If there was a moment when Jack Dorsey first morphed from Jesus to Judas in the minds of many former Twitter staffers, it was when he described Elon Musk as the “singular solution” to take over the social media platform he co-founded. “I trust his mission to extend the light of consciousness,” Dorsey posted last April on the site.
These gushing statements were the culmination of a years-long ‘bromance’ between the two Silicon Valley billionaires, one that dramatically altered the future of Twitter. Dorsey, according to court documents and people familiar with the matter, was instrumental in accommodating the $44bn sale of the platform to Musk, who has since said goodbye to 90 per cent of its workforce and dramatically relaxed its moderation policies.
Now, that alliance appears to have come to an end.
This week, Dorsey spoke out publicly against Musk, saying he did not believe the Tesla chief “acted right” in his handling of Twitter. “It all went south,” wrote the 46-year-old, who rolled his stake over when Musk took Twitter private, making him one of its biggest shareholders. “But it happened and all we can do now is build something to avoid that ever happening again.”
Indeed, Dorsey — whose guru-like persona previously won him devotees inside Twitter — has been leading the charge to create alternatives to it. Over the past week, Twitter lookalike Bluesky, which Dorsey seed funded in 2019 while still at the helm of Twitter, made headlines as it attracted journalists in droves alongside the occasional politician and celebrity. He remains on its board and made his comments about Musk on the platform.
On Thursday, Dorsey donated $5mn to “advancing the new and growing . . . ecosystem” of Nostr, another decentralised social media project, after giving 14 bitcoin, worth more than $200,000, to its founder in December.
Those close to Dorsey say that Nostr has been his main focus lately. Recognisable by his long grizzly beard and penchant for wellness fads, Dorsey attended a Nostr conference in March at a yoga retreat in Costa Rica, speaking at the end to give the initiative his blessing. “This is his mea culpa — this is him taking his responsibility for what Twitter ended up being,” said Greg Kidd, one of Twitter’s early investors, who also attended.
Dorsey came to regret Twitter’s reliance on advertisers and investors, and how it compelled the platform to try to juice engagement to meet quarterly results, Kidd said. “Second time around, he may not repeat those mistakes . . . Jack is getting back to his basic work.”
Born in St Louis, Missouri, Dorsey, who is also a licensed massage therapist, helped set up Twitter in 2006. He had two stints as chief executive, most recently from 2015 until the end of 2021. Those close to him say he has always been motivated by a desire to democratise and decentralise services. In the case of Twitter, he sought to democratise media. In recent years, he has also become obsessed with bitcoin and decentralised payments.
This approach spilled into how Dorsey ran Twitter. Every time he had to make a decision, he said he saw it as a “failure” of the business, preferring to allow staffers to thrash out ideas themselves. But it was this lack of steady hand and resulting indecision, his critics argue, that left Twitter plagued by slow innovation, briefly challenged by activist investor Elliott Management and ultimately vulnerable to Musk. “He believes, for better or for worse, in the wisdom of the hive mind,” said Kidd.
In the meantime, the man who made his millions through the site’s IPO also turned on Wall Street itself, arguing that Twitter should never have been a company answering to profit-hungry shareholders, but a “protocol” owned by no single company or state.
By the time he stepped down, staffers and even board members felt Dorsey had become an “absentee landlord” who had already checked out of caring about the platform. But his biggest betrayal, according to many former employees, was that he paved the way for Musk’s takeover, and publicly criticised the board as inadequate without taking responsibility for his own role.
Per his defenders, it is only natural that Dorsey, a free speech believer, is now focused on developing the decentralised social media models of Bluesky and Nostr, whereby the goal is to build an interoperable system where no central authority is in control.
“A lot of people think the amount he pushed for Elon to take over . . . messed up his legitimacy,” said Evan Henshaw-Plath, an acquaintance and former colleague of Dorsey, adding that he thought this criticism was unfair. Now, however, Henshaw-Plath says, “I think there is a bit of a desire to be active in funding these alternatives as a fuck you to both Wall Street and Elon Musk.”
For Twitter 1.0 staffers, who felt acutely betrayed by Dorsey, the recent Musk criticism was a long time coming. Some expect his former acolytes to return with the passing of time. “I think the 1.0 have a short memory and will move on quickly as soon as they land new jobs,” one former senior Twitter staffer said. “And will go back to relishing him.”
But for Dorsey to salvage his wider reputation as a social media entrepreneur, much rests on whether his new initiatives gain traction, or are just another fad. One current Twitter staffer said: “Time will tell if this is another of Jack’s big ideas that never gets properly shipped before he moves on to the next shiny thing.”