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A Charlie Brown Tax-Giving

November 25, 2025 by Bill Bourbonnais

For most families, Thanksgiving means gathering around a perfectly roasted turkey, sharing gratitude, and trying to avoid discussing politics or crypto. But in A Charlie Brown Thanksgiving, things are a little more “improvised.” Instead of turkey and stuffing, the Peanuts gang ends up with toast, popcorn, pretzel sticks, and a side of existential confusion. And honestly? That makes it a pretty realistic holiday picture. Because whether you’re cooking a turkey or prepping a tax plan, life serves up whatever’s in the pantry. Charlie Brown’s holiday feast is basically a metaphor for the final weeks of tax-planning season. It’s messy, it’s chaotic, and half the participants assume someone else is doing the hard work. If that isn’t December tax planning, I don’t know what is.

Filed Under: Uncategorized Tagged With: business tax tips, December deductions, financial planning, IRS deadlines, last-minute taxes, small business tax, tax, tax planning, tax pro life, tax reduction, tax savings, tax strategy, taxes, year-end strategy

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

Bone to Pick: Travelers Howl Over Italy’s Dog Tax

November 12, 2025 by Bill Bourbonnais

If you ever thought vacationing with your dog was a walk in the park, Italy just tossed a new stick into the game. The Province of Bolzano in northern Italy is planning to charge visitors about €1.50 per day, or roughly two bucks, for the privilege of bringing along their pup. That’s right: tourists are choking on a brand-new “dog tax.” Sit. Stay. Pay.

Filed Under: taxes Tagged With: BolzanoNews, DogFriendlyTravel, FurBabiesAbroad, ItalyDogTax, PetTravelTips, tax, tax strategy, TaxHumor, taxpolicy, TouristFees, TravelTaxes

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

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

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