10 Years of How I Built This: A Decade of Innovation, Risk and Reinvention

How I Built This · 5 Oct 2026 · 1h 10m

What this episode covers

Guy Raz and Jamie Siminoff, founder of Ring, review highlights from ten years of 'How I Built This,' discussing the emotional and financial struggles of founders like Sam Kalagani of Dogfish Head, Eileen Fisher, and Sarah Blakely of Spanx. They explore the distinction between scary and dangerous decisions, the importance of scrappy experimentation in products like Justin's Nut Butters and Liquid Death, and the psychological toll of fundraising rejections faced by founders of Whole Foods and Airbnb. The conversation emphasizes that failure and doubt are integral parts of building physical products, often requiring founders to persist through cash flow crises and technical failures before achieving market success.

Mentioned

Companies
Dogfish Head, Stitch Fix, Squarespace, Stonyfield, Whole Foods, Airbnb, Banana Republic, Chobani, Serena and Lily, Title 9, Bobbi Brown, NVIDIA, Shake Shack, Kinko's, Zoomies, Shopify, Dropbox, Weber
Products
Ring, Instagram, Dyson, Spanx, Liquid Death

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