- 1 week ago
Bill Gurley is a legendary venture capitalist who has backed companies like Uber, Zillow, and OpenTable. His new book, Runnin’ Down a Dream, is a user's manual for figuring out what you actually want and how to go get it. In this conversation, he shares some of his favorite takeaways from the book. Plus, Bill reveals the one skill he desperately wishes he had.
Category
🗞
NewsTranscript
00:00I've read a lot of interviews with you. Invariably, somebody asks you about Google
00:05and your missed opportunity to become an early investor.
00:07I've never been upset by that. In fact, I've often told that story. It's quite a lesson,
00:12right? Like in venture, missing something like that is the biggest kind of mistake you can
00:17possibly make. Investing in something that doesn't work, you lose one times your money,
00:21but here you missed out on an opportunity to make 10,000 times your money. Having lived through that,
00:26I think it was motivating. Like, I'm not going to let that happen again.
00:35Hey everyone, welcome to How Success Happens. I'm Dan Bova, writer and editor at entrepreneur.com
00:41and I've got a cold. But more importantly, I've got an incredible guest today. Bill Gurley is a
00:48legendary investor, general partner at Silicon Valley VC firm Benchmark. He's invested in and
00:55served on the boards of such companies as Nextdoor, OpenTable, Uber, and Zillow. I've heard
01:02of a few of those, so he must be pretty good at what he does. He has written and spoken
01:07extensively
01:08about the intersection of business and technology and has a new book coming out called Running Down
01:15a Dream that will be available on February 24th. Welcome, Bill.
01:20Thanks for having me, Dan. Greatly appreciate it.
01:22So, Bill, my first question is this. I looked at your bank account and I'm fairly certain that
01:29you're probably the most financially successful person who has come on the show. So my first
01:35question is two parts. What made you want to write a book? And more broadly, what makes you want to
01:42do
01:42anything anymore? You could obviously just stop and live a very comfortable life for the rest of your
01:48life. I was in a moment in my life where I was reading a ton of biographies. I imagine a
01:53lot of
01:53your listeners have had that journey or go through part of a journey like that. And I noticed this
01:59kind of common thread across these three dissimilar biographies, people from far away fields. One was
02:06a restaurateur, one was a folk singer, and one was a basketball coach. And they all started from zero
02:13with a lot of intentionality, and they all ended up at the top of their field. And I noticed that
02:18they were
02:18adopting a similar playbook. As an idea and a writer, like, the minute it clicked, I felt like I had
02:25to, I
02:26literally have a place where I keep notes for new ideas. And I wrote it down. And I did it
02:31as a
02:32presentation at the business school where I went. And they posted online and a couple people noticed like James
02:39Clear, who wrote Atomic Habits, saw it and said, this is fantastic.
02:43You're being a little bit humble with your video. A few people saw it. A few million people saw it.
02:48But
02:49you know, it is an incredible video. And I definitely suggest people track down this talk
02:54that Bill gave. So who did you speak to when you talked to people for the book? Who did you
03:03talk to?
03:03A lot of people gave us a lot of their time. And you know, and some of the stories are
03:07just
03:07fascinating. One of my favorite is a woman named Jen Atkin, who is one of probably the most successful
03:14hairstylists, you know, if you measured it by impact or financially of all time. And, you know,
03:22she went to LA with $300 in her pocket, like with this intentionality to go do this and finagled her
03:30way into a, you know, a front desk job at a salon, and then attended a free vocational school in
03:39cosmetology that's offered in the city of Los Angeles. That's still offered, you know, and most
03:44people don't take the opportunity to go do those things. And then, you know, and there's a lot in
03:51the middle that you can read about in the book, but she parlayed this into an insanely successful
03:56career. And I love, I love those stories. I love the, and I think that they, they will land on
04:04people. And I think a lot of people have an inkling of a dream in their mind and they think,
04:10well,
04:10I'll get around to it later. I can't quite figure out how I'm going to go do that now. And
04:14I think
04:14reading about people that took the leap will be, will be confirmatory that it's possible.
04:20Yeah. I love that. I love stories like that. Obviously we write about people like that at
04:26Entrepreneur all the time. I love hearing them. You know, one thing that I hear a lot is not so
04:33much like I can't do it, but more like, oh, I waited too long. It's too late for me to
04:38do that.
04:39I wish I did that back then before it blew up, but now it's too big of an industry. I'll
04:43never get in.
04:44What do you, what do you say to people who, who think that way?
04:47Well, um, two things I would say to that one, there's a, there's a wonderful book by Daniel
04:52Pink about regrets called the power of regrets. And he says the regrets that hang heaviest on people
05:00are what he calls boldness regrets or regrets of inaction. And as we get older, it's the thing
05:06we didn't do that really weighs on our psyche, not, not the mistakes we made. And so a lot of
05:12people
05:13are like, oh, well, I'm afraid I'm going to do that and fail. Yet, as you get to a later
05:17point
05:18in life, you're much more likely to regret that you didn't try. Bezos has this thing called the
05:22regret minimization framework. And, um, there's a YouTube video. You can go watch it. It's just 10
05:28minutes, but it's about imagining yourself later in life and saying at that point, will you wish you
05:34had tried? And so one of the things I hope with giving people all the tools is that they'll have
05:41more confidence in the effort. Um, but, but also on top of all that, we have a chapter called never
05:46too late that gets specifically to your question, um, where we talk about a lot of people that did
05:52things very late in life and profile for people that started over 40. Um, my favorite might be,
05:58um, Burt Beveridge, the, uh, the maker of Tito's vodka who lives here in Austin, um, who had a career
06:05as a seismologist and then as a mortgage broker and came up with the idea to go do this at
06:1140.
06:12Um, and he's probably the most, I think it is the most successful spirit company in the, in the
06:18country now. So funny story about him. Uh, a long time ago, I was the editor of Maxim magazine,
06:25very highbrow magazine, uh, if you're not familiar with it, but, uh, he bought an ad in
06:32Maxim magazine. This is going back years and years and years. And he came to our office and he was
06:37just
06:38like, I just want to be here and be in this moment to know that I could not only afford
06:44to an ad in
06:45here, but my company is this big. Like he was just beaming. He brought vodka for everyone. It was just
06:52like when you meet someone like that, you're like, this guy is in it for real. Like he loves this.
06:59Um, that's gotta be a through line of the people that you talk to. You can't succeed at something
07:05that you sort of like doing. I think that's exactly right, Dan. And the first two principles
07:12in the book are one is about identifying this thing that you love. We call chase your curiosity.
07:19And the other one's called hone your craft. And one thing that I see consistently about people
07:25that are wildly successful is they, the, you know, there was a, there was a term, I think in
07:30seven habits, a highly effective people sharp, sharpen the saw and, and they're, they're constantly
07:36learning. And, you know, in fields like, like pro sports, you know, if I ask you, do you think
07:43Stephen Curry still practices outside of games and like the answer is of course, right? But a lot of
07:52people in their careers, they quit learning at college and then they just go do the job. And these
07:59very successful people are constantly learning. I call it external learning. They're, they're spending
08:05their free time, their spare time, getting better at whatever this occupation is. And the reason that
08:12that is so critical to tie back to this thing that you love and to, to get to your question
08:19is if you
08:20don't love it, you're not going to do that part. Like, and I think it's a great test of whether
08:25you're actually targeted at your dream job is would you spend your spare time getting better at it or
08:32learning more about it? You know, another thing that you write about in the book, I know is,
08:36and this ties into learning is mentorship. How do you make those connections?
08:40Well, first of all, I try and divide it into two places. Cause I think immediately people think
08:45they want their mentor to be Warren Buffett and like, that's not realistic. And so what I suggest
08:53is that they have a group of what I call aspirational mentors and then, then more realistic,
09:00pragmatic mentors. So the aspirational ones make a list of the people who really stand out in the
09:06field you want to attack and study them and learn from them. You know, it's interesting,
09:11like going way, way back, you might've needed to meet someone for them to mentor you today in this
09:17day and age with YouTube videos and podcasts. Like a lot of these people are out talking about what
09:23they do and you can go like consume all that. And then for, for identifying mentors, you're actually
09:28going to meet with just be more pragmatic. There are people two tiers down from the greats that no
09:34one ever calls, right? Find out who they are. They'll be flattered if you're studying them and
09:40you know, they may not all respond, but you might be surprised. Like 40% of them might say, okay.
09:47And then the last thing I would just say, different mentors can bring you different things. So
09:51you might use one mentor to know about one topic and a different one for another, a leadership or
09:58some particular skill. And so you don't have to, you don't have to have this, this, you know,
10:04Yoda type person who's all knowing. I spoke with Damon John a while back and he talked about this
10:10a little bit and said, you know, being a mentor, like I'd love to give you advice, but don't come
10:16to me and say, I've got this problem. Give me money to fix it. That's not what mentorship is.
10:22Yeah. I think, I think, you know, I mentioned in the book, you need to be nuanced about how you
10:28approach mentors and the types of things you ask for. I think you can't waste a ton of their time.
10:33I think you can't pretend they want to spend three hours at a dinner with you, but if you can
10:38be
10:40efficient with their time, if you can know what they know that you don't, and if you can be very
10:46specific about what you want, like, I think it is okay to say, I've got this tactical problem.
10:51Here are three ideas I have. What's your feedback? By the way, many of the people in the book that
10:56we
10:56profile did this thing where they identified the greats and kind of studied them. Many of them ended
11:03up meeting those people, you know, which is a spectacular moment in their story, right? Where
11:09they're starting to rise. They've studied these people. So when that moment happens, when that
11:16opportunistic chance happens, it's very easy for them to start a conversation because they
11:21know a lot about this individual.
11:23I'm sure you get stopped a lot by people who recognize you. Is there a common question that
11:29is on the mind of a lot of entrepreneurs or people who are trying to pitch you something?
11:35Like, what's the most common thing?
11:36A lot of them are trying to pitch me. So that's probably the most common. I do get asked a
11:41lot
11:41about breaking into venture. And so much so that I developed years ago, I developed like
11:47a five pager that, that I immediately send to people and that explains how the industry
11:54works, explains what the real, you know, avenues of success are and what the work product actually
12:01looks like. Cause I think there's some misperceptions and then gives them a hint at how they might break
12:07in. And so, um, it's interesting. One of the things I do at the end of that letter is I
12:12say,
12:13if you really want to go do this, do these five things and come back to me. And that just
12:18that
12:18little bit of friction, really, there aren't that many people that actually made it to that next step.
12:24What do you say to people now, uh, who are entering, you know, they just graduated college
12:30and it is a, it's, it's a, it's a different time to graduate into college from, uh, people are
12:37struggling to get their foot in the door because they feel like AI has already replaced them.
12:42What do you, what kind of advice do you give to people who are in that struggle right now?
12:45Well, first of all, I would tell them to relax a little bit. I think part of the challenge of
12:50the
12:50modern world is, um, with, uh, with, with no malintent whatsoever, we've developed a philosophy
12:58about how children, what children need to do from age 10 through 22, that is a gauntlet of, uh,
13:08of pressure. And I, you know, and I see people speak out about it. You know, you did the college
13:13entrance process, the re Jonathan Haidt calls it the resume arms race that literally starts
13:20when you're 10, that puts you in a lacrosse class and a cello class and a chess class and
13:26volunteering. And, and it's, I think it's unfortunate because the, the, the kid is so
13:33wired to believe that they have to keep achieving, you know, on this path that they don't ever take
13:40the time to kind of take a deep breath and explore. We used to allow kids to go to college
13:46for two years before we allowed them to pick a major today. You have to, many schools apply to
13:52a major. And I talked to one professor who studied the progression at college. And she says, if you've
13:59taken five courses, she can predict your major within, within, within 98%. And so we just lock
14:07people in. And the truth of the matter is when you look across successful people, many of them are in
14:13a
14:13field far away from their major. And so, you know, and I met, I was at, I was at a
14:18university
14:18yesterday giving a talk and, and a woman came up to me afterwards and said she wanted to switch from
14:24psychology to finance. And she was 22 and she said, is it too late? And I thought, wow, what a
14:30crazy,
14:30like unfortunate mindset to have. And I, and I told her, look, if you transition to like a master's in
14:37finance after an undergrad in psychology, like, do you know how many people study behavioral finance?
14:43Like it's a big thing. Like that could be highly differentiating. Like you might do even better.
14:49And so I, that's my point about relaxing, like just giving people permission. And, and another
14:56reality of this gauntlet, we put these kids in, I think we favored these jobs we view as economically
15:02safe. And as you point out, AI kind of throws a wrench in all of that. I mean, comp sci
15:08went
15:08overnight from being the job where you just can't not get hired to, oh my God, there's a bunch of
15:14unhired, you know, comp sci students. So, um, probably more of a reason to just really explore
15:21and find what you love and don't, don't do something for the wrong reason or for someone else's
15:27reason. And then the last thing I would say, just as a general advice to everyone out there,
15:32lean into AI, like, like it is a tool of the future and know the best way to preserve your
15:39chances in any field, including programming is, is to embrace it and, and to be super powered by it.
15:46I want to ask you, so we've talked a lot about, uh, success. Uh, I want to talk a little
15:51bit about
15:52stumbles or misses. So I've read a lot of interviews with you, uh, and invariably somebody
16:01asks you about Google and your missed opportunity to become an early investor. So I have two questions
16:06about that. When someone brings that up, is there any part of you that is like, you know what? F
16:12off.
16:12I've done a lot of good things too. You always got to bring this up. But then the second part
16:18of that,
16:19what is your approach overall to maybe missteps or mistakes? How do you turn those into a teaching
16:25moment? Do you scream into a pillow? What do you do? Yeah. No, you know, two things about that. No,
16:31I've never been upset by that. In fact, I've often told that story. And I, I think I was,
16:36I benefited quite a bit by having that experience fairly early in my career. So the story is I had
16:45Larry and Sergey present to the partnership when there were 25 employees and failed to chase is
16:51how I like to phrase it. Cause I don't know if we could have won if we chased, but we
16:55failed to chase
16:55it. And, um, it's quite a lesson, right? Like in venture missing something like that is the biggest
17:03kind of mistake you can possibly make. Like investing in something that doesn't work, you lose one times
17:09your money, but here you missed out on opportunity to make 10,000 times your money. And so it's just
17:15much greater. Um, but having lived through that, I think it was motivating. Like, like I'm not going
17:21to let that happen again. Um, there's a, there's a, there's a article that it's not an article. It's
17:27like a piece of writing that, that Tito did Bert beverage again, um, that he gives out to entrepreneurs
17:34about how he tries to channel failure, which gets right at your question, which is he's convinced
17:40himself he can use it as a motivator. And so whenever he misses out or someone doesn't give
17:47him what he wants or whatever, he tries to turn it into fuel. And I think it's just, I think
17:52it's a
17:52really great attitude about the whole thing. It is super important for it. In fact, the final chapter
17:59in the book I titled, it ain't easy. And I take all the people that we profiled their success
18:05and highlight some of the hardships that they went through, because you, you can't have this mindset
18:12that if I hit my very first wall or my very first problem that the, that the quitting is the
18:18answer,
18:18you know, um, Tito says you never lose as long as you don't quit. So, uh, we do a little
18:26segment,
18:27let's call it process junkie for a minute. Um, love to just drill into something that,
18:32that you are really good at. And I think one of the things that you are really good at besides,
18:37you know, making lots of money and investing and all that, you're a really good listener.
18:42Is there a skill that, is that a skill you developed? Do you have a technique to like
18:48turn off all the million thoughts going on in our heads and just listen to what the person in front
18:53of
18:53me is saying? I, I, it's funny you bring that up. I wish I were better at that. Cause I,
18:58I think I have ADD and I, I'm like, I can fall away. Like if something else, um, but I
19:05haven't
19:06noticed, uh, if, if you're thinking about your laundry, I have another, another skill, I think
19:11that I developed over time that I didn't have, you know, writing, I would, I was fairly unsuccessful
19:17in English and writing classes in high school and developed it as a, as a skill later in life
19:24as I read more. And so I would encourage people that like any trait you think you're really bad
19:30at public speaking, people think I'm pretty good at that. Like there was, I had no experience in it,
19:36you know, but I leaned into it and did it more and more. And so like, I'd say anything that
19:41you
19:42think of as a, as a weakness in your, in your personal skills, you can improve. Like I would,
19:49I would encourage you to, and then there's a point. I have another piece of advice I give people
19:54somewhere. I don't know if it's 35, 40, 45, somewhere you should exploit your strengths.
20:00Like I think you early on work on your weaknesses, but at some point, you know, go, go nuts on
20:07your
20:07strengths. Like, like, I don't, I don't think you have to do that forever. I love that. I love that.
20:13I love that. Um, so we have a question of the week and, uh, that subscribers to our newsletter
20:19can answer. Um, anyone can subscribe. It's at info.entrepreneur.com slash HSH. So on a recent
20:27episode, we had an underwater cave explorer on who's done some pretty scary things. Uh, so we asked
20:35people to say, tell us about a time that you voluntarily scared yourself. So my question to
20:41you is when's the last time you did something that absolutely scared the crap out of you?
20:45Well, I will tell you the story that pops in my mind. Um, and, and, and my personal story,
20:52I embedded at the back of the book. So if people want to learn more, it's in there, but I,
20:56um,
20:57I had been a, I'd been an engineer for two years, decided that wasn't my lifelong dream job,
21:04went and got my MBA. But then I went to wall street and I was working on wall street for
21:10three
21:10years, had a successful career, but also came to this conclusion that it wasn't my dream job.
21:16And I was looking for other things. And I, I had one opportunity I was about to take. And then
21:21I got this pretty like crazy opportunity that would put me in Silicon Valley, which is where I wanted
21:28to be to try and become a venture capitalist. And I made this decision working with the gentleman
21:34that, that invited me to come work for him to switch coverage areas. So I had been covering the PC
21:40industry and I decided it would be closer to venture if I covered an industry more emergent. So I decided
21:47to cover the internet, which was almost non-existent at the time, but I picked up coverage of companies
21:52like Netscape and CNET. And, um, the first part of the learning journey, I don't know if you've ever
21:59seen this smile curve of what you really know versus what you think, you know, I was going down,
22:05you know, that first part of learning more, I, the anxiety just went like through the roof because
22:12I was like, why did I walk away from covering this industry where I was considered an expert to this
22:18thing where I know next to nothing. And I was taking meetings and I didn't understand anything.
22:24And, uh, and, and a lot of people, I would say a lot of people, especially going into new careers,
22:30they do well to, to study this smile curve because oftentimes they're just getting smarter, but,
22:37but you don't realize it because you're, you're learning so much so fast. If you're just confirming
22:43your, your imposter syndrome, but, but you'll hit the bottom, you know, keep pushing through is what
22:49I would say. But I, when I think back on my career, that was one moment where I said, oh
22:54shit, well,
22:55you know, what did I get myself into? Yeah. Well, I think it paid off. So it's good. No, it
23:00worked out.
23:01Yeah. Yeah. It worked out. Um, okay. So we got a listener question. This is a little, uh,
23:07a little different. This is from Paul. Uh, does being rich turn people into monsters or does it just
23:16empower monstrous people to do what they wanted to do? That sounds like a loaded question.
23:25Yeah. You know, I, one of the things that the, the, the, the sixth principle in my book is always
23:31give back. And one of the things that I've seen, um, at least among all the people we profile is
23:39an
23:41enormous amount of humility and an enormous amount of respect for the industry and, and an enormous
23:50amount of thankfulness for the people that helped them up along the way. And they all turn around,
23:56you know, and they just started early. Like they don't just start doing this at the very end,
24:01but they start giving back. And part of the reason, you know, I wrote the book was,
24:05was that part of my own journey. And so, you know, we, I, one of my favorite examples of this
24:13is,
24:14uh, you know, a gentleman that most people probably never heard of Mike Leach, who's a famous football
24:19coach, the pirate and his, his win loss ratio wasn't like record setting, but the number of people in
24:27his coaching tree is ginormous. So the point being that he had touched all these people's lives and,
24:35and literally set them free, you know, sharing ideas like didn't hoard anything. And so I, I, I guess
24:44I don't, the, the, the people I profile, at least in the path they took didn't lead to this type
24:50of
24:51megalomania person that the question is defining. Okay. All right. Great. Good. Um, okay. So, uh,
24:59we can wrap things up quickly here with the little speed round. Uh, you tell me, please,
25:07what is a habit that you are happy to have and one that you wish you could ditch?
25:12Um, happy to have, I, I, I became a voracious reader at, uh, later in life. So in, in high
25:22school,
25:22I never read, like never, ever, ever read. And it wasn't until I was about 27. And when I was
25:29at
25:30business school that a bit flipped, I think like most people, um, I, I, I can struggle with, uh,
25:37uh, being productive because, um, maybe that relates to the reading one. Cause I, I, it may
25:43seem odd to me saying that, but I'm so easily distracted by, by learning about something I
25:50don't know. Besides your book to, to reignite maybe someone's lost love of reading or to ignite
25:56it for the first time. What's a book that you think this is a good, this is a good starter.
26:01Um, you know, one that pops in my mind that I think is, uh, remarkably interesting is range
26:09by David Epstein. Um, I'm currently reading Pinker's new book. Um, and I, I recommend
26:16anything that, that Steven, Steven Pinker's done. Um, and, uh, what else might I say? I'm just
26:23looking at, Oh yeah. Um, this one's a bit different. It's, it's for creative is it's really kind
26:29of completely different type of writing, but Rick Rubin's book, the creative way. Um, it's,
26:36it speaks in a different language than most, than most books. Um, but, but you walk away
26:42with very different anecdotes. I love seeing you've got a lot of flagged pages on that. That's
26:48awesome. Uh, and then finally, you're, you're very good at a lot of different things, but what's
26:56one skill has nothing to do with what you do that you were like, man, I wish I was really
27:01good. Oh, this is easy. I am the, the, the, one of, I gotta be a top percentile fan of
27:09music.
27:09It's part of why I'm back in Austin. And I did pick up what you see the Steve Ray Vaughn
27:15in the background. I did pick up a guitar during COVID and I can play a little bit, but, uh,
27:20people encourage me not to sing when, when there's a campfire and, uh, and I, when I watch
27:29people that have this gift, uh, I just would be like, man, if I had that, I just, I would
27:36do it all day long. Uh, you, you and me both, man, I've picked up a guitar about every five
27:44years ever since I can remember my God, I'm so bad at this. Uh, so I totally relate.
27:51Well, Bill, it's been amazing talking to you. Uh, and this book sounds incredible. Thanks
27:57so much for sharing all your thoughts on behalf of everyone who's benefited from your thoughts.
28:01We've got the book coming out February 24th. And what are some other ways people can kind
28:06of keep up with you and know what you're thinking about? Um, I'm pretty prolific on X.
28:11So it's B girly, B G U R L E Y. Um, and I share almost everything going on in
28:18my life there.
28:20All right. Excellent, man. Well, um, I hope there are more books in the future, but I can't read to,
28:25can't wait to read this one running down a dream February 24th. Thank you so much, Dan.
Comments