2/17/26 Newsletter

Making money is a hobby; keeping it away from the IRS is a full-time job. Let’s get to work.

This week’s lineup:

• 🚗 Log your miles to save thousands on your 2025 and 2026 taxes.

• ❤️ Supporting an elderly parent in 2026 offers more red tape than refunds.

• 🚪 Learn how to turn the 15.3% self-employment tax into a secret superpower.

• 🎸 Chuck Berry’s "brown paper bag" cash policy led him straight to a jail cell.

Filing 101

🚗 Log Your Miles to Save Thousands on Your Taxes

In the glove compartment of every small business owner, freelancer, and gig worker, there lives a creature of immense financial power, often disguised as a cheap, spiral-bound notebook with a coffee stain on the cover.

This is the humble mileage log.

It’s the thing we all mean to keep up with, like flossing or finally cleaning out the gutters, but often forget until the cold sweat of tax season sets in.

But this tedious little chore is one of the most lucrative habits a taxpayer can develop. It’s a diary for your car that could be worth thousands of dollars.

What the IRS Actually Demands to See

When it comes to your car expenses, the IRS doesn't just want a number plucked from thin air. They want a story, a logbook, a captain’s report of your daring journey to the office supply store.

For 2025, every single business mile you drive is worth a cool 70 cents as a tax deduction. Those miles add up fast, but you have to prove them.

Here’s what your car’s diary needs to include for every business trip:

• The Date: Simple enough. When did you go?

• Your Destination: Where did you drive to?

• The Business Purpose: This is key. "Meeting with Bob" is okay, but "Meeting with Bob to discuss the Q3 widget contract" is a masterpiece.

• The Mileage: The best way to track this is with your starting and ending odometer readings for each trip.

Remember, your daily drive from your pillow to your primary office is considered commuting. And alas, the IRS says that’s on you. Those miles aren’t deductible.

The Great Debate: Paper Scribbles vs. Digital Overlords

Every taxpayer must choose their weapon in the battle for deductions.

The Old-Fashioned Way: A Trusty, Stained Notebook

The classic method. It's cheap, it doesn't need batteries, and it works. The downside? It relies on you having the memory of a supercomputer and the discipline of a drill sergeant to remember to write it down every single time.

The Modern Miracle: Letting an App Do the Hard Work

Welcome to the future. GPS-powered mileage apps, such as MileIQ and TripLog, track your every move automatically. At the end of the day, you just swipe left for personal trips and right for business. It makes the whole process ridiculously easy and removes the "I forgot" excuse from your arsenal.

We’ll show you exactly how to use your old emails and calendars to reclaim the thousands of dollars you’re entitled to for 2025 and 2026. Keep reading →

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Money Moves

❤️ The 2026 Tax Rules for Caring for Elderly Parent

If you’re part of the “Sandwich Generation,” you’re paying for Montessori tuition and your mother’s hearing aids at the same time. You’re tired. Your budget is tired. And while the IRS loves children, they treat elderly parents like suspicious carry-on luggage: tolerated, but heavily examined.

The 2025 One Big Beautiful Bill Act (OBBBA) handed out generous new deductions to some taxpayers. Caregivers, though, didn’t get confetti. They got conditions. Claiming a parent won’t make you rich. At best, it gets you $500, slowly.

The Qualifying Relative Rules

Before you claim anything, your parent must pass the “Qualifying Relative” rules, which feel like a test designed for you to fail.

1. The Gross Income Cap

For 2025, your parent generally can’t earn more than $5,200 in gross income. Examples:

• Mom earns $5,300 selling knitted tea cozies on Etsy: no credit for you.

• Social Security usually doesn’t count.

• But other income (interest, dividends) can make part of Social Security taxable, which can push them over the limit.

2. The Support Test

You must provide more than half of their total support for the year. Support includes:

• Housing (fair market value of the room)

• Food

• Utilities

• Medical expenses

• Everyday living costs

If they live in your home rent-free, you likely pass. If they live in a condo in Boca Raton and you only pay the cable bill, you don’t.

The “Reward”: A Credit Too Small to Celebrate

If you pass every hoop, you get the $500 Credit for Other Dependents (ODC).

That’s it.

The Child Tax Credit offers up to $2,000, meaning teenagers are apparently four times more valuable than aging parents. And to top it off, the ODC begins to phase out once your income exceeds $200,000, if you’re filing single.

Ready to turn those heavy caregiving costs into actual savings? We’ll show you how to stack the new $6,000 senior deduction with your own filing status to maximize your 2026 refund. Keep reading →

Business & Gigs

🚪 Self-Employment Tax: A Wall or a Door?

Most freelancers see the 15.3 percent self-employment tax, wince, and write the check. Just another price of being your own boss.

But some freelancers see that same number and spot an opportunity. They've learned that the tax code isn't a wall. It's a door. And if you know where to push, you can turn a painful liability into a strategic advantage.

Meet the Villain in a Beige Suit

If the tax code were a movie, the self-employment tax wouldn't be the cackling supervillain. It would be the boring middle-management type in an off-the-rack suit, armed with paperwork and a mission to complicate your life.

His name is FICA (Federal Insurance Contributions Act), and for regular employees, he's just a familiar pest — a chunk of every paycheck vanishing to fund Social Security and Medicare.

But when you go freelance, you discover something unsettling. You have to pay both sides: the employee's share AND the employer's share.

Now this boring villain looks genuinely menacing. He's demanding 15.3 percent of your profit. His master plan isn't world domination, just making you feel like you took a 15.3 percent pay cut for the crime of working for yourself.

The Shocking Plot Twist

But here's what the insiders know: this villain isn't actually a villain.

He's a superhero in disguise.

Buried in the tax code is his secret identity. The self-employment tax has a hidden superpower: it can lower your other, much bigger tax bill — your income tax.

Sounds like a trick, right? Like the IRS mugging you and then leaving a mint on your pillow. But it's real. The self-employment tax you pay isn't just a cost, it's a key that unlocks one of your most powerful deductions.

See exactly how the “deduction for one-half of self-employment tax” puts cash back in your pocket. Keep reading →

 🤝 Build Your Future: Insights from the Franchise Front Lines

Dreaming of owning a franchise but not sure where to start? The Great American Franchise Expo is touring 10 cities this year to help you find the answers.

This is your chance to step into a room full of experts and like-minded future owners. Instead of just browsing online, you can have face-to-face conversations with brands in fitness, tech, home services, and more. Attend free seminars on everything from understanding legal documents (FDDs) to securing SBA loans and alternative financing.

The Best Part? Your admission is FREE with online registration (normally $29 at the door).

See the full 2026 tour schedule and grab your free pass here!

Wild Tax Tales

🎸 No Cash, No Show, No Taxes: The Chuck Berry Method

Chuck Berry invented the duck walk, but he also pioneered a less celebrated move: the brown paper bag handoff.

By the 1970s, the father of rock ‘n’ roll had stopped trusting promoters. He stopped trusting banks. He certainly didn’t trust the government. His rider was simple: he played with a local pickup band (who he never rehearsed with), he drove his own rental car to the gig, and he demanded his fee (often $20,000 or more) in cold, hard cash before he plucked a single string.

Usually, this cash came in a literal brown paper bag. If the bag wasn't there, or if the count was short by a single bill, the crowd waited.

The IRS, however, is immune to rock star charisma. They noticed that Berry’s lifestyle didn’t quite match the income reported on his 1040s. The math was impossibly lopsided. In 1979, the taxman finally caught up with the “Johnny B. Goode” singer. The charge wasn't just sloppy bookkeeping; it was deliberate evasion. He had ghosted the government on nearly $110,000 in income taxes for 1973 alone.

Berry pleaded guilty. The judge, unimpressed by Berry’s contribution to American culture, sentenced him to four months in federal prison and 1,000 hours of community service.

But the lesson didn't entirely stick, and his legal troubles shifted from the IRS to the local police. In 1990, authorities raided his estate and a nearby restaurant he owned after several former employees sued him. They claimed Berry had installed secret cameras in the women's restrooms. During the search, investigators found stacks of cash, bags of marijuana, and a collection of homemade tapes showing various women using the bathroom without their knowledge.

While the drug charges were eventually dropped, the (incredibly creepy) videos cost him over $1 million in settlements to dozens of women. For Berry, the privacy of a brown paper bag only seemed to apply to his own interests.

The quick (and slightly prickly) stories we didn’t have time to get to:

• 🪙 IRS taxes gold and silver identically as collectibles.

• ⚖️ Judge blocks ICE from using IRS taxpayer data.

• ⏰ IRS staffing cuts and backlogs may delay refunds.

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.