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Fetch is Not Going to Happen

December 31, 2025 by Bill Bourbonnais

This time of year, most tax pros are gearing up for yet another season preparing returns. But it looks like Tax Season 2026 might come with a new kind of tail-wagging drama. A New York attorney named Amanda Reynolds has taken a big bite out of the Internal Revenue Service, asking a federal court to […]

Filed Under: IRS, taxes Tagged With: AuditProof, CanineCourt, FinancialPlanning, GoldenRetriever, IRS, PetDeductions, SmallBusinessTax, TaxHumor, TaxStrategy, taxtips

Rounding Up and Cashing Out

November 18, 2025 by Bill Bourbonnais

Every so often, Uncle Sam announces something that makes taxpayers stop, blink, and ask, “Wait… we’re still doing that?” Now that conversation has landed squarely on the humble penny. Yes, the little copper-colored coin that costs more to make than it’s worth, that falls between couch cushions like it’s trying to escape the junk drawer, and that we all secretly wonder what to do with when we get it back as change. Last week, Treasury Secretary Scott Bessent personally minted the last five of their kind. And many Americans say this with love: it’s about time. You know inflation is bad when even money is worth less than the metal it’s made from.

Filed Under: IRS, taxes Tagged With: DigitalPayments, EndOfThePenny, FinancialPlanning, InflationInsights, IRS, MoneyMatters, PricingPsychology, SmallBusinessFinance, taxes, TaxStrategy

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

You Belong with Me (And The IRS)

September 2, 2025 by Bill Bourbonnais

The world has finally exhaled — Taylor Swift and Travis Kelce are officially engaged. Forget wars, politics, and inflation: this is the headline America needed. It’s like Shakespeare meets the Super Bowl, with a soundtrack already topping the charts. But here, we’re less concerned about the flowers, the venue, or whether Ed Sheeran sings at the reception. We’re laser-focused on two things the IRS cares about most: the ring and the prenup

Filed Under: IRS, taxes Tagged With: EngagementTax, GiftTax, HighNetWorth, IRS, PrenupPlanning, TaxStrategy, TaylorSwift, Tayvis, TravisKelce, WealthProtection

Houston, We Have No Taxes

August 19, 2025 by Bill Bourbonnais

You know how you sometimes hear about highflying companies sending miserly tax checks to Uncle Sam? Well, buckle up — SpaceX might just be the star of that show. According to a New York Times exposé, SpaceX has privately told investors that because of a 2017 tweak to the Tax Cuts and Jobs Act, it may never have to pay federal income tax, even if they do succeed in helping mankind colonize Mars.

Filed Under: tax cuts and jobs act, taxes, TCJA Tagged With: 2017TaxReform, BusinessFinance, CashFlow, EntrepreneurTips, IRS, LegalLoopholes, NetOperatingLoss, SmallBusinessFinance, SpaceX, TaxCode, taxplanning, TaxStrategy

The Devil’s in the Deductions-Digging Into the “Big Beautiful Bill”

July 8, 2025 by Bill Bourbonnais

You already know the highlights: the Big Beautiful Bill (BBB) is Congress’s latest effort to stuff 10 pounds of tax cuts into a five-pound bag. It locks in most of the 2017 Tax Cuts and Jobs Act. Marginal rates stay low. The standard deduction stays chunky. The qualified business income deduction lives to fight another day. Cue the confetti (and another round of Roth conversions while you’re at it).

Filed Under: taxes, TCJA Tagged With: 2025 tax law, Big Beautiful Bill, capital gains, gambling deductions, IRS, passive income, professional gambler, QSBS, startup taxes, Tax Cuts and Jobs Act, tax reform, tax savings, tax strategy, taxpolicy, taxrelief

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