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Let me share with you three quick and true stories of business owners, and how each failed to achieve and maintain financial freedom at exit. 

Story 1 - Joe 

When I first met Joe, he was sitting in his desk chair, a broken man. He had sold his trucking company a couple of years earlier, expecting to fully retire. Joe had received some cash at closing, but a large portion of the deal included debt, financed by him. Shortly after selling, the economy had softened, and the new owner made some bad moves in the market. The company plummeted and defaulted on its payments to Joe. As a result, Joe had to take the business back. However, by then, the company was a shell of its former self, and market conditions stunk. To keep it afloat, Joe had to put back into the company much of the cash he had received at closing. Joe was tired. Joe was dejected. Joe was broken. 

Back in 2011, when Apple announced the retirement of its founder and visionary leader Steve Jobs, the company’s value immediately fell by about $10 billion. (That’s billion with a B.) This dramatic loss of value occurred even though Jobs’ departure had been expected for some time, and his successor Tim Cook was a highly respected leader already established within the company. Investors were simply too disturbed and uncertain about how the company would fare without Jobs as CEO.  

Since then, most of us know that Apple has not only survived, but it has thrived under Cook and other talented leaders. There is an important lesson for business owners with small to mid-market companies: when it is time for you to exit, it must be clear to everybody involved that your company can not only survive your departure but can actually thrive without you going forward. If the company’s leadership is uncertain without you, you find it very difficult to exit happily. Here’s why.

Do you have at least one child working in your family business, and at least one child who is not working in your business? If you do, and if you want to treat all of your children fairly in your business exit and succession planning, prepare not to treat them equally. Because in exit planning for family businesses, fair is not equal and equal is not fair.  

To show why, here’s a true story involving a previous client.

Two businesses are of the same size. One sells for twice the price of the other. Why does this happen? 

It happens all the time. Take two companies from the same industry and similar size, offer them for sale, and one sells for a premium price compared to the other.  

There are factors or conditions within any business that will increase (or decrease) its value at sale. If you are a business owner contemplating selling your company one day, it is essential to know what conditions enhance or detract from company value. These conditions take time to implement or fully realize—sometimes several years or longer. So, the sooner you get started, the better.  

Several years ago, I was sitting in one of our conference rooms with a client. Laid out on the table in front of him were two written offers to buy his company. Both were all-cash deals, but one offer was for several million dollars more than the other.

The client sat there with his fingers steepled under his chin, looking down at the two sets of documents, asking out loud, "Am I crazy? Am I crazy for even considering the lesser offer?"