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Financial Mastery

The 50 questions investors ask about your numbers

Investor meetings are won and lost in the questions. For each one you get what the investor is really asking, a three-step way to answer, an example answer with real numbers from a sample company, and the mistake that loses trust.

Market & business modelRevenue & growthUnit economics & retentionCosts, burn & runwayThe raiseValuation, cap table & termsRisk, scenarios & the plan

Market & business model

  1. How big is the market, really?Really asking: Can this become a venture-scale company?
  2. Why will customers pay for this, and how much?Really asking: Is there real willingness to pay?
  3. How does the business make money at scale?Really asking: What do the unit economics look like when you're big?
  4. Who are your competitors and why do you win?Really asking: Do you understand the market, and is your edge durable?
  5. Why now?Really asking: What has changed that makes this the right moment?
  6. What's your business model in one sentence?Really asking: Can you explain it simply?

Revenue & growth

  1. Walk me through your revenue forecast.Really asking: Is the growth driven by real, controllable inputs?
  2. What's your current MRR and growth rate?Really asking: Do you know your numbers cold?
  3. Why will growth accelerate after this round?Really asking: What does the money change?
  4. How much of your revenue is recurring?Really asking: How predictable is your revenue?
  5. What is your sales cycle?Really asking: How long between spending and earning?
  6. What happens if your biggest channel stops working?Really asking: How concentrated is your growth?
  7. Is your year-3 forecast realistic?Really asking: Are you being honest or optimistic?
  8. What is your expansion revenue strategy?Really asking: Can existing customers grow?

Unit economics & retention

  1. What's your CAC, and how do you calculate it?Really asking: Do you include everything?
  2. What's your LTV : CAC?Really asking: Does each customer create value?
  3. What's your CAC payback period?Really asking: How much cash does growth tie up?
  4. What's your churn, and why do customers leave?Really asking: Is the product sticky?
  5. Show me your cohort retention.Really asking: Is retention improving over time?
  6. What's your net revenue retention?Really asking: Do existing customers grow?
  7. What's your gross margin, and what's in COGS?Really asking: Is this really a software business?
  8. How do your unit economics change at scale?Really asking: Will growth get more expensive?

Costs, burn & runway

  1. What's your monthly burn?Really asking: How fast are you spending?
  2. How much runway do you have?Really asking: How urgent is this raise?
  3. What's your burn multiple?Really asking: Is your growth capital-efficient?
  4. What's your biggest cost, and why?Really asking: Are you spending on the right things?
  5. When do you become profitable?Really asking: Can you survive without more funding?
  6. How do you plan hiring?Really asking: Is the team plan tied to the business plan?
  7. What would you cut if the raise takes longer?Really asking: Do you have a plan B?

The raise

  1. How much are you raising, and why that amount?Really asking: Is the round sized to a plan?
  2. How will you use the money?Really asking: Will the money create value?
  3. What milestones will this round get you to?Really asking: Will you be fundable next time?
  4. Who else is in the round?Really asking: Is there demand and a lead?
  5. When will you need to raise again?Really asking: How long does this money last?
  6. Have you raised money before?Really asking: What's already on the cap table?
  7. Why are you raising equity and not debt?Really asking: Do you understand your financing options?

Valuation, cap table & terms

  1. What valuation are you looking for?Really asking: Are your expectations realistic?
  2. What will founders own after this round?Really asking: Are founders still motivated?
  3. How big is your option pool, and is it enough?Really asking: Will we need to top it up (at our expense)?
  4. How do your SAFEs convert?Really asking: Any surprises in the cap table?
  5. What liquidation preference are you offering?Really asking: How are we protected in a downside?
  6. Do existing investors have pro-rata rights?Really asking: How much room is there in the next round?
  7. What does an exit look like for us?Really asking: Can this return the fund?

Risk, scenarios & the plan

  1. What are the biggest risks in your plan?Really asking: Are you self-aware?
  2. What's your downside case?Really asking: Will you survive if things go wrong?
  3. What assumption are you least confident about?Really asking: Will you be honest?
  4. How did you build this model?Really asking: Can we trust it?
  5. What have you learned that changed the plan?Really asking: Do you learn from data?
  6. What would make you miss your plan?Really asking: Do you know your sensitivities?
  7. How often will you report to us, and what?Really asking: Will you be a transparent partner?