40+ VC Questions for AI × Crypto Startups

How to use this:

• Founders: prepare written answers to all of these before your first meeting. If you can't answer one, that's a gap to fix before pitching.
• VCs: use as a structured interview framework. The quality of answers reveals founder depth more than the deck.

Category 1: Team & founder fit

1. Why are you the team to solve this problem? What insight do you have that others don't?
2. Walk me through your co-founder story. How did you meet? What's the equity split and why?
3. What's the hardest thing you've built before? What happened to it?
4. If this doesn't work, what's the most likely reason it fails — and what are you doing about it?
5. Who on your team has done this before? At what scale?
6. What's a significant mistake you made in a previous venture? What did you learn?
7. Who is NOT on your team that you need in the next 12 months?
8. What happens if your CTO/CPO leaves tomorrow?

What VCs want: self-awareness, complementary skills, realistic assessment of gaps, founder-market fit.

Category 2: Product & technology

9. Show me the product. Walk me through one user workflow end to end.
10. What's the hardest technical problem you've solved? How?
11. What does your architecture look like? Where are the bottlenecks at 10x scale?
12. What can you do that a well-funded competitor with 50 engineers couldn't replicate in 6 months?
13. What's your approach to smart contract security? Have you been audited?
14. How do you handle the thing that will go wrong (oracle failure / bridge exploit / key management)?
15. What open-source components are you building on? What's your IP vs. assembled?

AI × Crypto specific:

16. What model are you using? What happens when a better model releases? Is your moat model-dependent?
17. For AI agents: what does your agent do in an ambiguous situation? Who has override?
18. For DePIN: what's the incentive for hardware providers to stay vs. switch to a competitor?
19. What's your on-chain footprint? Show me the contract addresses and activity.

Category 3: Market & timing

20. What's happening in the market that makes this fundable today but not 2 years ago?
21. Who are your first 100 customers / protocols / validators? Name them.
22. What's the size of the market you're actually going after in 18 months — not the TAM?
23. What's your go-to-market motion, step by step?
24. Who are your top 2 competitors? What do they do better than you right now?
25. What do customers do today without your product? Why hasn't anyone solved this?

Category 4: Traction & metrics

26. Show me your retention curve. What's D30 retention?
27. What does your best customer look like? Walk me through their journey to paying.
28. What's your CAC? Payback period? LTV?
29. What's your MoM growth over the last 6 months? Why the spike or dip?
30. How much revenue did you generate last month? This quarter?
31. What's the biggest channel driving growth? Is it defensible?

Crypto-specific:

32. Daily active wallets over 90 days — show me the chart.
33. Protocol fee revenue vs. token incentives — what % of activity is organic?
34. What's your TVL, and how much leaves if you remove the yield incentive?

Category 5: Tokenomics & economics (if applicable)

35. What does your token do? Why does the protocol need one?
36. What creates organic buy pressure? What creates sell pressure?
37. Walk me through the vesting schedule. When can the team sell?
38. What % of supply is controlled by team + early investors combined?
39. If your token goes to zero, does the protocol still work?
40. How do you prevent a death spiral (token drops → incentives collapse → users leave → token drops)?
41. What's your treasury strategy? How many months of runway?

Category 6: Business & fundraising

42. What are you raising? What does this capital get you to specifically?
43. What milestone unlocks your next round? What does Series A require?
44. Who else are you talking to? What's your timeline to close?
45. What would change your mind about this company? What's the bear case?
46. How are you thinking about legal structure, especially token / regulatory exposure?
47. What does success look like in 3 years? In 7 years?

The hardest questions

VCs ask these to see how founders think under pressure:

48. "Your biggest competitor just raised $50M from Paradigm. What do you do?"
49. "You're 6 months from running out of money: raise a down round at 50% discount, or sell to a strategic for 2x your last valuation. Which, and why?"
50. "If you couldn't raise this round, what would you do to make this work anyway?"
51. "What's the one thing you're most uncertain about in this business right now?"

Lookout Library · updated 2026-05-28 · not financial advice