Stories about starting a business are almost always full of drama. They’re about ambition, loss, triumph, catastrophe, resilience. And they’re also full of life lessons – which is why Guy Raz launched How I Built This 10 years ago: He wanted to host a free master class in entrepreneurship, one conversation at a time. Ten years on, he’s conducted over 600 interviews with some of the world’s most successful founders, and on today’s show, he replays some of the most memorable moments and lessons. Joining him is Jamie Siminoff, the founder of RING and a former guest on the show. Why Jamie? He’s a friend, a fan, and – as you may remember from his first interview - he doesn’t hide his emotions.

Timestamps:

5:10 A lightbulb switches on at an NYC bodega: “Oh my God, look at all those cherries!” 

9:33 The moment Stitch Fix founder Katrina Lake realized she should start her own business.

12:04 The difference between scary and dangerous, and why it matters for founders

19:35 Eileen Fisher’s first, terrifying trade show: “I couldn’t speak. I just stood there.”

22:59 “Everything was on one computer?” The chaotic launch of Instagram

27:32 How Sara Blakely sold her first Spanx

31:16 The marketing genius behind Liquid Death

39:40 Why 2008 was the worst year of Joe Gebbia’s life

44:51 How the co-founder of Banana Republic fell asleep at the wheel—literally

53:40 Makeup mogul Bobbi Brown on selling to Estee Lauder: “I am not a follow-the- leader-kind of person.”

1:01:59 Luck, skill, and staying on the surfboard

This episode was produced by Casey Herman, with music by Ramtin Arablouei.

Edited by Neva Grant. Our audio engineer was Robert Rodriguez.

Follow How I Built This:

Instagram → @howibuiltthis

X → @HowIBuiltThis

Facebook → How I Built This

Follow Guy Raz:

Instagram → @guy.raz

Youtube → guy_raz

X → @guyraz

Substack → guyraz.substack.com

Website → guyraz.com

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