What happened to Jack Dorsey? Do you still remember Jack Dorsey? 😇
He happens to be one of my good friend's longtime celebrity crushes. 😂
Although, if the Jack frozen in your memory is the clean-cut, blue-eyed Silicon Valley founder in a white shirt, you may want to Google him again.
Because somewhere along the way, Jack Dorsey transformed from a fairly conventional tech CEO into something closer to a bearded techno-monk/cypherpunk wandering around trying to decentralize the world.
And his story since Twitter is actually fascinating.
Jack co-founded Twitter in 2006 and became its first CEO.
But here's something people often forget: he was fired from his own company.
In 2008, Twitter's board pushed him out as CEO amid concerns about his management. Dorsey later described losing Twitter as feeling like being punched in the stomach.
So what does a founder do after being thrown out of the company he created?
Apparently, build another billion-dollar company.
In 2009, Dorsey and his good buddy Jim McKelvey created Square around an incredibly simple idea: make it possible for almost anyone—a food-truck owner, artist, hairdresser, yoga teacher or tiny shop—to accept credit-card payments with a little reader plugged into a phone.
In some ways, Twitter democratized publishing. And Square democratized being a merchant.
Square went public in 2015 at $9 a share. The IPO had actually been priced disappointingly low—but on its first trading day, the stock jumped 45%.
And that same year came one of the strangest corporate comebacks in Silicon Valley history: Jack Dorsey returned as CEO of Twitter.
For the next six years, he was simultaneously helping run Twitter and Square—two public companies.
Then in November 2021, he stepped down as Twitter CEO for the second and final time.
Important detail: this happened before
@elonmusk bought Twitter. Dorsey left Twitter's board in May 2022; Musk's acquisition wasn't completed until October.
So - no, Elon didn't kick Jack out - Jack was already leaving.
And almost immediately afterward, Square changed its corporate name to Block ( $XYZ ) .
Square itself still exists — the merchant business is still called Square — but the parent company became Block, reflecting Dorsey's much bigger obsession with Bitcoin, blockchain and decentralized technology.
Block eventually came to include Square, Cash App, Afterpay, TIDAL, Bitkey and Bitcoin-mining infrastructure.
At one point Square was one of Silicon Valley's hottest fintech stocks.
Then the pandemic-era came and the fintech bubble burst.
The company had become sprawling. Headcount had ballooned to nearly 13,000. Investors started asking whether Jack had built an ecosystem—or simply accumulated too many experiments.
Then Jack did something extremely Jack Dorsey.
He started shrinking the company.
Around 1,000 employees were cut in early 2024.
Another roughly 930 went in 2025.
And then in February 2026 came the bombshell: Block cut more than 4,000 jobs—roughly 40% of the company in one shot—taking the workforce from more than 10,000 people to just under 6,000.
And this time Jack explicitly said the reason was AI.
His argument was essentially: AI has changed what it means to build a company. Smaller teams equipped with intelligence tools can accomplish what previously required huge organizations.
Wall Street loved it.
Block shares jumped roughly 25% after-hours after the announcement.
So the guy who once helped invent social media is now conducting one of corporate America's more radical experiments in what an AI-native company might look like.
But this is only half the story.
Because Jack seems increasingly uninterested in conventional companies at all.
Remember Bluesky?
Jack helped initiate the project while he was still running Twitter. The original idea was beautiful: instead of Twitter controlling the social network, build an open protocol upon which many different social networks could exist.
He later joined Bluesky's board. And then, in classic Jack fashion…
he left that too (am not that surprised, personally! Have you ever used Bluesky?).
In 2024, Dorsey stepped off Bluesky's board after becoming disillusioned with the direction it was taking. He argued that it was beginning to reproduce many of the things he wanted decentralized social media to escape: a conventional company, centralized moderation and institutional control.
He's since become much more interested in open protocols such as Nostr.
Then came perhaps his strangest project yet.
Bitchat.
Yes, that's really the name (you can tell Jack's conviction with Bitcoin and the related family).
In 2025, Dorsey launched an encrypted peer-to-peer messaging app that can communicate through Bluetooth mesh networks.
No cellular network.
No Wi-Fi required for nearby messaging.
No phone number, central server, nor conventional account.
Nearby phones effectively create their own little communications network.
At first it sounded like another billionaire weekend experiment.
Then people started actually using it during internet restrictions.
And by July 2026, things had become serious enough that India's cybercrime authority ordered GitHub to remove repositories hosting Bitchat's code. Dorsey publicly posted the order and accused the government of wanting the technology taken down.
Think about the trajectory here.
Jack helped create:
Twitter: challenged traditional media gatekeepers.
Square: lowered barriers to accepting payments.
Bitcoin: became Jack’s preferred alternative to centralized money and banking infrastructure.
Nostr: social media without one central platform.
Bitchat: messaging without relying on a central network.
There is a remarkably consistent philosophy underneath all of this: remove the intermediary.
And then there's the other question everybody inevitably asks when they see him now:
Jack… what happened to your look? 😂
Young Jack looked like a perfectly normal startup founder.
Modern Jack has the shaved head, enormous beard, black clothes, meditation retreats and vaguely post-apocalyptic philosopher aesthetic.
This wasn't an overnight transformation.
Around the period when he returned to Twitter in 2015, his public persona started becoming much more ascetic. He became known for wearing Rick Owens, practicing Vipassana meditation, doing ten-day silent retreats and experimenting with extremely restrictive fasting. In 2019 he said he was eating only one meal a day during the week and sometimes fasting through the weekend.
I wouldn't read the beard itself too deeply.
But the broader transformation seems meaningful.
Corporate Jack gradually became anti-corporate Jack.
The CEO started looking more like a monk.
The founder of one of history's most powerful centralized social networks became obsessed with decentralization.
The man who built giant companies increasingly began questioning whether giant institutions should exist in their current form at all.
Even his personal life has always been slightly unconventional.
Dorsey has never cultivated the traditional married-CEO-with-family public image. He had a long on-again/off-again relationship with artist and entrepreneur Kate Greer, and in 2018, when Dorsey was 41, he was reportedly dating 23-year-old Sports Illustrated/Vogue model Raven Lyn Corneil—which naturally generated its share of Silicon Valley-billionaire-dating-model headlines.
His current romantic life seems considerably more private.
Which somehow fits the later Jack.
Today, at 49, Dorsey reportedly lives a fairly nomadic existence, still meditates, still runs Block, still believes deeply in Bitcoin and open-source protocols—and keeps experimenting with systems designed to remove centralized control. WIRED recently described him as living nomadically and trying to rebuild Block itself “as an intelligence.”
You don't have to agree with him, but just like Steve Jobs put it - the only thing you can't do, is ignore him. 😇
(Jack, if you ever see this, I'd like to interview you one day for the stories that nobody has heard before, the hero's journey!)