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

For nearly three decades, Bill Gurley has been among 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 the shape of modern venture capital. Now, after moving to Austin and stepping back from active investing, the Texas native is channeling that same pattern-recognition instinct into something different: a book, a foundation, and a policy institute aimed at solving problems he believes he can actually move.

The book is Running down the dream — a nod to Tom Petty and also an argument that following your passion isn’t just romantic career advice, it’s an actual competitive strategy, one that’s becoming more urgent as artificial intelligence rapidly reshapes the workforce. The foundation, called the Running Dream Foundation, will award 100 $5,000 grants 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 it all — including what he makes of the somewhat surreal reality that many of his former tech peers now wield outsized influence in Washington, why he thinks the 996-grinding culture adopted by many young founders is less troubling 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 will start on Tuesday on TC’s StrictlyVC Download podcast.

Why am I writing this book?

I went through a phase where I was reading a lot of biographies – from people from very different fields, and different windows of time – and I started noticing patterns in the same way I notice patterns developing in the market. I wrote them. Two years later, I received an invitation to speak at the University of Texas, dusted off my notes, and prepared a presentation. They posted it on YouTube, and James Clear wrote it Atomic habits -I noticed and posted about it. This is what made me think of a book. As I went through the 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 venture capital or Uber or any of that. I wanted to do something that could have a bigger mission.

Your research with Wharton finds that nearly 60% of people would do things differently if they could start their careers over. I shocked you. Why?

When we first ran it as a SurveyMonkey poll, we got a seven out of ten. When we did it more precisely with Wharton, we got a six out of ten. One of the things that struck 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 have that framework. It’s hard to fast forward through all your time and realize how valuable it is. Daniel Pink has done a lot of work on what he calls regret of inaction—the thing that weighs on people most as they get older is the thing they didn’t try to do, didn’t turn over the stone. This applies to multiple geographies and cultures. I think a lot of well-meaning parents feel more responsible for providing economic stability for their children rather than encouraging them to truly explore their passions. Especially with AI, this probably wasn’t the right decision.

Exploring your passion seems like an easier tip for people with a financial runway. What would you say to someone who works paycheck to paycheck?

Some things. First, the book profiles people who started at the bottom and rose to the top — [celebrity hairstylist and entrepreneur] Jane Atkins moved to Los Angeles with $200 in her pocket. There’s nothing in the book that says you have to start anywhere other than the beginning. Second, if you’re living paycheck to paycheck, I wouldn’t encourage you to quit. I would encourage you to use your free time to create a little document on your phone about what your favorite thing is. He learns. Prepare to jump before you jump. And third – that’s why I’m launching the foundation. The last page of the book talks about it: We’ll give away 100 scholarships a year worth $5,000 to people who are in exactly this position, and who can convince us on their application that they’ve thought long and hard about where they want to go but need a little help getting there.

I’ve been vocal for years about regulatory capture — the idea that big companies use regulation to entrench themselves.

I gave a speech about regulatory capture a few years ago — it was at the All-In Summit — and at the time I said I had a fear that AI companies would try to use regulation to protect themselves. I think this is happening now. The flip side is that there are legitimate questions: Jonathan Haidt’s book A worried generation It was on the bestseller list for about two years, arguing that social media was really bad for kids, with academic research to back it up. People might say that we should have stood up to social media, that we need to do this with artificial intelligence. The problem is that the people asking for regulation the most in AI are the actual companies themselves, and that makes me skeptical. There’s also the global dimension — if American AI gets bogged down in regulation on a country-by-country level, and Chinese models operate freely, we’ll paint ourselves in the red. I always ask people: What are your five favorite rules of all time, and how did they work? Do you have any confidence that people at the state level in a random state know how to write good AI regulations that will actually work?

It’s a bit surreal that so many prominent figures from your world now wield enormous influence in Washington. What do you make of it?

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

In 2018, Sequoia’s Mike Moritz wrote in the Financial Times that Americans would lose to China if they didn’t start working harder. It was controversial at the time, but it seems a lot of young founders here have since embraced the punitive work culture – the ethos of 996. What are your thoughts on what’s happening?

I kind of like it, honestly. I think Silicon Valley has become very lazy during the coronavirus crisis – people don’t come to the office anymore, and the culture has become weak in a way that I haven’t seen in all the years I’ve lived there. I have 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 practices 12 hours a day or an artist works obsessively on his craft. No one is saying that Jordan didn’t have a work-life balance. We don’t apply the same logic to building a company. If these founders love what they do so much, and feel like this is the right moment to work hard, then that’s actually exactly 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 it?

The first thing is to get out of your head that example that gets passed around in the self-help world: “Go get a mentor,” and everyone runs out and calls someone ridiculously high and unattainable, and it doesn’t work. For all those people who aren’t really accessible right now, I call them aspirational mentors – create a persona for them, just like I was talking about the Dream Job folder. Get clips from all the books they’ve written, podcasts they’ve done, and interviews they’ve done, and study them. You can learn a lot from people without talking to them directly, especially in the modern age. Then, for your real mentors, go two levels down from where you thought you were going to target. Discover someone – tools like LinkedIn make this very easy – and be the first person they ever contact and ask them to be a mentor, because they will be flattered. They will be glad you knew who they are. Imagine anyone receiving their first call to be a mentor. It feels great. You will have much more success with this interaction than shooting at very high altitudes.

I’ll tell you a funny story: I started getting so many calls from people who wanted to break into the venture that I wrote a three-page PDF titled “So You Want to Be a VC,” and hidden 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 ended up actually talking to me after getting that document was a fraction of the number I sent it to. It’s funny how weak it gets when you give them a little homework to do.

I started working on this book before the effects of AI became clearer. Does this change at all the way people should think about their careers?

If you’re following the traditional route—by going to your university’s career center, signing up for a list, and waiting for a recruiter to seat 30 people in 20-minute intervals—you’re looking like a cog. You seem mass produced. To this group, AI seems scary, and perhaps it should be. But if you forge your own path, using the techniques in the book, and become what I call a single candidate—someone whose path seems completely unique because you intentionally built it—every tool in this book will be amplified by AI. Learning has never been easier than it is now, in the entire history of the world. If you move towards that, if you become the most AI-aware person in your field, then this thing is nothing short of a superpower.