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

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

Larry AschebrookguestHarry Stebbingshost
Jun 16, 20251h 47mWatch on YouTube ↗

CHAPTERS

  1. 0:00 – 1:07

    Intro

  2. 1:07 – 4:41

    Bootstrapping a Venture Career

  3. 4:41 – 9:29

    The Best Investment on a Multiple Basis

  4. 9:29 – 20:19

    The Alibaba Move That Changed Everything

  5. 20:19 – 30:33

    How a $150M Spotify Bet Made a Billion

  6. 30:33 – 41:53

    Lyft Made Millions, Uber Lost $50M

  7. 41:53 – 47:19

    “We Fcked Up”: The Billion-Dollar Vintage

  8. 47:19 – 50:51

    What Larry Does with Overinflated Assets

  9. 50:51 – 59:13

    The Gut Call That Dodged Theranos

  10. 59:13 – 1:02:42

    Losing $70M on 23andMe

  11. 1:02:42 – 1:05:57

    The Getir Deal That Nearly Broke Me

  12. 1:05:57 – 1:19:07

    The Janitor of Venture Capital

  13. 1:19:07 – 1:24:21

    Getting To Revolut in 2018

  14. 1:24:21 – 1:27:15

    Why I’d Buy Anthropic at $61BN Today

  15. 1:27:15 – 1:34:06

    Vampires vs Zombies: The Coming Startup Purge

  16. 1:34:06 – 1:39:18

    Does Money Actually Make You Happy?

  17. 1:39:18 – 1:47:28

    Quick-Fire Round

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