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

ℹ️ EPISODE INFO

Released

June 16, 2025

Duration

1h 47m

Channel

The Twenty Minute VC

Watch on YouTube

▶ Open ↗

📝 EPISODE DESCRIPTION

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. ---------------------------------------------- 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 ----------------------------------------------- Subscribe on Spotify: https://open.spotify.com/show/3j2KMcZTtgTNBKwtZBMHvl?si=85bc9196860e4466 Subscribe on Apple Podcasts: https://podcasts.apple.com/us/podcast/the-twenty-minute-vc-20vc-venture-capital-startup/id958230465 Follow Harry Stebbings on X: https://twitter.com/HarryStebbings Follow Larry Aschebrook on X: https://twitter.com/LarryVCg2 Follow 20VC on Instagram: https://www.instagram.com/20vchq Follow 20VC on TikTok: https://www.tiktok.com/@20vc_tok Visit our Website: https://www.20vc.com Subscribe to our Newsletter: https://www.thetwentyminutevc.com/contact ----------------------------------------------- #20vc #harrystebbings #larryaschebrook #gsquared #founder #partner #vc #lyft #spotify #twitter #coursera

🎤 SPEAKERS

• Larry Aschebrook

  guest

• Harry Stebbings

  host

• Narrator

  other

🧾 EPISODE SUMMARY

In this episode of The Twenty Minute VC, featuring Larry Aschebrook and Harry Stebbings, Larry Aschebrook, Founder & MP @GSquared: How We Lost Money on Uber and Made Millions on Lyft explores from Trailer Park To Tech Titan: G Squared’s Wild Ride Larry Aschebrook, founder of G Squared, recounts his unconventional path into venture and growth investing, starting from buying secondary shares in elite tech companies with his last savings and no formal VC background.

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