All episodes of The Twenty Minute VC (20VC): Venture Capital | Startup Funding | The Pitch

The Twenty Minute VC (20VC): Venture Capital | Startup Funding | The Pitch · 2025-06-16 · 95 min · 19,465 words

20VC: How We Made $800M on Coursera | We Lost Money on Uber and Made Money on Lyft | We Did 3x on Postmates in 18 Months | DPI is King, MOIC is BS | We Dodged Theranos and I Still Lost Millions with Larry Aschebrook @ G Squared

Listen to the original audio · Transcribed with NVIDIA Parakeet · Timestamps stay in sync with the live audio

I mean, we made ridiculous sums of money for LPs in that period. We were the largest shareholder of Coursera. $800 million back to LPs on Coursera. We made a ton of money on Lyft and we lost money on Uber. 40% of my third fund went into Spotify.

I went back to our LPs and said, listen, we fucked up. We need to pivot. We need another 300 million bucks because I need to protect this thing. The next three years were some of the you know worst of my life.

This is 20 VC with me, Harry Stebbings. Now today we feature one of the most nut stories in Venture Capital. I went for a walk with this guest before the show and it was just mind-blowing the different elements of their journey. So we dive into it today and I'm thrilled to welcome Larry Asherbrook, founder and managing partner of G Squared, in what is, as I said, one of the wildest stories in Venture. Larry started G Squared with nothing, dialing for dollars, having personally invested in like

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