How to Find a Career You Love, with Author and Venture Capitalist Bill Gurley

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Good Morning Brew Daily Show. I'm Neil Freiman. And I'm Toby Howell. To follow your passion or not to follow your passion, that is the question.

Legendary VC Bill Gurley explains how to find a career you actually love. It's Monday, December 29th. Let's ride.

Happy Monday, everyone. Hope you have a chill final week of 2025 ahead. You know what's not chill? Having a job you hate. Bill Gurley is one of the most successful venture capitalists in Silicon Valley history, having been an early investor in startups like Uber, and he came on the show to discuss his upcoming book about finding a job you're actually passionate about.

Are you implying that this is not a job you are actually passionate about, Neil? We get into Jeff Bezos' regret-minimization framework, whether you should really follow your passion, and he finally settles once and for all whether getting an MBA is worth it.

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There's Bill. Bill, thank you so much for joining us. Thanks for having me on. All right. So you've written this book, Running Down a Dream, shoutout Tom Petty, in which you lay out the principles for essentially finding your dream job. The first principle of that is chase your curiosity. Now, growing up, I think I speak for a lot of little kids, little boys in the '90s, our main curiosity was sports. I wanted to be a SportsCenter anchor. Toby over here wanted to be a professional soccer player. He came pretty close. But it probably wouldn't make sense for us to all pursue a career in sports because maybe our skills don't exactly match onto the particular jobs in that industry. So my question is, how do you differentiate between a passion that would make for a good career and a passion that you should just keep as a side hobby?

Yeah. So one thing I would say, the initial impetus for the book came from me reading biographies. And I think a lot of people go through a period in their life where they just devour biographies. And I noticed some similar traits and processes that different people in far-ranging industries were doing that led to radical success. And the three that really kicked this off for me was a restaurateur, a college coach, and a folk singer. And those are all three industries your parents would tell you not to go into. And the one thing I would just say specifically like about the sports comment, we have several profiles in the book that are related to people that have thrived in sports in general.

You know, often not the talent person, but the number of jobs that surround the talent people is often 20 to 1. You know, there's lots, and I think a lot of young people don't perceive that to be true. We have a profile of a woman that's been wildly successful as a Hollywood agent that loved movies growing up, but never considered herself an actor/actress, and so never really leaned into it, and eventually came back around and realized, oh, I could be an agent and I can be around this stuff. And the book actually concludes with this interesting experience I had at South by Southwest where I sat in on this, you know, bizarrely peculiar panel on bedroom producers. Apparently now you can produce high-quality content in your bedroom with the modern tools.

And it was a sold-out room, and then they did Q&A at the end, and this girl walked up to the microphone and says, 'I'd really love to pursue a career in music, but my parents tell me it's too hard, you can't make money.' And one of the panelists said, 'You know, people say that, but I've never met anyone that leans into it and really pursues it that hasn't been able to have a career in this industry.' And so I think there's a little bit of a myth that these things are too hard. My test is—and the reason that chapter is titled 'Chase Your Curiosity'—my test as to whether you're going to be successful in the dream job and whether you should really push towards it is, are you willing to learn on your own time

this subject and to study it. And I like to say, if you have three episodes of Breaking Bad left, would you study this instead? Does it compete with what you do in your free time? And I think if you find yourself just so enamored with something that you're studying it, studying it for pleasure in your free time, that's a really good sign.

One thing I've heard you mention twice now is, 'My parents tell me not to do this. My parents maybe are pushing me down a different path.' Why do you think there's a delta between what maybe our parents were telling us and what maybe you are advocating for in your book?

Yeah, I think—I think, you know, a lot of our parents emerged from a time, especially our grandparents, maybe—and you and I are different generations—but where people had to take the job that was available to them. And a lot of people, you know, had to work two jobs. There was a lot of grinding out there. And so I think there was a natural reaction. We quote in the book the Willie Nelson song, 'Don't Let Your Babies Grow Up to Be Cowboys,' you know, 'but doctors and lawyers and such.' So we developed this mindset where you want to push kids towards economic safety. And that meant jobs where you know that the unemployment's low and the salaries are high. Interestingly, AI throws some of that into question as well.

But I think we've just pushed a lot of kids down this thing I call, like, the career industrial complex. And Jonathan Haidt calls it the resume arms race. Like, it starts early. It starts at, like, 10, you know, and you're adding in the lacrosse lessons and the cello lessons and the chess lessons and the foreign language. And, like, we're—we're really pushing these kids, like, in an industrialized way. You know, I had a chance to meet Rick Rubin recently. And in his book, he just says we don't allow children to explore anymore. It's almost like finding your fascination. There's not much time for it, you know.

Your book comes at an interesting time because the concept of following your passion or pursuing your dream job seems to be kind of at an all-time low right now. You have all these prominent voices like Scott Galloway saying, if someone tells you to follow your passion, it means they're already rich. And Mark Cuban once said, don't follow your passion, follow your effort. What are they getting wrong?

Well, I do think the phrase became cliché, you know, and when I gave the original speech, it was titled “Find Your Passion,” and I renamed it “Chase Your Curiosity” for this reason. And when Seinfeld gave the commencement speech at Duke, he made fun of the word “passion,” but then he reoriented it around a word, “fascination.” I think it meant the same thing. I—I take exception to those points of view, and I think in some ways they're being contrarian because it did become so cliché, and people say it all the time. But you're going to spend about 80,000 hours at work. And I've met people, and you and I were discussing before we started, that a lot of podcasters are in their dream job, and they look extremely happy all the time.

Both of you guys look really happy. Absolutely beaming. And, like, I do believe that the tools are available today to be successful in almost any field. Now, it requires an immense amount of commitment and an immense amount of self-directed learning. And so some people, I think, aren't up for the journey, you know. I had an interesting conversation with Angela Duckworth, who, in reflecting on *Grit* 10 years after she wrote it, she thinks that the passion piece should have been more accentuated versus the perseverance. Those were her two elements of grit. And she said, we've taught the kids how to grind. Like, we've literally taught them how to grind and, you know, kind of helicopter parents and, and—

What happens is they grind and grind and grind, and then they wake up either junior year in college, senior year in college, two years into the workforce, and they're just exhausted. And the one thing I would say that's a huge advantage if you have immense curiosity about a topic is that studying, that practicing comes for free. And there's no athlete in their 30s, 40s—Steph Curry, LeBron—where you would expect them to not practice. But in most careers, people don't think of honing your craft and practice post-college. And I think if you can put yourself in a career where you are able to continue to hone and self-practice, you're going to excel past the vast majority of other people.

So when it comes to dream jobs, obviously, a pro is you like what you do. You don't show up to work hating your life every day. But you argue it goes beyond that, and it's actually a competitive advantage in the modern job market. So can you break down almost the economics of passion for us?

Yeah, and by the way, one thing I should have said related to that—"don't do what you love" or "don't chase your passion"—the job satisfaction numbers are at an all-time low. The Gallup Poll numbers are like only 40% of people consider themselves engaged at work. This whole phrase, "quiet quitting"—there's actually people who are actively disengaged at work that are trying to harm the organization more. Like, it's horrific. And we did a survey with Wharton where we asked 10,000 people, "If you could go back again, would you do something differently?" and 60% said yes. So I think people aren't ending up in the right place, you know. But to your specific question about this disadvantage, like... if you study a lot of the greats, they're just all self-learners, and it's almost independent of industry.

And if you can find your way to be so curious about what you're doing that you're constantly learning. People that I profile—the first profile's on Danny Meyer, the amazing restaurateur in New York City. And, uh, my co-writer and I talked to him recently and he was coming back from a European learning trip where he took all his chefs and they went, you know, one after the other, after the other. His learning trips are a little bit different than maybe some others, but, but, but when people read the book, you'll see that they're—I understand how you can say like, "Yeah, you're eating at fine places in Europe." But they take copious notes. They, you know, they are there to learn. And every one of his endeavors, including Shake Shack, he went on a tour, you know, before he did this thing.

And it's just a really amazing, unfair competitive advantage. If you're young, one area of learning is always the new tools. And so if you're breaking into a new industry and you understand podcasts or you understand what makes Instagram work—like, imagine if that company has a product or consumer product, you're going to be highly differentiated by knowing what's on the margin and what's on the edge. And that can be extremely valuable to a young person in their career.

Speaking of new tools, if you were to start writing this book now instead of seven, eight years ago, would you change anything about it to reflect the impact of AI on the workforce? Should people still follow their passion if AI is better at it than they are?

Yeah, well, I would say two things about that. The first thing, which is a piece of advice to anyone in the world, is lean in and play with these tools. You know, it is the modern toolset. Like, if, if... if you come to the workplace and can't use Word or Excel or PowerPoint or email, you're disadvantaged. And this is the new version of that. And so no matter what you're doing, you should understand how these tools can be used to make you more competitive in your field. And just as I mentioned, understanding Instagram, AI in your field is the best way to stay at the forefront of what's possible and could accelerate you to the front of the line by being the first person that does that.

You did say on another podcast, Tim Ferriss's show, that you don't think there's ever been a better time to have a self-determined job process. What is a self-determined job process, and why is now the best time to pursue that?

I was talking to my friend Mike Mauboussin earlier today about his career journey. He's a famous intellect around finance and investing. And he talked about it in the very early days of his career. His self-learning meant going to the New York library with a bucket of coins so he could feed the microfiche printer to go find these articles where people had written things that he wanted to learn. You contrast that to today with all the greats that have gone and done interviews on YouTube, the immense library of podcasts that are out there, and now AI. I mean, you could be driving down the road and put AI in voice mode and just have a conversation with the AI—most intelligent encyclopedia of all time.

And so that's what I mean by that. Like, if you have a curiosity and want to engage in self-directed learning or studying the greats or anything like that, the stuff that's free and at your fingertips is unprecedented in human history.

Another one of your principles for career success is "find great mentors." Maybe that's ChatGPT, but maybe it's a person. And a lot of listeners hearing this are probably thinking to themselves, "Yeah, I'd love a mentor, but where, how do I find one, let alone a great one?" What is your advice for seeking out a mentor?

There's a lot of detail in the book, but at a high level, the things I would do is I'd divide it into two pieces. I would create aspirational mentors. So these are people, and Danny Meyer did this. He created a list of 12 of them that were innovators and people that were changing the restaurant industry. And he profiled them and studied them. So these aren't people you're going to meet tomorrow, but they're people that if you can fully understand them, what they've done differently, why they're successful, who are their mentors, what do they read—like, study them like you would, you know, studying for a history test. So that's one. And then be more practical about who your mentors are going to be at this point in time, and find people who are either close to you or a network, you know, or just go a level or two down the ladder.

I mean, people are flattered to be told that you're inspired by them. Right? And that's—if everyone shoots for Michael Lewis as a writing mentor, like everyone's going to fail, right? But there may be someone in your community that doesn't get that request that much and they're going to be more available. There are certain industries, Silicon Valley, you know, where I spent 25 years building my career, it is remarkable the number of people that will say yes to a coffee in that area. And I think it's because it's such a dynamic industry and people move in and out of different companies, but it's remarkable. And I've heard, and I actually saw a documentary about this, that the songwriter community in Nashville is similar.

Not the stars, but the songwriters. Like, if you reach out to somebody, they'll give you 10 or 15 minutes.

Neil, reach out to Taylor Swift. See what she thinks about you. She's around. She's around, yeah. One thing that this reminded us of is that Tyler Cowen, the economist Tyler Cowen, said, "All my mentors are younger than me at this point." Have you seen something similar in this age of rapid technological innovation?

Well, I certainly—well, one, you know, the industry I come from, venture capital, I've had a philosophy my whole life that it bends towards youth. That the disruptors of tomorrow are frequently in their 20s, and your ability to associate with them gets harder as you get older and older. The rule sets that crystallize in your brain as you get older makes it harder to see the disruption that's coming next. And so, yeah, it's a bit awkward, but if you're self-learning, you should be indifferent to the age of the person you're learning from as long as you know they know something you don't.

We'll be back with more Bill right after this.

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Principle number five in your career playbook is "go where the action is." In your view, where is the action right now?

Well, I mean, that whole chapter is about, um, identifying the epicenter of an industry, and it, and I have a list in the book of 10 reasons why this is something you should do. I recognize that it may not be economically feasible, and we should talk about that at the end. I'm launching a foundation to try and help even in that scenario. But, um, the benefits that accrue to you by being a songwriter that lands in Nashville or an entrepreneur that lands in the Bay Area are immense. And all the learning opportunities go dramatically higher. The optionality gets really enhanced. A lot of famous people... when you hear them tell their story, there's always this chance meeting that kind of came out of nowhere.

I was super lucky to meet this person. Like, if you're where that world is, the odds of that happening go up and up and up and up. And I think, I don't know who said that luck is when preparation meets opportunity, but opportunity is...

is enhanced greatly. I mean, you guys are in New York, you know this. Like, like stuff happens because you're in New York that wouldn't happen if you were in Topeka. Yeah, you get honked at a lot, but you're, you're a big, uh, you're a big Austin, Texas guy, so, and you came from Silicon Valley. So, if you were starting an AI company, would you do it in Austin, or would you do it in the Bay Area?

I mean, quite frankly, if you were going to, if you, let's say, you're a young person who just loves AI and wants to be in and around it, I would be in San Francisco tomorrow. I would get on a plane and be there tomorrow. It is where everything's happening. And, oddly—this is very unusual—but, but COVID led to a malaise, I would say, in the work ethic of the older Silicon Valley crew, writ large. These new AI kids have adopted this phrase from China, 996. And they are living it. And by the way, if you don't go there and don't know about 996, you wouldn't know your odds of succeeding are so low because they're working so goddamn hard in San Francisco right now.

Weigh in on that for us, because we've talked about 996 a couple times on the podcast. Do you think it's healthy? Do you think it's something people should strive for? Or is it maybe just a fad right now?

It may just be a fad, but there's a window of opportunity around AI. And some of the early winners are going to be rewarded substantially for that success. And whenever there's a disruption, the opportunity to grab the flag, if you will, in an industry is way higher. And so, from a... from a very pragmatic point of view, you should want to run harder right now, because it may be a window of opportunity that won't last. And I also just have a general philosophy, and this ties back to fascination and curiosity. Like, in sports... or even, let's say, the ballet. Would you ever look down upon one of the greats because you read that they practiced more than the other person? We don't ever apply that lens to careers, which I think is a bit unfair.

Because we celebrate the fact that Michael Jordan or Kobe Bryant worked harder than anybody else. We celebrate it there, so why don't we celebrate it in AI? I think there's a bit of an unfair... lens that we use on careers.

I'm just going to put my, like, pragmatic hat on for a second, where, if a lot of your advice is geared towards, you know, going where the action is and following your passion, following your interests, but then someone is sitting there saying, like, 'I'm literally just trying to make it to next week. I'm just trying to make it paycheck to paycheck,' how do you ground your advice to the reality that maybe a lot of people are facing right now in America?

Well, I'm going to mention two things. I want to address the question directly, and then I want to tell you about the foundation that I'm launching simultaneously. So I think it is hard. I think there are a lot of people that have limited ability to – to change what they're doing. They may, you know, some people put themselves in that situation. I think young people, I ended up in New York at age 27 and I had a lot of friends that, that, you know, got a place in the Hamptons, kids in private, like they made all these decisions that locked themselves in because they were spending right up to their salaries. So one thing you can do to increase your flexibility, you know, Danny, when he became a restaurateur, took a,

90% pay cut, like, but he could afford it because he saved money from the previous job. So, you know, you can create your own flexibility. Um, you also don't have to, you know, go to the epicenter there. There's, there's many versions of that. There's online communities everywhere that are very purpose-built and you can plug into those. Um, and then let me tell you about the foundation. So I'm launching something called the Running Down a Dream Foundation. It'll be at RDAD.org. It's going to really ramp up next year, so we're still putting the pieces in place. But we're going to take applications and award a $5,000 grant to people that want to chase their dream job but don't have the economic means to do it.

So that's coming. I would also tell you, like, there's a great story in the book about Jen Atkin, who is the most successful hairstylist of all time.

You should go check her out, Tony.

But here's, she went to L.A. with $300 in her pocket, got a job working at the front desk of a salon, and then went to a vocational school in L.A. that's free to learn cosmetology. Like, and so, you know, she was resourceful and looked around and used those things that were available to her. But she had next to nothing, like, like what you just described was her starting point.

Now, you got your MBA from University of Texas, and I'm sure a lot of people listening to this are saying, "Maybe I can get a leg up or pursue my passion by getting an MBA." But I've heard a lot of criticism about it. It's expensive. So is getting an MBA overrated or underrated?

I think it's an awesome opportunity. So there's some data in the book that we borrowed from Dave Evans, who does the Designing Your Life class at Stanford. And I should have the numbers in front of me, but I don't. Five years in, like 40% of people are no longer in a career associated with their major. And like 10 years after that, it's even less. And so a lot of people don't end up working in the area they majored in. And so you may have majored in something that you're not particularly passionate about. You may have figured that out by working at it for two years. Sam Hinkie, who we profile in the book, you know, did this. He was at Bain. He, you know, he read Michael Lewis's book on, on Moneyball.

And he just decided, "I'm going to go to an MBA program as a way to repot myself to go chase this dream of being a sports general manager." And, and it worked for him. And one thing I would tell you about an MBA program is you get, you get out of it what you put into it. If you go in there with an intentionality to learn and maybe to repot or redirect, you can get a lot out of it. If you go in there and just coast, the grading's not that hard maybe outside of Harvard, so you could coast through it. But I wouldn't do that. I wouldn't think, it's not a stamp that's going to change your life. But if you want to go learn for two years and repot, it's fantastic.

Neil, what do you think about Sam?

We're big process trusters here at Morning Brew Daily.

Okay, great. There's a whole chapter on my good friend Sam Hinkie. It's pretty amazing. He read that book and 10 years later was GM of the Philadelphia 76ers. There you go. 10 years later.

And we're still searching for a title or even a playoff.

I see your path in front of you, though. Read the book, Neal. Speaking of your book, and just—this is the process of bringing a book to life—is there someone that you wish you could get one blurb on the cover or the back of your book that you either got or you didn't get? Talk to me about who's the Michael Jordan of book blurbs that you wish you got?

Well, I'm very fortunate. I was really nervous about this, but it turned out, I feel—I've gotten to know a lot of great authors. I have a huge respect for the art and craft of writing. And one of the reasons it took six years was I was devouring books and advice from people to try and make the book as good as it could possibly be. But I lucked out. I've got James Clear, who saw my original presentation and was part of the encouragement to go do this. Jonathan Haidt provided a quote. Jeff Bezos. Adam Grant. It's like a who's who. David Epstein. I got very fortunate.

It's good blurbing. That's some good blurbing right there. Jeff Bezos just reminded me of another question. There's an idea that he advocates for called the regret minimization framework. Oh, yeah, we talked about it. When he was deciding whether to start Amazon or not, he kind of put himself in his shoes as an 80-year-old and, looking back on my life, "Would I regret not making this choice?" How do you think about using regret as almost a North Star to make career decisions?

It relates to that survey we did, right? Because that was measuring career regret. And Daniel Pink, who also provided a blurb, he has a book about regret. And he has this concept called boldness regrets. And he mentions the Bezos thing. And what he has studied, and says it exists in every country around the globe, is the regrets that weigh heaviest on people are regrets of inaction. This is what he calls boldness regret. And as you get older, they're kind of bigger in your brain and cause more anxiety. And he argues regrets can be very helpful because that anxiety should force you to go do this thing. But I think a lot of people never take the chance. They don't feel they have the permission or the audacity.

And part of what I hope to do, like, what will be truly defining success to me is if I unlock that potential by giving people that permission to, to do this thing. So for those that don't know, Bezos came up with this thing. He's walking around Central Park. He's got an incredible job at D. E. Shaw, and David Shaw begging him not to go. And he asked himself, "If I imagine myself at 80, will I regret more leaving D. E. Shaw and maybe, you know, screwing up my finance career or missing out on this chance to be an entrepreneur?" And he said immediately it was easy for him. And by thinking in that frame—and I, I've mentioned this to executives along the way in the venture world, like, like people don't sweat that much making a mistake.

Like, you, you get over it, you move on. And so why not take the swing, you know?

Speaking of regret, your Longhorns are not in the College Football Playoff this year. No, there's a point to this question. It's a very controversial process. A lot of people are angry about their teams not being in, and they think it's a broken system. So if someone put you in charge of the NCAA, how do you fix what's going on in college football?

Well, there's a lot. I mean, there's so much in that question. So the first thing is, I was very nervous about the arrival of NIL, especially unstructured NIL, and the open transfer portal, both of which don't exist in any pro sport. And I worry a lot, not about the kids at the top, but I worry about the kids at the bottom. Like, I think there are a number of humans in all the different sports that took an incredible life experience away from D1 athletics and even all the way down to D3 athletics. And I worry that the end result of all this might be several schools just terminating those programs or those efforts, which isn't a direct answer to your question, but I, I worry about that. I do think you're going to see the big, either with or without the NCAA, I think the big conferences are going to try and establish a rule set.

I don't know if the judges will let them, but you literally have a process right now that's worse than any pro because there's no salary cap. There's no limit on walking away. And so it's really random. In terms of the playoff itself, you know, let's go to 16, maybe 32. Why not?

It's actually, this raises an interesting Venn diagram of two of your interests. You've talked a lot about regulatory capture and how it often ends up benefiting the incumbents in industries. So when you're talking about putting more regulations onto college football, I'm wondering if those two are diametrically opposed to each other. Would more regulations around NIL just end up benefiting...

Alabama again, or do you think that it's a different case when it comes to college football? Well, I mean, to your point, there, there's been, I think, unexpected parity since this happened, and I think one of the things that's been really hard to hold on to is your second string. So one of the things that made teams like Alabama so dominant is the second string and third string were all incredible athletes. And now those people will go somewhere else and get playing time. So that probably has led to parity. Um, I don't know that the path we're on is sustainable. Like, I think a number of, you know, a number of, of the, the Board of Regents are going to just call quits to the, to the, the game that's escalating.

We got one final question for you, Bill. How do you think your life would be different if you were five-nine, instead of six-nine?

It's a good question. I mean, I've read the books on height. I mean, I wouldn't have had the experience I had riding the bench at Florida, which I think shaped me in some, you know, weird way. And, you know, if you read those studies, you know, it could impact other opportunities as well. I don't know. I would have been much more comfortable on commercial airlines. I can't imagine.

That's tall people problems, you know, tall people problems. All right, Bill, thank you so much for joining us. This was a really fun conversation. Everyone listening, make sure to check out Running Down a Dream: How to Thrive in a Career You Actually Love. It drops in February, so keep an eye out for that. Bill, thank you so much. This was great.

Thanks to both of you.

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