Bill Gurley: Legendary VC Rethinks Career Advice in 'Running Down a Dream'

Bill Gurley: Legendary VC Rethinks Career Advice in 'Running Down a Dream'

April 2, 2026 · 38 min · Season 11 · Episode 4

About this episode

Bill Gurley discusses his new book 'Running Down a Dream' and shares unconventional career advice.

Bill Gurley is a venture capitalist known for early investments in Uber, Grubhub, Zillow and many others. Gurley joins us to discuss "Running Down a Dream," his new book — which is full of career advice that is as surprising as it is useful. In this episode, we discuss: The Power of Mentorship: Why Bill feels a moral urge to share what he's learned with the world. The "Safe" Path Trap: Why the jobs your parents think are safe might actually be the most dangerous in the age of AI. The Peer Group Secret: Why sharing your best ideas with others actually makes you more successful than hoarding them. Finding Your Obsession: Why Bill looks for "fascination" rather than just "passion."

People in this episode

Guest: Bill Gurley

Mentioned in this episode

Organizations: Uber, Grubhub, Zillow

Books & works: Running Down a Dream

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