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TaxStrategy

When “Fair Share” Sounds Like “Find the Exit”

January 6, 2026 by Bill Bourbonnais

Raising taxes on the rich is usually a party trick politicians pull out when they want applause, not when they actually plan to do it. Lately, though, some of them are dusting it off again, and high earners are reacting the same way people do when the waiter raises an eyebrow and says, “So . […]

Filed Under: IRS, taxes Tagged With: BusinessPlanning, CaliforniaExit, FinancialStrategy, HighEarnerMoves, NYCTaxes, RelocationRisk, ResidencyRules, TaxSmart, TaxStrategy, WealthTax

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

Welcome to the Ozempic Economy

December 2, 2025 by Bill Bourbonnais

If you’ve noticed that Santa and his elves look a little slimmer this year, it’s not your imagination. Weight loss drugs like Ozempic, Wegovy, and Zepbound have become so popular that economists are now tracking what they call the Ozempic Economy. When a diabetes medication becomes a lifestyle trend powerful enough to move airline stocks, clothing companies, and grocery chains, you know something interesting is happening. And as always, there are tax angles hiding in all this too.

Filed Under: Uncategorized Tagged With: BusinessWellness, EmployeeBenefits, HSADeductions, IRSWatch, MedicalExpenses, OzempicEconomy, SmallBizTaxTips, TaxStrategy, WeightLossTax, WellnessEconomy

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

When TikTok Becomes TaxTok

November 5, 2025 by Bill Bourbonnais

Buckle up, buttercups — it’s time to talk about the avalanche of advice flooding Instagram, Facebook, TikTok and beyond. You know the kind: “Just buy a short-term rental and poof — zero tax!” It’s catchy. It’s viral. And it’s mostly hype. Sure, short-term rentals can offer tax advantages, maybe even significant ones. But the idea that you […]

Filed Under: IRS, taxes Tagged With: AuditRisk, BusinessAdvice, CredentialedAdvice, FinanceInfluencers, FinancialLiteracy, IRSCompliance, ShortTermRentalMyths, taxplanning, TaxStrategy, TaxTok

Fast, Furious, and Fair?

October 21, 2025 by Bill Bourbonnais

You know that sinking feeling. You’re driving down the road, minding your own business, when you see a cop’s “cherries and berries” flashing in your mirror. Then you look down at your speedometer and realize he’s gunning for you. Sure, it’s a bummer. But it’s not that big a deal. The gendarme checks your license, registration, and proof […]

Filed Under: IRS, taxes Tagged With: CaliforniaTaxes, FinlandFines, HighIncomeProblems, IncomePenalty, IRSWatch, SmartMoneyMoves, SpeedingTicket, TaxStrategy, TrafficFines, WealthPlanning

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