Jack Dorsey texted Elon Musk to say Twitter never should have been a company

Elon Musk’s $44 billion takeover of Twitter began in earnest in March. Musk had been tweeting about the social media platform’s problems while slowly amassing a large stake in the publicly traded social media company.

Jack Dorsey, who had stepped down as Twitter CEO a few months before, was frustrated, too.

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“A new platform is needed. It can’t be a company. This is why I left,” Dorsey texted Musk on March 26.

“Ok. What should it look like,” Musk responded.

“I believe it must be an open source protocol, funded by a foundation of sorts that doesn’t own the protocol, only advances it,” Dorsey said, likening his idea to the model adopted by the encrypted messaging app Signal.

Texts between the two men, who have been friends for years, were revealed through discovery in an ongoing court battle between Twitter and Musk over his attempts to abandon the binding agreement he signed to buy the company back in April.

The messages, which capture the two months from March to May in which Musk considered and executed the massive deal, cast him as an idol of Silicon Valley, swamped by sycophantic venture capitalists, friendly conservative ideologues, and opportunists. They also suggest Musk walked into the deal without fully considering that his goal for Twitter, to make it a beacon of unfettered speech, was incompatible with the company being a profitable business, as Dorsey had suggested in their March text exchange.

“I’m off the twitter board mid May and then completely out of the company. I intend to do this work and fix our mistakes,” Dorsey wrote. “Twitter started as a protocol. It should have never been a company. That was the original sin.”

“I’d like to help if I’m able to,” Musk responded.

But a few weeks later, after Musk had secured a seat on Twitter’s board, he decided to buy the company outright and take it private, bypassing Dorsey’s proposal that a foundation run the platform.

So while Musk’s original motives seemed to prioritize free speech, the deal he proposed required outside financing, further complicating the idea to free Twitter from its profit motives.

Elon Musk inches toward a takeover

By the end of March, Musk had acquired a 9% stake in Twitter, setting off a string of texts between company executives and the billionaire businessman.

Initial conversations between Musk, Twitter CEO Parag Agrawal, and board chairman Bret Taylor were friendly. On April 5, Dorsey texted Musk that he “couldn’t be happier” that Musk was joining the board. “I’ve wanted it for a long time. Got very emotional when I learned it was finally possible.”

But a few weeks later—after Musk tweeted “Is Twitter dying?—the tone of his conversations with Agrawal changed drastically.

“You are free to tweet ‘Is Twitter dying?’ or anything else about Twitter - but it’s my responsibility to tell you it’s not helping me make Twitter better in the current context,” Agrawal texted Musk. “Next time we speak, I’d like to provide you [with] perspective on the level of internal distraction right now and how [it’s] hurting our ability to do work. I hope the [ask me anything session with employees] will help people to get to know you, to understand why you believe in Twitter, and to trust you - and I’d like the company to get to a place where we are more resilient and don’t get more distracted, but we aren’t there right now.”

“What did you get done this week?” Musk asked. “I’m not joining the board. This is a waste of time. Will make an offer to take Twitter private.”

In follow-up messages with Taylor, Musk said, “Fixing twitter by chatting with Parag won’t work. Drastic action is needed. This is hard to do as a public company, as purging fake users will make numbers look terrible, so restructuring should be done as a private company.”

“This is Jack’s opinion too,” Musk? added.

The next time Dorsey texted Musk was on April 25 when Twitter’s board agreed to sell the company to Musk.

“Thank you <3” Dorsey wrote.

“I [am] basically following your advice,” Musk responded.

“I know and I appreciate you. This is the right and only path. I’ll continue to do whatever it takes to make it work,” Dorsey said.

Elon Musk didn’t understand the “original sin”

Musk’s offer was simple. He would pay $44 billion—equivalent to $54.20 a share—to buy Twitter and take it private.

But whether he misunderstood or ignored his friend Dorsey’s warning in the March texts that Twitter shouldn’t be run as a company, Musk failed to heed it.

In that exchange, Dorsey didn’t say that Twitter shouldn’t have been a public company, but that it shouldn’t be a company at all—with advertisers, revenue, and business incentives. It should have been a protocol, he said, something closer to Bluesky, the Twitter-funded social media project that Dorsey and Agrawal started working on in 2019.

Still, Dorsey seemed supportive of Musk’s deal regardless of this discrepancy and frustrated with Taylor and Agrawal. The former Twitter CEO arranged for a meeting between Musk and Agrawal on April 26 to “make sure Parag is doing every possible to build toward [Musk’s] goals until close.”

“I won’t let this fail and will do whatever it takes,” Dorsey said. “It’s too critical to humanity.”

But following the meeting it was clear that Musk and Agrawal were butting heads. “You and I are in complete agreement,” Musk texted Dorsey. “Parag is just moving far too slowly and trying to appease people who will not be happy no matter what he does.”

“At least it became clear you can’t work together,” Dorsey said. “That was clarifying.”

Musk’s deal was a miscalculation on his part—as evidenced by his willingness to air his dirty laundry in court to get out of it. At the end of the trial, which begins in Delaware later this month, Musk may be forced to not only pay Twitter damages, but to buy the company against his will.

Twitter could have been transformed from a public company to a private, one-man-owned protocol, stored away under the stewardship of a thoughtful foundation. But it wasn’t. That would’ve cost Musk $44 billion and, as it turns out, even the world’s richest person doesn’t want to lose $44 billion.