A scenario most of us will recognize: the listing asks $900K on $300K of SDE. You go through the P&Ls and notice $40K of "one-time" repairs added back, and the same line shows up in all three years. At 3x, that's $120K of the price resting on an add-back the documents don't support. So you offer $780K. You lose, with no counter. The usual lesson is "should have paid up." I'm not sure that's the right lesson. I think the problem often isn't the lower number. It's the missing reason. There's a classic study in social psychology (Langer, 1978): people asked to cut in line at a copy machine. For a small ask, almost any reason worked, even "because I have to make copies." For a big ask, the empty reason did nothing. Only a real reason moved people. A six-figure price cut is a big ask. "I think the SDE is lower" is an empty reason. "This add-back recurs on all three years of P&Ls, here are the pages" is a real one, and it's something the broker can actually carry to the seller. And the window to build that reason is shrinking. Some brokers want a purchase agreement from day one and a deposit within days of signing, so the "is this number real?" work has to happen before the offer, not during diligence. So, two questions: Brokers: when a buyer comes in under ask, what evidence actually gets you to take it to the seller rather than move on? Buyers: has a documented reason ever gotten you a counter instead of silence? And where's the line between a reasoned offer and a re-trade in disguise? Alex Every AI tool is a Clerk. Verity adds the Guard and the Judge. redacted