
Why ‘Playing It Safe’ In Your Career Doesn’t Pay with VC Bill Gurley
From On with Kara Swisher
Published 2/26/2026

From On with Kara Swisher
Published 2/26/2026
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…