Bill Gurley: Legendary VC Rethinks Career Advice in 'Running Down a Dream'

Bill Gurley (0:01)

The Power of Mentorship As we get older, the regrets of inaction weigh more on our brains than the regrets of action. Regret of action is I did something that didn't work out, I made a mistake. Humans are amazing at forgiving themselves for those things. But the thing you never tried eats away at you, this kind of path untaken. One of my core objectives of the book is to give people the permission, the confidence and the methodology to go try, to go try that thing they've always wanted to do.

Frank Blake (0:33)

Hello everyone and welcome to Crazy Good Turns, the podcast that recognizes and celebrates people who do amazing things for others. And I'm your host, Frank Blake. I'm thrilled to welcome Bill Gurley to our show today. Before we get into his remarkable career, and it is a remarkable career, I want to tell you about his new book and why I think it's a crazy good turn. If you looked at a quick synopsis of his book, which is titled Running Down a Dream, might sound like the kind of advice people often distrust. You know, the sort of follow your passion, chase your dream, do what you love kind of advice. And that advice, taken too simply, can get people into trouble. And yet, Bill Gurley has written a book on career and work that I find thoughtful, practical, genuinely helpful, and wise. Certainly, Bill has the credentials to offer great advice. He is one of the most successful venture capitalists of our time. He's known for early investments in major companies like Uber, Grubhub, and Zillow. And he's widely considered one of the greatest technology investors of our time. So if he had wanted to write a book about investing or technology markets or his own career, plenty of people would have read it and you'd understand why he'd sit down to write it. But that's not what he chose to do. Instead, he wrote Running Down a Dream, a book that tries to help people find work that truly fits them. Not through cliches or magical thinking, but through stories, principles, and hard-earned wisdom drawn from people who built extraordinary careers in all sorts of fields. And as you'll hear, Bill is not arguing that everyone should recklessly chase some fantasy. He's making a more interesting case than that. He argues that fascination matters, that engagement matters, that people do better work, keep learning longer, and build stronger careers when they're deeply interested in what they do. During our conversation, Bill shares the principles that help the world's most successful people, from musicians like Bob Dylan to restauranturists like Danny Meyer. Start from the bottom rung. We discuss why the safe career path might not be safe at all, the power of peer groups, and why sharing your best ideas with others is better than keeping them close to the vest, and why a simple thank you note might be the most powerful tool in your professional arsenal. I enjoyed this book so much that I want to make sure you have a chance to read it. We're giving away 50 copies of Running Down a Dream to our listeners. To enter for a chance to win, visit crazygoodturns.org/gurley.

That's G-U-R-L-E-Y. You'll also find the link in our show notes. Bill and I will also talk about The Power of Mentors, and I'll tell you that by writing this book, I think Bill has chosen to mentor thousands of people, perhaps including you. So I hope you'll take the next step and enjoy our conversation with Bill Gurley. So I'm going to start. There's a little preamble to my question because I think your writing and publishing this book is a crazy good turn of its own. Because if you had asked me, okay, Bill Gurley, one of the world's most successful investors ever, is going to write a book, I would assume that book would be, you know, heavy on bibliography, you know, your biography, what you did, all the rest, and how you did it. A lot of investing tips and that kind of stuff. Instead, you wrote a book, and you can correct me, but as I read it, I think your book is really about giving people courage and confidence to pursue a career they love. So if that's a right reading, why and why that topic?

Bill Gurley (4:43)

I kind of fell into the idea about 10 years ago. I was reading a bunch of biographies. I think a lot of people go through a phase, well first of all, you get addicted to reading, then I think if you're addicted to reading, people go through a phase where they read biographies. And I read these three biographies of people from seemingly far away fields from each other, who all started on the bottom rung and were highly successful. And maybe part of the reason why I love being a venture capitalist, seeing the company at the PowerPoint stage turn into a big global phenomena and being along for that ride. I've always had this closet obsession with American Idol. I like this kind of from zero to wild success kind of story. And I put it together as a presentation and I gave it at the University of Texas to the NBA program. They put it on YouTube and a few people noticed it, one of which was James Clear. And so I had a few people, and then I started getting feedback from people that saw it and how it impacted their lives. When I decided to declare victory and hang up my cleats from the venture world, I was thinking through a lot of different things I would do with my time. I stumbled on this book, Strength to Strength, I don't know if you've seen it. Arthur Brooks. And I just decided that it would be way more fun and exciting to go do this book, which could touch a lot more people than to write a book that would help tomorrow's VCs be better VCs.