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, having moved to Austin and retired from active investing, the native Texan is channeling that same pattern-recognition instinct into something different: a book, a foundation and a policy institute aimed at problems he believes he can actually move.
The book is Runnin’ Down a Dream — a nod to Tom Petty and also an argument that following your passion isn’t just romantic career advice, but a real competitive strategy, one that’s becoming more urgent as artificial intelligence rapidly reshapes the workforce. The foundation, which it 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 a leap they’ve been afraid to take.
We caught up with Gurley to talk about all of this — including what he makes of the somewhat surreal reality that several of his former tech peers now have enormous influence in Washington, because he believes the 996 grind culture Many new founders have adopted it is less alarming than it sounds, and what artificial intelligence really means for your career. The following has been edited for length and clarity. Our full conversation with Gurley is out Tuesday on TC Download StrictlyVC podcast.
Why write this book?
I went through a phase where I was reading a lot of biographies—people from very different fields, different time windows—and I started noticing patterns the way I would notice patterns in an evolving market. I wrote them. A few years later I was invited to speak at the University of Texas, dusted off the notes, put together a presentation. It was also posted on YouTube by James Clear — who wrote Individual habits — noticed and published about it. This made me think of a book. And when I went through my own process of stepping away from the venture 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 about 60% of people would do things differently if they could start their career over. That shocked you. Why?
When we first did it as a SurveyMonkey poll, we got seven out of ten. When we did it more rigorously with Wharton, we got six out of ten. One of the things that strikes me is that we have a phrase in the book — life is a use-it-or-lose-it proposition — and when you’re young, it’s just hard to have that frame of mind. 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 regrets of inaction—what weighs on people the most as they get older is what they didn’t try, the stone left unanswered. This is true in many geographies and cultures. And I think many well-intentioned parents feel a greater responsibility to create financial stability for their children than to encourage them to truly explore their passion. Especially with AI out there, that might not have been the right call.
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Exploring your passion sounds like easier advice for people on a budget. What do you say to someone who works from paycheck to paycheck?
A few things. First, the book profiles the people who started at the bottom and rose to the top — [celebrity hairstylist and entrepreneur] Jen Atkins moved to Los Angeles with $200 in her pocket. There is nothing in the book that says you have to start anywhere but the beginning. Second, if you’re living paycheck to paycheck, I wouldn’t encourage you to quit. I would recommend using your free time to create a little document on your phone about what your thing might be. Learn. Prepare to jump before you jump. And thirdly — this is why I am launching 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 who are exactly in that position, who can convince us in an application that they’ve thought long and hard about where they want to go, but they need a little help getting there.
You’ve been outspoken for years 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 at the time I said I was afraid that AI companies would try to use regulation to protect themselves. I think this is happening now. The other side is that there are reasonable questions: Jonathan Haidt’s book Anxious Generation has been on the bestseller list for almost two years, arguing that social media was very bad for children, with academic research backing it up. People would say we should have come before social media and we should have done it with artificial intelligence. The problem is that the people calling for regulation the most in AI are the actual companies themselves, and that makes me skeptical. There’s also the global dimension—if US AI gets bogged down in state-by-state regulation and Chinese models run free, we’ll be painting ourselves red tape. I always ask people: what are your favorite five regulations of all time and how were they successful? Do you have any confidence that people at the state level in a random situation know how to write good AI regulation that will actually work?
It’s a little 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 that deregulation speech, who would have thought that a few years later David Sacks would actually be [special advisor for AI and crypto in the White House]?
Back in 2018, Sequoia’s Mike Moritz wrote in the FT that the Americans would lose out to China if they didn’t start working harder. It was controversial at the time, but many new founders here seem to have since embraced a punishing work culture – the ethos of 996. What are your thoughts on what’s going on?
I love it, honestly. I think Silicon Valley got really lazy during COVID – people weren’t coming to the office, the culture got soft in a way that I hadn’t seen in all my years there. And I’ve been to China six times. I know what Michael Moritz was describing when he said we will lose not because they are smarter but because they have a better work ethic. But here’s the thing: if you study successful people in many fields, we think it’s great when an athlete works out 12 hours a day or when an artist works obsessively on their art. 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 like this is the time to go hard, that’s exactly what the book is about: find what makes you feel that way.
You talk about guidance in the book. 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’s permeating the self-help world: “go get a mentor,” and everyone runs out and calls someone who’s ridiculously lofty and unattainable, and it doesn’t work. For all those people who are really unreachable right now, I call them aspirational mentors — create a persona of them, just like I was talking about with the dream job portfolio. Get excerpts from 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 talking to them directly, especially in the modern age. And then for your actual mentors, go down two levels from where 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’ll be flattered you knew who they were. Imagine someone receiving their first call to become a mentor. It’s a wonderful feeling. You will have much more success with this interaction than shooting too high.
I’ll tell you a funny story: I started getting so many calls from people wanting to get into the venture that I wrote a three-page PDF called “So You Want to Be a VC,” and tucked away on the third page was basically — go do X, go do Y, go do Z, come back and tell me how it went. The number of people who actually ended up talking to me after receiving this 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 to do.
You started working on this book before the implications of artificial intelligence became clearer. Does this change the way people should think about their careers at all?
If you follow the traditional path – stopping by the career center at your university, signing up for a list, waiting for a recruiter to sit among 30 people in 20 minutes – you look like a cog. You look mass produced. To this group, artificial intelligence seems scary, and maybe it should. But if you forge your own path, using the techniques in the book, become what I call a candidate – someone whose path seems completely unique because you’ve made it on purpose – then every tool in this book is powered by artificial intelligence. Learning has never been easier than right now, in the entire history of the world. If you run towards it, if you become the most AI-aware person in your field, this thing is nothing short of a superpower.
