Over the recent holiday season, I met a gentleman who had recently sold his company.
I expected to hear pride.
Relief.
That quiet sense of “I did it.”
Instead, I met a man filled with resignation and regret.
The Backstory
This was a family-owned business.
He was the youngest family member still working in the company. The senior generation was ready to exit, cash out, and retire. That part made sense.
They hired a business broker to help sell the company.
And here’s where things began to drift.
The family decided that this gentleman would stay on with the business post-sale to ensure a “smooth transition” for the buyer. Clients would feel comfortable. Continuity would be preserved.
At least, that was the plan.
A Clarification That Matters
Let me be clear about something.
This wasn’t a bad broker. It was a misunderstood role.
Brokers facilitate transactions.
They don’t coach sellers through identity, leverage, or life-after-exit decisions.
And that distinction matters—a lot.
What Actually Happened
After the sale closed, he was miserable.
The buyer didn’t embody the culture of the company.
Employees left.
Clients left—because the customer experience eroded quickly.
What used to feel like his business now felt like a foreign place wearing a familiar logo.
And he was stuck.
Locked into a five-year contract that would take him right up to retirement.
No leverage.
No exit.
No joy.
Why This Happens More Than You Think
Here’s what makes this so dangerous:
None of this felt risky at the time.
Everything looked reasonable.
Everyone sounded confident.
That’s how these decisions usually go sideways.
There’s no single red flag. No dramatic collapse. Just a series of “this should be fine” decisions that quietly strip sellers of leverage before they realize what’s happening.
And when you layer in family dynamics, the risk multiplies.
Family dynamics add urgency, guilt, and unspoken pressure — which is exactly when outside, experienced counsel matters most.
But that’s also the moment when people are least likely to ask for help.
From Owner to Employee—And Trapped
This former business owner is now an employee.
He feels beholden to a company that no longer reflects his values.
He’s riding out the final chapter of his career not by choice—but by contract.
It’s a sad situation.
And unfortunately, it’s not rare.
What I’ve Seen Up Close
I’ve taken 11 clients through the process of potentially selling their businesses.
Only one has sold.
Why?
Because selling a business isn’t just a financial transaction.
It’s an emotional, strategic, and identity-shifting event.
Issues that routinely surface include:
- Last-minute changes to term sheets, that reduce price
- Contract clauses that benefit only the buyer
- Seller’s remorse that causes owners to pull the business off the market
- No clear answer to the question, “What’s next for me?” When there’s no next step, many owners don’t sell—not because the deal is bad, but because the unknown feels worse than staying put.
The Real Lesson
The biggest mistake I see entrepreneurs make at this stage isn’t about valuation or deal structure.
It’s not asking for help from people who have already walked the path.
Whether it’s pride, optimism, or simply not knowing what you don’t know, the outcome is the same:
You pay for the help you didn’t hire.
Sometimes with money.
Sometimes with time.
And sometimes with regret.
And here’s what I’ve learned from the exits that did go well:
The most successful exits I’ve seen weren’t driven by brilliance.
They were driven by humility — knowing when to bring in people who knew more.
A Question Worth Sitting With
If you’re thinking about selling your business—now or someday—ask yourself:
Who is truly representing your interests?
And who has the scars to prove they’ve been here before?
Because the price of not asking for help is often far higher than the cost of getting it.
And unlike most business mistakes, this one is very hard to undo.
With Gratitude,
