Zuckerberg is Kendall Roy (with more than a dash of Roman). He’s the boy king who thinks he gets it, oblivious to the layers of people trying to manage his moods, If Wynn-Williams is Tom from Succession. He makes up policy on the fly — announcing at the UN that Facebook would provide Wifi for refugee camps, for example — then leaves it to others to clean up his mess.
“He seems to be giving less of a damn,” Wynn-Williams says after the Wifi policy announcement (which goes nowhere because Zuckerberg decides he wants the refugees to pay for access.) “Saying things because they sound good. Posting things because they look good … I regret having enabled this.”
If that makes Zuckerberg sound Trumpian, it’s not the only time. Like Trump, Zuckerberg says Andrew Jackson (whose Indian Removal Act led to the Trail of Tears) was the greatest president in U.S. history: “not even close.” Like Trump, Zuckerberg gets seduced by the power of crowds, asking if his team can arrange “a riot or a peace rally” when he visits Jakarta (where his suite at a top hotel is described as “more like a citadel”).
And like Trump, he’s enraged by President Obama, who takes Zuckerberg to task for fake news on the platform during the 2016 election. Zuckerberg refuses to take responsibility, seeing “fake news” as a talking point from media organizations that see Facebook as a threat. He considers buying “the failing New York Times,” but decides Facebook should make it irrelevant instead.
Zuckerberg’s main focus in the wake of that election: testing the waters for a presidential run himself. “I think he came to this dark conclusion: if Trump can do it, so can he,” says Wynn-Williams. “After all, not only does Mark now have Trump’s playbook, he owns the tools and sets the rules … after being shit on by Obama, he dug in.”
You’d expect Zuckerberg’s advisors to rein him in — but these would be the same advisors who are repeatedly found letting the boss win at his favorite board game, Settlers of Catan. When Wynn-Williams beats him at Settlers, Zuckerberg accuses her of cheating. Wynn-Williams “unwisely” unloads on his lack of strategy in general.
“You were so focused on winning the longest road just then, you weren’t paying attention to the rest of what was happening on the board,” she tells him. It’s clear she’s not just talking about the game, but Zuckerberg thinks for a while and just says: “fair.”
So Zuckerberg is in a bubble of privilege? No, says Wynn-Williams: “A bubble implies flimsy transparency,” she writes, “where you can see a normal life just beyond your grasp. What Mark inhabits is more like a thick opaque dome, a murky fortress that separates him from the rest of the world.”
What did Sheryl Sandberg allegedly do for Zuckerberg?
Zuckerberg, always an odd duck, doesn’t win the “we were all rooting for you!” award for biggest disappointment in Careless People. That goes to his former COO Sheryl Sandberg. Once seen as the adult in the room at Facebook, Sandberg became a feminist champion courtesy of the Lean In phenomenon.
Then, on a private jet from the Davos conference to SFO, a pajama-clad Sandberg repeatedly insisted that Wynn-Williams join her in the plane’s only bed. Wynn-Williams suggests another employee: a woman Sandberg calls “little doll” had slept in Sandberg’s lap in the car while Sandberg stroked her hair (and vice versa). That employee had “slept over” lots of times, Sandberg snaps: “I’m asking you.”
Apart from the inappropriateness of the ask, Wynn-Williams is heavily pregnant at the time and fears her snoring would horrify her boss. She repeatedly declines. Sandberg storms off: “people say no to Sheryl so rarely,” Wynn-Williams writes, “she doesn’t know what to do with this.” Except to tell her again on the tarmac in California as they wait for Ubers: “you should have got into bed.”
Later, confiding in another employee, Wynn-Williams is told that “half the department” has been in Sandberg’s bed, so it’s no big deal. After that, she notices Sandberg “beginning to ice me out.”
The PJs incident happens halfway through the book, but we’ve already seen a widening gap between Sandberg’s public image and private persona. She berates her team repeatedly for not seeing the difference. When they assume her kids will be OK eating McDonalds because Sandberg posted a picture on Facebook of herself doing just that, Sandberg hits back: she wasn’t actually eating that stuff.
By the end of the book, Sandberg’s staff is on another private jet, updating her on the historic Women’s March that coincided with Trump’s first inauguration. The feminist champion cuts them off to ask … what Melania Trump was wearing.
What happened to the Lean In lady? Wynn-Williams recalls this maxim from author John Updike’s autobiography: celebrity is a mask that eats into the face. “I feel a deep sadness for Sheryl,” Wynn-Williams says, “who let the mask eat into her face.”