Tech Trouble and Taxation Tales The Story of Dillon and His Infamous Receipts

Welcome back to “Who, Me?”—the only certainties in life are death, taxes … and tech causing trouble. Today, we meet Dillon, a point-of-sale specialist at his hometown’s swankiest retailer, a place with a rooftop steakhouse, piano player, and bar. When local sports moguls threatened to leave town unless the city built a new stadium, the city council obliged—and slapped on four new taxes: extra sales tax, restaurant tax, liquor tax, and a double tax on live-entertainment nights. “The only items remaining untaxed in our restaurant were the napkins,” Dillon laughs. His POS system supported just four tax categories, so each tax got its own line, ensuring every receipt looked like a tax manifesto. Diners saw their steak, their wine, and then four lines of city-collected cash to fund the stadium. Compliance was airtight, and customers were definitely informed. But soon the city changed the rule, demanding “sales taxes on all receipts be printed as a single amount, rather than itemizing different aspects of poor governance.” Did Dillon’s epic receipts drive that change? We’ll never know—and Dillon sailed through blowback. That’s tech trouble for you.
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