Selling a Small Business During the BabyBoomer Exit Wave
Selling a Small Business During the Baby Boomer Exit Wave
What today’s shifting ownership landscape means for buyers and sellers in the main street business market — and why 2026 is the year to stop waiting.
One of the biggest shifts happening in the small business market right now isn’t interest rates, SBA policy changes, or valuation multiples. It’s demographics.
More than 11,000 Americans are turning 65 every single day in 2025 and 2026. Demographers are calling this period “Peak 65” — the largest surge of retirement-age Americans in U.S. history. A meaningful number of those people own privately held small businesses. Many of those companies are strong, profitable operations built over decades. And a surprising number of those owners still don’t have a succession plan or an exit strategy in place.
We’re already seeing this play out across Arizona, Minnesota, South Dakota, and throughout the broader main street market. Construction companies, manufacturing operations, service businesses, HVAC companies, distribution firms, retail operations, and trades-based businesses are increasingly owned by sellers who are approaching — or well past — traditional retirement age. In many cases, these owners have spent their entire lives building something real. They just haven’t spent much time figuring out what happens next.
| 11,000+ Americans turn 65 every day in 2026 |
~2.34M Boomer-owned small businesses in the U.S. |
$5.1T Annual revenue generated by Boomer-owned businesses |
72% Boomer owners with no formal succession plan |
For Business Owners Thinking About Selling
For Sellers, Timing Matters More Than Most People Realize.A business that goes to market because the owner is proactively planning their next chapter is a very different animal than one that’s forced to sell because of burnout, a health concern, a partnership dispute, or just running out of runway. Buyers can feel that difference quickly. The strongest outcomes — the cleanest deals, the best prices, the smoothest transitions — almost always happen when owners start preparing before they actually need to exit.
That preparation doesn’t necessarily mean selling tomorrow. In most cases, it means taking steps over the next one to three years to make the business more transferable. Buyers in today’s market are paying close attention to how a company is structured, how deep the management goes, whether customer relationships are concentrated in one person, how clean the financial reporting is, and how dependent the operation is on the owner showing up every day. Businesses that can continue running smoothly after a transition create confidence with buyers. They also create confidence with SBA lenders, which matters in this price range.
“Buyers are looking for solid books, stable revenue, and minimal owner involvement. If one person is doing everything and nothing is documented, that undermines confidence in the business’s operational resilience.” — M&A advisor, 2025.
The cost of waiting isn’t always obvious until it’s too late.
Buyers look at trajectory, not just last year’s numbers. A business that’s been coasting for two or three years — even a profitable one — tells a different story than one that’s been actively managed and positioned for a sale. That affects your valuation, your buyer pool, and how competitive your listing looks in a market that’s about to see significantly more inventory.
Your energy matters more than you think. The best deals happen when the seller is sharp, present, and can talk about the business with clarity. Buyers read the seller as much as they read the financials. If you’ve already mentally moved on, it shows — and it affects how both buyers and lenders assess the opportunity.
More sellers in the market changes the math. McKinsey’s 2026 research on small business succession estimates that by 2035, roughly six million small and mid-sized businesses will come to market as Baby Boomer owners retire. According to a 2026 Fortune analysis of that same data, 92% of small business market exits today happen through closure — only 5% through a sale. The businesses that sell well will be the ones that prepared. The ones that didn’t tend to sit, discount, or close.
One more thing worth saying: most owners significantly overestimate what their business is worth before they ever get a real valuation. That gap between expectation and reality is one of the most common reasons deals fall apart or never get started. Getting a professional valuation done early — before you’re in a hurry — is one of the most valuable things a business owner can do. Only about 15% of Boomer business owners have ever had one done.
If you’ve been thinking about selling your business in Minnesota, Arizona, or South Dakota in the next two to five years, the right time to start that conversation isn’t when you’re ready to be done. It’s now — while you still have runway to position things properly and get full value for what you’ve spent a lifetime building.
For Buyers Looking to Acquire a Small Business
For Buyers, This Market Is Creating Opportunities That Didn’t Exist at This Scale a Decade Ago.A growing number of profitable, owner-operated businesses will change hands over the next several years — particularly in industries where succession planning has historically been limited. These aren’t struggling companies. Many of them have long-standing customer relationships, established cash flow, experienced employees, and reputations built over decades within their communities. Boomer-owned businesses currently generate over $5.1 trillion in annual revenue in the U.S. Nearly 75% of them are profitable.
At the same time, buyers should understand that not every business coming to market is automatically a good opportunity. Some owners do wait too long. Some have outdated systems, limited financial visibility, deferred maintenance, or operational structures that are difficult to step into. The businesses attracting the strongest buyer interest right now are the ones that are organized, financially clean, and realistically priced for what they are.
What Makes This Buyer Opportunity Different
The sellers in this wave are motivated differently. A 66-year-old who built an HVAC company or a landscaping business over three decades isn’t just chasing a number. They’re often more focused on what happens to their employees, their customers, and their reputation after they walk out the door. Research published in 2025 found that 60% of Baby Boomer business owners are open to seller financing — not out of desperation, but because finding the right buyer matters more than squeezing every last dollar. For buyers who show up prepared and treat the conversation with genuine respect for what was built, that creates a real advantage.
Many of these businesses are undervalued on paper. Owner-operators in this generation often run their businesses in a way that’s optimized for their lifestyle, not for sale. Add-backs haven’t been documented. The books may not fully reflect what the business actually earns. Customer relationships are strong but informal. A buyer who can see past the surface numbers — with the right guidance — will often find more value than the tax return suggests.
Transition support is more available here than in most deals. Buying from a retiring Boomer seller frequently comes with seller training periods, seller notes, and structured earnouts — not as warning signs, but because the seller genuinely wants the business to land well. BizBuySell’s 2025 data shows that over 56% of today’s business buyers have never owned a business before. That makes having an experienced broker in your corner more important, not less.
More professionals are exploring acquisition instead of starting from scratch. Some are leaving corporate careers. Others want more control over their income and future. Buying an established Main Street business with existing customers, employees, and cash flow has become a much more serious consideration for a broader group of buyers than it was even five years ago.
Acquisitions at the main street level still require careful evaluation. Financing structure, inventory, equipment condition, customer retention, lease terms, seller involvement after close, and transition planning all materially affect the quality of a deal. Two businesses in the same industry with similar revenue can produce very different outcomes depending on how they’re structured and operated.
The volume of sellers, their motivations, and the types of businesses currently coming to market in Minnesota, Arizona, and South Dakota make this one of the better windows for a prepared buyer in a long time. But “prepared” is the operative word. The deals that go sideways almost always involve a buyer who moved too fast, skipped due diligence steps, or didn’t have the right people around them when it mattered.
The Reality Is That This Wave Is Already Here
The Baby Boomer business exit wave isn’t some future event on the horizon. It’s already happening. The owners who prepare early consistently position themselves better. The buyers who understand what to look for tend to move more confidently when the right opportunity appears.
There’s a version of this transfer that goes well — where businesses find the right buyers, employees keep their jobs, customers keep their relationships, and owners get fair value for what they built. There’s another version where it doesn’t go that way, where sellers waited too long or went it alone, where buyers overpaid or missed things that proper diligence would have caught.
The difference between those two outcomes usually comes down to one thing: whether the right conversations happened early enough.
At Cooperhawk, we work with business owners and buyers throughout Arizona, Minnesota, and South Dakota to navigate these transitions — strategically, confidentially, and with long-term goals in mind. We’re not here to rush anyone or chase a deal. We’re here because selling or buying a business is one of the most consequential financial decisions a person makes, and it deserves to be handled by people who take that seriously.
Whether you’re thinking about selling in the next few years or exploring acquisition for the first time, having the right conversation early almost always creates a better outcome. Reach out. That conversation costs nothing, and it’s the right place to start.
Brian Aagaard
Cooperhawk Business Brokerage
Minnesota: 952-479-0908 | Arizona: 602-844-6161
brian@cooperhawkbrokers.com | cooperhawkbrokers.com
THE COOPERHAWK DISPATCH · May 2026 · Minnesota · Arizona · South Dakota
