‘Checked’ Twitter boss Jack Dorsey’s ‘eccentric’ life

Even among Silicon Valley’s weird geniuses, Jack Dorsey still stands out for his eccentrics.

“He’s almost like one of the Russian dolls, with a new exterior to be fitted every few years,” Nick Bilton, author of “Hatches Twitter, ”Told The Post about Dorsey’s sense of fashion. “He went through a phase where he wore these strange Dior Homme [reverse collar] shirts. Now he’s in his [designer] Rick Owens bohemian phase. At one point, he was obsessed with wabi-sabi, a Japanese design philosophy that is strange and eccentric. There have been jeans and A-line skirts. “

The tech world was shaken on Monday by the announcement that Dorsey – the one-time punk rocker, NYU apostate, licensed masseur and future fashion designer – would step down as CEO of Twitter, the company he co-founded in 2006.

“No one expected Jack to reach the heights he reached,” said a former employee. “He used to be a semi-homeless, hippie, software developer who couch surfing.

Twitter CEO Jack Dorsey licks the sun with the stunning bikini model Flora Carter in South Beach, Miami.
Dorsey joined bikini model Flora Carter in South Beach, Miami.

“In many ways, he’s anti-CEO. Those guys are crazy guys, and he’s his own person. He’s just another guy. Whoever takes Jack’s place on Twitter will be less characteristic than Jack.” (Twitter CTO Parag Agrawal will take the lead.)

Shareholders, meanwhile, could not be more pleased. When CNBC announced the 45-year-old’s abdication, Twitter shares rose more than 11 percent. Maybe they were relieved not to be confronted with more stories like back then, rapper Azealia Banks claimed Dorsey had sent clippings of his Rip Van Winkle-like beard so she could use them for a protective amulet. Dorsey denied it, and Banks’ Twitter post about it has since been deleted. The beard, meanwhile, has its own tongue-in-cheek of account.

Nor is it the first time Dorsey has resigned.

He originally served as CEO for the first 18 months of Twitter’s existence, from April 2007 to October 2008, when he stopped to be replaced by the more buttoned-up Evan Williams.

When Dorsey took over the position in 2015, his sensitivity had shifted from nerdy start-up founder – who once covered his nose ring with a patch when a boss asked him to get rid of it – to full-on bohemian.

The former employee believes that Dorsey brought good things to Twitter, but that the tech guru has too many distractions to keep him in one place right now. It is after all a man who has said that he tries to meditate for two hours every day.

Dorsey and Sean Penn go for a shirtless walk on the beach in Hawaii.
Dorsey has also been known for hanging out with Sean Penn (left).

“He worked extremely hard and spent an enormous amount of time building the company. But his interests were too far-reaching for him to be a focused CEO,” said the former employee.

Bilton is less generous. “A lot of people,” he told The Post, “think Dorsey is a checked CEO.”

Dorsey has said he wants to focus more on the digital payment system Square and his philanthropy. Meanwhile, among the hobbies that draw his attention is to woo some of the most attractive women on the planet. He has been associated with swimsuit models Flora Carter and Raven Lyn Corneil, yoga instructor Kate Greer, fashion model Lilly Cole and “Boss bitch”Author Nicole Lapin.

Not bad for a guy who as late as 2005 did not know what a text message was.

Dorsey meditates in a cave in Mandalay.  Dorsey is a holistic supporter of extreme heat and cold as well as microdosing of LSD.
As a holistic supporter of extreme heat and cold as well as microdosing of LSD, Dorsey is seen here meditating in a cave.

According to “Hatching Twitter”, Dorsey first found out when a girl asked him to send her a message instead of calling. His desire to woo women, meanwhile, was to present them with origami cranes he himself made.

The former Twitter employee believes these ladies are attracted to Dorsey for more than just his billions: “It’s not the money at all. He’s legally interesting. It makes him a lot cooler than, say, Zuckerberg.”

Dorsey, worth about $ 11 billion according to Forbes, he grew up in St. Louis. Louis – where his mother was a homemaker and his father an engineer – and now lives in a glass mansion overlooking the Golden Gate Bridge. It has been said that he eats breakfast with water, salt and lemon and spends about 75 minutes every day walking from his home to his office. But he reportedly prefers to work from home under infrared light, which is supposed to relieve stress. He claims he only eats one meal a day and fasts on the weekends.

He is also, according to the Times of London, approved microdosing of LSD.

Dorsey (center) joins Floyd Mayweather and Logan Paul in Miami Gardens, Fla.
Dorsey (center) and his beard stood out at Floyd Mayweather against the Logan Paul match in June.
Getty Images

As for Dorsey’s claim that he spends 45 minutes a night jumping from a 220-degree sauna to ice-cold water and back to the sauna, Bilton is in doubt.

“The world record for a sauna is only six degrees more than what he says he does,” said Bilton of Dorsey’s preferred temperature, which exceeds the boiling point. “And a Russian died of it.”

Adam Fisher, author of “Genius Dal, “says Dorsey” is a bohemian who by mistake ended up as a billionaire and follows the path he has always been on. “

Dorsey attends an event in NYC with model Raven Lyn.
Dorsey was for a time associated with model Raven Lyn Corneil.
Neil Rasmus / BFA.com

Sometimes, though, these things do not go as planned. In 2019, Dorsey promised to spend three to six months living in Africa, only for later declare it an error, and set fire to having visited India and held a poster that read “smash the Brahmin patriarchy.”

After visiting Myanmar on a meditation retreat, he hailed it as “an absolutely beautiful country … [where] people are full of joy and the food is amazing. “Dorsey’s apparent ignorance of the country’s human rights abuses led to a shake-up on social media and a tweeted scolding from Andrew Stroehlein, the European media director for Human Rights Watch:” You forget to mention that you are in a country where the military has committed mass killings and mass rapes, forcing hundreds of thousands to flee, in one of today’s greatest humanitarian disasters… ”

Still, Bilton sees the billionaire’s let-it-all-hang-out style – as includes yachting trips with Jay-Z and Beyonce – as more calculated than it may seem.

“Dorsey really doesn’t care what people think, to a great extent,” Bilton said. “He wants them to think he wants a crazy legacy like Steve Jobs and put a dent in the universe. The jury is still out.”


Give a Comment