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Background & History

  • How did you meet COFOUNDER and where did the idea for COMPANY come from?
  • How long have you worked together?
  • Where did the motivation for working on COMPANY come from?
  • Why did you pick your co-founder?
  • What does the cap table look like? (equity distribution between founders, in particular)
  • When was the last time you disagreed on a meaningful business issue? How did you resolve it?
  • Do you have a demonstrated history of building things (in whatever capacity you are capable of)?

Problem & solution

  • What is the specific problem you are solving?
  • Who has this problem?
  • Why is this a problem?
  • How big / serious of a problem is it?
  • How are people solving this problem today?
  • Describe your solution to this problem and your product. What is your product's "wedge"?
  • What is your product roadmap for the next 6-12 months? What is the larger opportunity you're trying to capture in your product roadmap?

Market-timing

  • Why is now the right time for this product/company? Why hasn’t this worked / been done before?

Go-to-market

  • Describe your user persona(s) to me (end user, buyers, etc)?
  • What does a day-in-a-life look like for these people?
  • How much are people paying today? (range?)
  • How much do you think you can charge in the future if you aren't charging today?
  • How are customers discovering your product? Through what channels?
  • How much does it cost you currently to get a user? And in which channel?
  • What effort / timing is required to switch from a different solution to yours?
  • How are customers going to discover your product in the future? Through what channels?
  • How much does your solution/product cost to make?
  • How much will it cost in the future?
  • What is the sales cycle?
  • How does the product team interact with current and potential customers? If so, how and how often?
  • What do the unit economics look like? Margins?

Competitive landscape

  • What differentiates your product from alternatives?
  • Who do you see as competition? Why/why not COMPETITOR?

Traction

  • How many customers/users/contracts do you have?
  • What is the nature of any contracts (pilots, paid, enterprise etc?)
  • How much revenue have you generated to date (is it real product revenue or services revenue)?
  • What does retention or churn look like? (if you know)
  • What does engagement look like?
  • When will your company break even in terms of profitability and cash flow?

Fundraise & future plans

  • How much have you raised to date? From whom?
  • What were the terms of those raises?
  • How much are you looking to raise now?
  • What are you looking to achieve (milestones) with this round if everything goes well?
  • Who do you need to hire during the next 18 months to be successful?
  • How are you going to spend the money you raise?
  • Where are you in the process of putting together your round?
  • Have the current terms been set? And if so, what are they?
  • What is your burn rate? How big is the team? How far does the new money get you?
  • What is your top priority for the next 3-6 months?
  • What do you want from your investors in this round?