What if the key to career success isn't following the safe path—but chasing the thing that gives you energy instead of draining it?

In this inspiring episode, host Aaron Lazar sits down with Bill Gurley—legendary venture capitalist, General Partner at Benchmark, early investor in Uber, Zillow, and OpenTable, and New York Times bestselling author of Runnin' Down a Dream: How to Thrive in a Career You Actually Love. From his days as a college basketball player at the University of Florida to leading the Amazon IPO as a Wall Street analyst to backing some of the most transformative companies in tech history, Bill shares the unconventional wisdom that took him a decade to distill into his first book.

This conversation is both a masterclass in career navigation and a deeply personal reflection on what it means to find your calling. Bill opens up about the humbling experience of realizing basketball wasn't his future, how that failure fueled his drive to find a field where he could truly thrive, and why he believes the people studying their craft out of obsession—not obligation—will always win.

The impossible dream shines brightest in Bill's six principles for career success: chase your curiosity, hone your craft, develop mentors, embrace your peers, move to the epicenter, and always give back. Through stories of Jerry Seinfeld, Danny Meyer, Kobe Bryant, and Steve Harvey, Bill reveals why giving yourself permission to dream—and having the methods to execute—changes everything.

Guest Bio:

Bill Gurley is a General Partner at Benchmark, one of Silicon Valley's most prestigious venture capital firms, where he has spent over two decades backing transformative companies. His investments include Uber, Zillow, OpenTable, GrubHub, Stitch Fix, and Nextdoor. Before venture capital, Bill was a top-ranked Wall Street research analyst at CS First Boston, where he led the Amazon IPO. He earned his Bachelor of Science in Computer Science from the University of Florida—where he played on the men's basketball team—and his MBA from the University of Texas at Austin, which awarded him the Distinguished Alumnus Award in 2025. Bill's blog Above the Crowd has shaped industry thinking on technology, marketplaces, and investing for over two decades. His first book, Runnin' Down a Dream, became a New York Times bestseller. Bill lives in Austin, Texas with his wife and three children.

Learn more about Bill Gurley:

Above the Crowd Blog

Runnin' Down a Dream (Penguin Random House)

Benchmark Capital

LIVE YOUR IMPOSSIBLE DREAMS

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