9 Wild Things People Claimed as Business Expenses — And What Actually Counts

Tax season has a way of turning everyone into a financial philosopher. Bare ideas start to bubble up somewhere between the receipts and the regret. Can you write off your dog? What about that wine tasting in Napa that “inspired” your next business idea? In theory, anything can be a business expense — if you're willing to explain it with a straight face and possibly face consequences. But in reality? The IRS has limits and will be a lot less amused than you think.

Let's take a look at nine wild things people have tried writing off and also get a reality check on what counts when you're trying to stay on the right side of the tax man.

One entrepreneur tried to claim their extravagant destination wedding as a promotional event for their business. The logic? They posted about it on the company’s social media, and clients were invited. While that may have racked up likes, it didn't win any love from the IRS. Personal expenses, even if they accidentally involve networking or Instagram-worthy moments, usually don’t fly.

What counts is something tied to a business purpose — like hosting a legitimate client appreciation event or brand launch. You're probably not getting a tax break when romance is the main reason.

Someone once tried to deduct all their dog’s expenses by calling the pooch a “security measure” for their home office. Cute idea, but unless your pup is a professionally trained guard dog for a business in a designated commercial zone, Fido’s kibble is coming out of your pocket.

In specific circumstances, animal expenses are allowed — like a working farm animal or a trained service dog with paperwork. But for most small businesses? Your furry friend’s snack budget isn’t cutting.

It might sound like the ultimate commitment to your brand, but getting inked doesn’t open the door to a tax write-off. One small business owner reportedly tried to expense a large tattoo of their logo as a marketing cost. The IRS didn’t see it that way.

Marketing expenses qualify for things like digital ads, business cards, signage, or promotional materials. But permanent body art? Not so much. No tax on tips might apply in a restaurant, but not when you’re tipping your tattoo artist and trying to sneak it into a 1099.

A real estate agent tried to deduct every single clothing purchase, including their stylist’s fee, under the claim that dressing well helped them land deals. Here’s the issue: The IRS generally doesn’t allow deductions for clothing that can be worn outside of work. So unless you’re buying a branded uniform or costume for a performance, your shopping haul is on you.

But here's where it gets more interesting: behind-the-scenes financial moves, like getting outsourced CFO services, can count — especially when working with professionals who know the line between personal and business. Firms like TGG-Accounting.com have helped companies clean up their books and get serious about brilliant, legitimate deductions. It's not as flashy as a new wardrobe but much more defendable.

Yes, someone tried this. Their reasoning? They ran a physically demanding landscaping business and claimed the hot tub helped their muscles recover after work. While medical expenses can be deductible sometimes, claiming a hot tub under your LLC is a serious stretch.

There may be a case if your doctor prescribes medical equipment only used for a health condition. But if your family and friends enjoy the same bubbly jets on the weekend, it probably won't pass inspection.

Enter the world of high-rollers who think floating around on a 50-foot boat qualifies as business networking. Someone once tried to write off their entire yacht as a client entertainment expense. While entertaining clients can be legitimate in some contexts, it has to meet very strict rules — and it definitely can't be primarily for personal use.

Even if you do hold a meeting on a boat, you’d need detailed records showing who was there, what was discussed, and how it was directly tied to business. And still, you’d likely only get to deduct part of the cost — not the whole luxury liner.

This one came from a startup founder who hired a personal chef to cook healthy meals at home and tried to claim it under employee benefits. While team wellness programs can sometimes be deductible, this one was a swing and a miss.

To qualify, a meal benefit has to be for the employer's convenience and available to all staff. Feeding yourself kale from your home kitchen isn’t a group perk.

Someone decided their leased luxury sports car was a necessary tool for impressing clients. That alone won’t cut it. Vehicles can be deducted under certain conditions, but they must be used primarily for business. Personal use has to be accounted for, and mileage needs to be tracked.

If you’re serious about writing off a car, keep detailed logs. The IRS likes receipts, not assumptions. A flashy car isn’t enough; you have to prove it earned its keep.

Renting a cabin in the woods to “brainstorm” with your business partner sounds idyllic, but that doesn’t automatically make it deductible. If no formal meeting agenda exists and the trip looks more like a weekend getaway, the IRS will view it that way.

Travel expenses can qualify, but only when the trip is genuinely for work. That means lodging, food, and transportation tied to a real business purpose, not just your desire to work from a hot tub with a view.

There's a fine line between creative and careless, and while some business expenses are totally legit, others are wishful thinking in receipt form. If it looks personal, feels personal, and benefits you more than your business, there’s a good chance it doesn’t belong on your tax return.