“Everybody knows it’s time he should sell, but he can’t seem to let it go.” Bruce (not his real name) is the head of marketing for a company owned by Philip (not his real name). Bruce called for my advice on structuring an employee-led buyout. He admitted it was a long shot even though Philip is in his late-70s. It seems Philip has heretofore not been willing to even entertain the idea of selling. But Bruce and his team are undeterred. He and the company’s CFO want to form a partnership to buy the company, and they are working hard to develop a proposal that includes a clear explanation of valuation and how the transition would occur. They have done their homework, which looks solid to me. But the more we have talked, I told Bruce I didn’t think his plan would work. He said he agreed, “but at least I can tell myself that I tired.” Bruce’s conundrum is not unusual. I regularly meet or hear about business owners who are well past the age of retirement yet unwilling to let go of their company. I haven’t found a common link to explain this reticence, but I see one of these syndromes in almost every situation: -- The owner knows the business value will not support him/her in retirement (the “can’t afford to retire” syndrome). -- The owner is afraid of the “Bear Bryant” syndrome (Bear died a few months after retiring as head football coach of the University of Alabama). -- The owner does not have a life outside of the business and the prospect of not having a place to go every day is scary (the “lonely heart” syndrome). -- The owner is attached to the company’s employees and afraid any buyer will change the culture or structure in a way that is disruptive to their lives (the “godfather” syndrome). I have been working with business owners long enough that I can recognize each syndrome early in a conversation. Yes, the time eventually comes when every business is sold, somehow someway. Sometimes it’s the owner’s heirs who must do it, sometimes it’s the owner’s banker who demands it, and sometimes it’s the auctioneer selling assets for dimes on the dollar. But there are times the owner is cured of his/her syndrome and ready to sell. I will continue to help Philip and his partner, maybe 2024 will be the year Bruce is cured of his syndrome and ready to let it go.