“Everybody knows it’s time he should sell, but he can’t seem to let 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 had heretofore not been willing to even entertain the idea of selling. But Bruce and his team were undeterred. He and the company’s CFO wanted to form a partnership to buy the company. They had gone so far as to talk with bankers about financial support. Bruce came to me at the advice of a banker to help him and his partner create a plan to present to Philip explaining valuation and their proposed transition structure. But the more we talked, I came to realize Bruce didn’t think his plan would work. It was like he was going through the motions so he could tell himself he at least tried. 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 (he 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 these syndromes early in a conversation. Yes, the time eventually comes when every business is sold, somehow someway. Sometimes it’s the owner’s heirs who have to 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. Bruce decided to wait another year, hoping Philip will find a remedy for his syndrome and be ready to talk transition in 2020. JIM CUMBEE is President of Tennessee Valley Group, Inc. a retainer-based business brokerage and transition mediation firm in Franklin, TN. Cumbee is an attorney and has an MBA from Harvard Business School. Jim is the author of Home Run, A Pro’s Guide to Selling a Business. https://www.amazon.com/Home-Pros-Guide-Selling-Business/dp/1599329239 .  He has a wide range of corporate and entrepreneurial experiences that make him one of the most sought-after business transition advisors in the state of Tennessee. The story above is true, but the names and fact patterns above have been changed to preserve the parties’ identities.