For nearly three decades, Bill Gurley has been among of 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 what modern venture capital looks like. Now, having moved to Austin and stepped back from active investing, the native Texan is channeling that same pattern-recognition instinct into something different: a book, a foundation, and a policy institute aimed at problems he thinks he can actually move.
The book is Runnin’ Down a Dream — a nod to Tom Petty and also an argument that following your passion isn’t just romanticized career advice but an actual competitive strategy, one that becomes only more urgent as AI rapidly reshapes the workforce. The foundation, which he’s calling the Running Down a Dream Foundation, will award 100 grants of $5,000 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 all of it — including what he makes of the somewhat surreal reality that several of his former peers in tech now hold enormous sway in Washington, why he thinks the 996 grind culture many young founders have adopted 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 drops Tuesday on TC’s StrictlyVC Download podcast.
Why write this book?
I went through a phase where I was reading 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 market evolving. I wrote them down. A couple years later I got invited to speak at the University of Texas, dusted off the notes, built 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 a book. And when I went through my own process of moving away from venture and thinking about what I wanted to do next, it became obvious I didn’t want to write about VC or Uber or any of that. I wanted to do something that could have a bigger mission.
Your research with Wharton found that roughly 60% of people would do things differently if they could start their careers over. That shocked you. Why?
When we first ran it as a SurveyMonkey poll we got 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 use it or lose it proposition — and when you’re young, it’s just hard to have that framing. It’s hard to fast-forward through all of your time and recognize how precious it is. Daniel Pink has done a lot of work on what he calls regrets of inaction — the thing that weighs on people most as they get older is the thing they didn’t try, the stone left unturned. That holds across multiple geographies and cultures. And I think a lot of well-intentioned parents feel more responsibility to create economic stability for their kids than to encourage them to truly explore their passion. Especially with AI out there, that may not have been the right call.
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