Streetwise Advice: How to Work with the IRS

Not Your Bank

Too many small businesses view their tax bills like trade debts and delay paying taxes during cash crunches. Invariably, they regret this decision. You can usually delay vendor payments, pay up later, and have all forgotten. When you don’t pay the tax authorities, however, they seek penalties and interest.

These penalties were designed to be severe enough to discourage you from treating the government like a financing company. Furthermore, it is a lot easier for the tax authorities to seize your assets for tax delinquency than it is for a trade vendor to do so!.

Work with the IRS

Although it is true that tax collectors are bound by many rules and regulations, they are often quite flexible to deal with. If you have made an honest tax mistake, have really run out of money, or haven’t filled out the proper form, you might be able to avoid penalty or even interest payments. You just need to find the proper way to channel your request.

For example, in making the giant mistake of handling my own payroll taxes, I neglected to change to a faster payment schedule when the company employee count increased in size. The IRS allows a single occurrence of this oversight without penalty.

Unfortunately, I made this mistake more than once and was hit with a several-thousand-dollar, and perfectly legal, penalty. I paid the penalty but also decided to write to the IRS and plead for a rescindment. Ten months later the IRS refunded my penalty with interest! Naturally, however, the interest refund was subject to taxes.

Decisions and Taxes

Although taxes are a heavy burden on any successful business, you are generally better off if you avoid making business decisions based on their tax implications. Avoiding taxes can mean avoiding profits! Don’t overthink them.

Tax Preparation

Have an outside accountant do your taxes. Even though you might have a great conceptual understanding of tax regulations and filing procedures, someone who files hundreds of tax returns a year will simply be able to do yours more efficiently than you can. They should be up on the very latest in rules and allowances, many of which you may not be aware of. It will save you time, if not money, in the long run—not to mention aggravation!

Don’t Underreport Income

No matter how determined you are to be aggressive with your tax return, don’t underreport your income. The IRS is increasingly suspicious of taxpayers, especially small business owners, who seem to have lifestyles that cannot possibly be supported by the incomes they report.

You could find yourself the subject of a “lifestyle audit.” Furthermore, underreporting income is fraud. You don’t want to do this. You may hear others say, “Everyone does this!” Well, they are wrong; not everyone does this. I don’t do it, and I know a lot of other people who don’t. You don’t have to cheat on your taxes to get rich!

Consider a New Fiscal Year Election

If your business experiences its strongest profitability toward the end of the year, you might be better off ending your fiscal year mid-year. This would delay your income tax payments on year-end profits, as well as your higher estimated income taxes toward next year’s tax bill.

About Bob Adams

Bob Adams is a Harvard MBA serial entrepreneur. He has started over a dozen businesses including one that he launched with $1500 and sold for $40 million. He has written 17 books and created 52 online courses for entrepreneurs. Bob also founded BusinessTown, the go-to learning platform for starting and running a business.