For nearly three decades, Bill Gurley has been one of the most influential voices in Silicon Valley — a general partner of Benchmark, whose early bets on companies like Uber, Zillow and Stitch Fix helped define what modern venture capital looks like. Now, after relocating to Austin and stepping back from active investing, the native Texan is channeling that same pattern-recognition instinct in a slightly different way: 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 romantic career advice, but a true competitive strategy, one that becomes even more essential as AI increasingly reshapes the workforce. The foundation, which he is calling the Running Down a Dream Foundation, will award 100 grants of $5,000 per year to people who need financial assistance to take a leap they may be afraid to take.
We caught up with Gurley to talk about all this — in which he explains the somewhat surreal reality that many of his former peers in tech now hold enormous influence in Washington, why he thinks the 996 grind culture that many young founders have adopted is less dangerous than it seems, and what AI can really mean for your career. The following has been edited for length and clarity. Our full conversation with Gurley will be on TC’s StrictlyVC Download podcast Tuesday.
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 to see patterns the same way I see patterns developing in a market. I wrote them down. A few years later, I was invited to speak at the University of Texas, dusted off my notes, and prepared a presentation. He posted it on YouTube, and James Clear – who wrote “Atomic Habits” – saw it and posted about it. This is what made me think of a book. And as I went through my process of stepping away from 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 had a bigger mission.
Your research with Wharton found that nearly 60% of people would do things differently if they could start their career over again. This shocked you. Why?
When we first ran it as a SurveyMonkey poll we got a seven out of 10. When we did it more rigorously with Wharton, we got a six out of 10. One thing 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 hard to get that framing. It’s hard to fast forward all of your time and recognize just how precious it is. Daniel Pink has done a lot of work on what he calls regrets of inaction – the thing that has the biggest impact on people as they age are the things they didn’t try to do, the things that remain undone. This applies to many geographic regions and cultures. And I think a lot of well-intentioned parents feel more of a responsibility to create economic stability for their kids than to actually encourage them to explore their passions. Especially with AI, this may not be the right decision.
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Discovering your passion seems like easy advice for those who have ample financial opportunities. What do you say to someone working from paycheck to paycheck?
Some things. First, this book profiles people who started at the bottom and climbed to the top – (celebrity hair stylist 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 the beginning. Second, if you’re living paycheck to paycheck, I wouldn’t encourage you to quit your job. I would encourage you to use your free time to create a little document on your phone of 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 away 100 grants of $5,000 a year to people who are in exactly the same situation, who can convince us in an application that they’ve thought for a long time about where they want to go but they just need a little help getting there.
You’ve been vocal for years about regulatory capture – the idea that big companies use regulation to strengthen themselves.
I gave a speech a few years ago on regulatory capture – it was at the All-In Summit – and at the time I said that I was afraid that AI companies would try to use regulation to protect themselves. I think this is what is 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 that social media is actually bad for kids, despite academic research supporting it. People will say that we should have come before social media and it needs to be done with AI. The problem is that the people pleading most for regulation in AI are the actual companies themselves, and that makes me skeptical. There’s also a global dimension to this – if American AI gets bogged down in state-by-state regulation and Chinese models run freely, we’re going to find ourselves in red tape. I always ask people: What are your favorite five rules of all time and how were they successful? Do you have any confidence that people in a random situation at the state level know how to write good AI regulation that will actually work?
It’s a bit surreal that many of the leading figures in your world now wield enormous influence in Washington. What do you make of that?
This is very ironic. If you go back and look at that regulatory capture talk, who would have thought that a few years later David Sachs would actually be (special advisor for AI and crypto in the White House)?
In 2018, Sequoia’s Mike Moritz wrote in the FT that Americans would lose to China if they didn’t start working harder. This was controversial at the time, but it seems many of the young founders here have since adopted a punishing work culture – the 996 ethos. What are your thoughts about what is happening?
To be honest, I kind of like it. I think Silicon Valley really got lazy during COVID — people weren’t coming into the office, the culture had softened in a way I hadn’t seen in all my years there. And I have been to China six times. I know what Michael Moritz was describing when he said that we lose not because they are smarter but because they have a better work ethic. But the thing is: If you study successful people in many fields, we think it’s amazing when an athlete practices 12 hours a day or when an artist works obsessively on their art. No one says Jordan didn’t have work-life balance. We do not extend the same logic to the creation of a company. If those founders love what they’re doing so much, and they feel like this is the moment to work hard, then that’s really the purpose 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 it?
The number one thing is to get out of your mind this idea that keeps floating around in the self-help world: “Go get a consultant,” and everyone runs off and calls someone who is ridiculously over-the-top and unattainable, and that doesn’t work. For all those people who are really out of reach right now, I call them aspiring gurus – create a persona of theirs, like I was talking about with the dream job folder. Get all the books they’ve written, podcasts they’ve done, clips of interviews they’ve done and study them. You can learn a lot even without talking to people directly, especially in the modern age. And then for your actual mentors, go two levels below where you thought you were going to aim. Find someone – tools like LinkedIn make it so easy – and be the first one to call them and ask them to be a mentor, because they’ll be delighted. They’ll be glad you knew who they were. Imagine getting the first call from someone to become a guru. This is a very good feeling. You’re going to have much more success from that conversation than from shooting too high.
Let me tell you a funny story: I started getting a lot of calls from people who wanted to get into venture, so I wrote a three-page PDF called “So You Want to Be a VC,” and basically hidden in the third page was – go do X, go do Y, go do Z, come back and tell me how it went. The number of people who actually talked to me after receiving that document was a fraction of the number of people I sent it to. It’s funny how much it goes down when you give them a little homework to do.
You started working on this book even before the effects of AI became clear. Has this changed the way people think about their careers at all?
If you’re following the traditional route – going through the career center at your university, signing up on a list, waiting for a recruiter to sit down with 30 people in a 20-minute slot – you look like a cog. You look mass produced. To that group, AI seems scary, and maybe it should. But if you’re paving your own path using the techniques in the book, becoming what I call a candidate – someone whose path looks completely unique because you’ve intentionally created it – then every tool in this book is enhanced by AI. Learning has never been easier than now in the entire history of the world. If you are racing towards it, if you are becoming the most AI-aware person in your field, then this thing is nothing but a superpower.
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