Field note · August 2026

The Years Nobody Hears About

Most people assume a business owner either isn’t thinking about selling, or is already out shopping for buyers. In reality there’s a long stretch in between that almost nobody sees. An owner starts turning it over quietly, without telling his team, sometimes without telling his own family, and definitely without telling a stranger.

During that stretch he might already be doing something about it, tightening margins, cleaning up the financials, reducing how much the business depends on him. But he’s doing it privately, under a different explanation, because saying the real reason out loud makes it feel closer to real than he’s ready for.

By the time he’s willing to talk to someone about it, he’s usually already been carrying it alone for years.

That’s the actual window. Not the moment he calls a banker, that’s already late, that’s pressure and picking from whoever’s in front of him. The window is the quiet years before, when nobody’s watching and no one’s earned the conversation yet.

Most of the market shows up once the signal’s obvious, once every other buyer and advisor can see it too. The ones who show up before that are the ones he actually trusts when the day comes.

— Caleb, on why the real relationship starts years before the deal does