What do most people regret at the end of their careers? According to legendary venture capitalist Bill Gurley, it’s not the failures — it’s the risks they never took.

In this wide-ranging episode of The Puck, Jim Baer sits down with Gurley — longtime Benchmark partner, early Uber board member, and author of Running Down a Dream — for a candid conversation on boldness, bubbles, AI speculation, venture capital cycles, and America’s structural challenges.

Gurley reflects on:

- Why “boldness regret” weighs heavier than failure

- How to turn passion into mastery — and why most people don’t

- The resume arms race and why young people feel trapped

- AI: real revolution or speculative excess? (Hint: both)

- Venture capital’s evolution — from discipline to burn-at-all-costs

- Why five-year AI forecasts may set companies up to stumble

- Regulatory capture in healthcare and education

- State-by-state competition as America’s hidden advantage

From Austin’s music scene to Silicon Valley’s capital cycles, Gurley delivers battle-tested insights from decades at the center of tech’s biggest waves.

If you care about careers, markets, AI, or the future of the U.S. economy, this episode is essential listening.