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Data-room guide
A data room isn't a dumping ground for files — it's the mirror image of the diligence checklist. Every folder answers a specific question the other side is going to ask, and a room that's organized to match the way counsel reads it closes faster and re-prices less. This is the folder tree, generalized from an exchange-listing-grade room and trimmed to exactly what each fundraising stage needs.
| Folder | Diligence question it answers | Key files |
|---|---|---|
| 01_Corporate | Does the entity exist cleanly? | COI + amendments, bylaws, good-standing cert, EIN letter |
| 02_Cap_Table | Is the ownership real and reconciled? | FD cap table (xlsx), share ledger, board consents, option grant register, current 409A |
| 03_Convertibles | What does my SAFE stack convert to? | Each executed SAFE/note, side letters, SAFE_terms_summary.pdf (cap/discount/MFN/pro-rata per holder) |
| 04_IP | Do you own your product? | Signed IP assignments (all contributors), founder prior-employer reps, OSS/SBOM license inventory, IP schedule |
| 05_Financials | Do the numbers reconcile? | Monthly P&L + cash (12+ mo), bank reconciliations, filed tax returns, liability schedule |
| 06_Revenue_Metrics | Is the traction defensible? | Revenue-recognition policy, bookings-to-revenue recon, read-only system metric export |
| 07_Contracts | Does anything break on the deal? | Top-N customer contracts, vendor commitments, CoC_assignment_flags.pdf, license register |
| 08_Team | What walks out the door? | Founder stock purchase agreements + vesting + 83(b) evidence, employment/contractor agreements + classification rationale |
| 09_Legal_Compliance | Any undisclosed exposure? | Litigation schedule or clean rep, demand letters, privacy policy + DPAs, permit register |
Building all nine folders for a pre-seed round is over-engineering — and an empty folder reads worse than no folder. Build only what your stage's investors actually open:
| Folder | Pre-seed | Seed | Series A | Series B / Acq |
|---|---|---|---|---|
| 01 Corporate | ✓ | ✓ | ✓ | ✓ |
| 02 Cap Table | ✓ | ✓ | ✓ | ✓ |
| 03 Convertibles | if any | ✓ | ✓ | ✓ |
| 04 IP | ✓ | ✓ | ✓ | ✓ |
| 05 Financials | light | basic | ✓ | ✓ |
| 06 Revenue Metrics | n/a | if revenue | ✓ | ✓ |
| 07 Contracts | n/a | top few | ✓ | ✓ |
| 08 Team | ✓ vesting | ✓ | ✓ | ✓ |
| 09 Legal Compliance | rep only | rep + basics | ✓ | ✓ |
✓ build it · amber partial / conditional · light a founder rep is usually enough. This is diligence-practice consensus, not a rule — an investor with a specific concern will ask for more.
Diligence teams don't open folders in numeric order — they open the deal-breakers first. That's cap table, IP ownership, and any convertible stack, because those are the things that end a deal rather than adjust a price. Put your cleanest, most complete versions of those three folders up first; if a partner's first ten minutes in the room are smooth, the rest of diligence runs on trust rather than suspicion.
The tree above is the shape; here's a quick self-check you can run on your room right now, for free, before paying for anything. For each folder, ask the three questions counsel asks — and if you can't answer "yes" cold, that folder is a gap:
| Folder | Can you answer "yes" from a file — without emailing anyone? |
|---|---|
| 02 Cap Table | Does the fully-diluted total on your table tie to the share ledger and to a board consent for every issuance? If the numbers don't reconcile to the penny, this is your first gap. |
| 03 Convertibles | Is there a single page listing every SAFE/note with its cap, discount, MFN and pro-rata? If the terms only live inside the signed PDFs, the summary is missing — the most common real gap. |
| 04 IP | Does a signed present-tense IP assignment exist for every person who touched the product, including departed contractors? A single missing one is a weight-3 gap. |
| 08 Team | Do founder shares vest, with 83(b) evidence on file? No vesting is a hard blocker most leads won't wire past. |
| 09 Legal | Can you produce a clean litigation rep and your permit/license register today? "I'd have to check" is a gap. |
If you cleared all five cold, your room's fundamentals are in good shape — spend your prep time on the deeper Series A/B folders. If any made you hesitate, that's exactly where a deal re-prices. The live kill-list runs this check across all seven categories and grades it in two minutes, free.
The folder tree above is the same for everyone. The $79 report is the opposite: it scores your answers against the kill-list, tells you which of these folders your specific company is actually missing, and orders them by how badly each open gap re-prices a deal — then ties every gap to the exact document that clears it. Drop in your cap table and it computes your real post-round dilution too. Want the generic-vs-yours difference for free first? Score yourself on the live kill-list.
Get my report — $79 →For a fundraise, the deep folders open after a term sheet or during confirmatory diligence — you don't hand a full financial pack to every first meeting. But the room should be built before you start raising, so that when a lead asks, you populate access in an hour rather than scrambling for weeks. For an acquisition, the buyer's counsel will want the whole room early.
A working spreadsheet (xlsx), not a PDF — the other side wants to run their own scenarios in it. Include a fully-diluted view, the share ledger it reconciles to, and a separate tab or file for the SAFE conversion summary. A PDF of a cap table signals you don't want it modeled, which reads as a flag.
Not at early stages — a well-organized shared drive with per-folder access controls is fine for seed. Dedicated rooms (with view tracking and watermarking) earn their keep at Series B and in acquisitions, where you're managing many parties and want to see who read what. The structure matters more than the tool.
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