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…
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 advantageFrom 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.