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

Larry Aschebrook of G Squared explains how a $150M concentrated Spotify bet returned ~$1B to LPs while losing $50M on Uber and making 3x on Lyft.

• G Squared’s $150M Spotify position (40% of Fund 3 at $380M) plus $700M in co-invests returned ~$1B to LPs, making it a top multiple alongside early Wiz.
• Lost ~$50M on Uber (sold post-IPO underwater) while making ~3x on Lyft by selling most shares before the IPO.
• G Squared was Coursera’s largest shareholder and returned $800M to LPs on that position alone.
• Aschebrook would buy Anthropic at $61B today and is actively accumulating; he’d put his entire fund into OpenAI at $350B valuation, projecting $1.5T in 5 years.
• Aschebrook dodged Theranos via productive paranoia but lost ~$70M on 23andMe and estimates the 2020 vintage co-investment mistakes cost the firm ~$500M in lost capital and LP relationships.
• G Squared strategy: 80-90% of risk concentrated in 10 companies across four mega-trends — SaaS, fintech, consumer internet, mobility — entered via small secondary positions as Trojan horse for data access.
• Aschebrook warns that hundreds of large private companies are ‘zombies’ that cannot survive the AI transition; vampires (profitable, adaptable incumbents) are far rarer than people assume.
• TVPI and MOIC are, in his view, meaningless vanity metrics — DPI is the only number that matters because it is the only one you can spend.

2025-06-16 · Watch on YouTube