Bill Gurley on Failure, Mentors, and Why You Need to Relax About Your Career

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I've read a lot of interviews with you. Invariably, somebody asks you about Google and your missed opportunity to become an early investor.

I've never been upset by that. In fact, I've often told that story. It's quite a lesson, right? Like in venture, missing something like that is the biggest kind of mistake you can possibly make. Investing in something that doesn't work, you lose one times your money. But here, you missed out on an opportunity to make 10,000 times your money. Having lived through that, I think it was motivating. Like, I'm not going to let that happen again.

Hey, everyone. Welcome to How Success Happens. I'm Dan Bova, writer and editor at Entrepreneur.com. And I've got a cold. But more importantly, I've got an incredible guest today. Bill Gurley is a legendary investor, general partner at Silicon Valley VC firm Benchmark. He's invested in and served on the boards of such companies as Nextdoor, OpenTable, Uber, and Zillow. I've heard of a few of those, so he must be pretty good at what he does. He has written and spoken extensively about the intersection of business and technology and has a new book coming out called Running Down a Dream. That will be available on February 24th. Welcome, Bill.

Thanks for having me, Dan. Greatly appreciate it.

So, Bill, my first question is this. I looked at your bank account, and I'm fairly certain that you're probably the most financially successful person who has come on the show. So my first question is two parts. What made you want to write a book? And more broadly, what makes you want to do anything anymore? You could obviously just stop writing and live a very comfortable life for the rest of your life.

I was in a moment in my life where I was reading a ton of biographies. I imagine a lot of your listeners have had that journey or go through part of a journey like that. And I noticed this kind of common thread across these three dissimilar biographies, people from faraway fields. One was a restaurateur, one was a folk singer, and one was a basketball coach. And they all started from zero with a lot of intentionality, and they all ended up at the top of their field. And I noticed that they were adopting a similar playbook. As an idea and a writer, like the minute it clicked, I felt like I had to. I literally have a place where I keep notes for new ideas, and I wrote it down and I did it as a presentation at the business school where I went, and they posted it online, and a couple people noticed, like James Clear, who wrote Atomic Habits, saw it and said, 'This is fantastic.'

You're being a little bit humble with your video. A few people saw it. A few million people saw it. But it is an incredible video, and I definitely suggest people track down this talk that Bill gave. So who did you speak to when you talked to people for the book? Who did you talk to?

A lot of people gave us a lot of their time. And, you know, some of the stories are just fascinating. One of my favorites is a woman named Jen Atkin, who is one of probably the most successful hairstylists, you know, if you measured it by impact or financially, of all time. And she went to L.A. with $300 in her pocket, like with this intentionality to go do this, and finagled her way into a front desk job at a salon and then attended a free vocational school in cosmetology that's offered in the city of Los Angeles. That's still offered, you know, and most people don't take the opportunity to go do those things. And then, you know, and there's a lot in the middle that you can read about in the book.

But, but she parlayed this into an insanely successful career. And I love—I love those stories. I love them, and I think that they will land on people. And I think a lot of people have an inkling of a dream in their mind, and they think, 'Well, I'll get around to it later. I can't quite figure out how I'm going to go do that now.' And I think reading about people that took the leap will be confirmatory that it's possible.

Yeah, I love that. I love stories like that. Obviously, we write about people like that at Entrepreneur all the time. I love hearing them. You know, one thing that I hear a lot is not so much like, 'I can't do it,' but more like, 'Oh, I waited too long. It's too late for me to do that. I wish I did that back then before it blew up, but now it's too big of an industry. I'll never get in.' What do you say to people who think that way?

Well, two things I would say to that. One, there's a wonderful book by Daniel Pink about regrets called The Power of Regret. And he says the regrets that hang heaviest on people are what he calls boldness regrets or regrets of inaction. And as we get older, it's the thing we didn't do that really weighs on our psyche, not the mistakes we made. And so a lot of people are like, 'Oh, well, I'm afraid I'm going to do that and fail.' Yet, as you get to a later point in life, you're much more likely to regret that you didn't try. Bezos has this thing called the regret minimization framework. And there's a YouTube video—you can go watch it, it's just 10 minutes—but it's about imagining yourself later in life and saying, at that point, 'Will you wish you had tried?'

And so one of the things I hope with giving people all the tools is that they'll have more confidence in the effort. But also on top of all that, we have a chapter called 'Never Too Late' that gets specifically to your question, where we talk about a lot of people that did things very late in life and profile four people that started over 40. My favorite might be Burt Beveridge, the maker of Tito's Vodka, who lives here in Austin, who had a career as a seismologist and then as a mortgage broker, and came up with the idea to go do this at 40. And he's probably the most—I think it is the most successful spirits company in the country now.

So, funny story about him. A long time ago, I was the editor of Maxim magazine, a very highbrow magazine, if you're not familiar with it. But he bought an ad in Maxim magazine. This is going back years and years and years. And he came to our office and he was just like, 'I just want to be here and be in this moment to know that I could not only afford to run an ad in here, but my company is this big.' Like, he was just beaming. He brought vodka for everyone. It was just like, when you meet someone like that, you're like, 'This guy is in it for real. Like, he loves this.' That's got to be a through line of the people that you talk to. You can't succeed at something that you sort of like doing.

I think that's exactly right, Dan. And the first two principles in the book are, one is about identifying this thing that you love. We call it 'chase your curiosity.' And the other one's called 'hone your craft.' And one thing that I see consistently about people that are wildly successful is they, you know, there was a term, I think, in Seven Habits of Highly Effective People, 'sharpen the saw.' And they're constantly learning. You know, in fields like, like pro sports, you know, if I ask you, do you think Stephen Curry still practices outside of games? And, like, the answer is, of course. Right. But a lot of people in their careers, they quit learning at college and then they just go do the job. And these very successful people are constantly learning.

I call it external learning. They're spending their free time, their spare time, getting better at whatever this occupation is. And the reason that that is so critical to tie back to this thing that you love and to get to your question is if you don't love it, you're not going to do that part. And I think it's a great test of whether you're actually targeted at your dream job is, would you spend your spare time getting better at it or learning more about it?

You know, another thing that you write about in the book, I know, is—and this ties into learning—is mentorship. How do you make those connections?

Well, first of all, I try and divide it into two places because I think immediately people think they want their mentor to be Warren Buffett. And, like, that's not realistic. And so what I suggest is that they have a group of what I call aspirational mentors and then, the more realistic, pragmatic mentors. So the aspirational ones, make a list of the people who really stand out in the field you want to attack and study them and learn from them. You know, it's interesting, like going way, way back, you might've needed to meet someone for them to mentor you today, in this day and age, with YouTube videos and podcasts. Like, a lot of these people are out talking about what they do and you can go, like, consume all that.

And then, for identifying mentors you're actually going to meet with, just be more pragmatic. There are people two tiers down from the greats that no one ever calls, right? Find out who they are. They'll be flattered if you're studying them. And, you know, they may not all respond, but you might be surprised. Like 40% of them might say, OK. And then the last thing I would just say, different mentors can bring you different things. So you might use one mentor to know about one topic and a different one for another—leadership or some particular skill. And so you don't have to have this, you know, Yoda-type person who's all-knowing.

I spoke with Daymond John a while back and he talked about this a little bit and said, "You know, being a mentor, like, I'd love to give you advice, but don't come to me and say, 'I've got this problem. Give me money to fix it.' That's not what mentorship is."

Yeah, I think, you know, I mentioned in the book you need to be nuanced about how you approach mentors and the types of things you ask for. I think you can't waste a ton of their time. I think you can't pretend they want to spend three hours at a dinner with you. But if you can be efficient with their time, if you can know what they know that you don't, and if you can be very specific about what you want—like, I think it is OK to say, 'I've got this tactical problem. Here are three ideas I have. What's your feedback?' By the way, many of the people in the book that we profile did this thing where they identified the greats and kind of studied them. Many of them ended up meeting those people,

which is a spectacular moment in their story where they're starting to rise. They've studied these people, so when that moment happens, when that opportunistic chance happens, it's very easy for them to start a conversation because they know a lot about this individual.

I'm sure you get stopped a lot by people who recognize you. Is there a common question that is on the mind of a lot of entrepreneurs, or people who are trying to pitch you something, like what's the most common thing?

A lot of them are trying to pitch me.

So, yeah, yeah, yeah.

That's probably the most common. I do get asked a lot about breaking into venture, and so much so that I developed years ago—I developed like a five-pager that, that I immediately send to people and that, that explains how the industry works, explains what the real, you know, avenues of success are, and what the work product actually looks like, because I think there's some misperceptions, and then gives them a hint at how they might break in. And so, um, it's interesting. One of the things I do at the end of that letter is I say, 'If you really want to go do this, do these five things and come back to me.' And just that little bit of friction, really, there aren't that many people that actually made it to that next step.

What do you say to people now who are entering, you know, they just graduated college, and it's a different time to graduate into. College... For, people are struggling to get their foot in the door because they feel like AI has already replaced them. What kind of advice do you give to people who are in that struggle right now?

Well, first of all, I would tell them to relax a little bit. I think part of the challenge of the modern world is, with no malintent whatsoever, we've developed a philosophy about what children need to do from age 10 through 22 that is a gauntlet of... and I see people speak out about it. The college entrance process, Jonathan Haidt calls it the resume arms race that literally starts when you're 10. They put you in a lacrosse class and a cello class and a chess class and volunteering. And I think it's unfortunate because the... the kid is so wired to believe that they have to keep achieving, you know, on this path that they don't ever take the time to kind of take a deep breath and explore. We used to allow kids to go to college for two years before we allowed them to pick a major.

Today, you have to, at many schools, apply to a major. And I talked to one professor who studied math progression at college, and she says, if you've taken five courses, she can predict your major within 98%. Oh, really?

Wow.

We just lock people in. And the truth of the matter is, when you look across successful people, many of them are in a field far away from their major. And so, you know, and I met—I was at—I was at a university yesterday giving a talk, and, and a woman came up to me afterwards and said she wanted to switch from psychology to finance, and she was 22, and she said, 'Is it too late?' And I thought, 'Wow, what a crazy, like, unfortunate mindset to have.' And I told her, 'Look, if you transition to, like, a master's in finance after an undergrad in psychology, like, you know how many people study behavioral finance? Like, it's a big thing. Like, that could be highly differentiating. Like, you might do even better.' And so, I—that's my point about relaxing, like, just giving people permission. And I—and another, you...

...reality of this gauntlet we put these kids in, I think we've favored these jobs we view as economically safe. And as you point out, AI kind of throws a wrench in all of that. I mean, comp sci went overnight from being the job where you just can't not get hired to, 'Oh, my God, there's a bunch of unhired, you know, comp sci students.' So probably more of a reason to just really explore and find what you love, and don't do something for the wrong reason or for someone else's reason. And then the last thing I would say, just as a general advice to everyone out there: lean into AI. It is a tool of the future. And know, the best way to preserve your chances in any field, including programming, is to embrace it and to be superpowered by it.

I want to ask you, so we talked a lot about success. I want to talk a little bit about stumbles or misses. So I've read a lot of interviews with you and invariably somebody asks you about Google and your missed opportunity to become an early investor. So I have two questions about that. When someone brings that up, is there any part of you that is like, 'You know what? F-off. I've done a lot of good things too. You always got to bring this up.'? But then the second part of that, what is your approach overall to maybe missteps or mistakes? How do you turn those into a teaching moment? Do you scream into a pillow? What do you do?

Yeah, you know, two things about that. No, I've never been upset by that. In fact, I've often told that story. And I think I benefited quite a bit by having that experience fairly early in my career. So the story is I had Larry and Sergey present to the partnership when there were 25 employees and failed to chase is how I like to phrase it, because I don't know if we could have won if we chased, but we failed to chase.

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And it's quite a lesson, right? Like in venture, missing something like that is the biggest kind of mistake you can possibly make. Like investing in something that doesn't work, you lose one times your money. But here you missed out on an opportunity to make 10,000 times your money. And so it's just much greater. But having lived through that, I think it was motivating. Like, I'm not going to let that happen again. There's an article that—it's not an article, it's like a piece of writing that Tito did, Bert Beveridge again, that he gives out to entrepreneurs about how he tries to channel failure, which gets right at your question, which is he's convinced himself that he can use it as a motivator.

And so whenever he misses out or someone doesn't give him what he wants or whatever, he tries to turn it into fuel. And I think it's just—I think it's a really great attitude about the whole thing. It is super important for—in fact, the final chapter in the book I titled 'It Ain't Easy.' And I take all the people that we profiled their success and highlight some of the hardships that they went through. Because you can't have this mindset that if I hit my very first wall or my very first problem that quitting is the answer, you know. Tito says you never lose as long as you don't quit.

So we do a little segment. Let's call it 'Process Junkie' for a minute. Love to just drill into something that you are really good at. And I think one of the things that you are really good at besides making lots of money and investing and all that, you're a really good listener. Is there a skill that—is that a skill you developed? Do you have a technique to like turn off all the million thoughts going on in our heads and just listen to what the person in front of me is saying?

It's funny you bring that up. I wish I were better at that because I think I have ADD and I can fall away if something happens.

I haven't noticed. If you're thinking about your laundry, I haven't noticed.

But another skill I think... that I developed over time that I didn't have, you know, writing. I would—I was fairly unsuccessful in English and writing classes in high school and developed it as a—as a skill later in life as I read more. And so I would encourage people that, like any trait you think you're really bad at—public speaking, people think I'm pretty good at that, like, there was—I had no experience in it, you know, but I leaned into it and did it more and more. And so I'd say anything that you think of as a weakness in your personal skills, you can improve. I would encourage you to. And then there's a point—I have another piece of advice I give people—somewhere, I don't know if it's 35, 40, 45.

Somewhere you should exploit your strengths. I think early on, work on your weaknesses. But at some point, go nuts on your strengths. I don't think you have to do that forever.

I love that. I love that. I love that. So we have a question of the week that subscribers to our newsletter can answer. Anyone can subscribe. It's at info.entrepreneur.com. So on a recent episode, we had an underwater cave explorer on who's done some pretty scary things. So we asked people to say, tell us about a time that you voluntarily scared yourself. So my question to you is, when's the last time you did something that absolutely scared the crap out of you?

Well, I will tell you the story that pops in my mind. And my personal story, I embedded it at the back of the book. So if people want to learn more, it's in there. But I had been an engineer for two years, decided that wasn't my lifelong dream job anymore, went and got my MBA, but then I went to Wall Street and I was working on Wall Street for three years, had a successful career, but also came to this conclusion that it wasn't my dream job. And I was looking for other things. And I had one opportunity I was about to take. And then I got this pretty, like, crazy opportunity that would put me in Silicon Valley, which is where I wanted to be to try and become a venture capitalist. And I made this decision, working with the gentleman that invited me to come work for him, to switch coverage areas.

So I had been covering the PC industry, and I decided it would be closer to venture if I covered an industry more emergent. So I decided to cover the Internet, which was almost non-existent at the time. But I picked up coverage at companies like Netscape and CNET. And, um, the first part of the learning journey—I don't know if you've ever seen this smile curve of what you really know versus what you think you know—I was going down, you know, that first part of learning more. I—the anxiety just went, like, through the roof because I was like, 'Why did I walk away from covering this industry where I was considered an expert to this thing where I know next to nothing?' And I was taking meetings and I didn't

understand anything. And a lot of people, I would say a lot of people, especially going into new careers, they do well to study this smile curve because oftentimes they're just getting smarter, but you don't realize it because you're learning so much so fast. You just... confirming your imposter syndrome, but you'll hit the bottom. Keep pushing through, is what I would say. But when I think back on my career, that was one moment where I said, 'Oh, shit, what did I get myself into here?'

Well, I think it paid off. No, it worked out. It worked out. Yeah, yeah, it worked out. Okay, so we got a listener question. This is a little different. This is from Paul. 'Does being rich turn people into monsters, or does it just empower monstrous people to do what they wanted to do?'

That sounds like a loaded question.

Yeah.

Yeah, you know, one of the things, the sixth principle in my book is always give back. And one of the things that I've seen, at least among all the people we profile, is an enormous amount of humility and an enormous amount of respect for the industry. And, and an enormous amount of thankfulness for the people that helped them up along the way, and they all turn around, you know, and they started early, like they don't just start doing this at the very end, but they start giving back. And part of the reason, you know, I wrote the book was, was that part of my own journey. And so, you know, we... One of my favorite examples of this is a gentleman that most people probably never heard of, Mike Leach, who's a famous football coach, the Pirate.

And his win-loss ratio wasn't record-setting, but the number of people in his coaching tree is ginormous. So the point being that he had touched all these people's lives and, and literally set them free, you know, sharing ideas, like, didn't hoard anything. And so, I guess I don't... The, the people I profile, at least in the path they took, didn't lead to this type of megalomania person that the question is defining.

Okay. All right. Great. Good. Um, okay. So, uh, we can wrap things up quickly here with the little speed round. You tell me, please, what is a habit that you are happy to have, and one that you wish you could ditch?

I'm happy to have... I became a voracious reader later in life. So in high school, I never read—like, never, ever, ever read. And it wasn't until I was about 27 and when I was at business school that a bit flipped. I think, like most people, I can struggle with... being productive, because maybe that relates to the reading one, because it may seem odd, me saying that, but I'm so easily distracted by learning about something I don't know.

Besides your book, to reignite maybe someone's lost love of reading or to ignite it for the first time, what's a book that you think, "This is a good starter"? Yeah.

You know, one that pops in my mind that I think is remarkably interesting is Range by David Epstein. I'm currently reading Pinker's new book, and I recommend anything that Steven Pinker's done. And what else might I say? I'm just looking.

Oh, yeah.

This one's a bit different. It's for creatives. It's really kind of a completely different type of writing. But Rick Rubin's book, The Creative Way, it speaks in a different language than most books. But you walk away with very different anecdotes.

I love seeing you've got a lot of flagged pages on that. That's awesome. And then finally, you're, you're very good at a lot of different things. But what's one skill—has nothing to do with what you do—that you were like, "Man, I wish I was really good"?

Oh, this is easy. I am the... One of... I got to be a top-percentile fan of music. It's part of why I'm back in Austin. And I did pick up—what you see, the Stevie Ray Vaughan in the background—I did pick up a guitar during COVID, and I can play a little bit. But people encourage me not to sing when, when there's a campfire. Yeah. And when I watch people that have this gift, I just would be like, "Man, if I had that, I would do it all day long."

You and me both, man. I've picked up a guitar about every five years ever since I can remember. My God, I'm so bad at this! So I totally relate. Well, Bill, it's been amazing talking to you. And this book sounds incredible. Thanks so much for sharing all your thoughts on behalf of everyone who's benefited from your thoughts. We've got the book coming out February 24th. And what are some other ways people can kind of keep up with you and know what you're thinking about?

I'm pretty prolific on X. So it's BGurley, B-G-U-R-L-E-Y. And I share almost everything going on in my life there.

All right. Excellent, man. Well, I hope there are more books in the future, but I can't wait to read this one, Running Down a Dream, February 24th.

Thank you so much, Dan.