VC Due Diligence Checklist: 50 Questions Every Investor Should Ask

Every experienced VC has a story about the deal that looked perfect — until it wasn't. The metrics were real but unsustainable. The founder was brilliant but had a fraud conviction. The market was huge but already won.

A structured VC due diligence checklist prevents these surprises. It forces you to ask the right questions before the wire transfer, not after.

Here are 50 questions organized by category. Not every question applies to every deal, but skipping a category entirely is how mistakes happen.

Team & Founders (Questions 1-10)

1. What is each founder's professional background, and can it be independently verified? Don't rely on LinkedIn alone. Check references, confirm employment dates, verify degrees.

1. Have the founders worked together before? First-time co-founder relationships are the #1 startup killer. Prior working history is a strong signal.

1. What happened to the founders' previous companies? Shutdowns aren't disqualifying, but patterns matter. Three failed ventures with co-founder disputes is a pattern.

1. Do any founders have legal issues — lawsuits, bankruptcies, regulatory actions? Run background checks. Check PACER and state court records.

1. Is there a vesting schedule for all founders? If a founder can walk away with 40% of the company tomorrow, that's a structural risk.

1. How do the founders handle disagreement? Ask each founder separately. Inconsistent answers are informative.

1. What's the founders' personal financial situation? Founders under severe personal financial pressure make different decisions.

1. Who's the CEO, and is that clear to everyone? Ambiguous leadership structures kill companies.

1. How deep is the technical talent? Is the CTO building or managing? "Technical co-founder" can mean anything from ML PhD to WordPress developer.

1. What key hires are needed in the next 12 months, and can they attract that talent?

Market (Questions 11-20)

1. What is the total addressable market, and how was it calculated? Rebuild their TAM estimate independently. Top-down vs. bottom-up numbers should be within 2x of each other.

1. Is the market growing, stable, or contracting? Use third-party data, not the pitch deck.

1. What are the major market trends driving demand? Is this a durable shift or a hype cycle?

1. Who are the top 5 competitors, and what's each one's market share?

1. What's happened to companies that previously tried to solve this problem? If the graveyard is full, understand why this attempt is different.

1. Are there regulatory changes that could help or hurt this market?

1. How do potential customers currently solve this problem? The real competitor is often "do nothing" or "use spreadsheets."

1. Have you spoken directly to 5+ potential customers? What did they say?

1. What's the customer switching cost? How easy is it to leave?

1. Is this a winner-take-all market or a fragmented one?

Product & Technology (Questions 21-30)

1. Can you demo the product? Does it work as described?

1. What's the core technology, and is it defensible? Patents, proprietary data, network effects, or switching costs?

1. If this is an AI product: what's proprietary vs. built on third-party models? A GPT wrapper is not a technology company.

1. What's the product roadmap for the next 12 months?

1. What's the biggest technical risk? If the founders say "none," that's a red flag.

1. How long would it take a well-funded competitor to replicate this?

1. What do users actually say about the product? (Check reviews, NPS, support tickets)

1. What's the deployment model? (SaaS, on-prem, API, hybrid)

1. Is there technical debt that could slow development?

1. What third-party dependencies exist? (AWS, Stripe, specific data providers)

Financials & Unit Economics (Questions 31-40)

1. What is current MRR/ARR? Verify with bank statements.

1. What's the month-over-month growth rate for the last 12 months? Average growth hides volatility. Look at the curve.

1. What's the gross margin?

1. What's the CAC, and how is it calculated? Include all marketing and sales costs, not just ad spend.

1. What's the LTV, and what assumptions drive it? LTV based on 3 months of data is a guess, not a metric.

1. What's the burn rate and current runway?

1. What are the major cost drivers, and how do they scale?

1. What's the revenue concentration? (Top customer as % of revenue) If one customer is >25% of revenue, that's a risk.

1. What's the churn rate — logo churn and revenue churn? Net revenue retention >100% is the gold standard.

1. What are the payment terms? (Upfront, monthly, annual, net-30/60/90)

Legal & Structure (Questions 41-46)

1. What's the corporate structure? (C-corp, LLC, jurisdiction)

1. What's on the cap table, and are there any unusual terms? Liquidation preferences, anti-dilution clauses, side letters.

1. Does the company own all its IP? Are there clean assignment agreements?

1. Are there any pending or threatened lawsuits?

1. Is the company compliant with relevant regulations? (GDPR, SOC2, HIPAA, etc.)

1. Are there any outstanding debts, convertible notes, or SAFEs we need to understand?

Deal-Specific (Questions 47-50)

1. What's the proposed valuation, and how does it compare to recent comparable rounds?

1. Who else is in this round? Have you spoken to them? Co-investors doing their own diligence is a positive signal.

1. What does the company need to achieve before the next round? If the milestones seem unrealistic, the bridge round is already priced in.

1. What's your exit thesis? Who acquires this company or takes it public, and on what timeline?

Using This Checklist

Don't try to answer all 50 questions for every deal. Prioritize based on stage:

• Pre-seed/Seed: Focus on Team (1-10) and Market (11-20). Product and financials are too early to evaluate rigorously.
• Series A: All categories matter. Product-market fit should be demonstrable.
• Series B+: Financials and unit economics (31-40) become critical. The story should be backed by numbers.

Speed up your due diligence: Services like IntelReport can generate a comprehensive company intelligence report covering many of these questions in hours. Use it as your research baseline, then go deeper on the areas that matter most for your specific deal.

Related reading:

• How to Do Due Diligence on a Startup in 2026
• Company Intelligence Reports: What They Are and Why You Need One