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Happy Tuesday! Welcome to July. Fireworks are over, the grill is cooling down, and the IRS is still open for business. This week we’ve got a deduction that might apply to your car payment, a retirement penalty that catches people every year, a write-off window for business equipment that’s wider than it’s ever been, and a rapper who treated his tax bill like a suggestion. Let’s get to it.
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🚗 The car loan deduction most people don’t know to check
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⏰ The 25% retirement penalty hiding in plain sight
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🛒 The 2025 equipment write-off glow-up
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🎤 Lil Wayne owed the IRS $12 million. It took a plea deal to sort it out.
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Filing Made Simple
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🚗 The car loan deduction most people don’t know to check
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The Quick & Bristly: Schedule 1-A is the new 2025 IRS form for four OBBBA below-the-line deductions: no tax on tips (up to $25,000), no tax on overtime (up to $12,500 single/$25,000 joint), auto loan interest (up to $10,000), and the Senior Bonus Deduction ($6,000 per qualifying person). All four are available whether you itemize or not and run 2025 through 2028. If you bought a new car in 2025, check your VIN at nhtsa.gov. U.S. final assembly, not brand, determines eligibility.
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For the first time since the 1980s, personal auto loan interest is deductible on your federal taxes. The One Big Beautiful Bill Act brought it back for 2025, up to $10,000 in interest paid on a qualifying new vehicle loan.
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Most people assume they don’t qualify. Some of them are wrong.
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The vehicle must have been finally assembled in the United States. Not designed in the U.S., not branded as American, actually assembled here. And the way you verify it is by entering your VIN into the NHTSA VIN Decoder. The result tells you exactly where final assembly happened.
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Why does this matter? Because plenty of vehicles from Toyota, Honda and Hyundai have U.S. final assembly and qualify. And plenty of vehicles from U.S.-branded manufacturers don’t. A Toyota Camry built in Kentucky qualifies. A Ford Mustang assembled in Michigan qualifies. A BMW X5 assembled in South Carolina qualifies. A Chevrolet Blazer assembled in Mexico doesn’t. The brand is irrelevant. The VIN is everything.
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The other requirements: the vehicle must be new (no prior owners), bought with a purchase loan (not a lease), and primarily for personal use. The loan must have originated after Dec. 31, 2024, but the deduction itself isn’t a one-time thing. It runs every tax year from 2025 through 2028, so if you financed your car in 2025, you can keep deducting the interest you pay in 2026, 2027, and 2028 too, as long as you’re still under the income limits. The deduction phases out above $100,000 MAGI for single filers and $200,000 for married filing jointly.
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This deduction is claimed on Schedule 1-A, the new IRS form for all four OBBBA below-the-line deductions. It flows into Schedule 1 and then your 1040. If you’re using tax software, confirm it has the current Schedule 1-A. The IRS published the final form just weeks before the April 15 deadline, and some software was slow to update.
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If you bought a new car in 2025 and financed it, check your VIN before you assume you’re out. Five minutes of your time could be worth a meaningful deduction.
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👉 Find out if your car qualifies
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PRESENTED BY INSURIFY
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Are you paying too much for your car insurance?
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Insurance rates have climbed, and if you haven’t compared recently, there’s a good chance you’re overpaying. Insurify lets you see real quotes from top carriers in minutes, so you know exactly where you stand.
Just enter your car make and ZIP code to instantly pull up rates side by side. No phone calls, no agents, no fees — just a fast, clear look at what’s available in your area.
Drivers are finding rates starting as low as $39/month. The only way to know is to look.
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👉 See how much you could save
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Six questions, pulled straight from this week’s issue. No studying, no spreadsheet, no idea why you suddenly remember the standard mileage rate at parties now. Whoever racks up the most right answers earns a spot on the leaderboard and the right to be insufferable about it.
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Click below, to get started. If you haven’t played before, you’ll need to enter some basic info that is only used for the quiz. Good luck, and may the tax knowledge be ever in your favor.
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👉 Take the quiz →
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Personal Finance
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⏰ The 25% retirement penalty hiding in plain sight
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Image from Envato
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The Quick & Bristly: Required minimum distributions are the IRS’s mechanism for collecting the taxes it deferred while your retirement savings grew. Starting at age 73 (or 75 if born in 1960 or later), you must withdraw a calculated minimum from most tax-deferred accounts every year. Miss one and the penalty is 25% of the amount you should have withdrawn. SECURE 2.0 reduced it from 50%, which is better in the way that a smaller fine is still a fine.
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A required minimum distribution, or RMD, is the amount the IRS makes you withdraw from tax-deferred retirement accounts (traditional IRAs, 401(k)s, 403(b)s, and similar) once you hit a certain age. The reasoning is straightforward, if a little undignified: the government let you defer tax on that money for 40years, and now it would like its share, please, and is no longer willing to wait politely for you to die.
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RMDs begin at age 73 for anyone born between 1951 and 1959, and at 75 for anyone born in 1960 or later. Your first RMD has an extended deadline of April 1 of the year after you turn 73, but every RMD after that is due December 31.
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Say you turn 73 in 2026. You can wait until April 1, 2027 to take your first RMD, but your second one is still due Dec. 31, 2027. Take advantage of that grace period and you’ve stacked two taxable distributions into a single calendar year, which can push you into a higher bracket, increase the taxable portion of your Social Security, and trigger higher Medicare premiums via IRMAA, all in one festive twelve-month spree.
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The amount itself is calculated by dividing your prior year-end account balance by an IRS life expectancy factor. For most 73-year-olds, that works out to roughly 3.7% of the account balance per year, a number that grows as a percentage as you age, by design.
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The SECURE 2.0 Act reduced the penalty for missing an RMD from 50% to 25%, and to 10% if you catch and correct the mistake within two years. On a $20,000 missed RMD, 25% is $5,000, on top of the income tax you’ll owe when you eventually do take the distribution.
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The financial institution holding your account will often calculate the amount and send a reminder, but they are not responsible for making sure you actually withdraw it. That part is on you.
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👉 Are you required to take RMDs? Find out here
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Little Known RMD Strategy Allowed by the IRS
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For investors with $1M+ in retirement accounts, the tax code allows specific strategies that can reduce your tax exposure once RMDs begin—but only if used before then.
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The window is open for anyone within ten years of 73. A fiduciary advisor can review which may apply, at no cost.
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Get Matched Today
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Every Thursday, we go to work.
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The TaxStache Business Edition is built for owners and operators. Quick hits on entity structure, quarterly deadlines, deduction strategy and the IRS rule changes that actually affect your bottom line. Plus a weekly download you can put to use the same afternoon.
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If you run a business (or you’re building one), Thursday is definitely your day.
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Would you like to receive our Thursday Business Edition?
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Celeb Tax Cases
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🎤 Lil Wayne owed the IRS $12 million. It took a plea deal to sort it out.
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Image by Andres M.
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The Quick and Bristly: Rapper Lil Wayne pled guilty in 2020 to a federal gun charge, but his tax troubles told a bigger story. He faced multiple IRS liens totaling roughly $12 million in unpaid federal taxes over several years, including a $5.6 million lien in 2011 and additional liens that followed. His situation is a case study in what happens when high earners treat tax obligations as optional.
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Dwayne Michael Carter Jr. — better known as Lil Wayne — has sold over 120 million records worldwide, won five Grammy Awards, and built a career that spans three decades. He has also spent a significant portion of that career owing the IRS money he earned but apparently forgot to share with the federal government.
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The IRS came after Wayne in 2008 for about $1 million. He paid it. Then, in 2010 and 2011, they came back: $1.1 million for 2004 through 2007, plus a fresh $5.6 million for 2008 and 2009. He paid those too, eventually.
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Then 2014 happened. Two more liens, for 2011 and 2012, added up to just over $12 million on their own.
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Wayne’s situation is a textbook example of what tax professionals call a “snowball” problem. Miss one year, and it gets harder and harder to get caught up. Miss it again a few years later, and you’re not looking at one bill anymore, you’re looking at four.
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For high earners with variable income — which describes every touring musician, actor, and athlete — the quarterly estimated tax system is the make-or-break mechanism. You don’t get a W-2 with withholding. You’re responsible for calculating and paying taxes four times a year. Skip that process, and the IRS doesn’t send a polite reminder. It sends a bill with interest, followed by a lien that attaches to everything you own.
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Lil Wayne eventually resolved his debts, as most celebrity tax cases do, because the IRS would prefer to collect than to prosecute. But four liens spread across six years, and the interest that piled up on each one, was a deeply expensive form of procrastination.
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The IRS doesn’t care how many Grammys you have. It cares whether your 1040-ES arrived on time.
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The quick (and slightly prickly) stories we didn’t have time to get to:
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If you made it this far, you’re our kind of nerd. Hit reply and tell us which story you want us to dive deeper into next week.
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Follow us for even more great tips, tricks, and deadline reminders. Facebook | Instagram | LinkedIn
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