He built a $22M business but waited too long to sell it.

By Scott Bushkie

Keith spent decades building a thriving business. It was valued at $22 million when my team at Cornerstone Business Services completed a Real Market Analysis for him. Keith met with his tax and financial advisors and confirmed he could sell and live exactly the life he wanted.

There was one problem: He couldn’t let go and put it on the market. 

This is not unique. Sixty-five percent of business owners say their identity is deeply tied to their business, and 35% can’t imagine life without it, according to my firm’s 2025 National Study on Selling Your Business. That sense of attachment and identity is why most owners don’t sell too soon. They sell too late, or not at all.

Scott was among them. 

Year one, he wanted to pay down some debt first. In year two, he’d lost a small customer (who accounted for less than 2% of revenue) and wanted to replace that account before moving forward. From our point of view, neither action would have meaningfully changed the value of his business, but he wanted to wait.

Heading into year three, Keith and Scott made plans to meet at a Packer game at Lambeau Field in Green Bay, Wisc., at halftime, just to catch up. But Keith never showed. Texts went unanswered, and calls went to voicemail.

Five days later, Keith’s phone number appeared on Scott’s phone. It was Keith’s wife, Lisa. Keith had suffered a major stroke at the stadium and had been taken by ambulance to a local hospital. Things were touch-and-go.

Keith was still in the hospital when he asked Scott to visit. As the machines beeped around him, Keith acknowledged, “It’s finally time to sell. I’ll be out of here in a couple of weeks, and we’ll get this started.”

A few weeks later, Lisa called again. Holding back tears, she said, “Keith is gone.” Without him, the business was unraveling rapidly. A couple of key employees had already left. A few customers followed.

From there, it was a house of cards. Eventually, Lisa and their two adult children liquidated the business for pennies on the dollar. 

It doesn’t have to be that way. However, if you want to sell your business for the best price and to a buyer you trust, you need preparation and momentum on your side.

Preparing for your exit doesn’t mean selling tomorrow. It means having a plan — a Real Market Analysis, a team, a roadmap — so that if something forces your hand, you’re ready. And if the timing is right, you go out on top.

Had Keith drafted a plan, he would have been able to sell on his terms, at the right time, for $22 million. By waiting one year too long, he left his family a business worth very little. Time was on his side until it wasn’t. 

Keith missed his chance to sell at an attractive valuation, but many of the owners we work with still have significant opportunities to do so. Ultimately, timing matters when you sell a business, and you have to be willing to act when the ideal moment arises.

Scott Bushkie is managing partner and founder of Cornerstone Business Services in Green Bay, Wisc.