How do you solve a problem like Elon Musk?

X CEO Yaccarino’s task of repairing and remaking the platform’s business over the past year has been complicated by Musk’s seeming disregard for the advertising industry and his constant unraveling of her efforts

Late last year, Linda Yaccarino reached out to Don Lemon’s agent with an offer.

Yaccarino, the CEO of X and an advertising powerhouse who had been hired away from NBC about seven months earlier, pitched the agent on bringing that former CNN anchor’s new web-based show to the social media platform, citing its sprawling reach, political influence and connections with advertisers. Soon after, Lemon became one of the first high-profile names to sign onto Yaccarino’s plan to help save the company’s sagging advertising business with video and TV-like programming.

Elon Musk, who owns X, agreed to be Lemon’s first guest.

The interview started out awkwardly, with Musk acknowledging that he hadn’t really watched Lemon when he anchored a 9 pm show on CNN. (“I’ve seen a few segments.”) It grew increasingly contentious over the next hour, and Musk became visibly frustrated with questions about his politics and drug use. “It’s pretty private,” Musk said when Lemon asked him about his prescription for ketamine, which Musk had posted about on X in 2023.

Lemon brought up complaints of sexual harassment at Tesla and SpaceX, both run by Musk, then asked if he had advantages in society as a white man. “You keep putting words in my mouth,” Musk objected. And when Lemon asked about the advertiser exodus from X, Musk shook his head: “Don, I have to say, choose your questions carefully. There’s five minutes left.”

The next day, he texted Lemon’s agent: “Contract canceled.”

A day after Musk called off the deal, Yaccarino called Lemon to find out what went wrong. She seemed confident she could patch things up between him and her boss. But Musk remained firm; Lemon had to be dismissed. The deal died — and with it, yet another attempt by Yaccarino to chart a profitable course for the troubled site.

Time and again, Yaccarino has faced similar situations, as Musk is always one whim away from undoing her work. Yaccarino’s task of repairing and remaking X’s business over the past year has been complicated by Musk’s seeming disregard for the advertising industry and his constant unraveling of her efforts, according to interviews with more than a dozen advertising executives, X employees, former colleagues and friends.

After the Oct. 7, 2023, attack on Israel, for instance, Yaccarino told several major advertisers that she and X would work to fight antisemitism. The next month, Musk approvingly replied to an antisemitic theory on the site.

On Nov. 18, Yaccarino called on advertisers to come back to X to show their solidarity with the social media platform’s commitment to free speech. Shortly afterward, in a fit of petulance, and with Yaccarino sitting a few feet away, Musk went onstage at The New York Times’ DealBook Summit and used an expletive — three times — to tell advertisers in the audience that they could take their business elsewhere.

If Yaccarino is frustrated by Musk’s actions, she isn’t showing it, at least not publicly. By all accounts, she seems to have accepted that this is the way Musk operates and that they have enough of a shared vision for X that she can grit her teeth and bear it. Over and over, Yaccarino has defended Musk’s actions behind the scenes.

The company’s business has struggled in recent months, as advertisers remain hesitant. Since Musk took the company private, it no longer publicly reports its earnings, but Emarketer, a market research agency, estimated that last year, X lost about 52 per cent of its US advertising revenue, which dropped to $1.13 billion. The firm predicted X’s losses would slow to a 2.5 per cent decrease this year.

X executives told employees last month that 65 per cent of advertisers had reactivated their campaigns, although they appeared to be spending less than they once did. Internal documents obtained by the Times show that, in the second quarter of this year, X earned $114 million in revenue in the United States, a 25 per cent decline from the first quarter and a 53 per cent decline from the previous year. The company aims to reach $190 million in US revenue during the third quarter, bolstered by advertising associated with the Olympics, football and political campaigns, the documents said — but that target would still set the company’s quarterly earnings at 25 per cent less than they were last year.

Throughout all this turmoil, Yaccarino seemingly remains resolute. “My job is to clear the path for you all to succeed and for X to become the world’s platform,” she said during a leadership meeting at X’s San Francisco office in May, according to two people who attended.

Yaccarino, 60, has forged a bond with her 53-year-old boss, chatting often by text message, according to one of the people, who, like many interviewed, spoke on the condition of anonymity to discuss sensitive details. Some of Musk’s friends have counseled her on how she should interact with the willful billionaire or even offered to act as an intermediary with him. More strikingly, some of her friends and former colleagues have begged her to quit.

Yaccarino and Musk did not respond to requests for interviews.

Yaccarino grew up on Long Island in New York. She attended Pennsylvania State University and met her husband, Claude Madrazo, shortly after graduating in 1985. They have a son and a daughter. (She hired her son, Matt Madrazo, to sell political ads at X.) She began her career at Turner Entertainment, where she worked in ad sales for nearly 20 years.

As she rose at Turner, her role expanded to include programming. She worked on the reboot of Conan O’Brien’s show after he departed NBC for TBS in 2010, hammering out ad deals that incorporated sponsored products into the program and lining up O’Brien to appear in commercials, an early iteration of influencer marketing.

Her success persuaded Steve Burke, then CEO at NBCUniversal, to hire her in 2011.

The next year, Burke started succession planning so that he could step back from his CEO role. Eyeing an opportunity, Yaccarino gunned for a promotion, three people who worked with her said. But she didn’t get it. She next argued that Comcast cable ad sales should be added to her portfolio. Again, she was denied by NBC’s leaders.

In a 2018 interview at Davos, she recounted the performance review she received before leaving Turner, in which she said her boss wrote approvingly of her work, but then added, “I only wish she would stop using her high heels as a weapon.”

The comment helped convince her it was time to leave the job, she said. “Today, you might put that under a byproduct of unconscious bias, because who would ever look at a man’s heels to say that’s why they are being aggressive or assertive or powerful.”

In October 2022, Yaccarino was in discussions with Netflix about an advertising partnership with NBCUniversal. The streaming giant instead suggested she come run ad sales, she told two of her former colleagues. While the job talks never went far, co-workers said it prompted Yaccarino to consider a career change. Coincidentally, Musk was then in the process of acquiring Twitter for $44 billion.

Within weeks of his takeover, hate speech flooded the platform as users tested Musk’s “free speech” pledge. At the time, Yaccarino was part of Twitter’s “Influence Council,” a group of advertisers advising the company on working with brands. The council, which was formed in 2015 under the former owners, joined a call with Musk to discuss advertiser worries, during which he promised a safe environment.

Some top ad agencies recommended clients pause spending on Twitter until Musk determined how to police offensive content. Ignoring that advice, Yaccarino contacted Musk to pledge NBCUniversal’s continued advertising and to denounce the pause in spending by others, two people familiar with the conversation said. She offered to help inform other marketers that their fears were overblown and convince them of the power of the platform.

Musk soon laid off more than 75 per cent of the company’s employees, including most who kept watch for problematic posts. He changed the platform’s rules and reinstated hundreds of previously banned accounts. Hate speech on the site surged, according to researchers tracking it, and more advertisers left.

By December, stock prices at Tesla, where Musk is CEO, were plummeting. Investors questioned whether Musk was too distracted with Twitter to oversee the carmaker. On Dec. 20, Musk announced he was seeking a CEO “foolish enough to take the job” to replace him at his social media company.

On May 11, Musk posted that he had selected a CEO. It was Yaccarino.

Many of her longtime peers in the advertising world were shocked that Yaccarino accepted the job; they feared she would tarnish her reputation by associating herself with Musk. But several colleagues who worked with her at X said she and Musk were more alike than their public personas might suggest. They share a fervent belief that their responsibilities range beyond running a viable business into rescuing the principle of free speech, a paranoia of sabotage from employees and associates, and a willingness to pursue legal action against critics.

Yaccarino took the helm June 6, 2023. She met with several advertisers and researchers that month to reveal her plan for protecting brands from unsavory content — tools which would allow advertisers to ensure that their posts did not appear next to specific keywords. X also planned to begin sharing ad revenue with popular users on the platform.

After the meeting, Imran Ahmed, the CEO of the Center for Countering Digital Hate, asked in an email if he could present research on the rise in hate speech on the site. He also expressed concern that the new tools wouldn’t protect advertisers, since ad dollars could still be funneled to hateful content creators through the revenue-sharing program.

Yaccarino’s team didn’t reply to Ahmed’s email. He later went on to publish research showing that hate speech and misinformation were rising on the platform.

Within weeks, Yaccarino suggested to Musk that Twitter sue the CCDH. The resulting lawsuit, filed in late July, claimed that the CCDH had harmed the company’s advertising business and that the group used improper methodology to gather its findings. (The suit was dismissed in March; X has appealed.)

In July 2023, Musk renamed Twitter as X. He announced the rebranding abruptly on social media without warning Yaccarino that it was coming, a person familiar with the matter said.

Groups including the Anti-Defamation League were pressuring Musk to remove antisemitic content from X. Musk introduced Yaccarino to Jonathan Greenblatt, the ADL’s director.

During their discussion, Yaccarino pledged to crack down on hate speech. At the behest of an X policy team member, Greenblatt said in a post on X that the conversation was “frank + productive” and that he would give “credit if the service gets better ... and reserve the right to call them out until it does.”

The post incited an immediate backlash. Nick Fuentes, a white supremacist livestreamer, and others campaigned for Musk to ban the ADL from X. A hashtag calling for a ban spread rapidly, and Musk replied to several posts about it, then threatened to sue the ADL.

Greenblatt quickly struck back. “I am not daunted,” he said. “I am not deterred. I am not frightened. I am going to continue to ferociously fight antisemitism.”

A new threat arose as Hamas attacked Israel on Oct. 7, and violent images from the resulting conflict spread rapidly on X. Yaccarino held daily meetings with X staff members grappling with content moderation in the politically fraught environment. But on Nov. 15, Musk yet again seemed to undermine Yaccarino’s efforts by endorsing the “great replacement” theory, an antisemitic conspiracy theory that minorities are replacing white European populations.

“You have said the actual truth,” he replied to a user who posted it on X.

On Nov. 18, during a conference call, several longtime advertising executives spoke to Yaccarino about their concerns with Musk’s seeming embrace of antisemitism and encouraged her to resign, two people familiar with the call said. She had a duty to her team, she responded, and she did not think Musk’s comment was out of line.

Later that month, Musk admitted that endorsing an antisemitic conspiracy theory had been a mistake. But then came that expletive-ridden screed against advertisers at the Times’ DealBook Summit, again bedeviling Yaccarino’s efforts to calm the waters.

A few months later, as part of the technology conference CES in Las Vegas, a private dinner attracted more than 40 people, including marketing executives from Salesforce, the NFL and the computer company Lenovo. Yaccarino, who hosted, had a message: “Get comfortable.” Musk’s vision of X as an anything-goes platform without strict content moderation wasn’t going to change, she said.

Of course, X would police hate speech and child exploitation, she assured the marketers. But Twitter, which was governed by a mandate of ensuring “healthy conversations” and policed its users’ toxic speech, was in the past.