30 Years in 30 Minutes

From Pinterest to Airbnb: Inside Rick Heitzmann’s Formula for Betting on the Next Great Founder (Part 2)

Michael Oved Season 2 Episode 4

What makes a great founder? Why do some startups become category-defining companies while others disappear? In this episode, Rick Heitzmann reveals the mental models, pattern recognition, and non-obvious signals he’s used to back Pinterest, Airbnb, Riot Games, DraftKings, and more. Part 2 goes deeper into founder psychology, pitch strategy, market timing, and the traits that predict generational success. This is one of the clearest breakdowns of venture decision-making you’ll ever hear.

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