Raif Ali Dinçkök Student Forum at the Mehrotra Institute - Fireside Chat with Bill Gurley

BU Mehrotra Inst for Business, Markets, & Society · April 2026 · avg confidence 0.74
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  1. [00:00:02] Speaker 7 (0.20) — Louis Salami, Ph.D.: You can just.
  2. [00:35:49] Speaker 8 (0.23) — Right.
  3. [00:00:00] Interviewer 1 (0.29) — Louis Salami, Ph.D.: I'll try to cut it down.
  4. [00:03:59] Bill Gurley (0.31) — Does that sound good?
  5. [01:12:58] Interviewer 1 (0.42) — Thank you so much.
  6. [00:05:44] Interviewer 1 (0.47) — Wow. And so you studied computer science at the University of Florida. Yeah. Played basket…
Interviewer 1Speaker 7Speaker 1Bill GurleySpeaker 8Speaker 5Speaker 2Speaker 4Speaker 6Speaker 3
Interviewer 100:00:00⚠ 0.29
Louis Salami, Ph.D.: I'll try to cut it down.
Speaker 700:00:02⚠ 0.20
Louis Salami, Ph.D.: You can just.
Speaker 100:00:03
Louis Salami, Ph.D.: Okay, let's get started. My name is Louis Salami, and I'm a professor of finance at Boston University. I bring in guest speakers each semester to discuss their careers and provide advice to my students. During COVID, this was impossible to do, and in its place, I would play videos of speeches given by leading finance professionals. I had found Twitter or X to be a great source of information and also keeping me and my class current. During COVID, I actually came across this video that someone had posted of a speech that Bill Gurley had given at the University of Texas in 2018 entitled, "Running Down a Dream: How to Thrive in a Career That You Actually Love." The points made in the talk really resonated with me, and I started playing it in my classes during COVID.
Speaker 100:00:58
My students were so moved by his message that I made it a permanent part of my classes. When Bill announced on Twitter that he was publishing a book about this, I was thrilled. Bill is someone who I've followed on X for years and have embedded a number of his points from his blog, Above the Crowd, in my classes. For me to stand here today introducing Bill as a guest speaker at BU is very special for me. Briefly, by way of background, Bill started his career at CS First Boston as a research analyst covering the tech sector and was a lead analyst on the Amazon IPO. He went on to join Benchmark, one of the premier venture capital firms, in 1999 and later became a general partner. He backed many successful companies, notably Grubhub, OpenTable, Zillow, and famously Uber.
Speaker 100:01:47
Bill was early in understanding the network effects of platform-based companies and how these would lead to unassailable competitive advantages, high returns, and strong cash flow generation. This led to very high returns for his LPs at Benchmark. I would argue that Bill's success in these types of investments explains a lot about the high valuations today afforded in venture capital and high-growth companies. Investors have seen this playbook before and essentially front-loaded, um, all the value creation early on. Another point in Bill's book is to always give back, share information, and mentor others to build a stronger—to build stronger, longer-term professional relationships. Bill wrote this book to help others in their search for a career they love, and it's established a foundation to help people accomplish this. Like everything he does, he is all in on making this book a success and has embarked on a, uh,
Speaker 100:02:44
book tour to promote his ideas behind it. On behalf of the Rafi Y. Dinchak Student Forum and the Mehrotra Inst for Business, Markets, & Society, thank you, Bill, for coming to BU. Thank you.
Bill Gurley00:02:55
That was very kind.
Speaker 700:03:01
Thank you.
Interviewer 100:03:15
Okay, how about that? Let's go. Um, so thank you, Professor Salami, for that wonderful introduction. I think you've done most of my job already. Though we're super pumped to have you here, you recently shared the stage with Malcolm Gladwell, Michael Lewis, and Betsy Cohen, so I'm not sure—I'm not sure how you landed with me. Before we dive in, let me give you a quick roadmap of where we're going with today's discussion. We'll start with your upbringing and your early career path, and move you through your time in the dot-coms and then on to Wall Street, before spending the bulk of our evening on your book, Running Down a Dream, and the principles inside it. However, we're going to do it in a way to minimize any spoilers for our audience tonight.
Interviewer 100:03:52
Can't promise anything, but we're going to try. And then we're going to touch on your career in Silicon Valley and at Benchmark, and then wrap it up with a quick Q&A and a book signing.
Bill Gurley00:03:59⚠ 0.31
Does that sound good?
Interviewer 100:04:00
Perfect. All right, so Bill, I want to take you back to your childhood. You grew up in Dickinson, Texas, and your father was an early employee at NASA. And he literally chased his dream job across the country from Virginia. Can you tell us a bit about your upbringing and the role your father played in shaping how you think about work and ambition?
Bill Gurley00:04:16
Yeah, and some of this is after the fact. In other words, I don't know—I'm analyzing it after it already happened. I don't know that I felt it in the moment. But my father grew up in rural North Carolina and fell in love with gas airplanes, these Cox airplanes that were precursors to drones, I guess. And he went to NC State and got an aeronautical engineering degree because of the love for these things and was working in a wind tunnel at Langley Air Force Base. And these people came through and said—they offered 50 of them—they said, 'We're going to start this thing called NASA in Houston. Would you like to be a part of it?' And he said, 'Yes,' moved from Virginia to Houston. And the thing that I've thought about because, you know, in my career, I've jumped all over the nation.
Bill Gurley00:05:12
And I think it—I never once thought that was weird, but I do think a lot of people get geographically bound by, for good reasons, family and whatnot. And it feels maybe too risky or too scary to kind of jump across the world. And for me, it was never a big deal. And I thank my father for that because I think he kind of set an example of, of the kind of reward you might get by being willing to take a chance.
Interviewer 100:05:44⚠ 0.47
Wow. And so you studied computer science at the University of Florida. Yeah. Played basketball in a D1 program.
Bill Gurley00:05:50
I like to say I practiced basketball.
Interviewer 100:05:53
And three of your teammates went on to the NBA, right?
Bill Gurley00:05:56
They did. Vernon Maxwell, Dwayne Schintzius. Yeah. So what kind of impact did that have on you? I only—I've thought about this after the fact, also. Like, I do think, you know, being around people, and every, kind of, on an everyday basis, and then seeing them go to this next level and being on TV and whatnot, it kind of demystified like how hard that might be, or, or, you know, it kind of gave me a thought like, 'Oh, well, I could go do—I couldn't do it in basketball, but I could go do, do that in another field.' And so I do think it had this weird impact of, of once again just letting me think more things were possible.
Interviewer 100:06:37
I think Michael Lewis describes you as a coach rather than a VC. So do you think it impacted your leadership style?
Bill Gurley00:06:43
I don't know about that. He tried to make a big deal. I don't know if that's true or not. I've never led anything. So I don't know how much of a leader I am. More of a teacher, I would say, is probably better.
Interviewer 100:06:56
Things, right. So your sister was an early employee at Compaq. Yeah. You joined her there after a summer internship. Yeah. At the time, Compaq was one of the hottest startups in the country. Yeah. And you were offered stock options. So what pulled you away after only two years? Yeah. And so this gets into some of the themes in the book. So I had this
Bill Gurley00:07:14
exercise that I developed that I did twice in my career where I—and it's not an everyday reflection, but I said this—I said to myself after a couple years at Compaq, 'Is this something I want to do for the rest of my life?' And so I was in, you know, I, I love computer science, and I think this is one of these things where like, it's okay to wander around. I, I fear that today's young adults have gone through such a gauntlet to get into these colleges, which are so hard to get into, and then to get a degree, that you almost feel like sunk costs against that and that you have to stay in that lane. Many of the people we profile in the book—it's divided in half between stories and tools—they pivoted. You know, some of them pivoted very last minute and into their hobby or into something else.
Bill Gurley00:08:07
And I just—I would really encourage people not to feel stuck with whatever your degree is if it's something that feels grindy to you. So anyway, this idea that I came up with on the fly of, is this something I want to do for the next 30 years? And in both organizations where I made that decision, there were people that were lifers. So I could look at some individual or go talk to them and ask myself, would I be fulfilled if that's what I did? And in both those cases, I decided, no, this isn't what I want to do for the next 30 years. And so I did something different. I went to business school was the first decision that I made. At the time, I fell in love with computer science. I would have thought I'd want to do it the rest of my life.
Bill Gurley00:08:52
What I found as a practicing engineer is we started a third project and it looked like the second project and looked like the first project. These were computer launches. And that part kind of got me bored. And I was starting to play around with understanding the rest of the ecosystem. I was reading the trade magazines. There were software companies, there's all this stuff. And I actually started trading stocks as a hobby, which maybe was a clue, right? I was going home at night reading Peter Lynch, and they had this thing called Value Line back then. This is pre-internet. So they'd send you a ring binder of one-pagers on every company that's out there, and you'd get updates in the mail. That's a really long time ago.
Bill Gurley00:09:36
That's how you would evaluate companies. But anyway, it was exciting to me, that kind of stuff. And so I got drawn into the business world.
Interviewer 100:09:44
And so while you were at McCombs, you said a bit flipped and you fell in love with reading.
Bill Gurley00:09:48
Yeah.
Interviewer 100:09:48
Were there any books that made a considerable impact on you?
Bill Gurley00:09:51
I don't know, if anyone goes to business school, I will tell you that I made a very deliberate decision to go to business school, and therefore I expected a lot out of business school. And I met other people that were just showing up, and I kind of feel like a lot of undergrads, showing up and trying to get the degree and not there to intentionally learn. And when I went back, I wanted to learn about business, and I expected a lot out of it. And I think I got a lot more out of it because it was intentional, if that makes any sense. Like, I wanted to learn the subject matter. I wasn't there—it was, I was on my own nickel at that point. Like, I wasn't there just to get a degree. I was there to achieve something, and so...
Bill Gurley00:10:36
Part of that intentionality led me to start reading for whatever reason. You know, I was one of these kids that just did math all the time and never read. And somehow when I started going to business school, I'd read that one Peter Lynch book, but I just started reading. I made it part of my daily habit. Like I commuted in on a bus and I would read, you know, two chapters on the way in, two chapters on the way out. And I started moving through books really fast. And the rest of my life, I've kept reading in that, in that kind of high-volume manner. But I don't know why I was able to. It's tied into this intentionality thing. I was trying to learn.
Interviewer 100:11:12
And are you reading anything today?
Bill Gurley00:11:13
I'm reading constantly, all the time. Although AI, you know, you kind of just start talking to AI and it's a different journey.
Interviewer 100:11:23
So while you were at McCombs, you became enamored with the idea of venture capital and investing. But you got some pretty discouraging advice about breaking in. What was it, and how did it shape you?
Bill Gurley00:11:32
By the way, not to dodge your question, *Breakneck* by Dan Wang is a really cool book about China. If you haven't read it yet, I'd highly recommend it. I think he spent 20 years in a lot of ways writing the book. It's kind of a lifetime, you know, poured into this thing, a lot of heart and soul. It's well written. Anyway, what was the question? I felt like I had dodged your last question.
Interviewer 100:11:53
So while you were at McCombs, you became enamored with the idea of venture capital and investment. You got some pretty discouraging advice, right, about breaking in? I did. I did.
Bill Gurley00:12:00
So, yeah, I mean, when I had learned about stock options at Compaq, John Doerr was on the board. And then I was really enamored with these software tools by this company, Borland. All these names are really old. But they had some of these visual editors that no one else had. And that company went public and I bought the stock on the IPO. So I'm starting to understand those types of things. My friends and I would go to Vegas and try and count single-deck. And I only bring that up because I think there is a gambling kind of element to venture that was exciting to me. And so, yeah, I, at that time, I was like, "Man, that'd be a really cool thing to do." But I met with a few, I did kind of beg for an informational interview and people told me, "Go work for 20 years and then come back."
Bill Gurley00:12:51
I was like, "Well, that's not a very good piece of advice." Um, and so I, I did, I did something else. I went and became a sell-side analyst. Um, I, I was, when I got to business school, I, it, all the MBA students, I don't know if this still happens today, but we'd sit in the atrium and read Fortune and Forbes and the Wall Street Journal to pretend like we were big-shot executives. And when I read those things, there was a team at Goldman, and I was obviously drawn to the tech articles, who were the key sell-side analysts at the time, and they were always quoted. And I thought, "Man, that's pretty cool. You get to be the voice of of what the right strategy is in this industry." So that's what drew me to Wall Street and that job.
Bill Gurley00:13:37
And this guy telling me there's no way to get into venture.
Interviewer 100:13:41
So you ultimately landed a job with Al Jackson at Credit Suisse First Boston. And your career took off like a rocket ship, right? I got very fortunate. You had an amazing call on Dell. You led Amazon's IPO, beating Goldman and Morgan Stanley. So why did you decide to leave?
Bill Gurley00:13:56
Yeah, so it goes back to this. So three years in, and I remember the night that it happened. So First Boston's research department was on the 36th floor of Park Avenue Plaza at the time, 52nd and Park. And there's four corners to the 36th floor, and they were given to the most senior analysts at the time. And it was about 10 p.m. and I was just needing a break. So I got up and walked the floor of the circle and I stopped in front of each of those four offices and had that same conversation like, "Is this who I want to be? Do I see myself here, you know, 30 years from now?" And the answer was a quick no in this case. Now, I will tell you, being a sell-side analyst is wonderful because you get access to CEOs and CFOs.
Bill Gurley00:14:46
I was like 29 and these people were having to answer my questions, which is crazy. Like this network thing you can do and you're in the paper, you're in the Wall Street Journal, like that's pretty cool. The thing that really started to frustrate me was there's about seven or eight constituents. I used to be able to name them all and they all expected you to optimize for them, and the only way you could really have a good reputation was to piss them all off a little bit and be yourself, but it created a lot of tension, you know? So anyway, that job used to be more idyllic than it is today. The Spitzer Wall happened after I left and the whole thing got a little wonky, but, but it was great. I, I, yeah, and I—
Bill Gurley00:15:38
For people that are going to read the book, I want to make clear the engineer job and that job, I actually loved them while I was doing them. I just reached this point where I said, "I know this isn't what I want to do forever." Jeff Bezos had this framework that you can go watch on YouTube—I'd encourage you to, because it's better coming from him. But when he was at D. E. Shaw, he had this idea that he was going to go start this online bookstore. And he felt very strongly in that calling, but David Shaw was very hard trying to talk him out of that decision. And he came up with what he calls the regret minimization framework, where he said, "What would my 80-year-old self tell me to do here?" And I think it's a similar exercise to the one I was using where you're saying,
Bill Gurley00:16:27
know your lifetime is actually shorter than you perceive it to be and for people your age you know and i remember being your age it feels like you're never going to die like oh this is all going to go you know and i got forever but by the time you're 40 it doesn't feel that way and there's the first word inside the cover here is our first phrase is life is a use it or lose it proposition And so this idea of just making sure, especially if you have the flexibility to do it, that you love showing up every day is extremely important. And we'll get into reasons why I think it's increasingly important in an AI world that you have massive fascination about what you're doing.
Interviewer 100:17:09
And we're going to touch upon that. As we're on this topic of regret, I want to fast forward to your talk in 2018 at your alma mater. You were invited to give a talk to an incoming MBA class, and you decided to speak about thriving in a career you love. Why did you decide to speak about that, and what got you thinking about career regret in the first place?
Bill Gurley00:17:27
There was a period in my life where I was reading a bunch of biographies, and I read these three biographies of people from pretty randomly different fields. And this is very important to me: all fields your parents would tell you not to go into that were wildly successful, and they all started on the bottom rung. So they had no advantage whatsoever, and they were doing similar things. And I used to write a lot of blogs about how the—yeah, how the high-tech world... And so when I saw this through line, I went into the whatever note-taking app I was using at the time and wrote it down as if it were going to be a blog post. And I thought, "Man, if I ever get asked to speak at an MBA program, I'm going to use this." And so it was in the can, if you will, when they asked me to come speak, and I said, "Can I use this thing?" and I dusted it off. So it was kind of
Bill Gurley00:18:16
just random and anecdotal. They posted that speech on YouTube, which you heard about. And in addition to great professors noticing it, James Clear noticed it, who wrote Atomic Habits, and he posted it on his website. And that's when people started pushing me, "Oh, you should turn it into a book." Also, I think I had already started the book, or maybe gotten the first few steps in with the book, when I read this other book called Strength to Strength from Arthur Brooks. And there's no reason for any of you to read that book—it's about when you get to the end of your career, what now? But he talks a lot about—you should use that last stretch to have as much impact as possible. And so,
Bill Gurley00:19:07
A lot of people are surprised I wrote this book. I could have written a book about finance or investing or VCs, but I don't think it would have the potential to impact as much as this one. And so I got very enamored with it. There's also some—this is just a complete aside—with all that reading that I've done, I've gotten really fascinated by great nonfiction writing. That's how I got to know Malcolm and Michael and those kind of things. And I had a co-writer, but I hope we used as many of those techniques as possible. I hope it feels very readable. The stories and the way we wrote them was all very intentional.
Interviewer 100:19:48
To expand on the talk, you distilled its key learnings into principles. What were these principles?
Bill Gurley00:19:57
Well, you know, I don't know if I want to give away everything, but let me start with the first one, which is there's a chapter titled "Chase Your Curiosity." And I just think it's really important. Let me say it a different way. I don't know that everybody can get to that place. And I never intended this to be a book that solves all employment problems in the world or anything like that. What I would say is if you can find a place where continuous learning feels free, you are in a really special place. And the second principle is "hone your craft." So the first one is kind of find what you're fascinated with. The second one is, you need to be a continuous learner. And they're actually a reflection of one another.
Bill Gurley00:20:45
I don't—almost all the stories in here are people that are obsessive learners their whole career. And I love to tell this anecdote that's in the book. Kobe Bryant in 2009 had won four NBA championships and an MVP. That offseason, he calls Hakeem Olajuwon, who's a center, not even his position, and says, "Can I fly to Houston? I want to learn your post moves in the paint." So this is, you know, he's already won all this stuff. He's already as good as, you know, and, and he's coming up with an idea to push it to a, to a new level. And he went down there for two days, there's video online. You can see them working together and he won his fifth championship the next year. That, that kind—these people that I studied have that, like at the end of their career, they're still doing it.
Bill Gurley00:21:32
And I don't think—Angela Duckworth wrote this book, Grit, that says it's 50% passion, 50% perseverance. 10 years later in a podcast, she said, "I should have maybe made it like 80-20 on passion because we've taught a generation of children how to grind through school." But she said perseverance without passion is suffering, which I thought was an interesting choice of word. And so, like, I don't think you can force yourself to be a continuous learner if you have no curiosity or fascination in the subject matter. I think you'll burn out. I think you call it "the conveyor belt" in your book. The thing I'm calling "the conveyor belt" is the unfortunate reality that these schools are so damn hard to get into that in sixth grade,
Bill Gurley00:22:20
You know, your parents start worrying about your resume and Jonathan Haidt called it the "resume arms race." And so you're, you're taking Mandarin lessons and lacrosse lessons and, and, uh, you know, cello lessons and you're, you're volunteering at the SPCA and, you know, and you're in the sixth grade and you're like, "What the hell?" Like, and you're overscheduled beyond belief. And I just, you know, I, and I'm not the only one that—there's a chapter in Jonathan's book, "The Decline of Play." And Rick Rubin has talked about this as well. And there's a belief from a lot of smart people that people don't have the time or the framework to discover what it is that might be something that you're particularly fascinated with.
Bill Gurley00:23:06
I'm working on a TED Talk that I'm going to give next week. I probably should be further along than I am. But I think that people that find this fascination in a lot of ways have what I would call an artisan approach to what they do or artisan mindset. And like that thing I described about Kobe, that's an artisan approach to what you do. And Danny Meyer, who's the first profile in the book, great restaurateur in New York, he's an artisan. If he's opening a new restaurant, he's going to treat it the way an artist would go about doing it. And I think these people exist in every field. I mean, if you have ever worked in an organization with a sales team, there's one person that is the best sales exec in that company.
Bill Gurley00:23:52
And they're an artisan and everyone knows it. Anyone could tell you who they are. And like the way they can get into a room and do what they do, you know? And so I, I think it can, I think it can exist in a lot of places, but you have to, if you don't have that, if you don't have that fascination part—and here's a test I like to use: would you study about it instead of watching Breaking Bad or whatever your favorite streaming series is? Does it compete with your free time? When LLaMA came out, there's a number of technical founders I know that went home and found a Mac Mini that weekend and got it up and running before Monday. They just felt they had to. And by the way, if you think you're a founder and you didn't do that, you really should check in with yourself.
Bill Gurley00:24:42
But that's the kind of thing. Do you feel like you have to know? Are you afraid of someone else knowing before you know the next incremental thing in your field? And you do it for free, right? Yeah, it should feel free. There's this word that books have been written about called flow or flow state. And I think when you are learning about something you're fascinated with, that happens a lot. Like, you don't remember the exercise. You kind of get lost in it. And that's a good test that you're home.
Interviewer 100:25:17
So I'm sure that you've seen firsthand the difference between investors who are passionate and fascinated by the people and products they're investing into. So I'm curious, what actually separates the best investors from generally mediocre investors?
Bill Gurley00:25:30
That's a tough question. I've had a lot of discussions with a lot of people. INTJ is a theory. That's the Myers-Briggs answer to that question. There's a huge difference between a public investor and like a venture capitalist, because a public investor needs no social skills whatsoever. In fact, some of them might be very spectrum-y.
Interviewer 100:25:55
In a—we just had Alex Sacerdote.
Bill Gurley00:25:58
Was he spectrum-y? In venture, you have to go win deals. You have to show up and present yourself and convince someone. You have to sell, sell, sell, sell. There's zero selling in the public markets. You buy the stock, you get rid of the stock. And so anyway, there's multiple dimensions depending on the type of investing that's out there. I do think—I'll tell you this, especially for a crowd of young people—I have found that certain people, their brain is structured in such a way, maybe ADHD, which people have accused me of having, where you want to think about a broad set of things, you know, and where you're intrigued by a broad set of things, and jobs that are service provider jobs, which can include investing or consulting or investment banking.
Bill Gurley00:26:54
You get to play in a lot of different things. And I told that story about how the project cycle at a product company felt slow to me. And so getting in touch with—and, by the way, I've met the opposite. I met people who say, 'How could you be a VC? You guys don't do anything. Why, how could you even want to be that person? The founders do all the work.' Okay, I'm fine with that, like, but I get joy out of showing up and doing it. So, but, and I'm not, I'm not being critical of either of those things, but getting in touch with which one's the right fit for you, I think, is valuable. Okay, so I know we said we're not going to spoil the book—
Interviewer 100:27:32
We can spoil it. We already got a copy. I'm going to spoil the talk. There's a profile that really stood out to me: Bob Dylan. I think his story is not only incredibly inspiring, but just, for lack of a better word, ballsy. What did you want the audience to take from the story?
Bill Gurley00:27:52
There's a couple of things about Dylan that most people don't know. Unfortunately, the movie didn't touch on either of these things. Well, it touched on one of them. I think Scorsese in the documentary called him a musical expeditionary. He's so studious about music, initially in the folk sector. Like when he left Minneapolis, he knew he had listened to more folk records than anyone else in the state. I'm convinced of it. And he used to go into the record store—back then they had booths—and would just cycle through every single thing. But he, he oddly did a podcast series a few years ago where you can go check it out, but like his knowledge of songs well outside of any genre or anything he did, it's clear that he's a student, a lifetime student, which gets back to this. Yeah, and then he, he hitchhiked with ten dollars to New York to meet Woody Guthrie, which is probably
Bill Gurley00:28:52
The most ballsy mentor pursuit story that I know of. Bobby Knight comes close just in terms of the gumption to try and meet, but he literally hitchhiked to New York to meet Woody Guthrie.
Interviewer 100:29:07
He hitchhiked over a thousand miles, right? Yeah. So for many of us here, what advice do you have for finding and reaching out to our mentors?
Bill Gurley00:29:14
I probably wouldn't recommend doing what Bob Dylan did. Here's where I've come down on mentors. And I borrowed this from Danny Meyer. I think you should set aspirational mentors. And by the way, it's never been easier in the history of the world to learn than right now. And it's kind of on an exponential curve. So if you want to go know about something with AI, this is crazy. You are so fortunate to be able to learn at this speed. But what I would create—Danny created a list of 10 people that were impressive to him in the restaurant industry when he set out on his journey. Create a little notebook for each one of them. Like, you, you know, imagine you're a fanboy of a particular, you know, basketball player or something. Think about it that way and keep notes on them. There's, there's videos of interviews on YouTube, there's podcasts that they've been on, and just study them. If there's a book that they've written, study them. And, and don't try and cold call them when you're at the very bottom rung, because they're going to think you're weird and it's not going to work.
Bill Gurley00:30:27
I mean, I've called and emailed you, so. Yeah, and then, yeah, and whatever you do in the first meeting, don't say, well, you'd be my lifetime mentor. That'll get you to know fast. But I think if you just look a couple rungs above you on the ladder instead of all the way to the top, you might find people that have never been asked to be a mentor before that know a lot more than you do, that are flattered that you found them, flattered that you acknowledge that they're worthy of such a thing, and they're going to take it way more seriously. And of course, you want to build mentors in different areas and different fields, so you're going to get a few of these. You know, be super ambitious for these aspirational mentors you might meet them one day Danny ended up meeting all 10 of them, which I thought was really cool.
Bill Gurley00:31:15
And, by the way, if you do meet them, if you've been studying them for five years, you're gonna, you're gonna do so much better in that meeting, like, because you're going to know so much about them, like, you're going to prove... And then, and then don't reach as high for the others. I don't know why this wasn't in Do Not Disturb. There we go. It's my wife. Don't tell her.
Interviewer 100:31:35
So you have a phrase at Benchmark that you often repeat: "Good judgment comes from experience, and experience comes from bad judgment." Yeah. So how important a mentor has been in your own story?
Bill Gurley00:31:48
Well, I think that's the main reason you want mentors. So I don't know if you heard what he said. We had a phrase, 'Good judgment comes from experience, which comes from bad judgment.' And if you can, if you learn it through bad judgment, it'll stick harder. So that's good. But you don't want to learn every life lesson that way. It would be a little painful. So if you can meet people who've been there and done that, that's one of the main things they can keep you from doing is making mistakes that other people have already made before. Right.
Interviewer 100:32:18
So Dylan's story also speaks to Principle Five: go where the action is.
Bill Gurley00:32:22
Yes.
Interviewer 100:32:22
How important are our physical surroundings and the power of serendipity in our careers?
Bill Gurley00:32:26
So in the original video that was mentioned, this one wasn't in there, so we added the sixth bonus principle, uh, to the book. And a lot of people pushed me to put this in there, and then I was resistant at first. And now that the book's out, I'll tell you, I get more positive feedback about that chapter than any of the others. Mine—my favorite is probably the peer one, which we can talk about, but, um, yeah, if you can afford it, and if you're convinced you know your fascination area, and if there is a place on the planet where there's an epicenter for that thing, you should try and get there. And I, the more I've written about it and talked about it and thought about it, the more kind of convinced I am of this.
Bill Gurley00:33:18
And the main reason is all the other principles get easier. So constant learning, finding peers, finding mentors, they're, they're all 10 times easier if you're in this place where everyone's doing the same thing. And then, probably the bigger thing, which you mentioned, is serendipity. So if you read any or if you talk to any successful person, they're going to have two or three stories that sound like obnoxious luck: 'Oh, and then this happened, and this happened. And how could that have possibly happened?' And I had several of those. But if you're there, if you're in that place, the optionality goes up so much. You know, there's this phrase that luck is where preparation meets opportunity.
Bill Gurley00:34:01
The number of opportunities you're going to get if you're in Silicon Valley and you care about tech or entrepreneurism—there's an event you can go to every night if you want to and meet another person. There's so much going on. Same thing if you're a songwriter in Nashville and the number of people that can help you. And the reason people don't do it is they have this thought that they'd rather be a big fish in a small pond. I think that's just completely false. Like, even if you're going to do that, go to the epicenter for a while and then go to the small pond that you seem to like. And then the other reason they don't is they fear the competition. And this kind of relates to the peer chapter, too, but I think people—there's this great book called Finite and Infinite Games.
Bill Gurley00:34:50
And, and most of life is an infinite game. There's no winner. There's no end to the clock. And, and we build a lot of our strategies around finite games where there's only one winner. And what I would just say is, in any one of these career fields, there's tons of winners. Like, get over needing to be the very top dog or whatever, and you'll enjoy life a lot more. But that's the reason—like, that's not a reason not to go to the epicenter. Like, it's not—it's okay. There's more job opportunities. There's more learning opportunities, more everything. Like, you won't regret it.
Interviewer 100:35:25
Go where the action is.
Bill Gurley00:35:26
No doubt, if you can. It's also a reason—one piece of advice I'd give to young people: try not to get financially trapped too early. Like, the more flexibility you have, you know, in that first job, don't spend 120% of your salary. That's a real mistake because it limits what you can do, both from a career-shifting standpoint and a geography-shifting standpoint.
Speaker 800:35:49⚠ 0.23
Right.
Bill Gurley00:35:51
It happens, especially in New York. You go to New York, people tell you you've got to have Hermès ties and you've got to have a place in the Hamptons. You've got to have a membership at the Racquet Club. You can get stuck fast in New York.
Interviewer 100:36:04
So Dylan went on to inspire actually once-in-a-generation entrepreneur, Steve Jobs. And while you were at Benchmark, you backed some incredible founders, Rich Barton, Katrina Lake, Travis Kalanick, very different personalities and very different companies. Is there a pattern you keep seeing in the founders that went all the way?
Bill Gurley00:36:22
I'll tell you the—well, I'll give you two parts to that answer. One, I'm going to borrow from Bezos. I asked Bezos once, "How do you have this incredible angel portfolio? You're so busy with running Amazon." And it just seemed implausible that you could occasionally talk to founders and do Google and Uber and all this stuff. And he said, "I only look for one thing." He said, "I want to see a level of determination that, like, dog on a bone, this person's going to do this no matter what. Like, whether it takes my money or not, like, he wants to feel this kind of, like, force coming out of this individual." I think that's a good test. A lot of people, I think, make a mistake of saying, "I'm going to be a founder."
Bill Gurley00:37:12
And then they start looking for an idea. The odds that you're going to come up with your life dream company through that process seems low to me. So, anyway, that's one thing. And then, you know, you said go all the way. There was an interesting chapter or there was an interesting blog post written by the team at Andreessen Horowitz where they said every VC wants, they, as a firm, want to back founders that go all the way. And the truth of the matter is every VC wants to because a CEO search can have like a 50-50 probability of working. So why would you put a 50% chance on any one of your startups? But buried deep in that blog post they wrote, I think Ben said, of course, they have to want to become a leader.
Bill Gurley00:38:01
And we make a mistake, I think, just as an industry. First of all, there's a lot of VCs that are positioning themselves for deal flow. So a lot of what you hear is marketing, but whatever. We don't talk much about what it would take. If your company goes from 10 employees to 100 to 1,000 to 10,000, you need leadership skills. And there used to be this amazing guy, Bill Campbell, in Silicon Valley that was this kind of secret weapon that John Doerr and Moritz and others were using. He was still running the Google management team meeting 10 years after they went public. no one knows this bill campbell was you know eric schmidt gets all the credit but like it was it was bill campbell anyway he taught a lot of of the best founders in silicon valley how to lead but but there's no reason that a founder would be innately born with the skills it takes to lead 10 000 people it's a hard task are there any founders that have made that transition successfully
Bill Gurley00:39:09
I mean, I think a lot of people would give Zuckerberg credit for that, especially with some of the hard calls he's made in the past five years. I mean, Elon's clearly made that. Bezos made that transition. Michael Dell kind of went in and out and kind of and came back in, but clearly, you know, at 60, he's still running the thing and and doing just fine, and it's pivoted through a couple of tech transitions that most people in that field would have missed. So, yeah, there are, there are people that have done it. Um, so you mentioned that your favorite—and they'd be great people to interview on that question, like, how do you, how did you learn to be a leader? It's not, it's not, it's not trivial.
Interviewer 100:39:54
And so what advice do you have for any future founders in the audience today, especially with all this VC money? It's crazy out there.
Bill Gurley00:40:01
That's what I would say. It's not your father's venture capital world. I'm perplexed at how much money is flowing around. And the game has changed dramatically. The majority of venture capital is delivered via preemptive rounds, which means the money is being inserted into the companies. The companies aren't going out looking for the money. It seems a little backwards to me. But there are a number of players that have convinced themselves that that's the right way to play the model, and they've got access to enormous amounts of capital, and that's what's happening. I mean, if you look at—I'll just use two examples. If you look at AI coding companies and AI legal companies like Harvey AI.
Bill Gurley00:40:52
There's seven venture backed companies with over 300 million each in each of those categories. So I've had I had a young person come up to me and say, I'd like to do something in legal with AI. I'm like, are you kidding yourself? Like how in the world are you going to go compete with that? And that money will land somewhere. So they're, they're going to be in a knockdown drag out fight to win accounts. And that's either going to represent itself in a very aggressive go to market effort, which means salespeople and marketing materials and that kind of thing, or It's going to land in discounted unit economics. And I think you probably get a combination of the both. And both those things make that space very dangerous and difficult.
Bill Gurley00:41:41
I lived through a version of this with the Uber-Lyft wars, because Lyft was able to raise billions also. But now we're going to go run that experiment in every venture category whatsoever. And so it's tough. I used to give this piece of advice, which I still stand behind. If you take venture capital as a founder, you're very likely to not just do an A, but do an A and a B, a C and a D. And before you know it, you're going to own less than 10% of this thing. And the number one type of acquisition companies prefer to do are tuck-ins in the 20 to 100 million range. They don't have—they don't have to get regulatory approval. They like buying tech teams. They like buying product features. So if you can bootstrap, you could sell a company for $30 million that you own 100% of.
Bill Gurley00:42:30
That's lifetime wealth. If you start taking venture capital and you own 10%, obviously now to get the same $30 million, you've got to sell for $300 million. And as those numbers get bigger, the odds of pulling off that transaction go down materially. So I just like, you know, someone asked me a question earlier today, "Who needs venture capital because you can just have a bunch of agentic bots and you don't need employees?" I'm like, "Great, bootstrap." Like, maybe it's an even better time to bootstrap. But the venture game has gotten so industrialized that 10% may become 5%. And the odds of success is partially caught up in this chaos, cash-arsenal game, you know, I call it a sport of kings that you're going to be forced to play in, and it's—it's going to be messy. I want to get back to the—and there's different types of ideas that I think are, you know, smaller scale and better for bootstrappers and all those things, but anyway, get back to this. I want to get back to the book. So, you mentioned it earlier,
Interviewer 100:43:32
Your favorite principle is Principle Four, "Embrace Your Peers."
Bill Gurley00:43:34
Yes.
Interviewer 100:43:35
Why does it resonate with you so personally, and how important have peer networks been to you in your journey?
Bill Gurley00:43:41
Yeah, so the principle is called Embrace Your Peers, and it starts... Well, I won't steal that. I'll use a different... But the... There is immense value you can get out of finding a group of like-minded people that are on the same journey you're on, preferably outside of the company you're in. And if you can connect with a group like that and get on a Signal group or a WhatsApp group and share ideas, share your network, you'll help accelerate everything. So instead of learning just at the speed of whatever you can read, you get to learn with this other group of people that are out there doing the same thing. Um, if you need a connection, it's not just your network, but it's the network of this whole entity that's out there. If you're having a bad day and you're a little—you need a pick-me-up, this—these people will be better than mentors because you might be—well, you might not want to be vulnerable in front of a mentor. Job opportunities could come through this kind of thing.
Bill Gurley00:44:44
And there's a couple of examples in the book. There's a whole chapter about these athletic directors that were all very early inside of an athletics program. And they met at a conference and started a text chat together. And they're now, 20 years later, eight of them are all D1 athletic directors, all eight of—and their journey of co-learning got to the point where they were doing either once a year or twice a year off-sites themselves, bringing their family along and scheduling speakers to come in and talk. And—and there's actually another element, too, which I realized came in other parts of my life, but you push each other in a very positive way. Like, if you see other people being successful, you want to be successful. Like, there's a bit of peer—peer pressure. Peer pressure sounds negative. There's a
Bill Gurley00:45:41
positive version of peer pressure that lifts everybody up.
Interviewer 100:45:45
And as a VC, I can imagine you've often found yourself competing for deals, for talent, for capital. How do you strike that balance between collaboration and competition?
Bill Gurley00:45:54
I think the number one reason people don't do this is they get overly kind of enamored with competition. But I go back to that Finite and Infinite Games. Like, there's going to be—all eight of these guys are D1 athletic directors. It's okay. They didn't get the same job as the other person, but they all won. And I think they probably had more fun doing it. And there's an article you can find online where the NCAA got worried that they had too much power because they all knew each other. So if you end up at that place, that's a pretty good place to be, right? And I think there are people that are sharp-elbowed. I think the odds that you have some unique thought in your brain that's going to stand the test of time and differentiate you forever is just false, man. We live in the day and age of AI. Like, ideas last a very short period of time. Like, I just wouldn't get caught up in the notion that you're that special. Um, and, and, and—
Bill Gurley00:46:51
If you met sharp-elbowed people, no one likes them. I remember when I was at Compaq, we had some of these pieces of equipment that were really expensive, the logic analyzers and stuff. They're not going to buy a bunch of them. So you had to rotate on them. And people would hoard them. And I knew who those people were. I'm still mad at them. But they're not the type of people you want in your group. Kick those out of your group.
Interviewer 100:47:16
Right. And is there a story where you were shocked someone was helping you?
Bill Gurley00:47:21
I would answer that question by telling you that there's something remarkably unique and special about Silicon Valley where it is very easy to ask for help. And a lot of people say yes. And I don't—it'd be interesting to hire an anthropologist to try and understand why it's that way. But I've talked to a lot of people who have experienced it. And you could ask anyone who's been there. It's just remarkable how easy it is to get people to give you advice and help. And that's pretty special. So, like, the whole community did is my answer to your question. And there was a... watched a documentary on songwriters in Nashville, and they made that same point that, like, if you show up in Nashville, you're serious about songwriting, like, within a few months you might meet someone who has a Grammy, you know, and they're going to take the time and help you. There's a kind of a collaborative mindset about the art. Again, it goes back to that artisan work.
Bill Gurley00:48:24
Like, if you take it seriously and show up, people are... It may be in Silicon Valley, there's just so many people moving between so many companies. And it may be also that so many people have experienced it on the way up that they now feel a responsibility to do it, but it's certainly part of the culture.
Interviewer 100:48:42
And I think that speaks to the last principle, Always Give Back. And you started the chapter with this really beautiful quote from Picasso about the meaning and purpose of life. Why you decide to anchor the chapter with this quote?
Bill Gurley00:48:54
I think I realized, not at the very beginning of my career, but about halfway through, that if you start acting with a kind of give-back mindset earlier, a lot of good things happen. And I think you feel better about yourself, but I don't think that's the reason to do it. And I also think it helps you with all these other things, connections and whatnot, by behaving that way. But it's remarkable. And I have a ton of examples of how it works. I think... It's really interesting. I talk briefly in the book about one of my favorite people who unfortunately passed away was Mike Leach, who was this crazy—he called himself the Pirate—crazy football coach, and he really... He innovated in a way that changed the entire game.
Bill Gurley00:49:47
Now, he never got to the point where he won championships, but he has this coaching tree. And at his funeral service, they were talking about this. The number of people that have been impacted by Mike Leach is this huge set of NFL coaches and NCAA coaches. And he was a character, which is part of why I loved him. But like, that's a pretty cool way to measure success in a field is how many people did you end up touching? And I, as I've met with young people—a lot of people, this modern youth, I don't fully understand, but a lot of them stood up and they say, 'Yeah, I don't care about any of that. All I care about is purpose and impact.' And I said, 'Okay.' And yeah, they asked me about the book, and I said, 'Well, in each one of these profiles, each one of these cases, these people get to a point in their career where it's not just about them. They've impacted so many other people.' And I like Danny Meyer. So Danny Meyer's a restaurateur in New York. He's probably started a dozen or so of the best high-end restaurants in New York, and then he did Shake Shack, and then he wrote this book, Setting the Table, which I'm sure 80% of restaurateurs have read. So if you look at
Bill Gurley00:51:04
Like, if you ever meet a chef that worked at a Danny Meyer restaurant, they wear it, like, on their sleeve. Like, that's part of their resume they're most proud of. And then he's probably served millions of customers with his hospitality. And in the book, like, you end up, if you can get in this lane and live this way, your impact's pretty big, like the footprint you leave in the sand.
Interviewer 100:51:27
So towards the end of the book, you announced the Running Down a Dream Foundation. Yes. Can you tell us what you hope is a long-term impact of the book and foundation?
Bill Gurley00:51:34
So let me tell you about the foundation. So this was an idea I had kind of as I got to the end of the book, and the last page of the book talks about it, so you can read. But this hasn't happened yet. So it's going to be an experiment. I'm going to give away 5,000 micro-grants. We're going to have an application process, and all the proceeds of the book are going into this and more. I put more in there. So we're going to have an application process for people that want to chase their dreams and might be stuck a little bit financially. They might use it for, you know, there's a couple of people in the book that just did an entry-level trade school. You know, Danny Meyer went to this restaurant management course.
Bill Gurley00:52:15
He worked for free. Yeah, you did do that too. But Jen Atkin, which is a story we haven't talked about, she wanted to be a hairstylist. The only course she could afford was a cosmetology class offered by the City of Los Angeles for free. And she went and did that. So anyway, it might be something like that. It might be paying off debt. I don't know. We're going to see once we get into the application process. But a couple of people have poked me: 'What if you're really stuck?' And so hopefully this will be a way to deal with that. We'll see.
Interviewer 100:52:46
so bill with a couple of minutes left i i want to pivot to your time in silicon valley and at benchmark so you spent over a quarter of a century there as a partner and benchmark today is one of the most prominent vcs in the valley feedback some iconic companies instagram snapchat twitter and your personal home run uber however and i hate to do this there's one that you missed google i didn't tell us about that and this is how you're gonna say something else um
Bill Gurley00:53:13
Yeah, so shortly after I got into venture, maybe two or three years at Benchmark, I, like many people, started playing around with Google Search. It was clearly better. And I found a way to get in front of Larry and Sergey, went over and met with them. They had 25 employees, and I got them to show up and present at Benchmark. They presented. It was, uh, it's kind of an interesting presentation, um, and in the follow-up, we failed to chase the company. And those are important words. It's not like—I can't prove that if we had put an offer down, we would have won. So somebody would say, 'I passed.' I did—passing is the wrong word. We failed to pursue the company, and John Doerr, Mike Moritz did. And in venture, there's this thing that I call asymmetric risk, where you can lose one time your money, but you can miss out on something that might be 10,000 times your money, which is what I did in that case.
Bill Gurley00:54:18
And that's the error you need to worry about, not the first error. And after that happened, we kind of reoriented everything we did at Benchmark to analyzing coverage and misses, and why did we miss something, and focus entirely on that versus did somebody make an investment that went to zero? Those things are going to happen. What's really important is not missing the home runs. And maybe if I had done that, I'd have wrote this book 15 years ago and retired. I don't know. Maybe I was motivated by the miss to keep trying. I don't know. But yeah, it's interesting.
Interviewer 100:55:01
So, Benchmark is famously structured as an equal partnership. Does that give you a leg up over a Sequoia or a Thrive when you're winning deals?
Bill Gurley00:55:09
I think that, um, venture, both from an individual standpoint and from a firm standpoint, it's been proven that there's a lot of different approaches that work and people from a lot of different backgrounds. Sequoia is probably the most successful venture firm ever in their hierarchical structure. And we were an equal partnership. As a youngster coming in, I was so fortunate to be part of an equal partnership structure because I show up and on day one, I have equal weight with all these people. And even more important than that, which wouldn't be obvious from the structure, but because they've committed to me, the best thing they can do for their own financial interest is make sure I'm the most successful I can possibly be.
Bill Gurley00:55:55
Because when I end up eventually doing Uber, they split that equally. And so the... clear incentive for them to develop me is high. In an, in an up-or-out firm, they just let you kind of fight with each other and see who's better, and so it's a different dynamic. Clearly, so it worked out really well for me. I wouldn't say better than anyone else; there are scenarios where it's better. We were horrible at any initiative whatsoever—that's why the website is just a splash page today, um, because we don't have a CEO, so we couldn't delegate, and so we just didn't do much other than practice the art of venture. And, and, and if you believe that in order to be successful you have to scale up, I think Andreessen Horowitz has 15 times the number of employees that we do.
Bill Gurley00:56:46
So if you believe that's necessary in the modern age, then it would be a handicap. It's very hard to scale that. In fact, we tried to do international and it didn't really work. But anyway, so...
Interviewer 100:57:01
So, Bill, before we wrap up, do you have any advice for people here who are worried that AI...
Bill Gurley00:57:05
I do. I wrote a whole book about it. No, no, no. That AI might replace them. Oh, AI. Yeah. So I've thought about this a lot. And I started the book way before LLMs and AI. What I've come to believe is that if you're high-agency and fascinated with something, you've already been using AI like crazy. And I think the number one way to protect yourself against AI is to be the most AI-enabled version of yourself you can possibly be. There's this famous story that I love. Bjorn Borg, famous tennis player, retired early at like 33 or 31—or I'll get the age not right specifically—but five years later, he tried to make a comeback. While he was gone, the world had switched from wooden, small-headed rackets to these big-headed graphite rackets.
Bill Gurley00:58:00
And he insisted on making the comeback with the old rackets. And in fact, he had to pay someone to build them because no one made them anymore. And he got slaughtered. And anthropologists say humans evolve with their tools. And so if you're not using AI, you're not... There are other humans that are. You're a sitting duck. Like, you're dead. And I also think the fascination part helps because you're immensely curious and you're on the edge. If you've learned a bunch of algorithms that they taught you in school and you stop learning and you just think you're going to get paid to use those algorithms, those are the ones in the model. Like, those are the ones that went—that best practice went in the model first.
Bill Gurley00:58:45
And so you need to be on the edge. And the only way to be on the edge is to have this artisan mindset and be fascinated and be on the edge. And so I didn't intend for it to be that way, but I'll tell you one thing I could say that might be somewhat scary. It could lead to more separation. These people that I'm describing might get further ahead of everybody else. And so it could—this inequality thing could be a real problem. But if you're thinking about it from an individualist standpoint, like being there, if there are 30 people that do what you do at a job and you're the one that uses AI the most and knows the most about how AI will play in that role, you're not getting fired. The others I can't speak to, but you're not getting fired.
Interviewer 100:59:31
So, Bill, with that, thank you so much for coming and sharing your views. We're going to take questions.
Bill Gurley00:59:38
Yes. While we're figuring out questions, I will say something about the book signing, which I'm thrilled to do. Um, someone had suggested handing out these yellow notes. If you put a name on it, I'll write to your name. Don't write like sentences, 'cause I can't get through everybody. I had that happen and it created a problem. So I'm sorry, I can't write like a paragraph. You're in charge. Okay. I hate being the one that chooses, so why don't you choose? I feel horrible.
Speaker 501:00:18
Hey, Bill. Thank you for being here with us today. I want to ask you about one specific investment that you made. You invested in the company named Mercor. Yes. Series A, 2024. The company exists for a year and is founded by two undergrads, Harvard dropouts, and is valued at $220 million.
Bill Gurley01:00:39
Yeah, so can you please tell us, how do this type of deals come up on your radar, and what's your decision-making process? Yeah, and keep in mind that deal was closed after I stopped making new investments, so I'm, I'm intensely aware of this particular company, so I can answer the question, but I'm no longer in that decision-making, the group at Benchmark. Um, the founder is, and this was true at WeWork as well, the founder is remarkably ambitious and aggressive, and it's something you can sense within 10 minutes, and you would too. And that's allowed, and the momentum, the business momentum was there from the very beginning. Um, the world has shifted. Part of the answer to your question is what we, I was talking about earlier about how intensified the venture business is. A number of very successful venture capitalists have come to believe in network effects and power laws, and they're willing to make bigger bets from a dollar perspective and a valuation perspective,
Bill Gurley01:01:44
with the belief that they'll eventually earn into these things. And I think you mentioned Thrive. I was just with Vince, one of the Thrive partners, at a talk like this at lunch. So I know them well. But Thrive has decided that they're going to give money to all these companies that were IPO candidates and almost take the price. Tell the founder, 'What price will you give us? And we'll pay it.' And there's a great Fortune article about them where you get a sense of some of that. So it's a different world out there. The market sets price. And most venture capitalists come to believe over decades that being price-disciplined is a really dangerous game for the reason I had talked about, which is the biggest thing you can
Bill Gurley01:02:31
error you can make is not being in the one that goes all the way. And so there's just a lot of, I know that sounds crazy that you get put into a job where your job is to invest millions of dollars on behalf of other people and then you aren't price-disciplined. But you're really, the market, you're kind of a price taker in the market. And the venture world's only gotten more competitive from the day I joined to today. And so that makes that even more so like, um, yeah, that's a, that's a long answer to your question.
Speaker 201:03:09
Bill, I just want to say thank you for coming. I have a quick question. A fellow venture capitalist a couple weeks ago went viral, Marc Andreessen, for saying that he does no introspection at all. About your reflection at companies of asking yourself whether or not you want to be here in 30 years, how do you balance sort of his point of view with, with yours? I don't know what his point was. He took a lot of heat for that because it sounded amoral, I think, um.
Bill Gurley01:03:36
And him and I have gone back and forth over the years, so I probably don't want to get tempted into that. Yeah, I don't know. It sounds weird. My brain doesn't work that way. I'm constantly reevaluating everything. I understand the concept, I guess, like rumination can lead to anxiety and that can freeze you. And moving fast really matters, especially like when these disruptions happen, like what's happening with AI, like moving slowly is really dangerous, really, really dangerous. So maybe that's where there'd be common ground. I do think speed matters.
Speaker 701:04:19
I'll speak up. Yeah, that's fine. Given the competitive nature of VC today, if you were a student or recent alum, you're trying to break in, how would you do it?
Bill Gurley01:04:28
So, um, this question came up while I was on this trip, and for 15 years, for reasons I can't fully explain, I had this letter that's titled, 'So You Want to Be a VC?' It's a three-page PDF, and when someone would email me and say they want to break in, I would send them this letter. Today, I posted it on Twitter, so I don't know why I decided, 'Okay, now it's okay to...' So you can go look on my Twitter handle, and you'll see there's a three-page paper. And I reread it before I posted it. It's held up pretty well. So make sure you want to be in it. It may not be what you think. You're selling constantly. It's 80% of the job. If you don't like to sell, I wouldn't do it. There are more venture capitalists in the world than the world needs.
Bill Gurley01:05:15
And I doubt you'll get a job as a venture capitalist by going to the career center and asking them who's applying, who's posting job opportunities for venture capitalists. You're going to have to create a situation where you're a candidate of one. You're going to have to, like, present yourself into a job rather than find someone that's hiring. And I get in deeper about how you might go about doing that. By the way, I think that's the best way to get any job is to be able to do something like that. Very different to differentiate yourself by kind of making yourself available and to where someone wants you rather than getting, like... Part of why I wrote this book—I haven't said this out loud, don't, don't repeat it—but I, I... That the idea of the career center as a way to find your dream job is just baffling to me. Like, the odds that the company that you desperately want to work for is interviewing at your school for the job you want, it is near zero. So it'd be... It's just a weird place to go find your next career spot. Don't tell them I said.
Bill Gurley01:06:28
Oh, shit. They got a job to do. I kind of understand it. You can't mass manufacture. It'd be hard for them to help everyone do a custom, bespoke job journey. It's impossible. Yeah.
Speaker 401:06:44
Hi, Bill. Thanks for being here. I'm in venture myself. And you mentioned that you're always re-evaluating things. Um, what's something you believed was true about venture capital for, let's say, the last 20 years, but you recently changed your mind on? Um,
Bill Gurley01:07:09
That happens a lot. I would tell you one of the reasons why I think that a partnership structure works well in venture is there's this saying, strong opinions loosely held. You have these mental models, but if you have too many of them, you're going to end up missing a Google. Something's going to click and tell you to get to know. And a group can kind of help decide where you might need to relax one. There was a belief in venture 15 years ago that it's too hard to get to small business. You don't want to sell to small business. And most VCs wouldn't look at deals. And that's one of the reasons why Toby at Shopify got so many no's when he went up and down. sand hill road or don't fund a company in vancouver well okay now you got two reasons you're passing on shopify which is one of the most successful companies and toby's turned out to be one of the most genuine unique like if you ever
Bill Gurley01:08:09
If you ever hear he's doing a podcast, just drop what you're doing and listen to it. The guy is so special. But you have to constantly change your priors. And I think you'll see in this letter that I wrote that I think venture capital bends towards youth. And I've always felt that way. When you get older, you get cynical and you build all these mental models. They're all traps. And there's a bit of naive optimism that is going to be very—that where the young person who will take that flyer that the old person who won't have the guts to do anymore, yeah.
Speaker 601:08:46
Hi, Bill. Thank you for your presentation. So, I'm a freshman, and I was really, like, inspired by, like, the aspect of, like, finding your fascination, but I feel like every single time I try something new, I'm always burned out by, like, everything. So, advice, like, other than just keep trying, because I feel like I do want to find something that I'm fascinated by, but it's like...
Bill Gurley01:09:05
Yeah, I mean, I would read through the first chapter because I borrowed exercises from all the people that had come before me—so, stuff from Designing Your Life. There's other books that talk about different strategies for this. But I love—Angela Duckworth has a phrase, "wander with purpose." So just keep moving. When I got into being an engineer, when I got into Wall Street, I did have that—that affection, and it just burned out. It was fine. Like, be flexible, move around. There's other techniques. The—the guys that started the Acquired podcast, one of them had this—this notion where they did a side hustle in all their jobs, which was kind of interesting because when he presented it to the companies, they all viewed it as very ambitious and thoughtful that he was doing this thing.
Bill Gurley01:09:56
And so at Microsoft, he asked them if he could help get the company closer to entrepreneurs. That ended up becoming something called Microsoft Garage. Through that, he met a bunch of venture capitalists who asked him to come work at Madrona, which he did. While he was there, he said, "Can I do a side hustle as a podcast for Madrona?" They said, "Sure." That became Acquired. It's probably the highest-revenue podcast in the world right now. Him and his co-founder are living the dream. They are so tickled-pink happy every time I see them. They love what they do. Michael Lewis sat down with them recently, which is cool to listen to. So they found their way there. And just keep searching. I wouldn't force it.
Bill Gurley01:10:39
I would just keep looking, keep looking. One exercise, especially when you're young: whenever you're around a big group of adults and you don't know what to ask them, say, "What do you do for a living? Tell me three things you love about it and three things you hate." Do that with every adult that you meet.
Speaker 301:10:57
How are we doing, sir? Doing well, thanks for being here today. Look forward to reading your book. Um, I was wondering if you—if it was an easy decision for you to stop being an active partner at Benchmark, and if you ever miss it. So, um, this will sound maybe a little, um, pompous, and I apologize. I was—I—I was watching this, uh,
Bill Gurley01:11:25
...interview between David Letterman and Jerry Seinfeld. And they both talked about this book Steve Martin had written called Born Standing Up in this idyllic way. So it immediately went into my list. And Steve Martin, um, was a grinder for 15 years. He didn't—he didn't really break until his, kind of, mid-40s when the "wild and crazy guy" stuff happened, and all of a sudden, his career—you know, he had been like this, doing vaudeville stuff, and all of a sudden, a rocket ship. And he was—he went from nightclub to small venue to arenas overnight. And then he stepped out on the stage in Vegas once, and the upper row was empty. And he never went on stage again. He quit the tour the next day, and he went and became an actor and a banjo player and this other stuff.
Bill Gurley01:12:18
And when I read it, it just seemed so perfect and poetic that that would be a better way to do it. And I had watched a few venture capitalists hang on too long. And luckily I was wealthy enough, I didn't need to hang around. Equal, that is the equivalent of the 30-year thing from the previous two times, but I knew when I read that I'm within years of pulling this trigger. And so I'm going to go try and find some fun other things to do. After the book, that's the answer to the question, so I think with, with that, that's a good place, yeah.
Interviewer 101:12:58⚠ 0.42
Thank you so much.