11 March 2026

Today in Tech Bro Psychopaths

Block (formerly Square) CEO Jack Dorsey donned a baseball cap with "Love" lettered on the front while announcing that he was firing 4,000 employees and replacing them with AI.

Next time, just be honest, wear a hat with a Totenkopf. 

Twitter co-founder and Block (formerly Square) CEO Jack Dorsey ain’t your typical corporate suit. For one, he doesn’t always wear them. He brings up “world peace” when endorsing his favorite tech like crypto. Nobody really knows where he lives. He meditates frequently and sports a longish beard. He comes off as more New Age guru than CEO.

So perhaps it was very on brand that, when Dorsey announced he was firing 4,000 employees at Block, he was wearing a hat that said “LOVE” on it in prominent lettering.

Was the “LOVE” hat was tone-deaf? That may seem a silly consideration compared to the broader concern of Dorsey eliminating around 40 percent of his company’s workforce, especially given his explanation that AI motivated the cuts.

There is something very wrong at the core of Silly-Con valley.

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