What’s the biggest blind spot in how buyers evaluate deals today? Here’s mine.
Everyone obsesses over whether EBITDA is real. Almost nobody spends equal time figuring out how efficiently that EBITDA turns into cash. That’s backwards, and it costs people money. I’ve watched buyers fight over a $200K EBITDA adjustment like it’s the Super Bowl, then wave through working capital terms and customer payment cycles without a second look. Three weeks on the quality of earnings report. Three minutes on cash conversion. Here’s what happens next. The deal closes. The multiple looks great on the deck. Everybody shakes hands. Then the business starts eating cash instead of producing it. None of that happened overnight, it was baked in before the ink dried. The buyer just wasn’t looking there. So here’s what changed in how I actually diligence a deal now. Three questions I didn’t used to ask hard enough, and now I won’t close without answers to: 1. What’s the cash conversion cycle, and is it getting longer or shorter? Not the number today, the trend. A business converting EBITDA to cash at 70% two years ago and 50% now is telling you something the P&L never will. Somebody’s financing growth on your dime after close. 2. What does the business need to spend, in cash, just to keep growing at its current rate? Not maintenance capex. Growth capex. Inventory build, AR financing the next cohort of customers, deferred revenue that isn’t actually deferred cash. If nobody can answer this in specific dollars, that’s your answer. 3. Who is actually paying, and how fast? Customer concentration gets attention. Customer payment behavior doesn’t. A book of revenue sitting in 90 day AR with your three biggest customers is a different business than the same revenue collected in 30 days across a hundred accounts, even if the EBITDA line looks identical. The gap between a good investor and a great one isn’t EBITDA analysis anymore. Everyone can do that, half of it gets done by software before you’re even on the call. The gap is understanding the economic engine sitting underneath the earnings number, and asking these questions before you’re in exclusivity, not after. EBITDA gets you in the door. Cash is what pays the mortgage on the whole thing. What’s on your list? Curious what others check now that they didn’t five years ago.