There’s a particular subgenre of tech industry book that piques my interest. Chaos Monkeys, Uncanny Valley, Extremely Hardcore—they purport to reveal the dirty underbelly of Silicon Valley, a true on-the-ground retelling of major events and points in history that gets behind the puff pieces shown by the press. It’s a genre that looks to demystify famous founders and powerful executives, made possible by the youthfulness and accessibility of many of this tech elite cohort1.
Careless People is the latest in this literary lineage. Written by Sarah Wynn-Williams, Facebook’s Director of Public Policy from 2011 to 2017, it’s a behind-the-scenes look at Facebook’s rise to a geopolitical force, penned by someone who drove much of the initial effort to position the company in the political sphere. The memoir made it to the NYT bestsellers list, was reviewed well by critics, and was widely recommended by journalists and tech observers.
Well, at least I enjoyed it more than the aforementioned genre predecessors2.
To be fair to Wynn-Williams, the book is characterized as a memoir, and she establishes her background and narrative in the early chapters en route to interviewing and eventually working at Facebook. At the same time, this book’s launch prompted legal action from Meta, which is telling in how damaging its claims are to its current executives, particularly Mark Zuckerberg and Sheryl Sandberg, their CEO and COO at the time, respectively.
The revelations are indeed wild, shocking in the amount Facebook knew of its impact on countries and governments, and damning in their leaders’ nonchalance and metaphorical shoulder-shrugging response. The book reads chronologically, so while the Cambridge Analytica scandal and its impact on the 2016 US presidential elections come in later chapters, they were also well-covered by news outlets at the time. Some of the chapters in the middle—after the author spent years trying to engage Facebook executives in geopolitics—reveal how deeply the company entangled itself in governments and political movements around the world. Two examples stand out: its role in enabling genocide in Myanmar, and the extent to which the company kowtowed to Chinese authorities in an extended bid to enter the country.
In between the world-changing, globe-trotting initiatives are the more personal caricatures of some of Meta’s senior leadership. The incidents that the author describes hardly put Mark and Sheryl in a flattering light, but of course that’s the point: although the descriptions of Mark’s awkwardness were about what people expected, Sheryl’s invitation to her subordinates to join her in bed on her private jet made headlines and drove plenty of free publicity. At the same time, most executives come across as aloof and detached in recognizing the impact of Facebook on political systems. In this retelling of world events, their inaction is perhaps less attention-grabbing, yet more incriminating.
So that’s what the people came for and propelled the book to bestseller lists, but there’s also the tricky business of interleaving a memoir amidst all the corporate scandal. Some reviews frame these interludes as “dark humor,” but I found some of the personal anecdotes to be, at best, awkward autobiographical asides, and at worst, distracting indulgences. One passage has the author going on for pages about how she agreed to go on an overseas work trip soon after having a baby, and made the forgivable mistake of bringing an electric breast pump on a plane and to a country with no power outlets. I guess it’s meant to be funny and humanizing, but it reads like a standup comedy bit that gets edited into a 2-minute joke in the Netflix special.
Throughout the book, the author sets up these scenarios that are meant to create narrative tension, but are so fleeting and inconsequential that it reminds me of the anime trope of stretching a 15-second confrontation into multiple episodes as filler. There will be paragraphs where, in a moment of conversation, she will fear for her job based on a bunch of fleeting details from prior interactions with her boss and others. The prose builds up to this possible pivot in her career, only to immediately de-escalate when her boss says something nice and her anxieties are mollified. I can certainly relate to an inner monologue or two gone amok and generating a cascade of emotions, but running play-by-play commentary with repeated ho-hum outcomes is just poor storytelling.
The desire to inject personality and autobiographical details is understandable. The thing is, Careless People wears the title well with much of its content, and the author was uniquely positioned in a high-ranking role within Facebook3 to focus on that exposé. It feels like a squandered opportunity to doubly focus on that inside story of the influence and control wielded by Facebook’s executives on the world stage, and how little they seemed to care about using that power responsibly. Instead, I found her extensive inclusion distracting from her central thesis. After all, I’m just here for the juicy scandals.
The older CEO-founder guard—Bezos, Gates, Larry & Sergei—are too far removed for the same type of exposé.↩
I actually “read” it via the Entertrained app, which meant I typed it out one chapter at a time.↩
This is worlds more credible than something like Chaos Monkeys, in which the author’s sole interaction with the CEO was a brief rebuke during a presentation.↩
