and by the way, my wife was obsessed with your protagonist, uh, in, in mine too, unfortunately. I think they're one of many, I think.

By the way, that soundtrack was awesome with all the, you know, early-nineties grunge, Pearl Jam, and all that stuff. But, um, but I actually invoked Landman because we went through the, you know, the Billions and Silicon Valley and, um, um, even, you know, the Space Force one. And there's something about that moment that maybe I'm extrapolating and taking too much poetic license of Landman, where we are going from the nerd of move fast, break things to like physical assets, politically connected infrastructure. There's something that I feel like it's going to portend.

Yeah. And, and, and he, he's appropriately the cynic, like maybe you and me are, but like when he's talking about wildcatting, he's like, "I've never—" he says, "I've never wildcatted a day of my life." It's so good. It's so good. All right. Other, other books aside from yours, which I, by the way, one movie you didn't mention that I thought was like 10 years ahead of its time and just remarkably well acted was Her. I just, I don't, I'd have no idea how they could be so kind of spot on and how he did that role. I don't know how he did it. Like, but it's just incredible.

This is a trend that I'm paying a lot of attention to. And it's one of these things where you don't even have to speculate. You can observe, which I call lifelogging, which is we're all gonna have, and some of it is gonna be generational comfort, but we're gonna have AV devices that are passively recording your entire day through audio. Meta just bought that one, Limitless, the pendant. Amazon bought the V. Um, there's, I don't know, five open-source ones. There's, you know, and then Jony Ive and Sam and, uh, you know, working on whatever devices. But there's going to be really interesting components from, you know, DSP and memory and microphones and MEMS and all kinds of stuff that go into those devices. They proliferate. 99% of them will fail, but there's an interesting moment in this, um, you know, wearable device integration with, with, uh, all the foundation models.

Um, but her was that right. And that was, I don't remember what year, but early two thousands, late nineties. It was way ahead of open AI way, way ahead. Totally. Yeah. Um, any, any, uh, both timeless books that you insist everybody read and then fun ones that, you know, contemporary.

One thing I will share, maybe as a teaser for the audience, at the back of the book, I have a list of my favorite books, which is—I should have counted them, but it's somewhere between 35 and 50. So it's not zero. And so I'll point people to that. I've been reading David Epstein's unreleased book, which is fun when someone gives you that, called Inside the Box, which is a clever title. It's about how constraints drive, um, creativity. And the—and maybe I'll end on this. I had a takeaway from it that it's not in there, but it's what I like when a book causes you to think differently. I think the world has been trying to figure out how Elon does what he does, especially from a leadership standpoint. And Collison on the Shandy Pie episode recently, you can just see him poke.

I mean, you're listening, but he's just going and going and going. And the time thing comes up. And I had read in—I was just telling David all this yesterday. I had read in the Isaacson book that he loves to, if the period of time someone would normally ask a question was months, he'd go to weeks, or was days, he'd go to hours or minutes, such that someone would say, "When will the next version come out?" He'd say, "How many days for the next version?" instead of months or whatever. And I realized what he's doing is the exact—Jobs would tell them the phone has to be this thick, and then their mind can only operate within that constraint. And Elon's doing that with time. You're never gonna figure out how it could possibly be done in two days unless you're told it has to be out in two days.

Now, what do you do? And now you're gonna all of a sudden think of a whole bunch of things. You're gonna look around walls you wouldn't have looked around before because you don't have any other alternative. And so anyway, I thought that was interesting. He helped me solve one of the Elon mysteries without actually describing that particular thing. And I then was able to share back with him someone using time in that way, which I thought was super interesting. Super. Bill, great to see you. Good to see you. Thanks for having me on.