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Client: Can I write off my Ferrari?
Tax Pro: UMMM do you have a Ferrari?
Client: I have an LLC.
Tax Pro: That’s not what I asked.
Client: …okay how can I deduct a Ferrari?
Tax Pro: so we have to ask first ‘is this for a trade or business’. “Trade or business” is mentioned 800 times in the tax code. You know how many times it’s actually defined?
Client: A lot?
Tax Pro: Zero. So we go to case law. Specifically a Supreme Court case about a full-time dog track gambler named Groetzinger.
Client: Can I get this action on Kalshi?
Tax Pro: sigh, okay this guy had no other job. Showed up to the dog tracks every single day, tried to make money gambling on dogs. IRS said he wasn’t running a business. Groetzinger said “takes two to gamble.”
Client: Who won?
Tax Pro: Groetzinger. Courts ruled that an activity must be conducted with continuity, regularity, and primarily for profit to qualify as a trade or business. He showed up every day trying to make money. That was enough.
Client: Okay so I show up to work every day, I definitely have a trade or business.
Tax Pro: Good. But that’s just hurdle one. Now we have to talk about whether the Ferrari expense is “ordinary and necessary.”
Client: Ordinary meaning what?
Tax Pro: Common and customary for your type of business. This is where it gets interesting. Take the Dancer case versus the Gillam case.
Client: Never heard of either.
Tax Pro: Dancer traveled for work, got into a car accident, tried to deduct the negligence claim as a business expense because he was traveling for work when it happened.
Client: Did it work?
Tax Pro: Yes. Travel is ordinary for his business, the accident happened in the course of that travel, so it was ordinary.
Client: Okay that makes sense.
Tax Pro: Now Gillam. Also traveling for work. Also tried to deduct something that happened during work travel.
Client: Also worked?
Tax Pro: Gillam assaulted someone on the plane.
Client: Maybe it was ‘necesssary’
Tax Pro: Tax court said assaulting people is not ordinary conduct for your business. Probably. Unless
Client: Okay okay. So ordinary means normal for your industry. No Ferrari then. What’s “necessary” mean?
Tax Pro: Helpful and appropriate to the business. And this is where people really get themselves in trouble. Take the case of Robert Lee Henry.
Client: Who’s that?
Tax Pro: A CPA. Owned a yacht. Flew a flag off the back of it that just said “1040.”
Client: …that’s incredible.
Tax Pro: He thought so too. Tried to deduct every yacht expense because hey — the flag says 1040, it’s obviously for the tax business.
Client: Did it work?
Tax Pro: Tax court looked at him and said show us how this yacht is necessary to the conduct of your profession. Not helpful. Not good for vibes. Necessary.
Client: And he couldn’t?
Tax Pro: He could not. The flag said 1040. The boat said pleasure craft.
Client: Okay okay so no Ferrari.
Tax Pro: No to the Ferrari.
Client: but a truck, its ordinary for my industry, I use it for client meetings, and it protects my brand image.
Tax Pro: Is driving a truck to client meetings common and customary in your industry?
Client: Well yeah I’ll ust it help carry supplies to the property and stuff
Tax Pro: Alright that works out then
Client: Can it be… a nice truck? Ooh wait can I use this 179 thing on it?
Tax Pro: I mean also yes… but we have to talk about other rules there
Client: *dials phone Hey Jim, yeah Im coming to your dealership right now to buy that Ford Raptor… Yeah I dont have cash so can we finance that…
Tax Pro: *sighs*
2024 FCS Champion: NDSU
2025 playoffs: eliminated in second round after first round bye
2024 FBS Champion: Ohio State
2025 playoffs: eliminated in second round after first round bye