Larry Aschebrook, Founder & MP @GSquared: How We Lost Money on Uber and Made Millions on Lyft

Channel:

20VC with Harry Stebbings

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176,000

Published on June 16, 2025 1:57:08 PM ● Video Link: https://www.youtube.com/watch?v=BiJSLd-qzCA

Duration: 0:00

6,401 views

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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.
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In Today’s Episode We Discuss:

00:00 Intro
01:07 Bootstrapping a Venture Career
04:41 The Best Investment on a Multiple Basis
09:29 The Alibaba Move That Changed Everything
20:19 How a $150M Spotify Bet Made a Billion
30:33 Lyft Made Millions, Uber Lost $50M
41:53 “We Fcked Up”: The Billion-Dollar Vintage
47:19 What Larry Does with Overinflated Assets
50:51 The Gut Call That Dodged Theranos
59:13 Losing $70M on 23andMe
01:02:42 The Getir Deal That Nearly Broke Me
01:05:57 The Janitor of Venture Capital
01:19:07 Getting To Revolut in 2018
01:24:21 Why I’d Buy Anthropic at $61BN Today
01:27:15 Vampires vs Zombies: The Coming Startup Purge
01:34:06 Does Money Actually Make You Happy?
01:39:18 Quick-Fire Round
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