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Separation Anxiety

I felt sorry for Amanda (not her real name), and I sort of felt sorry for myself. You see, I’m not used to seeing adults cry in a meeting, and I didn’t know what to say. I had just told Amanda the range of value for which her company could be sold. It wasn’t anywhere near her expectation, “I have worked so hard, this business has been my baby, my life, for 30 years, and that’s all I can get?

Trying to be rational when the person to whom you are talking is emotional is a tricky balance (36 years of marriage has trained me for that). But in a business context, it can be even more challenging. Amanda has a personal services business that has afforded her a comfortable lifestyle. I could tell she was a hard worker and a nice person, it was clear why she had been successful.  But along the way, I suppose Amanda never thought about what she needed to do to prepare her business for sale. That is, until her husband of 40 years passed away after a sudden illness.

Amanda called me on the advice of her accountant. When we met to review her financial records, the feedback I gave her wasn’t what she expected. Now, if there’s any good news to this story, Amanda’s financial wellbeing is not dependent on how much she will get for the sale of her business. She has been a wise saver over the years and her late husband thoughtfully protected her with life insurance. She told me she was looking to spend her retirement years as a full-time grandmother and volunteering at her church’s daycare. But still, separating herself from her “baby” was going to be difficult. It didn’t take me long to realize that her tears were not coming from the valuation, but from the idea of separation.

I’ve thought a lot about this recent conversation with Amanda. It reminds me of a principle I’ve seen manifest time and time again: the depth of a business owner’s personal attachment to their business (i.e., their “baby”) is usually inversely related to the sell-ability of the business. When the owner is so close to the employees, the customers, or has so much of their personality tied up in the business, it likely means they have treated their business more like a toy than an investment to generate a return. Amanda’s situation isn’t all that unusual, especially with baby boomer business owners who made their business their identity.

I don’t have a simple “do this” piece of advice for owners like Amanda. It’s OK to have an emotional attachment to your work, that can indeed be an honorable thing. But when that emotional connection creates separation anxiety, you know you’ve gone too far.


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. .  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 principles above are true, but the names and fact patterns are changed to preserve the parties’ identities.


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Tennessee Valley Group

Jim is an attorney (non-resident status with the Missouri Bar) and though he no longer practices law, he has read and negotiated enough legal documents to fill a cargo tanker. He has an MBA from Harvard Business School and knows how Wall Street and private equity operates. Jim is a Tennessee Supreme Court Rule 31 listed general civil mediator with tons of experience helping business owners (large and small) work through sensitive problems to achieve winning results. He is the author of "Home Run, A Pro's Guide to Selling Your Business, Seven Principles to Make Your Company Irresistible."

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