On with Kara Swisher Why ‘Playing It Safe’ In Your Career Doesn’t Pay with VC Bill Gurley
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Feb 26, 2026 
Bill Gurley, longtime Silicon Valley venture capitalist and early Uber backer, shares career advice from his book Running Down a Dream. He argues for finding fascination through experiments, starting at the bottom, and honing craft with peers and mentors. He also discusses AI-related job anxiety, why being near talent creates opportunity, and growing concern about tech’s political power and regulation.
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MrBeast Peer Group Fueled Rapid Growth
- MrBeast found three peers online and they co-learned via Skype 17 hours a day for four years, which accelerated success.
- All four reached over a million followers and became millionaires, illustrating peer group multiplier effects.
Find A Peer Cohort Outside Your Company
- Seek peers at your same rung who share ambition and share ideas, networks, and emotional support.
- Gurley recommends peers preferably outside your company to avoid internal politics and amplify learning.
Newport Festival Director Started With One-Way Ticket
- Jay Sweet quit teaching, bought a one-way ticket to Ecuador, and eventually ran the Newport Folk Festival earning $16,000 his first year.
- Gurley uses this to show many flourish after long, non-linear journeys starting at the bottom.
