Buy now, pay... maybe?

When did "maybe" become a selling point?

A financial product launched this week with the literal tagline "buy now, pay maybe." As in: you might owe this money, or you might not. They decide, and you won't know until after you swipe.

It makes sense that it's landing. Because somewhere along the way, we got so used to money feeling stressful and fixed and heavy that the possibility of something just being free started to feel like actual relief.

And I get it, honestly. When everything costs more and nothing feels certain, "maybe free" sounds like the universe finally cutting you a break. I just think it's worth knowing what you're actually signing up for before you swipe.

💌 What's your gut reaction when something financial sounds too good to be true? Hit reply and let’s chat about it.

P.S. If you want to talk through your own finances, you can book a free 1-hour coaching session here ☎️

(Actual answer at the end of the newsletter 👇)

The basic mechanics are straightforward: load money, spend money, purchases draw from your balance with no credit and no overdrafts. What makes it different is that the company might randomly decide not to charge you for something, without publishing any odds or criteria. You find out only after you swipe.

And the behavior it's already producing is worth paying attention to. A since-deleted Reddit post described one user's boyfriend buying the same product ten times on Amazon (hoping one would be free) and returning the other nine. That's not someone being reckless. That's someone responding completely rationally to the incentive structure the product created. Which is exactly the problem.

Consumer advocates say it "introduces the casino to the checkout line." They've also pointed to something worth naming: "financial nihilism." The idea that people think the odds are so stacked against them that taking unnecessary risks starts to feel logical. And in an economy where homeownership feels out of reach and student loan debt sits at $1.83 trillion, that's not a fringe feeling.

This card isn't an isolated product. It's the latest in a pattern. More than a quarter of Americans now have active accounts on online sportsbooks. Prediction markets let people bet on basically anything. A teen banking app pays users up to $200 a month for playing games. One by one, financial products are being redesigned to feel like entertainment and to carry a little charge of "what if" every time you engage.

This card is just one example. But the psychology behind it is everywhere. Here's how to recognize when a financial product is designed to feel like a game.

📌 You start spending to feel something. Not because you need something, not because it fits your budget, but because the act of spending carries a little charge. That feeling is the product. Recognize it for what it is.

📌 The possibility of winning changes what you buy. A chance at free, a shot at a prize, a spin of a wheel. If the "what if" is factoring into a purchase decision, the product is working as designed. Your wallet is now part of the game.

📌 You're engaging with money apps for entertainment, not information. Checking balances to feel something, opening apps to see what happened, refreshing to find out if you won. Managing money should feel useful, not exciting. When it starts feeling like the latter, that's worth pausing on.

📌 The losses start to feel like bad luck instead of costs. "I'll get one back eventually" is how gambling justifies itself. In personal finance, every dollar out is a real dollar. Products that blur that line are doing it on purpose.

If you're thinking about your own money habits right now, that's a good sign. Let's talk. ☎️

Americans who say their financial situation is getting worse

This is the highest since Gallup started tracking in 2001, which is higher than during COVID and even higher than the Great Recession.

April inflation (the highest reading in nearly three years)

And for the first time since 2023, prices are rising faster than wages. Energy alone accounted for over 40% of the monthly increase, driven by the war in Iran and the closure of the Strait of Hormuz. Grocery prices jumped 0.7% in a single month, which is the biggest leap in nearly four years.

Where oil futures are sitting right now as the U.S. and Iran remain at a standoff

Without the conflict, experts say fair value of oil would be closer to $65 a barrel. That $35 gap is what's showing up in gas prices, grocery bills, airfare, and just about everything else.

Need to talk numbers? We can help you sort out your money.

Early human ancestors started making stone tools around 2.6 million years ago (long before farming, writing, or money existed).