Runs structured diligence on an investment or acquisition target across four workstreams - commercial, financial, technical, and legal - and produces a red-flag register split into deal-killers versus manageable risks with a go/no-go recommendation. Use when someone asks "what should I check before investing", "run diligence on this company", "is this deal clean", or is preparing to wire money into a startup or acquisition. Do NOT use for decoding the clauses of a term sheet - use term-sheet-explainer instead; for negotiating terms, use term-sheet-negotiation; for building the target's data room from the company side, use data-room-builder.
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name: Due Diligence Checklist
description: Runs structured diligence on an investment or acquisition target across four workstreams - commercial, financial, technical, and legal - and produces a red-flag register split into deal-killers versus manageable risks with a go/no-go recommendation. Use when someone asks "what should I check before investing", "run diligence on this company", "is this deal clean", or is preparing to wire money into a startup or acquisition. Do NOT use for decoding the clauses of a term sheet - use term-sheet-explainer instead; for negotiating terms, use term-sheet-negotiation; for building the target's data room from the company side, use data-room-builder.
---
# Due Diligence Checklist
Diligence exists to disconfirm the thesis, not confirm it: find the reason not to invest before the money moves. The costly mistake it prevents is confirmation bias - founders are persuasive, decks are polished, and the investor who only looks for supporting evidence reliably finds it. Enter assuming the deal is flawed and go hunting for the flaw; diligence is where skepticism is earned.
## Operating procedure
Run the four workstreams in this order. Commercial comes first because a broken market thesis makes the other three moot; legal comes last because its landmines are cheapest to check once the deal still looks alive.
### Step 1: Gather inputs
Collect before starting, and label every unverified founder claim as a claim:
1. The written investment thesis - one paragraph stating why this deal wins. Every finding gets tied back to it.
2. The data room or document set: financials, bank statements, cap table, material contracts, customer list.
3. Access for 3-5 customer reference calls (default: the investor picks the names, not the founder).
4. Deal type and check size - depth should scale with the check; a small angel check gets the killer questions, not all four workstreams at full depth.
5. Timeline and any exclusivity clock already running.
### Step 2: Commercial diligence - the market and the right to win
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