Bill Gurley | Benchmark – On finding your dream job, obsessive learning, and why passion beats the resume arms race

Hello, and welcome to The Dart Board with me, your host, Daniel Dart, founder and general partner of Rockyard Ventures. Each episode, I sit down with some of the world's best investors, operators, and entrepreneurs to pull back the curtain on tech, venture, and business. Whether you're just getting started in your career or you've been doing it for 30 years, we all know there's always more to learn, and I hope you get to learn some of it here. Thank you for your time, and on to the show.

Daniel Dart is the founder and general partner of Rockyard Ventures. All opinions expressed by Daniel and the podcast guests are solely their own and do not reflect the opinion of Rockyard Ventures. This podcast is for informational purposes only and should not be relied upon as a basis for investment decisions. Enjoy the show.

Today we have a super exciting guest joining us: Bill Gurley, longtime partner at Benchmark, one of the most successful investors in venture capital history—Uber, Zillow, OpenTable, Stitch Fix, the list goes on. But not only that, Bill influenced an entire generation of investors and thinkers, including myself, through his blog, Above the Crowd. So I was super excited to hear about his new book, Running Down a Dream, which dives into a question he's been exploring for decades, which is: why do some people thrive in work and they love it, but many people, most people don't and actually wish they could start over their whole career? So when I heard about this, I hit him up. I knew I had to have him on the show.

And we sit down and we talk about it. It's not a feel-good career advice book. It's really about digging into the patterns that Bill's seen across founders, artists, coaches, operators, and what actually separates people who found their thing from everyone else and how you can find yours too. It was a fantastic conversation and I'm so excited to share it with all of you. So without further ado, Bill Gurley, welcome to the Dartboard. Thanks for having me on, Daniel. Super excited about this. And just to set the tone of the conversation before we shift into your new book, I'm going to give a high level just about you myself. So long time GP at Benchmark, which I would say might be the most story firm in the history of Silicon Valley.

Huge, massive, amazing outcomes, but also, kind of like the book, you didn't have the stereotypical background. Wasn't an Ivy League guy, not a Harvard dude, or didn't go to some famous prep school. And so we're gonna talk more about that journey, and then really started this book based on a convocation you gave at UT. I'm a local Austinite, you're an Austinite, so that was super exciting. And so I kind of want to just jump in there and talk about this initial lecture in 2018 at UT, but you said you had been working on it for 10 years. And so the first thing is, let's go back to 2008. What was the impetus to start even thinking about this?

I was at a moment—I mean, I've always been an obsessive reader. Well, actually, since I went to business school, I've been an obsessive reader. Ironically, before that, I almost read nothing. So I had a bit flip. Um, that, that had a huge impact on me because, um, I've been an obsessive reader since then. And I was in a period in my life where I was reading a lot of biographies. I, you know, I think many people go through a similar phase, and I saw something. You know, I've been blogging for a long time, even before it was called blogging, writing analysis and in trying to understand how different markets work and different business models. And so, I think I had trained my brain to notice patterns and to look for patterns and alignment, because that's what I do when I put together a blog post, which is, oh, I think I see a pattern to how the world works.

I was finishing the third of these three biographies, and I just started to piece together things in my head. They all were doing the same things, and they were in radically different fields. One was a folk singer, one was a restaurateur, and one was a basketball coach. And the other thing that really spoke to me was none of those fields are things that your parents would tell you to go chase or do, right? Like they're not industries that are kind of sought after. And I think in certain cases, the folk singer, you know, I'll steal one of the reveals is Bob Dylan. And I think most people have no idea how studious he was and continues to be today. Like just a... a insatiable learner about his field. So anyway, when I noticed all these three things, I—I keep notes for unwritten blog posts, and I just started writing down a few things, and I—I said to myself, "If I ever get invited to speak at an MBA program, I'm going to put this together." And so that's why its roots go before the actual talk, because it took a couple years before that event kind of occurred.

And then I prepared it. And then I gave it. And what happened next was they posted it on YouTube, which I didn't even know they were going to do. And it started to pick up some views. And then it started to pick up this kind of underground reputation. You know, David Senra was talking about it when he was doing his Founders podcast and would draw notes from it. James Clear reposted it on his own website, which, you know, that's kind of a bit of a signal. Yeah.

Yeah. Yeah. I mean, that dude's a legend in his own right, man.

Right. And so anyway, those things started to, you know, then a few people said you should turn it into a book, but, but I was a venture capitalist. This isn't a book about venture capital. It's not a book about investing. It's a book about finding and thriving in your dream job. And so it was a back burner passion project for me. And one day I was at a conference put together by the Sogas, where they bring together a bunch of people that don't know each other. And one of those people was Brian Koppelman, who did Rounders and famously Billions. And he has this thing where he goes around provoking non-creative people to do creative things. Like, it's something that he likes to do. And so he was just poking.

What do you have? What do you have? What could you possibly put out there? And I mentioned it to him. He's also maybe a top 10,000th percentile Dylan fan. Yeah. So I shared it with him. And he was just insistent at that point. You have to do this. You have to do this. And so that nudge was the one that kind of pushed me over the edge. Tony Fadell also, who had come out with this book, Build, is a longtime friend of mine, the inventor of the iPod and head of engineering on iPhone and Nest. And he came out with this book, Build, and he said it was the best thing he'd ever done. Like, it was the most fulfilling. And he's done a lot of things, you know, and I highly recommend Tony's book as well.

So Brian first, Tony second is what kind of pushed me over the edge. And that's why this is something that took, you know, 10-ish years to kind of get birthed, because it wasn't my primary day-to-day activity. I almost had to get to a point in my life where I was moving past venture to have the time to really commit to it.

I'm so curious because Dylan really, it is such a story of reinvention. I mean, he's definitely one of my idols where it's like, hey, you can kind of pick and choose who you want to be if you're willing to put the work in. And you mentioned that right now that this might be the next chapter of your life. So before I kind of go to the next question, does this mean there might be more books in the pipeline or what does this mean?

I don't know about books. I went on a listening tour when I decided to hang up my venture investing shoes and talk to a lot of people at this stage in life. There's another great book called Strength to Strength by Arthur Brooks that is literally written about what do people do that have a lot of energy and time, but, but have kind of completed a career. And I'm fairly certain the next thing I'm going to go try, let's just leave it at that, is a policy institute. And some of you may have, you may have heard about the talk I gave at All-In on regulatory capture, and that, that, that, that experience and and the fact that kind of synthesizing that what I really love to do is analyze things, synthesize them, and hopefully bring clarity of thought, that it eventually dawned upon me that's something I'd like to go do. Yeah, I have a, a true north for this effort, which is, um...

There were a number of people that leaned heavily into supporting—we're way off topic—but nuclear energy as a positive, clean technology after it had been vilified, which wasn't easy to do because the mass consensus was that this is bad and Germany was deactivating all these plants. A combination of Steven Pinker and Elon Musk and a bunch of other people just said, 'No, you guys all have it wrong.' And then seemingly overnight, like three years ago, like common opinion just flipped, you know, just flipped.

And so even venture capital money started flowing into it.

Yes. Yeah. So, I mean, it—just the night and day difference, um, through, through a voice of reason and through a effort of education by, by some really important people. And so that's the kind of, I look at that as an example of something that I'd love to go...

And I'm sure you'll probably talk about direct listings there.

That one would be in there, but like, you know, helping with the U.S. healthcare problem or K-through-12 schools in America, those are probably more important, yeah, than fixing—I'm hopeful tokenization will fix that, that problem, but we'll see. I hope so. I mean, we just talked about John earlier, so I'm sure that he must be super excited to dig into this stuff with—yeah, I mean, he's, he, I, when I, when I, when I felt myself pointing in this direction, I went to visit him because obviously this is what he's done post his investing career. And I won't do it exactly the way he did it, but, but I did, I was eager to learn from his journey.

So fascinating. Okay. And so switching back to the book, you talk about some principles and frameworks. I'm curious, as you started writing about these people and you talk about the basketball coach, you talk about Dylan, and when did that go from, 'Hey, I'm writing about these people, I'm starting to assess them,' to, 'Actually, I'm going to distill this down into a core set of principles'? And is this something that you've intuitively done your whole life? Because, you know, in venture investing, you're also building frameworks. Where did that come from?

Yeah, I think it is something I've done my whole life. I started on the sell side way back when I had a fax that became an email newsletter that became my blog. And that type of distillation is something I've always done. You can go back and look at some of my more famous posts, 'The 10 Essential Elements of a Good Marketplace' or 'The Keys to the 10X Revenue Club.' A lot of them have lists, you know, a lot of them are meant to be educational and have frameworks and lists.

So, and if people don't know, right, it's Above the Crowd. It's a very famous—it looks very tall, too, so he stands above the crowd. I don't know if that's what it meant, but no, that is what it meant.

It was a little, a little pun, but yes. Um, so anyway, yeah, I do think I've always done that. And we had five principles in the talk. We added a sixth one in the book from talking to a few other people. And in the talk, I called them tenets. In the book, we've structured the book in a very unique way. We alternate chapters between tenets, learnings—or I call them the tools for success—and profiles, which are the stories of success. So we have profiles and principles. I love alliteration. So you get the double PR there. But the book, Michael Dell's book, I don't know if you ever read it or listened to it. I actually recommend listening to it because he did the audiobook, which I did also, for the record.

He alternated two different stories interleaved every other chapter: the fight with the PE firm over the future of Dell and the founding story of Dell. And each chapter would alternate. I think, from a reader's standpoint, it's kind of an interesting little twist because you find yourself wanting to go back to the other one. Yeah, you get a little break and then you want to go back.

And so question: what, what are your favorite biographies? Because I feel like you're an undercover biography expert based on just the—probably not as much as like, who's, who's probably read more with the Founders Podcast, but, um—

You know, the Danny Meyer one is really, really good. Like, really, really good. I mean, some of them are the ones that I built. The Bob Dylan one's fascinating. I like the Neil Young one, too. These are very long books. But the sixth principle we added is "Go to where the action is." And one thing you find in the Neil Young book—you know this movie Echo in the Canyon? Yeah. It's about the fact that the Eagles and Neil Young and Crosby, Stills, and Nash and Jackson Browne, they were all in the exact same physical place at that moment when it all came together. And I think they all benefited from each other being there and the amount of energy that happens when you have so many people co-learning in a field.

I heard you say, "Go to where the action is," before I read the book. I've heard you say that numerous times.

Yeah, we just didn't have it in the original talk. When we expanded the stories, Danny and Dylan went to where the action is. If you're a basketball coach, you can't really do it because everyone's spread out. But there are forms of it. You can go to conferences. You can immerse yourself where the active learners in that field are congregating.

I agree. I remember reading you mentioned on Twitter a long time ago. And at the time, I didn't have such a routine of going to San Francisco so much. And I remember talking to my partner, being like, "Babe, I got to go more, just because with AI, everything's happening. I need to be there." And then, so to see it interweaved in the principles was super cool.

And, you know, there's all these famous stories of people going to Nashville. I think, you know, songwriters, I think it's intimidating for someone. And I think there's this, what I might call a bit of a self-delusion where you tell yourself, "Well, I'll just be the best in this other city." And... think the only way that's even possibly realistic is if you go to this epicenter and then, and then learn everything you can and move—maybe Willie Nelson coming to Austin or whatever—but, but I don't think... You bypass so much optionality by not being right there where all the atoms are bouncing against one another. And part of the reason why you're intimidated, or a young person is intimidated to go there, is they're like, "How can I win when there are so many greats there?"

But many of these—very few industries are a zero-sum game. A rising tide lifts all boats. There's lots of winners. And with the exception of competing for an NBA championship or whatever, everyone can rise together, you know, and you're better off being there co-learning with everyone else.

Yeah. As you started building out these frameworks and you started kind of assessing really these kind of almost like, like titans, how did that influence how you're meeting founders and all of those things? Are you also looking for that intrinsic motivation of like rapid learning? Because you must see like, 'OK, Danny's the best. Dylan's the best. Now I'm about to give $20 million to this guy.' Are you starting to think, you know, reverse engineer that as well?

There's some chance I'm piecing it together after the fact, Daniel, but that's okay. But I just kind of want to admit to that. One time I asked Jeff Bezos how he was such a successful angel investor when he's busy running one of the biggest companies in the world. And he said, 'Oh, it's easy. I just have one trick. I asked myself this question: Is this person going to do this no matter what? Like, whether I'm involved or not, whether they raise money or not?' This kind of raw determinism. And I think, you know, one of the key takeaways of the book is if you do what you love, learning's free. And if you learn faster than everyone else, you're going to elevate yourself tremendously. And so what I think many founders have is just this obsession about what they're doing.

And then they become the most learned just as a result of competing on the edge. And so most of the founders, many of the founders that are running AI companies today didn't spend the past 10 years as AI academicians. But when it happened and when it started to happen, they immediately rolled around in it and became exhaustive, such that they very quickly crept to the edge of whatever field they were in. So I do think that the thread that you're poking at, I do think great founders are obsessive about being the smartest, most learned people in their field. And that learning isn't—I think with founders, it's not so much about the history. And I have strong opinions about why it's important to understand the history, but it's more about the edge.

And I think both of those areas are areas where any human can differentiate themselves: knowing more about the history and knowing more about the edge.

Yeah, I say that. I say, 'I may not be the smartest guy in every room, but I can be the most prepared.' 'You can be.' 'I can outwork you.' And even now, I'm like more of a sector specialist. But another factoid is you did a podcast, Masters in Business with Barry during COVID. And in that you said, 'If I was getting into business today, I would be a specialist because if we go one-on-one and he's a specialist, I'm a generalist, he's going to go deep and knock me out.' And that was one of the reasons where I was like, 'Okay, there's a point to that. I need to focus down.'

Yeah, yeah. I've long felt young people—I mean, I've long felt that venture capital is a young person's game. And one natural advantage a young person has is they can go very deep in a new emerging sector. And most people that become very successful venture capitalists become generalists. They also acquire extra homes and properties, other activities in their life that distract them from this. But yes, I think, you know, if you go, if you tell yourself, 'I'm going to be the most learned in this particular field,' you actually can. And the thing that is super serendipitous for me as I put this book out there is learning has never been more at your fingertips. It's unbelievable. Yes. I mean, it was that way before AI, just with podcasts and Wikipedia.

But now with AI, it's—you can sit there, you can even just turn on voice mode and just sit there and ask questions till you're blue in the face. And so this point, which I think is worth reiterating, like, nothing can stop you from being the most learned, especially if you narrow this down to a certain sector or you say, 'Within my age group,' or, 'Within my peer group,' or let's say you're coming out of a college, like, 'Within the people competing for the same job I am.' You can actually have more information in your head about that subject than others if you choose to put yourself to it. And this is why the first principle is about finding your—I call it, 'Chase your curiosity.' It's about finding your passion.

If it sounds boring and exhausting to be that learned, I think you're in the wrong place. I think it's an interesting test of whether you're tilting against something you're truly passionate about.

And I'm going to—I'm going to push on that because one of the great, great things, I think, about the book is you actually give frameworks to pull that out of people. 'What would you do if you didn't have to do it?' Like, what are the things that you're naturally excited to do? And for me, I didn't actually start venture investing professionally until probably two years after I heard that podcast. But at that point, I was like, 'Hey, if there was a great VC and he was giving information out anywhere, I would listen to it and take notes.' Right? And so I think it's one of the things—like, I love my job. I don't want to say, 'Oh, I would do it for free,' but I would. Like, I sometimes, like, get to pinch myself.

I'm like, 'Man, I can't believe I get to do this.' And I love how you have a few of those things. And so I want to ask—and this is kind of a different question is—for parents or people who maybe have a sister or a brother or a colleague, how would you think about addressing them and having the conversation? Because you also say, 'Don't just live your parents' dreams.' How do you kind of think about pulling that out of people that you maybe care about that—I don't want to say lack ambition, but maybe don't know what their thing is?

I think there's a interesting challenge that has emerged in the United States educational system. And people are now worried about AI going after the sure thing jobs. But if you look at even pre-AI, you know, there's a Gallup poll where only 23% of people claim to be thriving or engaged at work. And 59% qualified is quite quitting. That's 03%. We did a survey with Wharton and asked people, if you could go back again, would you choose a different career? And six out of 10 said yes. So I fear what we're doing. You know, we got obsessed with getting a college education. Interesting that you don't have one. and pushing kids into what Jonathan Haidt calls the resume arms race. And somewhere around 12 years old, parents are already worried about what college you're gonna get into.

And you're taking cello lessons and you're doing all this stuff. And one thing you're not doing is you're not—you don't have a lot of free time and you're not playing. And I think those in my generation, the parents were a little less obsessive, and there was just a lot more exploration on your own time. There's a great quote in Rick Rubin's book where he says, 'As children, few of us are taught to understand and prioritize our feelings. For the most part, the educational system doesn't ask us to access our sensitivity, but to be obedient, to do what's expected. Our natural independent spirit is tamed. Free thought is constrained.' And so we're just pushing them through. And the one thing I would say, first of all, I think the book will be really successful with parents, and I'd encourage them all to read it.

I've already gotten some incredible notes from parents who have gone through a phase shift in their own mind. When your kid comes home and says they don't want to be a finance professional, they don't want to go work at McKinsey, but they want to open a restaurant like Danny did, most parents freak out. They have to go through a phase transition of their own that goes from acceptance to embracing. And I've gotten these notes from parents that have gone through this phase shift. And the last phase is being truly excited and supportive of their kid. And there's an amazing story embedded in Greenlights, the book by fellow Austinite Matthew McConaughey. And he had told his father his whole life he was going to be a lawyer.

And he got to the University of Texas and he started hanging out with some people in the film program. And he decided he wanted to switch to film school. And he was scared to death about what his father was going to say when he told him this. And he waited and waited and waited, you know, weeks upon end before finally calling his dad. And he's nervous and he tells his dad, and his dad says, 'Well, don't half-ass it.' And he talks about in the book how those words were the last thing he expected his father to say, but the most empowering thing his father could have possibly said, because he said, 'I support you, but get after it. Like, if you're going to do that, go do it.' Great. And obviously he did.

But what I would like to—this is a very long answer to your question, but it's really, it's one of the core reasons I wrote the book—is I would love for every parent to have that opportunity or to be prepared for that moment and to be supportive, you know?

I was thinking about the Danny Meyer uncle comment.

Yes, absolutely. Yes. Well, he—I mean, more than even supportive, his uncle pushed him across the table, you know. And Danny, you know, classic example, Danny was a salesman who was making over 200 grand. And this is, you know, 30 years ago, so a lot of money, and was thinking about going to law school. You know, he was following—this is where I talk about your parents—you're following these things, not only your parents, but society kind of tells you to go on these paths. And his uncle at dinner said, 'What are you doing taking the LSAT? You were born to open a restaurant. You should go do it.' And luckily he had enough money from the sales job, but he very deterministically at that point...

And one of the things I love about the Danny story is how intentful he was at that moment when he switched. And we've now found many, many stories, but we were always looking for this moment of intent because I think it helps the reader think about them doing it themselves as opposed to someone maybe that stumbled into a career.

In your moment of intent, you know, you're working at Compaq and then you're like, 'Hey, I'm going to go do an MBA.' And then you become a writer. What was the moment of intent? Where was that? Because there has to have been a moment because it's a radical shift.

Yeah, yeah. There were a number of things that were going on in my life. I... It's funny, when I was very young, when I was legal to gamble, we would go to Vegas and count cards—single-deck blackjack. And the notion of money and odds was always in my brain. And then when... about the time Prodigy came out, which was a precursor to AOL...

Um, I remember Prodigy, man. Yeah.

I, I read One Up on Wall Street by, uh, by Peter Lynch and I immediately started trading stocks. And so this is while I'm an engineer, I'm doing these things on the side and it gets at that point of what is it you're doing with your free time, right? I'm, I'm doing this, you know, just because I'm curious about it. And, uh, luckily, my sister led me to Compaq. So Compaq at the time, most people probably don't even remember it today, but was one of the hottest startups in the land. John Doerr was on the board. And so I was exposed to a company being public and employees getting stock options and tech disruption and everything. Kind of combining all those things, when I was at business school, I decided if I ever could, I would take a shot at venture capital.

I wasn't able to coming out of there, and I went to be a sell-side analyst on Wall Street. But it was always in the back of my mind, and I was waiting for that opportunity. And one day it came up, and I was prepared to jump at it.

And on that note, I had heard, again—I don't know if this is true—I had heard that a lot of Benchmark recruiting you was due to your blog and your writing and your ability to communicate really kind of cohesive thoughts.

There are many different ways to be competitive at venture capital. And I know a number of people who do it well. I think of my partner, Peter Fenton, who's not very out there. But there are a handful. It is a successful strategy to create a voice for yourself. And, and to kind of think out loud. And I also, you know, point to other great investors, although don't want to sound pompous, but like Buffett or Howard Marks, who have constantly done this themselves throughout their career. And so it was a model that I had seen others do that I had benefited from and was very natural for me.

Yeah. And then even then, you still didn't have a linear path into VC, right?

Well, it's kind of an unbelievable story, but I decided I'd been a sell-side analyst for three years. And this is a point I make in the book. Like, I was an engineer for two and a half years and a sell-side analyst for three years. I don't view my decision to not make that my life's work as failure. That was me, you know, tilting at something, learning from it, and then recognizing in both cases that it wasn't something I wanted to do for 25 years. And so I moved on and did something different. And there was the sell-side analyst job. One thing is just so amazing about it. You're 20-something years old and you're talking to CEOs and CFOs. The access you get in that role is insane. But it has a lot of negatives.

And there's no reason to go into them now, but it has a lot of negatives. So after three years, I decided I didn't want to do it anymore. I raised my head. I was looking for other things. And I kind of randomly got a phone call by Frank Quattrone, who was the top investment banker in tech and was leaving Morgan Stanley. And he had heard about me. And he said, "Bill, come work for me." And I said, "I don't want to be a sell-side analyst anymore." He said, "What do you want to be?" I said, "I want to be a venture capitalist." And he said, "I'll move you to Silicon Valley and introduce you to every venture capitalist that I know." Which he did. And I only worked for Frank for 13 months before I got VC offers.

So I owe a lot to Frank, but he knows it because I tell that story all the time.

That's pretty amazing. That's pretty amazing. And then a quick question before we kind of shift gears. When you think about this book and then also the context of AI with access to information, how do you think about it also with shifting dynamics around what the world might look like in a few years?

Well, no matter what field you're in, I think the right answer is to immerse yourself in what AI can do in your field. You know, there's a lot of anthropologists have talked about the fact that we evolve with our tools, right? Whether it's farm equipment or a microscope or whatever, like humans are always, their competitive advantage or what they're capable of is always a function of not just themselves, but what tools they have available. And it's imperative to recognize that, that this tool has a lot of power. And the best thing you can do to future-proof yourself is to be the most AI-learned person in whatever your field is. And so that would be my first thing to suggest to people. The other thing is, you know, there were a lot of jobs that people thought of as sure things, computer science, like paralegal, and maybe those aren't sure things anymore.

And while I don't wish upon anybody to all of a sudden be faced with a tough career situation, I do hope that it maybe disrupts what we've been doing with this industrial college complex where we've been pushing all these people towards things rather than letting them find the thing that matters to them most.

Yeah, well, on that note, since you started the book, has your idea of what a successful career looks like, has that definition changed?

No, not really. One of the things, you know, in transitioning from the talk to the book, me and my co-writer probably read a hundred new biographies looking for other stories to share. And it was funny, I was giving a talk about the book at Johns Hopkins University and one of the young adults there said, 'What if you care more about purpose than passion?' And I reflected on it a bit and I thought about all the people that we profile in the book. And these people that become super passionate about a career and rise to the top, inherently impact hundreds and hundreds and hundreds of people. I mean, if you meet a chef that's been through New York City, they know who Danny Meyer is. They might have worked in one of his restaurants.

And if they did, it's one of the proudest things that they have. They talk about it when they introduce themselves. And so, even if your main priority is purpose, I think that being the most learned, being at the top of your field gives you more opportunity to shape and impact more lives than almost anything. Yeah. And almost every one of the stories, if you get the book and read through it, almost every one of those people have that impact. You know, Bobby Knight, for all the negativity that people have about some of his tantrums, his coaching tree is beyond imagination. And so there was a point about being a learner coming up that you naturally become a teacher and, and, and, and you're not possessive or obsessive about retaining proprietary knowledge nor retaining proprietary people.

You know, you see this natural willingness and true excitement about protégés thriving.

Yeah. And even when we talk about basketball coaches or we cover some other ones in the book as well. And even what Dylan, I mean, how many people has he impacted? No, unbelievable amounts. Yeah, exactly. Unreal. Like even me, I think, the reimagining of my life, I saw the, uh, Martin Scorsese film, yes, and it just blew my mind, right? And so it changed everything. Um, now shifting gears, there's a few questions I like to ask everyone. The first is, what is the best advice that you've ever received?

You know, it's so cliché-ish, but I just saw on Twitter one of the... I keep saying David Senra, but he was talking with Tobi. I adore listening to Tobi from Shopify talk. I feel like I'm listening to... some kind of sage from another planet. But he was obsessing about reading and how it's like the biggest life hack of all time. I mentioned to you that when I came to Austin for MBA school, for whatever reason, and I don't even know what happened, I started reading books and I got to the end of one, I'd pick up another one. I would build my free time or my, I remember I decided I was going to commute by bus because it was 15 minutes each way where I could just open a book and move through it and dedicating time to that.

I think that's, I have a hard time thinking of something else because that one's so powerful and maybe it doesn't have to be books. Maybe it can be, you know, talking to AI or whatever, but, but this, this natural obsession with learning is, uh, will pay for itself again and again and again.

No, I agree with the, the book thing. And I think that one of my superpowers is, is, is reading. And I personally set out a lot of time to do it. And as I always tell people, you can take someone who's dedicated decades of their life to learn something and you can get that in four days. Yeah. It's truly miraculous. And then sometimes I talk about MBAs and I'm like, 'Hey, you meet what, 20 times a year for an hour with three hours of outside work a week or something? Like, you can replicate that on your own.' And there's so much power in that. I think sometimes people in life, like they're doing just enough to not get fired or just enough to get a passing grade, and long-form writing is magical.

Yeah, and that goes back to the Bezos letter project within the internal organization where he makes people write a six-page paper to defend a point of view. We didn't talk about it earlier when you were talking about me writing, but... But forcing yourself to write things down brings so much clarity of thought because you find yourself challenging your own inconsistencies, which then make you ask more questions to try and get at the right answer.

And speaking of that, what are your favorite books? And I, and I know a few because you mentioned a few on, on Barry Ritholtz's podcast.

And so, and you talked about like Santa Fe Institute and all of these other things of like, by the way, real quick, there's a corollary to the, to the reading thing, which is, you know, there's another cliché thing where people say there's no such thing as a dumb question. Like my whole life, if I'm talking to somebody, a lot of people can be almost pompous and say, "Well, you know this person, right?" And I think there's a tendency to want to say, "Oh, yeah," or "I know this topic." And I've just trained myself, if someone says something I don't know, I just say, "No, I don't. Tell me about it." I just immediately stop and say, "Well, if you think it's important that I should know this thing and I don't, tell me about it."

And so I do think people feel embarrassed that they might look unlearned. But, but it's part of the process of becoming learned and to be confident expressing ignorance in a situation where you can then learn more and take a step forward.

I think that's really good advice, too, for venture investors, because sometimes we meet founders and I think we try to pretend like we're smarter than we are, even though we don't know it. And remembering to tell the founder, "Hey, I actually don't know what you're talking about. Can you explain that to me better, please?"

So, um, onto the books, my publisher asked that I put a book list at the end of the book. So there's probably, I didn't add it up and now I'm going to go add it up, but I'm guessing 50 books at the back of my book where I list the ones that have impacted me. I'm not going to go through the whole list. And these are only nonfiction. I have some favorite fiction books. I got to know Cormac McCarthy at Santa Fe where he hung out quite a bit. And I think, you know, some of his work is just amazing, but from, from, from a nonfiction book. Yeah. The book about the Santa Fe Institute called Complexity was the one that probably, like, in my brain, I feel like it changed how I think the most. It's a bit hard to explain it to, you know, the Institute covers complexity, which I define as multivariable, nonlinear systems.

And there, there, you know, things like a stock market or the weather, and, and they're very hard to predict. But in analyzing those, you realize things like linear interpolation are really bad science, you know, and yet people do them all the time. And so anyway, that book had a huge impact on me. What other ones did I just, do I just, you know, A Random Walk Down Wall Street by Burton Malkiel. Like, I have people ask me all the time, "What stocks should I buy?" You know, "Should I do this SPV?" And I'm like, "Have you ever read A Random Walk Down Wall Street?" And they say, "No." I said, "Don't ask me another investing question until you read that." And, you know, I'm a big fan of self-help books. I think some people vilify them.

You know, Warren Buffett said the only thing, the thing that impacted his career more than anything was reading How to Win Friends and Influence People by Dale Carnegie, and he kept his Carnegie certificate on his, on his wall. So I think, I think the better books, whether it's Atomic Habits or or The Seven Habits of Highly Effective People or like Awaken the Giant Within by Tony—like, this stuff can motivate you, can unlock things, can give you—I think all of those books can be powerful. In venture, Crossing the Chasm, Innovator's Dilemma, you have to read those. Shoe Dog is so good. There's a book called Startup by Jerry Kaplan about the failure of Go Corporation. And everyone reads the success stories.

It's pretty enlightening to read a failure story. You could also watch the General Magic movie, which is incredible. And you get to see a very young Tony Fadell in that movie. But if you haven't seen that, it's free and on the Internet. And I highly recommend you go see it.

100 percent. That's amazing. On the other side of that, what's the worst advice or commonly held advice that you disagree with? And it can't be everyone should go to college. Yeah.

No, I mean, I'm gonna give you a couple. I think, you know, related to the book, I do think that this obsession we have about there being this confident movement through high school, college, like, like, yeah. And that it's safe and this is how you have to do it. And, and the obsession we have about getting into the right college, um, we're putting, I don't think anyone has malintent, but we're putting massive amounts of stress on these young people and, and we're really not allowing them to have the time to explore. And I just, I would, I'm hopeful I can help impact that. So that would be one. Then the other one, maybe for more for your audience, I think we talked a bit about an MBA program.

The notion of an MBA is vilified quite a bit in startup land. And what I fear happens along with that is the subject matter that's taught in an MBA program, whether it's marketing skills, sales skills, finance, financing, pricing. Those things matter to a successful company. And if we're moving into more fields with physical products, which venture capitalists seem to want to do right now, then unit economics start to matter. And cash flow becomes a big issue, debt financing, and all these topics matter. And so I just worry that the vilification of the MBA... gives you this willingness to kind of say all that stuff doesn't matter. And I think that's wrong.

Yeah, I agree. I think I had a lot of success when I ended up going back to school later on to go to MIT. And some people are like, "Well, why would you go there? You don't need it." And I'm like, "Man, I can go study with the smartest people on earth for two years. I know, like, six Nobel Prize winners now that I can text. That's life-changing."

There is an element, I think, if anyone does go to an MBA program, where you get out of it what you put into it. I think, unfortunately, you can coast through some MBA program. But as you said, you have this massive opportunity to take a pause in your career and learn obsessively. And so if you lean into it, it can be really, really rewarding.

Yeah, it was, it was life-changing. And I still talk to a bunch of my professors all the time. I'm like, "Hey, what do you think about this? What do you think about this?" It's, it's awesome. And I think just, I think who our heroes are matter, like who we look up and aspire to. And it matters. And like I said, I had gone to prison earlier in my life and I made that decision the wrong way, where it's like, "You are guilty by association for the good or the bad." And so to me, to go to where the action is—if you surround yourself with amazing people, inevitably amazing things will happen.

Yeah.

And so it's just fascinating thinking about that and kind of like hard life things. I'd be curious, what's something in your life that was really hard to overcome or really difficult, like even awful at the time, but upon reflection, you're like, "Actually, yeah, I got a lot of value out of that"?

I thought about a couple of different things. The one that in writing the book that I've thought a lot about, and I don't know this will apply to a lot of people, but as you mentioned, I'm very tall. I was 6'9". I'm now 6'8". I tilted at playing basketball as most people do with that height.

That's why I wondered about Bobby Knight. I was like, "Did he really come with that because of basketball, because you're tall?"

Well, and I found myself onto a D1 team, but I was at the very end of the bench, and I rarely played. And it was apparent. And our team was somewhat successful, and two of the players went on to big NBA careers. And so I had this window of seeing success at a very high level. But knowing that I was failing at it, I could just feel it. I don't think it was from a lack of effort. It was from a lack of skills. But I do think when... when I moved past that point in my life and found areas where I could thrive, I think having seen success at that level and knowing it's possible and knowing the people that did it gave me confidence that, "Oh, you can do it if you have an edge in that area." And so I can't prove psychologically that that's in the back of my head, but I think part of it was.

And it's always been something that kind of... I think pushed me. And one of the people that we talk about in the book is this incredible Austin founder, uh, Bert Beveridge, known as Tito. And, uh, he has a talk track he does with people about using failure as motivation. And if you can find a way to make it energize you, then you have this superpower. Because he says, "You don't fail until you quit. You just pivot and keep moving." And I think that's a really interesting mindset.

I agree with that. I think sometimes we confuse failure with catastrophe. Yes. Where it's like, hey, it's a minor setback. I'm still alive. I'm still healthy. I got another round in me. Let's go. Okay. In closing, a few things. One, first, where is Bill in 10 years?

Well, I turned 60 this year, Daniel. So that question, I think many of your other guests are younger. So that question's a little more daunting, I guess, if you will. Hopefully I'm healthy and active. But I guess if I try and be optimistic, you know, this Policy Institute thing I talked about is having an impact on some really important issues of our time.

So hopefully you open here in Austin.

It will be here in Austin.

And about the book, if there's one thing that you hope you can achieve with this, what would that be?

To maximize the number of people that it impacts. And I think what I really hope the book does is unlocks human potential. So I think there are a lot of people who, what if Tito never decides to start a spirits company? Which he did at 40, by the way. What if Danny just goes to law school and doesn't become the restaurateur that he is? The world's different because these people tilted at something in this kind of uber-passionate way. And there's always a chance that they don't take that step, right? Because they're intimidated. They don't think they can make enough money in that field, you know, yada, yada, yada. And so if I can get more parents, more individuals, more consultants and counselors to give people permission to go do this thing that they want to do, I think the world would be a better place. So that's—that's—and I've already—already have gotten some of this feedback from people with the video, but I—I hope this can be much broader than that, um, global even.

Yeah, I mean, I agree with that 100%, and I think it's amazing, and hopefully we can help just a little bit get that out there.

Yeah, well, thanks for spreading the word. I appreciate it.

Yeah, man, I want to say thank you so much for joining me today, man. It was truly an honor.

No worries. It was fun.

Thank you again for listening to The Dart Board. If you haven't already done so, please hit that subscribe button. It helps us a ton. You can also connect with me and the rest of the Rockyard Ventures team on LinkedIn. If you're building something great, we would love to hear from you. Until next time, I'm your host, Daniel Dart. Thanks a lot for listening.