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

For nearly three decades, Bill Gurley has been one of Silicon Valley’s most iconic figures — a general partner at Benchmark whose early bets on companies like Uber, Zillow, and Stitch Fix helped define what modern capital looks like. Now, after moving to Austin and ceasing to invest quickly, the native Texan is turning that same idea—a sense of instinct—into something different: a book, a foundation, and a plan to deal with the problems he thinks he can move.

This book is Running Down Dreams – Tom Petty’s endorsement and the argument that following your passion is not just a romantic advice but a competitive strategy, which becomes more important as AI rapidly transforms the workforce. The foundation, which they call the Running Down a Dream Foundation, will award 100 grants of $5,000 a year to people who need money to take a leap of faith.

We caught up with Gurley to talk about it all — including what makes him the reality that several of his former friends in tech are now in power in Washington, and why he thinks so. 996 status Many young startups have adopted it is not as scary as it sounds, but also what AI means for your work. The following has been edited for length and clarity. Our full interview with Gurley drops Tuesday on TC’s Download StrictlyVC podcast.

Why did he write this book?

I went through a phase where I was reading a lot of articles – people from different sectors, different time windows – and I started to notice how I saw the market. I wrote it down. A few years later I was invited to speak at the University of Texas, I took notes, I made a presentation. He posted it on YouTube, and James Clear – who wrote it Atomic Tendencies – noticed and posted about it. That’s what made me think about the book. And when I went through my process of leaving the business and thinking about what I wanted to do, it became clear that I didn’t want to write about VC or Uber or any of that. I wanted to do something that would have a big purpose.

Your research with Wharton found that nearly 60% of people would do things differently if they had to start their career over again. That surprised you. Why?

When we first ran it as a SurveyMonkey survey we got seven out of ten. When we did our hardest with Wharton, we got six out of ten. One of the things that resonates with me is that we have a phrase in the book – life is use it or lose it – and when you’re young, it’s hard to live with it. It’s hard to spend all your time realizing how important it is. Daniel Pink has done a lot on what he calls the regret of inaction – something that weighs heavily on people when they grow up and something they haven’t tried, the stone is unturned. This applies to several regions and cultures. And I think many well-intentioned parents feel more responsible for providing financial stability for their children than encouraging them to pursue their passion. Especially with AI out there, it probably wasn’t the right call.

Watching your interests sounds like simple advice for people with money. What do you say to a working person to get paid?

A few things. First, the book tells about people who started from the bottom and rose to the top – (famous hair stylist and entrepreneur) Jen Atkins moved to LA with $200 in her pocket. Nothing in this book says you have to start anywhere but at the beginning. Second, if you’re living paycheck to paycheck, I wouldn’t recommend you quit. I encourage you to use your free time to make a small document on your phone about what you can be. Learn it. Prepare to jump before you jump. And third – this is why I’m starting a foundation. The last page of the book is about this: we will give 100 annual grants of $5,000 to people in the same place, who can prove to us in the application that they have thought deeply and seriously about where they want to go but they need a little help to get there.

You’ve been talking for years about legal capture – the idea that big companies use the law to establish themselves.

I gave a speech about the seizure of power a few years back – it was at the All-In Summit – and at the time I said that I was afraid that the AI ​​industry would try to use the law to protect itself. I think it’s happening now. The part is that there are legitimate questions: Jonathan Haidt’s book Anxious Age has been on the bestseller list for almost two years, arguing that social media has been really bad for children, and research studies behind it. People will say that we should have moved forward with social media and should have done it with AI. The problem is that the people asking for more control in AI are the companies themselves, and that makes me suspicious. There’s also a global dimension – if US AI gets caught up in state-by-state control and Chinese brands become free, we’ll be painting ourselves. I always ask people: what are your five favorite rules of all time, and how did they win? Are you confident that the people in random government know how to write good AI laws that will work?

It’s amazing how many famous people in the world have so much influence in Washington. What do you make of this?

It’s really amazing. If you go back and look at the recorded story of the director, who would have thought that a few years later it would be David Sacks (special adviser on AI and crypto at the White House)?

Back in 2018, Mike Moritz of Sequoia wrote in the FT that the Americans will lose to China if they don’t start. to work hard. It was controversial at the time, but many young startups now seem to have embraced the culture of disciplined work – the 996 ethos. What are your thoughts on what is happening?

I kind of like it, honestly. I think that Silicon Valley became very lazy during the COVID – people were not coming to the office, the culture softened in a way that I have not seen in all my years there. And I have been to China six times. I know what Michael Moritz was saying when he said that we will lose not because they are smart but because they have a good job. But here’s the thing: if you study successful people in many fields, we think it’s better if an athlete plays 12 hours a day or an artist works hard. No one is saying Jordan didn’t have a good career. We don’t develop the same mindset when building a company. If the founders love what they’re doing, and feel like it’s time to work hard, that’s the point of this book: find something that makes you feel that way.

You talk about counseling in the book. What makes a good relationship with a trainer and how do people find him?

The first thing is to get out of your head these thoughts that run through the world of help: ‘go get a consultant,’ and everyone runs and cold calls someone who is too high and impossible, and it doesn’t work. For all the people who can’t reach them right now, I call them willing mentors – make a person of them, as I speak with a dream folder. Find videos of all the books he’s written, podcasts he’s done, interviews he’s done, and study them. You can learn a lot from people you don’t talk to directly, especially in today’s world. And then for your real mentors, go two levels from where you think you want to be. Get to know someone – tools like LinkedIn make this easy – and be the first person to call them and ask them to be a coach, because they will be impressed. They will be impressed that you know who they were. Imagine anyone being called for the first time to be a mentor. It’s a great feeling. You’ll have a much better chance of success with that interaction than shooting too much.

I’ll tell you a funny story: I started getting so many calls from people who wanted to do business with me that I wrote a three-page PDF called “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 and tell me how it went. The number of people who ended up contacting me after I received the letter was a fraction of the number I sent it. It’s funny how much less it does when you give them homework to do.

You started working on this book before the complexities of AI became clear. Does this change the way people think about their jobs?

If you’re following the traditional methods — going through your university’s job fair, signing up on a list, waiting for a recruiter to sit among 30 people in 20-minute slots — you’re looking like a fluke. You look so made up. To that group, AI looks scary, and maybe it should. But if you’re blazing your own trail, using the techniques in this book, to be what I call a chosen person – someone whose path looks so different because you’ve made it on purpose – then every tool in this book is augmented by AI. Learning has never been easier in the history of the world. If you’re racing there, if you’re going to be the best AI in your field, this thing is nothing but a superpower.