06/17/2026
One of the most interesting things about buying a business is that what looks like a red flag isn’t always one.
I’ve seen buyers immediately dismiss businesses because they’ve been listed for sale for months—or even years.
But the better question is often not:
“Why hasn’t it sold?”
It’s:
“What has happened since it was listed?”
A business that has been through multiple failed transactions may tell a very different story than a business whose owner simply isn’t in a rush to sell.
As more entrepreneurs explore acquisition as a path to business ownership, I think learning how to ask better questions will become far more valuable than relying on assumptions.
In the video, I share some of the questions I’d be asking before deciding whether a long-listed business is a concern—or an opportunity.
Have you ever walked away from a deal because something looked like a red flag, only to learn there was a perfectly reasonable explanation?