If there was a moment when Jack Dorsey first turned 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 platform social media platform that he co-founded. “I trust in his mission to extend the light of consciousness,” Dorsey posted last April on the site.
These rousing claims were the culmination of a years-long “bromance” between the two Silicon Valley billionaires, which fundamentally changed the future of Twitter. Dorsey, according to court documents and people familiar with the matter, was instrumental in welcoming the $44 billion sale of the platform to Musk, which has since bid farewell to 90% of its workforce and significantly relaxed its moderation policies.
Now, that alliance appears to have come to an end.
This week, Dorsey spoke out publicly against Musk, saying he didn’t believe the Tesla boss “did it right” in his handling of Twitter. “Everything has gone south,” wrote the 46-year-old, who he reversed his stake when Musk took Twitter private, making him one of its largest shareholders. “But it happened and all we can do now is build something to prevent it from happening again.”
Indeed, Dorsey — whose guru-like persona previously gained him devotees within Twitter — has led the charge to create alternatives to it. In the last week, Twitter lookalike Blue sky, which Dorsey seed funded in 2019 while still at the helm of Twitter, has made headlines by attracting journalists in droves along with politicians and the occasional celebrity. She remains on her board and has made her comments about Musk on the platform.
Thursday, Dorsey donated $5 million to “foster the new and grow. . . ecosystem” by Nostr, another decentralized social media project, later giving 14 bitcoins, worth more than $200,000, to its founder in December.
Those close to Dorsey say Nostr has been his main focus lately. Recognizable by his long grizzly beard and penchant for wellness fads, Dorsey attended a Nostr conference in March at a yoga retreat in Costa Rica, eventually speaking to her to give his blessing to the initiative. “This is his mea culpa—this is him taking responsibility for him for what Chirping it ended up being,” said Greg Kidd, an early Twitter investor, who also participated.
Dorsey has come to regret Twitter’s reliance on advertisers and investors and the way it forced the platform to try to ramp up engagement to hit quarterly results, Kidd said. “The second time around, he might not repeat those mistakes. . . Jack is returning to his basic job.
Born in St Louis, Missouri, Dorsey, who is also a licensed massage therapist, helped start Twitter in 2006. He has had two stints as CEO, the most recent from 2015 through the end of 2021. Those close to him say he has always been motivated by the desire to democratize and decentralize services. In the case of Twitter, he has tried to democratize the media. He has also become obsessed with bitcoin and decentralized payments in recent years.
This approach spilled over into how Dorsey handled Twitter. Whenever she had to make a decision, she said she saw it as a “failure” of the company, preferring to let staff members brainstorm the ideas for themselves. But it was this lack of a steady hand and resulting indecision, 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,” Kidd said.
Meanwhile, the man who made his millions off the site’s IPO has also turned against Wall Street itself, arguing that Twitter should never have been a company answerable to profit-hungry shareholders, but a “protocol.” owned by no single company or state.
When he resigned, staff members and even board members felt that Dorsey had become an “absent landlord” who had already given up on taking care of the platform. But his greatest betrayal, according to many former employees, was that he paved the way for the acquisition of Musk and publicly criticized the board as inadequate without taking responsibility for his role.
According to his defenders, it is only natural that Dorsey, an advocate of free speech, is now focused on developing the decentralized social media models of Bluesky and Nostr, whereby the goal is to build an interoperable system in which no central authority has the check.
“A lot of people think that the amount that pushed for Elon to take over. . . messed with its legitimacy,” said Evan Henshaw-Plath, an acquaintance and former colleague of Dorsey’s, adding that he thought this criticism was unfair. Now, however, Henshaw-Plath says, “I think there is some desire to be active in funding these alternatives like screw you to both Wall Street and Elon Musk.”
For Twitter 1.0 staffers, who felt sorely betrayed by Dorsey, recent criticism of Musk was slow in coming. Some expect his former acolytes to return as time goes on. “I think 1.0s have a short memory and will move forward quickly as they find new jobs,” said a former Twitter senior staffer. “And I will come back to savor it.”
But for Dorsey to salvage his wider reputation as a social media entrepreneur, a lot depends on whether his new ventures catch on or are just another fad. A current Twitter staffer said, “Time will tell if this is another one of Jack’s big ideas that never gets shipped properly before he moves on to the next brilliant thing.”
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