Open Book with Anthony Scaramucci - The Career Advice That Ruins Lives (And What Actually Works) - Bill Gurley

Episode Date: March 17, 2026

Today on Open Book, I’m joined by legendary venture capitalist Bill Gurley, whose new book Runnin' Down a Dream challenges a lot of the career advice we give young people. Bill argues that the safest career path isn’t the “safe job” at all—it’s finding something you’re genuinely fascinated by and chasing it relentlessly. We’re going to talk about curiosity, regret, and how to build a career you actually love. Bill Gurley is a general partner at Benchmark, a leading venture capital firm in Silicon Valley. Over his venture career, he has invested in and served on the board of such companies as Nextdoor, OpenTable, Stitch Fix, Uber, and Zillow. Gurley has written about technology and other subjects on his popular blog, Above the Crowd, for over 20 years. This is a sensational book. Get your copy of Runnin' Down a Dream: How to Thrive in a Career You Actually Love here: https://amzn.to/46X4rEc Anthony Scaramucci is the founder and managing partner of SkyBridge, a global alternative investment firm, and founder and chairman of SALT, a global thought leadership forum and venture studio. Pre-order my next book, All the Wrong Moves: How Three Catastrophic Decisions Led to the Rise of Trump, out on the 17th of September in the UK and the 22nd of September in the US: ⁠https://linktr.ee/anthonyscaramucci⁠ Learn more about your ad choices. Visit podcastchoices.com/adchoices

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And so my argument is you're going to end up working 80,000 hours in your life. Why not do what you love? And I fear that our society has been steering people towards, quote, safe jobs, which in a day of AI may not even be that safe anymore. And I would argue the safest thing you can possibly do is find a career in something that you're totally fascinated with. And the reason is all the techniques that tell you how to be the most successful thing you can possibly be, they're all 10 times easier if you're fascinated and in love with the subject matter. Everything gets easier. and you get energy rather than it costing you. Welcome to Open Book.

I am your host, Anthony Scaramucci. Joining us today's Bill Gurley, the book is phenomenal, running down a dream, how to thrive in a career you actually love. Don't all of us want to do that. But Bill, I've been following your career from a distance. It's a real pleasure for me to have you on our podcast together. And I'm a big book lover,

and this is going to be on my recommended list going forward for young and old people. There's so much in the book. I want to go to something that I love, which is getting a book published. So let's start right there. How does it feel to have this published now? It's a bit overwhelming. This was a passion project on the side for me, not my day job.

And it was born out of a presentation I gave eight years ago at the University of Texas. and once it began to take life as a book, for reasons that we could dive into, I took it very seriously and did a ton of academic research, talked to a ton of experts. I really wanted it to be great. And so it took about five years, literally, not full time, like in the background, to get it burnt. And then the thing I had no idea promoting the book is quite tedious. Yeah, it's hard. Now listen, I've done a couple more. You've got to get your personality out there, but you're doing a hell of a job.

You know, I've seen you on a couple of different podcasts. I've listened to you. I think the story about James Clear observing you when you were at the University of Texas at the McCombie. Yeah, he found the video on the YouTube and reposted it, which gave me some confidence. You know, he's perhaps the best-selling author in the self-help categories. Well, him and Mel Robertson. He's written a phenomenal. book about habits, but you have recognized something through pattern recognition, but there's also

something else that you're doing, which is evident in your book. You have a tremendous amount of self-awareness, which is, if you don't mind me saying this, because I've worked on Wall Street for 40 years, venture capitalists and Wall Streeters typically don't have a lot of self-awareness Bill Gurley, okay? So this is something that you have, which I give you an enormous amount of credit for. So tell us about your insights from your own self and tell us how you saw these patterns. And that's why the book, I mean, this is why the book is so good, by the way. So tell us about that. Yeah. So I was, there was a period in my life. I'm a big book fan as well where I was reading a ton of biographies. And I finished this third biography and saw a through line between it

and two others in completely different fields. And these were all people that started on the very bottom rung of the ladder, but had high intent. So they wanted to be successful in the category, starting at the very bottom. And I noticed that they all did very similar things. And some of these things are things that aren't generally recommended to young people. I think we also live in a world, at least in North America, where our path to and through college has gotten super intense and kids are just way over scheduled and they don't really have the opportunity. And others have written about this. Heights written about this.

Rick Rubens talked about it. They're so over scheduled that they just don't have the time to find what they love and to really fall in love with something that they can turn into a career. And so I wrote this book with just one objective in mind, which is to help unlock human potential. So I want people to believe they can go do something that maybe their parents or some advice. I sir told them not to and have the motivation and the methods to go do it. You know, you're an entrepreneur. I've been an entrepreneur in my career.

And so I've gotten some things right, Bill. I've gotten some things very wrong. I've had career setbacks. I infamously went to the politics for a little while. I got my ass fired after 11 days. So I've had my bumps and scrapes along the way. but there's something that you write about in this book that I want you to address, because I do believe this. And this is something that you cite Daniel Pink's research in this about the regrets of inaction.

So that's me. I feel like whatever's happened has happened. I'm willing to accept it primarily because I've been on the playing field, throwing interceptions and a few touchdowns. So talk about the regrets of inaction as you beautifully write about it. And you mentioned earlier, you know, career regret. We did a survey, first on SurveyMonkey, and then we did it again with Wharton people analytics because we wanted to make sure we got it right. Where we asked people that had been to college, you know, if you start your career over again, would you do it differently?

And in our original Survey Monkey, 7 out of 10 said yes. With Wharton, it was 6 out of 10. It's still a vast majority of people. Daniel Pink in his book, The Power of Regrets, notes that humans dwell on regrets of interest of action. He calls them boldness for regrets. These are things you didn't try. And the older you get, the more they weigh on you. Humans are fabulous at forgiving themselves for mistakes, kind of what you just walked through. Those are action mistakes. We're like, oh, that's all right. Water under the bridge. I learned something and you move on. But the thing you never tried is the thing

that he's as you get old. So young people listen to this podcast and thank God for that. So I want you to grab the young men and women that listen to this guy, grab them by their shirt, grab them by the collar, and shake them a little right now, and give me the message, Bill. Yeah, so first of all, we have a phrase in the book, life is a use it or lose a proposition. And I think young people don't see the end of times. Like, it seems very far away, but older people really, it weighs. By the time you're 40 or 50, I think it weighs on you. And so, My argument is you're going to end up working 80,000 hours in your life.

And why not do what you love? And I fear that our society has been steering people towards, quote, safe jobs, which in a day of AI may not even be that safe anymore. And I would argue the safest thing you can possibly do is find a career in something that you're totally fascinated with. And the reason is all the techniques in the book that tell you how to be the most successful, thing you can possibly be, they're all 10 times easier if you're fascinated and in love with the subject matter. Like, everything gets easier. And you get energy rather than it costing you energy. So I would also tell them, I would also tell them one last thing. I would just tell them, if you don't know what that is, that's completely fine. Don't stress out about it. Just keep trying

things. Take shots on goal. See what really interests you until you find it. And the whole chapter, in our book called Chase Your Curiosity is about that journey. So it doesn't presume you know this going in. I mean, it is fascinating. The reason why I was going to step in is related to something that you write about, which is the ethos of the reality of most people can't afford to be wrong. And again, it's something to do with their self-image, but it could also be an economic reason.

You know, somebody like me at the early part of my career, I didn't have the guts to start my own business. In fact, I wrote down the day I graduated from law school bill, I said, I'm going to have my own business, but not until I pay off all the school debt. It took me seven years. And I worked at Goldman Sachs for seven years. When the debt was paid off, I left the start of my own business. And by the way, by the way, it was scary even then without that financial rock or that boulder on my shoulder. So how do you get through that?

Tell us about it. I think it's difficult. I would tell you that the, so the, for your listeners. the books divided into profiles and printables and they interleave and alternate. And the profiles are stories. And a couple of the stories, people have zero dollars when they start. Certainly, Bob Dylan's one of the stories when he went to New York. You had $10.

It's a great. The Dylan story, which even though I saw the movie, I didn't really see in your context. Yeah, they missed this part. Most of our coverage is pre the movie. I love the Dylan story. I want to get to the Dylan story. but weave it in with this. Yeah, but Jen Atkins, I was going to say,

Jen Atkins went to New York or L.A. with $200. Now, your situation's worse because that is negative money, which is more of a handcuff. And I would tell people, one thing they can do, and AI can be super helpful on this, is you can plan and imagine without actually doing something. So, and I think the more you do of that as an exercise, the more confidence you will build

that you could possibly go in that direction. Dave Evans, who wrote Designing Your Life, talks about this as a way to find which way you want to go. He says like battle card, three or four scenarios. But it sounds like you knew what you wanted to do. So literally as a hobby at home, like have AI help you build a game plan.

Like, what are the first five steps going to be? How can I do this with this constraint? And I'm not saying jump tomorrow, But I think the more that you visualize what's possible and think through the difficulties, the steps you would take, the more confident you're going to have in taking that leap. Yeah. I know this. I think it's really true. And I always tell young people that it's not as scary as it looks.

And that's the weird thing about it. I remember when I left Goldman, one of the old partners at Goldman, still a very close friend of mine. He's in his 80s now. says, you know, you'll figure it out. And, you know, and you know this expression. Entrepreneurs, they jump off a cliff. They're trying to build an airplane on the way down. But you figure it out. And I think that's something that we need to tell young people that believe in yourself, recognize that you have levels of resourcefulness and energy for the things you're passionate about way more than the fears. You know, the energy and passion can overcome the fears. Tell us about Bob Dylan, though, sir. I thought that that was. Because to me, you know, when I think of your book, I'm going to think of so many great ideas and concepts, but it's really the Bob Dylan story that resonates with me the most. Tell us about Bob Dylan.

So this isn't covered in the movie. And it is, there is some detail in the Scorsese documentary. But Dylan is a, and always was going way back to when he got started is a historian. He liked, and he's insanely studious about music. And so when he got to Minneapolis, he started studying folk music. And I have a high confidence level based on what I've read, that he knew more about folk music than anyone else in Minnesota when he left for New York. And the friends they talked to, he would sit in record stores that had these listening booths back then, and he just went over it and over and over it. And now, you know, obviously he's so successful.

You can see this. He did a podcast for a while where he went through different genres of music and you can just see how much details in his brain. And then he released this book, Coffee Table Book recently, about the 50 most impactful songs of all time. And you just see that, I think people have a perception that he's just sitting there writing his own songs.

But the guys has just studied everyone under the sun. And the second tenant in the book is hone your craft. It's all about continuous learning. And it's a vector that I see run through all the most successful people. You know, do you go home at night and study the thing you love? And does it feel like an alternative to watching Netflix? Yeah. So, I mean, that's the follow-up question.

Do you think the curiosity-driven path that he was on that you wonderfully describe in this book is harder in the attention economy that rewards you know it rewards breath over depth as an example. Potentially but I would tell you that you know a lot of people have brought up the threat of AI recently and I realized I didn't I wrote this I started writing this book way before the AI wave but but most of the

most of the people that are just hyper curious about their field they act like artisans or craftsmen and part of what's really cool about an artisan or a craftsman is they're really studying the nuance at the edge of the field. And that's the stuff that's not in the AI model. You know, if you just go to school and learn all the rote stuff and you think you have a defensible, you know, differentiation because of that, that's the stuff that AI can do really great. And the thing that the experts do are these artisans do is really study what's on the edge and the nuance that's out there. And they're able to

to use that confidence in the nuance to really differentiate themselves. So I am I'm certain that now there was Mark Cuban had a great quote the other day. He said there are two types of people in the world, those that use LLMs to learn faster and even more and those that use LLMs to avoid learning. And I thought it was pretty profound. Like if you want to be studious about something, there's never been a better time on the planet. These tools will allow you to learn as fast as you possibly want to go. But you have to have the interest, as you said, if you don't, if you don't, you don't get there. But this is, this goes back to the test being, are you fascinated with this? Like, you know, it's a good, it's a good segue into what you talk about in

terms of people wanting success or people just excited about building things, right? It's sort of the same sort of concept. So tell us about your observation as a venture capitalist of founders that you've met. You can tell early on, can't you when someone's generally, you love with gold, right? Founders have two things that are, first of all, they just have a super high motor. They're very determined, at least the best one. They're like hyper-determined. they're going to do this come hell or high water.

But the second thing is they are hyper curious about what they're doing. And so almost the way that a founder or entrepreneur takes advantage of some new technology wave is they go understand what it's capable of more than anyone else. So just as I'm talking about maybe Bob Dylan did at folk music, they're doing that with the new AI wave. And they did it with the mobile wave and the internet wave. These are the people that are on that edge studying that nuance and exploiting. Yeah, I mean, see, to me, that's the real love, right? You know, I'm, I like building things and I have intellectual curiosity and, you know, they'll get me wrong.

I'm in it for success. I'm not saying I'm not, but I'm not, doesn't overly inspire me. What inspires me and one of the reason why I do this podcast is that I love talking to authors. I mean, the fact that you took the time to synthesize and put all of these thoughts down for all of us, you know, I used to tease people, Bill, you and I are roughly the same age. I used to say for $10, you can read in 10 hours, 10 years of an author's experience. Now, with inflation, it's probably $30 today. But you get my point. And it's also about the peer group.

You know, I always tell my kids, you're the weighted average of the five people you hang out with. You write a great, your theme about the power of peer groups and the people you surround yourself, which, you know, how much of long-term success is talent? and how much of it is just getting yourself into the right space and into the right peer group to help propel yourself? Look, I mean, I think having written this book, I would hope one thing people will walk away from is the belief that the techniques that I have in here don't require some excessive amount of intellectual power or some natural talent to go do them. Most of the people in the book are hyper fascinated by their field. They study their butts off, and they collaborate and connect in multiple ways with both mentors and peers. And my favorite principle in the book is this one on peers, because I think a lot of people say what you just said, like being a good friend group, but I don't think they are taught to proactively create a peer group to help them along their career path.

And we have some wonderful examples in the book, but I think too many people, come out of the college experience sharp elbowed, mainly because it's so competitive. Like, you know, you're trying to get good grade, you're trying to get the job, someone else couldn't get. But what I would tell people is the world's not zero sum. In any field that we're in, there's many, many winners, many great winners. And if you can find a group of people that are on the same journey you are, they're on the same rung of the ladder, climbing up, and you guys can share and trust

one another. It is, it is just so wonderful. You get so much extra horsepower. You get shared learning across the group. You get to share each other's networks. You get a support group on bad days, which is, there's a lot of them. And it's just, it's fantastic. And I think this is not, once again, this is a technique that's not taught a lot. I think, I think this is maybe the first book that's really pounding the table on. But it can be really powerful. Two other themes. If you don't mind me go into these.

No, go for it. Sam Hinky. You give a great example of him. Okay, it's a precautionary tale, but it's really about trusting the process. And let's go to McConaughey, who I think is a philosopher king. You know, in addition to being a great-looking A-list actor,

his depth and his insights. And I love his writing, by the way. And so sounds like you guys. are close and he says something which we have to say to our kids every day and even to ourselves don't half-ass anything right I guess his dad said that to him so take those two guys tell us a little bit about those two guys and the impact that they've had on you yeah so I've gotten to meet Matthew here in Austin where I relocated a few years ago um his book greenlight is oddly I think has a similar objective as my book which comes from a very different place

He uses the metaphor of a green light to be no-win, knowing you should put the gas pedal and run at things. And, you know, I thought, it's funny, I got to meet Rick Rubin through this process. And his book, The Creative Act, is very different in my book, but I think it has the same goal, which is to encourage people to get out there and do their thing, you know.

And there's this great anecdote in Matthew's history where he told his dad he was going to be, be a lawyer and he was at the University of Texas pre-law track and met some people at the film school and had a change of heart. He wanted to go do this thing and he was afraid to tell his father but when he did his father said famously now don't have acid and he said it was the last thing he expected his father to say and the best thing his father could have said because it wasn't only encouragement but it was responsibility he called it rocket fuel and that I mean it's kind of where I hope the book can do. The concluding chapter of the book's titled, It Ain't Easy. And I don't,

I don't want anyone to think that, you know, you can read this book and everything just comes at you. Everything's hard out there. But one of the reasons you want to be fascinated by what it is you're doing is so that you have the ability to go do all these pieces that bring it all together. And so, you know, I think he's a great example of someone who's really, risen up, but also gives back. That's another principle we have in the book. His writing, I think, is intended to help and motivate people. And yeah, he's a great, he's a great role model for a lot of the younger adults out there. Well, listen, I mean, it's just such great messaging. It's a, it's a short, you know, Bill, it's a lot of dense information in a short book. I mean,

this book took me a few hours to read. And I was like, wow, this is great. And even, you've got your book lists in the back as well, which I, I tell people they should look through and I've read some of these books and now because of you, I'm going to read more of them. But if I said to you, I get a kid in front of you and I said, okay, there's one thing that I would like you to do differently tomorrow. Okay, you just finished my book. They come and sit down and they're right there in your office and you say, okay, there's one thing I'd like you to do differently tomorrow. What is that?

What would that hope be for you? For that person. especially with the young adult is just to start um start thinking about contemplating what it is that they're truly fascinated with like that's that's the lane that if they can get in i think they're going to have just a wonderfully fulfilling life and i i'm one of the things that motivated me right to book anthony i'm fortunate enough that that people that saw this video online many years ago some of them shifted careers and have reached out to me.

And they're triple pink. And like knowing that you had this chance to get people into that lane where they're just so happy and so fulfilled. A lot of the podcasters I've met are in that lane. They're thrilled to talk to people and be excited and learn all the time. And so it's doable. And there's a ton of examples in the book. I'm glad that it went fast for you.

The way the stories were written were intended. to make it like super consumable. It was it was very consumable. I think, you know, I, I think of my, my 26-year-old son, who is a creative guy, want to be in the film industry. So, okay, he's in the film industry, he's produced two films. And he got the chance yesterday to tour George Lucas's new museum, I guess, of narrative art is what it's called.

That's awesome. And he said to me it was the greatest day of his life, Bill. How good is that? How good is that? And I want to share that with people because he is not following me in my career, nor did I ask him to. This is something he really wants to do. And I always tell people that Mel Brooks is my spiritual advisor. I've never met Mel, but Mel Brooks at 99 has said, relax.

None of us are getting out of here alive. And I think that message in this book is so vivid, you know. And look, if a kid goes in a museum and it's the best day of their life, that is the right direction. Right. Because most young people go in museums and don't have any positive experience whatsoever. But, I mean, look, he's walking around in the museum with one of the greatest filmmakers of all time. And, of course, Anthony, my son, Anthony, wants to be a filmmaker. And George Lucas puts his own around.

You know, making film is very hard. Yes. Okay, but you know what? So is Wall Street. So is venture capital. But if you like it, you can take the body blows that happened. Oh, it's so great. When you're running down a dream, you're going to get your ass kicked a few times.

And that's the big message of this book. And I got to tell you, I was inspired by the book. And I'm grateful to you for writing it. And thank you for coming on the show. So we're down to the five words. Okay, so if you ever listen to my podcast, my producer and I come up. Just real quick, especially if you're going to have some listeners or audio only. When you were telling me that story about your son and the museum,

I had a huge smile on my face because that type of fascination is exactly. Now that I've talked to so many young people, that's exactly what you're looking for. When you can see that and then blow more wind behind his seat. sales like that's just so great. So thank you for sharing. Yeah, well, 100% but that's why I brought it up because it's elements of that is right here in your book. So all right, so we have five words, Bill. I'm going to say the word, a little bit of a Roshad test. You give me a sentence or two. Okay. All right. And we more or less pull these words from your book. So if I say the word regret, you say, does it have to be a single word? No, no. Yeah. Yeah. I just, um,

A stream of consciousness. It's avoidable. It's avoidable. Like, start to read my book, first of all, but start to think about how you can do that thing that's weighing on you. I think you can't. I think, and the tools have never been better. Like the methodology in my book, the AI tools that are out there for learning and connecting have never been. This is the best time in the history of the world to go chase your dreams.

You know, so fascinating. is when you say the word regret or I say the word regret, I think inaction leads to regret. Yeah. I feel like, you know, I've done some things well and some things not so well, but at least I'm acting. Yeah. So get there, get in there, start acting.

I love it. I love it. Okay, I say the word dream, Bill. You say what? Like possibilities. I go back to this word fascination, which I actually borrowed from Jerry Seinfeld, but like if you are just hyper fascinated by something,

I want anyone out there to contemplate and hopefully believe that they actually can do it in a career. All right. I love that. And that's the whole reason, the whole synthesis of the book. What about passion? I say the word passion. The word has become a bit of a cliche because people say it so much with a career. And that's why I tried to use the word curiosity.

the Seinfeld word fascination. Like the real question is, are you curious about it to a level where you study the history? You know, like want to understand the nuance. Study all the greats. You know, like do you naturally want to study the greats like your son does with George Lucas?

If you do, I think you're pointed in the right direction. That may not be passion. Like, it requires more than that. Silicon Valley. Special place, man. Special place. There's a chapter in the book we didn't talk about, the title Go to the Epicenter.

And there are a few industries where there is a geographic nexus. And if you get to that place, you will discover that lots of the parts that are highlighted in my book accelerate. And you should be unfearful of that step. If you know you're pointing in the right direction, you should want to get to that place as fast as possible. So, you know, it's interesting because I, you know, look, I've been out in Silicon Valley a lot, but it's not my place. You know, Wall Street and the financial center of New York has been more my place.

But what I would say about Silicon Valley for me, I'd like Silicon Valley to stay Silicon Valley. Yeah. You know, we've got to get the right policies and we've got to get the right, you know, ideas. around government so that we're not everybody leaving Silicon Valley and turning it into Austin. That would be my recommendation. Okay. Last two words, and I'll give you the last word. Okay, Bill Gurley.

Well, I mean, that's a hard thing to talk about yourself. My story is embedded at the back of the book in the epilogue and my version of my story. and I feel very fortunate to have found my way to my dream job. It took two stops along the way that I think were building blocks. They weren't wasteful. I was an engineer for just over two years and then I worked on Wall Street for four years. But I found the way to my place. And so I feel very fortunate to have had that experience.

You know, at this point in my life, I'd like to give back. I'd like to be impactful. this book is the first step in that journey. And yeah, that's where I'd leave it. Well, listen, I really appreciate you and thank you so much for coming on. The title of the book is Running Down a Dream. It's a great cover, by the way. It had a life and a career you actually love by Bill Gurley.

Thank you so much for joining us today on Open Book. Thanks for having it. When a country's productivity cycle is broken, people feel it in their paychecks, their communities, their futures. What does this mean for individuals, communities, and businesses across the country? Join business leaders, policymakers, and influencers for CGs' national series on the Canadian Standard of Living, Productivity and Innovation. Learn what's driving Canada's productivity decline and discover actionable solutions to reverse it.