Issue #5 April 14, 2026 5 min read

Due Diligence in 30 Minutes

Someone sends you a pitch deck and a financial model. The board wants your take by Friday. Here is how to produce a structured diligence brief before your next coffee break.

The Problem

A pitch deck lands in your inbox. 32 slides of vision, TAM charts, and hockey-stick projections. Attached: a financial model with 14 tabs. Your job is to figure out whether this is worth the board's time. The founder meeting is Thursday.

So you spend Tuesday afternoon reading slides. Wednesday morning pulling apart the model. Wednesday afternoon writing up questions. You find three red flags on page 11 of the model, but you almost missed them because the narrative in the deck was convincing. By Thursday morning you have a decent brief, but it took 6 hours.

The Fix

  1. Upload both documents to Claude, ChatGPT, or Gemini (the pitch deck as PDF, the financial model as Excel or CSV export).
  2. Paste this prompt after the uploads:
Copy-paste prompt
"I uploaded a pitch deck and a financial model from [COMPANY NAME]. Act as a skeptical due diligence analyst. Create a brief with: (1) Business model summary in 3 sentences, (2) Five key financial metrics with assessment (healthy, concerning, or red flag), (3) Five questions a board member would ask that the deck does not answer, (4) Three comparable companies and how this one compares on unit economics, (5) Risks and assumptions the founders did not highlight. Keep it under 500 words. Use bullet points. Be direct."
What you get

A structured diligence brief with the business model distilled, financials stress-tested, unanswered questions surfaced, and risks the founders glossed over. Ready to share with your board or investment committee. In 30 minutes instead of a full day.

Cost
$0
Time to learn
0 min
Time saved per deal
~4 hours

Why "risks they didn't highlight" is the key line

Every pitch deck is an argument. The founders chose what to show you and what to leave out. The financial model reflects their assumptions, not yours.

AI catches omissions because it doesn't have skin in the game. It reads the deck and the model simultaneously. When the deck says "capital-efficient growth" but the model shows burn rate tripling in Year 2, it flags the contradiction. When customer acquisition cost appears nowhere in the model, it asks why.

The questions your board would ask are often the questions the founders hoped nobody would notice. That is exactly what this prompt surfaces. Not the story they told you, but the story the numbers tell.

Works for

  • Startup pitch decks with financial models
  • Acquisition target packages (CIM + financials)
  • Partnership proposals with projected economics
  • Internal business cases seeking budget approval
  • Vendor proposals with pricing models and ROI claims

10 deals reviewed per year × 4 hours saved each
= 40 hours per year
A full working week you currently spend reading pitch decks. And you still catch more red flags with the prompt than without it.

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