Internet Book Club: Careless People

Incuriosity, carelessness, and the current political moment

Previously in Internet Book Club:

• Extremely Online by Taylor Lorenz

• Filterworld by Kyle Chayka

• So You’ve Been Publicly Shamed by Jon Ronson

• The Anxious Generation by Jonathan Haidt

• The Modem World by Kevin Driscoll

---

Mark Zuckerberg doesn’t want you to read this book.

Sarah Wynn-Williams, the author of tell-all memoir Careless People, is the highest ranked executive to ever blow the whistle at Meta. The book’s title comes from a quote from The Great Gatsby about its two main characters:

They were careless people, Tom and Daisy- they smashed up things and creatures and then retreated back into their money or their vast carelessness or whatever it was that kept them together, and let other people clean up the mess they had made.

Mark Zuckerberg and Sheryl Sandberg serve as the modern day Tom and Daisy in Wynn-Williams’ retelling, almost unbelievably nonchalant about the scale of their power and flippant with their usage of it. The book is filled with deeply embarrassing stories for Meta’s top leadership - so much so that they’ve sued to silence her. Meta, which calls the book ‘false and defamatory’, claims that Wynn-Williams has violated a non-disclosure agreement she signed with the company, and an arbitrator granted their request for an emergency gag order. Wynn-Williams cannot talk about the book, give interviews, or really say or do anything at all in promotion of the book.¹

This, of course, led to an incredible Streisand effect boosting the book’s popularity - it debuted at #1 on the NYT Bestseller list. And since the author can’t give interviews, I figured I should contribute to the Streisand by reviewing it here.

An Embarrassment of Riches, Rich with Embarrassments

My first thought reading the book: Holy shit did this woman ever violate her NDA.

I haven’t gone deep into each side’s legal claims. But if there was an NDA that Wynn-Williams signed, she absolutely disregarded it by publishing this book. Maybe she’s got some kind of argument that the NDA shouldn’t apply, was illegal, or something like that. But this book is filled with insider secrets and stories from the days of Facebook’s rise, and almost none of them make Facebook or its top executives look good. Wynn-Williams didn’t so much violate the NDA as blow it to smithereens.

But man, it might have been worth it to get all the stories we got. Here are just some of the stories from Careless People:

• Sheryl Sandberg routinely forces her young female assistants to nap/sleep in the same bed as her on private flights. There’s no outright accusation that she has sex with them, but either way it’s utterly bizarre behavior, and something that was supposedly common knowledge to anyone who traveled with Sandberg.

• Sandberg lied that she had been booked on a flight that ultimately crashed before changing it last minute - for the purposes of getting attention during a book tour.

• Mark Zuckerberg, who was obsessed with getting into China, repeatedly tried sucking up to Xi Jinping - so much so that he asked Xi to do him the honor of naming his child. Xi refused. Zuckerberg would also plan ‘spontaneous’ moments where he could ‘run into’ Xi backstage at diplomatic events and grew depressed when Xi’s handlers wouldn’t let him get close.

• Zuckerberg didn’t have the same respect for other world leaders. He routinely showed up late to meetings with heads of state because he won’t get up before noon. Not even after flying to their country for the purpose of meeting them. ‘No Mark meetings before noon, not even for prime ministers’ was apparently a well known rule at Facebook.

• Zuckerberg’s posse of corporate friends loses to him on purpose whenever they play Settlers of Catan and other board games. Wynn-Williams describes the sand-bagging as incredibly obvious, but Zuck never notices it happening, despite how blatant it is.

• It’s hard to overstate how badly Facebook wanted into China. They were prepared to not only hand over complete access for all Chinese user data to the CCP, but also to allow the CCP access to some Western user data and to censor Western accounts. One memo cautioned that “Facebook employees will be responsible for user data responses that could lead to death, torture and incarceration”, after which they continued without change in policy.

• Zuckerberg decided to run for President after the 2016 election because Barack Obama yelled at him in a private meeting.

• The company was cavalier with its own employees in other countries. It sent Wynn-Williams to Myanmar - at the time a brutal dictatorship - without working technology or connections and told her ‘not to come back until the problem is fixed’. Mark Zuckerberg’s initial reaction to a Brazilian executive being jailed was complete nonchalance, and only after hours of his employees telling him that it was a big deal did he suggest putting out a statement that it was ‘heartwarming’.²

• The company built systems targeting “thirteen-to-seventeen-year-olds… during moments of psychological vulnerability when they feel ‘worthless,’ ‘insecure,’ ‘stressed,’ ‘defeated,’ ‘anxious,’ ‘stupid, ‘useless,’ and ‘like a failure,’”. They also built systems to detect when teenage girls would delete a selfie, so that they could serve them beauty ads directly afterwards.

• Internally, the company was well aware that Facebook was driving ethnic hatred in Myanmar but did nothing until the story became an international scandal.

• Wynn-Williams was repeatedly sexually harassed by Joel Kaplan, one of the most powerful men at Facebook and Meta’s current President of Global Affairs. She was fired for reporting it.

This is just a taste - there are many more horrifying and hilarious stories in the book. And Careless People is fascinating precisely because it walks that line. I was surprised by how darkly comedic it was. I burst out laughing at several occasions, real physical guffaws at some clueless thing Zuckerberg had done. But underneath the humor, you’re constantly asking yourself “This is what the most powerful people in the world behave like?”

Incurious Carelessness

What really stands out to me after reading Careless People is how well the book’s title fits. Most of the Facebook executives documented aren’t evil or nefarious. They’re just careless. They’re ignorant of the world outside Facebook, careless with the vast amounts of power they suddenly had, and resentful whenever they’re expected to care about anything other than growing Facebook’s user count.

Zuckerberg in particular comes off like a kind of idiot savant child king. There’s no denying that he’s in some ways brilliant, but in the book’s telling he bounces from geopolitical crisis to geopolitical crisis, only ever vaguely aware of why people are mad or what he’s supposed to be doing. At one point Wynn-Williams is taking government officials from New Zealand on a tour of the Facebook offices, sees Mark approaching their group, and calls out “Mark, would you like to meet the prime minster of New Zealand?” to which he responds “No, I already said I definitely didn’t want to do that”. He’s then forced to backtrack because he apparently didn’t realize that the man standing next to Wynn-Williams, five feet from him, is the prime minister of New Zealand.

Careless People is filled with anecdotes like that, stories about Facebook’s leadership being utterly clueless in the face of governments, regulators, and the rest of the world. Their disregard for politics and for the real-world consequences of Facebook’s policies are a point of pride, not a point of shame. It almost reads like a corporate version of The White Lotus, filled with fascinating and fatally flawed people who are completely unable to see past their blinders. And Wynn-Williams shouldn’t be spared from this. As the author, she paints herself in the best possible light but she’s still an active participant in nearly every story. At every turn she’s enabling the careless people who are breaking things right and left. She might have given some half-hearted objections, but was a high level executive and still carried Facebook’s corporate will.

What I ultimately take from the book is that, as the Atlantic says, the careless people won. The careless worldview that drove Facebook shares a lot of DNA with our current political moment. In the same way Facebook leadership genuinely didn’t care if their employees were jailed or if their social network contributed to ethnic killings, DOGE is running rampant through the federal government without really knowing or caring how they’re breaking government agencies. In the same way Facebook considered teen girls killing themselves because of social media an annoying side issue, the MAGA movement considers the economic destruction of tariffs an irrelevant distraction.

When they break something critical, both parties use the same response pattern - it didn’t happen, and if it did it was ultimately good, and why do you care, you’re just out to get us anyways. Why am I supposed to care about this stupid side issue you keep bringing up? Move-fast-and-break-things is now the governing ethos of the ruling party in America, where ‘things’ includes Social Security, our weather forecasting services, and the entire economy.

We operate in a post-truth society. Donald Trump was one of the first people to figure out that if you completely abandon the concept of shame and tell enough lies with enough gusto, lots of people will believe them. Trump himself is the avatar of incuriosity, man who does not understand the world, does not desire to do so, and resents anyone who asks him to. What both Trump and Zuckerberg share is a focus on power - Trump in the form of political power and personal loyalty from his underlings, and Zuckerberg in the form of ever-growing market share and KPI metrics.

All of this is a winning strategy. Trump’s brazen approach to things like truth and decency is superpowered by the can’t-be-bothered carelessness of companies like Facebook, where Trump’s 2016 campaign was also a pioneer and heavily utilized the social network. We now live in a world governed by careless people who can’t be bothered to understand when they break things and who view the impacts of their actions as annoying distractions.

1. The book’s publisher is not affected by the order - they can continue publishing it, selling it and promoting it.

2. The executive in question was jailed for refusing a court order to provide user data. The data in question was on a cartel group threatening to assassinate the judge.