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    Artwork for On with Kara Swisher
    Episode

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

    On with Kara Swisher · Feb 26, 2026 · 1 h 03 min

    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…

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