Hey {{ first_name | Neighbor }}. My son has a stuffed dog my wife hates. This week she figured out why. The stuffy's eyes are black with white dots meant to suggest reflections. To my wife, a doctor, this apparently reads as an unsettlingly awful case of glaucoma.

They tell you not to bring work home, but it inevitably brings itself. - AB

Note: After doing the research for today’s first news item, I feel fully vindicated about referring to readers to Upper Middle’s core demographic as “Oat Milk Elites”1.

PRESENTED BY ➷

The bracket doesn't lie, but it doesn't tell the whole story either. Duke is a heavy favorite against St. John's tonight — the number one seed against a five — but the Red Storm just knocked off Kansas on a buzzer-beater, and the Blue Devils nearly lost to a sixteen seed two weeks ago. If you've watched this tournament closely enough to have a take on whether St. John's +210 is generous, Novig is the peer-to-peer sports trading exchange where that opinion has a market — odds set by other fans, not a sportsbook padding its margins.

March Madness futures are live now, and the Sweet 16 is where brackets go to die. Novig makes every round matter — and doesn't take a cut of your winnings. So now is the time to get started.

Use the promo code UPPERMIDDLE and get 90% off up to $45.

Must be 21+ to enter. Please play responsibly. Void where prohibited. No purchase necessary..

What we’re drinking about while talking.


STATUS ➽ Usual Orders
Why do we order oat milk?
This week, a team from Google DeepMind published a study tracking the simulated consumption behavior of fifty AI agents modeled yuppity Angelenos on the dating circuit. The agents browsed stores, made purchases, went on coffee dates, noticed each other's consumer choices and modified their own in order to impress others. Fascinatingly, the model showed the agents' coffee orders converging on black coffee with oat milk due to what they dubbed "path-dependent convention formation." The mechanism: People ordered to impress so slight community preferences quickly become conventions. (A similar experiment on agents modeled against consumers in India showed a convergence on cow's milk). Not only did the agents copy each other orders, they copied each others discourse, spending much of their dates obliquely or directly critiquing consumerism. Also, they drove up the price of Chanel handbags2.


TASTE Butt Stuff
Why are cigarettes back in Hollywood?
Kylie Jenner probably isn't much of a smoker, but there she is on the cover of Vanity Fair with a lit dart jammed between her hyaluronic acid-plumped lips. She's also probably not much of a Sartre reader, but there she is illustrating his argument that smoking is "a way of appropriating the world." A cigarette is, after all, the rare object that can be possessed completely — using it and destroying it are the same thing. Smoking is consumption as self-assertion, and it is increasingly pervasive in post-Brat Hollywood: the cigarette trays at Vanity Fair's Oscars party, Hudson Williams lighting up outside the Armani show, the elegant drags of Ryan Murphy's Love Story.

And the posture is this: I'm not defined by what I abstain from. It's essentially antithetical to the Hollywood veganism of Silverstone and Harrelson and PETA era. Veganism is a serious moral position, but a silly social one,because the label is not a requirement of the behavior. You can eat 99% plants and one chicken finger without surrendering 100% of your seriousness. Similarly, you can smoke without being a smoker. Choosing to do so conspicuously demonstrates an understanding that being good at a party sometimes matters more than being right. Existentialists are a good hang..

MONEY Terminal Cases
Why is probability becoming an aesthetic?
Last weekend, Polymarket opened a "Situation Room" pop-up bar on K Street. Inside: dozens of screens and a spinning globe displaying live bets on everything from Ukrainian ceasefires to alien disclosure to the timing of U.S. military strikes on Iran. Aesthetically speaking, the pop-up was the opposite of the smoke-filled, wood-paneled bars that proliferated in D.C. — think The Palm — when people believed decisions were made in smoke-filled, wood-paneled backrooms. Polymarket's theory of power is that decisions get made in front of Bloomberg terminals. The Situation Room was kitted out accordingly.

The Situation Room was conceived and executed as the manifestation of the "monitoring the situation" meme, PR boilerplate that became a self-deprecating joke about doomscrolling that became way to caricature that specific male posture of looking thoughtfully at numbers while not really do much (the canonical example is Jeff Bezos intently watching a Blue Origin launch from a control room). Polymarket reappropriated the meme, attempting to monetize the posture by implicitly arguing that “data assault” is the preferred aesthetic of the financialized men fully in charge of the economy. They may not be wrong, but terminal isn't a great vibe.

Also… Airport lines may be the first progressive time tax. Congrat to everyone involved. Lululeopard? March Madness means rooting against Duke (and people who went there).

Upper Middle is an independent publication helping oat milk elites reframe their relationships with status, taste, and money. Please help us keep the lights on (dimly) by joining Upper Middle Research, which pays mid-career professionals as much as $200/hour to take targeted surveys.

CLASS NOTES ❧ Dept. of Koopa Studies

We’re all playing the game. Shouldn’t it be fun?

In the original Super Mario Kart for SNES, there was a 31.3% chance any given item box struck by a driver in first place would contain a banana, a 29.1% chance any given item box struck by a driver in fourth place would contain a banana, and a 3.1% chance any given item box struck by a driver in last would contain a banana. The game kept stoned college kids entertained for the same reason as frat parties: They knew they had a slim chance of coming from behind.

Since Mario Kart debuted in 1992, Nintendo has been zhuzhing its item box algorithm and adding new items. In 1996, Mario Kart 643 introduced the blue shell, which detonates on the leader. In 2014, Nintendo released Mario Kart 8, which replaced its position-based item distribution odds with distance-based odds. This year, Mario Kart World doubled the field to 24 and reverted to position-based item distribution odds because position matters more in a crowded field.

The good folks at Nintendo put a lot of thought into this stuff because math is what keeps stoned asses on filthy futons. The game must be fun or, in the Weberian sense, enchanting — meaning the ritual of playing must feel genuinely connected to the outcomes. The alternative is a disenchantment, what happens when behavior feels uncoupled from results.

Most of the time, the conversation about wealth inequality is moralized because in extremis it is undeniably a moral issue. But it's not only a moral issue. It's also an enchantment issue. America's economy is more enchanting than most, but less enchanting than it ought to be, specifically for those running second, third, and fourth – the folks statistically most likely to have formed their sense of fairness on Toad’s Turnpike.

And it's not an overstatement to claim that Millennials internalized Mario Kart game dynamics. Since 2019, F1 has introduced a complicated system rubber-banding — the technical term for an item distribution system designed to keep the field competitive — in order to capture Millennial interest. Cost caps. Aerodynamic regulations designed for closer racing. Redistributed prize money. These all seem fair to people whose early exposure to racing involved turtle shells.

But rubber-banding is not inherently fair. As the game designer and media theorist Ian Bogost has noted, rubber-banding is designed to simulate equity without necessarily producing it. The probability that a first-place driver wins after two laps is far higher than the probability that any given blue shell reshuffles the final order. In Bogost's telling, the real winners are the invisible Koopas stocking the boxes — but without even going there, it's fair to conclude that the game stays fun when players feel like they are competing with every racer, not just the one immediately in front and behind.

The American economy doesn't feel like that. The top 1% of households holds 30.5% of all wealth. The top 10% holds 67%. The bottom 50% holds 2.5%. Powerful items are distributed to those at the front of the field with coins raining down on everyone else. This system doesn't just space the racers considerably — it creates a dynamic in which the racers in second, third, and fourth are unlikely to climb into first or fall into fifth, but are well positioned to use the power items at their disposal to assault each other. SAT prep. School district premiums. College admissions packaging. Private tutoring. All green shells bouncing through a fruit salad of bananas left by the item-laden leader.

Bananas take a lot of forms. The 2017 SALT cap, designed to hit upper-middle homeowners in high-cost states, was a banana. The Alternative Minimum Tax, which catches high earners using deductions while leaving the genuinely wealthy — who have tax structures that route around it entirely — untouched, is a banana. Private equity, which gobbles up suburban providers — vets, childcare centers, pediatricians — and hikes costs is a banana. These items have not been introduced at random. It's malicious game design. It's disenchanting4.

Though it’s possible to inject enchantment back into the system, doing so requires suspending one’s interest in fairness. At least that’s the approach Nintendo took when they introduced Bullet Bill.

Debuting in 2008’s Mario Kart Wii, Bill appears only when drivers in ninth place or worse strike an item box. He’s not a weapon. He’s a loophole. For eight second, he rockets unskilled racers through the game, scattering opponents. He is by any measure, the least fair item in the game. He’s also one of the most popular. That’s because racers aren’t just judging the game on fairness. They’re judging it on enchantment. 

Nintendo considers both. We should too. Because if everyone stops playing, they’ll probably get up to something worse..

[1] I blatantly and unapologetically stole this fun little affection from the very charming Australian Linkedinfluencer Edmund Lau, who may have stolen it from someone else. I don’t care.

[2] Also, Rolexes. Though an additional finding was that demand increased for luxury goods when prices didn’t go up, which doesn’t exactly dispute the Veblen Goods hypothesis (people pay for the price of luxury goods in service of exclusivity), but gets close.

[3] The game you played after Goldeneye because Goldeneye didn’t have a mechanic to level the field so the one weird kid who liked screamo music and a girl that wouldn’t give him the time of day always won.

[4] It’s also really dumb. If you’re tremendously wealthy or powerful and you’re looking to rig a system, you should rig it to be enchanting, not disenchanting for no other reason that having your head put on a pike can be uncomfortable.