On with Kara Swisher

Why ‘Playing It Safe’ In Your Career Doesn’t Pay with VC Bill Gurley

February 26, 2026·1h 3m·3-min readinterviewbusiness
Podzilla Summary (3 min)
TLDR
Bill Gurley, a legendary venture capitalist and author of Running Down a Dream, shares insights on building a career you love by embracing curiosity, surrounding yourself with driven peers, and rejecting societal pressures to chase safe but unfulfilling jobs. He argues that passion, far

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Guest

B

Bill Gurley

interview on On with Kara Swisher

Mentions

Books, people, and resources mentioned in this episode.

People

Bill GurleyKara SwisherDara KhosrowshahiMatthew McConaugheyAngela DuckworthTony Fadell

Books

Running Down a Dream: How to Thrive in a Career You Actually Loveby Bill GurleyAtomic Habitsby James ClearThe Coddling of the American Mindby Jonathan Haidt

Companies

Benchmark Capital

Topics

Artificial IntelligenceCareer DevelopmentEntrepreneurshipFuture Of WorkLeadershipPersonal FinanceStartupsVenture Capital

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