11/18/25 Newsletter

We’re days away from turkey time, and while your oven might be preheating, the IRS never cools off.

This week’s lineup:

• 💀 The IRS killed its “free file” tool, and TurboTax popped champagne.

• 🚗 Gig drivers, meet the 15.3% tax twist.

• 🧾 How long to keep receipts before you can shred guilt-free.

• 🏝️ An oft-naked “Survivor” winner outplayed everyone—except the IRS.

Tax Alerts

⚰️ RIP, IRS Direct File

Remember that plucky little IRS experiment that let you file your taxes directly with the government—no third-party upselling, no “premium” add-ons, no hidden paywalls?

Yeah. Blink and you missed it. It’s officially toast.

What Went Wrong?

• Low Use: Only 0.2% of taxpayers used it in 2025—about 300,000 out of 146 million returns.

• High Cost: Roughly $138 per return, according to a House report.

That was enough for former IRS Commissioner Billy Long to declare, with maximum subtlety:

“You’ve heard of Direct File? That’s gone. Big Beautiful Billy wiped that out.”

You can’t make this stuff up.

But ... People Liked It

90% of users said they loved it—calling it simple, fast, and trustworthy.

Critics argue this wasn’t about cost, but about protecting profits. Killing Direct File, they say, handed a gift to the tax software giants. A few "free" options remain, but most come with fine print sharp enough to cut yourself on.

For now, your best bet is still the same: patience, Tylenol, and maybe a good accountant.

👉 Want the full, baffling story on why Direct File got axed and where you can still (maybe) file for free? Read our full guide →

PS: If your tax situation’s gotten a little too weird for “free,” our sister company TaxQuotes can help. They’ll match you with real, vetted tax pros who’ll handle the messy stuff—without charging yacht money.

Business & Gigs

🚗 What Uber & Lyft Don’t Tell You About Taxes

When you sign up to drive, they sell you the dream: Be your own boss. Set your own hours. Earn great money.

What they don't give you is the brutally honest, one-page memo that would save you from a world of financial pain a year later.

This is that memo.

The First Shock: The 15.3% Surprise Party

When you have a "normal" job, your employer quietly pays half of your Social Security and Medicare taxes. You only see the other half disappear from your paycheck.

As a rideshare driver, you are your own boss. Congratulations - you now get to pay both halves.

This is called the Self-Employment Tax, and it's a flat 15.3% tax on your profits that's added to your regular income tax. It's the biggest, nastiest surprise for every new driver, and it's why you can't just look at your weekly payout and think it's all yours.

A massive chunk of it already belongs to the IRS.

Want the smart driver’s guide to avoiding surprise tax bills? Read the rest →

Filling 101

🧾 How Long Do I Keep Tax Records?

It’s an annual rite of passage, right up there with finding desiccated Halloween candy in the back of the pantry and pretending to know the lyrics to “Auld Lang Syne.”

We’re talking, of course, about the ceremonial dusting off of the shoebox, that cardboard sarcophagus brimming with a year’s worth of questionable decisions, crumpled receipts, and the lingering fear that shredding any of it will instantly summon an IRS agent to your door.

Inside every taxpayer, two wolves are locked in eternal combat. One is a minimalist, a Zen master of decluttering who whispers, “It’s been three years. Let it go. Think of the confetti.”

The other is a paranoid hoarder, convinced that the one faded gas station receipt you toss is the single thread holding your financial universe together. This second wolf has built a fortress of paper around your office and named it “just in case.”

So, who’s right? When is it finally safe to reclaim that precious shoebox real estate?

The Three-Year Rule: A Deceptive Starting Point

While the most commonly cited rule for keeping tax records is three years, it is absolutely not the final answer. Think of it as the starting point for a marathon, not a finish line.

The IRS generally gives itself a three-year window from the date you filed your return to poke around in your financial affairs. If you were an early bird and filed in February, the clock doesn’t start ticking until the official tax deadline, which is usually April 15th.

This is the foundational rule, the one that gives the minimalist wolf a glimmer of hope. Three years sounds delightfully manageable. This, of course, is where the trouble begins, because nothing involving taxes is ever that simple.

Want the real rules on what to keep, what to toss, and when it’s finally safe to shred? Read the rest →

Here’s an un-boring way to invest that billionaires have quietly leveraged for decades

If you have enough money that you think about buckets for your capital…

Ever invest in something you know will have low returns—just for the sake of diversifying?

CDs… Bonds… REITs… :(

Sure, these “boring” investments have some merits. But you probably overlooked one historically exclusive asset class:

It’s been famously leveraged by billionaires like Bezos and Gates, but just never been widely accessible until now.

It outpaced the S&P 500 (!) overall WITH low correlation to stocks, 1995 to 2025.*

It’s not private equity or real estate. Surprisingly, it’s postwar and contemporary art.

And since 2019, over 70,000 people have started investing in SHARES of artworks featuring legends like Banksy, Basquiat, and Picasso through a platform called Masterworks.

• 23 exits to date

• $1,245,000,000+ invested

• Annualized net returns like 17.6%, 17.8%, and 21.5%

My subscribers can SKIP their waitlist and invest in blue-chip art.

Just click this link

_{Investing involves risk. Past performance not indicative of future returns. Reg A disclosures at masterworks.com/cd}

Wild Tax Tales

🏝️ Outwit, Outplay, Outlast… the IRS? Not So Much.

When “Survivor” first hit TV, America was hooked. Strangers marooned on an island, scheming for food, alliances, and one giant payday. At the center of it all was Richard Hatch, the sharp-tongued corporate trainer who invented reality-show strategy before it was a thing.

He played brilliantly and walked away with the million-dollar prize. But when tax season rolled around, Hatch made one fatal mistake: he didn’t tell the IRS about his winnings. Or about the $300,000 he made from media appearances and rental income.

His defense? He thought the show’s producers were paying the taxes for him. The producers quickly denied that. The jury didn’t buy it either.

Hatch was convicted of two counts of tax evasion and sentenced to 51 months in federal prison. After release, he was sent back again for failing to amend his returns and pay what he owed.

He outwitted, outplayed, and outlasted his rivals — but not the IRS.

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

• 🕳️ A quick look at the most common places the rich stash money to shrink their tax bills.

• 📈 New 2026 401(k) and IRA limits mean you can shelter a bit more from taxes next year.

• 🤖 The IRS is using AI to target audits more precisely, especially for complex or high-risk returns.

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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