How Businesses Get in Trouble with Taxes

Understanding "Willful Tax Evasion"

Business Tax Evasion
Business Tax Evasion. Joanna Pecha/Getty Images

The single biggest tax mistake businesses - and individuals - make is to willfully evade paying taxes. I'm not talking about honest mistakes or errors. I'm talking about what the  "voluntary, conscious, and intentional" conduct. It's the difference between "avoidance" and "evasion."  Tax avoidance is legal; tax evasion is not. 

In a recent article on discusses what the IRS deems to be "willful" tax mistakes.

Willful tax evasion can be either a sin of commission (intentionally doing something, like paying in cash) or a sin of omission (failing to include income or failing to file a tax return. 

If the IRS, and/or the Tax Court, deem that an act by a taxpayer is "willful," it can mean increased fines and penalties, including jail time. (See the below). 

Incorporated into this subject are 3 types of willful acts that can be big mistakes for businesses.  

1. Under-reporting income. All business income must be reported. This includes income from barter transactions and cash transactions.  Another common way businesses under-report income is to avoid reporting large cash transactions by keeping deposits under $10,000. Deposits of $10,000 or more are required to be reported to the IRS. 

Some businesses try to avoid issues with payroll taxes by paying employees in cash. Paying in cash usually means no withholding for income taxes and FICA (Social Security and Medicare) taxes are paid.


2. Over-reporting expenses. Some of the most common ways businesses over-report expenses are: 

3. Not reporting taxes. The most common instances of failing to report taxes are failure to report sales taxes and payroll taxes. These taxes are called "trust fund" taxes, because they are collected from others (customers, in the case of sales taxes; and employees, in the case of payroll taxes) and held in trust by the business, to be reported and paid to the appropriate taxing authority. Willfully using these taxes to fund a business instead of reporting the collection and paying when due is tax fraud. 

Lifestyle and Tax Fraud

One of the most common ways businesses are caught in tax fraud is to have a lifestyle that's not aligned with their reported income. A high-flying lifestyle indicates that business income hasn't been reported, in most cases. 

In , a bankruptcy matter, the Hawkins family lived a "truly exceptional" lifestyle, while claiming they were bankrupt. The 9th Circuit Court and the California Franchise Tax Board determined that "maintenance of a rich lifestyle after their living expenses exceeded their income constituted a willful attempt to evade taxes." 

Any business can make a legitimate mistake. But remember that ignorance of the law is now excuse. A business owner has an obligation to know - and abide by - the law, or face the consequences. 

Any person who willfully attempts in any manner to evade or defeat any tax imposed by this title or the payment thereof shall, in addition to other penalties provided by law, be guilty of a felony and, upon conviction thereof, shall be fined not more than $100,000 ($500,000 in the case of a corporation), or imprisoned not more than 5 years, or both, together with the costs of prosecution.  

Other fines and penalties are imposed for willful acts, such as 

  • Failure to collect or pay tax
  • Willful failure to file a return
  • Fraud and false statements (you must sign your tax return, attesting that all statements in that return are true)

    If acts are deemed to be "willful," the court may deem these acts as felonies or misdemeanors, and may result in heavy fines and imprisonment. 


    Disclaimer: The information in this article is for general purposes only, and there is no claim that the information is tax or legal advice. Each business is unique and tax laws and regulations are always changing. Consult your tax and legal advisors before you make a business decision that could affect your tax or legal situation.