How can you tell that an owner is actually ready to sell? Here are a few clues - by David Skinner

If you would like to hear a question to which it is tough to give an interesting answer, it is, “How is the real estate business?” However, today, for the first time in quite a while, I have an interesting answer: deals are starting to sell. Baby Boomers (born between 1946-1964) have controlled industrial operating businesses and the associated industrial real estate for the last few decades, but they are moving on. They are moving on either from their business, their real estate, or both. As we all know, those who can tell the future make the most money, so how can you tell that an owner is actually ready to sell? I am going to share a few clues that I have noticed over the last decade, and you will likely continue to see these clues for the next few years.

If you have been in the industrial real estate business long enough, you can almost feel when a Boomer owner is getting close to selling. These are the same men and women who built their companies from scratch, back when a handshake was a contract and a Sunday afternoon meant tinkering with machinery, not scrolling through CREXi or LoopNet. They have been running the show for 40 or 50 years, and they do not quit easily. For most of them, work is not just what they do, it is who they are. This is why their path to selling is less of a transaction and more of a slow unwinding.

The first stage may start when they cannot keep employees like they used to. The long-time mechanic retires, the foreman takes a job closer to home, and suddenly the owner who swore he would “never pick up a shovel again” is back behind the wheel of a loader or taking customer calls himself. He laughs about it at first, but that is when the conversations begin to shift. 

Then you might notice that a sense of fatigue begins to set in. This is when you start hearing phrases like “I have been doing this for too long,” or “My wife really wants me to give it up.” The thought of a slower life starts to sound less like a dream and more like a plan, but they still may not want to admit it themselves. This does not mean that they are ready; they are still holding on, still paying bills, still opening the shop at 5:30 in the morning.

Next comes the “quiet marketing” phase. This is a sign that the gears are turning. They may call a broker they trust and say something like, “Do not list it, but see if you can find someone who might want to buy. It is not for sale, but everything is for sale.” They do not want the employees finding out or the phone calls from their long-time competitor saying, “I heard Frank is up for sale.” So, they dip a toe into the market, usually at a number that is well above what it is worth. This is a test, not of the market, but of themselves. They are trying to see how it feels to let go.

Eventually, the wall of secrecy starts to crumble. In fact, they may tell you outright, “Go ahead and list it.” That is when you know they have made peace with the idea. The emotional dominoes have fallen. They have accepted that the business they built can live on without them. The mental preparation to sell is as important as any financial analysis or cap rate discussion. Because these deals are not just about money; they are about identity. For decades, these owners were their companies. Their names are on the trucks, their initials on the building permits. Selling means redefining who they are. That is no small task for someone who has been in charge since the good old days of Ronald Reagan.

For brokers, investors, and buyers, recognizing these signs early can make all the difference. When you see the tired jokes, the talk about grandkids, the first whispers of “quiet marketing,” take note. These are not random comments; they are small, but clear signals. They tell you that a once-immovable owner is beginning to soften, to picture life beyond the gate.

So, when someone asks, “How is the real estate business?” you can tell them, it is getting interesting again. The generation that built industrial America is finally ready to pass the torch. And for those paying attention, the next few years will not just be about transactions. They will be about transitions, handled with care, respect, and maybe just a touch of nostalgia.

Prescott is a commercial real estate brokerage specializing in selling and leasing industrial properties with a focus on Industrial Outdoor Storage (IOS) in Greater Boston and throughout New England.

If you own this type of property and you are interested in a sale or lease evaluation or you are looking for property that is very difficult to find, please reach out me at david@prescottios.com or call our office at (617) 340-3332

David Skinner, SIOR, is an advisor, partner of Prescott, Lincoln, Mass.