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The Fine Art of Getting Caught

October 14, 2025 by Bill Bourbonnais

When most people think of taxes, they think of income tax — the annual bloodletting every April that funds everything from fighter jets to the world’s slowest website redesigns. But there’s another tax that quietly siphons billions every year without nearly as much drama: sales tax.

Filed Under: taxes Tagged With: ArtScandal, FinancialStrategy, HighNetWorth, IRS, ResaleCertificate, SalesTax, Sothebys, StateTaxes, TaxAudit, TaxCompliance, TaxLoopholes, TaxStrategy

Buried Treasure and the IRS

October 7, 2025 by Bill Bourbonnais

Every kid dreams of finding a buried chest full of gold coins, a few emeralds, and maybe a wooden leg or two. But grown-ups who actually find treasure soon discover the real pirates aren’t the ones with eye patches and hooks. They’re the ones with ID badges reading “Internal Revenue Service.”

Filed Under: IRS, taxes Tagged With: CesariniCase, FinancialIrony, FoundWealth, IRSSalvage, OtherIncome, TaxLaw, TaxSmart, TaxStrategy, TreasureTroveTax

Uncle Sam Wants to Venmo You

October 1, 2025 by Bill Bourbonnais

Remember when getting a tax refund meant waiting by the mailbox like a kid on Christmas morning? Except, instead of a shiny new bike, you got a government-issued check printed on shiny iridescent paper? You’d spot that official envelope, rip it open with the excitement of opening your card from Grandma (with a crisp $20 bill inside), and admire the John Hancock of some Treasury bureaucrat who probably couldn’t get a table at Applebee’s without a reservation. Then you’d rush to the bank and stand in line behind a guy depositing coins in a jar. And of course, there was always the risk your ex would intercept it, or the family dog would decide it made the perfect chew toy. It was a ritual equal parts thrilling, frustrating, and absurdly outdated, like renting DVDs from Blockbuster or printing out MapQuest directions.

Filed Under: Uncategorized Tagged With: DirectDeposit, ElectronicPayments, FinancialIrony, IRSDigital, irsupdate, TaxRefunds, TaxSmart, TaxStrategy, Unbanked

From Campaign Slogan to Fine Print

September 23, 2025 by Bill Bourbonnais

Remember the “no tax on tips” promise? The IRS just issued proposed guidance spelling out which jobs actually qualify for the shiny new break under the Big Beautiful Bill. The list looks familiar — bartenders, servers, nail techs, taxi drivers – and it also includes roles like bussers, cooks, and dishwashers. That’s not because customers are tipping the dish pit directly, but because tip-sharing is a long-standing part of the industry.

Filed Under: One Big Beautiful Bill, taxes Tagged With: #BigBeautifulBill, #BusinessOwners, #IRSUpdate, #NoTaxOnTips, #RealEstateTaxPros, #RestaurantLife, #RideshareLife, #TaxBeat, #TaxDeduction, #TaxPlanning, #TaxStrategy

Guy Math: The Drill That Keeps on Giving

September 16, 2025 by Bill Bourbonnais

By now you’ve probably heard of “girl math.” That’s the playful financial logic that turns a return into a profit or makes anything bought with cash “basically free.” Pay for Taylor Swift tickets six months in advance? By the time the concert rolls around, they cost nothing. It’s not necessarily “wrong” math. It’s “emotional” math. It explains how money feels rather than how it flows. Accountants everywhere faint when they hear it, but they faint quietly — back into their spreadsheets where they feel comfortable.

Filed Under: IRS, Retirement, taxes Tagged With: businesstaxes, DIYFinance, EntrepreneurLife, FinancialHumor, GuyMath, IRSReality, SmallBusinessTips, TaxDeductions, TaxSmart, TaxStrategy, WriteOffWisdom

ChatGPT, Tax Planner

September 8, 2025 by Bill Bourbonnais

Remember when we thought robots were just coming for factory jobs, truck driving jobs, and maybe your nephew’s job at Taco Bell? Well, surprise: now they’re gunning for your tax pro. That’s right, the machines have been let loose on the U.S. tax code, and the results are equal parts brilliant, terrifying, and hilarious.

Filed Under: Artificial Intelligence, IRS, taxes Tagged With: AIandTaxes, AIAudit, AuditRisk, ChatGPTFinance, irsupdate, TaxAdvice, TaxLoopholes, taxplanning, TaxProTips, TaxStrategy

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