Chapter 8

“Tax Payments Can Be the Difference between Survival and Failure”

It’s difficult to embark on a project of this kind completely free of expectations regarding what you’re likely to hear. As we set out to ask entrepreneurs across the nation about the issues and challenges that complicate their efforts, one of our expectations was that taxes might come up as a source of frustration. After all, any business owner would naturally prefer to keep as large a portion of the business’ earnings as possible—to reinvest into the business or to simply enjoy more of the fruits of one’s labor.

And, indeed, as we expected, the subject of taxes came up frequently—but not in the way we expected. In fact, all over the country we heard entrepreneurs make comments such as: “I understand that we all have to pay taxes,” and “I’m fine paying taxes,” and even, “I didn’t get into business to avoid paying taxes.” And yet our roundtables made clear that taxes are a source of frustration and even anxiety for many of our participants.

For a while, we were puzzled by this nuanced, even seemingly contradictory feedback regarding taxes. But as we continued to listen, we began to understand.

“We literally spend thousands of dollars a month on accountants,” said Mark Casey, president and chief executive officer of CFN Services, a telecommunications networking company based in Herndon, Virginia. “Sometimes the issue is getting bills for taxes that we’re not even aware that we owe. How do you find out about ...

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