July 22, 2026
Five questions we ask before any deal — and the answers that end the conversation
Our diligence starts long before the data room. These five questions kill more deals than every spreadsheet we run afterward.
[Placeholder article — replace or edit via the site admin at /admin.]
Most bad investments announce themselves early. You just have to ask questions that give them the chance.
1. Who, specifically, is the customer?
If the answer starts with "everyone who…", we're already reaching for our coat. A business that can't name its customer can't price, can't position, and can't defend anything.
2. Why do customers stay?
"Our service is great" is not an answer; it's a hope. We want mechanics: switching costs, integration, habit, contracts, relationships. Retention with a reason attached.
3. What happens if the owner disappears for 90 days?
The honest answer tells you whether you're buying a business or buying a job. Both can be fine — but they're priced very differently, and sellers only ever quote you the first one.
4. Why is this available to us?
Capital is abundant. Good deals get taken. If something reached us, there's a reason — sometimes innocent (bad marketing, no network), sometimes not (a problem wearing makeup). We don't proceed until we know which.
5. What would have to be true for this to fail?
Flip the pitch. Every deck tells you what has to go right; discipline is listing what has to go wrong and asking how likely each item really is. If the failure list is short and improbable, that's signal.
None of this is sophisticated. That's the point — the discipline is in actually asking, deal after deal, especially when the deal is charming. Charm is the most expensive thing in finance.