1. Why haven’t you raised the amount you’re seeking already?
  2. What’s to stop a bigger player from completely crushing your company?
  3. What are your unfair advantages?
  4. What’s your cost per customer acquisition?
  5. What’s your endgame… You want to sell your company or take it all the way to a public offering?
  6. What’s the size of the market?
  7. Why you? Why not someone with more experience in this field?
  8. Besides making money, why are you pursuing this business?
  9. How could this benefit other companies in our portfolio?
  10. Is your CEO replaceable?
  11. Are there any patents in here?
  12. Who are your key strategic partners?
  13. Who’s your primary and secondary targeted demographic?
  14. How much money (exactly) are you raising and where’s it all going?
  15. How can you do everything you’re doing, but for cheaper?
  16. What are the primary risks associated with your business and how are you handling them?
  17. What’s your first year burn?
  18. Who’s going to sue you?
  19. Who’d handing your legal and accounting right now?
  20. You’re a C-corp… Have you filed your 87B?
  21. Are any of the issued shares in your company non-dilutable?
  22. What’s your go-to-market strategy/ How are you expanding your current market reach?
  23. If this company failed, what would you do?
  24. Who are your current competitors and how do you differentiate?
  25. How have you proven that all the assumptions about your business are as close to being accurate as they can be?
  26. If I made an offer to buy your business today, at 10x its current value, would you take the offer?
  27. How are you going to do dividends?
  28. How much are you paying yourself and why?
  29. What psychological impulse are you tapping into with your customer to get them to buy?
  30. Do you have customer referrals and testimonials we can put on the site?