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

Bill Gurley has been one of the most influential voices in Silicon Valley for nearly three decades—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 that he’s moved to Austin and stepped back from active investing, the native Texan is channeling that same pattern-recognition instinct into something else: a book, a foundation and a policy institute focused on problems he thinks he can actually solve.

The book is Chasing a dream – a nod to Tom Petty and also an argument that following your passion is not just romanticized career advice, but an actual competitive strategy, one that will only become more urgent as AI rapidly reshapes the workforce. The foundation, which he calls the Running Down a Dream Foundation, will award 100 grants of $5,000 per year to people who need a financial cushion to make a leap they never dared to take.

We caught up with Gurley to talk about it – including what he thinks about the somewhat surreal reality that some of his former colleagues in the tech sector now have enormous influence in Washington, why he thinks the 996 grinding culture have hired many young founders 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 will land on TC’s on Tuesday Download Strictly VC podcast.

Why write this book?

I went through a phase where I read 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 developing market. I wrote them down. A few years later I was invited to speak at the University of Texas, dusted off the notes and built a presentation. They posted it on YouTube, and James Clear – who wrote Atomic habits – noticed and posted about it. That got me thinking about a book. And as I went through my own process of stepping away from ventures 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 something that could have a bigger mission.

Your research at Wharton found that about 60% of people would do things differently if they could start their career over. That shocked you. Why?

When we first ran it as a SurveyMonkey survey, we scored 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 matter of ‘use it or lose it’ – and when you’re young it’s just hard to have that framework. It’s hard to fast forward all your time and realize how precious it is. Daniel Pink has done a lot of work on what he calls the regret of inaction. What weighs most heavily on people as they grow older is what they haven’t tried and turned the stone over. This applies to multiple geographies and cultures. And I think many well-intentioned parents feel more responsibility to create economic stability for their children than to encourage them to truly explore their passion. Especially with AI out there, that might not have been the right choice.

Exploring your passion sounds like simpler advice for those with a financial runway. What do you say to someone who works paycheck to paycheck?

A few things. First, the book profiles people who started on the 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 have to start anywhere other than the beginning. Second, if you’re living paycheck to paycheck, I wouldn’t encourage you to quit. I recommend using your free time to create a little document on your phone about what your thing could be. Learn. Prepare to jump before you jump. And thirdly, 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 worth $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 regulations to entrench themselves.

A few years ago I gave a speech on regulatory capture – it was at the All-In Summit – and at the time I said I was concerned 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 that social media is very bad for children, with academic research to back it up. People would say we should have gotten to social media and done it with AI. The problem is that the people most clamoring for AI regulation are the companies themselves, and that makes me skeptical. There’s also the global dimension: if American AI gets mired in state-by-state regulation and Chinese models run wild, we’ll bury ourselves in red tape. I always ask people, what are your favorite five ordinances of all time, and how were they successful? Do you have any confidence that people at the state level in any state will know how to write good AI regulations that will actually work?

It’s a bit surreal that several prominent figures from your world now have enormous influence in Washington. What do you think about that?

It’s very ironic. If you look back at that conversation about regulatory capture, who would have thought a few years later, it would actually be David Sacks [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 work harder. It was controversial at the time, but many young founders here seem to have since embraced a punishing work culture: the 996 ethos. What are your thoughts on what is happening?

I like it, to be honest. I think Silicon Valley became very lazy during COVID – people weren’t coming to the office, the culture became 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 described when he said we’re going to lose not because they’re smarter, but because they have a better work ethic. But the thing is, if you study successful people in many fields, we love it when an athlete trains twelve hours a day or an artist works obsessively on his or her craft. No one is saying Jordan didn’t have a work-life balance. We just don’t apply the same logic to building a business. If those founders love what they do so much, and they feel like this is the time to go hard, then that’s exactly the point of the book: find the thing that makes you feel that way.

In the book you talk about mentorship. What makes a good mentoring relationship and how do people find one?

The most important thing is to get out of your head this ideal that goes around in the self-help world: “get a mentor,” and everyone runs out and calls up someone who is ridiculously overpriced and unattainable, and it doesn’t work. For all those people who are really out of reach right now, I call them aspirational mentors – create a persona of them, just like I talked about 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 modern times. And then for your real mentors, go two levels below where you thought you were aiming. Discover someone – tools like LinkedIn make this so easy – and be the first person to ever call them and ask them to become a mentor, because they will be flattered. They will be flattered that you knew who they were. Imagine someone getting the call to become a mentor for the first time. It’s a great feeling. You’ll have much more success with that interaction than with shooting too high.

I’ll tell you a funny story: I got so many calls from people wanting to start a venture that I wrote a three-page PDF called “So You Want to Be a VC,” and basically hidden on the third page was: go do X, go do Y, go do Z, come back and tell me how that went. The number of people who actually spoke to me after I received that document was a fraction of the number I sent it to. It’s funny how much it thinned out when you gave them some homework.

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

If you follow the traditional path—going through your college career center, signing up for a list, waiting for a recruiter to go through thirty people in twenty minutes—you’ll look like a cog. You look mass-produced. To that group, AI looks scary, and maybe it should. But if you forge your own path, use the techniques in the book, and become what I call a Candidate of Ones—someone whose path seems completely unique because you created it on purpose—then every tool in this book is enhanced by AI. Learning has never been easier than it is now, in the entire history of the world. If you’re running towards it, if you’re becoming the most AI-aware person in your field, this thing is nothing short of a superpower.