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
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
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
Larry Aschebrook, Founder and Managing Partner of G Squared, shares his journey from humble beginnings to managing over $5 billion in investments. Known for bold bets on companies like SpaceX, Palantir, Alibaba, and Twitter, Larry also discusses significant losses and the lessons learned along the way. His unique approach to venture capital emphasizes strategic investments, liquidity management, and avoiding common pitfalls.
Larry Aschebrook's rise in venture capital is marked by both successes and failures. He started G Squared with minimal resources but achieved substantial returns through investments in Coursera, Spotify, Lyft, and others. Despite losing $50 million on Uber and $70 million on 23andMe, Larry attributes his success to strategic decision-making and avoiding herd mentality. A pivotal moment was investing in Spotify despite challenges, which resulted in a billion-dollar return. Larry emphasizes the importance of DPI (Distributed to Paid-In) over MOIC (Multiple of Invested Capital), highlighting liquidity management as crucial for investor satisfaction. He reflects on mistakes made during market peaks, such as overpaying for Toast, and stresses the need for guardrails in investment strategies. Larry also discusses the direct secondary buying business model, focusing on undervalued assets and maintaining close relationships with founders. Looking ahead, he remains optimistic about opportunities in fintech, AI, and other megatrends, showcasing a diversified approach to risk.
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Larry started as a fundraiser before entering venture capital
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Started buying shares of early Uber, Twitter, and Spotify during business school
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Fewer institutions helped companies go public post-crisis.
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Diversified entry strategy focuses on fewer companies for liquidity
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Past funds allowed acquiring assets at 35 cents on the dollar
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Direct secondary buyers interact with founders and access primary-level data.
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Using the mosaic theory for due diligence in early-stage investments.
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Invested $380M in Spotify, turning it into a billion-dollar outcome.
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Tripled down on an investment at a 50% discount, reaching a 380-million-dollar pool.
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Lost 20 cents on the dollar in Uber but made 3x on Lyft.
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Companies reaching high valuations and avoiding cycle ends is crucial.
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The manager argues they're doing what they're hired for, generating capital velocity.
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Got $800M back to LPs on Coursera and exited Toast at $76 per share
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Avoided a disastrous Theranos investment by trusting his 'Spider sense'.
