25 Shaan Puri Due Diligence Questions and How to Answer Them with Your Data Room

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Let's get real about Shaan Puri due diligence. If you're raising a round, chances are you'll face a version of Shaan Puri's famous investor questions at some point. Founders nervously prepping the "perfect" data room always ask, "What documents do VCs actually care about?" or "How deep will the questions go?" This guide has you covered.

Below, I break down 25 classic Shaan Puri-inspired due diligence questions and show—in plain English—how to address them using your data room. I share tips on what to include, what metrics matter, and why assembling these materials is your unfair advantage. I even compare data room solutions—why you might want an Ansarada alternative like what we use at Capitaly.vc.

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If you want to turn fundraising diligence from a landmine into a landslide, start here. Let's dive in.

1. What Problem Are You Solving?

Investors need to know you’re solving a real pain, not a "nice-to-have." Be blunt. Use your pitch deck (slides 1–3) and a simple one-pager in the data room.
Checklist:

• Problem statement (1-3 sentences)
• Market stats or user quotes that prove urgency

Back up your claim with feedback, reviews, or pain-point research.

2. Who Are Your Customers?

Your sales pipeline and CRM exports are gold here. VCs want real names—not just "SMBs in the US."
Your answers:

• Customer list (with segments or key accounts anonymized if needed)
• Pipeline report/export
• User personas

Show target customers and current paying users. For a deep dive on audience definition, see our blog post: Building Your Ideal Customer Profile.

3. What’s Your Traction So Far?

VCs want proof, not potential. Drop these into your data room:
Metrics to include:

• MRR/ARR charts (monthly recurring revenue)
• Growth graphs (users, revenues, etc.)
• Milestone tracker

Screenshots from analytics/Dashboard tools help make traction real.

4. How Large Is Your Market?

Be specific on TAM (Total Addressable Market), SAM (Serviceable), and SOM (Obtainable).
Documents:

• Market sizing PDF/Excel
• Citations from analyst reports

Don't over-inflate—show how you get your estimates.

5. Who Are Your Competitors?

Don’t claim you have none. Instead, provide a competitor matrix.
Checklist:

• 2x2 grid of main competitors
• Feature comparison table
• Competitive advantages summary

Show why you’re meaningfully different.

6. How Do You Make Money?

Include your revenue model and current pricing. Founders often hide details—they shouldn’t.
In your data room:

• Pricing sheet or page (current & historical)
• Sample invoices
• Revenue breakdown by product/service

Be transparent; uncertainty kills investor trust.

7. What’s Your Go-to-Market Plan?

VCs want a pipeline plan, not just "We’ll do social ads."
Data room docs:

• Go-to-market one-pager or slide deck
• Sales funnel diagram
• Customer acquisition cost (CAC) worksheet

Show concrete channels—and backing data if possible.

8. Who’s On Your Team?

Shaan Puri and other VCs will look at bios AND cap table.
Your answer:

• Team bios (with photos and LinkedIn IDs)
• Org chart (if >8 people)
• Cap table summary (use a clean spreadsheet!)

Highlight advisors as well as core hires.

9. Show Us Your Financials

This is where many data rooms fall apart.
Must-have docs:

• Historical P&L (profit and loss) statements – 2–3 years if available
• YTD actuals
• Forecast/projections (at least 18–24 months forward)

Numbers beat any story. Include both PDF exports and original Excel files for credibility.

10. What Are Your Key Metrics?

Don't just share what’s working. Investors want both strengths and weaknesses.
Metrics to highlight:

• Churn/Retention rates
• LTV:CAC ratio
• Sales cycle length
• DAUs/MAUs (active users)

Add a "KPI definitions" page so everyone uses the same terms. For more on SaaS metrics, see our blog post: SaaS Metrics for Fundraising.

11. How Will You Use the Capital?

Don’t just say “growth.” Spell out use of funds in detail.
What to include:

• Use of proceeds slide (show % allocation)
• Hiring/expansion plan

Share budget breakdowns for major spending items.

12. What Are the Biggest Risks?

Honesty stands out. Identify risks and your battle plan.

• Risk list (top 3–5)
• Mitigation strategies doc or SWOT

Don't hide risks; VCs will sniff them out.

13. Share Legal Docs & Structure

No one wants legal surprises after a term sheet.
Your data room checklist:

• Certificate of incorporation
• Founders’ agreements
• IP assignments and patents (if any)

Add signed NDAs and any prior SAFE/convertible agreements, too.

14. What’s Your Exit Strategy?

Exit is top-of-mind for VCs. Share past M&A activity and sample hypothetical scenarios.
Documents to upload:

• Prior acquisition approaches (if any)
• Industry exit comps (valuation multiples, recent deals)

This builds confidence that your company fits their "return profile."

15. Show Customer Contracts & Deal Flow

Show sample contracts to prove quality of deals.
Checklist:

• Sample or redacted customer contracts/LOIs
• Pipeline/closed-won report

This shows confidence in your sales process and legal clarity.

16. Who Are Your Advisors and Why?

Document the value advisors bring.
In your data room:

• Advisor bios (brief, 1 paragraph)
• Letters of engagement or equity agreements

Highlight specific, relevant experience.

17. Show Us Product Roadmap and Tech Stack

Don’t just talk feature wishlists.
Data room items:

• Roadmap slides or Notion/Jira exports
• Diagram of tech architecture

Show what’s built, in progress, and on deck. For roadmap best practices, see Roadmap Metrics.

18. Prove Regulatory Compliance

This applies to fintech, health, and international startups especially.

• Compliance certificates (GDPR, HIPAA, SOC2...)
• Licensing docs

Make sure investors see your "clean bill of health."

19. What Makes Your Moat Defensible?

Go beyond buzzwords. Address this in both narrative and supporting materials:

• IP filings, proprietary datasets
• Network effects/data network documents
• User retention graphs

Your moat must be more than just “first-mover advantage.”

20. What External Validation Have You Earned?

Investors trust third parties.

• Press, awards, notable reference customers
• Testimonials and NPS scores

Include these as a "validation" folder and reference in your deck.

21. What Is Your Data Room Checklist?

This is your data room’s index—the table of contents for everything above. For a deeper template, see our blog post: Fundraising Data Room Checklist.

22. Why Not Use Ansarada? (Choosing an Alternative)

Ansarada is popular, but many look for an Ansarada alternative due to price, UX, or privacy. At Capitaly.vc, we recommend solutions like Google Drive (with the right security), CapTable.io, or DealRoom—customized for fundraising, not M&A.
Key factors:

• User permissions granularity
• Collaboration features
• Audit logs

Choose a tool the team can actually use fast.

23. How To Keep Your Data Room Updated

Don’t "set and forget." Set a reminder (monthly or quarterly) to sync fresh KPIs, contracts, and milestones. Use checklists and version history for transparency. For ongoing readiness tips, see Continuous Fundraising.

24. Can You Tell a Story with Your Numbers?

The best founders weave narrative and data. Every folder (financial, customer, legal) should reinforce your core story: what makes you investable.
Tips:

• Start every section with a one-paragraph summary
• Highlight "aha" moments in the data

Numbers prove your gut feeling. Make it easy for VCs to connect the dots.

25. How Quickly Can You Respond to Investor Requests?

Speed builds confidence. Answering Shaan Puri due diligence questions quickly—often within 24–48 hours—shows operational excellence. Keep hot docs prepped, key metrics at hand, and "who owns what" clarified in your core team. Speed matters as much as content.

FAQs: Shaan Puri Due Diligence and Data Rooms

• What is Shaan Puri's approach to due diligence?
  He focuses on practical, direct questions—cutting through hype and pushing for real, relevant proof.
• How do I structure my data room for investors?
  Use clear folders by topic: Financial, Legal, Customers, Product, HR, and Metrics—with a top-level checklist file.
• What if I can’t answer a key investor question?
  Be honest. Flag it in your data room as "in progress" and provide an estimated update date.
• How secure should my data room be?
  Use tools with permission controls, audit logs, and watermarks. Never compromise on privacy.
• What docs are essential for early-stage due diligence?
  Pitch deck, financials, cap table, customer contracts, product roadmap, legal formation, and key metrics summary.
• Is it bad to update my data room during the process?
  No. In fact, adding updates with timestamps shows your momentum and transparency.
• Do I have to upload every single contract?
  No. Redact or summarize for major contracts; keep sensitive deals on record for final stages.
• What does Capitaly.vc recommend for data room platforms?
  Google Drive (with strong permissions), CapTable.io, or DealRoom—fast, secure, founder-friendly alternatives.
• How long does fundraising due diligence take?
  It can be as fast as 1–2 weeks with a ready data room, or drag on for months if unorganized.
• What mistakes kill deals in due diligence?
  Missing or inconsistent numbers, legal issues, slow responses, or hiding major risks.

Conclusion

Mastering Shaan Puri due diligence questions is about being prepared, open, and brutally clear. With the right data room—your own or an Ansarada alternative—you’ll look pro, win VC trust, and accelerate your fundraising. For more winning strategies and templates, subscribe to Capitaly.vc Substack (https://capitaly.substack.com/) to raise capital at the speed of AI.