Late last year, Linda Yaccarino reached out to Don Lemon’s agent with an offer.
Ms. Yaccarino, the chief executive of X, a powerhouse advertising executive who had been hired away from NBC about seven months earlier, pitched the agent on bringing the former CNN anchor’s new web-based show to the social media platform, citing its massive reach, political influence and connections with advertisers. Soon after, Mr. Lemon became one of the first high-profile names to sign onto Ms. 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 Mr. Lemon’s first guest.
The interview was held at the Tesla headquarters in Austin, Texas, which, Mr. Musk quickly pointed out to Mr. Lemon, was “about three times larger than the Pentagon.” The two men sat on white Eames-like swivel chairs, a small white table between them. Mr. Musk was in a black T-shirt, Mr. Lemon in a white spread-collar shirt and a dark blue sweater.
The interview started out awkwardly, with Mr. Musk acknowledging that he hadn’t really watched Mr. Lemon when he anchored a 9 p.m. show on CNN. (“I’ve seen a few segments.”) It grew increasingly contentious over the next hour, and Mr. Musk became visibly frustrated with questions about his politics and drug use. “It’s pretty private,” Mr. Musk said when Mr. Lemon asked him about his prescription for ketamine, which Mr. Musk had posted about on X in 2023.
Mr. Lemon brought up complaints of sexual harassment at Tesla and SpaceX, both run by Mr. Musk, then asked if he had advantages in society as a white man. Mr. Musk raised an eyebrow. “You keep putting words in my mouth,” he objected. And when Mr. Lemon asked about the advertiser exodus from X, Mr. Musk shook his head: “Don, I have to say, choose your questions carefully. There’s five minutes left.” As the interview ended, Mr. Musk shot up from his chair, offering an abrupt handshake to the anchor.
The next day, he texted Mr. Lemon’s agent: “Contract canceled.”
A day after Mr. Musk called off the deal, Ms. Yaccarino called Mr. Lemon to find out what went wrong. She seemed confident she could patch things up between him and her boss. But Mr. Musk remained firm; Mr. Lemon had to be dismissed. The deal died — and with it, yet another attempt by Ms. Yaccarino to chart a profitable course for the troubled site.
Time and again, Ms. Yaccarino has faced similar situations, as Mr. Musk is always one whim away from undoing her work. Ms. Yaccarino’s task of repairing and remaking X’s business over the past year has been complicated by Mr. 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 attack on Israel, for instance, Ms. Yaccarino told several major advertisers that she and X would work to fight antisemitism. The next month, Mr. Musk approvingly replied to an antisemitic theory on the site.
On Nov. 18, Ms. 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 Ms. Yaccarino sitting a few feet away, Mr. Musk went onstage at The New York Times’s DealBook Summit and used an expletive — three times — to tell advertisers in the audience that they could take their business elsewhere.
It’s almost like a game of corporate Whac-a-Mole, which Ms. Yaccarino is doing her best to master.
If Ms. Yaccarino is frustrated by Mr. 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 Mr. Musk operates (in that phone call to Mr. Lemon, she said X was “Elon’s baby”) and that they have enough of a shared vision for X that she can grit her teeth and bear it. Over and over, Ms. Yaccarino has defended Mr. Musk’s actions behind the scenes.
“The mark of a good C.E.O. is not how many punches you can throw, but how many you can take. She is the Muhammad Ali of C.E.O.s,” said Ari Emanuel, the chief executive of the entertainment agency Endeavor, which is an investor in X. Mr. Emanuel is friends with Mr. Musk and speaks regularly with Ms. Yaccarino about X.
The company’s business has struggled in recent months, as advertisers remain hesitant. Since Mr. 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 percent of its U.S. advertising revenue, which dropped to $1.13 billion. The firm predicted X’s losses would slow to a 2.5 percent decrease this year.
X executives told employees last month that 65 percent of advertisers had reactivated their campaigns, although they appeared to be spending less than they once did. Internal documents obtained by The New York Times show that, in the second quarter of this year, X earned $114 million in revenue in the United States, a 25 percent decline from the first quarter and a 53 percent decline from the previous year. The company aims to reach $190 million in U.S. 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 percent less than they were last year.
Throughout all this turmoil, Ms. 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.
Ms. 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 Mr. 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.
“You have to know this about Linda: Quitting equals failure, and Linda cannot allow herself to fail,” said Lou Paskalis, a longtime ad executive and former friend who has cut ties and publicly rebuked Ms. Yaccarino for sticking by Mr. Musk. “She is cashing in her sterling reputation to be Elon’s chief apology officer.”
Ms. Yaccarino and Mr. Musk did not respond to requests for interviews.
Rising Through the Ranks
Ms. Yaccarino grew up on Long Island in New York, where her father was an assistant police chief and her mother was a civil servant. Her twin sister became a nurse and now runs her own health care company, and their older sister was a director at Deutsche Bank before retiring.
Ms. Yaccarino attended Pennsylvania State University and met her husband, Claude Madrazo, shortly after graduating in 1985. The couple have two children, a son and 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 Mr. O’Brien to appear in commercials, an early iteration of influencer marketing. When Turner secured the rights to “Sex and The City” from HBO, Ms. Yaccarino pitched it to brands as a “virtual original,” arguing that many Americans would be seeing the show for the first time when it landed on cable, recalled David Levy, the former president of Turner.
“She was a great leader, people loved to work with her. She was demanding, no question. That was what made her great. She worked harder than anyone else, and clients liked to be with her,” Mr. Levy said. “Linda was brash, out there, aggressive. And dominating.”
Her success convinced Steve Burke, then the chief executive at NBCUniversal, to hire her in 2011. She forged relationships with top marketers and on-air celebrities like Paris Hilton.
To develop her personal brand, Ms. Yaccarino hired communications specialists. In flashy presentations at the upfronts, an annual advertising event, she positioned television as the antithesis to Big Tech. “No family has ever gathered around a news feed,” she said onstage in 2018. “We’re not in the likes business — we’re in the results business.”
The next year, Mr. Burke at NBCUniversal started succession planning so that he could step back from his chief executive role. Eyeing an opportunity, Ms. Yaccarino gunned for a promotion, three people who worked with her said. But she didn’t get it. Ms. Yaccarino next made the argument that Comcast cable ad sales should be added to her portfolio. Again, she was denied by NBC leadership.
Ms. Yaccarino was an adroit negotiator who kept revenue rising even as ratings and viewership declined, those former colleagues said. But some argued she wasn’t detail oriented enough to run a business, something others close to her dismissed as sexism, noting that the male executives she worked with sometimes teased her about her outfits, a sore subject for Ms. Yaccarino. An NBC spokesman did not respond to a request for comment.
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.”
Still, she was a fiercely competitive saleswoman who took pride in getting better deals than executives at other networks did. “There is probably no better person that Elon could have hired to restore advertising on X,” Mr. Paskalis said.
In October 2022, Ms. 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 Ms. Yaccarino to consider a career change. Coincidentally, Mr. 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 Mr. Musk’s “free speech” pledge. At the time, Ms. 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 Mr. Musk to discuss advertiser worries, during which he promised a safe environment.
Some top ad agencies recommended clients pause spending on Twitter until Mr. Musk determined how to police offensive content. Ignoring that advice, Ms. Yaccarino contacted Mr. Musk to pledge NBCUniversal’s continued advertising and to decry 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.
Mr. Musk soon laid off more than 75 percent 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 Mr. Musk is chief executive, were plummeting. Investors questioned whether Mr. Musk was too distracted with Twitter to oversee the carmaker. On Dec. 20, Mr. Musk announced he was seeking a C.E.O. “foolish enough to take the job” to replace him at his social media company.
Mr. Musk and Ms. Yaccarino were in touch in early 2023 about NBC Universal running ads on X during the Super Bowl, and then started speaking more regularly. Ms. Yaccarino invited him to appear at the POSSIBLE advertising conference in Miami that April. “You challenge legacy, you challenge habits,” she told Mr. Musk during an onstage interview.
He asked advertisers to return. “If somebody has something hateful to say, it doesn’t mean you should give them a megaphone,” Mr. Musk said. “They should still be able to say it — but Twitter shouldn’t amplify it.”
On May 11, Mr. Musk posted that he had selected a chief executive. It was Ms. Yaccarino.
Ms. Yaccarino, who was in the middle of preparing for another upfronts presentation, hadn’t yet told her NBCUniversal colleagues about the job offer, and began receiving text messages asking if she was Mr. Musk’s pick. She rushed home from the company’s studios.
Many of her longtime peers in the advertising world were shocked that Ms. Yaccarino accepted the job — they feared she would tarnish her reputation by associating herself with Mr. Musk. But several colleagues who worked with her at X said she and Mr. 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.
Goodbye Twitter, Hello X
When Ms. Yaccarino took the helm on June 6, 2023, she confronted an immediate crisis: Mr. Musk’s unconventional cost-cutting methods had resulted in a stack of unpaid rent, utility and software bills. She brought her most trusted deputy, a communications executive named Joe Benarroch, with her from NBCUniversal to help with the mess. (In a move that surprised many, Ms. Yaccarino abruptly fired Mr. Benarroch last month, having him escorted out of X’s New York office.)
In her early days, Ms. Yaccarino renegotiated a cheaper contract with Google Cloud, which helped host Twitter’s services. She resumed payments for databases and software that helped the company detect and remove child sexual exploitation material. And, at one of the company’s international offices, she settled an unpaid heating bill. Before that, employees wore jackets indoors and tried to heat the space using a kitchen pizza oven.
She found a cadence with Mr. Musk, overseeing sales and partnerships while he controlled technology. They both weighed in on decisions about moderating content, although Mr. Musk made the final calls. Still, advertisers were spending in spits and starts.
Ms. Yaccarino met with several advertisers and researchers in June 2023 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 chief executive 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.
“The challenge you face will soon become an even more acute concern when you implement your plans to ‘revenue share,’” Mr. Ahmed wrote. “This will present a real moral challenge to advertisers who know that the money they give you goes directly to people like Andrew Tate and a rogue’s gallery of homophobes, racists and snake oil salesmen.” (Mr. Tate, a manosphere influencer who is facing criminal accusations over sexual misconduct, has more than 9.5 million followers on X.)
Ms. Yaccarino’s team didn’t reply to Mr. Ahmed’s email. He later went on to publish research showing that hate speech and misinformation were rising on the platform.
Within weeks, Ms. Yaccarino suggested to Mr. Musk that Twitter sue the C.C.D.H. The resulting lawsuit, filed in late July, claimed that the C.C.D.H. 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, Mr. Musk renamed Twitter as X. Although he had spoken publicly about wanting to turn the company into X, an “everything app,” he announced the rebranding abruptly on social media without warning Ms. Yaccarino that it was coming, a person familiar with the matter said. Ms. Yaccarino, who learned about the name change from Mr. Musk’s online posts, later said it signified the creation of an entirely new company.
Groups including the Anti-Defamation League were pressuring Mr. Musk to remove antisemitic content from X. Mr. Musk introduced Ms. Yaccarino to Jonathan Greenblatt, the A.D.L.’s director. “We had previously had what I would characterize as a good relationship,” Mr. Greenblatt said of his connection to Mr. Musk.
During their discussion, Ms. Yaccarino pledged to crack down on hate speech. “Linda and I had a very cordial and constructive conversation,” Mr. Greenblatt recalled. At the behest of an X policy team member, Mr. 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 Mr. Musk to ban the A.D.L. from X. A hashtag calling for a ban spread rapidly, and Mr. Musk replied to several posts about it, then threatened to sue the A.D.L.
Mr. Greenblatt quickly struck back. “I am not daunted. I am not deterred. I am not frightened. I am going to continue to ferociously fight antisemitism,” the A.D.L. director said.
The episode lent credence to the theory that Mr. Musk was boosting hate speech and that his C.E.O. was powerless to stop him. Ms. Yaccarino worked to undo the damage, setting a meeting at One World Trade Center with Anna Wintour, the editor of Vogue and chief content officer of Condé Nast. The company spends tens of millions of dollars on advertising on X a year.
Ms. Wintour told Ms. Yaccarino that she had worked well with Mr. Greenblatt, implying that the feud with the A.D.L. would need to stop, according to two people with knowledge of the conversation. Ms. Yaccarino was reassuring: X wouldn’t tolerate antisemitism, she promised.
Condé Nast kept advertising, and the A.D.L. later resumed spending, too.
On Sept. 28, Ms. Yaccarino arrived in Laguna Niguel, Calif. to speak at CODE, an annual tech and digital media summit. But as she arrived in the green room at the Ritz Carlton, she was blindsided by the news that a former Twitter trust and safety executive, Yoel Roth, had been added as a last-minute speaker at the conference.
Mr. Roth had quit the company in the wake of Mr. Musk’s takeover and penned an editorial in The New York Times that sharply questioned some of the actions being taken by the new owner. Mr. Musk responded by engaging with an online harassment campaign against Mr. Roth that accused the former executive of inappropriate conduct. Mr. Roth warned Ms. Yaccarino from the stage that Mr. Musk might someday turn on her, too.
Julia Boorstin, a CNBC anchor who was scheduled to interview Ms. Yaccarino, apologized backstage for the sudden change of plans and coaxed her not to cancel her appearance. When they took the stage that afternoon, both appeared rattled. The tense interview that unfolded shocked the audience — Ms. Yaccarino stumbled over basic company stats and fixated on Mr. Roth’s earlier interview, a dramatic fumble after her many skilled presentations to advertisers at previous upfronts.
When Ms. Boorstin asked for her response to Mr. Roth, Ms. Yaccarino said, “Chuckles. Chuckling.” But then continued to dispute his claims about the safety of the platform. When Ms. Boorstin tried to redirect her to talking about X, Ms. Yaccarino complained: “Yoel had 25 minutes to talk.”
Her appearance quickly spread on social media, all but drowning out her optimistic assertion that X would be profitable by early 2024. On the site itself, it observers called it a “dumpster fire” and a “train wreck.”
Afterward in the green room, tensions boiled over. Ms. Yaccarino confronted Ms. Boorstin, then rushed to the white Tesla waiting outside to whisk her away, Ms. Boorstin trailing behind in tears.
The disastrous interview capped Ms. Yaccarino’s most tumultuous month on the job. Afterward, she retreated, canceling another public appearance at a Wall Street Journal conference and rehearsing endlessly for congressional testimony she was set to present in January.
A new threat arose as Hamas attacked Israel on Oct. 7, and violent images from the resulting conflict spread rapidly on X. Ms. Yaccarino held daily meetings with X staffers grappling with content moderation in the politically fraught environment. But, on Nov. 15, Mr. Musk yet again seemed to undermine Ms. 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. Making matters worse, the advocacy group Media Matters for America released research on Nov. 16 showing ads on X adjacent to neo-Nazi posts.
‘Get Comfortable’
On Nov. 18, during a conference call, several longtime advertising executives spoke to Ms. Yaccarino about their concerns with Mr. 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 Mr. Musk’s comment was out of line.
In a meeting with X sales employees days later, Ms. Yaccarino said the conference call amounted to sabotage, trying to disrupt plans for her daughter’s upcoming wedding. “I am quite sure that that was not a coincidence,” she told her colleagues.
Later that month, Mr. Musk admitted that endorsing an antisemitic conspiracy theory had been a mistake. But then came that expletive-ridden screed against advertisers at The Times’s DealBook Conference, again bedeviling Ms. Yaccarino’s efforts to calm the waters.
For once, Ms. Yaccarino seemingly had enough.
That evening, she and one of Mr. Musk’s trusted confidants called him, making it clear that his onstage outburst had not been helpful. Ms. Yaccarino insisted that Mr. Musk had to smooth things by attending a dinner that night hosted by WPP, a giant advertising holding company. At first, Mr. Musk resisted, arguing he did not want to beg for money, two people said.
Ms. Yaccarino remained firm: Mr. Musk had to attend the dinner, she told him. He finally agreed.
Attendees welcomed Mr. Musk, and he ended up in a friendly chat with Mark Read, the chief executive of WPP, giving Ms. Yaccarino a rare chance to demonstrate her ability to influence Mr. Musk when it was crucial that she do so.
A few months later, as part of the technology conference CES in Las Vegas, a private dinner attracted more than 40 people, including curious marketing executives from Salesforce, the National Football League and the computer company Lenovo. Ms. Yaccarino, who hosted, had a message: “Get comfortable.” Mr. 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.
“I was left with a strong impression that she is very much in charge of running the business-side operation,” said Brendan Carr, a Republican commissioner for the Federal Communications Commission who attended the dinner. “She’s really articulating this vision that X can be a place for robust, wide open debate.”
The Biden Announcement
If advertisers hoped Ms. Yaccarino might waver in her support of Mr. Musk’s “anything goes” vision, the recent developments in the 2024 presidential campaign put an end to all that.
In late April, Ms. Yaccarino told colleagues that she would team up with the cable channel NewsNation to host a live-streamed presidential debate on X. Ms. Yaccarino later shifted to a town hall format that would allow former President Donald J. Trump and Robert F. Kennedy, Jr., to respond to questions from X users. No date has yet been set, but Mr. Musk has been eager for X to play a role in the presidential race.
In the last few weeks, he has made clear his full-throated support of Mr. Trump. Roughly 30 minutes after the former president was shot and injured at a rally in Pennsylvania on July 13, Mr. Musk backed his bid for the White House. “I fully endorse President Trump and hope for his rapid recovery,” Mr. Musk wrote on X. (His political leaning seems to dovetail with Ms. Yaccarino’s — she served on a presidential commission during Mr. Trump’s last term and currently follows several Melania Trump fan accounts on X.)
The internal documents about X’s revenue show that Ms. Yaccarino hopes to net $8 million in political advertising this quarter. If she succeeds, it would represent a marked increase from the company’s political earnings when it was still Twitter — the company earned less than $3 million from political advertisers during the 2018 U.S. midterm elections, the last cycle before it banned political advertising.
And Mr. Musk seems to be backing up his words with the kind of influence that his enormous wealth can buy. A super PAC created by Mr. Musk and some of his closest allies has committed to spending tens of millions of dollars over the next few months to elect Mr. Trump.
As for X itself, the onslaught of political news has reminded the world of its potential, as when President Biden used the social media platform to announce he was dropping out of the presidential race.
That post from his official account — which got 106 million views over the subsequent 24 hours — gave Ms Yaccarino an opportunity for a victory lap. “X is where history happens,” she boasted in a repost of Mr. Biden’s announcement.
But what Ms. Yaccarino failed to mention — or was perhaps unaware of — was that Mr. Biden’s announcement had been posted almost simultaneously on the rival sites Instagram, Threads and Facebook.
The post How Do You Solve a Problem Like Elon? appeared first on New York Times.
