Bill Gurley says that right now, the worst thing you can do for your career is play it safe

For nearly three decades, Bill Gurley has been among 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 stepped back 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 thinks he can actually help solve.

The book is Runnin’ Down a Dream — a nod to Tom Petty and also an argument that following your passion isn’t just romanticized career advice but a true competitive strategy, one that becomes only more urgent as AI rapidly reshapes the workforce. The foundation, which he’s calling the Running Down a Dream Foundation, will award 100 grants of $5,000 a year to people who need a financial cushion to make a leap they’ve been afraid to take.

We caught up with Gurley to talk about all of it — including what he makes of the somewhat surreal reality that several of his former peers in tech now hold enormous sway in Washington, why he thinks the 996 grind culture many young founders have adopted 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 conversation with Gurley drops Tuesday on TC’s StrictlyVC Download 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 a market evolving. I wrote them down. A couple years later I got invited to speak at the University of Texas, dusted off the notes, built a presentation. They posted it on YouTube, and James Clear — who wrote Atomic Habits — noticed and posted about it. That’s what got me thinking about a book. And when I went through my own process of moving away from venture and thinking about what I wanted to do next, it became obvious 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 careers over. That shocked you. Why?

When we first ran 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 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 regrets of inaction — the thing that weighs on people most as they get older is the thing they didn’t try, the stone left unturned. That holds across multiple geographies and cultures. And I think a lot of well-intentioned parents feel more responsibility to create economic stability for their kids than to encourage them to truly explore their passion. Especially with AI out there, that may not have been the right call.

Exploring your passion sounds like easier advice for people who have financial runway. What do you say to someone working paycheck to paycheck?

A few things. First, the book profiles people who started on the very bottom rung and climbed to the top — [celebrity hairstylist and entrepreneur] Jen Atkins moved to LA with $200 in her pocket. There’s nothing in the book that says you need to start anywhere other than right at the beginning. Second, if you’re living paycheck to paycheck, I wouldn’t encourage you to quit. I’d encourage you to use your free time to build a little document on your phone about what your thing might be. Learn. Prepare to jump before you jump. And third — this is why I’m 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 in exactly that position, who can convince us in an application that they’ve thought long and hard about where they want to go but 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 speech on regulatory capture a few years back — it was at the All-In Summit — and at the time I said I had a fear that the AI companies would try to use regulation to protect themselves. I think that’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, arguing social media has been really bad for children, with academic research to back it up. People would say we should have gotten in front of social media and need to do it with AI. The problem is that the people begging 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 entangled in state-by-state regulation and Chinese models are running free, we’re going to paint ourselves in 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 state know how to write good AI regulation that will actually work?

It’s a little surreal that several prominent figures from your world now hold enormous influence in Washington. What do you make of that?

It’s very ironic. If you go back and watch that regulatory capture talk, who would have thought a few years later David Sacks would actually be [special advisor for AI and crypto in the White House]?

Back in 2018, Mike Moritz of Sequoia wrote in the FT that Americans would lose to China if they didn’t start working harder. It was controversial at the time, but a lot of young founders here seem to have since embraced a punishing work culture — the 996 ethos. What are your thoughts about what’s happening?

I kind of love it, honestly. I think Silicon Valley got really lazy during COVID — people weren’t coming into the office, the culture got soft in a way 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’re going to lose not because they’re smarter but because they have a better work ethic. But here’s the thing: if you study successful people across a lot of fields, we think it’s wonderful when an athlete practices 12 hours a day or when an artist works obsessively on their craft. Nobody says Jordan didn’t have work-life balance. We just don’t extend the same logic to building a company. If those founders love what they’re doing that much, and they feel like this is the moment to go hard, that’s actually precisely the point of the book: find the thing that makes you feel that way.

You talk about mentorship in the book. What makes a great mentor relationship and how do people find one?

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 that’s ridiculously too high and unachievable, and it doesn’t work. For all those people that are really out of reach right now, I call them aspirational mentors — create a persona of them, just like I was talking about with the dream job folder. 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 talking to them directly, especially in the modern age. And then for your real mentors, go two levels down from where you thought you were going to aim. Discover somebody — tools like LinkedIn make this so easy — and be the first person to ever call them and ask them to be a mentor, because they’ll be flattered. They’ll be flattered that you knew who they were. Imagine anyone getting their first call to be a mentor. It’s a great feeling. You’re going to have way more success with that interaction than shooting too high.

I’ll tell you a funny story: I started getting so many calls from people who wanted to break into venture that I wrote a three-page PDF called “So You Want to Be a VC,” and hidden in the third page was basically — go do X, go do Y, go do Z, come back and tell me how that went. The number of people that actually ended up talking to me after getting that document was a fraction of the number I sent it to. It’s funny how much it thinned when you gave them a little homework to do.

You started working on this book before the impacts of AI became clearer. Does that at all change how people should think about their careers?

If you’re following the traditional path — going through the career center at your university, signing up on a list, waiting for a recruiter to sit through 30 people in 20-minute slots — you look like a cog. You look mass-produced. For that group, AI looks frightening, and maybe it should. But if you are blazing your own trail, using the techniques in the book, becoming what I call a candidate of one — someone whose path looks completely unique because you’ve built it intentionally — then every tool in this book is amplified by AI. Learning has never been easier than right now, in the entire history of the world. If you’re running toward it, if you’re becoming the most AI-aware person in your field, this thing is nothing but a superpower.