Investor playbook

Diligence in 14 days

DD that takes 8 weeks signals to founders that you don't actually want to do the deal. Run it in parallel, get to a decision, and don't drag the founder through a process you've privately closed on.

The parallelised 14-day checklist

Six tracks running concurrently. None blocks the others.

Track 1 · Founder references (days 1–4)

Three calls minimum. Two who closed, one who didn't. The one who didn't tells you the most. Ask: "If you'd reported to this founder again, would you?" One-line answer says it all.

Track 2 · Customer references (days 1–7)

Five calls. Top, middle, bottom of the customer pyramid plus 2 churn. Ask each: How did you hear about them? What do they replace? What would you change? Would you renew at 50% price increase? Renewal answer is the single most predictive signal of retention.

Track 3 · Market & competition (days 1–7)

Two analyst calls if you can. Five competitors mapped: positioning, last raise, employee count, product velocity. Output: a one-page competitive landscape your IC will look at. If your firm doesn't do IC, the page is for you to argue with future-you.

Track 4 · Finance & metrics (days 4–10)

Three things to validate against the model: ARR (vs. their accounting), churn (cohort by month, not blended), CAC (sales-attributed only). Recompute everything from raw data — don't trust the founder's spreadsheet output.

Track 5 · Technical & product (days 4–10)

One product walkthrough with the CTO (90 minutes). One architecture review (you or an advisor). For deep-tech: a third-party technical due diligence is worth the $5–15K — not just for risk but for your IC narrative.

Track 6 · Legal & compliance (days 7–14)

Cap table audit, IP assignments, key customer contracts, regulatory licences if applicable. Standard counsel runs this in parallel; you don't read every redline.

The three highest-signal questions

"Show me a customer where you got it wrong."

Founders who can name a specific customer and what they learned have the introspection to scale.

"What metric does your team check first thing in the morning?"

Tests whether internal culture is actually data-driven — and whether the founder pays attention to what their team does, not just what they themselves do.

"Walk me through the customer success ratio for your top two cohorts."

If they can't show retention by cohort, they don't yet have the discipline to scale.

Common diligence failures

• Sequencing instead of parallelising. Each track running alone takes 4 weeks; six in parallel takes 14 days.
• Diligence-by-spreadsheet. Numbers without conversations miss the soft signals. Numbers + 3 conversations is the minimum.
• Confirmation bias. If you've already decided yes, the references will sound great. If you've decided no, they'll sound terrible. Force yourself to write down the failure case before each call.
• Reference manipulation. Founders pre-brief their references. Mitigation: ask for 3 references, then ask each reference for 2 more (downstream). Downstream references aren't pre-briefed.

The decision

By day 14, you should have a clear yes / no / conditional yes. Don't drag founders. The 5-line decision email:

• Decision (yes / no / conditional).
• Two strongest signals.
• Two biggest risks.
• If yes: cheque size, valuation, term sheet timing.
• If no: specific reason + when to revisit.

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