The 5 Most Outrageous Things People Have Expensed for Work


Have you ever wondered what the most outrageously good business write-offs are?

If so, you’re not alone. 

So we decided to compile a list of some of the wildest tax write-off facts we’ve found.

Some of these are actually somewhat practical—while some are just purely nonsensical. 

Here’s what you need to know about some of the most outrageous tax write-offs that have been expensed for work.  

1. Advertising And Promotion

Have you ever wondered how some businesses can afford to spend so much on their business advertising?

Well, as it turns out—advertising tax write-offs can be pretty darn outrageous, seeing as how they’re 100% deductible

In other words—you could literally hire someone to design all of your marketing materials, create a marketing plan, and then orchestrate that plan—and write off all of it. 

Pretty wild stuff! 

2. Side Businesses Of The Ultra Rich

According to, the ultra-wealthy often write off losses from hobbies and side businesses to avoid paying income tax—sometimes for decades at a time. 

And honestly, some of these write-offs are pretty exorbitant. 

For example—horse racing is a particularly ‘lucrative’ side hustle to ‘lose’ in, apparently, as far as taxes are concerned. 

One wealthy businessman was able to write off $189 million in losses for his ‘horse racing business/hobby’ over the course of a 16-year period. 

That’s a pretty serious write-off—and it’s totally legal, even if it is a bit on the outrageous side! 

3. Business Losses In General

According to a New York Times article that was published back in 2020, Donald Trump once claimed (and received) a $72.9 million tax refund after declaring ‘huge losses’ across various business dealings. 

The claim landed him in an audit battle with the IRS that, apparently, has been going on for about a decade. 

If there’s one thing that history can teach us, it is that the ultra-rich—usually equipped with a team of expert financial gurus and accountants, are generally pretty good at not allowing their money to become ‘taxable’ revenue. 

And outrageous write-offs like this really help to paint a solid picture of this in real life! 

4. Write Off Those Courses!

Hey, if you’re a social media influencer who’s trying to ‘learn the ropes’ of online marketing—did you know that you can write off all kinds of stuff—from travel-related expenses, to tax advice, to incidentals, to office expenses, and even your phone and internet bill?

But one interesting thing that a lot of influencers overlook is that they can also write off business-related education. 

As it turns out—you can take courses until your eyeballs feel like they’re going to fall out of your head. Then, you can take all of those big course ‘bills,’ and write them off on your taxes. 

You can also do this with business-related books. 

If you travel to another location to take courses for business reasons, you can even write off those transportation costs! 

This will only qualify as outrageous if you do the math and maximize your opportunity for learning by offsetting your tax bill. 

Just make sure not to overshoot it. For best results, get a CPA to help you hammer out those numbers. 

5. You Can Write Off A Car—Kind Of

Well—this is actually only partly true. 

According to the new tax rules, if you purchase a new vehicle for your small business, you can write off some of the cost from your gross income. 

The rules for this are a bit complicated. As it turns out, you can’t really just straight up get a ‘car for free’ by writing it off. 

But you can deduct quite a bit of car-related business expenses from your taxes—and you can also deduct depreciation.  

With that being said, you can sometimes use Section 179 to get big-time write-offs on ‘heavy’ vehicles. So if your corporation needs a new SUV, pickup, or van—then this could actually add up to some pretty serious write-off tax power! 

It can, in fact, get pretty outrageous if your company buys and operates a lot of vehicles. 


Now you know about some of the most outrageous business expenses that people tend to write off on their taxes. 

Some of those tax laws are actually pretty wild! But it’s good for business!