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

For nearly three decades, Bill Gurley has been one of the most influential voices in Silicon Valley — a senior contributor to Benchmark whose early bets on companies like Uber, Zillow, and Stitch Fix have helped define what modern entrepreneurship looks like. Now, having moved to Austin and taken a step back from investing, the Texan native is channeling that same process-awareness into something different: a book, foundation, and law firm focused on problems he thinks he can help solve.

The book is “Runnin’ Down a Dream” – a nod to Tom Petty and also the argument that following your dream is not just a romantic career strategy but a true competitive strategy, one that will only get faster as AI quickly adapts to the workforce. The foundation, which he is calling the Running Down a Dream Foundation, will award 100 grants of $5,000 a year to people who need a financial cushion to take the leap they were afraid to take.

We caught up with Gurley to talk about it all — including his take on the reality that his former tech peers have become so powerful in Washington, why he thinks the 996 grind culture adopted by many young people is scarier than it sounds, and what AI means for your career. The following has been edited for length and clarity. Our full interview with Gurley drops Tuesday on TC’s StrictlyVC Download podcast.

Why write this book?

I went through a phase where I was reading a lot of life – people from different places, different windows – and I started to see patterns the way I would see patterns in a changing market. I wrote it down. A few years later I was invited to speak at the University of Texas, took notes, and prepared a presentation. They posted it on YouTube, and James Clear – who wrote “Atomic Habits” – noticed and posted about it. That’s what got me thinking about the book. And when I went through my process of stepping away from acting 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 could have a big role.

Your research with Wharton found that about 60% of people would do things differently if they could start their own careers. That shocked you. How come?

When we first did the SurveyMonkey poll we got 7 out of 10. When we did it hard with Wharton, we got six out of 10. One of the things that touches me is that we have a line in the book – life is used when it is lost – and when you are young, it is difficult to have that frame. It’s hard to fast-forward through your entire life and realize how important it is. Daniel Pink has done a lot of work that he says he regrets not doing – the thing that weighs people down the most when they get old is the one they didn’t try, the stone left unturned. It applies to many geographies and cultures. And I think many well-intentioned parents feel more of a responsibility to create financial stability for their children than to encourage them to really explore their passion. Especially with AI out there, that might not be the right call.

Investigating your passion sounds like an easy idea for people with a tight budget. What do you say to a wage earner to pay?

Few things. First, the book shows people who started at the bottom and rose to the top – [celebrity hairstylist and entrepreneur] Jen Atkins moved to LA with $200 in her pocket. Nothing in the book says you have to start anywhere but the very beginning. Second, if you are living paycheck to paycheck, I would not recommend that you quit. I encourage you to use your free time to build a small document on your phone about your potential. Learn it. Prepare to jump before you jump. And third – this is why I’m starting a foundation. The last page of the book talks about it: We will give 100 grants a year of $5,000 to people in that particular area, who can convince us in the application that they have thought long and hard about where they want to go but need a little help to get there.

You’ve been talking for years about regulatory takeovers – the idea that big companies use the law to strengthen themselves.

I gave a speech about the seizure of control a few years back – it was at the All-In Summit – and at the time I said that I was afraid that AI companies would try to use the law to protect themselves. I think it’s happening now. The flip side is that there are legitimate questions: Jonathan Haidt’s book “Anxious Generation” has been a bestseller for nearly two years, arguing social media is actually bad for kids, with academic research to back it up. People would say we should have gotten there before social media and we should have done it with AI. The problem is that the people asking for the most control in AI are the very companies themselves, and that makes me skeptical. There is also a global dimension – if US AI is introduced into country-by-country legislation and Chinese brands are running free, we will paint ourselves red tape. I always ask people: What are your five favorite rules of all time, and how successful have they been? Do you have confidence that the people at the government level in an emergency know how to write good AI policy that will actually work?

It’s a little surreal that several famous people from your country now have a lot of power in Washington. What do you do with it?

It is very surprising. If you go back and watch the executive take interview, who would have thought a few years later David Sacks would be [special advisor for AI and crypto in the White House]?

Back in 2018, Sequoia’s Mike Moritz wrote in the FT that Americans would lose China if they didn’t start working harder. It was controversial at the time, but many young people who started here seem to have embraced the culture of disciplined work – the 996 ethos. What do you think of what is happening?

I love it, of course. I think Silicon Valley was really lazy during the COVID – people weren’t coming into the office, it’s a softer culture in a way that I haven’t seen in all my years there. And I went to China six times. I know what Michael Moritz was explaining when he said that we will lose not because they are smart but because they have a better work ethic. But here’s the thing: If you study successful people in many areas, we think it’s amazing if an athlete trains 12 hours a day or if an artist works hard on their craft. No one is saying that Jordan didn’t have a work-life balance. We don’t just add a single idea to build a company. If those who started love what they are doing so much, and feel like it’s time to go hard, that’s exactly the point of the book: Find something that makes you feel that way.

You talk about mentorship in the book. What makes a great teacher relationship and how do people find him?

The number one thing is to get out of your head this idea that is passed around in the self-help world: “go get a counselor,” and everyone runs out and cold calls someone who is too funny and impossible, and it doesn’t work. For all those people who are unreachable now, I call them aspirants – create their person, as I was talking about the dream job folder. Get excerpts from all the books they’ve written, podcasts they’ve done, interviews they’ve done, and learn. You can learn a lot from people without talking to them directly, especially in this day and age. And for your real coaches, go two steps down from where you thought you’d aim for them. Get to know someone – tools like LinkedIn make this easy – and be the first person to call them and ask them to be a mentor, because they will be flattered. They will be glad you knew who they are. Imagine anyone getting their first calling to be a coach. Great feeling. You will have more success with that interaction than shooting too much.

I’ll tell you a funny story: I started getting calls from people who wanted to break in so I wrote a three-page PDF called “So You Want to Be a VC,” and hidden on 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 ended up talking to me after I got that document was a fraction of the number I sent. It’s funny how much weight they lost when you gave them a little homework.

You started working on this book before the nature of AI was clear. Does this change how people think about their jobs?

If you follow the traditional way – going through the work center at your university, signing on the list, waiting for the guard to sit with 30 people in 20 minutes – you look like a cog. You look well-made. For that group, AI looks scary, and maybe it should. But if you’re blazing your own trail, using the skills in the book, being what I call someone’s agent – someone whose path looks unique because you built it on purpose – then every tool in this book is augmented by AI. Learning has never been easier than it is now, in the entire history of the world. If you run towards it, if you become the most knowledgeable AI in your field, this thing is nothing but a great power.