Crazy Tax Deductions

Crazy Tax Deductions

Every year at tax time, people try to come up with items to deduct or write off on their tax return. Sometimes the IRS allows them, and sometimes they don’t. We’ve compiled a list of our favorite crazy tax deductions, some were successful and others were not.

Crazy Tax Deductions that the IRS Allowed:

  • Parents put their child in clarinet lessons and argued that it would correct the child’s overbite. The IRS agreed and allowed them to deduct the cost of the lessons.
  • One gentleman used an Amish buggy for business purposes. He pimped it out with velvet interior, special headlights, etc. He used it to drive his clients around town and the IRS allowed him to deduct the cost of the upgrades.
  • An ostrich breeder in Florida was able to write off the cost of the animal as a depreciation business expense.
  • A professional bodybuilder was able to write off the cost of body oil as a business expense.
  • A couple hired a babysitter so they could do charitable work. They were able to deduct the babysitting fees on their tax return.
  • One gas station owner decided to offer free beer to customers. He was able to argue, and the IRS agreed, that it could be deducted as a business promotion expense.
  • A man was looking at rental property in the mountains, which was a 5-7 hour drive. In order to avoid the driving time, he purchased a private plane. He was allowed to deduct the cost of the plane as a normal, ordinary and necessary business expense.
  • Another couple was able to deduct the cost of cat food. They owned a junk yard and needed to attract wild cats to catch the rats and snakes.
  • One individual was advised by his doctor to swim frequently to help relieve severe arthritis. He built a new indoor pool and his condition improved. He claimed that it was a necessary and ordinary medical expense, based on a doctor’s request, and he was allowed to deduct the operating expenses of the pool.
  • Some Dairy Business owners went on an African safari to research wild dairy cows. They told the IRS that it was an ordinary and necessary business expense to improve the quality of their dairy products.

Crazy Tax Deductions that the IRS Denied:

  • One individual tried to write-off his home toilet paper supply.
  • A gentleman tried to write off his dog as a dependent. He even argued the expenses of doggy day care and the credit for child care expenses.
  • A woman wrote a $2,000 check for her gynecologist and tried to write it off as a business expense.
  • An Individual hired an arsonist to burn down his house. He collected a $500,000 insurance policy. He took the $10,000 that he paid the arsonist and tried to deduct it as a “consulting expense”.
  • One man bought mink coat for his wife and tried to write it off as an entertainment expense. He argued that it was a great conversation piece and part of the promotion cost of his business.
  • A business owner bought a race horse as an excuse to go to the races. He tried to write off all the transactions as a business expense.
    One lady took dance lessons to improve her varicose veins and tried to write-off the expense.
  • A ballerina failed at deducting the cost of her tummy tuck.
  • A piano player tried to deduct his manicures as a business expense.
  • A farmer tried to claim food and veterinary expenses for his toy poodle as a farm-building “guard dog”.
  • A woman attempted to deduct gambling losses as a charity donation.
  • One woman tried to write off the cost of her “Zumba” classes.

Although, many of these tax deductions failed, there are hundreds of other tax deductions that may be available to you. Contact us for help in preparing your tax return.

If you have questions or need expert tax or family office advice that’s refreshingly objective (we never sell investments), please contact us or visit our Family office page  or our website at  Unfortunately, we no longer give advice to other tax professionals gratis.

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Alan Olsen, CPA

Alan Olsen, is the Host of the American Dreams Show and the Managing Partner of  GROCO is a premier family office and tax advisory firm located in the San Francisco Bay area serving clients all over the world.


Alan L. Olsen, CPA, Wikipedia Bio is a proud sponsor of The American Dreams Show.



The American Dreams show was the brainchild of Alan Olsen, CPA, MBA. It was originally created to fill a specific need; often inexperienced entrepreneurs lacked basic information about raising capital and how to successfully start a business. Alan sincerely wanted to respond to the many requests from aspiring entrepreneurs asking for the information and introductions they needed. But he had to find a way to help in which his venture capital clients and friends would not mind.

The American Dreams show became the solution, first as a radio show and now with YouTube videos as well. Always respectful of interview guest’s time, he’s able to give access to individuals information and inspiration previously inaccessible to the first-time entrepreneurs who need it most. They can listen to venture capitalists and successful business people explain first-hand, how they got to where they are, how to start a company, how to overcome challenges, how they see the future evolving, opportunities, work-life balance and so much more..

American Dreams discusses many topics from some of the world’s most successful individuals about their secrets to life’s success. Topics from guest have included:

Creating purpose in life / Building a foundation for their life / Solving problems / Finding fulfillment through philanthropy and service / Becoming self-reliant / Enhancing effective leadership / Balancing family and work…

Untitled_Artwork copy 4 (Also sponsored by GROCO) provides free access to content and world-class entrepreneurs, influencers and thought leaders’ personal success stories. To help you find your path in life to true, sustainable success & happiness.  It’s mission statement:

In an increasingly complex and difficult world, we hope to help you find your personal path in life and build a strong foundation by learning how others found success and happiness. True and sustainable success and happiness are different for each one of us but possible, often despite significant challenges. Our mission at is to provide resources and firsthand accounts of how others found their paths in life, so you can do the same.

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