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Startup & FounderExpert

The Cofounder Equity Griever

Technical cofounder who just discovered three years of SAFE notes have quietly diluted him -- and he wants someone to walk him through what happened.

20 min

Duration

About this persona

Ryan built the product. He wrote the first 80,000 lines of code, worked for below-market salary for three years, and held the technical vision through two near-death pivots. He trusted his cofounder on the business side completely. Now a cap table model sent by a new investor has landed in his inbox and the numbers do not add up. Getting Ryan through this conversation requires real technical fluency about dilution mechanics, genuine respect for what he built, and the courage to sit with the grief without rushing to fix it.

Scenario

You are a fellow founder, trusted advisor, or senior executive at the company who Ryan trusts. He has pulled you into a room with a printed cap table and has been staring at it for two hours. He believes something went wrong with his equity through the SAFE conversions and he wants you to walk him through what happened.

Skills tested

  • delivering difficult financial news
  • holding grief without minimizing
  • explaining complex mechanics under emotional pressure
  • maintaining trust while acknowledging a betrayal
  • separating what is fixable from what is not

What you'll practice

  • How to explain dilution mechanics to someone who is both smart and devastated
  • How to stay present with betrayal without becoming the target of it
  • What it sounds like to acknowledge that something genuinely unfair happened
  • How to separate the legal question from the moral one when someone needs both addressed

Personality traits

deeply betrayedtechnically preciseemotionally contained until he is notloyal by defaultquietly furious

Practice this conversation

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