Bill Gurley: Running Down a Dream | Episode 23

Welcome to Impossible Dreams, Bill Gurley. Thanks for being here. Thanks for having me on. I sort of appreciated, in watching your talk that you gave—it was at Texas a couple of years ago?

Yes, it was at the grad school MBA program at Texas about eight years ago.

And that's where you did your MBA? Yeah.

Yes.

Yeah. And watching that talk, which, you know, did you know at the time it was going to be a book? No. Because it's clearly like, 'Wow, you know, that's a blueprint for a book.'

Yeah, I didn't. I mean, my day job was a venture capitalist, so it's not something that I—the topic wasn't, you know, core to what I did. In fact, one of the reasons—during my venture capital career, I blogged quite a bit, and so it was very common for me to scratch down ideas, trying to figure out where the world was going from a technology company perspective. And then I would build these theses and write them down. And I had done that in this case when I was reading these biographies, but it didn't really have a place in the venture world. And so when I had a chance to give the talk, I did. And then they put it on YouTube, oddly, and a few people noticed, including James Clear. And a few...

After it had kind of been out there for a while, people like James started poking me with the idea of a book, but at the time I gave the talk, it wasn't on my mind.

That's so interesting. I mean, uh, the idea that you at that point had spent, you know, your career from—and, you know, correct me if I'm wrong on any of this—from being an engineer, then a top research analyst, to one of the world's most successful venture capitalists, those MBA students get to hear from one of the best, right? And within that becomes the seed for something that you're super passionate about now, which is like, 'All right, well, what is life after venture capitalism? And how do you give back in the way that so many of the people that you talk about in the book, the Bobby Knights and, you know, Danny Meyer?' And that's sort of part of this, how you thrive is sharing, right?

And, you know, nobody's Impossible Dream when they're a kid seems to be what they end up... There's very few people who are like, 'Oh, I knew at six, seven years old.' Did six-year-old Bill Gurley know he wanted to be a venture capitalist? No, no.

I worked with a co-writer and researcher, and it probably took us five years to turn the presentation into a book. Because we went and did a lot more work and we probably combed through hundreds of biographies. And there are a few. There's this great anecdote that I don't know if you've ever heard of Steve Harvey, the comedian who's on Family Feud now. So Steve Harvey in his chat with Oprah on Masterclass tells a story about when he was 18. Seven years old, his teacher had an exercise and asked what he wanted to be when he grew up. And he went last and all the other kids had gone and he had written on a sheet of paper, I want to be on TV. And the teacher thought he was making fun, like that he wasn't taking the assignment seriously and yelled at him and sent him home.

And when he got home, his mom yelled at him and sent him to his room. And he's sitting there in his room and, you know, wondering, 'What? All these adults, you know, they told me to say...' And his dad comes home, and his dad asks what happened, listens to the whole story, and says, 'Do you have the sheet of paper?' And he pulls it out, and he goes, 'Let's put this in the drawer by your bedside, and I want you to look at it every day.' And so his dad gave him that permission. And your question was, 'Do most people end up there?' And I don't think they do. I think that our society has decided that... And I think it's very well-intentioned. I always want to say that because I don't think... I don't think anyone's out to stifle creativity per se, but they worry.

They worry about the kids' economic well-being. They worry about their ability to have a family and put food on the table. And they push people towards safer jobs. And they tend to steer away from the incredible life that you've had and those kind of things. I was going to ask you, on your Wikipedia page, it says you took the MCAT test. I want to understand why, because it relates to this question, I suspect.

Yeah, it totally does. When I look back, when I was a kid, I was doing theater. I have no memory of doing theater consciously until I did my first play when I was 12 or 13. And then in high school, I started doing musicals. But it was never like, "I'm going to do this for a living." It was like, "Oh, this is fun." And even in college, I went to Duke to be a doctor. So I took the MCAT there because it was there where you're finally a young adult and you're like, "Wait a minute, maybe I'd—maybe I don't want to do that. And maybe I can go and roll the dice and take a chance." Of course, being like, you know, an overachieving Type A guy, it was like, "Well, we got to have a backup plan." And we got, you know, there was no like—there was no what I'm advising my kids now.

You know, it is a fascinating world because I woke up this morning knowing that I was going to be talking to you. And I thought, you know, so many keys in your book are about who, by the way, your story reminded me, my younger son, who's 14 now and, and six, three and an elite basketball player. Both of my kids are basketball players. I have no idea where they get that from, but we can talk hoops, you know, I know you're, you know, former big time Hooper, but my son, when they did that, where they pass the mic around to the kids in, you know, kindergarten, first grade, and it's the cutest thing and the parents are all there. My son said I want to be in the NBA. And the kid next to him said I want to be a trillionaire, which kind of stole the attention because it was like,

does that kid know what that—like, you're six years old and you know what a trillionaire—like, but my son said, "NBA." And I went, "Oh yeah, right. That's so cute." And now here we are. It's like, "Wait." So I wonder what our souls know, what our souls come here to do that, like you said, maybe society, parenting, sort of steers us towards those safe things.

I don't know if you can take yourself back to being in high school and then at Duke, but what part of you was telling you MCAT, medical school, and why, and what finally allowed you to relax that constraint and pursue the thing you love?

I think in my case, I loved them both. I think it started very ego-driven on the medical front. My mom's brother, my uncle, was a doctor, and he was the most successful guy in the family. And I saw my dad and my grandfather in construction, very, very successful, but busting their ass. And I thought, you know, my uncle's got a beach house, and he's got a place in Aruba, and he's like, "Maybe this guy knows something." And so I really thought, "All right, I'm going to go to Duke." I pushed all my passions to the side. I was like, "I don't have time to do theater." And what finally reopened the door: an acting teacher, Jeff Storer—I love to give my teachers all the credit in the world—gave, uh, came to a voice recital and said, "Listen, um, I want to cast you as the lead in Carousel. We're doing this big university-wide production, we're spending a lot of money on it." And wouldn't you know, Bill, Carousel was my favorite musical, and I was like, "I think I have to do this." And I did it, and he said, "Look, I think you should do this for a living."

And I was like, "What, are you crazy?" He said, "No, go get a professional internship over the summer and see if you got what it takes." And I did. I made 30 bucks a week cleaning Equity housing, being in the chorus of some shows up in Maine. But the leads would come from Broadway. And I compared myself to them and went, "If I got some training, I could do this." And then I went, "Why don't I take two years? The MCATs are good for three. So I'll take two years and go to a grad school, if I can find a grad school that's only two years." Juilliard was longer. Yale was longer. And I found the Cincinnati Conservatory of Music for musical theater. And I thought, "There's no way they're taking me. I don't know what I'm doing."

I walked onto that campus and these kids were dancing and singing and acting. And I was like, "I'm never getting in here." And I got in, but I also did well on the MCAT. And I was like, "I got a real choice to make." And so I was like, "Well, MCATs are good for three years. So I got two years to go to med school—I mean, two years to go to grad school for theater. And if not, you know, I'll make my parents happy." And, you know, here we are.

Pretty amazing.

Yeah. Yeah. I mean, what—what happened with you when you were—you were a basketball player at Florida, right?

Yeah, I—I wasn't—I was—I was a basketball practicer at Florida. I didn't get on the court much. So I had no—I had no chance of that being a livelihood. But I was a computer scientist for a couple of years, practicing computer, realized that wasn't something I wanted to do for 30 years, went to business school, ended up on Wall Street, had a lot of fun doing that, but also realized it wasn't what I wanted to do for 30 years. And I made my way into venture capital. So I had two stops before I got to my place.

Yeah, and a very humble way of saying that before you became a VC, didn't you lead the Amazon IPO?

Working with others. Yeah, Frank Quattrone and I, in my last year as a sell-side analyst, we worked on the Amazon IPO together.

All right, so just real quick for people listening who are like me that really have no idea how it is you do what you do: What does it mean to be that sort of lead analyst on that, and then what does it mean to be a VC? Yeah.

Yeah, yeah. So the occupation I had prior to becoming a venture capitalist is a sell-side research analyst. So you write research reports on public companies, and they get published and sent around amongst the investor group. Sell-side just means the person paying for your research is the broker or the investment bank, not the fund that actually makes the calls. And so if you see analysts quoted in the press, most—most of the time, it's a sell-side analyst. And—and back in those days, you know, someone on the banking team would team up with someone on the research team, and you'd compete to be the—the—the bank that shepherds new companies into the public market. So we were a service firm; we were transactional. It wasn't like we hung around forever, but we competed with Goldman and Morgan and won the—the right to—to help Amazon go public. So back in those days—

It was a long time ago. Yeah, it's pretty exciting. I mean, did you ever think they'd be what they are?

Not at the time. I mean, I knew Jeff was very special. And part of that experience that's probably most—most useful to me is Jeff and I developed a relationship that still exists today. He's quoted on the back of the book. He was kind enough to give me a blurb. And so, yeah. But no, I think it'd be impossible to project that amount of greatness. If I did, I would have just put everything I owned into the stock and held it forever. We wouldn't be talking today. That's right, man.

We'd be talking with you on some private Caribbean island somewhere.

Wait, so. And then you asked what a venture capitalist does. Yeah, yeah, yeah. Yeah. Venture capitalists get to invest on behalf of other people's money. So you have conversations with investors. These companies that are called LPs, limited partners, they provided us capital. We would invest it in small private companies and then hopefully they become wildly successful. The Duke Foundation was an LP at Benchmark as an example. So was UNC, though. So equal opportunity. But, but yeah, so, so that's what we do for a living. And, and I, I met Mark way back. I met Mark even before I became a VC, believe it or not. Cool. And yeah, so you, if you, if you're fortunate, you know, a few of those grow to be bigger companies, if you're very fortunate, several of them do.

And, and occasionally there are companies that are, have such outsized returns that they're, you know, really, really, uh, incredible returns for, for you and your investors. And you've done that multiple times, right? I mean, Zillow, the big, big one. Yes, yes, yeah. Uber. Uber's even bigger than the others, but yes, I had several that have gone on and gone public. And because I invested in the internet marketplaces, a lot of these are companies that people know, like OpenTable and Zillow and Uber.

Can you, just because I'm living vicariously now, can you, can you share, or is there, is there like a memory that you have of, you know, you're a young VC, you've made an investment into, maybe it's Uber, maybe, I don't know. But is there, is there a memory that you have of when one of those, you know, hits? Is it, is it a moment, or is it a slow burn where one of those hits and you go home to your family and you're like, 'Guys, look what... This is pretty cool. Dad's doing some cool things'?

Well, the first part of being a young venture capitalist is mostly, I think, anxiety and fear, because it takes a while to know, because you're investing in a company that might be two people in a PowerPoint, and it's going to take a while before you know if they can be successful.

And you're investing at a very early stage.

Yeah, our firm focuses almost entirely on early stage. And like when we invested in OpenTable, there were three restaurants on the system. Oh, wow. Yeah. And the other thing I was going to say, Aaron, is like a young child lives through their awkward teenage moments, many of these companies have periods where it's easy to be fearful that they may never make it. And so if you start as an early stage venture capitalist, you make like six to 10 investments, they're all reaching that acne stage at the same time.

It's easy to have a lot of doubt. So there's multiple rounds that you guys are funding, right?

We do, but the majority of the return comes from the first round, just because if you're successful, the prices go up. Sure, sure, sure. Yeah. But anyway, it's hard to know. But yeah, eventually, you know, one of them will turn the corner in a way. You know, I remember for OpenTable, I remember when it went profitable. It went profitable pretty early. But when it went profitable, I think we had—and there were some data points that suggested a network effect was in place, which is the more consumers that used it, the easier it was to close restaurants, the more restaurants that were on it, the more consumers wanted to use it. So it got—things got easier once we crossed a critical threshold.

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In the book, did you include...

I know in the talk, you talked about Stitch Fix. Yeah.

I don't know if that made it into the book or not, but are there investments that you go... Actually, I was really drawn to this topic as a passion project, and I resisted the urge to make it about myself for a variety of reasons. That's what felt right to me as... as a creative artist myself, I guess. But the publishers all wanted it, and so I included my story in the back, in the epilogue. But I didn't want it to be a part of the book. It's more of a personal thing.

Well, I can relate to that, right? Because... You know, when I first made the decision, all right, I'm going to find a way to heal myself. The doctors don't have the cure yet. I started to read books. I read 100 books on healing and the nervous system. And you have like 50 books listed in the back of your book, right? Correct. That you recommend and... I thought, you know, Bill's my kind of guy because I put 50 of the 100 books that I read up on my website under the healing section to kind of say to people, listen, these books have been at times my passion and at times my salvation, you know, to help me stay in the energies of this passion and obsession that I have to figure out how to cure myself.

I don't know which book is going to help you, but maybe there's something there. And now you get to add your own book to that for people, which is so cool. What would you say your main hope is for this book?

Well, I'd like to do for as many people as possible what Steve Harvey's dad did for him, what the one professor did for you, the acting teacher did for you to push you in that direction. I think the continuum between safe jobs and creative, passionate jobs has just gone too far to one side. I think the... kind of industrial college complex these days is just set up to push people towards those jobs. And, and there's nothing wrong with, you know, becoming a consultant or a lawyer or a doctor or an accountant. But I, I don't know. And I think even in those fields, there can be the type of people who are fascinated with that subject and dream towards it. But the idea that you should spend the 80,000 hours you're going to spend working on something that you don't have like a deep fascination with, I think is such a mistake.

And even, even for your son, you know, it's really hard to make the NBA. So one in a thousand high school kids plays D1 and one in a thousand of those gets to the NBA. Those are really tough odds. But a lot of the stories in the book involve people that have a passion for things where talent is super important. But they realize that there are so many support jobs around it. So I might not be able to sing or dance as well as Aaron, but I can work in the theater. There are lots of jobs in the theater. And so we have a lot of good stories. Sam Hinkie, you know, from a dead stop reads Michael Lewis's book, Moneyball. Great story. Ten years later, he's GM of the Philadelphia 76ers. My team. Lorrie Bartlett is an agent that we wrote about in the book who grew up loving movies.

She'd see two or three movies a weekend, but never considered herself—you know, having the ability, she wasn't an actress. She didn't think about, didn't have the permission to think about, "I could have a job in Hollywood." And she, you know, got a degree in Poli Sci, was trying to follow in her father's footsteps. And someone told her, "You know, you love movies. Why don't you just..." and exposed her to the notion that there was an agent job. And she'd started at the bottom, you know, telephone assistant and an agency assistant. But because she was so passionate about it, she read every script that they would let her read. And the other agents weren't reading every script. And it started to create a lot of optionality for her.

She ended up on phone calls with people that the other agents weren't calling. And one thing led to another, and she became one of the most successful agents in Hollywood. And I just—I think the reason I say all this, I just really want to give people the permission to chase their dreams. And I have the book divided into two halves, profiles and principles, and they're interleaved. So we have, like, 10 different stories of people that all started on the bottom rung in their field and found their way to success. And then the principles section is the methods to go do it. So I'm not launching you, you know, carefree with some kind of quixotic execution; I'm giving you a framework to really differentiate yourself and, and I think, drive you towards success.

And I'm less hung up on whether it's a traditional field where it's obvious you can make lots of money. In fact, almost all of the stories I chose for the book are in fields your parents might push you away from.

Sure. Yep. So many things to talk about here. First of all, behind me is a statuette of Don Quixote. So there you go, the quixotic pursuit. I mean, but, but for me, there is, there is, there's something in the power of optimism, um, that your book really, I think, I think—I'm not sure if this is, are there six principles that you, I, I, I, I'm going to doubt that one of them is, you know, uh, uh, unwavering idealism, but, but I do think there is a power in, you know, even learned optimism, um, that there's so many people who, in order to sort of either do what they do, whether they love it or not, you gotta find how to overcome the mind's natural bias towards negativity. Most people are just, you know—a positive expectation of a positive outcome is, I think, if you don't have it innate, you better learn it,

if you want to enjoy your life, let alone be successful at what you're good at. Did you find that to be true for, for the folks in the book?

And here's one, one thing that I think really speaks to that. So, there's a story we came across. Jerry Seinfeld was wandering around New York thinking about what his career would be. And he had an inkling that he wanted to be a stand-up comedian. But he didn't know that it was a real thing. He didn't know that you could actually go be successful and have a career. And he found a book called The Last Laugh. I actually have a copy of it over here. And it's... In this book, someone profiled 14 different comedians that were professionals and were succeeding. And just reading through those stories, I think, gave him the confidence and the optimism you're talking about to see himself in that role and to see the possibility.

And one of the principles is about mentorship. And I borrowed an idea from Danny Meyer, the New York restaurateur, when he decided to go be... in the restaurant industry, he made a list of the 10 people he most admired in the industry and studied them. And I think it had a similar impact to what Jerry did with that book. It just gave him the permission to believe it was possible by studying who those people were, how they did it. And I, and you know, in today's world with all these different podcasts and all these interviews on YouTube and the use of AI, that building those profiles of these people that you want, that are kind of—I call them aspirational mentors. But these people that you can see that they did it, they started at the bottom, they succeeded.

I can do it, too. And I think that's one thing that can help drive people towards having the confidence and optimism to succeed, and to believe they can.

Yeah, I couldn't agree more. I mean, that's what this podcast is about. That's why it's called Impossible Dreams. It's conversations with people who are living impossible dreams or helping other people live impossible dreams. You actually have—may have more in common than you realize. And here's how a guy, you know, here's how Bill, uh, did it himself. And here's how Bill's inspiring other people to do it. Because I do think there is that pragmatic, uh, you know, brain that just goes, 'Nah, nah, and the odds this and that.' And it's like, 'Man, you know, Jim Carrey said it best. He's like, "My father failed at, you know, living a life that, you know, at a job he didn't enjoy. Why not fail at something that you love?"'

No doubt. And I think through this process, I've gotten to know both Matthew McConaughey and Rick Rubin, which I would have never thought I'd get to meet. But I think both Matthew's book, Greenlights, and Rick's The Creative Act, they're both saying the same thing you just said, and Jim Carrey said. They're just saying, 'Hey, man, like, you never know until you try. Let's go give this a shot.' And, and, you know, I think I, I, with, with the book, I hope to take that even a step further and say, 'And here's, if you do all these things, your odds are going to go up even higher.' So, so that it's not, once again, a quixotic, you know, tilt.

Yeah, it can be a very well-thought-out tilt against this thing you love. Can you walk us through the other five principles? You said mentorship is one.

Yeah. So, so, and then I, in addition to this aspirational mentorship concept, I go into detail about how to really be pragmatic about mentorship, because a lot of people, especially a lot of young, ambitious people, they overshoot mentorship. They ask Warren Buffett to be their mentor. There's a better way to go about it. So, the first thing is just making sure you understand what it is that you're fascinated by. And not everyone knows. It took three stops for me to figure it out. And I studied all of the best work on how you identify what it is. Some people know. Some people don't know. And we give you a great way to test that. We give you exercises for how to wander with purpose, which is what Angela Duckworth recommends in defining this lane.

The second principle is called Hone Your Craft, and it's about continuous learning. And these two reflect on one another. The best test as to whether you're passionate about something is, do you imagine yourself studying it in your spare time? Like, how does it compete with watching Netflix—like learning about this thing—because the people that are super fascinated, it all feels like free, like they would do it on their own. There's a great quote from Sir Ken Robinson, who is this famous education academic who's got these wonderful TED Talks. But he says, 'If you can light the spark of curiosity in a child, they will learn without any further assistance.' And this element, like all of the people in the book that we profiled, you know, they study the thing they do out of obsession, not—not—it doesn't feel like work.

And you hear that about the best athletes, you know, the best actors. But it's true of people in every field. There is someone in your field who views what they do as an artisan.

Yeah, you give a great example of that with Bob Dylan. I think that's an amazing story. I don't know if it made the book, but...

Yes, it's there. It's there. Yeah, Bob Dylan was much more of a kind of a historic, like this ultra-studious historian than most people would know. And unfortunately, the movie missed that part.

I know. I thought about what I learned from you in context of watching the film. And I wish that that—they did, the Woody Guthrie stuff is definitely there. But that idea that you're talking about becoming really an expert, which actually, before you go into the next principle, I want to push back a second on your own career with regards to this. If you're not the expert analyst that you were—that's you being able to study a company—

Yeah.

Do you think you become the successful VC?

Well, I think—well, yeah. I mean, my journey's a little different in that both of these stops, as an engineer and then as a sell-side analyst—even more so as a sell-side analyst—I did fairly well. I did extremely well, I would say. But for one reason or another, I had this discussion with myself late one night while I was still in the office. And I said, 'Do I want to be doing this 30 years from now?' And the answer was no, despite the success. So, yeah, that was my journey on that front. But when I was doing it, I loved to study public companies and what it is that makes for an undervalued or overvalued stock. I still do that today in my spare time. Cool. Yeah. But—but the venture thing was more of a calling.

And once I got there, I never asked myself that question again.

Cool. Yeah. All right. So let's go into the next principle.

Yeah, yeah. So the third one is titled Embrace Your Peers. And it's probably my favorite. I think that this ultra-competitive path to college and the fact that everyone gets pushed into a lot of sports and whatnot causes a lot of people to have a zero-sum-game mindset. They're like, sharp-elbowed and 'I win, you lose' mindset. And in most fields—and I'm sure this is true in theater, even though I've never worked in it—there's tons of winners. And the people that learn how to create a peer group of people that are along the same journey you're on and share best practices with them, share your network, root for them, have them root for you, have them support you when you're having a bad day, and you do the same thing back—

I have found across all these stories that that becomes a superpower. And I don't think it's intuitive, but I have some amazing stories of people who kind of all rose together.

Yeah, I love that. I think having not heard the final three, but having researched what I think I've heard you talk about them, I would agree with you. This is probably the most important one. It's also one that speaks to your character and how you do business in the world. And it's something I teach my kids, right? Like these boys are in an ultra-competitive environment, whether that be for college or for basketball, you know, playing time. And it's like, I always say to them, 'Guys, there's enough to go around. There's always enough to go around. Don't compare yourself to anybody.' And kids today and everybody today have these phones and screens where you can look up anybody doing anything, and they're all doing it at the highest level possible at ridiculously young age.

We didn't have that, so you didn't have that pressure and that mindset particularly ingrained as young as this generation does.

Yeah, and I think, unfortunately, that can be... that can, that can be, you know, that can, I think, hurt the, the fascination and curiosity part of a child. So, and, and especially like in athletics, they, they, it used to be, you know, you'd be the best tennis player in your county and you'd never, you'd win every match maybe until you went to the state final. These kids today, if you're, if you're exceptional at 10 or 12, they, they, they start ranking you nationally. You've got an Instagram page. Yeah, I've seen these incredible kids that in the day and age I grew up would have probably gone undefeated all season, and their record's 8-8 because they're flying them around the country and making them play the best of the best.

And I can't imagine that's helpful anywhere to developing a lifelong love of a sport, you know, just because there's a point at which you're developing and you don't, you know, you need to feel like you're having fun doing it. And that just doesn't sound fun to me.

No, I'm living that, you know, less so with my older son, but with the younger one, he puts all this pressure on himself to be the best and, you know, as if he's got to get drafted to the NBA tomorrow. And I'm like, I see it take the joy of the, of the game away. And so my job and his mom's job, right, is to take all that pressure off and say, 'Buddy, you're not this, these are not, you're not a businessman at age 14. Yeah, let's take the pressure off. Just find flow, yes, a performance where you love the game.' Yeah. And he'll be, you know, if he goes as far as he, as he dreams that he will, he'll be an interesting player who—he's not playing because he cares about winning a gold trophy. He's playing because he wants to see how good he can get.

And that's always been my thing.

He'll enjoy it. There's an anecdote we have in the book where Kobe Bryant's already won three or four championships. He's had three or four MVPs of the NBA. And that summer, he calls Hakeem Olajuwon and asks if he can fly to Houston to work on in-the-lane footwork. You know, so this is a two-guard, basically, that—that has already achieved more than—than almost everyone in this sport, say maybe four others. And that's what he does in his offseason, like begs a center to teach him how to move in the paint. And so it's that, that I think it shows that the best, once again, the best and the brightest think like artisans and they're working on their craft, you know, and nuance matters, like, and, and, and being studious matters, and it has to come naturally.

It can't feel like work. And I doubt it did. I doubt he felt like he was working that day.

Yeah, that's that's awesome, man. That's super inspiring. Excuse me. What what is principle for?

OK. And so, just I always have to think back through that. So, one was to chase your curiosity, and two was on your craft. Three was mentors. Four was peers. So, we had already got it. But, and five wasn't in the original presentation. We added it, and it's titled "Move to the Epicenter." And for certain industries, there is a place. And in theater, it's New York. Like, it is New York City. Or maybe London. But there is a place in this country where it's very different than anywhere else. And for Silicon Valley—I mean, for high-tech startups, that's Silicon Valley. And I think in the book, I list 10 reasons why you're better off being there than somewhere else. I would shorten it for this and say...

All of the previous principles we talked about get easier in the epicenter. Learning's easier. Mentoring's easier. Peers are easier. They're all around all the time. People, I think, don't do it because they fear it's too much competition. But there's also way more jobs. So, there is more competition, but there's way more jobs. And then there's all these other benefits of learning and mentors and peers. And then the thing that I would just say that puts the real cherry on top is most people in their career have a story that sounds like luck, like there's some super fortunate thing that happened. And the probability of luck goes way up in the epicenter because the chance meeting is just much more likely to happen.

Oh, yeah. And I mean, you tell the Danny Meyer story. I mean, I was living in Madison Square Park, like right off of Madison Square Park, when he opened the first Shake Shack.

And it's such a great example of, like, art if you're a—if you're a restaurant guy. Well, New York got to be the most competitive place in the world. What, are you crazy? But, like, where else can you open 16 restaurants,

Yeah.

you know, and do business? In one day, you can probably visit half, if not more than half of your places, you know, because it's such a compact... environment. I mean, that's the epicenter, right? Yep, absolutely. I love that.

For a songwriter, that would be Nashville, you know? And there's this great documentary on Netflix about songwriters in Nashville that just felt exactly... I just saw so many parallels to Silicon Valley for startups. I might be the only one, but I'm a big music fan, but I'm just sitting there grinning when I hear these people talk, you know, because the—the ability to just on any given night to go to some event or go to some networking seminar, like—and it's probably that way with theater—like, there's just something all the time where you could learn a little bit more if—if you're industrious.

Yep, yep, yep. And I see the guitars in the background.

That's more of me projecting what I'd like to be.

Well, that's your next Impossible Dream, Bill.

There you go. Yeah, so the last one is titled "Always Give Back." And I'm trying to teach, especially young people that are moving from that first rung of the ladder to the second, to have a give-back mentality and kind of consciousness all along the way. And I think a lot of people feel like you're supposed to postpone that to the end of your career, and then you flip a bit and you become gracious. And I think learning to be gracious from the very beginning has, in addition to being the right thing to do, it actually has a bunch of rewards for you along the way. I think you feel better about yourself, you reinforce your mentor-type relationships, you get more people rooting for you.

And so, and it starts with little simple things like you achieve the first step, like maybe for you, you finish your first production on Broadway, send some notes, like to the people, the guy that pushed you into doing it, tell them, you know, 'Hey, I'm doing this thing that we all thought was possible and that you helped me do.' And you send out enough of those letters and throw a little gift in. And it really, it really, really helps reinforce your journey in a lot of positive ways. And I think karma will also be on your side.

You guys, I just want to take a second to say thank you to you, the audience. This show doesn't happen without you. I am from the bottom of my heart. I am deeply grateful to you because I started Impossible Dreams as a platform to help myself heal and to help other people heal. This podcast is all about that. And without you, that can't happen. We help each other heal. It really does take a village. So if you could just take a second to click and subscribe, like us, rate and review the show. Your comments really do help. Not only do they help us bring you other guests that you want to hear from, but they help us improve the show. They help us grow the show. Your engagement helps us expand what's possible for the reach of Impossible Dreams.

So thank you. Truly thank you.

Thank you for being a part of the Impossible Dreams team.

I think that's a beautiful principle. Like my mom was always, 'Send thank you notes, send thank you notes.' So when I got to New York, I mean, one of the ways that I hustled everywhere with obsession, you know, was I'm going to reach out to every casting director that I've auditioned for with a thank you note. And even if it was just a small job. And sometimes I would hand deliver them. Sometimes I definitely overshot, like you said. But the power of a personal note. And the president of Fox, Charlie—I'm now blanking on his last name—when I was doing a series at Fox, gave the series regulars, he gave us a Christmas gift. And it was a box of beautiful personalized stationery with our names on them.

And his note to us was, 'You can never underestimate the power of a personal note.' And I thought, 'My mom was right.' And my parents—it's just a quick another story about this. One of my first acting teachers just passed away a few days ago from high school, Celeste McMenamin. When I got a job in my first Broadway show and was going on, I was understudying one of the lead roles. When I was gonna be performing as that role, my parents bussed up 200 people from my hometown. And that particular teacher, Ms. McMenamin, she is in the picture that I have framed when the Philadelphia Inquirer did a weekend cover story called 'That's Their Boy on Broadway.' She is wearing a T-shirt with my headshot on the back, you know, pointing at the Phantom of the Opera marquee in Times Square because my parents were willing to give back knowing that it was these teachers, you know, that had such a powerful influence on my life.

And that's another reason that it's so powerful is it takes you very little time to show that appreciation, but the energy, positive energy it creates for the people that invested in you is so great. They still talk about it.

The people who were there still talk about that.

Yeah, absolutely. Was talking to Danny Meyer this past Monday. We did a book launch dinner at Union Square Cafe, which is appropriate considering his place in the book. Yeah. He was talking about why he wrote a book. His book is called Setting the Table. First of all, Danny's had such an impact on the entire industry that he's a part of. People study his work. I'll meet a chef in San Francisco that went through New York as part of their training and happened to work at a Danny Meyer restaurant, and they hold it dear to their heart. They're very proud of having been through that experience, uh, organization. But he said, 'I can only open so many restaurants. If I really want to impact people more broadly, I had to write a book because, because that way my best practices and principles get shared even wider.' And it's just a—it's an incredible mindset like that, that if you studied all the way up and if other people were innovators and you were learning from them,

Then you have this kind of responsibility as you get higher and higher up, I think, to turn around and do the same thing. And I think all the greats do it.

Yep, yep, yep. And I love that you're saying, you know, you don't have to wait until you're a great to do it. Nope. Do it all the way. All the way. Make it a part of your practice.

Yeah. And then it doesn't feel like work, too. If you—if it becomes one of your moves, you know, one of your moves in your—in your daily life, then it's not, 'Oh, I don't remember. Oh, my mom told me to write notes.' Like, you develop an intuition for it, and then you can do it more, more quickly, more of the time, and in more unique and innovative ways. So it's a great skill to have.

Yep. Especially now, because I think now, you know, we're in such a different world. You can differentiate yourself, you know, on your way up if you practice that kind of personalized outreach. All right, Bill, so we only have a few minutes left. No worries. Do you have anything else you want to share about the book before I ask you just one or two more questions?

I would just say that if there is anyone out there who even has an inkling that there might be this other thing that they want to go try, I would encourage them to read the book because I hope I bring to life the possibility that it could be real and give you the tools where you could imagine yourself actually attacking it. And I would—you don't have to quit your job tomorrow or quit what you're doing. You could imagine what this thing's going to be, especially with today's AI tools and whatnot. You could make a plan. You could say, 'Okay, in six months, I'd like to know whether I can take a shot at this and start role-playing what it would look like.' And what are you going to do for the next five months?

AI will answer that question. You can say, 'I'm thinking about going to do this,' and it'll literally build a plan. Absolutely, yep. But visualizing that and learning about the principles in this book may give you that extra bit of confidence to actually step out and try it one day. And I would say the same thing for parents and counselors who have this fear. 'Oh, my God, would that be quixotic?' I think it is. It can help everyone breathe a little bit deeper, and maybe they can go along for the journey. I think when parents finally do flip a bit and become supportive of this dream, some magical things can happen in that relationship as well. And you don't realize you're saying no to the dream.

You're not outright saying no. You're going, 'Yeah, yeah, yeah, but what about your chemistry class?'

Yeah. I mean, I find myself there all the time with my son who, you know, wants to reclass for basketball and, and, you know, potentially redo eighth grade just, you know, so that he can enter high school as a six, five freshmen instead of six, three, you know, and yada, yada. And I go, How important is school to him? How important is school for me, for him? Because he's obviously a smart kid. I know a lot of people that are insanely successful, never went to college. Like, I think we're in an interesting world in AI. He did exactly that last night. He got all excited. He had finished watching Rocky. We were watching Rocky. And he goes, Dad, he trained so hard. He goes, ChatGPT just told me how I can put the same number of hours in basketball between now and college if I don't reclass than if I take the extra year to reclass.

So I'm going to go over that with him today because I want to see. That's where his brain's at. Let's jump to AI for a second. Yep. So I've heard you say that basketball, venture—being a venture capitalist is being a recognizer of patterns. Is that—is that true? Yeah. Oh, yeah. With AI as like the ultimate pattern recognizer, do you see AI taking over VC jobs?

I think that any—I actually don't, and I'll tell you why. And it relates to, I think, all jobs that are out there. But the edge of being a great venture capitalist requires just a really amazing amount of nuance. In fact, the reason a partnership works well is you're going to have five different people opine on whether we're going to make this bet or not. And this bet's very last minute. You might have just met the company, like—the things you have to assemble, you know, what AI is really good at are the things that are very rote. So the formulas we've all figured out, the things you can write down. And unfortunately, a lot of the things that we teach in school around science and math are things that it can actually figure out quite easily.

And it's the subtle nuance in any field that's not baked into the LLM models. And so this is where I go back to this notion as an artisan. If you're really thinking about your craft, whatever it is as an artisan, you've studied the history, you're a continuous learner. The way you're differentiating yourself is what's out on the edge of that field. And that's the last thing the AI is coming after. If you went into a job because you thought it was safe and you studied it, but you don't really love it, you're not trying at home to get even better at it. I think those are the people, oddly enough, that are kind of sitting ducks for this new technology that's coming along.

Oh, interesting. Yeah. Speak about that a little bit, if you would.

I do... Every—the thing—LLM is really good at executing rote things, whether it's, you know, like paralegals are an area that are getting—that are being replaced. And if you just are moving text around, if you're just applying a formula you learned in chemistry class, and you're not searching for what's constantly new in a field, then I think you have some dangers. And the thing is, if you are this type of high-agency person that wants to know as much as they possibly can, AI is a superweapon, like it's a jetpack. And so I... Mark Cuban, who you mentioned, had a tweet the other day. He said there are two types of people: those that use an LLM to learn as much as they possibly can and those that use an LLM to not learn at all.

And I thought that was provocative. And so if you're high-agency and you want to hone your craft and learn as much as possible, find as many mentors as possible, AI can help you on all fronts. But you need to be running forward. It's not going to help you if you're sitting still. I love that.

And it actually speaks to, like, those people are going to need to read your book, you know, because you're actually pushing people away from jobs that are like, 'Hey, man, if an AI can do that, are you really passionate about it? Is that really...' But I know, I know, I don't know if you know Scott Galloway personally, but—but he's got a quote that I kind of disagree with, which is, 'Follow your talent, not your passion.'

Yeah, I know.

And I go, 'No, no, no. Listen to Bill Gurley because it's about...' you know. So anyway, I hope—I hope the people that are at highest risk of, or at risk of, you know, these jobs being replaced, find inspiration in your book.

By the way, there's another thing. I mean, other people have brought up that Scott has that point of view. The people that really dent the world are the ones that are passionate about what they do. I mean, they're fascinated in the art that they're executing on. Those are the ones that have the biggest impact. You're not going to get to that place.

And you're going to hone your craft. Like you said, that's point two, you know.

Yeah.

You got to, you got to, you got to go. I'm passionate about this. But, you know, if I'm not here, the holes in the ship are holes in the game, I got to, I got to fix it. I got to make them.

And one last thing on the end. And this, I think, is the key. If you're completely fascinated with something, to hone your craft, the continuous learning gives you energy. If you're forced to study a subject you're not that interested in, it feels like work. And it's why people that are in this lane have that flow state you're talking about all the time. They don't even realize they're practicing or learning. Like it's all part of the journey because they care about it so much. And they get energy out of that. And that's why if you're someone whose studying sucks energy and you're competing against someone whose studying gives them energy, you're going to lose. You're just flat out going to lose.

You're right. You're 100% right. That's definitely the acting game. That was the acting game for me. When I lost, when it was a drain, not a gain to audition, because sometimes you're auditioning 100, 200 times before you're getting a job. If there's somebody out there where that 201st audition for them is still a gain and it's a drain for me, they're getting that job.

That's right.

What is the toughest challenge you faced, and how did you get through it?

You know, this is going to sound like a weird answer to the question, but as someone who's six-foot-nine, like, like, recognizing, you know, this happens to almost all athletes, but I got to a place where I was near people who were going to have a lifetime career. There were two guys on our team that played in the NBA. But it was very obvious that, you know, it became very obvious very quickly that I was of a limited skill set in this sport. And it was humbling. Like, it was really, really humbling. And felt... I think it felt like failure, but... but, but it oddly, I think, gave me the recognition that if I could find a lane that, you know, where I could really thrive, that I knew what it felt like to see that kind of success.

And in some ways, I think, gave me more confidence when I got in a lane that was my own, you know, not that lane. It's an odd way, it's an odd thing to say, but I remember, like, being mentally impacted by that reality, but not letting it, not letting it, you know, become debilitating or anything like that. I almost turned it into a positive energy when I, when I felt I had some momentum in a different place, it gave me the energy to run at it.

Last question. What now would you say, you know, other than the book, which is pretty exciting—and if the book's the answer, that's, you know, more than amazing—but what would you say your Impossible Dream is now?

Well, I would love to see the book be radically successful and unlock as much human potential as possible. I've already met people who watch the video who are in one lane that have flipped lanes, and they're so happy that they're now doing this thing that they always hoped in the back of their mind they would do. And if I can get 1,000 people to do that, I'll be thrilled. If I can get 10,000, the more on that front that I can help people find that path, because I've met the people that are in that lane, and they are so happy. And they give back. They emit energy. They give back to others. It's a real force multiplier. So I just really love to see that happen.

Love it, man. Love it. Let's send people. Where can they go to get your book?

Well, if you type Gurley and Dream, G-U-R-L-E-Y and Dream into Google, you will get to the book. That combination of things will get you there. That's awesome. And I did the audiobook. Some people, for some reason, like the baritone of my voice. No, I love it, man.

You got a great voice. Some of my favorite books, whether it's McConaughey doing Greenlights or— So good. Yeah, David Goggins doing his Can't Hurt Me and, uh, Viola Davis. I mean, I think it's great to have the author. Yeah, if your voice is great, you know, which yours is, it's—it really changes it. I know. I think it's awesome. Bill, we appreciate you coming on the show. All right. Thank you so much, and thanks for having me. Yeah, dude. Yeah, it was—it was, uh—it was a real honor and a treat for us. So thank you. Thank you.