💸 He ditched the U.S. The IRS sent a $50M bill.

The countdown to turkey day has begun. While you’re prepping for leftovers, the IRS is quietly prepping your tax paperwork.

This week’s lineup:

Personal Finance

🛍️ The Black Friday Tax Hangover

There’s a particular, almost primal, satisfaction in navigating the chaos of Black Friday.

You’ve wrestled shopping carts, dodged sales people and pop-up ads like a seasoned matador, and emerged victorious with a confirmation email or a shiny, freshly printed receipt. You are a champion of commerce.

Then, a few days later, the credit card statement arrives. It glows with a malevolent digital light, and the numbers are somehow … different. That $800 laptop was somehow … more. That deeply discounted air fryer has an extra few dollars tacked onto it, like a tiny, uninvited barnacle.

Welcome to the Black Friday Tax Hangover.

This is that dreary, fluorescent-lit morning-after where you realize your shopping spree had a silent, and very thirsty, partner: the government.

Your Uninvited Shopping Buddy: Sales & Use Tax

Every time you click “Buy Now,” you’re essentially inviting your state’s department of revenue along for the ride. They don’t help you find the best deals, of course. They don’t offer moral support when the limited-edition sneakers sell out in 12 seconds. But when the bill comes, they’re right there with their hand out.

The point is, that 40 percent discount you were so proud of was probably closer to 33 percent once the taxman took his slice.

Want to know which Black Friday buys you can actually write off without getting side-eyed by the IRS? Keep reading →

Tax Strategies

🎁 A Cornucopia of Credits

The holiday season brings out a unique urge to declutter in many of us. Suddenly, our garages transform into spaces of opportunity. Our closets, packed with clothes we vowed to wear again, become unexpected treasure troves.

You’re not just cleaning; you’re preparing to bestow your gently-used possessions upon the less fortunate. And, if you play your cards right, you can also bestow a slightly smaller tax bill upon yourself.

This is the art of charitable giving, where your generosity and your enlightened self-interest can walk hand-in-hand.

The Easy Part: Giving Cold, Hard Cash

Donating money is straightforward, but the IRS, in its infinite love for paperwork, has a few thoughts on the matter.

First, choose wisely. Your donation must go to a qualified charitable organization. Your cousin’s GoFundMe to start an alpaca farm, while a noble cause, probably doesn’t count. The IRS has a handy online tool to check if an organization is legit.

Second, get a receipt. If you donate $250 or more in one go, you need a written acknowledgment from the charity. For smaller amounts, a bank record or credit card statement usually works. The days of simply telling the government, “Oh, I put a twenty in the donation bucket, trust me,” are, sadly, behind us.

Cash is clean, simple, and the charity can use it for whatever they need most. It’s the vanilla ice cream of donations — unexciting, but always appreciated.

Want the quick guide on valuing your donated stuff so the IRS doesn’t laugh you out of the room? Keep reading →

Filing 101

👶 The Great Dependent Dispute

It’s a tale as old as e-filing. You’ve gathered your W-2s, tracked down 1099s, and navigated the digital labyrinth of tax software. You’re on the home stretch. You click “Transmit Return,” lean back, and … REJECTED.

The reason? Someone has already claimed your dependent.

Nothing tests the bonds of human relationships — be it with an ex-spouse, a co-parent, or a well-meaning but confused grandparent — quite like tax season.

The Basic Rules (Because Someone Clearly Didn’t Read Them)

Before we dive into the messy parts, let’s establish some ground rules that are non-negotiable in the eyes of the IRS.

And yes, we know your divorce decree says you get to claim little Timmy in even-numbered years. The IRS, with all the warmth and flexibility of a granite statue, has its own thoughts on that.

Want the rundown on tiebreakers, audits, and what happens when someone steals your dependent? Keep reading →

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Wild Tax Tales

💸 How Bitcoin Jesus Tried to Ghost the IRS

Roger Ver had it made. He was an early Bitcoin evangelist back in 2011, buying thousands when they were basically internet Monopoly money. People even called him “Bitcoin Jesus.”

Then, in 2014, he decided he was done with the United States. He renounced his citizenship and moved to St. Kitts and Nevis. Clean slate, new life, zero taxes.

Except … that’s not how any of this works.

When you leave America, you owe an exit tax. The IRS pretends you sold all your assets on the day you renounce, and you must pay tax on their fair market value. Ver had to report his bitcoins and pay tax on what they were worth in 2014.

He didn’t.

Investigators say Ver hired lawyers and an appraiser, then fed them false information. His companies reportedly held around 73,000 bitcoins. He didn’t disclose them. He also allegedly hid thousands more he owned personally. The law firm filed returns based on those incomplete numbers, and the IRS eventually noticed.

By 2017, Bitcoin exploded. Ver’s companies sold tens of thousands of coins for about $240 million. Again, he didn’t report it.

Fast forward to October 2025. Ver agreed to pay nearly $50 million in taxes, penalties, and interest to avoid prosecution. His tax bill alone was over $16 million, with penalties north of $12 million.

The lesson is simple. You can leave the United States, but you can’t ghost the IRS. The exit tax is real. Hiding assets is fraud. And the IRS always circles back.

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

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.