Toe-to-toe steers ‘Chief Twit’ from the brink

Ten minutes past midnight on a Monday in late November 2022, one of those crisp San Francisco evenings where the breeze sweeping up from the bay hit with the subtlety of a fist bristling with razor blades, Esther Crawford found herself in a dimly lit conference room, desperately trying to talk the richest man in the world out of starting the Silicon Valley equivalent of World War III. 

It was just the two of them, alone and next to one another at a ridiculously long, rectangular table that sliced through the centre of the tenth floor of Twitter’s main headquarters. Crawford had her laptop open in front of her, the screen casting a cone of light across her porcelain skin. 

Elon Musk, hovering over her right shoulder, was in shadow, his wide, square face, impish eyes, and ever-present smirk barely lit by the fluorescent ceiling panels high above. Beyond the table stood a wall of glass that had once looked out onto the bustle of the rest of the floor, an open design that encourages a collaborative culture that the company had once been known for. 

After choosing the space as one of his preferred roosts, one of the first things Musk had done was to frost the glass — unintentionally transforming the once-lively room into a dark, cave-like bunker. During the day, the change was subtle, a muted glow from the office beyond; but at night, ominous shadows crept over the ergonomic furniture and lacquered wood fixtures. 

Crawford had been in the bunker since noon. Though colleagues had filed in and out during the day, she had been mostly on her own since sundown, when the view from the windows on the other side of the room had shifted from a vibrant cityscape of marble, glass, and steel, and the San Francisco State House offset by a pincushion of office buildings, to little more than a sea of flickering lights struggling against an ink-black sky. She was hungry and tired and hadn’t slept more than a few hours over the past 48; she had just been contemplating heading home to her husband and three kids when Musk had wandered in, 10 minutes before, flanked by his two hulking bodyguards, who were now positioned just outside the conference room door, like oversized gargoyles. 

It wasn’t out of character for Musk to stop by the conference room without notice, even at odd hours of the evening. For weeks now, he’d been living in Twitter’s headquarters, sleeping on a couch in the library on the eighth floor until someone had carted a handful of beds up the service elevators for the billionaire and his team. Nor was it abnormal for him to meet one-on-one with Crawford, even though she wasn’t officially upper management, and before the takeover she had been low enough on the chain of command that she’d have more likely found herself with the gargoyles on the other side of the frosted glass. 

Her life had taken some dramatic turns in the past four weeks, since Musk had famously walked through Twitter’s front doors carrying a kitchen sink — “let that sink in” —and Crawford was now, arguably, one of the most important people at the company. She might not have officially been in Musk’s “inner circle”, which was comprised almost entirely of middle-aged men, friends from outside Twitter; but she was one of the few people left at the company who had a direct line of communication with the mercurial, self-described “Chief Twit”. 

That put her in the privileged, and often terrifying, position of being the person in the room tasked with steering Musk away from the edges of cliffs he seemed so particularly fond of racing toward. Tonight, it seemed, was going to be another one of those moments. He’d burst into the room, crossing the conference area in three determined steps. 

The nearest chair to Crawford had happened to be a miniature design piece that someone had wheeled over from a privacy alcove by the windows, and it took Musk an extra beat to stuff his boxy, 1.88-metre frame into the confining apparatus. With arms and legs tucked in front of him like a praying mantis, he’d launched right into it, continuing a conversation that had begun almost two days earlier. 

His tone had remained controlled, his volume low, but Crawford had been able to tell from the start that he was already headed toward that cliff. If she didn’t act quickly, there was a real chance he was going to barrel right over the edge. It didn’t help that the issue that had him so worked up at midnight on a Monday had begun as a simple misunderstanding. 

During the weeks she’d worked with the billionaire, she’d learned that at his core, he wasn’t driven by facts or expertise, but by instincts and intuition. Neither did it matter that in her heart, Crawford agreed with Musk’s take on the situation, and shared his frustration: the system he had run up against was clearly unfair, and possibly even legally untenable. 

But she was also certain that the decision Musk was heading toward, at breakneck speed, publicly declaring war on Apple, the world’s biggest tech company — and barely a month into his tenure at the helm of Twitter — would end in disaster. To be fair, Musk wasn’t the first CEO to baulk at Apple’s weighty fee structure, which took a 30 percent tithe on any in-app purchases made by customers; nor was he the first entrepreneur to have been under the illusion that he’d be able to work around this seemingly usurious fee by sending subscribers through a custom system of his own design. 

But when it had been made clear to him, in a meeting two days before in this very room — the long table sparsely attended by what remained of Twitter’s upper-level marketing and sales department — just how binding Apple’s payment structure was, Musk’s face had blanched, and his eyes had begun to blaze. Clearly, he didn’t see Apple’s fees as a simple, heavy-handed, profit-driven business strategy; to Musk, Apple’s behaviour was a direct affront to his belief system of innovation, freedom, and competition. 

At first, Crawford had done her best to just listen to Musk’s concerns, acting as a sounding board. Maybe, despite his dismay at Apple’s policies, the rational portion of his brain would take over and he’d concluded that it was simply a noxious pill Twitter would have to continue to swallow. But very quickly, it had become clear that Musk wasn’t interested in accepting the status quo. 

By their third conversation on the subject, he’d told her that he intended to fight Apple, make it a legal battle, bring it all the way to the Supreme Court if necessary. Sensing that he was beginning to spiral, Crawford had offered a potential solution; what they really wanted to do was divert Twitter’s paying customers to the web, and away from Apple’s platform — but Musk had immediately shut that idea down. 

The web, he had exclaimed, was an insecure place for payments; pushing paying subscribers toward the web would open Twitter up to bot attacks, a fear so antiquated that it had caught Crawford by surprise. She’d tried, gently, to explain the safety of modern web payments. 

Crawford herself had been on the team that had integrated Stripe as Twitter’s payment provider — to which Musk had icily replied, “I know more about payments than any of you.” To better make the point, he’d demanded that Twitter immediately turn off all web subscription. Meaning, from that moment on, the only way anyone could make a payment to Twitter was via the app — primarily, via Apple. 

To Crawford, this had been a bad business decision, stemming from paranoia. But she’d also realised that she herself had mis-stepped; rather than attempting to steer Musk away from that ephemeral edge, she’d confronted him — which had only sent him hurtling further forward. 

There was a right way to handle Musk, and more important, a decidedly wrong way to handle him. And it wasn’t simply experience that had taught Crawford this maxim; the day after she’d first met the billionaire, she’d been taken aside by a member of his entourage — the impressive young COO of his Boring Company, Jehn Balajadia, who in recent weeks had become Musk’s main operational liaison. 

“You should know some things,” Balajadia had told her, after sitting her down in a quiet corner of the headquarters. “Elon is a very special guy, and as someone who is going to be close to him, your job is to help take care of him, protect him, to make things go well for him. The world is going to want to get in through you, and you need to be really careful from now on…” 

Over weeks, Crawford had experimented with different ways to communicate with the billionaire and had found that what worked best was a combination of humour and appeal to ego. What Musk seemed to love the most were memes, emailed to him at night (never in the morning), the edgier the better; what he feared most was anything that might damage his public reputation. 

For years, he had been known to most of the world as a genius, one of the greatest entrepreneurs in history. Since his takeover of Twitter, though, the conversation surrounding him had shifted in a decidedly negative direction, and he was extremely sensitive as to how people viewed him. 

Over the past few days, as Musk had become more entrenched in seeing Twitter’s battle with Apple in ideological terms, Crawford had attempted to use humour to placate the billionaire — sending him meme after meme poking fun at Apple, their fee structure, whatever she could think of that might defuse his growing vitriol. 

But just glancing at his Twitter account from the past 24 hours, she could see that her strategy was failing. Calling Apple politically “biased” in a tweet to his 100 million-plus followers, Musk had further expounded that “Apple has mostly stopped advertising on Twitter. Do they hate free speech in America?” 

He’d accused Apple of threatening to “withhold Twitter from its App Store”. Worse yet, at 7am that very morning, he’d tweeted an image of a highway dominated by an exit sign offering two choices: “Pay 30%” accompanied by an arrow pointing straight ahead, and a left turn signal aiming toward “Go To War”. 

Though he’d since deleted the “Go To War” tweet, it was clear the idea had lodged itself in his mind. Rocking slightly in the minuscule chair next to Crawford, he was almost rambling now, deep in a monologue about Apple’s authoritarian behaviour. How their in-app fees were a form of robbery, proof of their monopoly over the tech sector; how they needed to be broken up, fought legally. 

Then he began to go further, testing what she perceived to be another potential tweetstorm, setting off alarm bells within Crawford that had her sitting straight up in her chair. He began talking about rallying his followers to go after Apple, not just online, but IRL, some sort of loosely defined protest at Apple’s headquarters. 

She could hardly believe she was hearing him right — he was essentially talking about sending people with pitchforks to Cupertino. Now she knew she had to act quickly. This path would not only have serious repercussions for Twitter’s future, but also wider implications that might destabilise the entire tech sector.

A war between Twitter and Apple wasn’t an act of genius; it would be more akin to madness and would surely tarnish the reputations of both companies. She put her hands down on the table and rose out of her seat, all 1.49m of her, now eye to eye with the mantis-like entrepreneur. 

Then she laid it out in a way that Musk would understand. Twitter 1.0, as Musk had been calling the past regime, had left skeletons in Twitter’s closets that made a war with Apple unwinnable. So, through no fault of his own, Apple had the billionaire by the balls. 

Specifically, Twitter 1.0 had done a very poor job of monitoring adult content on the platform. In fact, pornography was a much bigger driver of engagement than anyone in former management would have cared to admit. It was a “don’t ask, don’t tell” side of the business. 

Even worse, it was no secret that over the years, there had been an even darker, and continuous infiltration of the platform: child porn, which had proliferated despite the best efforts of Twitter’s security and moderation teams to snuff it out. Not only did Apple know about Twitter’s adult content and its troubles with child porn; since the Twitter app ran primarily through them, they must have the receipts. 

If Musk went to war with Apple, they might use these receipts against him. Apple could remove Twitter from their platform, as Musk had tweeted — but not for violating a payment issue. They could go after Musk with real dirt, adult content and child porn, sullying him in a way that would resonate on the world stage. 

For the first time since he’d sat down at the conference table, Musk went silent as she finished speaking, staring at her as she stood next to him. Then he finally shook his head. “That was before I was in charge. None of that was my fault.” 

“But you’re in charge now,” Crawford responded. She realised she was trembling. Another beat passed, and then, thankfully, he nodded. He was obviously contemplating how it would look to the outside world, if Apple began to lob accusations involving child porn at Twitter, while he was CEO. 

He knew what that would mean: another hit to his reputation, which was already being dragged through the mud daily by the mainstream media. 

Crawford felt relief move through her. She lowered herself back into her seat, as Musk began dialling back the vitriol, suggesting that instead of sending lawyers — or a pitchfork-waving mob — it would make more sense for Musk himself to head to Cupertino. Talk it out, find a middle ground, a peaceful way forward. 

As Crawford listened to him talk, she noticed she was still trembling. She knew how easily things could have gone differently. What a tightrope she had walked, getting through to Musk before the idea of war became imbedded. Because once it became imbedded, once it became about winning and losing: Musk didn’t lose. But he did have the capacity to change course, if someone got to him in time. 

Lately, it was becoming more and more difficult to know when that moment had passed. Worse, Musk’s paranoia seemed to be growing — and not just about bots attacking payment platforms. He now seemed to barely trust anyone outside of his inner circle. 

His fears weren’t entirely unwarranted; just a few days ago, Crawford had been secretly contacted by a handful of the second-level managers who were still employed by the company, informing her that they were planning a “mass quitting event”, asking if she’d add to their number. She had turned them down, but not turned them in. 

She still believed she could do more good having Musk’s ear than by walking out the door. But every day, she felt her ability to redirect him away from those edges and cliffs was deteriorating; sooner or later, it seemed likely, his paranoia, his genius, maybe even his madness would get the better of him. Once that happened, no number of memes, threats of lost approbation, or frosted glass would keep him from plummeting down the other side — and taking Twitter, or what remained of it, along with him.

Breaking Twitter is published by Pan Macmillan.