Prepare a Data Room and Survive Diligence
Assembles what investors will ask for, finds the problems before they do, and decides how to disclose the ones you can't fix. Use it as soon as a term sheet looks likely.
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Prompt
You are preparing this company for investor diligence. Assemble the room and find the problems first.
The business: {{what_you_do}}
Stage and round: {{context}}
How long we've operated: {{age}}
Known messy areas: {{what_you_are_worried_about}}
Team: {{size_and_structure}}
Diligence rarely kills a deal because of a problem. It kills deals because a problem was found rather than disclosed. Everything in this exercise follows from that.
Part 1 — Build the index. Tell me what belongs in each section and what a gap in it signals:
- Corporate: incorporation documents, all shareholder agreements, board minutes, the cap table as a single authoritative source, all option grants with board approval, any promises of equity made in writing or otherwise
- Financial: statements by year, management accounts, the model, revenue by customer, bank statements, debt, tax filings and any outstanding liabilities
- Commercial: signed customer contracts, the standard template, anything non-standard, churn and retention data, the pipeline
- Legal: IP assignments from every founder, employee, and contractor without exception; trademarks; licences; any dispute, threatened or actual; regulatory position
- People: employment contracts, contractor agreements, the option plan, anyone who left with an unresolved claim to equity
- Technology: architecture summary, security posture, open-source licences in use, data protection position and where personal data lives
- Customers and references: who they will be allowed to call
Part 2 — Find the problems now. Ask me directly about the things that most often surface late and cause real damage:
- Equity promised verbally and never documented
- A contractor who wrote significant code with no IP assignment
- A cofounder who left with unvested-but-disputed shares
- Revenue recognised early, or a "customer" who is a pilot, a friend, or not paying
- Customer contracts with change-of-control clauses
- Missing board consents for past share issuances
- Tax filings not made
- A verbal commitment to an investor or advisor that nobody wrote down
Part 3 — For each problem found: can it be fixed before diligence, fixed during, or only disclosed? Fix what is fixable — an IP assignment signed late is far better than one never signed. For the rest, write the disclosure: what it is, what it means, and what we are doing. Disclosed early, most of these are conditions; discovered later, they are leverage or a reason to walk.
Part 4 — Run it well. One organised structure, consistent naming, a single person owning it, and a log of what was asked and answered. Slow, contradictory answers change how an investor reads everything else. Give me the response-time standard to hold to and what to do when we do not have something.