
Trouncing career regret with famed VC Bill Gurley
From Riskgaming by Lux Capital
February 25, 2026 · 60 min
About this episode
Bill Gurley discusses his new book on avoiding career regret and finding passion in work.
An astonishing majority of Americans claim that they hate their job and wish they could do something else. Often though, what might drive our passions is an unknown. How do we find the right path in life and how do we know we are on our way?Joining the Riskgaming podcast this week is Bill Gurley, a legendary venture capitalist who for more than two decades invested at Benchmark in such defining startups as Uber and Zillow. He’s just published a new book titled, “ Runnin' Down a Dream: How to Thrive in a Career You Actually Love .” It’s based on his own personal story of how to avoid career regret, of sticking with a job way past the point of boredom.He’s joined in conversation by Lux’s own Josh Wolfe. The two talk about the book as well as the intersecting points of their long friendship and careers.
People in this episode
Host: Josh Wolfe
Guest: Bill Gurley
Topics covered
- career regret
- venture capital
- finding passion
- personal story
- job satisfaction
- entrepreneurship
Keywords
- career regret
- Bill Gurley
- venture capital
- job satisfaction
- personal story
- entrepreneurship
- Lux Capital
Mentioned in this episode
Organizations: Benchmark, Lux Capital
Books & works: Runnin' Down a Dream: How to Thrive in a Career You Actually Love
Places: America
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