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Start-Ups Always Look Great, Plan for the Worst with Jen Greyson

Background: Jen Greyson

  • Founder and CEO of, the Airbnb of office space
  • One of the top eight women in crypto
  • A “genius at failure”
  • Speaks internationally on AI and female tech entrepreneurship

Jen’s worst investment ever

  • Chance meeting with computer engineer on quest to create AI “for the good of humanity”
  • Falls in love with the idea
  • Becomes investor and CEO to re-invent corporate world
  • Costs sink in as deadlines pass and keep passing
  • Major complications hit
  • Mentor asks hard “zero-based thinking” question
  • Jen eventually realizes she must resign

Jen’s takeaways

  • Live a life with no regrets
  • Look at every situation as a learning opportunity
  • Always get everything in writing
  • Always assume a start-up is going to go bad
  • Always have an exit strategy
  • Be close with the others in a start-up

My takeaways

  • Investing in start-ups is a very high-risk activity
  • CEOs may be risking everything
  • Zero-based thinking is a valuable mental tool
  • My model to assess start-ups, TIEM
  • Trust: Do I trust the founder/s?
    • If there’s no trust – STOP
  • Idea: Is it a good idea?
    • If it is not – STOP
  • Execution: Can they execute?
    • If no – STOP
  • Money: If no money, you won’t get there
    • If no – STOP

Actionable advice

  • Trust your gut
  • Set deadlines and solid penalties for when they are not met

My Worst Investment Ever six main categories of mistakes:

  1. Failed to do their own research
  2. Failed to properly assess and manage risk
  3. Were driven by emotion or flawed thinking
  4. Misplaced trust
  5. Failed to monitor their investment
  6. Invested in a start-up company

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DISCLAIMER: This content is for information purposes only. It is not intended to be investment advice. Readers should not consider statements made by the author(s) as formal recommendations and should consult their financial advisor before making any investment decisions. While the information provided is believed to be accurate, it may include errors or inaccuracies. The author(s) cannot be held liable for any actions taken as a result of reading this article.