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The Operator's Edge: From San Diego Angel Academy

What Angel Investors Learn by Losing

Angel Academy Session 3 brings together a panel of San Diego operators who crossed over to the investor side - including Katherine Chapin, Dane Chapin, Ken Potashner, and Bardia Moayedi with backgrounds spanning investment banking, corporate law, and consumer products. The conversation gets honest fast: what it means to bet on a founder who introduces herself as "just a mom," why losing money on a deal teaches you more than any pitch deck, and how San Diego's open, collaborative angel community creates a fundamentally different deal flow than Silicon Valley's closed-door networks.

Key Topics

  • Operating experience as an angel investor's real edge

  • The "just a mom" story: why passion beats pedigree every time

  • Dane Chapin's board game company postmortem and what losing taught him

  • San Diego's open angel ecosystem vs. Silicon Valley's closed networks

  • Underestimating risk: the Coin investment and what it revealed

  • Co-investing with spouses and building shared conviction

  • Why brand obsession signals a founder worth backing

  • Pitch contests vs. relationship-driven deal flow

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