O'Driscoll: Anti-portfolio regret is the price of good deal flow
Rory O'Driscoll · How Do All Providers Deal with Anthropic Dependency Risk & Figma IPO Breakdown: Where Does it Price? · 20VC with Harry Stebbings · Jul 24, 2025 · at 59:07
Rory O'Driscoll (General Partner at Scale) discusses venture investment dynamics and the psychological burden of passing on successful companies with Harry Stebbings.
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“Anti portfolio regret is the psychological price you have to pay for being in the game because it's literally the emotional tax you pay for being in good deal flow. Because if you're not seeing 10 great deals, you're probably not going to do one great deal, which means the psychological tax for doing one great deal is you pass on nine deals or you don't win them.”
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