David Cohen (founder of Techstars) was an angel investor in Uber. He also had the opportunity to invest in Lyft — and passed. Same market. Same timing. Two completely different outcomes in his portfolio.

The difference? At Uber, he met Ryan Graves (the first employee) through Techstars. “I clicked with him.” He invested without ever meeting Uber’s founders.

At Lyft, Matt Van Horn was a mentor at Techstars. They were friends. But the idea seemed stupid to him: “Intercity transportation for college students? I didn’t get it.”

That same team pivoted, followed Uber, and built a multi-billion-dollar company.

After 20 years evaluating startups, the pattern behind his misses is always the same.

Also in this episode:

Why AI creates a "barbell effect" for startups — the middle gets stuck
Techstars’ internal meme: “Replace ‘AI’ with ‘software’”
Why AI agents will do venture capital — and probably better than humans
Jack Bogle’s philosophy applied to VC: “The financial industry only subtracts value”

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David's LinkedIn: https://www.linkedin.com/in/davidgcohen/

Enzo's LinkedIn: https://www.linkedin.com/in/enzo-cavalie/

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