Dumb & Dumber: Eavesdropping on Your Wife, Then Kissing Your Cousin

Welcome to the monthly wrap up of missteps that may hit someone’s pocketbook (often yours).

I’m going to skip politics, because you already know how awful it is. One guy can’t remember who’s alive or dead or when his son passed away. Another guy loses “bigly” in court every time he opens his mouth, and a third guy claims he had nothing to do with a Super Bowl ad promoting his campaign by repurposing a commercial reminiscent of his assassinated uncle — “I’m so sorry!” — though he still has the ad posted on his X account.

I also don’t have the stomach to wade into the current culture wars, even though Google’s troubled ChatGPT-style AI bot called Gemini is having to be reworked again. Gemini’s image generator gave Orwell a run for his money this month by refusing to recognize facts, like every pope in history has been (checks Google) a white male.

CNN asked Gemini a few questions/CNN

And if Elon Musk wants to subsidize lawsuits filed by fired Disney employees alleging discrimination over free speech, it’s his money. Both he and Disney have a market value of $200 billion, so it’s a fair fight, financially.

Instead of all that nonsense, I prefer to highlight under-the-radar money madness.

Today I offer up a few quick hits to whet your appetite, and tomorrow I’ll publish the official Dumb & Dumber list.

— Lost in Love

Tyler Loudon had a bad month. So did his wife.

To hear Tyler tell it (according to the SEC), his wife was busting her butt working from home as part of the M&A department at oil giant BP. So when he overheard her discuss with colleagues an acquisition of TravelCenters of America, he thought he might buy a bunch of shares of the publicly-traded truck stop company before the news broke. He could make a killing, and then his wife wouldn’t have to work so hard!

It’s called love, friends.

Sure enough, when the deal was finally made public, TravelCenters’ stock shot up 71%, and Tyler netted $1.7 million.

Someone noticed.

This month Tyler pleaded guilty to insider trading in federal criminal court. He still faces civil charges at the SEC.

(Hint: Don’t get greedy. Make only $50k on inside info — which is still illegal, and, like, wrong — but you probably won’t raise any red flags. You didn’t hear that from me.)

Meantime, the SEC says Tyler’s wife didn’t know anything, but BP reportedly fired her anyway.

She’s moved out and filed for divorce.

— Adam Neumann Won’t Go Away

Why do billionaires keep doing business with Adam Neumann?

The man who created WeWork and led the shared-workspace company until he was forced out as it collapsed, now wants to buy back his old firm. The New York Times reports that Neumann’s lawyers accuse WeWork’s bankruptcy advisors of ignoring him.

I’d ignore him, too.

According to Neumann’s legal team, he wants to use his current company, Flow Global, to finance the buyback, and he’s getting help from hedge fund billionaire Dan Loeb. Meantime, Flow, which is supposed to be the WeWork of apartment living, has yet to get off the ground, despite a $350 million investment from Andreessen Horowitz, run by billionaire Marc Andreessen.

What kind of voodoo powers of persuasion does Adam have? Avoid direct eye contact!

— Off Target for Black History Month

Target released a “magnetic learning kit” highlighting civil rights icons for Black History Month. It got three of them wrong.

A teacher took to TikTok to point out that the depiction of sociologist and historian W.E.B. Du Bois was actually journalist Carter G. Woodson, while the image of Woodson was that of author and educator Booker T. Washington, and the one of Washington was Du Bois.

Target took the learning kit off the market as the retailer itself learned something about product oversight.

The real W.E.B. Du Bois, Carter G. Woodson, Booker T. Washington

— The Bankruptcy No One Cares About

American taxpayers will spend more this year to pay interest on our debt than we‘ll spend on national defense. Do not expect anyone to mention this during the election.

— Upsetting the Apple Car(t)

Apple is having a rough year. (Words I never thought I’d write.) After spending billions of dollars and ten years of work on a secretive electric car program, the company realized that creating its CarPlay software is a lot easier than building an actual car. It’s throwing in the towel, according to Bloomberg.

Shares rose on the news.

— Heel Study Falls Flat

A study out of Texas claims wearing high heels is good for you. The research — led by a man — claims that heels can improve mobility and make you “more efficient walkers.”

Let’s make grandpa start wearing stilettos.

To test the hypothesis, researchers recruited people who’d never worn high heels before and put them through their paces.

How many human guinea pigs volunteered? Eight. Eight people. Three women… and five men.

I know of at least nine who could refute these results.

— February’s Chutzpah Award + More Criminal Advice

Brandalene Horn is charged with renting over $800,000 in luxury clothes from unnamed rental sites — using 170 different accounts — and then (allegedly) reselling the goods on Poshmark. When the rental companies tried to charge her for not returning the clothes, she (allegedly) canceled the credit cards, or disputed the charges.

This takes work, people. Horn’s can-do entrepreneurial spirit makes America great. Think of what she could accomplish working on the right side of the law!

Horn was finally caught by an undercover agent because she used her actual address on various bogus credit card accounts.

I’m not sure why I feel compelled to repeatedly give advice on how to succeed in crime without really trying (don’t put anything in an email, don’t get greedy with insider trading), but c’mon. Your own address?

— Kissing Cousins

Finally, we’re back to saying it’s okay to marry first cousins. “The risk [of birth defects] to offspring is greater, but the increase is quite small,” writes The Economist. THE ECONOMIST. Well, it is a British publication, and the Royal Family has been marrying cousins for centuries. I’d say that’s an argument against it.

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Coming up, the financial foibles that rose to the top in February, plus Smart & Smarter, because good things happen, too.