Insight certainty 5/5 debate potential 2/5

Founders Never Regret Firing Someone, Only That They Waited Too Long

Katelin Holloway · Katelin Holloway – Human Side of Venture Investing at 776 (EP.490) · Mar 9, 2026 · at 56:09

Katelin Holloway, founding partner at Seven Seven Six, discusses why early-stage founders struggle with moving quickly on terminating underperforming employees.

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“Never once in my multi-decade career of hiring and firing people and supporting founders and entrepreneurs and builders has anyone ever come to me and said, I regret letting that person go. What they do say 10 out of 10 times is, oh my god, I should have done that sooner.”

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