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Michael Lewis
Author and Financial Journalist

The Best Career Advice You’ll Ever Hear

📅 Mar 05, 2026 Bill Gurley 67 MIN 8112 VIEWS 456 SEGMENTS · 3 SPEAKERS
In this episode, legendary venture capitalist Bill Gurley sits down with bestselling author Michael Lewis to discuss his New York Times bestselling book Running Down a Dream. 1. Why graduates must become AI-enabled to stay relevant 2. How to build a career path with high agency 3. The importance of finding your tribe early 4. Why most people live with career regret — and how to avoid it 5. How to think like an artisan in your field 6. Lessons from NASA, Wall Street, and Silicon Valley I WROTE A BOOK! Runnin' Down a Dream Pre-order link: https://a.co/d/0c8GdH8O Follow us on X: https://x.com...

Questions asked in this interview

12
  1. 0:00What advice do you give to young graduates who are experiencing anxiety that AI is taking away entry-level jobs?
  2. 4:18Did you want to go into that line of work?
  3. 5:58And so why do you leave that job?
  4. 11:21Did your coaches mean a lot to you?
  5. 18:15Because I want to — did you ever get to a place in your life where you looked up and said, 'I want to be that in 30 years'?
  6. 19:49And how did you know that?
  7. 30:28Did you interview all the people who were in here?
  8. 33:57It's [laughter] and I said, why do I need—why do I need you?
  9. 40:02But you know what's interesting about bringing that up?
  10. 45:23And like you've seen the writing in the chapter, right?
  11. 48:47And he wrote me a letter that makes me cry if I read it again, explaining how much he understood what I wanted to accomplish. Right?
  12. 56:30I'm just starting it with my money and money from the book, right?
Interviewer 0:00 ↗
What advice do you give to young graduates who are experiencing anxiety that AI is taking away entry-level jobs?
Michael Lewis 0:06 ↗
I'd have a couple of pieces of advice. One, in any role in any field, be the most AI-enabled version of yourself you can possibly be. There's tons of anthropologists that have written about how we evolve with our tools. And you can just imagine a farming competition between a guy with a tractor and some drones and the other guy's got a plow and a donkey. Who's going to win? And you need to think about it that way. If there are 40 people in your org all doing the same thing and you understand how AI affects that role more than the rest of them, you're not getting laid off. Like it's just not going to happen. And you'll also start to understand what parts of your job are a threat or not. And maybe you can elevate yourself to where you're a designer and not the worker bee because you now have this power.
Interviewer 0:47 ↗
All right, we're going to do 45 minutes of just the two of us and then we're going to do your questions. Um, the book's great.
Michael Lewis 0:54 ↗
Thank you. I mean, you know, how I knew it was great is that so my just-graduated-from-Marin-Academy son, who's taken a gap year and is in London working, asks me all the time the questions you answer — the anxiety in the air around him about what he's going to do with his life and what, like, how do you even think about it? Um, I think you've hit a nerve. I think you're going to find...
Interviewer 1:20 ↗
Very kind. This thing is going to run and run and run. But we're not going to get the book right away. I'm going to do this in stages. Okay. And we're going to start — we've known each other. How did we meet? I can't even remember how we met, but we met a long time ago. Was it through Moneyball?
Michael Lewis 1:34 ↗
Maybe. I don't know.
Interviewer 1:35 ↗
Yeah. Yeah.
Michael Lewis 1:36 ↗
But it was...
Interviewer 1:37 ↗
I think it was my...
Michael Lewis 1:39 ↗
Yeah. So a long time ago.
Interviewer 1:41 ↗
And my first impression of you was you were tall. And I think it probably shapes everything that happens to you. I think you can't go through the world 6'9" without having a kind of 6'9"-like life. Uh, [laughter] and for good or for bad...
Michael Lewis 1:54 ↗
And well, you know, there is this thing with really tall people that you spend your life knowing people are watching you and I think it makes you better behaved. I think you're not going to get away with anything. You [laughter] really are. You're not going to sneak one by anybody. And so, you have to have like a better character when you get to be your size.
Interviewer 2:16 ↗
All right. Um, but so I want to start with your life a little bit because your life is what informs this book. I want you to walk us through your life up to the moment you get on stage at the University of Texas in 2018 and give the speech that leads to this book. Tell me where, how you grew up.
Michael Lewis 2:34 ↗
Um, I grew up in Dickinson, Texas, which is in between Houston and Galveston in Galveston County. Um, my father, and I think this is relevant to the overall story for a reason I can share. My father grew up in rural North Carolina, fell in love with gas airplanes as a kid. Like his father built him a shed behind the house and he's out there till 12.
Interviewer 2:55 ↗
Was he a real country boy?
Michael Lewis 2:57 ↗
No.
Interviewer 2:57 ↗
No. Real North Carolina. Real North Carolina. When you're...
Michael Lewis 3:00 ↗
No, I know. I know. But he's playing with those old Cox model airplanes and he goes to NC State and gets an aeronautical engineering degree and he's working at Langley Air Force Base in a wind tunnel and someone comes by and asks him and 49 other people working there, 'Would you want to move to Houston and help start NASA?' And he said yes.
Interviewer 3:23 ↗
Of course.
Michael Lewis 3:24 ↗
Well, I don't know, is it of course? Like, you know, you grow up — some people grow up in a geographic area and that's pretty daunting to jump that far. But the reason I think that story is relevant is when it came time for me to think about jumping across the country, it seemed natural because I had seen this example.
Interviewer 3:46 ↗
So you eliminated that fear of having to go somewhere else.
Michael Lewis 3:49 ↗
Or even knowing what it led to for him. I mean, to grow up on a farm playing with model airplanes, you know, he's born in '36, so, you know, 18 is what — is that 50? 54. By '69 they put a man on the moon. Like that's quite a run.
Interviewer 4:08 ↗
Yeah. [laughter] He was in the middle of it.
Michael Lewis 4:10 ↗
Yeah. Half the fathers on the street I grew up on worked at NASA. So it was just around us. It didn't seem strange.
Interviewer 4:18 ↗
Did you want to go into that line of work?
Michael Lewis 4:20 ↗
No. No. And but by the time I was graduating high school in '84, you know, it had moved on to the space shuttle. And even that was, you know, not — I wasn't drawn to that. But my sister... this could take forever for...
Interviewer 4:34 ↗
No, I'll cut you off. I [laughter] have some specific things I want to do with you.
Michael Lewis 4:37 ↗
My sister was a double E at Rice and could have gone to a bigger company and went to Compaq Computer Corporation in Houston, which was a super hot startup at the time. John Doerr was on the board. Um, it was being disruptive of IBM and so she was an early employee there, which is another data point, you know, that I have in my life. And I followed her there.
Interviewer 5:04 ↗
When, how did you figure out what you wanted to be?
Michael Lewis 5:06 ↗
So when I was like a sophomore in high school, I got a hold of a Commodore VIC-20, which was this precursor to the PC that you plugged into a TV, right? And I would buy these magazines that had code written in them and before I even knew how the code worked, I'd type them in and see it work. And of course I'd make typos and it wouldn't work and then I'd have to figure — I learned to code that way through that and got fascinated with that you could write a program that could do something. And by the way, like half the people my age in Silicon Valley have that same story.
Interviewer 5:41 ↗
Yeah. But if I had met you when you were in junior or senior in high school and asked you what you were going to do when you grow up...
Michael Lewis 5:47 ↗
Computer science for sure.
Interviewer 5:48 ↗
That's what you're going to...
Michael Lewis 5:49 ↗
Yeah. And I went to college and that's what I got to do.
Interviewer 5:51 ↗
You were going to program computers?
Michael Lewis 5:53 ↗
Yeah. Yeah.
Interviewer 5:53 ↗
That's not what you end up doing.
Michael Lewis 5:54 ↗
No, no, no. But I worked at Compaq for a little over two years.
Interviewer 5:58 ↗
And so why do you leave that job?
Michael Lewis 5:59 ↗
A couple things happened. One, I developed this mental exercise that I didn't realize I was doing at the time, but I said to myself — well, a couple years in, we started a third project, looked like the second project, looked like the first project, and I was starting to pay attention to some broader things and it looked a little redundant. And I said to myself, do I see myself here 30 years from now? And there were people in the building that had been engineers for 30 years, so I could get a perspective on it by just thinking, do I want to be them? And the answer was no. Very quickly in my brain. The answer was also — I had read Peter Lynch's 'One Up on Wall Street' and I was starting to get fascinated with stocks. Like when I got home at night, I got this Value Line notebook they used to have, single pages, it was like 400 pages, you get updates in the mail. Um, yeah. So I started thinking about stocks a lot out of just interest.
Interviewer 6:59 ↗
So that moment — because I had a moment like this when I was working on Wall Street and I [laughter] wrote a book about it. But no, but the moment when you look at the people who were in whatever you just started out in and you don't really want to be that in 30 years — that's one thing. But the other thing you said is that it sounded like it was repetitive.
Michael Lewis 7:17 ↗
It was.
Interviewer 7:18 ↗
So you weren't learning, right? So you're — and learning is a big deal with you. You always love to learn.
Michael Lewis 7:22 ↗
Yes. Actually, when I decided to leave Compaq, I went to business school at the University of Texas and for some reason I fell in love with reading there. I did read that Peter Lynch book, but prior to like high school and undergrad, I didn't read much. But in business school, like a bit flipped and I just started reading everything. Yeah. Including...
Interviewer 7:46 ↗
This is the male brain waking up at age 25, [laughter] right? No, that's what happens. I think that is what happens.
Michael Lewis 7:52 ↗
Yes. Our brains are a little slow to come along. [laughter] Mine was. I know I had a similar sort of experience. Yeah.
Interviewer 7:58 ↗
So, um, so we skipped over one thing because I think the fact that you're 6'9" and played basketball at the University of Florida even though you didn't play a lot, right? You were on a D1 team. You were surrounded by NBA players.
Michael Lewis 8:11 ↗
I say I practiced basketball, but yes.
Interviewer 8:13 ↗
But you practiced basketball with three guys who play in the NBA.
Michael Lewis 8:16 ↗
Correct.
Interviewer 8:17 ↗
It was a pretty serious...
Michael Lewis 8:18 ↗
And people have asked me how that — the only thing I could possibly say how that might have impacted my career path is one, I saw people get to very high places that I knew. So like there's a certain like, oh, that's doable.
Interviewer 8:38 ↗
You mean the NBA?
Michael Lewis 8:39 ↗
Yeah. But I knew for me it wasn't that lane. So if I wanted to do it, I'd have to find another lane. Right.
Interviewer 8:46 ↗
But still, like it's interesting to see that kind of level of success up close and know about it. But I mean, we're going to get to your talk because the talk is the catalyst for this book. But when you talk on a stage, you don't remind me of any VC I know. You remind me a lot of basketball coaches I know.
Michael Lewis 9:10 ↗
Is that right?
Interviewer 9:11 ↗
Oh yeah. You're a coach. You are so — the way you talk, the way you're [laughter] talking to them, you sound like you're talking to a team at halftime that you're slightly irritated with [laughter] and you're holding — you're not gonna go crazy on them, but you're slightly irritated with them and you're telling them how life works. And so you clearly picked up a lot of your...
Michael Lewis 9:37 ↗
One of the founders I work with is in the audience.
Interviewer 9:40 ↗
Yeah. A lot of you — I mean, you brought up — I can't remember whether you brought it up in the talk or the book, but it was in the talk — you were quite moved by Bobby Knight's speech introducing Mike Krzyzewski into the Hall of Fame. I went and watched that and he reminded me of you. [laughter] He did. So you have this — am I wrong that your athletic — no, let me just ask the question I want to ask: your athletic career shaped you too. It wasn't just your dad was at NASA and you played with computers. You clearly cared a lot about sports. You don't go suffer at the end of the bench on the University of Florida unless you care about this. So tell me about that part of your development.
Michael Lewis 10:28 ↗
I don't — I mean, like I said, the part that I think I might have taken away from it is just simply knowing how far away the talent level of the people that went to the NBA was from the rest of us, right? Like even in practice every day, you could just tell, right? And knowing that if you were going to do something at that level, it would require you to have that same kind of advantage in whatever it is you go do. Like it was a real awakening of differential of potential.
Interviewer 11:03 ↗
Nothing about hard work or teamwork or any of that stuff that comes?
Michael Lewis 11:06 ↗
I think all that stuff leaks in as you go through the whole process and [snorts] grinding and coaches yelling at you and like not being the end of the world, you know.
Interviewer 11:21 ↗
Did your coaches mean a lot to you?
Michael Lewis 11:25 ↗
No, not really. [laughter]
Interviewer 11:27 ↗
Okay. All right. That's interesting. That's — I, you know, [laughter] I like to see you squirm a little bit. I read your book 'Coach'. I did not have...
Michael Lewis 11:36 ↗
You didn't have that experience.
Interviewer 11:37 ↗
I didn't have that experience.
Michael Lewis 11:38 ↗
Yeah. I got lucky. I mean, not everybody has that experience.
Interviewer 11:41 ↗
Yes. Um, all right. So you leave Compaq, you go to business school and get us from there to Silicon Valley.
Michael Lewis 11:49 ↗
Well, I went through Wall Street. So I thought about venture capital a little bit when I was in business school. I was curious about it. Um, I couldn't find a way in. I had a few informational interviews. They said, 'Go work for 20 years and call me back,' which I [laughter] thought was not really an executable plan. Um, and then I started reading business magazines. I really loved my corporate strategy class and a lot of MBA students sit in the big open area and pretend to be executives and read Fortune and Forbes and Wall Street Journal and I was of course reading the tech articles because that's what I was excited about. And there was this team of sell-side analysts at Goldman Sachs — Dan Benton, John Levinson, Rick Sherlin — and [snorts] they were considered the axe. And the reporters when they wanted to write about these industries would always ask them. So I'm reading this stuff and they keep coming up like these are the people that analyze these important tech industries. So I did what you read about in books. I cold-called him and said, 'Can I come see you?' And Dan and Rick said, 'Yes.' I'm like a first-year student at University of Texas, pretty far away from New York. Um, and then because I knew they were so well known, I called the other research directors and said, 'I'm going to be in New York meeting with Rick Sherlin and Dan Benton. [laughter] Can I get 15 minutes of your time?' And I ended up with like seven meetings with research directors and one of them gave me a shot — Al Jackson, who was at the book party on Monday night, which was great to see him. And by the way, he cared a lot about the athletics piece.
Interviewer 13:34 ↗
I bet all the Wall Street people did.
Michael Lewis 13:36 ↗
Yeah. I was asking him why he took a chance on this kid from Texas because the incoming group of people from MBA programs that year, there were 40 of us and I was the only one that wasn't Columbia, Wharton — you know, the ones you would expect.
Interviewer 13:51 ↗
Yeah. But one of the things that signals if you've been through a D1 athletic program is you've learned how to suffer.
Michael Lewis 13:56 ↗
Yeah. And work and have work ethic.
Interviewer 13:58 ↗
Yeah. That's right. Then you're going to have to suffer in those jobs. So your interest in Wall Street comes from reading Peter Lynch. This is what gets you — a little bit in your book, which I know you hate.
Michael Lewis 14:07 ↗
You say this. I don't hate. So I read — I got to it and I thought it was funny. He said that he wrote... What year did it come out? '89. Yeah. So I went to work on Wall Street in '91. Okay. Yeah. Uh, and you — I didn't...
Interviewer 14:21 ↗
I should share with the audience Michael's book, 'Liar's Poker'. Um, he thought he was writing a book to tell people, 'Don't ever come to this horrible place.' [laughter]
Michael Lewis 14:32 ↗
That's your take on my book. I...
Interviewer 14:34 ↗
I don't — that's my take on you describing...
Michael Lewis 14:36 ↗
No, no, not exactly. I didn't [laughter] have that kind of view. My view had a little more nuance than that. I was watching people who had not the benefit of this advice at Princeton, where I went, anxious about their careers. And many of them had done all the right things to get to Princeton and they were — what is the next right thing to do? Like they wanted a treadmill and Wall Street — I watched Wall Street become this treadmill and I watched people who really had talents and interests that should have taken them in a different direction feel they couldn't afford to do it because you had to do this because it was too scary. Turning down Goldman Sachs would have been like turning down Princeton. And that bothered me, really bothered me. And so what I was hoping it would do was sort of demystify it so that the kid who was going to be an oceanographer would just say, 'Okay, I know what it is. Silly. I'm going to go be an oceanographer.' It is true that it did not have that — it had that effect with some kids. But with other kids it was more, 'Oh my god, the dog whistle coming out of 'Liar's Poker' was Michael Lewis doesn't know anything. He persuades us he doesn't know anything.' And within 18 months they're throwing hundreds of thousands of dollars a [laughter] year at him to give financial advice. I don't know anything, says the reader. Where can I go to get paid hundreds of thousands of dollars a year? So it attracted all these people into the business. I don't want to digress on me too much, but I just would flash forward.
Interviewer 16:06 ↗
So my main draw was the thing I'd mentioned, the tech analyst thing, but your book did create this notion of sensationalism, that it would be exciting. Yes, exciting. What was it?
Michael Lewis 16:20 ↗
Oh yeah, I actually had a blast. It was a rocket ship. I got very fortunate. Um, I had this amazing call on Dell that worked out like perfectly.
Interviewer 16:33 ↗
Was it going up or going down?
Michael Lewis 16:34 ↗
The company was in trouble. It was trading at six times earnings. Their laptop had caught on fire and they had this option hedging strategy gone awry that they had to do a mea culpa to the street. So the street hated the stock. But we had done some analysis using this new tool called return on invested capital and they had like a 10-to-1 advantage over Compaq and the other companies because of how they worked their inventory and their positive cash flow cycle and we went positive on it. They fixed those two problems. Stock went up 100x. [snorts]
Interviewer 17:06 ↗
And you got credit for it.
Michael Lewis 17:07 ↗
Yeah, I got credit for it and I got to know Michael, which is awesome, and the CFO at the time, Tom Meredith.
Interviewer 17:12 ↗
So why do you leave that job if it was so great?
Michael Lewis 17:15 ↗
And one of the crazy things about that job is you visit companies, you go straight and talk to the CFO and the CEO. It's crazy. You're 28 years old and you get to go straight to the top, which the access is unbelievable.
Interviewer 17:28 ↗
Because they think you're going to say nice things about them.
Michael Lewis 17:29 ↗
And maybe, but still you get in, right? Um...
Interviewer 17:33 ↗
Journalists have that too.
Michael Lewis 17:35 ↗
Yeah. Yeah. Yeah. And so podcasters now, I meet them and they're like — it's unbelievable. They just sit there interviewing people that they love. So it's cool. Anyway, there was that great part. Um, I had the same exact exercise one day. The company was in Park Avenue Plaza, 52nd and Park, and the research team had the 36th floor and the corners were held by the senior-most people. And I'm there at 10 p.m. one night and I walk around the floor and I pause — I don't even know why I did this — in front of each of those four offices and said, 'Is that going to be me? Do I want that to be me 30 years from now?' And I got to know that night. I remember making that decision that night.
Interviewer 18:15 ↗
Because I want to — did you ever get to a place in your life where you looked up and said, 'I want to be that in 30 years'?
Michael Lewis 18:21 ↗
I never — when I got into venture, I never had that discussion with myself ever again. Okay. No. No.
Interviewer 18:27 ↗
So it didn't — at least the sight of the people.
Michael Lewis 18:30 ↗
Yeah. And I didn't, you know, I kind of got prepared to tilt into venture and to leave. In neither of these cases did I walk out the door the next day. I made a mental decision to find a way to go in a different direction.
Interviewer 18:44 ↗
What interested you about venture capital?
Michael Lewis 18:46 ↗
Um, I just answered this question the other day. So I love technology. I love disruption. Right. I really got into business strategy and this idea that you could bet on a startup kind of outmaneuvering an incumbent and then being successful and then you get to bet on it. Because I started trading stocks. When I was in college, my friends and I would go to Binion's and play single-deck blackjack. So I had this gambler kind of thing too.
Interviewer 19:18 ↗
You like to gamble?
Michael Lewis 19:19 ↗
Yes. Yes. And so technology, disruption...
Interviewer 19:23 ↗
Do you like to gamble when you're counting cards or do you like to gamble?
Michael Lewis 19:26 ↗
I prefer to have edge.
Interviewer 19:27 ↗
Okay. I'm not — I've met — when you sit at the stock... No. No. No. Never. You don't like that?
Michael Lewis 19:32 ↗
No. And I meet people that want to flip, you know...
Interviewer 19:35 ↗
Coins for...
Michael Lewis 19:36 ↗
Yeah. For a lot of interest. None. I have zero interest in that.
Interviewer 19:40 ↗
You like the idea of having an edge and then bet-making.
Michael Lewis 19:42 ↗
Yes. Yes. Yes. Yes. Right.
Interviewer 19:44 ↗
All that.
Michael Lewis 19:45 ↗
Right. And so it was perfect. It was like all those things combined.
Interviewer 19:49 ↗
And how did you know that? Like how would you even have discovered when you come into...
Michael Lewis 19:53 ↗
Okay, so Compaq was a startup that was very successful. My sister got options, right? I learned about that and started to have that idea. Um, I get to Wall Street and there are hot young companies that are growing really fast that are exciting to cover and then they're like, 'Would you cover IBM?' And I'm like, 'I don't — I had zero interest.' So that told me I wanted to be more over here, even on the other side of that, right? You know, and what was happening on the edge — the edge was very exciting to me. And so venture is where it gets really on the edge. And then I'd already decided I wanted to move to the buy side. It was either going to be public or venture, right?
Interviewer 20:34 ↗
Because on the sell side you're talking — you want to do it yourself.
Michael Lewis 20:38 ↗
Yeah. Exactly. You don't really have any money on...
Interviewer 20:41 ↗
Those who say don't know and those who know don't say. So we should talk about your venture career, but I want to flash forward to your speech, but we'll come back to it because it's interesting. You're kind of shy about talking about your career. I mean, you said when you went to sell a book that everybody wanted you to write about Uber or...
Michael Lewis 21:01 ↗
My career, every single one of them.
Interviewer 21:02 ↗
Yeah, or a memoir.
Michael Lewis 21:05 ↗
They didn't want a how-to book, that's correct.
Interviewer 21:07 ↗
About how to lead. Right. Right. So that's interesting. But you get invited to go back to your alma mater.
Michael Lewis 21:15 ↗
Yeah. And give a talk to a class.
Interviewer 21:17 ↗
Yeah. It was a new incoming MBA class.
Michael Lewis 21:19 ↗
Yeah.
Interviewer 21:20 ↗
And you can talk about anything.
Michael Lewis 21:21 ↗
Yeah.
Interviewer 21:21 ↗
Why did you decide to talk about this?
Michael Lewis 21:23 ↗
During my entire career I was a writer and I wrote more. I started as a sell-side — you're forced to become a writer — but I found a way to use writing as a way to differentiate myself as a venture capitalist. Started as a sell-side analyst but I kept doing it through blogs. I mean, it started as a newsletter but eventually became blogs. And in that process, and I'm sure writers do this as well, a new idea pops in my head, I grab a new file, open it up, put the notes in, and as something new comes across that's related to that, I stick it in there and see how it builds. And you know, for every blog post I did, there's three or four of those that never see the light of day, right? I was reading a bunch of biographies at one time and there was a third biography and I saw this through-line to the second and the first. And the same way I'd write about frameworks for a new technology or new disruption or marketplace companies and the internet, I had that same kind of aha moment that these pieces fit together in this way that there was a framework.
Interviewer 22:28 ↗
The biographies fit together.
Michael Lewis 22:30 ↗
Yes.
Interviewer 22:31 ↗
And what was it? You saw a pattern?
Michael Lewis 22:33 ↗
I did.
Interviewer 22:34 ↗
And what was the pattern?
Michael Lewis 22:35 ↗
Well, I thought — so the thing that was super interesting to me is there were three people all in fields that your parents would tell you not to go into. It was a folk singer, a restaurateur, and a basketball coach. They all started on the very bottom rung. They were all insanely curious about their field. So much so that they're out learning proactively on their own. Like not learning in a classroom where a teacher's teaching you. They're studious.
Interviewer 23:01 ↗
They're not doing it for an A.
Michael Lewis 23:02 ↗
They're studious. And all three of them are just studious in a way that I've never seen other people do, you know. And uh...
Interviewer 23:11 ↗
Can you say who they are?
Michael Lewis 23:12 ↗
Yeah. Yeah. Yeah. So, I mean, they're all three profiled in the book and the video, but Danny Meyer, a restaurateur in New York, takes copious notes every time he visits any restaurant.
Interviewer 23:23 ↗
Before he even becomes a restaurateur.
Michael Lewis 23:25 ↗
Yes. Yeah. Even as a hobby when he's young. Um, Bob Dylan, who most people don't know how studious he was on...
Interviewer 23:34 ↗
I have no idea.
Michael Lewis 23:35 ↗
On his way up, and the movie missed it too, the new movie that came out.
Interviewer 23:38 ↗
Good movie.
Michael Lewis 23:39 ↗
But the Scorsese documentary gets it, you know. But he's been a lifelong learner. He just came out with this book about 50 songs that mattered most, they're not his.
Interviewer 23:51 ↗
Right, so he's, you know, like studying.
Michael Lewis 23:54 ↗
And then Bobby Knight, who in his early way up forced his way in front of like six of the best coaches in the history of the sport. Like I've never seen a mentor pursuit like that, right? Ever. Ever. And the thing I really love about Bobby Knight — everybody knows the chair and the anger and all that, right? He has a coaching tree that is bigger than anyone that's ever coached.
Interviewer 24:22 ↗
You put it up on a slide in your talk.
Michael Lewis 24:24 ↗
Yeah. Yeah. The number of people that either played for him or coached under him that have gone on to coach on their own.
Interviewer 24:29 ↗
So he himself was a teacher.
Michael Lewis 24:31 ↗
Yeah. Yeah. And I think it's an interesting way to judge someone's impact on the world, you know. But Danny has the same kind of thing. If you talk to a chef that ever worked at a Danny Meyer restaurant, it matters to them.
Interviewer 24:45 ↗
Uh-huh. And that's got to feel really cool if you're Danny, that people care that they were just going through your program, that you got exposed to it a little bit. So you're about to give this talk at the University of Texas. Notice this pattern. These three people who you admire and are interested in all had a kind of similar approach to how they found their careers in fields that no parent would say.
Michael Lewis 25:09 ↗
Yeah. And the intentionality — that part was really interesting to me. Like Danny didn't originally have that intentionality. He had this amazing moment with his uncle one night at dinner, his uncle Richard, and then the next...
Interviewer 25:24 ↗
Describe that moment. That's an interesting moment.
Michael Lewis 25:26 ↗
I mean, if I have one goal of this book, it's to be Uncle Richard for as many people as possible. So, um, Danny was poli-sci at Trinity in Connecticut and he worked as a salesperson but always knew he was going to go to law school because he's poli-sci. This was just, you know, to save up some money to go to law school and he's going to take the LSAT the next day. And he goes to dinner with his uncle Richard and I guess his uncle Richard notices he's got a frown on his face. He said, 'Why are you so down?' He said, 'I have to take the LSAT tomorrow.' His uncle Richard said, 'Do you really have to? Like, do you have to take the LSAT tomorrow?' And this led to a conversation where his uncle Richard told him, 'You know, Danny, all you ever do is think about restaurants. Why don't you just go open a restaurant?' It had never dawned on him. His father had had a couple bankruptcies in the broad travel and leisure space, and so his father had kind of pushed him away from the idea. He needed Uncle Richard to give him permission to go think about this thing.
Interviewer 26:35 ↗
There are two things going on there. One is freeing yourself from this sense of obligation to — 'I have to go do this. I'm supposed to go do this.' You see that broadly, 'I'm supposed to go make a lot of money.' And that really is a trap. You get stuck in this...
Michael Lewis 26:56 ↗
I think it shuts down your imagination. I think you get stuck just because the grind today for young adults is so hard that it feels like sunk cost.
Interviewer 27:05 ↗
Yeah.
Michael Lewis 27:05 ↗
Like you come out and you've done all this.
Interviewer 27:07 ↗
I've done all this work to get to this place, like [snorts] going somewhere new, I would be giving up all this work that I put in.
Michael Lewis 27:14 ↗
Right. So ignoring sunk cost is one of the great lessons in life.
Interviewer 27:17 ↗
Yes. Right. No doubt.
Michael Lewis 27:18 ↗
Yeah.
Interviewer 27:19 ↗
But the second thing is it's okay to go do the thing you want to do.
Michael Lewis 27:25 ↗
Yes.
Interviewer 27:26 ↗
Even if it sounds maybe not so promising.
Michael Lewis 27:28 ↗
Yes.
Interviewer 27:29 ↗
Because the intensity with which you want to do it will overwhelm everything.
Michael Lewis 27:35 ↗
And then the moment — like once Danny had that bit flipped, it changed everything, right? Like he became — I mean, he was already studious about this industry, but he became this massive learn-it-all. He enrolled in a $300 restaurant management course that he found in a magazine on a corner of the street in those boxes, you know, in New York.
Interviewer 27:56 ↗
Yeah.
Michael Lewis 27:57 ↗
Um, and there's another character in the book that also went to a cosmetology course offered by the city of Los Angeles that's free. And this bottom-rung notion is really interesting to me, like that you don't have to have networks or connections. And he took a job that was paying like 15 grand a year just to learn. Like he knew it wasn't the income he needed, but he wanted the experience.
Interviewer 28:25 ↗
You know, it's funny. It's the old guild model.
Michael Lewis 28:29 ↗
Yes.
Interviewer 28:30 ↗
The old — you apprentice, the old apprenticeship.
Michael Lewis 28:35 ↗
Well, and then he went through Europe doing these — the stage is a fancy European word for work for free, which is the apprentice thing. And he went and did that all through Italy, all through France. But it is the way to learn.
Interviewer 28:47 ↗
Yes.
Michael Lewis 28:47 ↗
Yeah. And there are a lot of places, a lot of careers that really don't offer it for...
Interviewer 28:51 ↗
I agree.
Michael Lewis 28:52 ↗
Like you have to almost insist upon the experience.
Interviewer 28:57 ↗
Yes. And you're encouraging people to do this. But one of your lessons is like, be good at finding mentors.
Michael Lewis 29:06 ↗
Well, yes. But also note one great test of whether you're really tilting at your true obsession and fascination is that learning — I call it free — like that studying that Danny did, like he was doing it before he ever became convinced it could be a career. But like if you really love what you do, you go home at night, you're reading about how to be better at it, you know.
Interviewer 29:33 ↗
You don't think of it as...
Michael Lewis 29:34 ↗
You don't think of it as work. And I would say you might even get positive energy from it, right? Whereas studying something you don't love might suck energy from you.
Interviewer 29:43 ↗
I want to talk about why so many people do things they don't want to do.
Michael Lewis 29:46 ↗
And by the way, Danny would do that the rest of his career. I mean, he would go on these tours. When he opened this Blue Smoke restaurant in New York as a barbecue place, he took his team all around America and sampled the top barbecue places all over. When he opened Shake Shack, the very first one in Madison Square, he went to 10 different burger places around the US and his team would debate what worked and what didn't. Like it's a very artisan approach to what he did and what he does. And he wrote a book called 'Setting the Table' where I gathered most of this information from. And I've gotten to know him because he was on the board of OpenTable. But...
Interviewer 30:28 ↗
Did you interview all the people who were in here?
Michael Lewis 30:30 ↗
Not all of them because Dylan's very hard to get to. [laughter]
Interviewer 30:34 ↗
I heard when Scorsese did the documentary they had an intermediary. [laughter] So just to finish with the talk. So you decide this is the subject of your talk and you decide you're going to try to distill some principles to get across to them.
Michael Lewis 30:48 ↗
Yes.
Interviewer 30:48 ↗
What were the principles? Because you've expanded on them.
Michael Lewis 30:50 ↗
I added one.
Interviewer 30:51 ↗
So all those were there but one.
Michael Lewis 30:53 ↗
Okay. Yeah. Uh, find your passion — we renamed it 'chase your curiosity' in here. People find the word passion very cliché-ish. Um, my...
Interviewer 31:03 ↗
You quote Jerry Seinfeld saying...
Michael Lewis 31:04 ↗
Jerry Seinfeld gave 'forget your passion' where he said figure out what you're fascinated by.
Interviewer 31:07 ↗
Fascination.
Michael Lewis 31:08 ↗
And I think it's a better word actually. And then hone your craft, which is just immense continuous learning. And if you're not in the right lane, I don't think you can do the second one, and the second one's a good test of whether you're in the right lane. They reflect on each other really well, right? Um, and all these people did it. I mean, the Bobby Knight stuff where he's showing up, you know, to these coaches with a hundred play cards and asking them if they'll go through them one by one with him, right? Like that's a crazy level of obsession.
Interviewer 31:40 ↗
What's the venture capitalist version of hone your craft? What did you do to become a good venture capitalist? [snorts]
Michael Lewis 31:46 ↗
I think you — well, for me, I had the advantage of starting on Wall Street. So I had read Buffett and Howard Marks and Graham and Dodd and I think that gave me a different lens. I always said venture is creating products for the public markets to buy. So you kind of want to know what they want, right? Um, and I came at it from that. And then, you know, John Doerr and Mike Moritz, like the contemporary leaders when I joined, you study them. You know, there's books about the people that came before them, right? You study those. And then in venture you have to study the edge of the technology and have insane FOMO about it.
Interviewer 32:27 ↗
Did you feel like you got better with age?
Michael Lewis 32:30 ↗
At the — you get better at sitting in a boardroom, keeping your mouth shut, being better at those kind of soft human skills. I think staying on the edge gets harder as you get older. Okay. I think I've always said venture bends towards youth.
Interviewer 32:50 ↗
Uh-huh.
Michael Lewis 32:50 ↗
Because the new kids are doing new things, you know, right? And it's hard to keep up with...
Interviewer 32:57 ↗
Their time is absorbed with old things.
Michael Lewis 32:58 ↗
Yeah. Yeah. As a venture capitalist gets older, they have families, they get second homes, they might flake off, and it becomes harder to be all-in.
Interviewer 33:09 ↗
Right. Well, so before we — so at this, you give this talk.
Michael Lewis 33:13 ↗
Yeah. Um, and you...
Interviewer 33:15 ↗
I can give you the other ones real quick. So just because you started that. Um, develop mentors, and I have some very specific ways to do that. I think people screw that up.
Talk about that.
Michael Lewis 33:25 ↗
Embrace your... Okay.
Interviewer 33:26 ↗
What do people screw up?
Michael Lewis 33:27 ↗
They shoot too high. Like they just go up to someone who's got no time and...
says, "Hey, will you be my mentor?" Right.
Bill Gurley 33:35 ↗
So they shoot too high and they ask for this thing that seems gargantuan, and it's just—there's a nuance, there's a nuance to getting that right, and that ain't it.
I had an undergraduate at Cal email me a few years ago and said we needed to write a book together.
Michael Lewis 33:50 ↗
Yeah. [laughter]
Bill Gurley 33:53 ↗
And I just thought, this is—I don't even know what to do with that.
Michael Lewis 33:56 ↗
Exactly.
Bill Gurley 33:57 ↗
It's [laughter] and I said, why do I need—why do I need you? Yeah, yeah, yeah. Yeah, it's ambitious.
But yes. Okay. But—but—but I recommend two things. One, I recommend—and I borrowed this from Danny. When Danny set out to be a restaurateur, there were 10 people that he wrote down in a journal that were defining the new age of being in the restaurant business—Wolfgang Puck and people like that. And he kept like a fanboy journal on each one of them. And I think that's a great idea. Like if you're going to go be a writer, you know, have a profile of Michael Lewis and Malcolm Gladwell and Krakauer and like study what makes them great. Like there's never been a better time in the history of the world to learn on your own time, right?
Michael Lewis 34:46 ↗
There's so much stuff out there.
Bill Gurley 34:48 ↗
Yeah.
Podcasts, interviews on YouTube, AI—you know, you can just tell AI, "Hey, you be this person for a while. I'm going to ask you some questions."
Michael Lewis 34:57 ↗
Some people shoot too high. Anything else they do that they should—
Bill Gurley 35:00 ↗
No, but I love this exercise of having this group of people that you study like as a fan person, because I think you learn a lot through that. And if you ever meet them one day, you now are in a much better way to have a nuanced conversation because you know so much about them. And then—and then the other thing, just yeah, don't aim so high. Like grab someone two rungs on the ladder above you who's never been asked to be a mentor before, because they'll be flattered that you ask, and then you start—

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APA

Lewis, M. (2026, March 5). The Best Career Advice You’ll Ever Hear [Interview transcript]. Bill Gurley. CEOInterviews.AI. https://ceointerviews.ai/interview/3061711/

MLA

Michael Lewis. "The Best Career Advice You’ll Ever Hear." Bill Gurley, 5 Mar. 2026. Transcript, CEOInterviews.AI, https://ceointerviews.ai/interview/3061711/.

BibTeX
@misc{lewis2026_3061711,
  author       = {Michael Lewis},
  title        = {The Best Career Advice You’ll Ever Hear},
  howpublished = {Interview transcript, Bill Gurley. CEOInterviews.AI},
  year         = {2026},
  month        = {mar},
  url          = {https://ceointerviews.ai/interview/3061711/},
  note         = {Speaker-attributed transcript with timestamps}
}