Andy Chen: The Convenient Cofounder Penalty episode artwork

EPISODE · Jun 10, 2026 · 22 MIN

Andy Chen: The Convenient Cofounder Penalty

from Sand Hill Road · host Scott McGrew, Andy Chen

Andy Chen of Outcast Ventures spent 15 years at Kleiner Perkins and Coatue studying what actually makes startups succeed — and the data surprised him. After analyzing every U.S. IPO and acquisition over $1 billion in the past two decades, Chen found that founders who didn't know each other beforehand built more valuable companies than those who did. He calls the trap the "convenient co-founder penalty." Now he's doing something about it: Catalyst, a co-founder formation program launching this week, brings together pre-vetted, high-caliber talent to find the right match before the company even exists. Chen also discusses the rise of AI-era solo founders, why elite schools don't predict bigger exits, and his own unlikely path — from CIA nuclear weapons analyst to venture capitalist. Hosted by Simplecast, an AdsWizz company. See pcm.adswizz.com for information about our collection and use of personal data for advertising.

Andy Chen of Outcast Ventures spent 15 years at Kleiner Perkins and Coatue studying what actually makes startups succeed — and the data surprised him. After analyzing every U.S. IPO and acquisition over $1 billion in the past two decades, Chen found that founders who didn't know each other beforehand built more valuable companies than those who did. He calls the trap the "convenient co-founder penalty." Now he's doing something about it: Catalyst, a co-founder formation program launching this week, brings together pre-vetted, high-caliber talent to find the right match before the company even exists. Chen also discusses the rise of AI-era solo founders, why elite schools don't predict bigger exits, and his own unlikely path — from CIA nuclear weapons analyst to venture capitalist.

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Andy Chen: The Convenient Cofounder Penalty

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This episode was published on June 10, 2026.

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Andy Chen of Outcast Ventures spent 15 years at Kleiner Perkins and Coatue studying what actually makes startups succeed — and the data surprised him. After analyzing every U.S. IPO and acquisition over $1 billion in the past two decades, Chen found...

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