The Full Ratchet (TFR): Venture Capital and Startup Investing Demystified Investor Stories 426. Investor Regrets and Hard Calls: From Tax Credit Dependence to Saying No to Zoom (Hsieh, Delk, Hilaly)
Sep 11, 2025
Three investors share their stories of missed opportunities and the lessons learned from deciding not to invest. They discuss the importance of focus to avoid distractions that lead to regret. Notably, one recounts passing on an early chance with Zoom, emphasizing the need for thorough assessment of a founding team's leadership. Additionally, the concept of 'anti-portfolios' is explored, revealing how these experiences can shape better investment strategies in the future.
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Trust Your Gut On Market Risk
- Trust your gut when regulatory risk feels too high for your fund's risk tolerance.
- But remember that high-quality founders may still navigate changes and create value.
Regulatory Risk Can Kill Conviction
- Vince Hsieh passed because the business relied heavily on changing tax credits and regulation.
- He notes that despite the risk, a strong founding team can pivot and still succeed.
Missed Deals From Not Prioritizing
- Ryan Delk missed investing in smart friends twice because he couldn't prioritize those rounds during busy Primer periods.
- He calls the missed opportunities painful but acceptable given his time allocation choices.