Meet the Influencer Who Paid to Catch a Pass from an NFL Legend (and Actually Caught It)
A self-described social media influencer recently learned the hard way that the Tax Court doesn’t care how many celebrities you’ve met. The taxpayer worked a full-time IT job at a major airline, ran an unlicensed transportation service on the side, and sold hard-to-get event tickets. Over a three-year period, he went on a celebrity-meeting spree, paying for exclusive experiences at award shows, meet-and-greets with movie stars, and one-on-one time with sports legends. He deducted the costs first as charitable contributions, and later when that didn’t work, as marketing expenses for his influencer business.
The IRS disagreed with both characterizations. The Tax Court sided with the government.
The celebrity encounters read like a bucket list with receipts. He paid thousands for tickets to major award shows. He paid thousands more to meet various A-list movie stars. He shelled out a hefty sum for a personalized video message from a beloved superhero actor. He bought signed memorabilia from a basketball legend’s final season. He even entered lotteries for a chance to walk the red carpet with another superhero actor.
The athletic experiences were where things got entertaining. He paid to catch a pass from one NFL quarterback, and fumbled it. He paid to catch a pass from another NFL quarterback, and actually caught it. He paid to return a serve from a tennis icon who, in the taxpayer’s own words, “basically destroyed me” and told him he needed nine years of practice before trying again. He also paid for a training session and lunch with a famous mixed martial artist.
To his credit, he posted all of this to social media, including the embarrassing moments. The Court noted that despite the fumbled pass and the tennis demolition, these experiences “still created stories and personal prestige.” The opinion also observed that while the taxpayer supported a rival football team and was therefore “no fan” of the quarterback whose pass he dropped, the judges “were still left with the impression that he enjoyed interacting with him.”
His business setup was creative. He ran a transportation service using luxury vehicles with black exteriors and black leather interiors, generating six figures in annual gross receipts. He avoided taxi licensing requirements by only driving people he personally knew. He maintained four cell phones; one for transportation, one exclusively for social media so he wouldn’t get distracted, and two backups on different carriers to guarantee service at various stadiums. The Court allowed him to deduct a quarter of his phone expenses, reasoning that at least one of the four was probably for business.
His recordkeeping told two different stories. On one hand, he kept meticulous carbon-copy vouchers for every driving trip. On the other hand, he maintained no actual books, used no accounting software, and prepared his own taxes. All of this despite holding two accounting degrees and having worked at a Big Four firm early in his career. His method for separating business from personal expenses? Anything under fifty dollars was automatically counted as personal, whether it actually was or not.
The Court rejected his marketing expense argument. “These are desirable things,” the judge wrote of the award show tickets and celebrity meet-and-greets. “Witness the high prices they commanded.” The opinion noted that he didn’t initially claim these as business expenses and that he “likely derived considerable personal status from these brushings with the famous.”
He argued that the celebrity interactions boosted his social media following, which eventually led to advertising revenue. The Court’s response was direct: if that standard applied, countless personal expenses would suddenly become deductible, “such as a comedian getting good material for her standup act while on a European vacation.”
The Court did allow some deductions. His car and truck expenses were approved at eighty percent of claimed amounts since he kept those detailed trip vouchers. His credit card processing fees were fully deductible. His qualified business income deduction was reinstated because his transportation and ticket-reselling businesses were legitimate.
But the celebrity meet-and-greets, the signed memorabilia, the award show tickets, and the athletic experiences? All disallowed.
The penalties stuck too. Despite his accounting background, he kept no books and his records were inadequate. The Court found no reasonable cause defense available to someone with two accounting degrees who should have known better. He now owes a combined six-figure sum in deficiencies and penalties.
The takeaway is simple. If you’re going to pay big money to meet celebrities and call it a business expense, you need more than social media posts to prove it. You need records, a clear business purpose, and evidence that you weren’t just having the time of your life.