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Diligence Ingestion: Data Room to Brain Pages

Goal

Turn pitch decks, financial models, and data room materials into searchable, cross-referenced brain pages with bull/bear analysis.

What the User Gets

Without this: pitch decks sit in email attachments. Financial models in Google Drive. No cross-reference to the company brain page. You can't search "what were the key metrics from Acme Corp's Series A deck?"

With this: every data room document is extracted, diarized, cross-referenced to the company page, and searchable. Index.md gives you the bull/bear case at a glance. gbrain query "Acme Corp revenue growth" finds the exact chart.

Implementation

Recognize data room materials by PDF filenames containing "Data Deck", "Intro Deck", "Data Room", "Cap Table", "Financial Model", "Investor Memo", "Pitch Deck", or series round names. Spreadsheet tabs with Revenue, Retention, Cohorts, CAC, Gross Margin, Unit Economics, ARR. User language like "data room", "diligence", "deck", "pitch", "fundraise materials".

The 9-Step Pipeline

Step 1: Identify the Company. From the document content or filename, identify the company name. Check if brain/companies/{slug}.md exists.

Step 2: Create Diligence Directory.

mkdir -p brain/diligence/{company-slug}/.raw

Step 3: Extract Content.

  • PDFs: Use PDF extraction tool. For scanned/image-heavy PDFs, use OCR (e.g., Mistral OCR or similar).
  • Spreadsheets: Export each sheet as CSV. For Google Sheets: 
    https://docs.google.com/spreadsheets/d/{ID}/gviz/tq?tqx=out:csv&sheet={Sheet Name}

Step 4: Diarize and Save. Write extracted content to brain/diligence/{company}/{doc-name}.md:

  • Document title and type
  • Section-by-section breakdown with key metrics
  • Notable footnotes or caveats
  • Raw data tables where relevant

Step 5: Save Raw Files. Copy original PDFs/files to brain/diligence/{company}/.raw/ Preserve originals for reference. The diarized version is for search.

Step 6: Create or Update index.md. Every diligence directory needs an index.md:

# {Company Name} — Diligence

## Round Details
- Stage: Series A
- Amount: $10M
- Date: 2026-04

## Document Inventory
- [Pitch Deck](pitch-deck.md) — 25 slides, company overview + traction
- [Financial Model](financial-model.md) — 5 tabs, 3-year projections
- [Cap Table](cap-table.md) — current ownership + option pool

## Key Findings
- Revenue growing 30% MoM for last 6 months
- CAC payback period: 4 months
- Net retention: 135%

## Bull Case
- Strong product-market fit signal (NPS 72)
- Expanding into adjacent vertical

## Bear Case
- Single customer represents 40% of revenue
- Burn rate increased 3x last quarter

## Open Questions
- What's the path to profitability?
- How defensible is the moat?

Step 7: Enrich Company Brain Page. Update brain/companies/{slug}.md:

  • Add document sources to frontmatter
  • Update compiled truth with key findings
  • Add "See Also" link to diligence directory
  • If no company page exists, create one via the enrich skill

Step 8: Commit.

cd brain/ && git add -A && git commit -m "diligence: {Company} — {doc type} ingestion" && git push

Step 9: Publish (if asked). When the user wants a shareable brief, create a password-protected published version. Strip internal notes and raw assessment language.

Quality Bar

A good diligence page reads like an intelligence assessment:

  • What they say vs what the data shows (the gap is the insight)
  • Explicit bull/bear case (not just a summary)
  • Key metrics highlighted, not buried
  • Open questions that need answers before decision

Tricky Spots

  1. PDF extraction is lossy. Scanned decks and image-heavy PDFs lose tables and charts during extraction. Always check the diarized output against the original .raw/ file. If key metrics are missing, re-extract with OCR or transcribe manually.

  2. Idempotency on re-ingestion. If the user sends an updated deck for the same company, don't create a duplicate directory. Check for an existing brain/diligence/{company-slug}/ and update in place. Append a version suffix to the document file if the old version should be preserved.

  3. index.md completeness. The index.md is the entry point for the entire diligence package. If it's missing the bull/bear case or open questions, the diligence is incomplete. Always generate all sections even if some require judgment calls -- flag uncertain assessments explicitly.

How to Verify

  1. Search for key metrics. After ingestion, run gbrain search "revenue growth" or gbrain search "{company name} CAC". The diarized content should appear in results. If it doesn't, the sync or embedding step was missed.

  2. Check the company page cross-reference. Open brain/companies/{slug}.md and verify it links to the diligence directory. The compiled truth section should include key findings from the deck.

  3. Verify index.md has all sections. Open brain/diligence/{company}/index.md and confirm it has Round Details, Document Inventory, Key Findings, Bull Case, Bear Case, and Open Questions. Missing sections mean the pipeline stopped early.

Part of the GBrain Skillpack.