I could have waited and sold for double

A few weeks ago, I was talking to a business owner who sold his family company for a figure that most of us won’t see in several generations.

He wasn’t at retirement age, and his business was thriving. He had a consolidated leadership position in his industrial sector and had spent nearly a decade receiving calls and emails almost every month from domestic and international private equity funds interested in buying a majority or minority stake—and for years, he had always said no. The company was his family legacy, and it was not for sale.

Until one day, it was.

What happened when he paused

At a certain point, for a series of personal reasons, he had to take a break for a few months—something he told me he had never done since he was a child.

During that pause, he saw himself from the outside for the first time.

He had spent decades working twelve-hour days, often including weekends, and even when he wasn’t working, he never truly rested. There was always something on his mind: a problem from the previous day, a risk to manage, a market opportunity he couldn’t ignore. The company lived in his head twenty-four hours a day, even on vacation, even during dinner with his family.

His children were already adults and working in the family business. He had managed to give them a comfortable life, trips, and top-tier education. But only a tiny fraction of his time when they were children. Sunday mornings playing in the park, those small, seemingly insignificant moments that turn out to be the ones you remember—he had lost those forever.

During that pause, with the business doing well and no economic urgency, he reached a conclusion: he didn’t want his children—who in a few years might be ready for the generational handover—to live the same life he had. Suddenly, he realized that he, too, was tired of living this way.

He called his trusted advisors and put the company up for sale.

Was it the best moment to sell?

No. Interest rates were high. When money is expensive, private equity funds have a harder time borrowing and tend to pay lower multiples. Furthermore, the company was in a growth phase; it would almost certainly be worth more the following year, and even more in five years. Maybe double.

I’ve written extensively about when is the best time to sell, what makes a company sellable at a good price, and how buyers really value what’s in front of them. There are market factors and internal factors, and windows that open and close…

But this business owner wasn’t optimizing the price; he was making a life decision, against the advice of his advisors, family, and friends, who encouraged him to wait at least a couple of years to maximize the price. He made that decision alone, as he had always done in important business decisions and in difficult moments—and he sold.

Fatigue as a reason to sell

In my work supporting founders through sales processes, I frequently encounter entrepreneurs who decide it’s time to sell for exactly this reason. I myself went through a very similar situation after 18 years leading my previous company, Antevenio, when an unsolicited offer arrived.

Running a business means carrying the weight (and responsibility) of employees, debt, clients, suppliers, and investment decisions that can go right or wrong. It means being available for emergencies—and there are always emergencies. Today, with the speed at which the technological environment changes, that pressure is greater than ever. The risks are bigger, the opportunities too, and changes come faster than any company can comfortably absorb.

Some entrepreneurs thrive on that adrenaline until the very last day—but many others, at some point, reach a saturation point. A point where the body and mind demand something different.

That moment—when your body asks for it—can be a perfectly legitimate reason to sell, just as valid as any analysis of multiples or market windows.

About the “best moment”

Obviously, if you can choose, it’s better to sell when the market is favorable, when the company has growth visibility, when interest rates make buyer financing easy, and when you can negotiate without urgency. I’ve explained this before.

But life doesn’t always let you choose that perfect moment. Sometimes it lets you choose between selling now, with all the circumstances as they are, or waiting for a better moment that may—or may not—come.

Sometimes the question isn’t when is the best time to sell? but how much longer do I want to keep living like this?

By Joshua Novick, partner at Bondo Advisors