The owner wave in Chicagoland, and what it does to prices.
A large share of the region's shops, distributors, contractors and practices are owned by people in their sixties and seventies, and the handoff has started. More sellers in the same markets means buyers with a checklist and options. Prepared businesses get cleaner terms. Here is what that means if you're two or three years out.
The retirement wave is real, and it's local.
U.S. businesses expected to change hands by 2035 (McKinsey, 2026)
U.S. small businesses are owned by baby boomers, by most industry counts
owners have a written exit plan when the first buyer calls (Exit Planning Institute)
Those are national figures, and we use them sparingly. The local version is what we see on site: an owner in his late sixties, a business that has never been valued by anyone who wasn't selling something, and a first buyer who has already called.
What it does in the six counties.
More sellers. In Cook, DuPage, Kane, Lake, McHenry and Will, the businesses coming to market over the next decade are the ones founded in the seventies, eighties and nineties: machine shops in Elgin and Aurora, distributors along I-88, HVAC and plumbing companies in the western suburbs, dental and veterinary practices on the North Shore. Many of them will come up for sale within a few years of each other, in the same categories, to the same buyers.
Buyers with a checklist. The roll-ups and platform buyers working these categories have done this many times. They know what a prepared business looks like. When they have a choice between two similar companies, the one with clean books, documented add-backs and a manager who can run the place gets the offer, and the other one gets a lower offer or an earn-out.
Cleaner terms for prepared businesses. When buyers have options, the headline price is only part of what moves. The share paid in cash at close, the size of the holdback, the length of the earn-out and the transition you're asked to work all get better for the prepared business and worse for the unprepared one. That's true in a strong market and more true in a crowded one.
What a two-year head start is worth.
We don't quote a multiple for a business we haven't read, and you should be careful of anyone who does. But the typical effects of the common gaps are consistent enough to plan around. Cash-basis books with no monthly close commonly cost 5 to 10 percent in diligence. Sales that depend on the owner take roughly half a turn off the multiple. A customer over 20 percent of revenue tends to move part of the price into an earn-out or a holdback. Working capital with no target set before the LOI turns into a deduction at close, often six figures.
Now look at the fix times. The books take 60 to 90 days, the add-back schedule about 30, and a working-capital target about 60. Written SOPs take three to six months. Moving the top customer relationships to someone other than you takes six to twelve months, and rebalancing customer concentration a year or more. Very little of that can be done while the business is on the market, and none of it can be done in diligence.
Two years is about what it takes to do all of it without disrupting the business. One year gets most of it. Ninety days gets the books and the add-backs, which is still worth doing. The honest caveat is that the ranges are wide and depend on your industry, your size and who's buying, and that's what the free value range is for. What buyers look for has the full list with the effect of each item.
Signs the timing is closer than you think.
Any one of these means it's time to know the number, even if the decision is to wait.
- A competitor, a roll-up or a searcher has called, or sent a letter that's still on your desk.
- A key employee or a manager has asked about buying in, or wants equity to stay.
- You've stopped reinvesting. The equipment is fine, but you haven't bought anything you'd need to still be here in five years.
- Your health, or a family member's, has moved the question from someday to when.
- A partner wants out, or the partners don't agree about the next five years.
Three things to do before the end of the quarter.
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Get the range
Revenue, industry, and an email address. Within two business days you have a CPA-prepared value range and the two or three items a buyer's accountant would raise first. Free, confidential, nothing to sign. Request the value range.
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Fix the books
Move to a monthly close if you aren't there, and build the add-back schedule with receipts behind every line. Your bookkeeper can do most of it in 30 to 90 days, and it's the cheapest 5 to 10 percent you'll ever recover.
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Pick the exit window
Decide the year, then work backwards. Six to twelve months of preparation, then six to nine months for the sale itself. If the year is next year, the preparation starts now. If it's three years out, you have time to fix the slow items. A 30-minute consult is the easiest way to set the window.
If you'd rather have the gaps priced before you decide, the Exit-Readiness Review is two weeks and $4,500 flat, credited against our fee if we later list. All services and fees. Timing questions are also answered in the owner FAQ.
Thirty minutes with a CPA. Your numbers, straight answers.
Pick two windows and he'll confirm one within a business hour. Or call the office, weekdays 9 to 5. A person answers.