Every investor eventually does the same thing: they stop listening to your pitch and start trying to break it.
They test your market, your numbers, your growth story, your team and every assumption holding the company together. In private equity, firms pay McKinsey or Bain hundreds of thousands of dollars to do this work. In venture, the process is faster, but the questions are largely the same.
This playbook shows you how to run that diligence on yourself before an investor does.
Using Claude as a skeptical investment associate, you’ll apply the McKinsey problem-solving method and two of its best-known strategic frameworks to map your risks, pressure-test your answers and uncover the gaps that could kill a deal.
By the end, you’ll have one file: gap-list.md
— a ranked list of the weaknesses an investor is most likely to find, while you still have time to fix them.
Inside You Will Find:
MECE: Map Your Startup’s Entire Risk Surface
Break the business into every area an investor could probe, with no gaps and no overlaps.Issue Trees: Turn Every Risk Into a Question a Data Point Can Answer
Push broad concerns down into specific questions that can be proved with a number, document or fact.Hypothesis-Driven Diligence: Start From the Answer and Try to Break It
Take your strongest claims and attack them like a skeptical investment partner would.The GE-McKinsey Nine-Box: Is Your Market Worth Winning and Are You Built to Win It?
Stress-test the two questions behind almost every investment decision: the attractiveness of the market and your position inside it.Three Horizons: Does Your Growth Survive Past the Core?
Separate what drives the business today from the growth engines investors are actually underwriting tomorrow.
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