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

Bill Gurley, accomplished venture capitalist, longtime Silicon Valley “worrywart,” and early Uber backer, joins Kara Swisher to discuss how to build a career you love and the tech industry’s sharp turn to the right. Gurley’s new book Runnin’ Down a Dream, guides readers on how to find and nurture a truly fulfilling career — and his advice is the polar opposite of Scott Galloway’s “follow your talent, not your passion.” Kara and Bill talk about how to find your fascination, and why the best careers are built through craft, peers, mentors, and a willingness to start at the bottom. They also dig into AI-related job loss anxiety and Gurley’s growing focus on public policy — from regulatory capture to the concentration of power in the Mag 7. Plus: an expert question from Uber CEO Dara Khosrowshahi. Questions? Comments? Email us at on@voxmedia.com or find us on YouTube, Instagram, TikTok, Threads, and Bluesky @onwithkaraswisher. Learn more about your ad choices. Visit podcastchoices.com/adchoices

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Why ‘Playing It Safe’ In Your Career Doesn’t Pay with VC Bill Gurley is an episode from On with Kara Swisher by New York Magazine.

This episode is 63:25 long.

This episode was published on Feb 26, 2026.

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