White Collars Soaked in Cold Sweat → Rich Friend Gap

Hey Neighbor. True story. Few days ago. Two guys talking at the Intelligentsia cafe in Silver Lake. “My guy at Merrill admitted it,” says the first. “No one knows what to do.” The second nods. “At least the market is back,” he says. “That’s something.” A moment of silence. The whine of an espresso machine.

“Is it?”

➺ The results of our “Interesting Times” financial anxiety survey are below. I’m sharing them with all Upper Middle subs (including non-members like you) because it feels… right. We are, after all, in this thing together. That said, please support what we do by becoming a Research Member when you have a moment. It’s free – actually, you’ll make money – and you’ll get access to all our peer survey data going forward. 

➺ Thanks to “Hamster Huey” (Nice C&H reference, btw) for the intro anecdote. Have you recently encountered awesomely Upper Middle behavior in the wild? Tell us about it!

➺ Have a friend you think might enjoy this newsletter? Tell them about it. We’re not a big company so that’s actually a huge help. (Also, a fun passive aggressive way to piss off your aging parents.)

➺ Everyone getting back in shape right now, which means everyone is super stiff and limping every morning. Suburban bagel shoppes look like a zombie movie.

Upper Middle’s 2025 “Self-Assessment” Survey is our attempt to find out how members of the oat milk elite think they’re doing in their personal and professional lives (compared to their expectations). Data will be shared with survey participants and, as always, with members.

ADVICE FROM THE UPPER MIDDLE

• Diversify and increase number of income streams if possible. Keep an eye out for distressed assets to create new opportunity." (Left, $150k-199k income, $100k-249k net worth)

• "Buy every dip. Harvest losses for tax purposes. Maybe learn how to fuck with options if you're into that sort of thing." (Center, $50k-74k income, $1M-2.5M net worth)

• "Bet on America. If you're wrong, none of it will really matter." (Right, $200k-499k income, $1M-2.5M net worth)

• "Read or listen to the news in longform, don't consume it on social media. Go slow to go fast." (Center, $200k-499k income, $500k-749k net worth)

• "Keep the expensive cat food. He doesn't know there's a recession." (Left, $50k-74k income, <$50k net worth)^[4]

SUPER BLEAK PARTING SHOT…

“Throughout history the very wealthy and powerful have always needed someone to cook their meals and maintain their properties, so the motivation has always been suppression and control of other humans, but not the complete elimination of other humans…. They needed our tithes, our taxes, our labor, or our flattery to enjoy life at the level of luxury they desired. With AI robots that will drastically change.”(Center Left, $$100K-$150K income, <$100k net worth)

[2] I’ll expand more on this at some point, but the very wealthy have organized capital to a far greater degree than the Upper Middle has organized labor. You live downstream from that and it explains a lot.

[3] The effect of this will likely be fashion stagnation, which is already clearly visible on the streets of New York, and the rise of fashion-adjacent consumer products (think: heavily branded coffee cups that can be carried around like little totems).

[4] I don’t know to what degree this was intended as a joke, but I’m take it super seriously. I may not be able to control much in the world, but my fat dog will never know lean times!