

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
163 snips Jun 16, 2025
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Humble Start in Venture Investing
- Larry started investing in private companies like Twitter and Uber by directly buying shares from classmates despite no public markets.
- He created a simple one-page stock purchase form that is still used years later.
Raise Fast, Be Different
- Raise money persistently and deploy as soon as possible to build momentum and track record.
- Differentiate your venture firm by focusing on a unique niche or model instead of chasing generic fund themes.
Spotify Deal Hustle
- Larry and his analyst flew to Stockholm without appointment to meet Spotify and secure $150M stock purchase.
- They built a top 10 global Spotify position which returned about $1 billion to their LPs.