Self explanatory?

The following is a comprehensive list of questions I’ve come across in my experience pitching and raising money for startups, and from those of other budding and seasoned entrepreneurs.

Everything from “Why should I care about your product or service?” to “What happens to my money if you get divorced?”, all segmented into their respective categories.


Products & Services

  1. What is your business model?
  2. Why do users care about your product or service?
  3. Why should I care about your product or service?
  4. What are your major product milestones?
  5. What are the biggest changes your company has gone through in the past 3, 6 and 12 months?
  6. What are the key differentiated features of your product or service?
  7. What is your value proposition?
  8. What is your distinctive competency?
  9. What have you learned from early versions of your product or service?
  10. Provide a demonstration of your product or service.
  11. What are the two or three key features you plan to add? And how do they benefit users/consumers?
  12. What are the advantages of using your product/service?
  13. How can I make money?

Founder(s) & Team:

  1. What is your vision for the company?
  2. Who are the founders and key team members?
  3. Why start this venture?
  4. Your relationship with your technical team is unclear, please elaborate.
  5. What relevant domain experience does the team have?
  6. What key additions to the team are needed in the short-term/long-term?
  7. What are your personal strengths and weaknesses?
  8. Why is your team uniquely capable of executing the company’s business plan and vision?
  9. How many employees do you have?
  10. What motivates you? What motivates the founders?
  11. What keeps you awake at night?
  12. What is the starting salary for your technical team?
  13. How much are you paying yourself?
  14. How do you plan to scale the team in the next 12 months?
  15. How much equity will you reserve for employees?
  16. What happens to my money if you divorce? (when founders are married)
  17. Why are you the team to execute on this idea.


  1. Who is your ideal customer?
  2. What do your customers need and how do you know?
  3. What is your total available market?
  4. What is your total addressable market (how large is the market opportunity, in relation to your proposed sales and distribution channels)?
  5. What percentage of the market are you expecting to acquire? How long?
  6. How did you arrive at the sales values and growth rate of your industry?
  7. Why does your company have high growth potential?
  8. Who owns the customer?


  1. Who are your competitors?
  2. How easy is it for new entrants to enter your market?
  3. What is the level of rivalry in the industry at the moment?
  4. What substitute products and alternatives already exist?
  5. What gives your company a competitive advantage?
  6. What advantages does your competition have over you?
  7. Compared to your competition, how do you compete with respect to price, features, and performance?
  8. What are the barriers to entry?
  9. What concerns you most about the competitive landscape of your industry?

Marketing & Customer Acquisition

  1. What is your principle marketing strategy?
  2. What is your price?
  3. How did you derive the price of your product?
  4. How much money do you have earmarked for marketing?
  5. How does the company market or plan to market its products or services over the next 3, 6 and 12 months?
  6. What is the company’s PR strategy?
  7. What is the company’s social media strategy?
  8. What is your customer acquisition cost?
  9. What is the lifetime value of one of your customers?
  10. What advertising will you be doing?
  11. What is the typical sales cycle between initial customer contact and closing of a sale? How long? Who are the key players/decision-makers?


  1. How many early adopters/customers have you talked you?
  2. How many early adopters/customers have you visited?
  3. What early traction has the company gotten (sales, traffic to the company’s website, app downloads… etc., as relevant)?
  4. How can your early traction be accelerated?
  5. What has been the principal ‘driver’ for your early traction?
  6. What key metrics are you measuring for company growth?


  1. How do you keep someone from copying this immediately and selling it?
  2. What is the one thing that can kill your business… today, tomorrow, next week? And what is your strategy to defend against that risk?
  3. What do you see are the principal risks of your business?
  4. What do you see are the principal threats to your business?
  5. Who has the power, your suppliers or you?
  6. Who has the power, your customers or you?
  7. What legal risks do you have?
  8. What are the regulatory risks of your product/service/market/industry?
  9. Are there any product liability risks?
  10. What are your key assumptions?

Intellectual Property

  1. What is proprietary about your project?
  2. What key intellectual property does the company have (patents, patents pending, copyrights, trade secrets, trademarks, domain names)?
  3. What comfort do you have that the company’s intellectual property does not violate the rights of a third party?
  4. How was the company’s intellectual property developed?
  5. Would any prior employers of a team member have a potential claim to the company’s intellectual property? Why?


  1. What is my expected return on investment?
  2. What are the company’s three-year projections?
  3. What are the key assumptions underlying your projections?
  4. How much equity and debt has the company raised; what is the capital structure?
  5. What future equity or debt financing will be necessary?
  6. How much of a stock option pool is being set aside for employees?
  7. When will the company get to profitability?
  8. What is your burn-rate?
  9. How much runway are you currently working with?
  10. What are your unit economics?
  11. What are the factors that limit faster growth?
  12. What are the key metrics that the management team focuses on?

End Game

  1. What is your likely exit strategy — IPO or M&A?
  2. When do you see the exit happening?
  3. Who will be the likely acquirers?
  4. What price range do they typical make acquisitions?
  5. How will valuation of an exit be determined given market comparables?

Financing Round

  1. How much are you aiming to raise in this round?
  2. What is the company’s desired post-money valuation?
  3. What is your pre-money valuation?
  4. Will existing investors participate in the round?
  5. Who’s the lead investor?
  6. What is your proposed cap table?
  7. What is the planned use of funds from this round?
  8. What milestones will the financing get you to?
  9. When will you need more capital?

If you are planning to raise venture funding or begin your journey in entrepreneurship, being cognizant of these questions goes a long way when convincing others that you (1) know what you’re talking about, and (2) are worth putting their money behind — but that goes without saying. Because after-all, investors invest in people. Not ideas.

Danny J. Williams

Venture For Canada | Fellow
Halifax, Canada
t. +1.(902).880.0272