For nearly three decades, Bill Gurley has been one of the most influential voices in Silicon Valley — a general partner at Benchmark whose early bets on companies like Uber, Zillow and Stitch Fix helped define what modern venture capital looks like. Now that the native Texan has moved to Austin and stepped back from active investing, he’s channeling that same pattern-recognition instinct into something else: a book, foundation and policy institute focused on issues he thinks he can actually move.
The book is Runnin’ Down a Dream — a nod to Tom Petty, as well as the argument that following your passion isn’t just romanticized career advice, but a real competitive strategy that’s becoming more urgent as AI rapidly reshapes the workforce. The foundation, which he calls the Running Down a Dream Foundation, will award 100 grants of $5,000 a year to people who need a financial cushion to take the leap they’ve been afraid to take.
We caught up with Gurley to talk about it all—including what he thinks about the somewhat surreal reality that several of his former tech colleagues now wield enormous influence in Washington, why he thinks the 996 grind culture that many young founders have embraced is less alarming than it sounds, and what AI really means for your career. The following has been edited for length and clarity. Our full interview with Gurley will appear on the TC StrictlyVC Download podcast on Tuesday.
Why write this book?
I went through a phase where I read a lot of biographies—of people from very different fields, different time windows—and I started noticing patterns the way I would notice patterns in an emerging market. I wrote them down. A few years later I was invited to speak at the University of Texas, dusted off my notes and built a presentation. Posted on YouTube by James Clear – who wrote Atomic clothing – noticed it and posted it. This got me thinking about the book. And as I went through my own process of stepping away from the business and thinking about what I wanted to do next, it became clear that I didn’t want to write about VC or Uber or any of that. I wanted to do something that could have a bigger mission.
Your research with Wharton found that roughly 60% of people would do things differently if they could start their career over. That shocked you. Why?
When we first ran it as a SurveyMonkey poll, we got a seven out of ten. When Wharton and I did it more consistently, we got a six out of ten. One of the things that strikes me is that we have a phrase in the book – use life or lose the design – and when you’re young, it’s hard to have that framing. It’s hard to fast-forward through all of your time and recognize how precious it is. Daniel Pink has done a lot of work on what he calls regret of inaction – the thing that weighs on people the most as they get older is the thing they haven’t tried, the stone on the stone. This is true across multiple geographies and cultures. And I think many well-intentioned parents feel more responsible for creating economic stability for their children than encouraging them to truly explore their passion. Especially with artificial intelligence, it might not have been the right thing to do.
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Exploring your passion sounds like simpler advice for people on a financial track. What do you say to someone who works paycheck to paycheck?
A few things. First, the book profiles people who started at the very bottom and rose to the top – (celebrity hairstylist and entrepreneur) Jen Atkins moved to LA with $200 in her pocket. There is nothing in the book that says you need to start anywhere but at the beginning. Second, if you’re living paycheck to paycheck, I wouldn’t recommend you quit. I would suggest you use your free time to create a little document on your phone about what could be. Learn. Prepare to jump before you jump. And thirdly – this is why I am starting the foundation. The last page of the book talks about it: we’re going to give 100 grants a year of $5,000 to people in exactly that position, who can convince us in their application that they’ve thought long and hard about where they want to go, but they need a little help to get there.
For years, you’ve been outspoken about regulatory capture—the idea that big companies use regulation to entrench themselves.
I gave a talk about regulatory capture a few years ago—it was at the All-In Summit—and I said at the time that I was concerned that AI companies would try to use regulation to protect themselves. I think it’s happening now. The flip side is that there are legitimate questions: Jonathan Haidt’s book Anxious generation has been on the bestseller list for almost two years and claims that social media is really bad for kids, and academic research backs it up. People would say we should have gotten ahead of social media and we need to do it with AI. The problem is that the people who are begging the most for regulation in AI are the companies themselves, and that makes me skeptical. There is also a global dimension – if American artificial intelligence becomes entangled in the regulation of individual states and Chinese models run free, we will draw ourselves into bureaucracy. I always ask people: what are your favorite five ordinances of all time and how successful have they been? Do you have any confidence that people at the state level in a random state know how to write good AI regulation that will actually work?
It’s a bit surreal that several prominent figures from your world now have enormous influence in Washington. what do you think about it?
It’s very ironic. If you go back and watch the talk of regulatory capture, who would have thought a few years later that it would be David Sacks (White House Special Adviser on AI and Crypto)?
In 2018, Sequoia’s Mike Moritz wrote in the FT that the Americans will lose to China unless they start working harder. It was controversial at the time, but many young founders seem to have since embraced the punishing work culture here – the ethos of 996. What do you think of what’s going on?
I like it, honestly. I think Silicon Valley got really lazy during COVID – people didn’t go to the office, the culture softened in a way I haven’t seen there in years. And I’ve been to China six times. I know what Michael Moritz was describing when he said we lose not because they are smarter but because they have a better work ethic. But here’s the thing: if you study successful people across many disciplines, we think it’s amazing when an athlete works out 12 hours a day or when an artist works obsessively at their craft. No one is saying Jordan didn’t have a work-life balance. We just don’t extend the same logic to building a company. If these founders love what they do so much and feel that right now is the time to go hard, that’s actually exactly the point of the book: finding the thing that makes you feel that way.
In the book you talk about mentorship. What makes a great mentoring relationship and how do people find it?
The number one thing is to get out of your head this ideal that gets passed around in the self-help world: “go get a mentor,” and everyone runs out and cold calls someone who’s ridiculously tall and unattainable, and that doesn’t work. For all those people who are really out of reach right now, I call them aspirational mentors – create a persona out of them, just like I talked about with the dream job component. Get clips of all the books they’ve written, podcasts they’ve done, interviews they’ve done and study them. You can learn a lot from people without actually talking to them, especially in the modern age. And then for your real mentors, go two levels lower than you thought you’d be aiming. Discover someone—tools like LinkedIn make it so easy—and be the first person to ever call them up and ask them to be a mentor, because they’ll be flattered. They will be flattered that you knew who they are. Imagine someone getting their first call to become a mentor. It’s a great feeling. You will have much more success with this interaction than if you shoot too high.
I’ll tell you a funny story: I started getting so many calls from people wanting to break into the business that I wrote a three-page PDF called “So You Want to Be a VC,” and on the third page it was basically hidden—go to X, go to Y, go to Z, come back and tell me how it went. The number of people who actually talked to me after getting that document was a fraction of the number I sent it to. It’s funny how much it thinned out when you gave them a little homework.
You started working on this book before the effects of artificial intelligence were clearer. Does it change the way people should think about their careers at all?
If you go the traditional route—going through the career center at your university, signing up for a list, waiting for a recruiter to sit down with 30 people in 20-minute blocks—you look like a cog. You look serial. To this group, AI looks scary, and maybe it should. But if you’re forging your own path using the techniques in the book and becoming what I call a one-of-a-kind candidate—someone whose path looks completely unique because you’ve built it on purpose—then every tool in this book is AI-enhanced. Learning has never been easier than right now, in the history of the world. If you’re running towards it, if you’re becoming the person who understands AI the most in your field, this thing is nothing short of a superpower.