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
The Twenty Minute VC (20VC): Venture Capital | Startup Funding | The Pitch
The Twenty Minute VC
4.4 • 637 Ratings
🗓️ 16 June 2025
⏱️ 95 minutes
🧾️ Download transcript
Summary
Larry Aschebrook is the Founder and Managing Partner of G Squared in what is one of the wildest stories of venture capital. Larry started G Squared with nothing, dialling for dollars having personally invested in Twitter and Uber. In his first fund, Larry made sizable bets into SpaceX, Palantir, Alibaba and Twitter. Larry has also had mega losses along the way (discussed in the show) in Getir, 23andme and more. Today, Larry manages over $5BN and has invested in all the best from Wiz to Spotify to Revolut and Anthropic.
Agenda:
00:00 – From Broke to Billion-Dollar Bets
03:40 – The $800M Coursera Windfall
06:10 – Lyft Made Millions, Uber Lost $50M
09:05 – “We Fcked Up”: The Billion-Dollar Vintage
11:50 – How a $150M Spotify Bet Made a Billion
15:10 – The Gut Call That Dodged Theranos
18:00 – Vampires vs Zombies: The Coming Startup Purge
20:30 – When Success Almost Killed the Firm
24:20 – DPI Is King, MOIC Is Bullsht
27:40 – Why I’d Buy Anthropic at $61BN Today
30:05 – Losing $70M on 23andMe
32:10 – The Janitor of Venture Capital
34:00 – The Getir Deal That Nearly Broke Me
36:25 – Does Money Actually Make You Happy?
39:00 – What Cal Ripken Jr. Taught Me About Venture
Transcript
Click on a timestamp to play from that location
| 0:00.0 | I mean, we made ridiculous sums of money for LPs in that period. |
| 0:03.5 | We were the largest shareholder of Coursera, $800 million back to LPs on Coursera. |
| 0:09.1 | We made a ton of money on Lyft and we lost money on Uber. |
| 0:11.8 | 40% of my third fund went into Spotify. |
| 0:15.0 | I went back to our LPs and said, listen, we fucked up. |
| 0:17.7 | We need to pivot. |
| 0:18.7 | We need another 300 million box because I need to protect this thing. |
| 0:22.2 | The next three years were some of the worst of my life. |
| 0:25.9 | This is 20VC with me, Harry Stebbings. |
| 0:28.0 | Now, today we feature one of the most nut stories in venture capital. |
| 0:31.7 | I went for a walk with this guest before the show, |
| 0:34.7 | and it was just mind-blowing the different elements of their journey. |
| 0:39.0 | So we dive into its day, and I'm thrilled to welcome Larry Ashabrook, founder and managing partner |
| 0:43.3 | of G-squared, in what is, as I said, one of the wildest stories in venture, |
| 0:47.6 | Larry started G-squared with nothing, dialing for dollars, having personally invested in, |
| 0:52.9 | like Twitter and Uber. |
| 0:54.8 | And then in his first fund, he made sizable bets into SpaceX, Palantir, Alibaba and Twitter. |
| 1:02.3 | He also had mega losses along the way, which we discuss in the show in Gettier, 23 and Me. |
| 1:08.6 | He had a lawsuit with Theranos to get out of an investment there. And today, |
| 1:13.1 | he manages over $5 billion and he's invested in everyone from Wiz to Spotify to Revolut and |
| 1:19.6 | Anthropic. This is one of the best shows I've ever done. Because Larry's so honest, he's so real |
| 1:25.3 | and he's very candid with the numbers. This was an incredible show. |
... |
Please login to see the full transcript.
Disclaimer: The podcast and artwork embedded on this page are from The Twenty Minute VC, and are the property of its owner and not affiliated with or endorsed by Tapesearch.
Generated transcripts are the property of The Twenty Minute VC and are distributed freely under the Fair Use doctrine. Transcripts generated by Tapesearch are not guaranteed to be accurate.
Copyright © Tapesearch 2025.