The Best Time to Sell Your Business May Be When You Least Want To
By Brian Wheeler, Director of Wealth Management & Business Brokerage
What if the best time to sell your business comes at exactly the moment you have the least interest in selling it? That’s one of the more difficult conversations I have with business owners. When the business is growing, profits are strong and everything seems to be working, selling can feel almost ridiculous. Why walk away now? Why not enjoy another few years of growth?
When the Timing Changes
The problem is that buyers may be looking at those same results and thinking something very different:
“This is exactly the kind of business we want to buy.”
And sometimes that window doesn’t stay open as long as we think. I’ve watched this happen firsthand.
We worked with an owner who considered selling while the business was performing very well. Ultimately, the decision was made to keep going. And at the time, that decision made perfect sense. Business was good.
About a year and a half later, the owner was ready to revisit the sale. Only now, things had changed. Results were beginning to decline. Some of the momentum was gone. The owner was more ready to sell—but unfortunately, the business wasn’t quite as attractive as it had been 18 months earlier.
It was still a good business. But the conversation around value had changed.
That’s the irony of timing a business sale: when everything is going well, selling can feel unnecessary. When things aren’t going as well, selling can suddenly feel very necessary.
And buyers know the difference.
What Buyers See in Your Business
This is also why understanding what actually drives the value of your business matters long before you’re ready to sell.
Revenue and profitability certainly matter, but buyers look much deeper. They want to understand the quality and transferability of the business they’re buying.
There are eight key drivers of business value that we spend time discussing with owners—things like financial performance, growth potential, recurring revenue, customer concentration, management strength, competitive differentiation, systems and processes, and how dependent the business remains on the owner.
An owner may look at the company and see 20 or 30 years of hard work, relationships and sacrifice. A buyer looks at the same company and asks:
“What happens to this business after you leave?”
That’s a very different perspective.
The good news is that many of the things that influence value can be improved. The problem is that they usually can’t be fixed six months before you want to sell.
Preparing Before You're Ready
Which brings me to another point I make with owners: selling a business probably shouldn’t begin with waking up one morning and deciding, “Today’s the day.”
There are too many other pieces that need to line up.
What does life after the business look like? How much income will you need? What does the business need to sell for to support that lifestyle? What are the tax implications? How does the sale fit with your estate plan? And what do you actually want to do when Monday morning no longer means going to the business?
As a wealth advisor and CEPA®, that’s where much of my work with business owners begins. Before we’re talking about a transaction, we’re trying to connect the value of the business with the owner’s personal financial plan and the life they want to have afterward.
Sometimes that planning tells us they’re closer than they thought. Sometimes it tells us there is work to do. Either answer is valuable—especially when you still have time to do something about it.
The Advantage of Having Choices
I think one of the best positions a business owner can create is having a valuable, transferable business, a personal financial plan that works, and no immediate need to sell.
That’s when you have choices.
You can continue growing. You can watch the market. You can consider an unexpected offer. Or, when the business is performing exceptionally well and buyers are willing to recognize that value, you can decide that maybe this actually is the right time.
After spending decades building a business, the final chapter deserves more thought than simply deciding you’re ready to be done.
Top value usually comes from thoughtful preparation, a business built to transfer, and the ability to recognize exceptional timing when you have it.
