He retired, got a hell of a lot richer through passive gains to his investment portfolio, then came back to run Google, presiding over the precipitous decline of search quality, which he responded to by telling his workers that he expected them to put in 60 hours/week:

pluralistic.net/2025/08/18/see…

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One of the strangely satisfying aspects of the Trump presidency is that every now and then, he'll pick a random billionaire (say, the CEO of Intel) and publicly call him an asshole for a couple of days, generally to prompt that particular billionaire to bend the knee to him:

cnbc.com/2025/08/11/intel-ceo-…

4/

Trump flip-flops on Intel CEO, calls him 'success' days after demanding resignation

President Trump said Monday that he met with Intel CEO Lip-Bu Tan, days after calling on the chipmaker to resign.

^{Jordan Novet (CNBC)}

Sometimes, he'll force these billionaires to publicly humiliate themselves for him - like when he made Tim Apple hand-build a little gold participation trophy for dictators on camera and then present it to him, groveling all the while:

anildash.com/2025/09/09/how-ti…

The reason this makes such great TV is that we all know that normally, these guys never have to tolerate *any* criticism. They live in hermetically sealed bubble of sycophancy.

5/

How Tim Cook sold out Steve Jobs - Anil Dash

A blog about making culture. Since 1999.

^{Anil Dash}

This is what makes them so, so stupid (it's also why Trump so so unbelievably fucking stupid). Look, I come up with stupid ideas all the time, but I've learned the hard way that if I open my teeth and let these mental farts escape from my face, the people around me will tell me that I'm an asshole and make me feel bad.

6/

Trump, on the other hand, can tell us to all inject bleach and claim that solar panels are killing bunny rabbits and everyone around him tells him he's a genius:

eenews.net/articles/fact-check…

He's got a button on his desk that summons Diet Cokes. This is a guy who brazenly cheats at *golf*, *on camera*, without any pushback. This is a recipe for crawling up your own asshole and dying:

newsweek.com/donald-trump-golf…

7/

Video of Donald Trump ‘Cheating’ at Golf Goes Viral

Footage of President Donald Trump on a golf course has gone viral, with people accusing him of cheating.

^{Jordan King (Newsweek)}

As the moral philosopher David St Hubbins said, "It's such a fine line between 'clever' and 'stupid.'" If you want to come up with interesting ideas, you have to entertain some outlandish ones. But if you live in a world of yes-anding improv partners who get fired if they break character in the Mad King LARP you're paying them to play, then your bad ideas will inexorably devour your good ones.

8/

Give Howard Hughes some constraints and he'll build you a bunch of cool airplanes. Take away those constraints and he'll start wearing kleenex boxes on his feet, growing his fingernails real long, and saving his piss in jars. Constraints are frustrating, but they're good for you.

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Billionaires are on a relentless quest to isolate themselves from the rest of us. The yacht industry, private space exploration, seasteading, luxury bunkers - their whole thing is escaping the constraints imposed by others. They want to be "sovereign" - that is, *toddlers*:

pocketcasts.com/podcast/lever-…

10/

The Grotesque Fruits Of Your Labor (With Evan Osnos)

Listen to your favorite podcasts online, in your browser. Discover the world's most powerful podcast player.

^{Pocket Casts}

The more isolated they get, the stupider they get. No one's telling them no. Sergey Brin has gotten unmistakably stupider since he stopped going to Town Hall meetings where Google's once-valued engineering staff got to criticize the company. Zuckerberg's whole manophere/surfer dude rebrand coincided with his decision to stop attending the company-wide engineering meetings, which he called "Not a good use of my time."

11/

One thing all these guys have in common: they *love* chatbots. Why not? A chatbot is the perfect lickspittle. Ask one to generate a gnarly regular expression, try it, then paste the resulting (inevitable) error message into the chat, and the bot will positively cower in contrition: "You're absolutely right, I'm really stupid and you're *very* smart for noticing. I forgot to put in a curly brace.

12/

"Please, if you can see your way clear to giving me another chance, could I pretty pretty please try again? I mean, only if you don't want me to kill myself instead."

Sure, an AI isn't real - but remember, as far as billionaires are concerned, almost *everyone* is an "NPC."

Not so long ago, nearly every human/AI contact was a ritual humiliation in which the computer said no. No, you can't have that drug your doctor prescribed, the AI says no.

13/

No, you can't get bail, the AI said no. No, you can't keep your kids, the computer said no.

The rise of consumer-facing LLMs has given us all a taste of what it's like to be a billionaire. Like William Gibson said, the future was there, it just wasn't evenly distributed. Tech lords invented a machine for lowering your IQ. It's not AI psychosis, it's billionaire's disease:

pluralistic.net/2025/09/17/aut…

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Image:
Cryteria (modified)
commons.wikimedia.org/wiki/Fil…

CC BY 3.0
creativecommons.org/licenses/b…

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File:HAL9000.svg - Wikimedia Commons

^{commons.wikimedia.org}