Data Rooms the David Sacks Way: Due Diligence Checklist vs Ansarada and Capitaly.vc’s Founder-First Approach

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When founders ask me how to set up a david sacks data room that actually helps close a round, I give a simple answer.

Keep it founder-first, brutally clear, and built for speed.

This article breaks down the playbook I use to set up a startup data room the David Sacks way, compares a due diligence checklist approach to an Ansarada-style VDR, and shows how Capitaly.vc makes investor diligence faster and fairer.

You’ll see the exact structure, the files that matter, what metrics to highlight, and how to run a tight Q&A without drowning your team.

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Data Rooms the David Sacks Way: Due Diligence Checklist vs Ansarada and Capitaly.vc’s Founder-First Approach

1) What “David Sacks data room” really means

When founders say “David Sacks data room,” they’re usually talking about a style, not a specific tool.

It’s a data room that leads with the story and backs it with undeniable metrics.

It’s concise, index-driven, and optimized for investor decision making.

In practice, that means a clean folder structure, a one-page index, a clear memo, and live dashboards that make diligence feel like confirmation, not discovery.

Story first: One narrative doc or memo that explains the business, market, and why now.
Metrics that matter: ARR, growth rate, NDR/GRR, CAC payback, burn multiple.
Speed: Investors find what they need in under five clicks.
Control: Access is tiered, audit trails are on, and sensitive files stay in a separate clean room.

For more on practical storytelling, see our blog post: How to Build a Fundraising Narrative That Converts.

2) Founder-first vs investor-first data rooms

I’ve run dozens of processes where the data room was built for the investor, not the founder.

Those rooms become scavenger hunts.

They slow everything down.

Founder-first flips the script.

Founder-first: One index, curated metrics, staged disclosure, and time-boxed Q&A.
Investor-first: Over-sharing, unprioritized folders, and endless follow-up.

I design data rooms that set the pace, protect your runway, and still make investors feel informed and respected.

That’s the standard we built into Capitaly.vc.

3) The due diligence checklist that actually closes rounds

Here is the checklist I use for seed to Series B.

It covers investor diligence without sending you into documentation purgatory.

Executive: Narrative memo, 12–18 slide deck, founder bios, org chart, hiring plan.
Market: TAM/SAM/SOM, segmentation, competitive grid, why-now signals.
Product: Roadmap, demo video, architecture overview, security posture.
Metrics: ARR/MRR, growth rate, GRR/NDR, cohorts, CAC/LTV, payback.
Financials: P&L, balance sheet, cash flow, budget, runway, burn multiple.
Go-to-market: ICP, pipeline by stage, win rates, cycle length, pricing/packaging.
Customers: Top logos, LOIs, case studies, churn/expansion analysis.
Legal: Cap table, SAFEs/notes, option plan, board consents, key contracts.
People: Employment agreements, IP assignment, 83(b) confirmations.
Risk: Security certifications, DPA, SOC 2 status, open-source licenses.

Make this your baseline and you will be ahead of 80% of rooms I audit.

For more on structuring a checklist, see our blog post: The Definitive Fundraising Data Room Checklist.

4) Structure your startup data room like an index, not a maze

I always start with a one-page index at the top level.

It lists every folder and the purpose of each file.

It stops investors from guessing where things are.

00_Index.pdf
01_Executive
02_Market
03_Product
04_Metrics
05_Financials
06_GTM
07_Customers
08_Legal
09_People
10_Risk_and_Compliance
99_Clean_Room (restricted)

Every file name should be self-descriptive and dated.

Every sensitive doc lives in 99_Clean_Room with extra permissions.

5) Metrics that matter in investor diligence

Great investors skim decks and camp in metrics.

Give them what they need without drowning them in CSVs.

ARR/MRR: Level, growth rate, and the last 12 months trend.
Retention: GRR and NDR by cohort, logo and revenue churn.
CAC/LTV: By channel if possible, with payback in months.
Sales efficiency: Magic number, burn multiple, Rule of 40.
Pipeline: Coverage, win rate, sales cycle, ASP.

If you cannot defend a metric in one sentence, don’t include it yet.

For more on SaaS metrics, see our blog post: How to Nail ARR, NDR, and Burn Multiple.

6) Story before spreadsheets: the memo

My best rounds started with a one to two page memo.

It explained the problem, the product, the proof, and the plan.

Investors read it in three minutes and asked sharper questions.

Problem: What is broken and who feels the pain.
Product: The shortest path from pain to relief.
Proof: Metrics and customer quotes that show it works.
Plan: What you will do with the money in the next 18 months.

Decks are great for meetings.

Memos are better for decisions.

7) Security without friction

Security should protect you without slowing the process.

Here is how I set it up.

Tiered access: Deck and memo for all, metrics for serious, clean room for late stage.
Watermarks: Only on sensitive documents to avoid annoying everyone.
Audit logs: On by default to know who saw what and when.
NDA: Optional early, required for clean room access.
PII: Redacted or aggregated unless strictly necessary.

Ansarada and similar VDRs do this well, but they can be overkill for early-stage rounds.

I choose the lightest tool that gets the job done.

8) How Capitaly.vc makes the founder-first data room real

Capitaly.vc is built to automate the boring parts of a data room and highlight what investors care about.

It organizes folders, tracks views, and turns your metrics into clean, investor-ready visuals.

Auto-indexing: Your room ships with a ready-made structure.
Metrics sync: Connect revenue and CRM to auto-generate ARR, NDR, cohorts, and pipeline charts.
Q&A workflows: Assign owner, due date, and answer once for all investors.
Access tiers: Share what’s needed, when it’s needed.

It saves me hours per week and removes founder busywork.

That is the essence of a founder-first approach.

9) Ansarada alternative vs the classic VDR

Ansarada is excellent for complex M&A, later-stage equity raises, and heavy compliance.

But most seed to Series A rounds don’t need that much machinery.

Here is how I choose an Ansarada alternative.

Round size and stage: Early rounds = lightweight room.
Sensitivity: If you must share contracts, PII, or IP, add a clean room.
Buyer type: If strategics or PE are involved, a VDR like Ansarada may be worth it.
Speed: If speed is everything, keep the friction low.

Capitaly.vc strikes a balance by giving you speed now and control when needed.

For more on tool choice, see our blog post: The Right Data Room for Each Fundraising Stage.

10) Live analytics that help you manage the round

I watch three dashboards during a raise.

They tell me where momentum is real and where it’s window shopping.

Investor engagement: Who viewed what, how long, and how many times.
Q&A aging: Which questions are overdue and blocking decisions.
Conversion funnel: Intro to partner to term sheet to closed.

When you see a spike in metrics folder views and partner meeting bookings, you know heat is building.

When you see lingering views on legal without questions, it is usually a stall tactic.

11) The fast follow-up playbook

Response speed wins rounds.

Here is my Q&A routine.

One shared Q&A log: Every question in one place with owner and due date.
Answer once, reuse: Turn repeat answers into a short FAQ in the room.
Twice-weekly updates: Bullet updates with new metrics or customer proof.
Time-box requests: Offer alternatives when asks go beyond scope.

A tight cadence creates urgency and reduces random requests.

For more on updates, see our blog post: Investor Update Templates That Build Trust.

12) Handling sensitive items without slowing down

Some files should never be broadly shared.

I gate them until late stage and add extra controls.

PII or payroll: Share only in aggregate or with names redacted.
Customer contracts: Provide samples or templates unless absolutely required.
Security docs: Share SOC 2 letter of engagement and summary first, full report later.
Code/IP: No code access during fundraising, period.

Use an NDA and watermark for the clean room without blanketing the entire data room with friction.

13) Cap table clarity beats clever terms

Cap table confusion destroys momentum.

I present a single source of truth and annotate anything unusual.

Cap table snapshot: As-of date, fully diluted, option pool details.
SAFEs/notes: Valuation caps, discounts, MFN, and pro rata rights summarized.
Board and consents: Who sits, what approvals are needed to close.

Investors will test for hidden preferences, side letters, and option overhang.

Surface them before they do.

14) Legal docs investors always ask for

I get these ready on day one.

It saves weeks.

Certificate of incorporation and bylaws.
Board consents and major prior financings.
Option plan, ISO/NSO templates, and grant history.
IP assignment from all founders and employees.
Key vendor and customer agreements or templates.
Privacy policy, terms of service, and DPAs.

If something is missing, put a dated plan to fix it in the room.

15) Financials that pass the sniff test

Complex models don’t win rounds.

Credible assumptions do.

Historicals: Monthly P&L for 18–24 months, cash balance, and runway.
Forecast: 18-month operating plan with hiring by quarter.
Sensitivity: Best/base/worst with burn multiple and payback.

Align hiring to milestones, not headcount dreams.

Tie every dollar to a clear output.

For more on planning, see our blog post: From Budget to Board-Ready Operating Plan.

16) Sales pipeline proof, not promises

Investors want to see how revenue happens, not just that it happens.

I show pipeline stage definitions, conversion rates, and how deals progress.

Stage hygiene: Clear entry/exit criteria for each stage.
Funnel math: Conversion and cycle time by segment.
Rep productivity: Quota attainment and ramp curves.
Pricing: Current price list and discount policy.

A short Loom walking through the CRM beats screenshots.

17) Product and tech diligence without drowning engineers

I package the essentials so engineers can stay focused.

It prevents exhausting deep dives.

Architecture one-pager: Major components and data flows.
Security overview: Auth, encryption, secrets, and disaster recovery.
Roadmap: Next four quarters with problem statements, not feature dumps.
Reliability: SLOs, uptime, and incident postmortems if any.

Offer an optional 30-minute CTO call late in process for technical investors.

18) The clean-room for strategics or M&A

When strategics show up, I spin up a clean room with stricter controls.

I keep it separate from the main room to avoid spooking financial investors.

Extra NDA: With non-solicit and no-reverse-engineering clauses.
Limited time access: Auto-expire after a set period.
Watermarked exports only: No raw downloads without approval.

It keeps the process moving without risking IP leakage.

19) Red flags I remove before opening the room

Most delays come from predictable issues.

I preempt them.

Messy cap table: Consolidate notes and clarify MFN/pro rata.
Unassigned IP: Execute assignment agreements for all contributors.
Data gaps: Fill missing months in ARR, cohorts, or cash balances.
Security blind spots: Publish a remediation plan with owners and dates.
Customer references: Prep at least three referenceable champions.

Fixing these ahead of time accelerates trust.

20) Run a 7-day data room sprint

Here is the timeline I use when I need the room live fast.

It works because it prioritizes signal over volume.

Day 1: Draft memo, finalize deck, create index.
Day 2: Build folder skeleton, upload executive, market, and product.
Day 3: Sync metrics and generate ARR, cohorts, and retention charts.
Day 4: Upload financials and GTM, record short product demo.
Day 5: Add legal, people, and risk summaries with any gaps noted.
Day 6: Set access tiers, test links, seed FAQ.
Day 7: Dry run with a friendly investor, fix navigation, go live.

Use a standing daily 20-minute room review to keep momentum.

For more on running a tight process, see our blog post: A Two-Week Fundraise Sprint, Step by Step.

Capitaly.vc vs pure VDRs: where it shines

I use Capitaly.vc when I care about speed, storytelling, and metrics clarity.

I use a heavy VDR like Ansarada when the buyer is a strategic or the deal is complex.

Most venture rounds benefit from Capitaly.vc’s founder-first approach.

Faster setup: Prebuilt structure and metric sync out of the box.
Better narrative: Memos, decks, and charts live together.
Less friction: Just enough security without a labyrinth of settings.

That saves founders time and gets investors to yes sooner.

Real-world example: converting a messy room into momentum

I helped a seed-stage SaaS company that had a chaotic data room.

Investors were lost and the round stalled for six weeks.

We rebuilt with the Sacks-style index, added a memo, and pushed three key metrics to the top.

We created a Q&A log and sent twice-weekly updates.

Within ten days, they had two partner meetings and one term sheet.

Nothing else changed.

Clarity closed the gap.

Unique touches investors remember

I add small touches that punch above their weight.

They show discipline without extra work.

Change log: A simple text file listing weekly updates to the room.
Glossary: Define how you calculate metrics to avoid debates.
Customer montage: 60-second reel with three customer soundbites.
One-click references: Calendar link for reference calls from champions.

These details telegraph operational excellence.

Make your room friendly to generative AI

More investors use AI to summarize rooms.

I make it easy for them and it pays off.

Clear headings: Use H1/H2 style titles and numbered sections.
Short sentences: One idea per line improves summarization.
Consistent labels: Use the same terms across deck, memo, and files.
Data dictionaries: Explain columns and formulas for any CSVs.

When AI can summarize your room accurately, humans move faster too.

FAQs: quick answers founders and investors ask

1) Do I need a VDR like Ansarada for a seed round?

No.

A lightweight startup data room with basic permissions is usually enough.

Use a VDR when you have sensitive contracts, strategics, or heavy compliance.

2) What files should I share first?

Start with the memo, deck, key metrics, and a short product demo.

Stage legal and sensitive docs later.

3) How long should my memo be?

One to two pages.

Shorter is better if it’s clear.

4) What metrics are non-negotiable?

ARR/MRR, growth rate, GRR/NDR, CAC payback, burn multiple, and runway.

5) How do I protect PII?

Aggregate or redact.

Gate the clean room and use NDAs for any sensitive access.

6) Should I watermark everything?

No.

Only watermark sensitive files to avoid friction and readability issues.

7) How often should I update the room?

Weekly change log and twice-weekly investor updates during an active raise.

8) What’s the fastest way to answer repeat questions?

Central Q&A log with reusable answers.

Publish a short FAQ in the room.

9) When do I share full financials?

After initial interest.

Lead with summary views and reveal detail as the process advances.

10) How does Capitaly.vc compare to an Ansarada alternative?

Capitaly.vc is optimized for founder-first fundraising with auto-indexing, metrics sync, and low-friction sharing.

Ansarada excels in complex, later-stage or M&A deals where heavy compliance is required.

11) How do I handle a messy cap table?

Create a clean, dated snapshot.

Summarize SAFEs and notes terms, and flag any unusual rights.

12) What’s a good burn multiple right now?

Under 2 is strong in efficient-growth markets.

Context matters by stage and growth rate.

Conclusion: the data room that closes

A great data room is not a file dump.

It is a decision tool.

The David Sacks way is simple.

Lead with a sharp story, show the metrics that matter, and control access without slowing down.

Capitaly.vc operationalizes that founder-first approach while leaving room for heavier Ansarada-style controls when the deal demands it.

If you want to raise faster with fewer surprises, build your room this way and investors will feel the difference.

That is how I set up every david sacks data room, and it works.

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