AI Summary
→ WHAT IT COVERS Three venture investors share passed investment opportunities including Uber and Replit, revealing decision-making mistakes and lessons about conviction, market sizing, and communicating investment thesis to partners. → KEY INSIGHTS - **Market sizing errors:** Investors commonly underestimate markets by focusing on initial narrow use cases rather than expansion potential, as demonstrated by dismissing Uber as serving only finance professionals ordering black cars. - **Go-to-market complexity:** Long, multi-stage customer acquisition plans like targeting university students first then translating to enterprise typically fail, making simpler direct routes more investable despite potentially smaller initial markets. - **Conviction communication:** Junior investors must explicitly state belief strength to partners by saying they would invest personal funds or retirement accounts, not passive suggestions, to get deals approved and avoid regret. → NOTABLE MOMENT An investor deliberately avoided networking with Uber's early CEO at a baseball game to prevent being pitched on what seemed like a service for stuck-up finance professionals. 💼 SPONSORS [{"name": "Ramp", "url": "https://ramp.com/partner/tfr"}, {"name": "American Arbitration Association", "url": "https://adr.org/tfr"}] 🏷️ Venture Capital, Anti-Portfolio, Investment Decisions