February 2025

Market & Competition

1. Describe your Ideal Customer Profile? What pain points make them ideal for your solution?

2. How did you validate that your ICP exists in sufficient numbers to support your growth plans?

3. You mentioned your SAM is $X. What specific segment are you targeting first, and why did you choose that entry point?

4. Which competitors worry you the most, and what prevents them from copying your approach?

5. What are the top 3 obstacles to customer adoption, and how are you addressing them?

6. How has the market changed in the last 12 months, and how might it evolve in the next 24?

7. How quickly do you feel you need to scale given the market and competition? How do you intend to do so?

Business Model & Unit Economics

1. Walk us through the unit economics of a typical customer acquisition and lifetime value?

2. at what scale does your business model become profitable? What are the key assumptions?

3. How do you plan to reduce customer acquisition costs over time?

4. What’s your pricing strategy, and how did you validate that customers will pay these amounts?

5. Are there network effects or economies of scale in your model?

Traction & Metrics

1. Of your current users/customers, what percentage match your ICP, and how do they compare to non-ICP customers in terms of retention and revenue?

2. Of your current users/customers, what percentage are actively engaged with your product? How many are paying vs non paying?

3. What’s your monthly burn rate, and how long will your current/requested funding last?

4. Which metrics do you believe best indicate future success for your business?

5. What’s been your biggest go-to-market surprise or learning so far?

6. What percentage of your growth is organic vs. paid?

Team & Execution

1. What makes your team uniquely qualified to solve this problem?

2. What key hires do you need to make in the next 12 months?

3. How do you plan to build and maintain your company culture as you scale?

4. What keeps you up at night about the business?

5. Have you or other members of the founding team personally invested money into the business?

6. What key execution risks could derail your next 12 months?

Technology & Product

1. What are the biggest technical risks in your roadmap?

2. How defensible is your technology/solution? What’s your IP strategy?

3. How do you prioritize your product roadmap? What’s been left out and why?

4. What’s your backup plan if key technical assumptions prove incorrect?

Market Timing & External Factors

1. Why is now the right time for this solution?

2. How dependent is your success on external factors (regulation, technology adoption, etc.)?

3. How would an economic downturn affect your business and growth plans?

4. What industry trends are you betting on or betting against?

Exit Strategy & Return Potential

1. What are exit paths for this business? Can you give examples of similar exits in your space?

2. What are the typical revenue multiples for acquisitions in your industry? How do you see those applying to your business?

3. Given your current valuation and the investment needed to reach exit, what size of exit would you need to generate venture-scale returns?

4. How do you see your business fitting into the strategy of potential acquirers? Who are they?

5. What metrics or milestones do you think would make you attractive for an IPO or acquisition?

6. How do you balance building for sustainable growth versus positioning for an exit?”

7. What’s your perspective on the venture model and the need for outlier returns to drive portfolio economics?

Use of Funds & Growth Strategy

1. How specifically will you use the funds you’re raising?

2. What key milestones will this funding help you achieve?

3. What’s your fundraising strategy beyond this round?

4. How do you plan to scale your team and operations with the funding?

5. Have you raised before? If so when, from who, and at what valuation?

Follow-up Questions for Common Responses

1. If suggest modest exit multiples: How would that exit value translate to returns for early investors given the likely dilution path?

2. Haven’t researched exits: Which recent exits have you studied? What made them successful?

3. If focus is only on acquisition: What would it take to build this into a standalone public company?

Red Flag Responses to Watch For

1. If they deflect on competition: Which existing solutions do your target customers use today? How do they serve your ICP specifically?

2. If no competition matrix: Could you map out your key competitors on a feature/capability matrix?

3. If traction seems low: What gives you confidence in your product-market fit?

4. If team seems incomplete: How are you handling [key missing function] currently?

5. If financials are vague: Can you share your current gross margins and how they might evolve?