Introduction

Founders often spend weeks perfecting their pitch deck, rehearsing their story, and answering every possible investor question. But when a term sheet finally arrives, many fail to do one critical thing: ask hard questions back.

The right VC brings more than capital — they bring insights, support, and long-term thinking. The wrong one can slow you down, interfere with your team, or disappear when things get tough.

This guide offers 65 questions founders should ask VCs before accepting funding. They’re practical, direct, and designed to help you evaluate fit across 9 key areas. Not all questions will apply — but the right ones will give you insight most founders miss.

We cover:

1. Fund & Firm Fit
2. Support & Value-Add
3. Financial & Investment Terms
4. Term Sheet Process & Timing
5. Governance & Control
6. Team & Founder Fit
7. Diligence & Risk
8. Culture & Reputation
9. Exit & Future Planning

Let’s dive in.

1. Fund & Firm Fit

1. Do you lead deals, or prefer to follow?
2. What % of your fund does this investment represent?
3. Do you reserve capital for follow-ons? If so, how much?
4. What’s your average follow-on behavior — how often and under what criteria?
5. How aligned is your investment thesis with our space?
6. Why are you investing in us specifically?
7. What’s your typical fund lifecycle and exit horizon?
8. What % of your seed investments reach Series A?
9. What’s your fund’s overall return or win rate?

2. Support & Value‑Add

1. What support do you provide beyond capital?
2. Do you help with recruiting, GTM, or strategic planning?
3. How do you allocate time across your portfolio?
4. Can you share references from founders you’ve backed — including ones that didn’t work out?
5. Will I work directly with a partner? Who will be my main contact?
6. Do you offer bridge financing between rounds?
7. How do you handle tough situations — like pivots or missed milestones?

3. Financial & Investment Terms

1. What valuation and cap table assumptions are you working with?
2. Who absorbs the option pool dilution?
3. What control terms do you typically require (board seats, voting rights)?
4. What liquidation preference is standard for your deals?
5. Are there any anti-dilution or downside protections I should know about?
6. Are there performance or milestone-based clauses?
7. What impact will this round have on founder ownership?
8. What are your expectations around founder vesting?

4. Term Sheet Process & Timing

1. Who makes the final investment decision?
2. What’s your typical timeline from the first meeting to the signed term sheet?
3. How long does it usually take to wire funds after closing?
4. Do you include no-shop or exclusivity clauses?
5. What happens if there are delays in closing or capital call issues?
6. Have you already closed your fund and secured LP commitments?

5. Governance & Control

1. Will you request a board seat? What do you expect from board participation?
2. What rights or vetoes do you require for major decisions?
3. How involved are you in executive hires or firings?
4. How often do you expect board meetings and reporting?
5. How do you handle disagreements with founders?

6. Team & Founder Fit

1. What attracted you to our founding team?
2. How do you assess founder coachability and long-term potential?
3. Have you ever replaced a founder? Under what circumstances?
4. How involved are you in helping founders hire senior roles?
5. What’s your reputation among founders you've backed?

7. Diligence & Risk

1. Are you satisfied with our current data room and materials?
2. What are the top 2–3 things you're still uncertain about?
3. What’s your diligence process — legal, financial, or IP?
4. Do you perform founder background checks?
5. What happens if we materially miss projections after signing?
6. Do you require any post-close governance or milestone conditions?

8. Culture & Reputation

1. What are your firm’s values and decision-making style?
2. How often do you engage with founders after funding?
3. How do you handle internal competition between portfolio companies?
4. Can you name one portfolio founder who would not recommend you, and why?
5. What feedback have you heard from other founders about your firm?
6. How do you rank or prioritize portfolio companies internally?

9. Exit & Future Planning

1. What’s your ideal exit timeline?
2. What kind of exit paths do you typically support (acquisition, IPO, secondary)?
3. How hands-on are you in M&A or exit prep?
4. Do you expect to participate in future rounds?
5. What happens if the company fails or changes direction significantly?
6. How do you help preserve optionality (pivots, spinouts, acqui-hires)?
7. Have you helped drive exits? Can you give an example?

10. Founder's Filter (Final 6 Power Questions)

1. What happens when things go wrong? How do you show up?
2. How do you define a successful founder-VC relationship?
3. What’s one mistake you’ve made with a portfolio company — and what did you learn?
4. If we disagree, how do you usually approach conflict?
5. What kind of founder would you not invest in again?
6. What’s your long-term ambition as a firm — and where do we fit into that?

Conclusion

Taking VC money is a multi-year decision.

The moment you bring an investor onto your cap table, you're starting a long-term relationship. They’ll be in your board meetings, in your email threads, and — when things get hard — in your decisions. That makes fit more important than valuation, and alignment more valuable than speed.

These 65 questions are designed to give you clarity

1. Clarity on how your investor works.
2. Clarity on what they expect.
3. Clarity on what support you’ll actually get.

Some VCs will answer with honesty and specifics — others won’t. And that’s exactly the point. How they respond tells you everything about what it’ll be like to build with them for the next 3, 5, even 10 years.

Don’t hesitate to ask the hard stuff. You’re not just raising a round — you’re choosing a partner.

Capital is replaceable. Your company isn’t. Choose wisely.

Good luck 🙂