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Diligence Questions


  • What led to the formation of this company?
  • Does the team have operating experience to measure?
  • What is the quality of the previous operating experience?
  • Do they have prior experience managing teams?
  • What are the founders’ unique skillsets to tackle this problem?
  • Do the founders have complimentary skill sets?
  • Can the founders work together?
  • How did the founders meet?
  • What is the expected window of opportunity for each founder (how long can they go with suppressed income)?
  • Is this an authentic idea that is true to the founders’ passion or a hollow attempt to make money?
  • Have the founders hired somebody before?
  • Do the founders have a network that allows them access to talent?
  • Are the founders charismatic enough to attract talent?
  • Are the founders based in a market that allows them access to talent?


  • Is the business model clear?
  • Who within the organization are you selling to?
  • Why do users care about the product / service you are offering?
  • Does the targeted person / role have authority to make purchasing decisions?
  • What is the value proposition?
  • Is the value created easy to measure or will it take time to market the ROI?
  • What organizations / people are you selling to?
  • What is the customer profile (role within the organization; demographics)?
  • What steps need to happen in order for a buying decision to be made?
  • Will target customers be able and willing to pay a fair price for your product?
  • Who is the largest customer today?
  • Who are the competitors?
  • Are you a first mover?
  • Is the product better, cheaper, or faster than existing solutions?
  • Is the product incrementally better or 10x better than alternatives?
  • What features do you offer that your competitors do not?
  • Why do your users care about these features?
  • What is your competitive advantage?
  • How defensible is this advantage?
  • How easy is it to replicate your competitive advantage?
  • Why would a buyer leave a competitor for you?
  • Is the company building on top of other platforms?
  • What is their relationship with the platform they are building on top of?
  • Are product plans in the direct path of the platform, or is it complementary?


  • Are you selling into an existing market, or are you creating a market?
  • Is the market large enough to for the company to capture a significant chunk of it?
  • What are the megatrends over the past 24 months that lead you to believe this is an expanding market?
  • Is there a shift in consumer behavior that strengthens this market?
  • What are the barriers to entry?
  • How strong are the barriers to entry?
  • Are there regulatory challenges within the sector?
  • Has investor interest increased or cooled off over the past few quarters?
  • Have investors already invested in a competitor?
  • Is the timing right and why?
  • Have other similar companies been formed before?
  • Why have other similar companies failed?


  • How much progress has been made towards product development?
  • Does the company have to create new tech, or are they building off of existing infrastructure?
  • Has the product been built in house, or is it outsourced?
  • Who is in charge of development?
  • Are there any patents pending or issued?
  • What is the product roadmap, and what new features are users asking for?
  • Is the product roadmap realistic and can it be executed in the proposed timeframe?
  • Can the largest customer influence pricing, product roadmap, etc.?


  • How much money does the company have in the bank?
  • What is the current monthly burn?
  • What is the burn rate going towards?
  • Does the company have enough time to meet its proposed goals?
  • How much runway does the company have before requiring additional money?
  • Is revenue assumed, or is there evidence that people / customers will buy your product / service?
  • Are customer contracts prepaid or not?
  • Are there different pricing tiers?
  • If there are different pricing tiers, which tier is most popular?
  • What metrics are you tracking?
  • How have these metrics changed over the past year?
  • Why are you focusing on these metrics?
  • What is the trailing top line growth over the past year?
  • What are the projected growth rates?
  • What assumptions are driving growth rates?
  • What percentage of revenue does the largest customer contribute?
  • How were existing customers / clients sourced?
  • What are the churn / retention numbers?
  • Have much of the company is still controlled by the founders?
  • How large is the ESOP (employee stock option plan)?


  • How are you planning to market to the specific users you are targeting?
  • What is your customer acquisition strategy cost today, and how do you see this strategy evolving?
  • How are you recuperating the acquisition costs?
  • Is there an opportunity to up-sell or cross-sell, or will LTV of the customer be derived from recurring revenue streams?
  • What steps are being taken to ensure you are solvent enough to reach your next milestones?
  • What are the biggest holes in your business today, and what steps are you taking to fill them?
Last modified 2yr ago