Bill Gurley - Benchmark Partner, Backed Uber, Zillow, Stitch Fix | The Conveyor Belt That Ruins Your Life

I was an engineer. I had an engineering degree in undergrad. In my second year, we were starting the third project I had worked on, and this probably isn't what I want to do. After a couple years, I thought to myself, "Is this what I want to do my whole life?" I got to know.

What does it take to spot the next big thing before anyone else does? Bill Gurley is the venture capitalist whose intuition has shaped the modern tech landscape. As a general partner at Benchmark, he backed companies like Uber, OpenTable, and Grubhub long before they became household names.

58% of people say they're not engaged at work. 15 of those 58 say they're quiet quitting. These are horrible numbers. Founders live on the edge of a new technological shift constantly, and they can't not know what's happening next. It requires a level of studying that is foreign in other industries and other fields. Most people, when they go home from their job, they don't study more about what's next in their job. He's not driven by hype; he's driven by insight, discipline, and a deep understanding of how markets evolve. His career is proof that great investing isn't luck; it's vision sharpened by rigor. If you're in your dream job already, embrace AI. You want to become the superhuman that is what's new on the edge. You should be self-learning. If you're not in your dream job and it's threatened by AI, all the more urgency to jump out.

Bill, so you spent 25 years investing in the best founders in the world, and then you chose to write a book that has nothing to do with venture capital. So why?

You know, it's funny. A lot of people ask me that question. And when we went out, when I—when I decided to write the book and I went out and talked to agents and publishers, I'd say 80, 90% of them ended up in a non-connection because they would constantly steer back towards, "Don't you want to write a venture capital or a tell-all or how-to-invest book?" And I didn't have any motivation to do that. I can't explain why, but I didn't have any motivation to do that. This started about... ten years ago. I was at a moment in my life where I was consuming tons of biographies, which I think lots of people have that thing where they read a great biography and they want more and more and more of them.

And I was reading a biography and noticed certain patterns about this individual's process and how they went about life, learning, and how they went about connecting, and how they went about executing their career. And I noticed similarities between three backgrounds that were very, you know, unique and and different in the industry they were tackling, but the process and points were very similar. And, you know, I've—venture capital is a game of pattern recognition. So you're constantly out there trying to look at how the new world's evolving and what the key patterns are. And I've been a writer since I was a sell-side analyst. I've had a blog for a long time, and I would constantly try and see patterns and then—and then bring them together and write about them. And so that process was something I'd done a lot, um, when—when—when this clicked for me. So first of all, the—the—the three people were, um, one was a folk singer, one was a basketball coach, and one was a restaurateur. So they're not even, you know, they're not like in the same domain category. They're not in the same domain, and they're all in domains where your parents would tell you not to pursue this job.

And they're all in domains where people would tell you you can't make money. And yet these people went on to exceptional greatness. Wealth became a part of it. I don't think any of them started for wealth in those areas. And it touched me in a way where I was like, "Wow, that's a cool unlock." Like, that there might be some things these people are doing that other people aren't doing and that haven't been written down. And so I initially thought this would be a great presentation to give to people, someone maybe at like an MBA class, because that's a point in your life where people that go to MBA school have a very unique opportunity to shift careers if they wanted to. So anyway, I gave the talk at the University of Texas.

They put that on YouTube. It got several hundred thousand views. I started to hear from, you know, people that had changed their lives. A few people who are in the personal development space, like James Clear, noticed it. And, you know, it gained momentum. And people said to me, "You should turn it into a book." And one person in particular said, who is very outspoken about trying to encourage people to do creative things, when he heard I had this kind of in the can, he like pushed me, like, you know, and he does this with a lot of people, but like, so you started with the question, "Why is a venture capitalist doing this non-venture capital thing?" He, he, he like really kind of shoved me in the back and said, "No, this will be good for you to go do this non-venture capital thing." So it's a passion project. It's something that, that I've now spent six years working and, and studying and learning and enhancing from the presentation.

I'm working with a co-writer and I hope it's awesome. I've gotten a lot of early validation. The goal, the sole goal of it is to unlock human potential, like to get people who maybe didn't have the gumption to go do this thing, particularly if it's in a field that doesn't feel like you're supposed to be doing it, and see if they can go change the world. And not only change the world, but I think all the stories we have in the book are of people who, once they're successful, have huge impact on others. And so it's a passion project with, hopefully, a very noble objective function.

I think there is a hugely noble objective with this. And I think that that's also why it resonates with so many people. Because the question that you asked me, like, do you enjoy what you're doing for a living? And the question of like, do you like your job? Do you like your career? you did research on this and 70 of people that you research in this 10 000 person study that you did for this book did not say that they enjoyed what they were doing that they wanted to sort of like if they could sort of restart right yeah and i think that i think i'm very fortunate because i said like yes i do enjoy what i'm doing but that's obviously not the majority so this is why this idea resonates with so many people because i think a lot of people

I've thought about this a lot. I feel like people start in a career and like time just flies, like time really just flies. And then they look up and they're 40, 50-plus sometimes. And, "Where did my life go? What am I actually doing with my life? Is a career that I'm in even something I want to do, or is it what I was pushed into after college or university? Is what my parents wanted? Is it what just, like, pays the bills and I'm, I'm scared to do something else?" So I think that's why it hits home with so many people. Um, I have to ask you, was there a point in your life where you were in a career that you absolutely hated? Did any of writing this book take you back to a point in your life?

Yeah, I think there was an undertone. First of all, my career as a venture capitalist, I adored. And I'm still kind of at the tail end of it, but I loved every minute of it. And I would often say in interviews, you know, if we lived in a socialist world where everyone got paid the same for a job, I would still want this one, you know, because I had so much fun doing it. And I had two jobs before that. I wouldn't say I hated them, but I was an engineer. I had an engineering degree in undergrad, and, um, you know, in my second year as an engineer, you know, we were starting the third project I had worked on, and it looked like the second, and it looked like the first. And I was seeing a bigger, broader world out there.

And it was like, you know, this probably isn't what I want to do. And so I went to MBA at University of Texas. thought about venture a little bit while i was there but it looked very hard to break into and i went to wall street and i was a wall street analyst on the sell side i had a great time met a lot of amazing people a sell side analyst gets connects it immediately to ceos and cfos which is insanity, you're 27. But after a couple of years, I walked around the office and I thought to myself, is this what I want to do my whole life? And I got to know, I got to know. And that eventually led to me getting into venture. So I do think one of the things that's important, and I want to come back to some of the data that we stirred up, but one of the things that's important

is letting young adults know that it's okay to try a career and stop. And Dave Evans, who wrote Designing Your Life, talks about this a lot. They have data in that book where, I won't get it exactly right, but five years post-college, 40% of people are no longer in the career that their major was. And then 10 years after, it's like 60%. And no one tells you that when you start. And it all feels like you're on this kind of treadmill, and we call it a conveyor belt. Like, you don't know that you have that flexibility. And so the weight of the direction you're running feels very heavy on a young adult.

And then I think that also there's all these expectations that they feel that they have to live up to. And they don't know where those—maybe they do know where those expectations are coming from. Maybe, like I mentioned, it is your parents or your peers or your guidance counselor or your professors or whatever, but you have all these expectations, and then you actually start running a race that isn't even your own. And that's what I think a lot of—I think if we talk about the data, the data is shocking, but also kind of sad. And I think that you probably felt the same way because you ran this survey twice because you didn't believe the data when you first ran this survey.

And by the way, we started reading much academic research. There wasn't much data on career regret. We launched a Survey Monkey survey of 1,000, but eventually to make sure it was hardened, great academic work, we partnered with Wharton and did a much broader one. um ours was seven and ten theirs came back six and ten i mean it's still majority don't like what they do for well the question was if you could start over would you do something different the gallup uh poll does an employee engagement survey every year those numbers are at 15-year lows right now um there's this whole phrase quiet quitting you may have heard about which they say like 58% of people say they're not engaged at work, and 15 of those 58 say they're intentionally trying to undermine the organization.

But these are horrible numbers. But I do think part of the problem is the... very well-intentioned people that want the child to be as successful as they can possibly be. And in the book, The Coddling of the American Mind, Lukianoff and Haight call it the resume arms race. But like, about sixth grade, parents take on an enormous amount of anxiety about their college application and whether it's going to be full or not. People always say, 'When I was young,' but when people were younger, they came home and they left the house and they went and ran around the neighborhood. These kids today have their life scheduled from when they wake up to when they go to bed. And it's lacrosse, and it's cello lessons, and it's the foreign language, and it's volunteering, and like, all to build up that resume.

And, and then it just starts compounding and going faster and faster and faster. One other thing that's happened that I think is, is unfortunate is that many universities now require you to apply to a major as part of your application. So you used to go take core classes for two years, and then at the end of your sophomore year, declare a major. Now you're telling a junior in high school, you know, 'Do you know what you would want to do? Do you know what you love?' They really don't know. And I've watched people ask these kids, and they're not—they're not—they really don't know. So they just want to say, 'I'm sorry, I don't know,' but they're not allowed.

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You get thrown into these situations where, first of all, it's very expensive and there's a lot of pressure. And again, your whole circle and peer group is saying, 'This is what you have to do.' Like in my family, the expectation was just get a degree, like just to get a degree, right? It doesn't really matter what you do, but then that shapes it. When you just get a degree, that does shape, to an extent, where you're going to end up in your career. And there's so much pressure early on, and you're trying to—you're trying to navigate it. Your parents come from a different generation where there wasn't—I don't think there wasn't the same kind of pressure. Like, now I feel there's so much pressure to pursue higher education, to—and there's not just pressure, but there's so many different choices, too, in career, right? So there's pressure with choices, and it just makes for like a really, I think, for a young kid, like a very stressful environment, right? By the way, we, we, um—

we we talk about this in the book where up through like 10th grade 11th grade you don't make a lot of choices and then all of a sudden there's 2 000 colleges to choose from in all these majors like it just opens up like like crazy and you don't know you don't know what to do there's a there's a uh I found this great quote from Rick Rubin's book, but he says, as children, few of us are taught to understand and prioritize our feelings. For the most part, the education system doesn't ask us to access our sensitivity, but to be obedient, to do what is expected. Our natural independent spirit is tamed. Free thought is constrained. There's a set of rules and expectations put upon us that are not about exploring who we are or what we're capable of.

Love this, and I don't think that's intentional. Like, I, I'm not mad at the parents or the college counselors or any of that. I just think it's a big system that has evolved to this place, and I'm hopeful that we can get a few, you know, parents and, uh, and career counselors as readers of the book just to open the aperture of what's possible, you know, to start thinking about the things in a different way. If you look at—

Was it a personality trait? Was it exposure to people? Was it this inflection point in your life where you had the courage to pivot careers and to make different choices because you were on a path and then you pivoted and then you pivoted? So, I mean, why did you do this? Why did, for example, even I do this when so many people stay stuck in one thing far after it sort of expired?

One thing I... I give a lot of credit to my—my father was—grew up on a rural farm in North Carolina, fell in love with model airplanes that took him to NC State where he got an aeronautical engineering degree. And he was working at Langley Air Force Base. And, um, he got invited to move to Houston and help be a part of the launch of NASA. And he, he took the leap and, um, he, he's, he's still here. I, um, I was just with him last week, but it, uh, that knowing that he did that and knowing the outcome from it and how it shaped his whole life and our community. And just so much came from that. I think it just gave me permission, you know, and that's a word I use a lot talking about the book.

Like, I want to give people permission to do something that feels a little bit risky, that feels a little bit, uh, ambitious, and, and, and feels, um, like maybe it's something they shouldn't be doing, you know?

Do you feel like there's traits that people can borrow from successful founders in their own career?

Sure. One of the things we get into a book and in the book a lot is just how you think about learning, you know? And I've never, you know, founders, live on the edge of a new technological shift constantly, and they can't not know what's happening next. And it requires a level of studying that is foreign in other industries and other fields, not to the people we profile, but to most people. Like most people, when they go home from their job, they don't study more about what's next in their job. It's just not what they do. It's not a common trait. All the people in this book and all founders have to live in constant fear that there's something new on the edge that they don't know.

One thing that I've always—this is like a working thesis, and you work with a lot more founders than me, so bear with me if you agree with this or not—but I've always thought that the best employees could be founders in another life. For whatever reason, that's just not the season of life that they're in right now. So when you hire somebody, the people that are going to kill it in their career, they are ambitious. They are curious. They are self-taught individuals. They're people that are always trying to do the next thing or even break what's working now so as to build something better, even in their own job or in their own life. They adopt a lot of the same traits that a successful founder would have, but they just do it in a work environment because that's the place they want to play in right now.

So I think that... And when I think about the most successful people who have had the careers that are fulfilling, that they actually enjoy, they act like founders, even if they don't have the title.

And you touch on something that I spend a lot of time on in the book, which is I think that in order to be great, you want to learn all the bedrock principles you possibly can. But then once you know those, have the independence of thought and the confidence to innovate on top of those principles. So it's not ignorance of the past; it's full understanding of the past, with an appreciation, the self-learning, and the ability to do something different. One of the things that I think would make many employees bad choices of founders is if they get the first-level rote knowledge and then they just apply it all the time and they don't have curiosity and they don't evolve. But I see a lot of people execute that way in life, and you can get through, but you're not very dynamic.

When somebody is in a career right now, and they're very aware that they're not happy, they're unfulfilled, they're in the 70% or the 60%, depending on which study they're part of, right? What is the new mental model they have to adopt? How do they change the way they view the world? What's the action step they gotta take? Because the first question would be, 'Oh, this is great. I'm not thriving in my career. I have a mortgage. I have a spouse. I have kids. I have all these payments. I have been doing only the one thing for the past 30 years. It's great to pontificate on a podcast that I should be learning all these new skills. Understood. But how do I actually change my life?' And I think that that's where...

The theory, at some point, has to come in contact with reality.

I think that it's obviously easier for people younger in their career. And that's the same for starting a company. Like, the more you get locked into obligations like you described, you do start to reduce your own flexibility. Although, I want to come back to that. So... so I do think it's better for young people, but three or four things I would say. One, recognize that lots of people, lots of successful people start in one place and move to another. This is the stuff that Dave Evans talks a lot about.

It's okay to change. Permission again.

Yeah, you need the permission to do it, and you need to think that it's possible. Yeah. The hardest part, I think, of all the stuff we talk about in the book—we have a chapter titled 'Chase Your Curiosity'—people talk like, 'Find your passion.' I think it's the hardest part. If you don't have a calling, it could be forced. It's like there's some entrepreneurs, 'I'm going to start a company,' and they just kind of force-start a company versus, like, really having an aha moment. And I think you need the aha moment. But I have a test that I think is the right test for whether something is the type of passion where the tools in this book could help you be successful. And that is simply: would you spend time outside of work learning about this topic?

Would you pick up a new paper on this topic and not watch 'Breaking Bad'? Does learning in this field compete with entertainment for you? And if that answer's yes, I think this is your thing. I really think this is your thing. And I think if you're in a field where you have that level of curiosity, you're gonna do extremely well. Almost whatever the field is.

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The guide is free to you at NetSuite.com. That's NetSuite.com. I like to talk about obsession a lot because obsession, for me, is such a fun idea in a good way—like a good obsession. It's like, okay, so if I'm running a podcast, like I'm up until three or four in the morning, like researching how to ask the best question, what does this setup look like, what is like—what are the clips with the hook, the first three seconds of a clip, and how does that perform on social media so I can market this show better, right? Like, I just get obsessed with it. So I know that I'm doing my thing. I know that I hopefully am thriving in a career that I actually love.

The reason I'm smiling is we have a section in the book about Jimmy Donaldson, who's MrBeast. And he was on a group Skype with these other four individuals. And they were talking about those exact things you just described, right? Because I love it.

Yeah. I love it. And I think that... I mean, if I think about where I started my career, I started my career—and it's so funny that you clocked. I don't know if you looked into what I did for a living, but I was in, when I first started, like, B2B enterprise SaaS sales and just sales in general. And, you know, you finish work and, like, I, I didn't feel like researching better enterprise sales techniques. Yeah, but that's that. Yeah, but I, I suspect there are some people that do. I'm sure they do. I'm sure they do. I'm sure they do. And it's a useful skill. You can make a lot of money doing that, too. But, but, but that's, that's why this is the test I love. And yeah, there's a, there's a, um...

Clip you can go watch on YouTube of a graduation talk that Seinfeld gave at Duke, and he, he uses the word 'fascination' where you use 'obsession.' And I, I think curiosity, fascination, obsession, all those things get back to this point: would you spend your free time learning about, more about it? Yeah. And there, you know, that's a high test. That's a high bar. But I certainly did that in my field.

Well, I was going to ask you, so when was your pivot into venture capital? Because there was a question that Frank Quattrone asked you about your dream job. And he basically asked, like, what was it? And then you answered, 'I've always dreamed of being a venture capitalist.' And then Frank said he'd make it happen. Then within 13 months, you were a VC. So... what was, what was that interaction? What did that sort of trigger?

Let me give you some context. Yeah. So I was, I was in my third year as a sell-side analyst in New York. And Frank Quattrone, who's a very famous investment banker in the high-tech world, left Morgan Stanley and was starting a new investment bank. I knew I didn't want to be a sell-side analyst anymore. I had been approached to be a buy-side investor at a really great firm called Capital Group and was interviewing there. And I got this call out of the blue from Frank. And I talked to someone who knew him well, and he says, 'You have to take the meeting.' This other individual said, 'You have to take the meeting.' So I took the meeting. And he asked that question. He said, 'What's your dream job?' And I said, 'Well, I've always dreamt of being a venture capitalist.'

You know, and that goes back to—I worked at Compaq, which was venture-backed. As I studied economics, companies on Wall Street, I could see the young, up-and-coming disruptions. Interesting to me. I like—I've always been fascinated with gambling and edge and those notions. And so I was going to go on the buy-side, but that's what I wanted. And he said, 'Come work for me,' 'cause I told him I didn't want to do the job he wanted to hire me for. And he said, 'Come work for me and I'll introduce you to every venture capitalist I know,' which was a very fortunate moment. And, uh, that word fortune comes up a lot when you study great people. Um, but I do believe that, uh, what's the famous saying that's, uh, 'where preparation meets opportunity'? Yeah, I mean, like, you get these chances in life, but you got to take them. Yes, you got to be—you, you have to be—you have to be able to even recognize them.

It is funny. Someone sent me something the other day. This is so far away from everything. But there's an up-and-coming country singer named Charley Crockett who's starting to really bubble up. And apparently, he was outside of Gruene Hall in New Braunfels and handed—handing out his own CD, and handed one to Evan Felker of the Turnpike Troubadours. And that led to him starting to get tour dates and stuff. And people go, 'Wow, that's super fortunate.' And I'm like, 'You know what? Most people aren't handing out CDs at Gruene Hall.'

No, you got to, to a degree, you got to make your own luck in life. Like, you do got to make your own luck in life. And that's like—this is, listen, if it's career, if it's entrepreneurship, it's like if you take enough shots and if you take enough action, I, I think you do start to actually create your own luck. Just through, like, pure volume of things done, something's going to work out in your favor. I think that the people that are, again, in the majority of being unfulfilled in their career and saying, 'I would start over if I could,' it's because for a period of time, for like 5, 10, 15 years, they haven't really taken any ambitious shots that could lead to the result they want.

Listen to this. This is also from Rick Rubin's book, which, if you haven't read it, it's very different.

Well, Rick Rubin's a really interesting guy.

But he said, 'To the best of my ability, I've followed my intuition to make career turns and been recommended against doing so every time.' It's funny. Every time. And I just think that's fascinating, right? Like, this trusting your inner self, like, voice and what it's telling you versus what society or these well-intended—once again, well-intended—chaperones.

That's the thing. It's always well-intended or well-intentioned, but it's because they are speaking from their frame or their perspective. So if you had somebody in your circle, if you were speaking to Rick Rubin about career change, Rick Rubin's going to tell you, 'Go take the career change. Go do the crazy thing.'

He unquestionably will. And that book, you know, it's targeted at more creative individuals. It's funny. I reread it, you know, thinking about my book. My book's more targeted at professional career, you know, type things. And he's more focused on creative individuals. But he's unquestionably urging people to have more permission, to take more risks, to be more of themselves.

But the majority, again, have never done that. So they're speaking to you and they're giving advice from their reference point. Fair enough. But that's the issue. So if your parents say, 'Well, maybe don't switch careers. You just got this new job,' they mean well. They want safety and security, but...

There's this also famous video you can find on the internet where Jeff Bezos talks about his career regret minimization framework. Have you heard of this? And you can go watch it. It's like five minutes. It's not long. But when he was thinking about starting Amazon—and this is exactly what we're talking about, like a hard pivot—he is working at D. E. Shaw. David Shaw does not want him to leave. He's young, highly successful. He's walking away from a career most people would dream of having, right? Walking away. And he said he went and walked around Central Park and he asked himself the question, you know, 'If I'm 80 and looking back, am I going to be more upset that I left D. E. Shaw or that I didn't try this thing that was tugging, you know, on my ear telling me, "You got to go do this thing"?'

And he said that made it simple. Like, in his mind, it was abundantly clear. And Daniel Pink has a book on regret. And he says that there's tons of academic studies that boldness regrets are the ones that weigh on people the most. And boldness regrets are the things you didn't do. Like, in over your life, you get to the end and, 'Boy, I wish I had done this. I wish I had asked this girl out. I wish I had changed careers. I wish I had done this thing.' And life is a use-it-or-lose-it proposition. You go through once. And so having that mindset from these other great individuals, like, I think that can help with that question you asked a while ago about how do you get off the snide? How do you get out of this thing if you know you don't like it?

So you studied a few different success stories. So Bob Dylan, you mentioned MrBeast, Bobby Knight, Jen Atkin. And you are a master of pattern recognition. So explain to me why you were studying these people in the first place. So how does studying MrBeast...

sort of play into having—well, some of the stories were the inspiration for the book, and some of them were to fill out the book and, and, and make it even better. And so some of them we went looking for after the fact, and some of them fell upon me. You noticed things when you started? Yes. Yeah, the ones that fell upon me were from reading biographies. And it's so funny. When I was—I had a horrible verbal SAT score. I never read. And then somehow when I got to graduate school, to my MBA program, I just started reading. And I don't know why the bit flipped. Maybe I had free time while I was there and I started consuming. And I have a list of books at the back of the book of all these books I consume.

But like, you know, a lot of the people that I studied, you know, along the way picked up a lot of the, you know, personal development books, Seven Habits of Highly Effective People, you know, uh, the Dale Carnegie book. Like, you know, Warren Buffett says the Dale Carnegie book had more influence on them than anything. And so I think right after those type books or Tony Robbins, you know, you start to fall into the, the, the biographies. And, um, they're fun. Like, you learn a lot of things reading about these other successful people and what they've done. So that's why I, that's why I got into... Then we, we started looking for stories of people who, um, made an intentional choice to, to take a career change, you know, who, who had this aha moment, "I'm gonna go do this," and set about it intentionally, um, because that's the type of

framework that can be helpful to someone that wants to go do this.

And what was it, what was the thing that, that you noticed in these people? Like, you—I mean, like, that's why I was, I mentioned pattern recognition because you, you did this for, you know, 25-plus years looking at founders. So, like, one skill is easily transferable. I know this for sure. So, if you notice what makes a successful founder, then you start to notice what just makes a successful person. And we sort of touched on a few different points and attributes and personality traits and whatnot. But when you study the most successful people in the world, the most successful people that have made career pivots, what are some of the patterns that you start to recognize?

So first of all, you have to know that you're going to, you have to have this intentionality. You have to know that this is something I'm excited about and determined to go do. you know um danny meyer when he um he walked away from a sales job this company that sold these devices that hook into clothes so that you can't steal them from stores he was making over 200 000 a year and this was 40 years ago and so that's a lot that's a good salary for a young person And he took a job that was less than one-tenth that salary in a restaurant to start the learning process. And so like the level of determination you need is ultra high. But then he set about a learning journey. So he enrolled in a restaurant management class.

He enrolled in a sommelier class. He worked at this restaurant for almost nothing to get exposure. And then he went to Europe and worked for free. He set up a series of sessions where he could learn at different restaurants. And so this learning part, um, is something that I see over and over and over again, and I would divide it into two components that are critical. Um, the, the first one is learning the history. And by the way, I think this is a piece of advice that could help anybody that's trying to get hired for any job. Most people—there are a few fields, like, like American literature, where you study, it's like, can you—you have to study the greats. But in most fields, people don't. There's no one going into an accounting job that studied the great early accountants. But if you went into an interview and there's 20 candidates, and it's quite clear you know the history, you're going to be highly differentiated.

So it immediately helps with peers and mentors and all these other things if you know that history. And if it's too boring for you to go read the history, you failed test one, you go back to start, right? And find something else. There's this thing we uncovered that we put in the book. There's this big chess tournament, global chess tournament. And during one of the middle of it, they did something for fun. They did a trivia contest in the middle of it for the history of chess. And Magnus Carlsen won, of course he did. He's obsessed with it. See, but you say that, "Of course he did," right? And, um, here's another, like, insane thing. I, I, um, a friend of mine won at a charity auction dinner with John Lasseter at his house, who's the creative genius behind Pixar, and

When we showed up, they put us in his screening room and served a 10-course meal to 10 of his favorite cartoons of his life. And he walked through and described why they mattered to him and how they impacted him. And most of them were from 40 years ago. And you sit there and you say, holy shit. The guy that's innovating on top of his field has this kind of understanding of the history of the field. So that's one. The other edge where you can highly differentiate yourself is what's brand new. So a lot of people go into careers... You go into work in a marketing organization. You go into work at a finance organization. Most of those people don't know how social media works, how podcasts work. And if you're in those orgs and have that knowledge of what's on the edge, you're once again highly differentiated.

So I love learning on both sides. Like, where's innovation in this area? And understanding all of the, you know, history like of the field. Like, we we talk about a picture in the book, um, that, uh, Picasso did when he was 14. If you go to the museum in Barcelona, you're shocked, or I was shocked to find out that Picasso had nailed perfect realism by like 13 or 14. He was winning awards for how amazing his pictures were. And so you can go find, we included a description of one called The Altar,

But, but everyone thinks about this Cubist and all this thing, and, "Oh, anyone could do that." But it came from a place of, of fully understanding the art form first. It was, it was this fascination, this—well, Seinfeld calls it fascination, I was calling it obsession, or whatever you call it. But because I think that when you look at somebody like a Picasso, you'd say, "Well, he's a, he's a savant. He's like naturally, he's naturally gifted or talented." I think that that actually just is almost like a compass. Maybe that first little bit of talent or gift points you in a direction, but then the obsession, to use what I call it, it's what actually allows you to be successful at that thing. I mean, if you look at any great—I mean, it could be Picasso, it could be LeBron or MJ—pick a great from any field, any industry.

I mean, even founders that I speak with, and I'm sure that you recognize this as well, they know so much about what they do. It's disgusting, the amount of knowledge they know, useless knowledge that they sometimes know about what they do for a living, right? They just know to the intricate detail.

And by the way, look at the tools we have today to get knowledgeable. It's never been easier. I mean, I started writing this before LLMs took off. Like, you can just sit there and talk to OpenAI. You want to learn about the history of a field?

You could spend the next two days talking to OpenAI and know more than most. There's no excuse to not have this bedrock level of information because it's never been easier to get.

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I'm curious because obviously you've been like incredibly successful at your quote-unquote career, your, your job. Um, so when you look at some of the sort of the things that the most successful people in the world have done with their pivot and their career, have you mirrored that in your career? Like when you first started in VC, did you like study the greats? Did you go down rabbit holes? Did you learn the history? Were you just like obsessed with this thing more than anybody else?

I think it was a little broader than VC. I think when I got into finance and investing, you know, I did that. So I read all the Buffett letters. You know, I read, you know, Howard Marks. I mean, his stuff's fascinating. I read all I possibly could. Yes. So I think if someone said, you know, compared to other venture capitalists who knows more about investing history, I think I might be at the top of the list among venture capitalists. I don't think most of them... And a lot of people that roll into it new almost never understand investing. They don't study investing. So yeah, I do. As a nod to all the people that wanted this book to be about me, in the epilogue, I do kind of walk through my story in the lens of the book.

So that's in there also. I'm curious why people don't find value in history. It's almost like they think that it's like an ego thing, or they think they're smarter than they are.

I mean, you've obviously hung out with a lot of founders. I think in the tech community, founders' view—they've been taught that old companies are stodgy and bureaucratic and stupid, and I think they put all of history into that, into that world, which is unfortunate. I understand why. Like, once again, it's not somewhere like, you know, and there is, uh, there is an element of rebelliousness that allows a founder to be successful, and that mindset can cause you to question everything that's been done historically, every group, which is, which is a benefit, like, like saying, saying like...

Okay, we're not going to do things the way they've always been done. That's what allows some people to be successful. But I was listening to your interview with Tim Ferriss, where you were talking about how a lot of founders could actually benefit from an MBA. And I think it's the same mindset, like whether or not you study the history of company and organization, or you study sort of like... you know, a more formal business education. I think there is value in understanding history, but maybe that's not what you replicate. You just learn from it.

Well, like I said earlier, like having understanding the bedrock, I think gives you a full understanding mental model for knowing where you now want to innovate on top of what's been done prior. And I think the Picasso example's that way. You know, one of the things, the big unlocks on the Dylan story that, like, if you watch the movie, you don't see. When he was in Minnesota, he probably listened to more folk albums and studied more folk artists than anyone in Minnesota. I'd have to believe that when he left to go find Woody Guthrie, he knew more. He just knew more. And when they talked to people back then in that neighborhood, they'd be like, 'Where'd that record go? Oh, Bob took it.' He was just gathering.

Back then, the record stores had these listening rooms if you couldn't afford the record. He's just sitting in there listening to over and over and over again. And people don't think about that element of any musician, like how much did they study the past, you know?

When you do make a pivot in your life, in your career, what allows you to be successful?

Well, you brought up earlier, like, this is harder if you're older. We have a chapter near the end of the book called "Never Too Late" where we profile several people that made post-40 changes and drastically impacted the world, which is kind of fun to know that it's still possible. You know, I don't know that the techniques are any different. I think the amount of gumption that's required is so much higher and harder. Um, society, you know, doesn't—I don't think—I think for, for whatever reason, that thinks that we've evolved to a place in society where if you're 40 and have three children, you don't leave your job and go chase a dream. Like, it's just—it looks reckless, right? I think that's sad, though. I think it's sad because I think that that's actually—

—when you have, like, the life experience where you actually could have a higher success rate than somebody who's just like a, you know, the Stanford dropout, the, the, you know, the typical entrepreneur. I think that if you are having like, I think, I think, and I mean, like you work with people that are probably on average, like if you look at the companies you've invested in, they are sort of like the more typical entrepreneur, right? It's sort of like the Hollywood version of entrepreneurship. But think about somebody who's 45, who's worked in a career or a business their whole life. They recognize the gaps in that industry better than anybody else. They have, like, the lived experience, the business acumen, and then they can either strategically pivot their career.

They can go build something in that industry at 45. Like, I feel like their success rate is much higher. Yeah. I don't know. I don't know. I'm just making these, I'm making these assumptions up, but I feel like, just intuitively, this person, I would assume that they would have a higher likelihood of success because of what they've gone through in life and what they know.

The reason I'm smiling as you say that is I have a lot of ambitions for the book. It's obviously more targeted at young adults, and as we talked about, the people that serve in mentor roles for that group. But I would be thrilled... I would be tickled pink as the book launches if I start to get inbound stories from people who, just like you described, who this book gives them that permission. My co-writer uses the phrase 'disinhibiting.' And we found stories like Seinfeld. Decided he loved stand-up and wanted to give it a try, but it wasn't till he read this book—someone wrote a book about 20 successful stand-up comedians, and here they are, and here's their profile, and they all make money, and like, that book gave him this disinhibiting moment: 'Oh, you can act—one can do this, right? One can go do this.' And I, I hope, I hope, I hope I hear from a ton of the people you just described, and...

And I hope they go on to do really amazing things.

When you look at all the people, even like the... the founders that you work with? Because outside of this study, you work with founders on a day-to-day. Do you find that people that are more entrepreneurial are more in love with the work they do? Even if they're not—say they're not like founders by name. Say they're people that work within, like, an early-stage startup and they built from scratch. Do you feel like they're a little bit more in love? They're thriving more often than not in their career? Like, is there...

...anything else that sort of is a good signal for— I would, I would say this, because you're making me smile once again: like, there are more smiles in a startup than I've ever seen in a non-startup. And in that, you're coming up with all these theories, like, in the—in an unknown world, like, you're, 'Well, what if we did this?' or 'What if we did this?' or 'What if we did this product or changed this pricing?' And when something works—when, and many of those theories don't, like, maybe it's one in five, one in 10, or whatever, but they keep tilting at it—but when it does work, there's this massive smile. I mean, I can just look at—I see founders in my brain, like, they want to call you and tell you, 'Guess what?'

'Guess what we just, like, you know, what happened? Like, just came.' So yeah, I do. I do think that, like, I do think they're constantly, um,

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Thrilled when something comes together.

That being said, I'm trying to really unlock why people have so much regret. It's not just one thing that leads to regret. It could be that the job you're working in was something that you just thought you had to do. It could be, and you've just been doing it for forever. But I think it's also because you feel like you stopped winning in your career. Like you stopped doing anything interesting. You stopped taking chances. You stopped taking any kind of risk. You stopped growing. You stopped achieving anything as an individual or even as a team. And you're just in... You know, you're just in this routine, this comfort zone routine that you've been doing for X amount of years, and there's no newness. Like, at least in a startup environment, there's super high risk, but a lot of newness all the time.

And I think that that can also create a lot of career satisfaction.

So, how do you, like—I mean, like, the question, I think that's a great point that you're making. And look, I, I do want to acknowledge there are many people in this life that have decided that their career is their career and their fulfillment is outside their career, and they view one as a means to an end, and they don't want to hear about it, and this book's not for them. Like, I'm not judging them. This book's not for them. If you are in that situation you just talked about and feel frustrated, you know, pick up the book. Like, this is who I want to speak to and talk to. Do you have any career regret? No, but I don't because I fell into that spot. Had I not fallen into that spot, yeah, I might. But I don't.

And by the way, one thing I harp on in the book, those two jobs that I had for three years each, I don't regret those. They were part of the path. They got me where I was going. And I'm glad that I had both of those stops along the way.

I feel like, um, I, I feel like people always think they have more time than they actually do. I don't know. I've noticed since—I've noticed, I actually noticed even more since, since, since COVID. I don't know why, but I just feel like time flies now. Like, I feel like—I think it's because you're getting older. I think time moves slow when you're young. Yeah. And it gets faster when you're older. But like, years are flying by. Yeah, years are flying. I have this theory that it relates to your storage capacity and your brain.

When you're young, you get to store everything. So everything feels slow, but your brain fills up and then you're not storing much new. No, no, it's true.

Well, I think that I've actually read—I can't remember where I read this—but there's this idea, a few different ideas as to why time moves faster when you're older. But one of them is you don't experience as many new things, kind of like what you're speaking of. You don't experience as many new things. There's not as much newness. Yes. So routine—like, life is routine. You do the same things day in, day out, day in, day out. And if you actually took time to do something new every single day, time would feel like it's moving slowly.

And by the way, that ties really nicely back to this thing I said, where if you're chasing your dream job, you learn at night as an alternative to entertainment. And so the newness kind of comes with it. You know, I was talking to Danny Meyer recently, and he had just come back from a—yet another European learning trip with books full of notes, like, like you. Yeah. Like, who goes on learning trips? What percentage of people in their career go on learning trips?

But this is what differentiates you. No doubt. This is what differentiates you. I think you have a Satya Nadella quote in the book: "I buy more books than I can finish. I sign up for more online courses than I can complete. I fundamentally believe that if you are not learning new things, you stop being great. You stop doing great and useful things." I mean, whether or not it's learning through reading, learning through podcasts, learning through exposure of just trying something—it doesn't work out, it failed, you learned the lesson, you try something else. There's not a single person who I know who's successful, happy, and fulfilled who is not constantly exploring new ideas. And there's no—like, I mean, up until the point, you know, when you are no longer on this earth.

Like, there's—you are always, always learning new information.

Turnaround at Microsoft may be a unit of one.

Like, it may be the most successful business turnaround ever from—

I don't think many people know that story.

Yeah. And he, in that, when he was talking about that, someone asked him how he led so much change there. He intentionally took that mindset and said, "This is going to be the mindset of the org." Yeah. "And, you know, are you in or out? Like, are you going to become a self-learner and be a part of the new Microsoft? And if not, you know, this probably isn't a place for you." And that's really cool and innovative and new.

First of all, hats off to him for accomplishing this. I feel like a lot of CEOs wish they could do that with their companies. It's not easy, though. No, it's not easy because it pushes people outside your comfort zone. Yes. No doubt. To become a self-taught individual. Because then you start to realize—I think this is probably the scariest part. When somebody is not happy with their work—and I love the idea of agency and of internal locus of control and of taking responsibility for your own outcomes—but you start to realize that, "Oh, I'm not in a job I love. It is entirely my fault that I'm still in this job." And our fault or responsibility or whatever word you want to call it. And then the responsibility becomes yours to learn the skill or to do the thing or to make the move or to take the action.

So then it becomes quite scary because you realize that whatever you actually want to achieve is on the other side of your action and your agency. And I think that puts a lot of people in an uncomfortable position if they are not used to adopting that mindset and that mental model. Whereas, I think, a good founder or even, you know, forget founder, a successful executive that has worked his or her way up through the corporate ladder, they understand that most of their success has been contingent on them and they are personally responsible for all outcomes, good and bad. And I think it's a very scary idea for people to adopt.

Well, I think the book can be super helpful for people that feel that way. So the structure of the book, I think, is somewhat unique. We divide it in half between what I call profiles, which are stories of success, and principles, which are tools or methods of success. And, you know, in addition to giving people permission, I want them to read about other people doing this so that they feel the possibility. And I think the stories will really help on that front, and then give you very straightforward tools and processes to go about the journey. Once again, these aren't really mine. I've studied other people that have been wildly successful. I see some mirrors in my own success, but I've brought them together and synthesized them in a way that I think could give someone like you just described confidence to take the leap and to have some conviction that they'll be successful as they go forward.

One last idea that I think is really important, and not to throw AI into every single conversation I have, but you mentioned that AI is about to eliminate some of, sort of, the more safe careers. So this conversation, this book, some of these ideas, you know, the need for somebody to take action in their own life is probably becoming a little bit more relevant now than it even was five years ago. Because if it's not just, you know, we're looking at it from the angle of you are doing it for fulfillment and you're doing it so that you love your life and there's no regret. But, like, if you look at it from the other angle of maybe the job that you have right now is not around in five years, or maybe it's downsized, or the people that are doing your job are specialists in AI and they can 10x the efficiency of every single person in that business unit.

Because they know how to use LLMs and different, sort of, AI tools and generative chat tools or whatever. If you don't learn new shit, if you don't find a way to move into a career you love, or if you don't find a way to become even significantly better and more proficient and forward-looking in the career that you're doing right now, at some point you're going to get replaced, which is just a hard truth, whether or not you love it or not. It's—it's just the truth. So I think that the mindset of learning new shit, understanding that that can either be applied to make you, uh, more probably, like, secure your career in the job that you're doing right now and/or set you up for a potential successful pivot.

If you're just, like, again, a self-taught person, I think that idea is one of the most important.

Yeah. And I, I would, I'd say three things to that one. If you are in a dream, if you're in your dream job already embrace AI. You want to become the superhuman. That is what's new on the edge. You should be self-learning. That's what you should go do if you're in your dream job. If you're not in your dream job and it's threatened by AI, yes, all the more urgency to jump out. And then lastly, I would just say, I think those well-intentioned parents and coaches send people towards the safe jobs because they think that if you make enough money, you'll be happy in life. There's all kind of... of surveys that show that not to be true, that fulfillment matters way more than wealth. And so I didn't think it was right.

But now that all those jobs are in question, hopefully some of these people will stop cramming kids in, you know, down these, down these conveyor belts towards Comp Sci or, or whatever, because, because now it's not as certain. No, now nothing's, now nothing is certain, right? So the only, the only, the only thing that's certain is you have to be somebody who's adaptable, who is a self-taught individual. If, if you have those skill sets and that mindset, I think then your career—and you're much more likely to have that mindset if you have found something where you, that you're highly curious about. There's, I stumbled upon this podcast with Angela Duckworth, who has obviously written this famous book, Grit. And she took some time to talk with us as we were writing this.

And her book said there's two things that lead to success: passion and perseverance. And that's what Grit is all about. And she says if she were rewriting the book today, she'd focus way more on the passion side. Because what she discovered is we've taught a lot of these kids how to grind, right? You know, just like you teach a kid how to practice piano for four hours a day. And what ends up happening is, you know, you crush your SATs, you get into the best school possible, you get one degree, maybe two, but you run out of steam if you don't have this passion that drives this curiosity.

You've been trained to run, but eventually you just run out of energy. You mentioned something interesting, and I just want to touch on that. You shouldn't be racing towards money. You should be racing towards fulfillment. How do you measure fulfillment? How do you know if you are truly fulfilled? Is it a feeling? When you look at some of the people you've interviewed, what's the metric?

I have to believe that there are other academics or authors who have written books specifically on that topic. I'm going to go talk to ChatGPT after this so I can have a better answer. You know, I really have found that people that have this self-learning element to their job are the ones that are fulfilled. And I don't know if it's for the reason you said, where there's just constant newness in their life. I think all the people we—I mentioned this earlier, but all the people we profile end up touching a lot of other people's lives in a positive way. If you become extraordinary in your field, and at least if you're following the principles I talk about, you're co-evolving with your peers, you're, you know, these kind of things, you're building relationships, you're having success, you're impacting people's lives.

I think those are, you know, the elements of fulfillment that matter the most.

So Running Down a Dream, that'll be available wherever you get your books, and we'll put links in the show notes and everything like that. Where do you want to send people? Is there any other socials or websites that you want people to go to?

There's one thing I'll mention, and we're just putting it up right now, but I'm going to take all the proceeds that I would get from the book and more and launch a foundation called Running Down a Dream. And we're going to take applications for micro-grants for people that are kind of stuck financially that want to go chase their dreams. And, you know, we'll take those applications in and I'll create a committee and make some choices. And we're going to hand out some grants to see if, you know, because some people came to me and say, 'Well, what if someone just is too stuck financially?'

Which is valid.

Which is valid. So hopefully we can do that. And hopefully some of those people will be successful. And then we'll tell those stories.

I love that. When someone's finished reading, what's the first thing you want them to do?

There's two things that have already happened in the handful of people that read the book. One is they immediately want three or four copies because they have in their mind someone they want to read this. So I think they know of... a kid that's got too much pressure or hasn't really, isn't happy, or feels like maybe they started down the wrong major, or, you know, they, they know someone they want to hand it to. That, that's... I'm very, um, optimistic about the fact that the book may have a viral loop built into it already from that, um. And then the second one I've heard is like, you can't, you can't get away from it, whatever, it's good. You know, I've even had like a 60-year-old wrote us and said, 'Shit, I thought I was retired. I... there's something I need to go do,' which is fun, like, fun because that's... I'll finish where we started, like, unlocking human potential. Like, if I can get, I mean, if I could get 100 people to go be extraordinary that, that were otherwise not going to be, I'd feel like this was a huge success. Hopefully, it can be way more than that.