For nearly 30 years, Bill Gurley has been one of Silicon Valley's most influential voices, a general partner at Benchmark, an early investor in companies like Uber, Zillow, and Stitch Fix, and helped define what modern venture capital looks like. Now, having moved to Austin and taken a break from active investing, the Texas native is channeling those same pattern-recognition instincts into something else: books, foundations, and policy institutes focused on issues he thinks can actually move.
The book, Runnin' Down a Dream, is a tribute to Tom Petty and an argument that following your passion is not just romantic career advice, but an actual competitive strategy, one that becomes increasingly urgent as AI rapidly reshapes the workforce. The foundation, which he calls the Running Down a Dream Foundation, will award 100 annual $5,000 grants to people who need the financial cushion to take the leap they've been afraid to make.
We caught up with Gurley to tell us all about it. That includes how he views the somewhat surreal reality that some of his former colleagues in the tech industry now have significant influence in Washington, why he thinks the 996 grind culture many young founders are embracing isn't as alarming as it seems, and what AI actually means for your career. The following has been edited for length and clarity. The full conversation with Gurley will appear on TC's StrictlyVC Download podcast on Tuesday.
Why write this book?
I went through a phase where I was reading a lot of biographies of people in very different fields and different time periods, and I started noticing patterns, the same way you notice patterns in an evolving market. I wrote them down. A few years later, I was invited to speak at the University of Texas, where I dusted off my notes and created a presentation. They posted it on YouTube, and James Clear, who wrote Atomic Habits, noticed it and posted it. That got me thinking about the book. And as I went through my own 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 anything like that. I wanted to do a job with a bigger mission.
According to a study with Wharton, approximately 60% of people believe they would do things differently if they could start their career over again. It shocked you. why?
The first time I ran it as a SurveyMonkey survey, I got a 7 out of 10. A more rigorous test using Wharton gave it a 6 out of 10. One of the things that stands out to me is the phrase in the book, “Life is about using it or losing it,'' and when you're young, it's hard to grasp that framework. It's hard to fast forward through all the time and realize how precious it is. Daniel Pink has done a lot of research on what he calls “regret of inaction.” The things that weigh most heavily on people as they grow older are the things they didn't try, the stones left unchallenged. That's true across multiple regions and cultures. And I think many well-meaning parents feel more responsible for creating financial security for their children than for encouraging them to truly pursue their passions. That may not have been the right decision, especially in this day and age of AI.
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Exploring your passion seems like easy advice for those who can afford it. What would you say to someone who works for a paycheck?
A few things. First, this book introduces 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. Nothing in this book says you have to start anywhere other than the beginning. Second, if you are living within your paycheck, I don't recommend quitting. I recommend using your free time to create a small document on your phone about what you want to do. learn. Prepare to jump before you jump. Thirdly, this is why I am starting the foundation. The last page of this book talks about it. We're going to award 100 $5,000 grants a year to people in just that position – people who have thought long and hard about where they want to go, but whose applications can convince us that they need a little help getting there.
For years, you've been outspoken about regulatory co-optation, the idea that large companies use regulation to establish themselves.
I gave a speech at the All-In Summit a few years ago about regulatory capture, and I said that I was concerned that AI companies would try to use regulation to protect themselves. I think that's what's happening now. On the other hand, there are natural doubts. Jonathan Haidt's book, An Anxious Generation, has been on bestseller lists for almost two years, making the case, backed by academic research, that social media is really bad for children. People will say we should introduce social media and we should do it with AI. The problem is that the people most looking for regulation when it comes to AI are the actual companies themselves, and I'm skeptical of that. There is also a global aspect. If U.S. AI gets wrapped up in state-by-state regulation and Chinese models are allowed to operate freely, we will be creating red tape ourselves. I always ask people: What are your five favorite regulations of all time, and how were they successful? How confident are you that people at the state level in random states know how to write good AI regulations that actually work?
It's a little surreal that some of the most prominent figures in your world now have tremendous influence in Washington. What do you think about it?
That's very ironic. If we went back and looked at stories about regulatory capture, who would have imagined that a few years later that would actually be the case with David Sachs? [special advisor for AI and crypto in the White House]?
Back in 2018, Sequoia's Mike Moritz wrote in the FT that if Americans didn't try harder, they would lose to China. This was controversial at the time, but since then many of the young founders here seem to have embraced the demanding work culture of the 996 spirit. What do you think about what is happening?
To be honest, I quite like it. I think Silicon Valley has been really lazy during the coronavirus pandemic. People stopped coming into the office, and the culture softened in a way I hadn't seen in all my years. And I went to China six times. I get it when Michael Moritz said we're going to lose not because they're smarter, but because they have a better work ethic. But here's the problem. When I study successful people in different fields, I think it's great that athletes practice 12 hours a day or that artists work relentlessly on their craft. No one is saying Jordan didn't have work-life balance. We do not extend the same logic to company formation. If these founders love what they do so much that they feel it's time to go all in, then that's exactly the point of this book. Find something that makes you feel that way.
You talk about mentorship in your book. What is a good mentoring relationship and how do people find one?
The most important thing is to get out of your head this ideal that is so prevalent in the world of self-help. “Let’s go find a mentor,” everyone runs out and coldly calls someone who is ridiculously overpriced and unattainable, but it doesn’t work. I call them aspirational mentors for people who are really out of reach at the moment. Create a persona for them, just like we talked about your dream job folder. Get clips of all the books they've written, podcasts they've done, interviews they've done, and research them. Especially in today's world, you can learn a lot from people without having to talk to them directly. And for a true mentor, go two levels below where you thought you were going. Tools like LinkedIn make this very easy. Find someone and be the first person to call them and ask them to be your mentor. Because it will make you happy. They will be happy if you know who they are. Imagine the person receiving your first call as a mentor. I feel great. That interaction will be much more successful than shooting too high.
Let's talk about something interesting. I started getting so many calls from people who wanted to get into venture business that I wrote a three-page PDF called “So You Want to Be a VC.” Hidden on the third page was basically, “Do X, do Y, do Z, come back and tell me how it went.” The number of people who actually ended up talking to me after receiving that document was a fraction of the number I sent it to. It's funny how thin it gets when you give it a little homework.
This book was written before the impact of AI was clear. Does it change the way people should think about their careers at all?
If you follow the traditional method of going through your university's career center, signing up for a list, and waiting for a recruiter to interview 30 people in a 20-minute window, you're a cog in the wheel. It looks like a mass-produced model. To that group, AI looks scary, and maybe it should. But if you use the techniques in this book to carve your own path and become what I call that candidate, someone whose path looks completely unique because they intentionally built it, all the tools in this book are powered by AI. Never in the history of the world has learning been easier than it is now. If you're running towards it, if you're trying to become the most AI-aware person in your field, this is nothing short of a superpower.