• by Steven Rosenbaum , Featured Contributor, March 24, 2025

Holy crap, folks. I just finished listening to 14 hours of Sarah Wynn-Williams' explosive tell-all "Careless People," and let me tell you -- her story is SEARING. Like, jaw-on-the-floor wild. Let's dive into this dumpster fire, shall we?

When Obama Burst Zuck's Bubble

Picture this: It's late 2016, Trump just shocked the world, and Zuckerberg is doing his global big-shot tour when he crosses paths with Obama at some fancy university in Peru. Obama apparently reads him the riot act about Facebook's role in spreading misinformation.

And how does our boy wonder CEO react? Like a teenager who just got grounded! He's "silently fuming," ranting to his team that Obama "got it totally wrong" and that fake news was barely a blip on Facebook.

Zuck says of Obama: "He kept going on about fake news and misinformation teams. He doesn't get it. He got it totally wrong, totally out of proportion. He said that Facebook is playing a destructive role globally, and I think he actually believes that."

Here's the kicker: Wynn-Williams says Zuckerberg couldn't handle being criticized by someone more powerful than himself, because, well, there's almost nobody who fits that description in his world! She writes that he was "completely unused to FRANK criticism from anyone more powerful than him."

And then something clicked in Zuckerberg’s brain. After rubbing shoulders with presidents and prime ministers who "dote over him like some boy king," Wynn-Williams writes that Zuckerberg had this revelation: "If Trump can do it, so could he." I mean, why not? "Not only does Mark now have Trump's playbook. He owns the tools and set the rules."

She recounts how he began planning classic campaign activities: "He wants to meet with Black leaders, opioid addicts, auto workers. He wants fried food in Iowa, barbecue in Texas. He wants to go to a rodeo drive…[and] wear a hardhat."

The Creepy AF Teen Targeting Machine

But wait, it gets worse. WAY worse.

Wynn-Williams drops a bombshell about how Facebook was actively targeting teens during moments of emotional vulnerability.

She details how a confidential document leaked revealing that Facebook was offering advertisers the opportunity to target teens "during moments of psychological vulnerability, when they feel worthless, insecure, stressed, defeated, anxious, stupid, useless, and like a failure."

Let that sink in. Facebook was tracking when KIDS felt like garbage so it could sell them stuff!

She explains that "Facebook monitor teenagers' posts, photos, interactions, conversations with friends, visual communications, and Internet activity on and off Facebook's platforms and uses this data to target young people when they’re vulnerable."

Facebook used this technique with teenaged girls: "Facebook does work for a beauty product company, tracking when 13- to 17-year-old girls delete selfies, so [it] can serve a beauty ad to them at that moment."

Wynn-Williams reflects on the horror of this: "We don't know what happens to young teen girls when they're targeted with beauty advertisements after deleting a selfie. Nothing good."

And when this horrific practice leaked to the press, what did Facebook do? Fix it? Apologize? NOPE! According to Wynn-Williams, they straight-up LIED, releasing a statement claiming: "Facebook does not offer tools to target people based on their emotional state."

When Wynn-Williams suggested Facebook should simply stop targeting vulnerable teens, an exec basically laughed in her face, responding that if both sides were unhappy, they "must have gotten this exactly right." One ad exec even called her late at night to complain about the denial, saying: "This is the business, Sarah. We're proud of this. We shout this from the rooftops. This is what puts money in all our pockets."

She details how senior executives at Facebook knew this was happening, noting that someone “asked whether it is possible to target on words like 'depressed,’ and the deputy chief privacy officer confirms that yes, Facebook could customize that for advertisers."

The cynicism is staggering. While the company publicly denied targeting teens based on emotional vulnerability, just three days later on an earnings call, Wynn-Williams reports that Sheryl Sandberg was "touting Facebook's ability to target based on sex and age."

The Human Cost

What makes Wynn-Williams' account so powerful is her transformation throughout the book. She started at Facebook believing it "was going to change the world" and was "the greatest political tool of my lifetime." By the end, she describes getting fired as a "quick euthanasia" after feeling "so beaten down by my tenure at the company."

Her firsthand account of sexual harassment by Joel Kaplan, Facebook's vice president of global policy, is equally disturbing. She describes him grinding up against her on the dance floor at a work event, announcing that she looks “sultry,” and making “weird comments" about her husband. Even when she nearly died from childbirth complications, he kept pressing her about where exactly she was bleeding from. An internal investigation cleared him of any wrongdoing.

"Careless People" Indeed

The book's title comes from "The Great Gatsby,” referring to people who "smashed up things and creatures" and "let other people clean up the mess they had made." Couldn't be more perfect for these tech bros playing God with our society.

I listened to the audiobook narrated by Wynn-Williams herself, and it's powerful stuff. You can hear her transformation from wide-eyed idealist to a woman who's been sexually harassed by her boss, ignored by management, and able to see the real pain the company is causing. Her personal delivery adds a raw authenticity that a professional narrator couldn't capture.

As Facebook -- now Meta -- fights to remain relevant and Zuckerberg removes any fact-checking and all DEI initiatives at the company, this book couldn't have come at a worse time for the tech giant. Advertisers are starting to ask questions about how their brand dollars are being used to fuel pain and a rapidly declining teen mental wellness epidemic. It feels like change is in the air.

The fact that Facebook fired her and then tried to sue to keep this book from reaching the public has only backfired spectacularly. It's currently sitting at #1 on the New York Times bestseller list. Nothing like trying to silence someone to ensure everyone hears what they have to say.

You can listen to chapter 44, “Emotional Targeting and Teens” here.