In the league of legends of Silicon Valley, Jack Dorsey — the co-founder of Twitter who stepped down as CEO a year ago this month — has long had a reputation as the cool hippie with the beard who likes to go off and meditate in between dating models and fasting.
Now, barely a week since his fellow billionaire businessman Elon Musk snapped up Twitter for $44 billion, Dorsey, 46, is launching a social media company called Bluesky: a new kind of decentralized platform that promises to give users and developers more autonomy. More than 30,000 subscribers have already signed up, the company tweeted on Oct. 20.
Bluesky, which is in the beta testing phase, was commissioned by Dorsey as an answer to some of the problems he saw at Twitter.
While some doubt there’s real interest in yet another social media company, those who know the never-married and childless Dorsey say he has sharp elbows in addition to brains, and that his life and career post-Twitter should not be underestimated. He is currently worth a little less than $4 billion.
In an apparent show of confidence in Musk’s takeover, Dorsey, who also founded the monetary-payment company Block, chose to roll over his $1 billion stake — 18 million shares — in Twitter rather than cashing out.
But, sources said, there is resentment among Twitter employees — half of whom are reportedly expected to lose their jobs under Musk.
“Jack is hated at Twitter,” a source familiar with the situation told The Post. “They blame what happened with Elon taking over the company on Jack. Parag [Agrawal, the recently-ousted head of Twitter] and the board think he is this really bad character.
“Just look at the stock price before Elon bought it. It was about $37 and had been flat for about ten years. The company hadn’t grown because Jack was gallivanting around on his jet with these models,” the source said. “But nobody wrote about what a disaster the company was because everyone idolizes Dorsey and thinks he’s the next Steve Jobs.”
Dorsey’s reps at Square and Bluesky did not respond to requests for comment.
Dorsey may not be a lightning rod for controversy like Musk, Jeff Bezos or Bill Gates, or be perceived as socially awkward like Mark Zuckerberg, but it’s a mistake to think he’s any less Machiavellian or megalomaniacal than the rest of them, several sources who know Dorsey told The Post.
“He was at one point the lowest person in the room at Twitter and then, because he wanted to be the most important person in the room, he was — and he ended up being CEO,” said author Nick Bilton, who spent time with Dorsey for “Hatching Twitter: A True Story of Money, Power Friendship and Betrayal,” his 2014 book.
“He had three co-founders who have sort of been erased from the history of Twitter, both publicly and financially. When he left this last time he blamed the problems at Twitter on other people. Even though he was on the board and was the CEO! He is incredibly adept at boardroom politics and fending off coups against him.”
And he has plenty of people in his corner who foresee a glowing post-Twitter career in his future.
“Jack’s not hot-headed or hot-blooded,” said Nik Yakovenko, who worked at Twitter under Dorsey from 2015 to 2017. “He’s a calm person. A lot of [Silicon Valley bosses] are not calm. He is a bit more cerebral. He’s also a lot more sincere than you would think. He’s not that interested in money. He loves nature and the outdoors and he’s very into doing blockchain stuff. It remains to be seen what happens with Bluesky. It’s about decentralizing social media networks in the future to give users more autonomy.”
Like many of the big tech bros, Dorsey did not stand out during his childhood, where he suffered with a stutter and had geeky hobbies like studying maps and trains and listening to police scanners.
“I loved couriers,” he once said. “You had this transfer of physical information happening throughout the city and the world. Someone picking up the package, putting it in a bag, going somewhere, taking it out of the bag, giving it to someone else. I thought that was so cool. I wanted to map it, to see that flow on a big screen.”
He grew up in modest circumstances in St. Louis, Mo. where his father, Tim, was a medical equipment engineer and his mother, Marcia, a homemaker. The family recently renovated Marcia Dorsey’s childhood home.
Her Twitter bio reads: “Mother of @jack… Does that make me the grandmother of Twitter?”
Despite dropping out of college, Dorsey’s early foray into creating dispatch software for taxi companies led him to plan for microblogging his status to his friends in real time — an idea that served as the eventual building block for Twitter, formed in 2006.
Along the way Dorsey briefly became a licensed massage therapist and dabbled in modeling and fashion design.
In 2019, he detailed 11 of his “wellness habits” which include morning ice baths and saunas, eating just one meal a day and often fasting on weekends, two hours of meditation daily and a daily five-mile walk to work.
“Dorsey is a rarity in Silicon Valley,” Bilton said. “Jack’s more charismatic than most of them. Having a conversation with Mark Zuckerberg is talking to a chatbot. Most are odd and you think, did someone make them in a lab and did they then escape and become CEOs. But with Jack you sense there may be an actual human being in there somewhere.”
Dorsey’s charisma — and massive bank account — may be why he’s been linked to swimsuit models Flora Carter and Raven Lyn Corneil, yoga instructor Kate Greer, fashion model Lilly Cole and “Boss Bitch” author Nicole Lapin.
But the relationships haven’t lasted.
“He bought Raven Lyn an $8 million house in the Hollywood Hills in 2019 but she still broke up with him,” an insider told The Post. “It was like he was too weird to put up with despite his money.”
One Silicon Valley insider said Dorsey keeps a low profile. He first bought a $10 million home overlooking San Francisco Bay in the Seacliff area of the city in 2012 and then bought the property next door for $21 million in late 2018.
“Jack always seems to be the harbinger of things to come,” the insider told The Post. “His diet, biohacking, the fasting — he’s always one of the first ones to do stuff. What he does that seems weird will be seen as trendy and cool three years later … But he doesn’t participate in the social circuit or the galas. He stays away and sticks with his dude pack.”
His current dude pack, however, would be well advised, to watch their pal like a hawk.
“Jack doesn’t talk to any of [his three] Twitter co-founders anymore,” said another insider of Dorsey’s old friends Biz Stone, Evan Williams and Noah Glass. “You can be sure they don’t buy into the BS public narrative that Dorsey is some benign monk CEO walking the earth. He’s like all the rest of them, just trying to screw everyone else over for his own good.”
The Post has reached out to Stone, Williams and Glass.