Five of the Craziest Tax Deductions

The interpretation of what’s an allowable deduction has increasingly pushed the limits of imagination. Certainly what’s considered to be a business expense has changed over the last 20 years.  What the IRS has allowed as deductions would make most people's heads spin but as long as it's legitimate, Uncle Sam will allow it. 

So if you think your expenses are simply too crazy to deduct on your return, you may or may not be right. Don't be afraid to consult your tax professional because they have probably already seen and heard it all. Whatever you do decide to claim, make sure it's legitimate and be ready to prove it if the IRS comes knocking on your door. 

Meisa Bonelli, Wall Street tax professional and business match-maker, is the President of Millennial Ventures and Managing Partner of Millennial Tax. She specializes in advising home-based business professionals, start-ups and solopreneurs throughout the United States on tax issues that can help propel their business growth. She may be reached online at


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