In the room with Elon

Having put @Markzuckerberg under the microscope in a bestselling book that became Hollywood film The Social Network, @Benmezrich unravels @Elonmusk’s turbulent first year at Twitter through the eyes of those closest to the action

I’ve been an avid Twitter user since November 2008. I’ve watched the site grow from a scrappy start-up to one of the most important social media sites. When the news of Elon Musk’s interest first broke – on Twitter, of course – I was intrigued. Elon is one of the most complex characters I’ve encountered. Even so, I never could have predicted the wild, and sometimes absurd, dramatic turns that ensued. My account of this turbulent first year is based on dozens of interviews, multiple first-person sources, and thousands of pages of documents.

29 November 2022

Ten minutes past midnight on a crisp San Francisco evening, Esther Crawford found herself in a dimly lit conference room, 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 at a ridiculously long table. Beyond stood a wall of glass that had once looked out on to the bustle of the rest of the floor. After choosing the space as one of his preferred roosts, one of the first things Elon had done was to frost the glass — unintentionally transforming it into a dark, cavelike bunker.

Esther was tired. She hadn’t slept more than a few hours; she had just been contemplating heading home to her husband and three kids when Elon wandered in.

Her life had taken some dramatic turns in the past four weeks as she became one of the few people left at Twitter with a direct line to the self-described ‘Chief Twit’. That put her in the privileged, and often terrifying, position of steering Elon away from the edges of cliffs.

Tonight, it seemed, was going to be another one of those moments… The cliff that Elon was heading toward, at breakneck speed, was publicly declaring war on Apple.

Elon wasn’t the first CEO to baulk at Apple’s weighty fee structure, which took a 30 per cent tithe on in-app purchases made by customers. But he’d told Esther that he intended to fight Apple, make it a legal battle, bring it all the way to the Supreme Court if necessary. Esther had offered a potential solution: to divert Twitter’s paying customers to the web, away from Apple’s platform – but Elon exclaimed the web was insecure; it would open Twitter up to bot attacks, a fear so antiquated that it had caught Esther by surprise. She’d tried, gently, to explain the safety of modern web payments, to which Elon had icily replied, ‘I know more about payments than any of you.’

There was a right way to handle Elon. She

had experimented and what worked best was a combination of humour and appeal to ego. He seemed to love memes, emailed at night, the edgier the better.

Esther had been sending him meme after meme poking fun at Apple. But her strategy was failing. And now, he was almost rambling about Apple’s authoritarian behaviour. Then 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 knew she had to act quickly. Rising out of her seat, all 4ft 11in of her, she laid it out in a way he’d understand: Twitter 1.0, as Elon called the past regime, had left skeletons in Twitter’s closets that made a war with Apple unwinnable. Specifically, Twitter 1.0 had done a 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. Even worse, 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. If Elon went to war with Apple, they might use this against him.

For the first time since he’d sat down, Elon was silent. Then he finally he nodded and Esther felt relief. But she also knew things could have gone differently… Elon’s paranoia seemed to be growing.

When Esther had first heard that Elon was taking Twitter private – a deal that was finalised in October 2022 – she anticipated the layoffs that followed; Elon’s public displeasure with Twitter’s former leadership team had hinted at much more than an employee haircut.

Frightening as that seemed – for someone with three kids and a mortgage – Esther also found it strangely exciting, especially if Elon was going to sweep away the bureaucratic layers that he believed were stifling Twitter’s innovative spirit.

Her route to Twitter hadn’t been easy. She’d been brought up in a strict religious cult in rural Oklahoma; her only solace had been computers and the internet. After escaping to Oregon State University, she eventually moved to San Francisco to work for various social media-adjacent companies such as Circle and Lyft, and later co-founded a company, Squad, a generative AI endeavour before generative AI was hot.

Later she pivoted Squad into a screensharing social app, inspired by her seven-yearold daughter’s eagerness to find some way to chat with her friends while she played Roblox, was later acquired by Twitter. Since then, she’d been part of various teams, including one that had created Spaces, Twitter’s live audio feature. But she’d also found herself bogged down by the bureaucratic hierarchies – until Elon turned up.

One day she was in the Perch, the lively coffee shop at Twitter headquarters, when a hush descended. There he was, Elon Musk: bigger in person than he seemed on TV, hunched forward, dressed in black; trailing an entourage of 20 to 30, some jogging to keep up.

Nobody was approaching him – and moments later she found herself moving across the coffee shop, introducing herself. When she told him that she led new products, including creator monetisation and payments,

Elon lit up. ‘We should talk,’ he said. ‘Email me.’

The next morning she was summoned, for the first time, to the C-suite, filled with various lawyers and businesspeople, and among them, X AE A-12, Elon’s two-year-old son with the pop singer Grimes.

The room was dominated by a giant table. Elon was sitting alone – no laptop, just his phone. He gestured to the chair next to him, pushing it out with his foot.

He seemed extremely approachable. His sense of humour came out immediately. She began walking Elon through some of the products she had been developing but realised quickly that he didn’t have the patience for details. So she adapted, focusing on broad concepts; he seemed pleased – he told her she really ‘got it’.

Days later, at 9.30am on a Saturday morning, Esther’s phone rang. It was one of Elon’s ‘Goons’.

‘What are you doing right now?’ he said. ‘Eating cereal,’ Esther responded. ‘Elon wants to see how soon you can be here.’ She’d arrived at headquarters 30 minutes later, and found Elon with two engineers and various members of his inner circle. Elon welcomed her with a nod. He was mid-conversation, expounding on how terrible Twitter’s financial situation was: his intention was that 50 per cent of Twitter’s revenue would in the future come from subscribers.

There was already a subscription option, a product called Twitter Blue, which had launched in 2021. It hadn’t gained much traction – it offered a handful of features, including the ability to ‘undo’ tweets for up to 30 seconds. Elon intended to up the ante. There was one valuable commodity that Twitter had at its disposal: the famed ‘Blue Check’, doled out to verified celebrities, journalists, politicians and notable figures. It increased visibility on the site and marked them as ‘more reliable’.

Elon intended to restructure the system, melding it with Twitter Blue, so people had to pay for a blue check, whoever they were. Esther didn’t immediately hate the idea; but it was obvious, at least to her, that paying for Blue Checks was not the same thing as paying for verification. To verify people – effectively – would require a third-party vendor with the ability to make sure people were who they said they were.

Nobody was going to risk pushing back. But Esther did, telling Elon that the Blue Check needed to come with real verification. He did not seem upset; he half-smiled then launched into a 30-minute monologue about advertising. Then he turned directly to Esther as he finished speaking: he wanted her to lead this project – and he wanted to do a kickoff with the team that would develop the new Twitter Blue in one hour.

One hour? There literally was no team. But this wasn’t the moment to challenge him.

An hour later, a virtual conference call was in full swing. Esther’s heart was beating fast as she sat by Elon; she and the two engineers had pulled together a killer team: 20 engineers, as well as people from marketing, sales and design. She’d caught one engineer on his way to the airport. And a designer in an Uber on the way home.

‘This is an Elon Project.’ Those magic words got people to drop everything.

From then on, Esther was given free rein of the second-floor conference space, her own, independent war room.

A now infamous picture was taken at 3:34am on a Wednesday of her sleeping in the office. She’d been going for four straight days; she hadn’t left the office, not even for a meal. Yet when Esther retweeted it, she hadn’t counted on the vitriol.

Though she would be the first to admit, the

There was a right way to handle Elon. He seemed to love memes, the edgier the better

timing was – well, unfortunate. Outside, Twitter was lurching through a sea of bad media – advertisers leaving, mass firings.

Esther was disturbed by the way they happened. The impersonal email, the sudden cutting off of access, the seemingly harsh way in which long-time employees were being treated. But meanwhile she had leapfrogged up the chain of command, and was now one of the few people working with Elon face-to-face.

At the end of a particularly intense meeting where she laid out her evidence that allowing anyone to buy Blue Checks, and pretend that meant they were verified, would end in a bad, potentially dangerous product, Elon had come frighteningly close to blowing up at her. ‘There’s only one product manager at this company,’ he said, ‘and IT’S ME.’

But the day before the launch, Esther hit Elon with her concerns one last time. ‘Sounds like Esther is talking out of fear,’ he said this time. ‘I don’t make decisions out of fear.’ He was mocking her openly.

Then the new Twitter Blue went live.

Maybe two, three hours in; it was obvious that the project was a disaster. Esther’s concerns had come true, in almost Hollywood fashion. Not only had people happily paid $8 to impersonate celebrities and major companies – they’d gotten creative. Some of the impersonations were clearly comedy: a ‘Nintendo’ corporate account tweeting a picture of Mario giving the middle finger; a tweet from ‘Cocacola’, ‘If this gets 1,000 retweets we will put cocaine back in Coca-cola.’

To Esther’s surprise, Elon was laughing, sometimes uproariously as he scrolled from tweet to tweet. When he got to the Nintendo account, he nearly fell out of his chair. At some point he had received enough frantic calls that he gave the order to shut down the revamped Twitter Blue. Yet even as he flicked the off switch, Elon did so with a smile.

One month later, Esther launched a revamped, resurrected Twitter Blue to little fanfare. This time around Elon had allowed her team to include a modicum of review to each customer first. He’d also promised that Twitter 2.0 would be more fun, though from what Esther was seeing he seemed increasingly morose, there was almost always an edge to the jokes, an undercurrent of what seemed like real anger.

One evening in December, Esther found herself staring at her laptop. The title of the email she had drafted to Elon was: ‘Twitter is in a death spiral.’ Her husband read it, concerned. ‘You sure about this?’

She shrugged. Maybe he was right – but she believed Twitter was on the verge of collapse. In her estimation, the company had around six weeks of runway before the spiral would be irreversible. Internally it was common knowledge that in three areas – Revenue, User Engagement, and Employee Morale – Twitter was beyond the brink.

Esther knew that the prudent thing would have been to keep her head down – but Elon had enough people around him whose only mandate seemed to be to prop up whatever strategy or whim he brought forward. In her mind, what Elon needed, more than a thousand sycophants, was a single voice willing to say ‘no’. So she hit send.

The conversation that followed took place behind the wall of frosted glass. For the first half hour, she argued her point and each time he tried to wave off her critiques as ‘sky-isfalling’ exaggerations.

Yes, Elon had a tendency to lash out. During product development on Twitter Blue, engineers were called idiots to their faces, people got fired in the middle of an argument. But she barrelled forward. There was zero internal communication, she told him; just fear, backstabbing – 80 per cent of the people at Twitter were interviewing elsewhere.

After a brief pause, he seemed to hear her. He told her that he would think about what he could do better. She left feeling optimistic.

Passing the bodyguards, she threw a last glance back. Elon was hunched forward, almost despondent. She thought back to a conversation they’d had weeks earlier about family. Elon had told her that his older kids didn’t like to hang out with him. She’d felt bad for him at the time, and she felt bad for him now.

25 February 2023

On the drive out of San Francisco to Great Wolf Lodge, a Huckleberry Finn-inspired water park, Esther had promised herself and her husband that she was going to leave work behind for the weekend. But her thoughts kept returning to it.

For a while after their conversation, Elon had made great efforts at rebuilding connections to the advertising community. But by February, he’d gone back on the warpath. A rapid firing of engineers over petty disagreements on Twitter was concerning enough, but Esther had also witnessed Elon’s paranoia ratcheting up. He believed that many of Twitter’s employees were conspiring against him.

The previous Monday morning, she’d gone up to the tenth floor and seen a pair of giant whiteboards with every important remaining employee’s name written on them, listing them from the most expensive to the least. Several people were having hushed conversations. Esther tried to put it out of her mind, and she’d been all smiles as she’d packed up the car, making sure the kids had their bathing suits. It was only halfway into the trip that she’d turned to her husband, ‘You know, there’s a 50 per cent chance I won’t have a job when we return.’

They’d both laughed; now, a day later, she couldn’t stop herself from reaching for her laptop. For a moment everything seemed normal – and then, suddenly, the screen went black. Nothing.

She’d been locked out of her email, out of Slack, out of Twitter.

At first she felt confusion. She’d heard of colleagues who had gone through similar moments, only to find it was a technical glitch. But no – she knew. Elon had fired her.

Maybe it had been the email and the conversation about Twitter’s death spiralling. Maybe it was just another effort to whittle down Twitter’s bottom line. With Elon, it probably wasn’t personal, even though with Elon, it always seemed so personal.

She knew that some ex-colleagues would have a field day at her expense; she had, after all, risen while so many had fallen. But she had no regrets. She’d tried to make a difference.

Even now, she didn’t hate him. She would walk away proud of her accomplishments. She had her memories – and her family.

Closing her laptop, she leaned back and pictured him. She didn’t think of him as a billionaire, or a demanding, whimsical, sometimes tyrannical boss, or even as a genius. She thought of Elon as she’d last seen him, as she’d so often seen him. Alone in that big glass conference room, at that long empty table.

Maybe the saddest, loneliest man she’d ever met.

Abridged extract from Breaking Twitter: Elon Musk and the Most Controversial Corporate Takeover in History, out on 9 November (Pan Macmillan, £22); order at books.telegraph.co.uk

Elon’s paranoia was ratcheting up. He believed many employees were conspiring against him

Esther Crawford, who became a close advisor to Musk

Musk tweeted his arrival at HQ: ‘Let that sink in!’