Shiv Gettu sits down with Spencer Rascoff, co-founder of Hotwire and Zillow, as he shares his journey from competitive chess player to transformative tech leader.

From facing potential business collapse after 9/11 to scaling Zillow into a household name, Spencer provides candid insights about founder psychology, navigating crises, and the delicate balance between optimism and pragmatism in leadership.

Through stories of teaching entrepreneurship at Harvard and building multiple successful companies, he challenges conventional wisdom about founder archetypes and shares his perspective on manufacturing adversity, raising resilient kids, and finding the right path to entrepreneurship.

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00:00 Early Life & Chess Career08:00 Family Background & Music Industry19:30 Hotwire Journey & Post-9/11 Crisis28:00 Building Zillow36:00 Leadership Philosophy & Growth50:00 Teaching Entrepreneurship at Harvard