It’s human nature to want to time things perfectly—whether it’s the stock market, a putt through a windmill’s oscillating blades, or selling your business. Timing is important; and in this economic environment, it’s crucial. Because when it comes to middle market M&A, waiting too long to sell can be one of the most expensive decisions a business owner ever makes.
At Caber Hill Advisors, we work with business owners who have spent decades building profitable companies in sectors like healthcare, facility services, and industrials. These companies are often highly attractive to strategic and financial buyers—until they’re not.
Timing truly is everything. And unfortunately, many owners miss their window by holding on just a few years too long.
In this post (which is companion piece to an earlier article, “Is Now a Good Time to Sell? PE Says No. Brokers Say Yes. Neither Are Right.”), we’ll explain why delaying your exit can lead to diminished value, lower buyer interest, and missed opportunities.
1. The Business Cycle Doesn’t Wait for You
No business, no matter how strong, is immune to the natural ebbs and flows of the market. Buyer appetite, capital availability, and sector-specific trends all influence valuations.
Our January 2025 survey of over 250 private equity partners specializing in the middle market showed zero respondents believed deal flow would weaken in 2025, while 25% forecasted it to remain steady, and 75% predicted it would strengthen.
That creates a window of seller-friendly pricing that won’t stay open forever. Even a short delay into a less favorable cycle—marked by rising interest rates, higher borrowing costs, and muted buyer appetite—can erode multiples and overall deal value.
2. Buyers Pay for Future Growth, Not Past Glory
A common misconception among owners is that buyers will reward decades of hard work and historical profits. But in reality, buyers are investing in future earnings potential not what the business did five years ago. Future EBITDA, not historical earnings are what buyers are laser-focused on.
When revenue growth slows or plateaus (for any number of reasons, including market saturation, loss of key customers, or simply aging leadership) valuations start to compress.
Buyers want upside. If they don’t see a clear path to scale, they’ll either lower their offer or walk away entirely.
By selling while your business is still growing, you’re presenting a more compelling story—and commanding stronger multiples.
3. Owner Fatigue = Value Drain
Sellers often underestimate how much fatigue can subtly impact performance. We’ve seen it happen: a once-thriving business starts to lose its edge. Marketing slows, hiring gets delayed, innovation stalls, and key team members start to leave. Buyers notice these red flags—and they price them in.
The most successful exits happen when the owner is still energized, engaged, and running the business like it’s NOT for sale.
After 20 or 30 years of leading a company, it’s natural for fatigue to set in. But for owners who delay an exit because they “aren’t quite ready,” the risk is that fatigue leads to complacency, which leads to underperformance and lowered valuations.
4. External Risks Compound Over Time
No one can perfectly predict the next regulatory change, supply chain disruption, or interest‑rate spike. These external factors accumulate year over year. And they are completely outside your control.
The longer you wait to sell, the more likely one of these risks becomes reality. Once it does, even a well-run business can see its valuation suffer.
Selling while the macro environment is still favorable gives you more control over the outcome.
5. Selling Doesn’t Mean Retirement
Many owners delay selling because they aren’t sure what they’ll do next (what often boils down to “not being ready”).
But selling doesn’t mean retirement anymore. An exit doesn’t guarantee a daily tee time at the country club (though that does sound nice). Selling today translates to liquidity, security, and freedom to choose what comes next.
For many owners we advise, what’s next is launching a new venture, investing, or spending time with family.
WATCH Dr. Anthony Ponzio talk to Craig about how his practice acquisition wasn’t about getting out “to live on a beach somewhere.”
Our advisors understand that selling a business is a deeply personal and emotional decision. But it’s also a financial, one of which timing can dramatically impact the outcome.
If your business is performing well, buyers are active in your sector, and your own energy is beginning to shift, that’s not a reason to wait. It’s a signal to act.
At Caber Hill Advisors, we help middle market business owners evaluate their timing, understand their value, and execute successful exits on their terms. If you’re wondering whether now is the right time to sell, let’s start the conversation with Craig Castelli or another member of our advising team.
A confidential, no-pressure conversation could help you avoid leaving millions on the table.
