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

"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."

"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."

Bill Gurley spent nearly three decades as a Benchmark general partner, making early investments in Uber, Zillow, and Stitch Fix that shaped modern venture capital. After moving to Austin and stepping back from active investing, he shifted focus to a book, a foundation, and a policy institute targeting solvable problems. The book, Runnin' Down a Dream, frames following passion as a competitive strategy, especially as AI reshapes the workforce. The Running Down a Dream Foundation will provide 100 annual $5,000 grants to people making career leaps. Topics also include tech leaders' influence in Washington, 996 work culture, and AI's career implications.

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