Everyone cheats on their taxes, right?
A $1,500 watch run through the books as “Uniforms Expense.” Twenty dollar bills peeled off a big wad of cash at a construction site in lieu of paying hefty union overtime rates. The systematic re-routing of thousands of dollars in revenue so it never actually hits the books.
Everyone cheats on their taxes, right? Well, actually no, they don’t. I doubt that the entrepreneurs we’ve worked with are the only ones in America who don’t cheat on their taxes. So if you extrapolate from our experience, hundreds of thousands of small business owners manage to succeed – and many get plenty rich — without cheating on their taxes.
Am I just being prudish? I don’t think so. There are a lot of good reasons not to cheat on your taxes, the first of which is that you don’t need to. The biggest tax problem I see among entrepreneurs is that they don’t proactively plan their tax strategy and end up paying too much to Uncle Sam.
In addition, the entrepreneurs I know have enough to worry about. The last thing they need is a constant fear of being audited, a sense of dread that their tax avoidance scheme will come crashing down on them. As Mark Twain said, “If you tell the truth you don’t have to remember anything.”
And if you cheat on your taxes in a major way, remembering is what you’ll have to do plenty of when it comes time to sell your business. During due diligence you have to swear up and down that your books are squeaky clean. Yet at the same time you’ll be arguing for a higher selling price because your prior period earnings were, shall we say, “understated” due to “robust” owner’s perqs. That’s an awkward situation to be in and can get in the way of doing a deal.
Do we ask clients to justify the business necessity of every single meal on their credit cards? Of course not. But when asked in the past to help someone keep two sets of books, I’ve politely declined. Setting aside the reasons above, the ethical considerations, and the professional liability, there’s a fatal flaw with cooking the books: you end up with bogus numbers that are just no good for business planning. So you might be saving money on taxes, but by running blind in other respects, how much money are you leaving on the table?

Becky-Joe said,
March 22, 2007 @ 9:24 am
Hi Dave. In my experience I found it to be true that when someone is serious about growing their company, they will take all the necessary steps to make sure they are adequately covered on both the short and long-term level of protection. Whether it be a workman’s compensation audit or a tax audit. They are less likely to take short cuts which in the big picture ends up being a great mess to clean up. Who wants that?