10 Years of How I Built This: A Decade of Innovation, Risk and Reinvention
Oct 5, 2026 · 1h 10m
Summary
For its 10-year anniversary, How I Built This host Guy Raz joins Ring founder Jamie Siminoff to revisit iconic episodes featuring founders like Sarah Blakely, James Dyson, and Sal Khan. They discuss how fear fuels entrepreneurship, the importance of scrappy experimentation, and the resilience required to overcome rejection and failure. The conversation highlights stories from Instagram, Spanx, and Airbnb to illustrate that setbacks are often essential steps toward building successful, transformative businesses.
Topics discussed
Sponsors and show introduction
10-year anniversary and guest Jamie Siminoff
The psychology of starting a business
Fear, risk, and the immigrant founder experience
Obsessive experimentation and early failures
Sponsor segments: NetSuite, Framer, Stripe
Lessons from early episodes: failure and heroism
Scrappy origins: Spanx, Ring, and Liquid Death
Stonyfield Yogurt: borrowing from family and persistence
Whole Foods and the art of the sales pitch
Luck vs. skill and the emotional toll of failure
Growth strategies: singles vs. grand slams
Selling your company and the NVIDIA story
Business as an instrument: Paul Graham's advice
The role of luck and timing in success
Future of the show and production credits
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