Over 27 years in M&A, I’ve worked with some of the smartest, grittiest entrepreneurs you’ll ever meet. These are people who built companies from scratch, solved complex problems, led teams, and provided for dozens, sometimes hundreds, of families. Their businesses don’t just create jobs. They shape communities and leave legacies.
And yet, for all their expertise and resilience, many of these same business owners struggle with one thing: letting go.
When Identity and Ownership are Intertwined
Earlier this year, Cornerstone commissioned a third-party national study of 750 business owners between the ages of 45 and 75. These were successful people, running companies with $5 million to $100 million in revenue. What we found was eye-opening.
When we asked about their mindset around selling, the number one response was: “I plan to run my business until I’m physically or mentally unable to continue.”
That’s not a strategy. It’s a crisis waiting to happen.
What’s behind that mindset? A staggering 65% of respondents said they’re deeply emotionally tied to their business. When we dug deeper, we found out why:
- 76% had founded their company, birthing it from an idea.
- 16% inherited it from family.
- 5% bought it from an employer.
- Only 3% bought it from a third party.
For most of these owners, this wasn’t just a business. It was a reflection of who they are: their identity, their legacy, their life’s work.
A First-Time, One-Time Event
Here’s the kicker: 97% of these owners had never bought or sold a business before. That means they’ve never gone through due diligence, never structured a deal, never negotiated a sale this complex.
And yet, they get one shot. This is the single largest financial transaction of their life, and there are no do-overs.
Meanwhile, most buyers are trained professionals. Many will look at a thousand businesses and only buy one or two. They come armed with experience, leverage, and a strategy designed to get the best deal for them, not for you.
When you combine emotional attachment with inexperience, it’s easy to see how even the most successful owners can find themselves unprepared and overwhelmed.
Finish Strong on Your Terms
The solution isn’t cold detachment. It’s early preparation.
Start the conversation. Talk to your advisors. Get a fair market assessment done by someone who understands the current M&A landscape. Don’t rely on back-of-the-napkin estimates or rules of thumb.
Once you understand your business’s value, you can look at what you’ll actually net after taxes. Then, work with a financial advisor to compare that net number to your ideal lifestyle. If there’s a gap, you can decide: Adjust your goals or spend a few more years developing your business.
Either way, you’re taking control of your future instead of letting circumstances dictate it.
Don’t Wait
I’ll leave you with a personal story.
My dad wasn’t an entrepreneur. He worked in the offices at John Deere for 28 years. One day, at 60 years old, he came home and told my mom, “I retired today.” They’d offered him a deal he couldn’t pass up: early retirement, full pension, bonus included.
He used those next two years to travel, relax, and play golf with his buddies.
And thank God he did. Because at 62, ten days before my wedding, he had a massive stroke. He lived for five years afterward, but his quality of life was never the same.
If he had waited until he was “ready,” he would’ve missed those good years entirely.
I’ve seen the same thing happen in business. An owner dies unexpectedly, and without a plan in place, the company crumbles. Key employees leave. Value evaporates. The family loses not just a loved one, but their financial security.
Don’t let that happen to you.
If your business is your life’s work, honor that work by preparing for what comes next. You don’t have to walk away tomorrow, but you should know what walking away could look like.
Do it on your timeline. On your terms. While you still have the health, energy, and clarity to choose what comes next.
Because when your business is part of you, planning isn’t just practical. It’s personal.
To Get Started Now
Reach out to the team at Cornerstone Business Services for a Fair Market Analysis. We can work directly with you or your advisors to value your business, outline your exit options, and identify 2–3 ways to increase company value before a sale.
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