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

0:00Neal Freyman:Managing media plans for multiple clients can feel like herding cats. Disney Campaign Manager is built for fast-moving agencies looking for one simple ad-buying solution to handle all of their streaming TV campaigns across Disney +, Hulu, and ESPN. Set flexible budgets, adjust on the fly, and optimize for total campaign control across every buy, all in one platform. Get started today at DisneyCampaignManager.com. That's DisneyCampaignManager.com. 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.

0:43Neal Freyman:It's Monday, December 29th. Let's ride.

0:52Happy Monday, everyone. Hope you have a chill final week of 2025 ahead. You know what's not, Trill? 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.

1:14Neal Freyman: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. And make sure you stay to the end to hear what life is like as a person who is 6 '9". But first, a word from our sponsor, Public. Toby, I don't know about you, but it is getting harder and harder to wake up every day with how cold and dark it is. Mornings are just not as easy. I am with you, Neil. But one of the redeeming parts of my morning routine is checking my portfolio on Public.

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2:35Bill Gurley:My day kicks off with a refreshing Celsius energy drink. Then straight to the gym. Pre-K pickup, back home to meal prep.

2:42Neal Freyman:Time for my fire station shift. One more Celsius, gotta keep the lights on. When the three alarm hits, I'm ready. Celsius. Live, fit, go. Grab a cold, refreshing Celsius at your local retailer

2:54Bill Gurley:or locate now at Celsius.com. 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, shout out 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.

3:37So 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.

3:47Bill Gurley:So one thing I would say, like 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 books that are related to people that have thrived in sports in general.

4:35Bill Gurley: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.

5:22Bill Gurley: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 in the book, and the reason that chapter's 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, you know, this subject and to study it?

6:15Bill Gurley:And I like to say, you know, if you have three episodes of Breaking Bad left, would you study this instead? Like, 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.

6:36Neal Freyman: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 were advocating for in your book?

6:51Bill Gurley:Yeah, 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 this mindset where you want to push kids towards economic safety. And and that meant jobs where you know that the unemployment's low and the salaries are high.

7:35Bill Gurley: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, 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.

8:18Bill Gurley: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 cliched, 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.

8:54Bill Gurley:And when Seinfeld gave the, the, the commencement speech at Duke, he made fun of the word passion, but then he reoriented it around the word fascination. I think it meant the same thing. I, you know, 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 know, you're going to spend about 80 ,000 hours at work. And I've met people and you and I are 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

9:39Bill Gurley:and 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.

10:23Bill Gurley: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. You know, and there's no athlete, you know, 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 gonna excel past the vast majority of other people.

11:17Neal Freyman:Yeah, 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.

11:35Bill Gurley:And by the way, one thing I should have said related to that, don't, you know, don't do what you love or don't, don't chase your passion. Um, the job satisfaction numbers are at an all time low. The, the, the Gallup poll numbers are like, like only 40 % of people consider themselves engaged at work. This whole phrase, quiet quitting. There's actually people who are like actively disengaged at work that are like trying to harm the organization. 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.

12:12Bill Gurley:So I think people aren't ending up in the right place, you know. But to your specific question about this advantage, like, if you, you know, 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, you know, find your way to be so curious about what you're doing, that you're constantly learning people, people that I profile, the first profiles on Danny Meyer, the amazing restaurateur in New York City. And 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 but but when when when people read the book you'll see that they're i i understand how you can say like yeah you're eating at fine places in europe but but they take copious notes they 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.

13:23Bill Gurley:And it's just, 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?

14:02Should people still follow their passion if AI is better at it than they are?

14:07Bill Gurley: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 tool set. Like if, you know, if you come to the workplace and can't use Word or Excel or PowerPoint or email, like 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, like understanding AI in your field is the best way to stay at the forefront of what's possible.

14:50Bill Gurley:and could accelerate you to the front of the line by being the first person that does that.

14:56Neal Freyman:You did say on another podcast, Tim Ferriss' 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?

15:11Bill Gurley:I was talking to my friend Mike Movison 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 most intelligent encyclopedia of all time.

16:02Bill Gurley: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 chat GPT, 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 divide it into two pieces.

16:46Bill Gurley: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 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.

17:33Bill Gurley:I mean, people are flattered to be told that you're inspired by them, right? And 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.

18:11Bill Gurley: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.

18:24Neal Freyman:Neil, reach out to Taylor Swift. See what she thinks about your background. 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?

18:43Bill Gurley:Well, I certainly – well, one, the industry I come from, venture capital, I've had a philosophy my whole life that it bends towards youth. The disruptors of tomorrow are frequently in the 20s, and your ability to associate with them gets harder as you get older. and 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.

19:23Neal Freyman:We'll be back with more Bill right after this. We're the Hartford. With decades of experience ensuring millions of unique small businesses, when it comes to your small business insurance. Thank you. One size absolutely does not fit all. Get a quote or find an agent today at thehartford.com slash small business. Get in the game with the college branded Venmo debit card. Wreck your team with every tap and earn up to 5 % cash back with Venmo Stash, a new rewards program from Venmo. No monthly fee, no minimum balance, just school pride and spending power. Get in the game and sign up for the Venmo debit card at Venmo.com slash college card.

20:04Neal Freyman:The Venmo MasterCard is issued by the Bancorp Bank NA. Select schools available. Venmo stash terms and exclusions apply at Venmo.me slash stash terms. Max$100 cash back per month. Principle number five in your career playbook is go where the action is. In your view, where is the action right now?

20:23Bill Gurley:Well, I mean, that whole chapter is about identifying the epicenter of an industry. 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 the benefits that accrue to you, you know, by being a songwriter that lands in Nashville or an entrepreneur that lands in the Bay Area are immense. Like, and, and all the learning opportunities go dramatically higher. The optionality gets, gets, gets really enhanced. Like 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.

21:12Bill Gurley:I was super lucky to meet this person. Like if you're where that world is, the odds of the, that happening go up and up and up and up. And yeah, I think, I don't know who said that luck is when preparation meets opportunity, but opportunity is enhanced greatly. I mean, you guys are in New York, you know, this like, like stuff happens because you're in New York. It 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?