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How Jack Dorsey’s Plan to Get Elon Musk to Save Twitter Went South
An excerpt from Battle for the Bird shows how Twitter’s two most prominent leaders contributed to its current dilemma.
How Jack Dorsey’s Plan to Get Elon Musk to Save Twitter Went South
An excerpt from Battle for the Bird shows how Twitter’s two most prominent leaders contributed to its current dilemma.
Elon Musk was growing irritable on Friday evening, Nov. 4, 2022. It had been just over a week since he’d closed his $44 billion deal for Twitter, and advertisers were bailing on the company in droves. Many brand-conscious marketers were worried that Twitter’s historical reputation for nastiness would return as a result of Musk’s pledge to defeat the “woke mind virus,” his derisive term for the censorious attitude he felt had sucked the joy out of his favorite social network.
Musk said the way to save Twitter was to restore what he saw as freedom of speech. He hadn’t actually changed any of Twitter’s speech policies by that Friday, but the list of advertisers who had paused their Twitter ads already included United Airlines, REI and Volkswagen and was steadily growing. This was a major concern, considering Twitter made roughly 90% of its revenue from advertising.
Musk told his staff he couldn’t understand why things had already gone sideways. He’d spent his first full week as Twitter’s “Chief Twit” kowtowing to its most important advertising partners. He’d flown his Gulfstream to New York for a slate of meetings that included advertising industry heavy hitters like WPP’s Mark Read and Horizon Media’s Bill Koenigsberg. NFL Commissioner Roger Goodell had visited Twitter’s office in Chelsea, where Musk promised him in person that Twitter would still be a safe place for the league’s valuable highlight videos.
Now Musk was demanding answers. He called Robin Wheeler, his top sales executive, and asked how bad the business was. Wheeler had to be delicate. In a meeting a few days earlier, her predecessor had pushed back on Musk’s decision to tweet a joke about Donald Trump, and had been escorted out of the building by security just 24 hours later. It was clear Musk still didn’t appreciate just how anxious advertisers were about the new direction he was taking Twitter. He also seemed oblivious to how his own behavior was contributing to this feeling. One of the things that made Musk such a popular Twitter user was his lack of filter, but that was proving to be a liability now that he was the face of the operation.
Wheeler tried to explain this to her new boss by bringing up a tweet he’d posted just a few hours earlier in which he’d threatened to go “thermonuclear” on advertisers who stopped spending money on Twitter ads. “You don’t want to go to war with advertisers,” she warned.
“Oh, I will go to war,” he replied. “And I win wars.”
Wheeler also told Musk some Twitter users had begun harassing advertisers who were still running ads on the service in an attempt to get them to stop. Musk was incensed. Soon after his call with Wheeler ended, he sent her a text and included Yoel Roth, Twitter’s head of Trust and Safety, who managed the teams in charge of enforcing Twitter’s rulebook. “Yoel, please suspend all Twitter accounts that are engaged in harassment of our advertisers to get them to stop advertising on Twitter,” he wrote. “That is not OK.”
Pressuring an advertiser to stop spending money was certainly not against Twitter’s rules—it wasn’t even unusual. Suspending Twitter users for doing so would be impossible to justify under the company’s rules, and it certainly didn’t align with Musk’s stated pledge to uphold free speech. But Musk made clear that if the company didn’t have the rules he needed to exert his will, he’d create them. He then called Roth shortly after sending the text and spent the brief conversation ranting that trolling Twitter’s advertisers was akin to blackmailing the company. “Blackmail is against our rules now,” he declared.
Roth hung up and contemplated quitting right then and there. Instead, he called Wheeler and asked her to talk Musk off the ledge. Wheeler succeeded, and Musk quickly moved on to other problems. But the strains that have defined Musk’s tenure ever since were already emerging in those first few weeks on the job, according to several people familiar with Musk’s interactions and decisions at the time, who spoke on the condition of anonymity to avoid retaliation. Within that first week, he was learning how his stated principles of absolute free speech didn’t mix well with an advertising business. And the people trying to help him implement his vision were learning how quickly the new boss would abandon those principles once they didn’t work in his favor.
Nobody understood the tension inherent in running Twitter better than Jack Dorsey, who’d helped start the company, served two stints as chief executive officer and played a role in orchestrating Musk’s acquisition. As the deal with Musk came together, Dorsey, who still sat on Twitter’s board, texted and spoke with him regularly, according to private messages included in court documents related to litigation over the acquisition. Dorsey shared his concerns about Twitter’s reliance on advertising revenue and told Musk the company would be better served if it was no longer publicly traded. “It can’t have an advertising model,” Dorsey texted in March 2022, weeks before Musk first made his offer. “Otherwise you have a surface area that governments and advertisers will try to influence and control. If it has a centralized entity behind it, it will be attacked.”
Dorsey’s own tenure at Twitter hadn’t always gone smoothly, and he believed that if anyone could fix Twitter’s problems, it was Musk. But if Dorsey’s analysis of Twitter’s flawed business model was spot on, his solution has missed the mark. Musk engulfed Twitter in chaos even before he took over. After agreeing to buy the company in April 2022, Musk had a change of heart and tried to torpedo his own deal. He spent much of the year fighting with Twitter in court. When he abandoned his legal fight and reluctantly closed the deal that October, he immediately fired half the employees, including most of the executive team Dorsey had hired and worked with for years.
This bumpy start was a taste of things to come. About 16 months into the Musk era, the company’s revenue is now just a fraction of what it was before he arrived. Musk’s plan to restore free speech to the service—which he presented as a straightforward hands-off policy—has come with all kinds of asterisks and stumbles.
Dorsey has acknowledged that his attempt to hand off the company has been bungled. In April 2023, he spent some time responding to questions about Twitter on Bluesky, a competing social network he’d helped envision long before Musk ever entered the picture. Jason Goldman, an early Twitter board member, asked Dorsey a simple but loaded question: “Do you think Elon has proven to be the best possible steward” for Twitter?
Dorsey, as he tends to do, answered earnestly. “No,” he wrote back. “Nor do I think he acted right after realizing his timing was bad. Nor do I think the board should have forced the sale.
There was already plenty of upheaval at Twitter by the time Musk showed up with $44 billion in early 2022. In the two years leading up to the acquisition, activist investors tried to push Dorsey out; Twitter permanently banned a sitting US president; the company set a series of lofty financial goals it never came close to hitting; and Dorsey mentally checked out before resigning as CEO in November 2021. The conditions were ideal for someone like Musk to swoop in and take advantage.
Dorsey was eager to woo Musk, a business leader he greatly admired—and someone he often referred to as his favorite tweeter. Dorsey had tried unsuccessfully to get Musk to give a companywide pep talk in 2018, and then succeeded in getting him to do so in 2020. In 2021 Dorsey visited Musk at his Texas rocket launch facility, Starbase, and brought along his friend, the music producer Rick Rubin.
Dorsey and Musk kept an open dialogue as the acquisition was coming together, and Dorsey ultimately retained his nearly $1 billion stake in Twitter when Musk took it private. When the terms of the deal were finalized, Dorsey cheered publicly, and congratulated Musk privately. “I basically followed your advice!” Musk texted Dorsey just minutes after the deal was announced in April 2022. “I know,” Dorsey replied, “and I appreciate you.”
The day after, Dorsey sent Musk a private message in hopes of setting up a call with Parag Agrawal, whom Dorsey had hand-picked as his own replacement as CEO a few months earlier. “I want to make sure Parag is doing everything possible to build towards your goals until close,” Dorsey wrote to Musk. “He is really great at getting things done when tasked with specific direction.”
Who’s Held the Top Seat at Twitter
Photos: Bloomberg (4), Alamy (2), Getty Images (1)
Dorsey drew up an agenda that included problems Twitter was working on, short-term action items and long-term priorities. He sent it to Musk for review, along with a Google Meet link. “Getting this nailed will increase velocity,” Dorsey wrote. He was clearly hoping his new pick for owner would like his old pick for CEO.
This was probably wishful thinking. Musk was already peeved with Agrawal, with whom he’d had a terse text exchange weeks earlier after Agrawal chastised Musk for some of his tweets. Musk had also unsuccessfully petitioned Agrawal to remove a Twitter account that was tracking his private plane; the billionaire started buying Twitter shares shortly after Agrawal denied his request.
So it was no surprise that the call Dorsey arranged was a disaster. Agrawal’s vision for Twitter fell flat with his soon-to-be boss. There was a particularly uncomfortable moment that centered on Vijaya Gadde, Twitter’s top lawyer and policy exec, who had been deeply involved in decisions to ban Trump and block a news story about Joe Biden and his son Hunter in the final days of the 2020 presidential election. Musk saw Gadde as representing everything he disliked about Twitter’s speech policies, and he demanded that Agrawal fire her. Agrawal refused. It wasn’t clear if such an action would be appropriate, given that Musk didn’t own the company yet and wasn’t supposed to be making demands.
Dorsey didn’t jump in to defend Gadde, with whom he’d worked for the better part of a decade, nor did he advocate for his colleagues afterward. “You and I are in complete agreement,” Musk wrote to Dorsey after the call ended. “Parag is just moving far too slowly and trying to please people who will not be happy no matter what he does.”
“At least it became clear that you can’t work together,” Dorsey replied. “That was clarifying.”
The phone call telegraphed Musk’s willingness to clean house. Once he formally took over, he fired people on a whim, bad-mouthed Twitter’s business and publicly attacked those employees who disagreed with him. Musk eliminated the Covid-era policy of granting mental health days and required everyone back in the office full time.
He also abandoned the system Twitter used to verify prominent users and eliminated many of the company’s fact-checking operations. Twitter had leaned hard into fact-checking and other content moderation policies in 2020 as the rise of Covid-19 and the contentious US presidential election led to widespread misinformation on the service; Musk quickly reversed that approach, offering users more freedom to say whatever they wanted but damaging Twitter’s reputation as the go-to place for breaking news in the process.
For all his flaws as a businessman, Dorsey had made working at Twitter feel special, preaching to employees the power of the service and its place in the world. Many Twitter employees accepted less money than they could have made at other major tech companies such as Meta Platforms Inc. or Alphabet Inc.’s Google because Dorsey helped instill the sense that Twitter was more than another company selling targeted ads. Dorsey routinely told Twitter employees that he loved them, and for many years those feelings were reciprocated.
That connection was essentially severed as Dorsey held firm in his support for Musk while the new owner dismantled the company. While Dorsey didn’t directly object to Musk’s approach, he acknowledged its impact. Shortly after Musk fired half of Twitter’s employees just one week after taking over, Dorsey sent a melancholy tweet of apology. “I am grateful for, and love, everyone who has ever worked on Twitter,” he added. “I don’t expect that to be mutual in this moment … or ever … and I understand.”
A lot has happened since Musk first walked into Twitter’s San Francisco headquarters carrying a porcelain sink and a plan to turn the company inside out. Working with the skeleton crew that remains after laying off or running off most of the nearly 8,000 employees, he’s aiming to transform Twitter into an “everything app” where people can shop, tweet, find dates and manage their money.
Musk changed Twitter’s official name to X in July 2023. “The Twitter name made sense when it was just 140 character messages going back and forth—like birds tweeting,” he wrote that month. As an everything app, X will be something different entirely, Musk has said, and “so we must bid adieu to the bird.”
In the meantime, X’s advertising business continues to suffer from his commitment to tweeting whatever he wants whenever he wants. In April, Musk changed his Twitter username to “Harry Bolz.” In July he called Meta CEO Mark Zuckerberg a “cuck” and then challenged him to a “literal dick measuring contest.”
In November he posted support for an antisemitic tweet, which was the final straw for some major advertisers including Apple Inc. and Walt Disney Co. Musk offered an apology from the conference stage at DealBook a few days later, but didn’t put much effort into coming off as particularly apologetic. “Go f--- yourself,” he announced to boycotting advertisers just minutes later from that same stage.
Musk’s approach seems self-defeating, given that advertising still makes up roughly 75% of his company’s revenue. Unlike Meta and Google, which have enormous direct-response advertising businesses whose clients are often small businesses, Twitter is mostly dependent on brand advertising—the type of ads that stalwarts such as Coca-Cola, Apple and Disney use to shape their public image without necessarily expecting immediate sales.
Before the antisemitic tweet and the DealBook conference, X’s target for advertising revenue in 2023 was about $2.5 billion, or just over half what the company made in the last full year before Musk bought it, according to people familiar with X’s business, who didn’t want to be named as they weren’t authorized to speak publicly for the company. At the DealBook conference, he blamed advertisers who were reluctant to spend on X for the company’s financial issues. “What this advertising boycott is gonna do is it’s gonna kill the company,” Musk said. “And the whole world will know that those advertisers killed the company.”
Of course, it won’t be Disney’s fault if X fails. That will fall on Musk’s shoulders, because of his unwillingness to adjust to the realities of running an advertising business. X operates differently from companies such as Tesla Inc. and SpaceX, where he’s had such success. A global speech platform can’t be fixed or perfected simply by writing better code, improving manufacturing processes or pushing employees to work longer hours.
“I learned a ton from watching Elon up close—the good, the bad and the ugly,” tweeted Esther Crawford, a product executive who survived a few months under Musk before she was laid off in a round of cost cuts last February. “His boldness, passion and storytelling is inspiring, but his lack of process and empathy is painful.
“Elon has an exceptional talent for tackling hard physics-based problems,” she continued, “but products that facilitate human connection and communication require a different type of social-emotional intelligence.”
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Dorsey rarely tweets anymore, and when he does, it’s often related to his personal interests, which include Bitcoin, music and supporting the presidential campaign of Robert F. Kennedy Jr. It’s easy to see, though, that he hasn’t gotten what he envisioned when he encouraged Musk to buy his company.
Dorsey made a lot of the idea that one of Twitter’s flaws was it had too much power and control over global speech, and that the world would run better if such power was distributed. When it comes to what is said on X, there’s still a company holding the power, but that company is controlled by the richest man in the world with no board of directors, no public shareholders and seemingly no concerns about creating globally significant speech policies on a whim.
In an interview with the online political show Breaking Points in June, Dorsey admitted that the Musk era had gone wrong even before it officially started, when Musk accused the company of lying about how many users it had and Twitter responded by suing him. “I think it set up a dynamic where he had to be very hasty, he had to be impatient, he had to move as quickly as possible with features even if they weren’t fully thought out,” Dorsey said. “It all looked fairly reckless.”
Still, Dorsey maintained something that many of his former colleagues have long since abandoned: hope. “I do have confidence that he’ll figure it out,” he continued. “I own 3% of this new company, so I’m supportive.”
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