Careless People Summary

Prologue: Careless People

Overview

The prologue opens at the 2015 Summit of the Americas in Panama, where the narrator, a Facebook policy executive, navigates a surreal state dinner filled with bizarre rituals, seminaked performers, and an unimpressed Mark Zuckerberg. The event, intended to connect Zuckerberg with world leaders, quickly unravels into a series of awkward encounters and logistical mishaps. From swapping name cards to failed attempts at diplomacy, the scene highlights the disconnect between Silicon Valley’s tech elite and the traditional world of international politics.

Surreal Settings and Strained Diplomacy

The dinner takes place in an ancient coastal ruin, flanked by guards in historical costumes and performers in flesh-toned outfits. The absurdity peaks as Zuckerberg questions the presence of seminaked actors, while the narrator scrambles to salvage his seating arrangement. A botched attempt to introduce Zuckerberg to Canadian Prime Minister Stephen Harper—who bluntly rejects the offer—underscores the tech CEO’s discomfort in this unfamiliar arena.

Chaos and Escape

As the evening collapses, the group flees through a tunnel used by costumed horse riders, dodging panicked animals and security risks. The chaotic sprint through the dark, formal attire and all, mirrors the narrator’s later reflections on Facebook’s early years: a mix of reckless ambition and unintended consequences. The night ends with the team lost in a Panamanian field, laughing at the absurdity—a fleeting moment of camaraderie amid the disarray.

Foreshadowing a Downward Spiral

The prologue closes with the narrator reflecting on her seven years at Facebook, framing the company’s trajectory as a shift from “hopeful comedy” to “darkness and regret.” She hints at Facebook’s ethical compromises, including cozying up to authoritarian regimes and inadvertently influencing elections. The anecdote serves as a microcosm of the company’s broader story: a collision of unchecked power, naivety, and global consequences.

Key Takeaways

• Tech Meets Tradition: Zuckerberg’s awkwardness at the summit symbolizes Silicon Valley’s struggle to navigate political and cultural complexities.
• Ethical Erosion: The narrator foreshadows Facebook’s moral decline, contrasting its idealistic beginnings with later compromises.
• Unintended Consequences: The chaotic escape mirrors the company’s reactive approach to global challenges, often prioritizing survival over strategy.
• Humanizing Power: The anecdote reveals the fallible, often clueless humanity behind Facebook’s towering influence.

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Careless People Summary

1. Simpleminded Hope

Overview

The chapter traces the author’s journey from youthful idealism to a pivotal career shift driven by a near-fatal shark attack, disillusionment with traditional institutions, and an awakening to Facebook’s untapped potential. It explores how personal trauma and professional setbacks reshaped their perspective, ultimately leading to a fervent belief in technology’s power to transform global politics.

A Brush with Mortality

At 13, the author survives a brutal shark attack while vacationing in New Zealand. The shark’s bite pierces their torso, nearly drowning them and causing severe internal injuries. Despite initial dismissal from doctors, their condition deteriorates overnight as sepsis sets in. A delayed emergency response leads to life-saving surgery, where doctors—without anesthesia—hack into their limbs to administer blood transfusions. The ordeal leaves physical scars and a defiant resilience. Years later, the author reflects on how this trauma fueled a determination to seize life’s opportunities and pursue meaningful work, driven by the question: “If I survived against the odds, shouldn’t I be doing something with this life?”

Cracks in the System

After studying law and joining New Zealand’s foreign service, the author works at the United Nations on environmental protections. Initial enthusiasm fades as bureaucratic inefficiencies mount—endless debates over punctuation in obscure documents, stalled progress on ocean conservation, and a sobering realization that Finding Nemo did more for marine awareness than UN treaties. A wry comment from an Argentinian diplomat (“Nemo”) crystallizes their disillusionment. The gap between idealism and reality pushes the author to seek impact elsewhere, leading to a diplomatic post in Washington, DC.

The Limits of Diplomacy

In DC, the author confronts New Zealand’s marginal role in global politics. Meetings with US officials highlight the country’s perception as a quaint vacation spot rather than a policy player. A humiliating moment during a Zimbabwe crisis meeting—where a South African counterpart mocks New Zealand’s ambition to “lead” against Mugabe—underscores this irrelevance. Meanwhile, Facebook emerges as a personal lifeline, connecting the author to family and friends abroad. Observing politicians like Chris Hipkins engage voters directly on the platform sparks a growing fascination with its untapped political potential.

Seeing the Revolution

By 2009, the author becomes obsessed with Facebook’s rise. They see it as a nascent global town square, where data collection and user engagement could redefine politics. Drawing parallels to UN debates over cross-border issues like genetically modified crops, they envision Facebook as a battleground for future governance. Yet, Facebook itself seems oblivious to its own power, framing its mission around social connection, not global influence. Determined to join the “revolution,” the author plots how to convince Facebook’s leadership of their vision—despite having no Silicon Valley ties or tech background.

Key Takeaways

• Trauma as Catalyst: The shark attack instilled a relentless drive to pursue purpose and adventure.
• Institutional Disillusionment: Bureaucratic inertia at the UN and diplomatic marginalization in DC highlighted the limits of traditional power structures.
• Tech’s Unseen Potential: Facebook’s early days revealed a disconnect between its perceived role (a social tool) and its latent power to reshape global politics.
• Conviction Over Credentials: The author’s journey underscores the audacity of betting on an unproven idea—and the urgency of shaping it before others do.

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Careless People Summary

2. Pitching the Revolution

Overview

The chapter chronicles the author’s relentless pursuit of a nonexistent role at Facebook, driven by her conviction that the platform would become a geopolitical force. Faced with Facebook’s impenetrable corporate structure, she navigates dead ends, social awkwardness, and outright rejection—only to find clarity in a personal crisis. What begins as an idealistic pitch evolves into a strategic negotiation, revealing the gap between Facebook’s public mission and its business priorities.

The Cold Approach

Facebook’s notorious inaccessibility forces the author into detective mode. She scours the internet for contact details, fixating on Marne Levine, Facebook’s newly hired VP of global public policy. After discovering a single mutual connection—Ed Luce, a former Treasury colleague—she convinces him to broker an introduction. Ed’s bemused but supportive email to Marne frames the author as a “valuable” asset, though the pitch itself remains undefined.

The Disastrous Pitch Meeting

The meeting with Marne is a masterclass in corporate skepticism. Marne dismantles the author’s vision of a “Facebook diplomat” with razor-sharp questions, exposing the disconnect between idealism and Facebook’s immediate priorities: U.S. regulatory battles, not global strategy. The author scrambles to reframe her pitch around business growth, but Marne dismisses her as irrelevant to the company’s current needs. The rejection is blunt, yet it fuels the author’s resolve to refine her approach.

Earthquake and Epiphany

A catastrophic earthquake in Christchurch becomes a turning point. Desperate for news of her sister, the author witnesses Facebook’s organic role in disaster response—communities coordinating aid, sharing safety updates, and rebuilding trust. This real-world proof of Facebook’s political utility reignites her determination. She bypasses professional decorum, cold-calling Marne with an emotionally charged pitch that finally bridges idealism and practicality.

Relentless Pursuit Pays Off

Months of ignored follow-ups and a demoralizing interview for a tangential Australian communications role test the author’s resolve. Yet her persistence—and the earthquake’s demonstration of Facebook’s societal impact—softens Marne’s resistance. In a sudden, anticlimactic call, Marne offers her the job she’d invented: Manager of Global Public Policy. The victory is tinged with ambiguity, as even Marne admits uncertainty about the role’s purpose.

Key Takeaways

• Persistence > Perfection: Repeated rejection and awkward outreach were necessary to crack Facebook’s insular culture.
• Align with Business Realities: Idealism alone failed; framing Facebook’s geopolitical role as a growth strategy resonated.
• Crisis as Catalyst: The Christchurch earthquake provided tangible evidence of Facebook’s political power, making the abstract pitch concrete.
• Invention Requires Audacity: Creating a role from scratch meant embracing ambiguity—and accepting that even the hiring manager doubted its necessity.

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Careless People Summary

3. This Is Going to Be Fun

Overview

The chapter opens with the author’s disorienting first day at Facebook’s Washington, DC, office in 2011. From the jarring mismatch between the office’s Silicon Valley-inspired “raw” aesthetic and its upscale corporate surroundings to a comedic misunderstanding over company-issued laptops, the tone is set for a culture clash. The author’s naivety about Facebook’s tech-forward workflows collides with the reality of its fast-paced, engineer-dominated environment. Amid the chaos, she grapples with her ambitious vision for shaping global policy at Facebook—a vision immediately tested when her proposal for a “global council” of experts is shut down. The chapter culminates in her first major assignment: orchestrating a high-stakes visit from New Zealand’s prime minister, a task that exposes Facebook’s internal power dynamics and the stark divide between its engineering-focused leadership and the political world she’s accustomed to.

First-Day Fumbles and Cultural Clashes

The author arrives at Facebook’s DC office expecting corporate formality but finds a chaotic, industrial-style workspace. A misunderstanding over her company laptop—she’d assumed it was for personal use, not realizing it was her primary work device—leads to a frantic dash home to retrieve it. This blunder underscores her transition from the bureaucratic, tech-averse New Zealand embassy to Facebook’s “move fast” ethos. Marne Levine, her boss, remains oblivious to the mishap, but Meredith, Marne’s assistant, signals this won’t be the last hiccup with a playful, “This is going to be fun.”

Ambitions vs. Corporate Reality

Eager to influence global policy debates, the author pitches a “global council” of international experts to advise Facebook—a common practice at organizations like the UN or Goldman Sachs. The idea is swiftly rejected, with leadership emphasizing that decisions stay in-house. This early setback hints at Facebook’s insular culture and its reluctance to cede control to outsiders. Meanwhile, her first assignment—hosting New Zealand Prime Minister John Key—becomes a crash course in navigating Facebook’s hierarchy. Requesting Mark Zuckerberg’s involvement backfires: Zuckerberg, disinterested in politics and preoccupied with Google’s competitive threat, openly rebuffs the idea.

The Prime Minister’s Visit: Chaos and Contrasts

Preparing for the visit reveals Facebook’s lack of protocol for political engagements. The author clashes with colleagues over logistics, such as excluding nonessential employees (dismissed as “Sheryl’s friends”) and managing expectations about New Zealand’s informal culture. The prime minister’s motorcade—a spectacle of armored vehicles and highway patrol—defies her assurances of Kiwi modesty, earning her ridicule. The visit itself devolves into absurdity: Zuckerberg, agitated by the disruption, reluctantly shakes Key’s hand for a photo op, while Sheryl Sandberg dazzles the room with charisma, steering conversations toward small talk and vacation plans instead of policy.

Sheryl Sandberg’s Star Power

Sandberg’s ability to charm the prime minister—and everyone else in the room—stands in stark contrast to Zuckerberg’s detachment. Her effortless shift from “stern professional” to “glamorous celebrity” leaves the author and colleagues “agog.” Yet the meeting’s lack of substance—reduced to wedding chatter and helicopter-tour recommendations—highlights a disconnect between the author’s policy-driven expectations and Facebook’s focus on personal relationships over formal diplomacy.

Key Takeaways

• Facebook’s cultural divide: Engineers reign supreme, while policy and politics are sidelined as “Sheryl’s world.”
• Leadership dynamics: Zuckerberg’s indifference to politics clashes with Sandberg’s polished, relationship-driven approach.
• Reality check: The author’s UN-inspired ideals collide with Facebook’s ad-hoc, personality-centric operations, foreshadowing challenges in bridging tech and governance.
• Humility (and humor): Early missteps—like the laptop fiasco—underscore the steep learning curve of adapting to Silicon Valley’s unspoken rules.

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Careless People Summary

4. Auf Wiedersehen to All That

Overview

This chapter captures a pivotal moment in Facebook’s early struggles to navigate international diplomacy, particularly with Germany—a nation deeply skeptical of the company’s data practices. The narrative centers on a disastrous meeting with German officials, revealing cultural misunderstandings, Facebook’s tone-deaf approach to governance, and the growing realization that the company’s "move fast and break things" ethos clashes with global regulatory expectations.

A Culture of Suspicion

Germany’s historical trauma—from the Gestapo to the Stasi—shapes its visceral distrust of centralized data collection. Unlike other nations, German officials view Facebook not as a benign social platform but as a potential surveillance apparatus. This skepticism puts Facebook on the defensive, as Germany pioneers early regulatory investigations into the company’s practices.

The Office Tour Debacle

The meeting begins with a tour of Facebook’s D.C. office, designed to reflect the company’s “unfinished” ethos: exposed ducts, concrete walls, and Nerf guns. To the German delegation, however, the chaotic aesthetic signals recklessness, not innovation. Questions about building code violations and the deliberate dismantling of “proper” office finishes highlight how Facebook’s branding backfires, reinforcing perceptions of immaturity and irresponsibility.

Marne’s Missteps

Marne, Facebook’s representative, compounds the tension. Her abrupt mention of being Jewish—ostensibly to preempt Holocaust-related discomfort—stuns the room into silence. Later, her attempt to contrast American free speech values with German cultural norms veers into awkward stereotyping (“Germans seem to enjoy sharing topless images”), alienating the delegation further. The exchange underscores Facebook’s lack of cultural nuance in high-stakes diplomacy.

Regulatory Collision Course

Discussions about content moderation and hate speech expose irreconcilable differences. Marne defends Facebook’s hands-off approach, rooted in U.S. free speech ideals, while the Germans demand proactive oversight. The meeting collapses into mutual frustration, foreshadowing Germany’s subsequent investigation into Facebook. The failure leaves the narrator questioning whether the company can truly adapt to global scrutiny.

Key Takeaways

• Historical context matters: Germany’s trauma with surveillance informs its stringent stance on data privacy, making it a regulatory pioneer.
• Symbolism backfires: Facebook’s “unfinished office” ethos, meant to signify innovation, instead signals irresponsibility to critics.
• Cultural diplomacy requires finesse: Tone-deaf remarks and stereotypes undermine trust, especially in high-stakes negotiations.
• Regulatory reckoning looms: The meeting’s collapse foreshadows inevitable clashes between Silicon Valley’s libertarian ideals and global governance demands.

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Careless People Summary

5. The Little Red Book

Overview

The chapter paints a vivid picture of Facebook’s early workplace culture, blending surreal displays of wealth, relentless work demands, and a quasi-ideological corporate ethos. Through personal anecdotes, the author navigates the stark contrasts between her own financial constraints and the “obscene wealth” of colleagues, while grappling with a work environment that demands total devotion. At the heart of it all is The Little Red Book—Facebook’s manifesto—which frames the company’s mission as a social revolution, blurring the line between capitalism and a higher calling.

Wealth and Status Symbols at Facebook

The author is immediately struck by the casual opulence around her. Colleagues flaunt luxury items—Louboutin heels, diamond bracelets, Louis Vuitton bags—that she initially doesn’t recognize. She learns that tenure, not titles, dictates wealth at Facebook: early hires amass fortunes through stock options traded in a booming private market. Assistants often out-earn executives, creating a bizarre hierarchy where flashy accessories become “armor” in an unspoken competition.

The Language of Economic Insensitivity

Facebook’s culture normalizes tone-deaf references to wealth. A director casually describes himself as “price insensitive,” while a colleague labels herself an “economic volunteer” due to her Google IPO windfall. The author, struggling to afford dual-city rent on her non-tech salary, feels alienated by this mindset. The divide between those for whom money is trivial and those for whom it’s a stressor becomes a constant undercurrent.

The Cult of Work: Stamina as Currency

Marne, the author’s boss, embodies Facebook’s work ethic: sleepless nights, 5:00 A.M. emails, and a life stripped of hobbies or downtime. Sheryl Sandberg later admits the grind is intentional—overloading employees to prevent “spare time” and foster loyalty. Office perks (free meals, laundry, transportation) are framed as tools to maximize productivity, not generosity. The author adapts to this “crushing intensity,” sacrificing sleep and personal life to keep pace.

The Little Red Book: Ideology and Indoctrination

Facebook’s employee handbook mirrors Mao’s Little Red Book, filled with Mark Zuckerberg’s aphorisms positioning the company as a social movement. Employees are told they’re “changing the world,” not just working a job. The author, initially inspired, helps craft foundational policies like Community Guidelines and transparency reports. Yet the rhetoric of “family” and “mission” masks a corporate reality, with older colleagues cautioning her against over-identifying with work.

Key Takeaways

• Tenure Over Titles: Early Facebook employees accrued life-altering wealth through stock options, creating a wealth gap disconnected from traditional hierarchies.
• Work as Identity: The company cultivated a culture where self-worth and success were tied to relentless productivity, enabled by “perks” designed to keep employees at work.
• Ideological Framing: The Little Red Book recast corporate goals as a humanitarian mission, blurring lines between profit and idealism to secure employee buy-in.
• Economic Divide: The author’s financial struggles highlighted the disconnect between Facebook’s “price insensitive” elite and those for whom the job was a paycheck.

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Careless People Summary

6. What Do We Stand For?

Overview

The chapter plunges into the whirlwind of Facebook’s policy team, where global crises—from political scandals to cultural clashes—collide daily. Amid the chaos, a central tension emerges: employees demand a coherent vision for Facebook’s role in the world, while leadership insists on pragmatism. The narrative traces the team’s struggle to define Facebook’s values, culminating in a contentious summit and a misguided organ donation initiative that exposes deeper fractures within the company’s power structure.

Internal Tensions and the Quest for Vision

The policy team’s Washington-based “boys”—political operatives accustomed to ideological battles—clash with leaders like Marne Levine, Sheryl Sandberg, and Mark Zuckerberg, who prioritize reactive problem-solving over grand visions. Marne dismisses the idea of Facebook as a “political force,” framing the company as a neutral platform focused on growth and profit. This disconnect fuels frustration among employees seeking purpose, prompting a summit to hash out Facebook’s mission.

The Organ Donation Debacle

At the summit, discussions devolve into superficial suggestions (e.g., pet adoptions) before pivoting to Joel Kaplan’s controversial proposal: aligning Facebook with global military initiatives. The idea collapses under scrutiny of its geopolitical implications, leaving a vacuum. Sheryl later unilaterally greenlights an organ donation campaign after a chance encounter with a Harvard surgeon. The initiative, intended to showcase Facebook’s altruism, quickly unravels due to legal, cultural, and ethical complexities—particularly around organ trafficking and data collection.

Sheryl vs. Mark: A Clash of Philosophies

The organ donation project becomes a battleground between Sheryl’s ambition to leverage Facebook’s influence and Mark’s insistence on platform neutrality. Sheryl pushes for a “megaphone” feature to aggressively promote organ donation, while Mark and engineers resist, fearing advocacy creep. Caught in the crossfire, the author is forced to defend Sheryl’s stance in a tense email exchange with Mark, who shuts down the idea with a terse dismissal: “Lam overruling you.” The conflict underscores Facebook’s lack of a unified ethical framework and the fragility of its internal hierarchies.

Key Takeaways

• Reactive vs. Visionary Leadership: Facebook’s leadership prioritized crisis management over a cohesive ideology, leaving employees adrift.
• Cultural Blind Spots: Initiatives like military alignment or organ donation ignored global sensitivities, revealing a U.S.-centric worldview.
• Power Dynamics: Sheryl’s influence clashed with Mark’s engineering-first ethos, exposing unresolved tensions about Facebook’s role as a neutral platform vs. an active societal player.
• Ethical Ambiguity: The organ donation saga highlighted Facebook’s struggle to balance business opportunism (e.g., data collection) with ethical responsibility.

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Careless People Summary

7. Show Him a Good Time

Overview

As Facebook’s IPO looms in April 2012, leadership grows anxious about retaining top talent—especially Javier “Javi” Olivan, the influential yet low-profile head of Facebook’s global growth team. Tasked with keeping Javi engaged, the narrator takes him to the Summit of the Americas in Cartagena, Colombia, aiming to blend high-stakes diplomacy with personal persuasion. What unfolds is a mix of awkward networking, surreal encounters, and a pivotal moment that reveals Javi’s conflicted loyalty to Facebook.

The Summit of (Unmet) Expectations

The trip begins with grand ambitions: rubbing shoulders with heads of state and positioning Facebook as a global player. Instead, the narrator and Javi are relegated to the sidelines, uninvited to official dinners and ignored by politicians. Efforts to force connections fall flat, but Javi remains unfazed, amused by the absurdity of their situation. The disconnect between Facebook’s self-importance and its actual clout in diplomatic circles becomes glaringly obvious.

Javi’s Growth Machine

Javi’s role at Facebook is dissected: his team drives aggressive, boundary-pushing strategies to expand the platform’s reach. Tactics like harvesting contacts without consent and the controversial “People You May Know” feature underscore a “growth-at-all-costs” ethos. The narrator likens this mentality to America’s historical recklessness—innovating first, asking questions later. Javi embodies this philosophy, balancing street smarts (like spotting Snapchat’s potential for sexting) with a cavalier attitude toward regulation.

The Bike Ride Confession

During a casual bike tour, Javi opens up about his post-IPO doubts. Torn between staying at Facebook to shape its future and pursuing his own ventures, he leans toward leaving. The narrator’s anxiety spikes—Elliot’s mission to retain him seems doomed. Javi’s ambivalence contrasts with his earlier enthusiasm, revealing the fragility of loyalty in Silicon Valley’s gold-rush culture.

Juan del Mar and the Unspoken Agenda

A dinner with Colombian tech CEOs and the enigmatic Juan del Mar—a bullfighter, restaurateur, and adult film star—takes a bizarre turn. The men’s inside jokes and veiled comments about the narrator’s role in “entertaining” Javi highlight the trip’s underlying awkwardness. The atmosphere shifts between camaraderie and exclusion, leaving the narrator questioning her assignment’s true purpose.

Hillary Clinton’s Midnight Salsa

The surreal climax unfolds in a gritty salsa club, where Javi spots Hillary Clinton dancing with her staff. The absurdity of the moment—a U.S. secretary of state in a sticky-floored Colombian dive bar—breaks the tension. Javi’s triumphant grin and the narrator’s shock cement the trip as a series of unpredictable, unforgettable experiences. Amid the chaos, Javi hints he’ll stay at Facebook… for now.

Key Takeaways

• Retention Through Spectacle: Facebook’s leadership relied on grand gestures and novel experiences to retain talent, even when those efforts bordered on the absurd.
• Growth vs. Ethics: Javi’s team epitomized Silicon Valley’s “move fast and break things” ethos, prioritizing expansion over accountability.
• The Human Factor: Despite strategic maneuvering, personal connections and spontaneous moments (like a salsa-dancing Hillary Clinton) often swayed career decisions more than corporate logic.
• The Illusion of Influence: Facebook’s perceived diplomatic clout was largely a facade, exposing the gap between tech’s self-image and its real-world reception among traditional power players.

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Careless People Summary

8. Running Out of Road

Overview

As Facebook’s stock cratered in 2012, desperation to reignite growth collided with Myanmar’s precarious political awakening. The company’s network effect strategy—dominating markets before rivals—led executives to chase 60 million potential users in a country where the military junta viewed social media as both a threat and a curiosity. Enter Sarah, a policy operative thrust into a surreal diplomatic dance: negotiating with generals who’d blocked Facebook while their citizens relied on it as the internet.

Her odyssey unfolds through bureaucratic labyrinths—hitchhiking past poverty-stricken villages to reach gilded ministry halls, trading awkward pleasantries with Aung San Suu Kyi under military surveillance, and enduring interrogations in throne rooms where officials admit they’ve spent years toggling Facebook’s access like a light switch. The fragile truce she brokers—temporary unblocking in exchange for vague promises of consultation—feels less like victory and more like feeding a beast.

Behind the geopolitical theater, personal fault lines crack open. Blistered feet and hunger gnaw at Sarah’s resolve until a searing call from her partner reveals a hidden pregnancy, exposing the recklessness of her mission. In a frigid hotel shower, she unravels: Was restoring Facebook’s access empowering Myanmar’s people or enabling a regime? Did her employer even care about the human cost of growth, or was she just a pawn in Zuckerberg’s spreadsheet?

The chapter pulses with moral vertigo—the collision of Silicon Valley’s scale-at-all-costs ethos with the raw complexities of a nation in transition. Every handshake with power brokers leaves residue, every compromise chips at certainty, and the fractured reality of doing business under authoritarianism stains even well-intentioned efforts. By the end, both Facebook’s mission and Sarah’s identity feel like sand slipping through clenched fists.

Facebook's Growth Crisis

By October 2012, Facebook’s stock price had plummeted by half since its IPO, plunging leadership into panic. With growth now essential to survival, executives fixated on expanding into untapped markets—countries with limited internet access, restrictive governments, or populations too young to legally use the platform. Myanmar, with 60 million potential users, became a priority after its military junta abruptly blocked Facebook. The company’s “network effect” strategy—locking users into Facebook before competitors could—was at risk.

The Myanmar Challenge

Myanmar’s block on Facebook coincided with its tentative steps toward democracy. The junta, unaccustomed to public criticism, saw the platform as a threat. For Facebook, losing Myanmar meant surrendering a massive growth opportunity. Policy executive Sarah was tasked with resolving the crisis, despite her reluctance to engage with a regime known for human rights abuses.

Navigating Nay Pyi Taw

Arriving in Myanmar’s eerily empty capital, Sarah faced logistical nightmares: no internet, sporadic electricity, and unreliable transport. She leveraged connections at the World Economic Forum (WEF) to infiltrate high-profile events, hoping to broker meetings with junta officials. The opulent WEF gatherings—contrasting starkly with Myanmar’s poverty—yielded no immediate leads, but a chance encounter changed everything.

A Chance Encounter with Aung San Suu Kyi

Sarah crashed a WEF luncheon honoring Aung San Suu Kyi, Myanmar’s pro-democracy leader. Seated at her table, Sarah seized a fleeting moment to connect, awkwardly introducing herself as both a New Zealander and a Facebook representative. Suu Kyi, sensing the junta’s scrutiny, cautiously introduced Sarah to Shwe Mann, a high-ranking junta official. His disbelief at meeting someone “from the internet” turned to curiosity—and led to an unexpected invitation.

Desperate Measures for a Meeting

The next morning, stranded without transport, Sarah resorted to hitchhiking on a deserted highway. After a chaotic ride with a confused local driver—aided by frantic miming and a $20 bill—she arrived late at the Ministry of Communications. Her passport confiscated, she was escorted to a cavernous, throne-lined hall, where a surreal encounter awaited.

Confronting the Junta

In a dim, intimidating chamber, Sarah faced two deputy ministers under blinding camera lights. The junta’s grievances spilled out: Facebook’s role in spreading anti-government sentiment and inflaming ethnic tensions. Myanmar’s internet, they explained, was Facebook for most users—a reality the company had ignored until growth pressures forced attention. The ministers admitted toggling Facebook’s access on and off for years, but now sought a fragile compromise: open communication channels. Yet practical barriers loomed, like the lack of government email addresses. “Could we call you on the telephone?” they asked, highlighting the chasm between Silicon Valley’s ambitions and Myanmar’s fractured reality.

Navigating Government Power Structures

The tense exchange at the Ministry of Communications sets the tone for subsequent meetings with Myanmar’s officials. The narrator encounters a range of intimidating figures—some in military regalia, others in traditional dress—all exuding unchecked authority. Their environments vary from sparse offices to opulent, gem-encrusted chambers resembling “Bond villains’ lairs.” Despite the palpable power imbalances and zero rapport, a fragile agreement is struck: Facebook will be unblocked temporarily, with a promise of prior consultation before future shutdowns. The victory feels hollow, though, as the inevitability of repeated censorship looms.

Physical and Emotional Collapse

By day’s end, exhaustion consumes the narrator—a “molecular” heaviness paired with hunger and mental fog. Blistered feet from navigating Myanmar’s rugged terrain add to the misery. Back at the hotel, a jarring call from Tom, her partner, shatters any remaining composure. His anger and fear over her radio silence crescendo into a revelation: she’s pregnant and hid it from Facebook, fearing professional repercussions. Tom’s frustration—rooted in concern for her safety and their unborn child—exposes the recklessness of her mission. The conversation leaves her raw, grappling with guilt and self-doubt.

A Crisis of Identity and Purpose

Alone in a cold hotel shower, the narrator confronts her unraveling resolve. Tears mix with icy water as she questions every decision: her loyalty to Facebook’s ambiguous mission, her handling of the junta, and her responsibility to Tom and their child. The once-unshakable trust in her instincts crumbles. She’s haunted by whether her actions served anyone—Myanmar’s people, Aung San Suu Kyi, or even Facebook—or if she’s become complicit in a system she no longer understands.

Key Takeaways

• Fragile Negotiations: Agreements with Myanmar’s regime are tenuous, hinging on opaque power structures and officials accustomed to absolute obedience.
• Personal vs. Professional Conflict: The narrator’s hidden pregnancy amplifies the ethical and emotional toll of high-stakes diplomacy, exposing vulnerabilities she’d suppressed.
• Erosion of Certainty: Once-confident convictions about Facebook’s role in Myanmar fracture under the weight of moral ambiguity and physical exhaustion.
• Human Cost: The chapter underscores the isolating, often dehumanizing grind of navigating authoritarian regimes—where even “success” feels fraught with compromise.

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Careless People Summary

9. Lady McNugget

Overview

The chapter captures a pivotal moment in Facebook’s evolution as Sheryl Sandberg’s Lean In catapults her into global celebrity, blurring the lines between her corporate role and personal brand. Told through the lens of a DC-based employee, the narrative reveals the contradictions between Sandberg’s public advocacy for workplace equality and the reality of her demands on staff—particularly women tasked with unpaid “office housework” to support her book launch. Against this backdrop, the author navigates a mix of admiration and disillusionment, culminating in a high-stakes diplomatic mission to Japan and a jarring incident involving a fabricated near-disaster.

The Lean In Paradox

Sheryl’s book promotes empowerment—encouraging women to “sit at the table” and reject self-doubt—but its launch exposes hypocrisy. Female employees in Facebook’s DC office are coerced into menial tasks like handing out name tags and shadowing Sheryl at events, work that mirrors the “office housework” she criticizes. Younger staff idolize her, while older colleagues dismiss Lean In as a tool to extract unpaid labor. The author, torn between awe and skepticism, witnesses how Sheryl’s celebrity overshadows her messaging, reducing genuine dialogue to scripted soundbites during a roundtable discussion.

Diplomacy and Disillusionment in Tokyo

The chapter shifts to Japan, where Sheryl’s book tour intersects with Facebook’s shaky foothold in the country. Tasked with arranging a meeting with Prime Minister Shinzo Abe, the author navigates absurd requests—like Sheryl’s insistence on bringing her parents to the PM’s office—and last-minute crises, including a meltdown over makeup that leaves a stylist in tears. The meeting itself is a diplomatic triumph, blending policy discussions about data privacy and disaster tools with Sheryl’s stealthy promotion of Lean In. Yet the author’s pride sours when Sheryl later berates her team for allowing her children to eat McDonald’s, despite having staged a PR photo of herself enjoying the same food.

The Mask of Celebrity

A post-tour flight incident crystallizes the author’s disillusionment. After Sheryl falsely claims on Facebook that her team narrowly avoided the fatal Asiana Airlines crash—a lie contradicted by their actual United flight—the author grapples with the erosion of trust. Sheryl’s willingness to exploit tragedy for publicity underscores the chasm between her curated image and reality. The chapter closes with the author reflecting on the corrosive nature of fame, symbolized by Sheryl’s “mask” of perfection, which ultimately alienates those closest to her.

Key Takeaways

• Hypocrisy in Action: Lean In’s ideals clash with the exploitation of female employees for Sheryl’s personal gain, exposing a gap between rhetoric and practice.
• Celebrity vs. Authenticity: Sheryl’s carefully crafted public persona unravels under pressure, revealing a willingness to manipulate narratives—even tragedies—for image control.
• The Cost of Loyalty: The author’s journey from admiration to disillusionment mirrors broader tensions at Facebook, where blind loyalty to leadership often overrides ethical concerns.
• Power and Perception: Sheryl’s insistence on curating reality (e.g., staged photos, false narratives) highlights the fragility of trust in corporate and personal branding.

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10. Only Good News

Overview

This chapter peels back the layers of Facebook’s workplace culture under Sheryl Sandberg’s leadership, revealing a toxic blend of arbitrary power displays, hypocrisy around work-life balance, and the emotional toll on employees. Through vivid anecdotes, it contrasts Sheryl’s public “Lean In” persona with her erratic, often cruel management style, while also exploring the author’s personal struggles to reconcile her idealism about Facebook’s mission with the reality of its corrosive environment—particularly for working mothers.

The “Only Good News” Meeting

During a routine meeting in Sheryl’s ominously named conference room, a colleague named Debbie arrives late due to traffic. Instead of starting the discussion, Sheryl forces the group to wait in silence, then publicly berates Debbie for her tardiness. The incident underscores Sheryl’s arbitrary use of humiliation as a control tactic, leaving employees perpetually anxious about unknowingly crossing invisible boundaries.

Power Dynamics and Public Humiliation

Sheryl’s outbursts aren’t isolated. At Davos, she erupts over a missing badge, blaming the author and her friend Marne despite their lack of responsibility. Marne advises compliance: “Take it. Just take responsibility.” Similarly, when Sheryl learns Angela Merkel declined a meeting, the team lies to avoid her wrath. Sheryl later fixates on the snub for months, revealing her obsession with status and inability to handle rejection.

Motherhood Under Facebook’s Expectations

The author’s experience exemplifies the impossible standards for working mothers at Facebook:

• Childbirth and Work: While in active labor, she drafts talking points for Sheryl, ignoring her husband and doctor’s pleas to stop.
• Nanny Pressure: Sheryl and Marne insist she hire a Filipina nanny, framing it as “smart” advice rooted in racial stereotypes. A subsequent childcare crisis—where the nanny is accidentally locked out, prompting a firefighter rescue—is later criticized as “unprofessional” to discuss at work.
• Performance Punishment: Post-maternity reviews penalize her for baby noises on calls and travel complications, reinforcing the expectation that motherhood remain invisible.

Hypocrisy and the “Lean In” Reality

Facebook’s rhetoric about authenticity and work-life balance clashes with its practices:

• Women’s Day Farce: Sheryl hosts a tone-deaf event where wealthy executives peddle sanitized stories of “balance,” erasing the role of paid help. Videos showcase pristine home gyms and photogenic families, obscuring the nannies and privilege enabling their lifestyles.
• Double Standards: Executives privately restrict their kids’ screen time and avoid posting about them online, even as Facebook pushes to onboard children through “Project Family.”
• HPM Propaganda: Sheryl’s internal memos glorify self-sacrifice, like missing family dinners for work, reframed as noble by Marne: “They should be proud of me.”

Key Takeaways

• Toxic Leadership: Sheryl’s volatility and public shaming fostered fear, ensuring compliance through unpredictability.
• Motherhood Penalty: Employees, especially women, faced punitive expectations to hide caregiving responsibilities, contradicting Facebook’s “authentic self” branding.
• Privileged Hypocrisy: Executives preached work-life balance while relying on underpaid labor and shielding their own families from the platform’s harms.
• Culture of Lies: From covering up Merkel’s rejection to performative Women’s Day narratives, dishonesty was normalized to protect Sheryl’s ego and Facebook’s image.

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11. Road Trip

Overview

The chapter opens with the visceral challenges of balancing breastfeeding and high-stakes international work travel. Amid Facebook’s ambitious Internet.org initiative—a project aimed at providing free, text-only internet access to underserved regions—the narrator is thrust into a whirlwind of diplomatic trips. What begins as a professional mission to secure partnerships for Internet.org collides with the physical and emotional toll of pumping breast milk in hostile environments. The narrative juxtaposes Mark Zuckerberg’s grand vision of global connectivity with the gritty reality of navigating motherhood in corporate and geopolitical landscapes.

The Internet.org Vision

Mark Zuckerberg’s 2013 paper frames internet access as a human right, proposing partnerships with telecom companies to deliver free, basic services (search, messaging, Wikipedia) to billions. The goal: hook users with free text-based tools, then upsell them to paid data plans. Early success in Africa with Facebook Zero—a stripped-down app—fuels optimism. However, Chile’s 2014 ban on free services threatens the initiative, prompting Facebook’s policy team to scramble for Latin American allies.

Colombia’s Jungle Diplomacy

To counter Chile’s rejection, the narrator and colleague Javi target Colombia’s government. A “road trip” into FARC-controlled jungle territory—meant to showcase connectivity gaps—turns perilous. Armored vehicles, military escorts, and off-road chaos amplify the narrator’s anxiety. Amid the danger, she battles engorgement from being unable to pump for hours, her pain secondary to survival instincts. The trip underscores the absurdity of corporate expectations: breastfeeding treated as an afterthought in life-threatening conditions.

Istanbul’s Pumping Nightmare

Two months later, a trip to Turkey escalates the pumping ordeal. A faulty outlet on a Turkish Airlines flight leaves the narrator stranded without power for her electric pump. By the time she reaches her hotel, desperation peaks: soaked clothes, agonizing pressure, and a hotel handyman’s horrifying misinterpretation of her need for “pumping.” A last-minute hand pump from a pharmacy finally brings relief, but the incident lays bare the systemic lack of support for working mothers in high-pressure roles.

Key Takeaways

• Corporate Blind Spots: The chapter critiques workplaces that prioritize mission-driven urgency over basic human needs, exemplified by the expectation to breastfeed/pump in unsafe, unsupported environments.
• Internet.org’s Contradictions: While framed as altruistic, the initiative relies on telecom companies’ profit motives, risking exploitation of low-income users.
• Motherhood in the Margins: The narrator’s physical and emotional struggles highlight the invisible labor of working mothers, particularly in male-dominated, globalized industries.
• Geopolitical Realities: Diplomatic efforts (e.g., courting Colombia’s president) reveal how tech giants leverage government partnerships to bypass regulatory hurdles, often ignoring local complexities.

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12. The Body

Overview

The chapter captures a pivotal moment as Facebook’s leadership prepares for a high-stakes trip to Asia, centered on South Korea—a country with an active criminal investigation targeting Mark Zuckerberg, Sheryl Sandberg, and other executives. Amid the tension, Mark’s irreverent attitude toward diplomatic protocols contrasts sharply with Sheryl’s meticulous preparation. Behind the scenes, the trip exposes Facebook’s fragile relationships with global governments, its rivalry with tech giants like Google, and a chilling corporate strategy to sacrifice employees as “bodies” to shield leadership from legal consequences.

Diplomatic Disarray and Corporate Arrogance

Mark’s refusal to take diplomatic etiquette seriously—mocking traditional bows with hip-hop gestures—highlights a broader pattern of dismissiveness toward international norms. This mirrors Facebook’s institutional arrogance: the company routinely challenges foreign laws, arguing that only U.S. and Irish regulations (where its international HQ resides) apply to its operations. South Korea’s arrest warrants stem from Facebook ignoring a legal requirement to submit games on its platform for government rating—a decision emblematic of its “move fast and break things” ethos.

The Asia Trip: Battling Google and Expanding Influence

The 2014 trip aims to strengthen Facebook’s foothold in Asia, where growth is critical. A key goal is courting Samsung to preload Facebook on its devices, reducing reliance on Google’s Android and Apple’s iOS. Internal tensions flare as Sheryl resists Mark’s involvement in political meetings, viewing them as her domain. Meanwhile, Facebook’s leadership fears Google’s dominance, recognizing that control over app stores and operating systems leaves Facebook vulnerable. Past failures, like the ill-fated “Project Buffy” phone, underscore the urgency to diversify partnerships.

Cannon Fodder in the Tech Cold War

The Korea crisis escalates when Facebook’s lawyers warn that arrest threats are “very real.” In a chilling strategy session, executives debate offering a sacrificial employee—“a body”—to test whether Korean authorities will act. The term “body” dehumanizes the act, reducing individuals to expendable assets. When silence falls over the room, all eyes turn to the narrator, the least senior person present, who realizes they’ve been designated as the pawn in this corporate gambit.

Key Takeaways

• Cultural Insensitivity as Policy: Mark’s mockery of diplomatic customs reflects Facebook’s broader disregard for local laws and norms, risking international backlash.
• Tech Power Struggles: Facebook’s dependency on Google and Apple drives desperate moves to secure alliances, like courting Samsung, while internal rivalries complicate leadership dynamics.
• Human Cost of Corporate Arrogance: The “body” strategy reveals a stark hierarchy where lower-ranking employees are treated as disposable shields for executives.
• Global Legal Reckoning: Facebook’s refusal to comply with foreign regulations—from Korea to Brazil and India—foreshadows escalating clashes between tech giants and nation-states.

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13. Stockholm Syndrome

Overview

The chapter captures a pivotal moment of personal reckoning as the narrator confronts the expectation to risk imprisonment in South Korea for her job at Facebook. Torn between loyalty to her employers and responsibility to her infant child, she grapples with the realization that her sense of obligation may stem from misplaced trust—a dynamic Tom, her partner, likens to Stockholm syndrome. What begins as a logistical dilemma evolves into a deeper examination of power, self-worth, and the cost of compliance within a corporate culture that prioritizes results over employee well-being.

The Choice: Duty vs. Self-Preservation

Preparing to face potential arrest abroad, the narrator initially accepts the assignment as an inevitable part of her role. Tom’s intervention—pointing out the absurdity of leaving her seven-month-old baby for indefinite detention—triggers a crisis of conscience. His accusation of Stockholm syndrome forces her to question her relationship with Facebook’s leadership (Sheryl, Elliot, and Marne), whom she’d trusted despite their escalating demands. The metaphor cuts deep, highlighting her internalized belief that she alone must “do the hard thing” to uphold responsibility—a mindset she ties to her identity as an eldest daughter.

Negotiating Freedom

In tense exchanges with Facebook’s legal and leadership teams, the narrator tests arguments to avoid the assignment: her breastfeeding infant, competing work priorities, and logistical impracticalities. She meets resistance until invoking Mark’s upcoming Asia trip as a reason she’s more valuable free than jailed. The coldly transactional resolution—prioritizing the company’s image over her safety—strips away any illusion of mutual care. This marks her first refusal of a directive, revealing the fragility of loyalty in a system that views employees as expendable assets.

Cracks in the Facade

The aftermath leaves the narrator disillusioned. Facebook’s leadership, once idealized, now appears indifferent to her humanity. She briefly considers quitting but hesitates, citing the challenges of job-hunting with a newborn. Instead, a female colleague—new and eager to prove herself—is sent in her place. The colleague’s success in avoiding arrest secures a smooth path for Mark and Sheryl’s trip, underscoring the company’s willingness to exploit those with less power. The narrator’s lingering doubts about her colleague’s autonomy (“maybe she didn’t feel like she had a choice either”) mirror her own earlier resignation.

Key Takeaways

• Corporate Loyalty vs. Self-Worth: Blind allegiance to an organization can mirror abusive dynamics, where employees rationalize exploitation as duty.
• The Illusion of Choice: Hierarchical power structures often limit perceived agency, particularly for women and caregivers.
• Clarity Through Resistance: Refusing a directive—even once—can expose systemic indifference, reshaping one’s understanding of workplace relationships.
• The Cost of Compliance: The narrator’s colleague stepping into the same risk highlights how systems recycle vulnerability, relying on those least empowered to say no.

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14. Five Settlers and One Billionaire in Catan

Overview

The chapter captures the surreal experience of traveling with Mark Zuckerberg and his inner circle, blending humor, discomfort, and sharp observations about power dynamics. From navigating the unspoken rules of private jet etiquette to awkwardly confronting workplace hierarchies during a board game, the narrative highlights the dissonance between the author’s grounded perspective and the rarefied world of billionaire executives.

Private Jet Paradoxes

The author’s first private jet experience is riddled with missteps, from naively suggesting layovers to struggling with the plane’s hidden toilet. The jet’s bland, utilitarian design contrasts with its exclusivity, mirroring Mark’s personal tastes: fast food replaces gourmet meals, and a single flight map substitutes for entertainment. The seating arrangement becomes a silent power struggle, culminating in the author accidentally landing a seat beside Mark—a position both privileged and socially perilous.

Amanjiwo: Luxury and Vulnerability

At Indonesia’s Amanjiwo resort, Mark’s “citadel-like” suite becomes a backdrop for discomfort. A planned solo swim turns into a group activity, forcing the author to confront insecurities about her postpartum body and scars from a past shark attack. A frantic gift-shop scramble for a modest swimsuit underscores the tension between personal privacy and workplace expectations. Meanwhile, Mark’s casual remark about potentially missing his child’s birth reveals a jarring disconnect between his priorities and conventional familial bonds.

Settlers of Catan: Power Plays Exposed

A late-night game of Settlers of Catan lays bare the unspoken sycophancy surrounding Mark. Teammates blatantly manipulate gameplay to ensure his victory, sparking the author’s frustrated accusation. While others feign ignorance or defend their actions, Mark remains oblivious, highlighting his insulation from criticism. The incident fractures the group’s camaraderie, leaving the author isolated in her refusal to participate in the charade.

Photo Ops and Reality Checks

During temple visits, Mark’s attempts to play “man of the people” backfire. After successfully photographing tourists at Borobudur, he’s rebuffed at Prambanan by a group unaware of his fame. His visible dejection—and the author’s poorly suppressed laughter—underscore his inability to process ordinary social rejection. The moment punctures his curated persona, revealing a fragility beneath the billionaire exterior.

Key Takeaways

• Hierarchy in Plain Sight: Unspoken rules govern interactions with power figures, from jet seating to rigged board games.
• The Cost of Conformity: Dissent—even over trivial matters—risks social exclusion in high-stakes environments.
• Authenticity vs. Performance: Mark’s blend of obliviousness and vulnerability clashes with his team’s relentless image management.
• Isolation at the Top: Extreme wealth and status create barriers to genuine connection, both for leaders and those orbiting them.

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15. A Simple Request

Overview

The chapter opens with Mark Zuckerberg’s unusual demand during a high-stakes Asia tour: he wants his team to orchestrate a riot or peace rally to surround him with a massive crowd. Confusion and tension escalate as the team navigates cultural missteps, logistical chaos, and a surreal meeting with Indonesia’s president-elect, revealing deeper themes about Facebook’s influence and the blurred line between online platforms and real-world power.

The Batik Shirt Standoff

Mark’s refusal to wear a traditional Indonesian batik shirt for his meeting with President-Elect Joko Widodo sets off a chain of delays. His aversion to the vibrant, culturally significant garment clashes with diplomatic expectations, leading to a wardrobe stalemate. The situation grows more fraught when Mark splits his pants, forcing his assistant Andrea to improvise a fix. The team’s tardiness—blamed on Jakarta’s infamous traffic—heightens the pressure as they scramble to salvage the critical meeting.

Mob Chaos at City Hall

Upon arriving late to Jakarta’s city hall, the team is engulfed by an aggressive, unplanned mob. Press and fans surge forward, separating the group and nearly sparking violence when Facebook’s security chief confronts a high-ranking Indonesian official. The narrator is swept off her feet in the frenzy, losing shoes and composure. The chaos, far from the “gentle mob” Mark envisioned, underscores the unpredictability of public fervor—and the dangers of conflating online engagement with physical control.

Inside the Meeting: Politics and Pop Stars

The disheveled team finally enters the meeting, where Mark and President-Elect Widodo (“Jokowi”) discuss Facebook’s role in Indonesian politics. Jokowi credits Facebook for his outsider victory, dubbing himself the “Facebook president.” The scene takes a surreal turn when a flamboyant Indonesian pop star—seated prominently beside Jokowi—reveals the blurred lines between politics, celebrity, and social media. The meeting’s loose structure and Jokowi’s earnest optimism highlight Facebook’s early idealism about its power to democratize leadership, while hinting at unspoken risks.

Key Takeaways

• Power and Peril of Influence: Mark’s obsession with mobilizing crowds reflects Facebook’s ambition to translate online networks into real-world clout—a dangerous gamble.
• Cultural Diplomacy Failures: The batik shirt standoff symbolizes Silicon Valley’s frequent blind spots in navigating global cultural norms.
• Uncontrolled Chaos: The unintended mob scene exposes the volatility of public attention, even without deliberate manipulation.
• Political Partnerships: Jokowi’s gratitude underscores Facebook’s early role as a kingmaker in politics, foreshadowing later debates about tech’s responsibility in democracy.

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16. Just Keep Driving

Overview

The chapter captures a high-stakes, chaotic day as the narrator navigates the fallout of arranging a spontaneous public appearance (“blusukan”) between Mark and Indonesia’s president-elect, Jokowi. What begins as a diplomatic victory quickly spirals into a security nightmare, testing alliances and exposing raw tensions within the team.

Tension and Security Concerns

After securing Mark’s participation in Jokowi’s blusukan—a populist walkabout—the plan unravels when security risks emerge, including sniper threats. Mark’s assistant, Andrea, cancels the event, but the president-elect’s team unexpectedly revives it with a last-minute location change. The narrator’s team, particularly Elliot (Mark’s advisor), vehemently opposes the move, fearing for Mark’s safety.

Behind-the-Scenes Negotiations

A power struggle unfolds: Elliot tries to veto the blusukan, while Mark, visibly energized by the challenge, insists on proceeding. The narrator is caught mediating between Jokowi’s insistent team, Mark’s defiance, and Elliot’s fury. Security head Todd grows increasingly agitated as Mark departs with the president-elect, leaving his detail scrambling to catch up.

The Blusukan Unfolds

The relocated event at a Jakarta shopping mall descends into pandemonium. Swarms of emotional crowds mob Jokowi, largely ignoring Mark. Security teams are overwhelmed, with Todd fighting through the chaos. Mark and Jokowi, however, thrive in the frenzy, bonding amid the adulation. The narrator’s team is physically battered by the crowd, their cohesion fraying as they struggle to stay together.

Aftermath and Reflections

Escaping the mall, the van ride reveals starkly different reactions: Mark is euphoric, awed by Jokowi’s connection with the public, while Elliot seethes, blaming the narrator. The mood shifts when the team realizes they’ve abandoned a colleague in the chaos. Elliot’s terse order—“Just keep driving”—underscores the day’s ruthlessness. Mark’s exhilaration contrasts with Todd’s trauma and the narrator’s dread of professional fallout.

Key Takeaways

• Risk vs. Reward: Mark’s thrill at the blusukan highlights his appetite for high-impact, visceral experiences, even when they defy security protocols.
• Power Dynamics: The clash between diplomatic ambition (the narrator), personal safety (Elliot/Todd), and Mark’s unpredictability reveals fractured priorities within the team.
• Cultural Capital: Jokowi’s grassroots appeal stuns Mark, offering him a rare glimpse of a leader whose public devotion surpasses his own.
• Human Cost: The abandoned colleague and Todd’s panic underscore the sacrifices and chaos buried beneath high-profile diplomacy.

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17. Going Down in a Blaze of Glory

Overview

The chapter captures a pivotal leg of Facebook’s Asia tour, oscillating between the chaos of team dynamics, strained diplomatic efforts, and introspective moments that reveal Mark Zuckerberg’s personality and priorities. From South Korea’s political rebuffs and a turbulent, revelry-filled flight to Japan’s diplomatic breakthroughs, the narrative juxtaposes the absurdity of corporate excess with the fragile beginnings of tech-driven statecraft. Alongside these events, the author grapples with personal loneliness and ethical discomfort as wealth, power, and environmental concerns collide.

Diplomatic Hurdles in South Korea

The team’s attempts to secure a meeting with South Korea’s president fall flat after Facebook refuses to offer financial incentives—a stark contrast to Google’s approach. Samsung’s lukewarm reception and the ensuing karaoke party underscore the trip’s lack of substantive progress. The private jet ride to Tokyo devolves into drunken antics, with Mark enthusiastically leading Backstreet Boys sing-alongs. Amid the chaos, the author feels isolated, yearning for her infant daughter while observing Mark’s childlike demeanor.

Mark’s Unfiltered Persona

The flight’s turbulence amplifies the team’s recklessness, as they drunkenly belt Bon Jovi’s “Blaze of Glory” while the plane shakes violently. The author and a terrified flight attendant exchange glances, highlighting the disconnect between the team’s euphoria and the looming danger. These moments crystallize the author’s evolving view of Mark: a billionaire CEO whose idea of “cutting loose” feels oddly juvenile and isolating, stripped of the gravitas his role demands.

Wealth, Priorities, and Ethical Disconnects

Conversations about wealth reveal Sheryl Sandberg’s cynical take on the “cycle of wealth”—exotic travel, fitness obsessions, and eventual personal crises. Mark, however, fixates on luxury food, citing SoftBank CEO Masayoshi Son’s indulgence in endangered bluefin tuna. The author, drawing on her environmental advocacy, is unsettled by the casual disregard for conservation. Mark’s admiration for Andrew Jackson—praised for his ruthlessness and “getting stuff done,” while ignoring atrocities like the Trail of Tears—further underscores ethical blind spots.

Japan: A Diplomatic Bright Spot

In contrast to South Korea, Japan marks a success. Prime Minister Shinzo Abe praises Facebook’s disaster response tool (inspired by Japan’s 2011 tsunami) and breaks protocol to endorse it publicly. The meeting reflects growing trust, with Abe pledging to visit Facebook’s headquarters. The author notes the careful diplomacy behind this progress, including wearing a different dress to avoid repeating outfits from prior visits—a subtle nod to cultural nuance.

Key Takeaways

• Diplomacy vs. Ego: Facebook’s refusal to “pay to play” in South Korea highlights the tension between corporate principles and political access.
• Mark’s Paradox: His blend of earnestness and naivety—whether singing karaoke or idolizing Andrew Jackson—reveals a leader grappling with the weight of his influence.
• Ethical Ambiguity: The indulgence in endangered species and historical hero-worship expose troubling priorities among tech elites.
• Tech Diplomacy’s Potential: Japan’s successful collaboration with Facebook demonstrates how technology can foster tangible, socially impactful partnerships—when executed thoughtfully.
• Looming Challenges: The chapter closes ominously, hinting at the fragility of these gains as the team prepares to enter China—a market fraught with political and ethical landmines.

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18. Red Flag

Overview

This chapter delves into Facebook’s aggressive pursuit of entering the Chinese market in 2014, driven by Mark Zuckerberg’s conviction that connecting China is the final frontier in the company’s mission to “connect the world.” Amidst growing internal debates about ethics and strategy, the narrative highlights the tensions between business ambitions and moral compromises, particularly as protests in Hong Kong and government censorship complicate efforts. Key players like Vaughan Smith, Facebook’s newly appointed China lead, clash with policy experts over tactics, while Instagram’s sudden blockage in China exposes the fragility of the company’s position.

The Strategic Push for China

Mark views China as the last major hurdle in Facebook’s global expansion. In a 2014 email to executives, he outlines a three-year plan to establish operations there, emphasizing Instagram’s existing foothold as a potential gateway. His urgency stems from the belief that without immediate action, Chinese authorities could block all Facebook-owned services. The email notably omits any discussion of ethical concerns, framing China purely as a logistical challenge rather than a moral dilemma.

Ignored Moral Complexities

The chapter contrasts Mark’s pragmatic approach with Google’s earlier withdrawal from China over censorship and human rights issues. Sheryl Sandberg and Elliot Schrage, both former Google executives familiar with these debates, are silent on the moral implications in internal discussions. Instead, Facebook’s leadership focuses on partnerships and political maneuvering, treating China’s authoritarian policies as obstacles to bypass rather than reckon with.

Vaughan Smith’s Unconventional Tactics

Vaughan Smith, a corporate development executive with no China expertise, is tasked with leading the charge. His strategy leans on personal networking—golf outings, venture capital connections, and leveraging his affable persona—rather than policy expertise. Internally, his team floats controversial ideas, including granting Chinese authorities access to Hong Kong users’ data, a proposal that would violate existing privacy agreements. Junior staffers flag the legal risks, but Vaughan dismisses concerns, prioritizing relationship-building over due diligence.

Hong Kong’s Umbrella Revolution and Instagram’s Downfall

As pro-democracy protests erupt in Hong Kong, Instagram becomes a key tool for activists. China retaliates by blocking the platform, undermining Facebook’s fragile progress. Internal blame falls on the policy team for earlier missteps, including a voter engagement campaign during Hong Kong elections that angered Chinese officials. Vaughan’s initial optimism fades, but he pivots to advocating for a pro-Beijing narrative, suggesting public statements praising China’s “rule of law” during the crackdown—a stance met with fierce internal criticism.

Clash Over Ethics and Strategy

Elliot Schrage and policy lead Debbie rebuke Vaughan’s suggestion to align with China’s suppression of protests, invoking the Nuremberg defense analogy to highlight the dangers of legitimizing authoritarian actions. Vaughan’s dismissive response—thanking Elliot for “articulate background” without engaging the critique—underscores the disconnect between business objectives and ethical accountability.

Key Takeaways

1. Ambition vs. Ethics: Facebook’s leadership prioritizes market expansion over moral scrutiny, treating China as a puzzle to solve rather than a regime to confront on human rights.
2. Cultural Missteps: Vaughan’s lack of regional expertise and reliance on personal charm highlight systemic flaws in Facebook’s approach to geopolitics.
3. Fragile Foundations: Instagram’s abrupt blockage and internal discord reveal the risks of operating in authoritarian markets without transparent safeguards.
4. Red Flags Ignored: Proposals to share user data with Chinese authorities and downplay protests signal a willingness to compromise core values for access—a precedent with far-reaching consequences.

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19. PAC-Man

Overview

The chapter delves into the aftermath of Marne’s departure from Facebook’s policy team and the arrival of her replacement, Joel Kaplan—a figure whose political background and worldview starkly contrast with the global, deliberative approach of his predecessor. As the narrative unfolds, tensions rise over Facebook’s evolving strategy to monetize political influence, exposing ethical dilemmas and cultural clashes within the company’s leadership.

Leadership Shifts and Tribal Dynamics

Marne’s exit leaves a void, both professionally and personally, for the narrator, who had grown accustomed to her meticulous, questioning style. Joel Kaplan, a Republican operative with deep ties to the George W. Bush administration, steps into her role. His appointment highlights Facebook’s insular leadership culture—a “tribe” of interconnected elites whose loyalties lie more with each other than with broader ideologies. Joel’s career, marked by his role in the 2000 Brooks Brothers riot and resentment over his portrayal in Too Big to Fail, underscores his partisan identity and transactional view of power.

A U.S.-Centric Worldview

Joel’s focus on American politics blinds him to global complexities. He struggles with basic geography (e.g., not knowing Taiwan is an island) and defaults to leveraging U.S. institutions like the State Department to solve international issues, treating them as extensions of Facebook. When Nauru blocks the platform, Joel pressures the U.S. government to intervene publicly—a move the narrator argues is ineffective compared to direct diplomatic engagement. His lack of curiosity about non-U.S. contexts becomes a recurring friction point.

Monetizing Politics: Ads and PACs

Joel’s mandate shifts the policy team toward revenue generation, particularly through political advertising. He sees elections as lucrative opportunities to embed Facebook into the electoral process, ensuring politicians rely on the platform—and thus protect it from regulation. A team of Harvard graduates is hired to sell ads to campaigns, a strategy the narrator finds ethically troubling. The conflict peaks when Joel pushes to establish Political Action Committees (PACs) abroad, unaware that foreign financial contributions to elections are illegal in most democracies. The narrator’s pushback—highlighting how this could equate to bribery—reveals a stark divide between Joel’s profit-driven pragmatism and global ethical standards.

Clash of Values

The narrator, shaped by New Zealand’s strict campaign finance laws, critiques the U.S. model of money-dominated elections and resists exporting it via Facebook. Joel’s insistence on monetizing political influence abroad—even joking about funneling money to dictatorships—exposes a willingness to bend norms for corporate gain. This ideological rift underscores broader tensions within Facebook: balancing business imperatives with the societal impact of its policies.

Key Takeaways

• Tribal Leadership: Facebook’s executive circle prioritizes personal loyalties and shared histories over diverse perspectives.
• Profit Over Principles: Joel’s focus on revenue transforms the policy team into a sales arm, prioritizing political advertising despite ethical concerns.
• Global Ignorance: A U.S.-centric worldview leads to tone-deaf strategies in international markets, risking legal and reputational fallout.
• Ethical Boundaries: The push to establish foreign PACs highlights the dangers of applying American political tactics globally, where they may violate anti-corruption laws.
• Cultural Divide: The narrator’s outsider perspective clashes with Facebook’s insular, profit-driven culture, foreshadowing broader systemic conflicts.

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20. Slouching Toward Autocracy

Overview

This section traces the escalating centralization of decision-making power at Facebook, particularly around content moderation and government relations. It highlights Mark Zuckerberg’s growing involvement in politically sensitive cases, often overriding established policies to prioritize business interests. Conflicts with governments, internal dissent, and the erosion of transparency underscore the company’s drift toward autocratic governance under Mark’s unilateral control.

The Navalny Event and Internal Turmoil

In December 2014, Facebook blocked a Russian event page supporting opposition leader Alexei Navalny after pressure from Roskomnadzor, Russia’s internet regulator. The move sparked backlash in the tech community, prompting Sheryl Sandberg to defend the decision as necessary to keep Facebook operational in Russia. Mark, however, was furious the issue wasn’t escalated to him. He argued that while compliance with local laws might be unavoidable, such decisions should ultimately rest with him.

The U.S. State Department intervened, urging Facebook to resist censorship even if it meant being shut down in Russia. Joel Kaplan, Facebook’s policy chief, clashed with officials over this stance, calling it unrealistic. Internally, tensions flared as Mark began demanding direct oversight of content removals in “sensitive countries,” bypassing long-standing protocols.

From Chaos to Community Standards

The chapter reflects on Facebook’s early content moderation struggles, such as refusing to remove offensive pages like “Occupy Tony Abbott’s Daughters’ Vaginas” until public outcry forced reforms. A dedicated policy team eventually crafted the Community Standards, a public framework for content decisions. These rules aimed to balance free expression with accountability, distancing moderation from ad sales teams and political whims.

By 2015, however, Mark began sidelining these standards. He personally ordered removals of content—like a Mexican school shooting video or Indonesian coup threats—that didn’t violate the rules but risked angering foreign leaders. These decisions often aligned with Facebook’s expansion goals, prioritizing market access over principle.

Employee Backlash and Autocratic Edicts

At a 2015 offsite meeting, policy and communications staff—particularly those from high-risk countries like South Korea and Brazil—raised alarms. They questioned how Mark could unilaterally assess political risks in their regions or protect employees facing arrest. Joel dismissed their concerns, doubling down on Mark’s two criteria for compliance: 1) imminent shutdown of Facebook or 2) physical threats to employees.

This approach effectively invited governments to escalate pressure tactics. Employees feared the lack of clear guidelines left them vulnerable, while Mark’s public rhetoric about free speech (e.g., post-Charlie Hebdo) clashed with his behind-the-scenes concessions.

The Rise of One-Man Rule

By centralizing power, Mark transformed Facebook into an autocracy. Content decisions once guided by team consensus and public standards now hinged on his personal judgment. Sheryl and other leaders were sidelined, leaving no checks on executive authority. The chapter concludes with a stark observation: Facebook’s survival increasingly depended on appeasing authoritarian regimes, while its internal culture eroded into top-down decrees.

Key Takeaways

• Centralized Power: Mark Zuckerberg’s unilateral decisions undermined Facebook’s established policies, prioritizing business growth over transparency.
• Business Over Principles: Content removals increasingly aligned with geopolitical interests, contradicting public commitments to free expression.
• Employee Risks: Frontline staff in repressive regions faced heightened danger as governments learned to exploit Facebook’s reliance on threats.
• Authoritarian Incentives: By tying compliance to shutdowns or arrests, Facebook incentivized regimes to escalate coercion.

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21. Billionaire Time

Overview

The chapter opens with a high-stakes diplomatic effort to secure a joint appearance between Mark Zuckerberg and Colombian President Juan Manuel Santos to promote Facebook’s Internet.org initiative in Latin America. The plan hinges on navigating the clashing schedules of two powerful figures: a tech CEO notorious for his aversion to morning commitments and a head of state embroiled in peace talks with the FARC guerrillas. What follows is a chaotic chain of miscommunications, logistical disasters, and cultural clashes that jeopardize the partnership and reveal the fragility of bridging Silicon Valley’s priorities with global political realities.

The Scheduling Standoff: Power vs. Protocol

President Santos’ team insists on a noon meeting, but Zuckerberg’s team demands a 12:30 P.M. start time—a non-negotiable boundary rooted in Mark’s nocturnal work habits. The standoff highlights a tension between Silicon Valley’s “time ownership” culture and the rigid protocols of international diplomacy. After days of back-and-forth, Santos’ staff reluctantly agrees to 12:15 P.M., only for Zuckerberg’s team to unilaterally revert to 12:30 P.M. the day before the event. The Colombian side reaffirms the original noon timing, exposing a disconnect in power dynamics: even billionaires can’t bend the schedules of heads of state.

Logistical Meltdown: A Comedy of Errors

On the day of the meeting, a critical hotel mix-up leaves the narrator stranded at the wrong Marriott, miles from Zuckerberg’s location. With the meeting minutes away, she sprints barefoot through Bogotá’s streets, haphazardly flagging down a van while fielding panicked calls from both teams. The scene underscores the fragility of high-profile coordination—and how easily minor oversights (like confirming hotel names) can spiral into diplomatic crises. Meanwhile, Zuckerberg arrives unprepared, having ignored briefing materials, and faces Santos coldly prioritizing peace talks over Facebook’s pitch.

The Unraveling: Awkwardness and Aftermath

The actual meeting lasts less than ten minutes. Santos, visibly impatient, emphasizes the urgency of his peace negotiations, while Zuckerberg fumbles through vague promises about Internet.org. The president abruptly exits, leaving Zuckerberg alone onstage for a truncated Q&A session. The fallout is immediate: Colombia backtracks on commitments to integrate government services into Internet.org, and Facebook’s regional influence dwindles. The incident becomes a case study in how perceived disrespect and poor preparation can torpedo even the most strategically aligned partnerships.

Key Takeaways

• Time as a Power Currency: Zuckerberg’s insistence on controlling his schedule—a privilege unchecked in Silicon Valley—clashes with the nonnegotiable demands of international diplomacy.
• Logistical Hubris: Assuming seamless execution without contingency planning risks reputational damage, especially in high-stakes political environments.
• The Cost of Unpreparedness: Failing to respect a leader’s priorities (e.g., Santos’ peace talks) undermines trust and collaboration.
• Diplomatic Fallout: Broken commitments, like Facebook’s refusal to support FARC-related content post-meeting, erode long-term partnerships.
• Cultural Divide: The episode exposes Silicon Valley’s insularity and its struggle to navigate global political ecosystems beyond tech-centric logic.

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22. Hunger Games for the 0.001 Percent

Overview

The chapter pulls back the curtain on the surreal world of Davos, where global elites gather to jockey for status while navigating a labyrinth of logistical nightmares. The author’s decision to bring her infant daughter to the event exposes the stark incompatibility of parenthood with the high-stakes, ego-driven environment. Against this backdrop, Facebook’s strategic maneuvering—from tax avoidance schemes to cozying up to politicians—reveals a company prioritizing self-interest over ethical responsibility, even as internal dissent brews over the consequences.

The Social Hierarchy of Davos

Davos operates as a hyper-competitive status arena, where every detail—from hotel choices to seating arrangements—is meticulously scrutinized. Attendees obsess over perceived slights and rankings, turning the event into a “status Olympics” for the ultra-wealthy. The scarcity of resources (hotel rooms, transportation) amplifies this hierarchy, creating a pressure cooker of envy and one-upmanship. For the author, the chaos is compounded by caring for a sick child in a town ill-equipped for basic human needs, highlighting the disconnect between Davos’ glamorous facade and its impractical reality.

Facebook’s Tax Gambit

A pivotal meeting with Irish Prime Minister Enda Kenny underscores Facebook’s ruthless tax avoidance strategies. Despite the EU shutting down the “double Irish” loophole, Kenny offers a new scheme—the “Knowledge Development Box”—to let tech giants pay even lower rates on intellectual property income. Sheryl Sandberg pushes for Facebook to shape the policy details, while the author grapples with the moral discomfort of backroom deals that prioritize corporate profit over public good. The exchange lays bare how small nations like Ireland are forced to cater to tech giants to retain jobs, even as austerity measures cripple their economies.

Sheryl’s Power Play

Sheryl’s post-Davos strategy email reveals her focus on leveraging Facebook’s political influence. Ignoring warnings about rising global backlash, she doubles down on making Facebook indispensable to politicians’ electoral success. This includes coaching campaigns on targeted messaging and expanding teams worldwide to embed Facebook into the machinery of power. The author argues against this approach, fearing it will entangle Facebook with controversial figures and alienate future governments, but her concerns are dismissed.

The Human Cost of Ambition

Amidst the wheeling and dealing, the author’s personal struggles—crawling through coatrooms to retrieve a colleague’s lost boots, missing her daughter’s birthday—highlight the dehumanizing grind of corporate loyalty. The chapter juxtaposes Davos’ cold calculus of power with moments of vulnerability, questioning the sustainability of a culture that demands employees “work as if they don’t have children.”

Key Takeaways

• Davos as a Microcosm: The event exemplifies how global elites perpetuate a system obsessed with status and access, often at the expense of practicality and empathy.
• Ethical Trade-Offs: Facebook’s tax avoidance and political maneuvering prioritize short-term gains over long-term trust, exposing the company to regulatory blowback.
• Power Dynamics: Small nations like Ireland are squeezed into enabling corporate tax evasion to retain economic benefits, highlighting systemic inequities.
• Internal Dissent: The author’s marginalized voice reflects broader tensions between ethical responsibility and corporate ambition within tech giants.
• Human Toll: The relentless demands of high-powered careers clash starkly with personal well-being and family life, underscoring the unsustainable costs of “leaning in.”

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23. Making Sure This Thing Flies

Overview

The chapter captures a pivotal moment in Facebook’s push to expand Internet.org, focusing on a high-stakes diplomatic and logistical scramble at the 2015 Summit of the Americas in Panama. Mark Zuckerberg’s team navigates political maneuvering, chaotic crowds, and tense negotiations with world leaders—particularly Brazil’s president—to secure partnerships for the initiative. While the summit brings unexpected wins and camaraderie, it also exposes vulnerabilities in Facebook’s strategy and the complexities of global tech diplomacy.

Summit Strategy and Diplomatic Chaos

To revive momentum for Internet.org, the team orchestrates Mark’s participation in a high-profile panel with President Obama and Latin American leaders. After backroom negotiations, Mark is sidelined from the panel but gains visibility when Obama publicly acknowledges him. Seizing the moment, Mark promotes Internet.org during a Q&A, framing connectivity as a global priority. The gambit works: leaders echo his messaging, and telecom operators previously resistant to Internet.org suddenly seek partnerships.

The scene descends into chaos as Mark exits—security struggles to navigate a mob of attendees, culminating in an awkward clash with the president of Guatemala. The incident becomes an inside joke among the team but underscores the frenetic energy of the summit.

Momentum and Unresolved Challenges

The summit yields tangible wins: 30 new partnerships and a surge in political interest. Mark’s team celebrates with lighthearted moments, including a miscommunication over “delicacy” vs. “delicatessen” and a surreal encounter with a New Zealand container ship. However, cracks emerge beneath the surface. Mexico’s stalled rollout and Brazil’s skepticism threaten progress.

Brazil’s president, Dilma Rousseff, proves a formidable opponent. A last-minute meeting with her—delayed by an unscheduled Obama rendezvous—reveals her deep concerns about zero-rating and Facebook’s reluctance to invest in physical infrastructure. Despite Mark’s offers to launch the Internet.org app and visit Brazil, Rousseff remains noncommittal, later downplaying discussions about the initiative publicly.

The Brazilian Standoff

Brazil’s resistance highlights broader tensions. As a global leader in internet regulation, its stance could influence other nations. Rousseff’s demand for tangible infrastructure (like drones) clashes with Facebook’s focus on software-driven solutions. The team realizes their strategy may lack the substance needed to win over skeptical governments, setting the stage for future battles.

Key Takeaways

1. Diplomatic Theater: Public endorsements from world leaders temporarily buoy Internet.org, but real progress hinges on behind-the-scenes negotiations.
2. Brazil’s Leverage: As a regulatory powerhouse, Brazil’s skepticism forces Facebook to confront gaps in its infrastructure promises.
3. Celebration vs. Reality: While the summit generates momentum and team bonding, unresolved challenges in key markets foreshadow deeper struggles.
4. Power Dynamics: Even tech giants like Facebook must navigate complex political hierarchies—sometimes at the cost of awkward confrontations.

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24. California Time

Overview

The chapter captures a pivotal moment in the narrator’s career as mounting pressure from Mark Zuckerberg to relocate to California clashes with her personal life in New York. Amid high-profile meetings with global leaders like Japanese Prime Minister Abe, subtle tensions over geography and power dynamics underscore Silicon Valley’s growing influence. What begins as lighthearted banter evolves into a strategic push, culminating in a rare, carefully worded email from Mark that forces a life-altering decision.

The Geography of Power

The narrator navigates Mark’s persistent, if understated, campaign to bring her closer to Facebook’s Menlo Park headquarters. Their exchanges—framed as playful jabs about New York’s merits—mask a deeper recognition of Silicon Valley’s rising political clout. As world leaders like Abe treat Facebook’s HQ as a “West Coast White House,” the unspoken truth becomes clear: proximity to Mark and the tech epicenter is becoming non-negotiable for shaping global policy.

The Email That Changed Everything

Mark’s unexpected May 2015 email—a rare gesture of praise—serves as a tactical nudge. The narrator dissects its subtext: while ostensibly thanking her for securing meetings with heads of state, it signals an ultimatum. Known for avoiding affirmations, Mark’s words carry weight precisely because they’re out of character. For the narrator, it’s less encouragement than a coded demand to align physically with the company’s ambitions.

Midnight Moves

After committing to the move, Mark’s follow-up email—sent at 1:39 AM—epitomizes his relentless work ethic. Its brevity and timing contrast with its gracious tone, a duality that surprises the narrator. The timestamp becomes a metaphor for the round-the-clock dedication expected in Silicon Valley, where personal boundaries blur into mission-driven urgency.

Key Takeaways

• Power Shifts West: Silicon Valley’s emergence as a geopolitical hub forces physical relocation for those shaping policy.
• Mark’s Indirect Authority: Zuckerberg’s communication style—terse, strategic, and rarely effusive—leverages implication over direct orders.
• The Cost of Influence: Professional demands increasingly dictate personal life, as seen in the narrator’s reluctant uprooting from New York.
• Symbols in Silence: Even minor details (e.g., email timestamps) reveal cultural norms within tech leadership.

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25. Muppets and Monsignors

Overview

September 2015 marks a pivotal week for Mark Zuckerberg as he navigates high-stakes diplomatic efforts with China, promotes Internet.org at the United Nations, and grapples with a chaotic appearance at the Global Citizen Festival. Each event underscores Facebook’s ambitions—and missteps—as it seeks global influence. From awkward political maneuvers to impulsive announcements, the chapter reveals the tension between idealism and the realities of wielding corporate power on the world stage.

China’s Diplomatic Dance

Facebook’s long-shot bid to enter China hinges on Chinese President Xi Jinping’s U.S. visit. Despite months of lobbying, Xi opts to start his trip in Seattle, sidelining Facebook. Desperate for recognition, Mark flies to Seattle for a brief, staged handshake with Xi at Microsoft’s campus. The interaction lasts less than a minute, and Mark’s subsequent Facebook post—featuring a photo of Xi’s back—sparks outrage from Chinese officials mid-flight, creating a diplomatic crisis. The team debates removing the photo but leaves it up, fearing backlash. Later, at a White House state dinner, Mark’s attempt to ask Xi to name his unborn child in Mandarin is swiftly rejected. The episode highlights Facebook’s clumsy foray into geopolitics and its struggle to balance ambition with cultural sensitivity.

The UN Speech and a Phantom Promise

At the United Nations, Mark champions Internet.org’s “Connectivity Declaration,” a $1 million campaign advocating universal internet access by 2020. While the initiative garners celebrity endorsements and positive press, Mark stuns his team by unilaterally pledging to provide Wi-Fi to refugee camps—a promise never discussed internally. Policy head Elliot and Internet.org lead Chris Daniels scramble to address the announcement, only to discover no plan exists. Worse, internal discussions later reveal plans to charge refugees for access, raising ethical questions. The disconnect between Mark’s grand pronouncements and operational reality begins to erode team morale.

Central Park Chaos and the Big Bird Debacle

The Global Citizen Festival in New York devolves into farce as Mark’s team clashes over scheduling. A last-minute request to meet the pope is denied, while tensions flare over Mark’s slot following Big Bird. After frantic negotiations, Mark is scheduled after Bill Nye—only for a pre-recorded video to accidentally play during his live speech, leaving him frozen onstage. The cringe-worthy moment underscores the pitfalls of prioritizing optics over preparation. Despite the humiliation, Mark comforts the author, displaying uncharacteristic empathy. Yet the mishap amplifies doubts about his readiness for the global spotlight.

Cracks in the Mission

In the aftermath, Mark’s team confronts the fallout from his refugee-camp pledge. A proposed Facebook post featuring a “white savior” photo of an engineer with Tanzanian refugees is criticized for tone-deafness. As internal emails reveal the lack of planning behind Mark’s UN announcement, the author grapples with disillusionment. She realizes that exposing Mark to global leaders has not fostered accountability but instead enabled impulsive, image-driven decisions. The chapter closes with her dawning awareness of the gap between Facebook’s utopian rhetoric and its ad-hoc execution—a disconnect that foreshadows larger crises.

Key Takeaways

• Diplomatic Overreach: Facebook’s rushed attempts to court China reveal a naiveté about geopolitical nuance, culminating in a protocol breach that damages relations.
• The Cost of Grandstanding: Mark’s unilateral UN announcement about refugee camps—and the lack of follow-through—exposes a pattern of prioritizing PR over substance.
• Optics vs. Ethics: The team’s scramble to manage Mark’s impulsive decisions highlights the tension between Facebook’s idealism and its often-cynical operational choices.
• Leadership Disconnect: The author’s growing realization that Mark’s exposure to global power has not instilled responsibility but amplified a tendency toward performative, poorly planned gestures.

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26. The Wicked Witch of the West

Overview

The chapter delves into the escalating conflict between Facebook’s Internet.org initiative and global digital rights advocates. What begins as a clash over net neutrality and user access evolves into a revealing internal battle over Facebook’s ethics, branding, and leadership dynamics. As tensions mount, the chapter exposes the gap between the project’s lofty rhetoric and its flawed execution, while highlighting the personal and ideological struggles within Facebook’s ranks.

The Backlash Against Internet.org

Sixty-seven digital rights groups worldwide unite to condemn Internet.org, arguing it violates net neutrality by offering a curated, Facebook-approved slice of the internet rather than full access. Critics accuse the platform of enabling censorship, exposing users to unmoderated hate speech, terrorism content, and fraud due to lax security protocols. The absence of encryption and two-factor authentication disproportionately harms marginalized communities, deepening the digital divide. For these groups, Internet.org isn’t a philanthropic endeavor but a cynical ploy to expand Facebook’s user base under the guise of altruism.

A Fractious Showdown

A videoconference between Facebook’s Chris Daniels and digital rights representatives turns explosive. Daniels, defensive and angry, likens Internet.org’s gatekeeping to app stores like Apple’s or Google’s—a comparison critics reject as disingenuous. The meeting’s absurd backdrop—a room named “Wicked Witch of the West”—underscores the disconnect between Facebook’s self-image and its critics’ perception. The author leaves convinced Facebook is morally compromised, using “saving the world” narratives to mask self-interest.

Internal Rebellion and Branding Wars

The author challenges Facebook’s leadership to drop the facade of altruism, advocating for honesty about Internet.org’s profit-driven motives. Elliot Schrage, a top executive, rebuffs this, insisting Mark Zuckerberg views the project as both growth strategy and philanthropy. Meanwhile, Brazil’s government bans the “Internet.org” name for being misleading, forcing a rebranding debate. Zuckerberg resists, framing concessions as failures, but after weeks of tense negotiations—and the author’s solitary advocacy—the platform reluctantly adopts “Free Basics” as a global rebrand.

Power, Ego, and Compromise

The final rebranding showdown reveals Zuckerberg’s combative leadership style. In a heated meeting, he rails against compromise, insisting on total victory. The author, isolated as the sole dissenter (and only woman) in the room, pushes strategic concessions to salvage the project’s viability. Zuckerberg begrudgingly agrees to rename the service in Brazil, eventually extending the “Free Basics” rebrand globally—a small victory overshadowed by the broader ethical compromises.

Key Takeaways

• Net Neutrality vs. Corporate Control: Internet.org’s restricted access model sparked global backlash for undermining open internet principles.
• Security Failures: The platform’s lack of encryption and moderation exposed vulnerable users to exploitation.
• Branding as Battleground: The shift from “Internet.org” to “Free Basics” highlighted Facebook’s struggle to balance growth with credibility.
• Leadership Under Fire: Zuckerberg’s resistance to criticism and insistence on total control underscored a culture prioritizing expansion over accountability.
• The Cost of “Philanthropy”: The chapter frames Internet.org as a case study in corporate overreach, where purported altruism masks market capture.

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27. Street Fighter Tactics

Overview

The chapter explores Facebook’s aggressive campaign to push its Free Basics program in India, a project aimed at providing limited internet access to underserved populations. Facing intense regulatory scrutiny and public backlash, internal tensions rise as Mark Zuckerberg advocates for adopting ruthless "street fighter tactics" inspired by Uber’s confrontational strategies. What begins as a clash over net neutrality escalates into a high-stakes battle involving propaganda, technical manipulation, and political pressure—culminating in a humiliating defeat for Facebook and the collapse of its broader Internet.org initiatives.

Internal Strategy Shift

Mark Zuckerberg convenes a critical meeting with senior leaders, urging them to abandon Facebook’s traditionally diplomatic approach. He praises Uber’s underhanded tactics—such as orchestrating protests, bribing officials through sponsorships, and targeting journalists—and demands similar ruthlessness. Drawing parallels to Emperor Augustus, he insists on mobilizing Facebook’s user base as a political weapon, compiling “adversary lists,” and leveraging the platform’s algorithm to pressure opponents. The author, disillusioned by the shift toward hostility, decides to resist internally while outwardly complying.

Public Manipulation Tactics

Facebook launches a massive propaganda blitz in India, spending tens of millions on TV ads, billboards, and targeted "dark posts." A viral campaign prompts users to send prewritten emails to regulators supporting Free Basics, with notifications tricking users into broadcasting their participation to friends. Protests are allegedly organized by offering free T-shirts, while the platform floods the Telecom Regulatory Authority of India (TRAI) with 16.9 million duplicate form emails. However, the campaign’s credibility unravels as critics accuse Facebook of exploiting its platform to hijack democratic processes.

Technical Failure and Backlash

A critical flaw emerges: TRAI’s email system opts out of receiving Facebook’s automated submissions, leaving only 1.4 million emails counted—a fraction of the intended total. Despite last-ditch efforts to submit the remaining 17 million comments via flash drive, regulators reject the campaign as manipulative. TRAI’s final ruling bans Free Basics outright, citing violations of net neutrality principles. The decision stuns Facebook’s leadership, with one executive noting the irony of being outmaneuvered by a “low-ranking official” who clicked an opt-out button.

Aftermath and Project Collapse

The Free Basics defeat triggers a domino effect. Facebook’s drone project, Aquila, crashes during testing due to reckless decision-making pressured by Zuckerberg’s presence. A satellite partnership with SpaceX explodes on launch, further dooming Internet.org’s ambitions. While Free Basics limps into smaller markets like Myanmar (with disastrous consequences later revealed), Zuckerberg and senior leaders abandon the initiative, leaving teams demoralized and the company’s ethical reputation in tatters.

Key Takeaways

1. Aggressive Tactics Backfire: Facebook’s shift to coercive methods alienated regulators, the public, and internal staff, proving counterproductive.
2. Regulatory Resistance: TRAI’s firm stance highlighted global pushback against tech giants undermining democratic processes and net neutrality.
3. Ethical Erosion: Zuckerberg’s embrace of “street fighter” strategies revealed a departure from Facebook’s purported idealism, prioritizing expansion over principles.
4. Internal Dissent: The author’s moral conflict underscores the human cost of corporate overreach, as employees grapple with unethical mandates.
5. Technical Arrogance: Overreliance on engineering solutions failed to account for institutional scrutiny, exposing fatal flaws in Facebook’s approach.

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28. Lean In and Lie Back

Overview

This section delves into the escalating tensions and power dynamics within Sheryl Sandberg’s inner circle at Facebook, particularly during the lead-up to and fallout from the 2016 Davos summit. It highlights the blurred lines between professional loyalty and personal boundaries, the ethical compromises tied to Facebook’s political influence, and the toll of Sheryl’s demanding leadership style on her team—especially on the narrator, who navigates these challenges while in the final weeks of her pregnancy.

Sheryl’s Inner Circle: Ambition and Enmeshment

Sheryl’s reliance on young, ambitious hires like Sadie—a charismatic Ivy League graduate—reveals a culture where proximity to power comes at a cost. These “hybrid” assistants wield significant influence, blurring roles between professional advisors and personal confidants. Sadie’s loyalty to Sheryl is rewarded with perks like designer clothes, board seats, and access to Sheryl’s vacation homes, but it also demands compliance with intrusive requests, such as purchasing thousands of dollars in lingerie for Sheryl and herself. The relationship oscillates between mentorship and manipulation, epitomized by Sadie’s self-described role as Sheryl’s “little doll.”

Davos and Political Leverage

At Davos, Facebook’s leadership capitalizes on global anxieties about terrorism to deflect scrutiny over privacy concerns. Sheryl openly celebrates how fear of terrorism has shifted policymakers’ focus toward surveillance—a boon for Facebook’s business model. Meetings with figures like David Cameron and George Osborne underscore Facebook’s growing political clout: rather than facing regulatory pressure, politicians now request Facebook’s support for campaigns like anti-Brexit efforts. These interactions signal a seismic shift in power dynamics, with governments seeking favors from the platform rather than holding it accountable.

The Breaking Point: Boundaries and Consequences

The narrator’s refusal to share a bed with Sheryl during the return flight from Davos becomes a pivotal moment. Sheryl’s insistence—framed as a demand for obedience—exposes the toxic expectation of total personal allegiance. The narrator’s pregnancy amplifies the strain, as medical concerns about travel are dismissed by Sheryl’s team. After the confrontation, Sheryl’s icy retaliation (“You should have got into bed”) and the leadership’s refusal to address the incident (Joel and Elliot advise silence) leave the narrator isolated. Colleagues like Debbie downplay the situation, normalizing invasive behavior as part of the job.

The Cost of Compliance

Sadie’s internal conflict mirrors the narrator’s: while she enjoys the privileges of Sheryl’s favor, she privately acknowledges the stress of their enmeshed relationship. The chapter underscores how Sheryl’s “lean in” ethos—celebrated publicly through initiatives like her Lean In Foundation—clashes with the private reality of subordinates “lying back” to accommodate her demands. The narrator’s resolve to leave intensifies, but financial and professional constraints (proximity to childbirth, Sheryl’s control over policy roles) leave her trapped—for now.

Key Takeaways

• Power Dynamics: Sheryl’s inner circle operates on a transactional exchange of loyalty for access, creating a culture of compliance that erodes personal boundaries.
• Political Manipulation: Facebook leverages crises like terrorism to advance its business interests, while politicians increasingly seek its influence over public opinion.
• Toxic Loyalty: The expectation of unquestioning obedience to leadership fosters a workplace where ethical concerns and personal well-being are secondary to maintaining favor.
• Structural Vulnerability: Employees, particularly women, face impossible choices between career advancement and self-respect, exacerbated by hierarchical power structures.

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29. Citizen Sanchez

Overview

The chapter captures a pivotal moment in the narrator’s pursuit of American citizenship, juxtaposing the bureaucratic grind of immigration processes with the unsettling dynamics of their professional life. Amid mounting pressure to secure citizenship before their spouse’s visa expires, the narrator navigates a dehumanizing government office, an ill-prepared legal team, and a supervisor whose inappropriate remarks escalate in brazenness. The stakes are high: failure could uproot their life in the U.S., yet the path to success is riddled with institutional oversights and personal indignities.

The Citizenship Test: Aspirations vs. Reality

The narrator arrives at a grim San Francisco immigration office, a far cry from the “American dream” they’re striving to formalize. Despite studying foundational U.S. documents and ideals, the test begins disastrously: they blank on their own wedding date, a humiliating misstep that sets a tense tone. Though they recover to answer subsequent questions correctly, the process feels emblematic of a system that reduces personal milestones to cold bureaucracy.

Joel’s “Dirty Sanchez” and Workplace Toxicity

As anxiety about the test peaks, Joel—a superior at Facebook—sends a crass email referencing a vulgar slang term (“Dirty Sanchez”), exploiting the narrator’s vulnerability. This follows a pattern of inappropriate behavior: sexualized jokes, power-laden comments about being a “sugar daddy,” and demeaning remarks disguised as humor. The timing amplifies the narrator’s stress, highlighting how workplace toxicity compounds personal crises.

The Residency Snafu: A System Set Up to Fail

After passing the test, a bureaucratic bombshell drops: California’s 90-day residency requirement hasn’t been met due to a 17-day shortfall—a critical oversight by Facebook’s legal team. The narrator now faces restarting the entire process, with their spouse’s expiring visa adding urgency. The reliance on corporate lawyers to expedite the case underscores their precarious position: citizenship hinges on institutional competence, not merit.

Key Takeaways

• Bureaucratic fragility: Even with corporate resources, immigration processes are fraught with opaque rules and systemic inefficiencies.
• Power imbalances: Workplace harassment often escalates in moments of personal vulnerability, exploiting power dynamics.
• The “dream” disconnect: The gap between America’s aspirational ideals and its bureaucratic realities creates emotional and logistical tolls.
• Trapped by circumstance: Financial and legal dependencies (e.g., visas, corporate legal teams) can force individuals to endure toxic environments.

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30. Poker Face

Overview

February 2016 marks a pivotal moment for Facebook as global leaders confront Joel, Sheryl, and the narrator in Davos over the platform’s role in terrorism radicalization, hate speech, and lack of government collaboration. With Internet.org collapsing under regulatory pressure and governments eyeing new ways to tax or restrict Facebook, internal urgency grows. The leadership team agrees the board must grasp the existential threat of regulation—a force capable of derailing Facebook’s growth overnight. The narrator advocates for mature dialogue with governments but faces resistance from colleagues favoring hardball tactics. A $55 million budget and 60 new policy staff are proposed to address the crisis, setting the stage for a high-stakes board meeting that reveals deeper cracks in Facebook’s approach to power and ethics.

Global Backlash and Internal Alarm

Weeks after Davos, Facebook’s leadership grapples with escalating government distrust. Politicians worldwide view the platform as a threat to local industries, privacy, and societal stability, with tools like antitrust and privacy laws poised to dismantle its global dominance. Internet.org’s failure underscores how quickly governments can upend Facebook’s plans. Internally, Joel, Sheryl, and Elliot push to shock the board into action, framing regulation as an imminent business risk. The narrator clings to hopes of transparent government partnerships but acknowledges the team’s preference for aggressive negotiation.

The Boardroom Dynamics

The board meeting defies expectations: a casual, tech-campus vibe replaces corporate formality. Sheryl sits cross-legged in yoga pants, Mark Zuckerberg scrolls his phone, and board members like Peter Thiel and Reed Hastings adopt roles ranging from provocateur to detached observer. Despite the laid-back atmosphere, power dynamics are clear—Mark’s dual-class shares render him unchallenged. The team presents their case for policy investment, emphasizing global regulatory threats. The board’s response focuses on transactional “deals” to appease regulators, diverging from the narrator’s vision of principled collaboration.

Ethical Crossroads and Unspoken Analogies

When the board seeks parallels for Facebook’s crisis, Elliot compares the company to Big Tobacco—a jarring analogy that halts discussion. The conversation shifts to leveraging Facebook’s election tools to align with Europe’s far-right parties, seen as a shortcut to regulatory relief. The narrator’s visible disgust at this strategy (including eye-rolling) later becomes a focal point in their performance review, exposing tensions between ethical boundaries and corporate pragmatism.

The Poker Face Critique

Joel praises the narrator’s strategic calm in high-pressure scenarios but chastises their lack of restraint during the board meeting. The critique centers on reactions to proposals about courting far-right European politicians like Marine Le Pen—a tactic deemed politically expedient but morally fraught. The narrator’s unguarded moments highlight a cultural divide: Facebook’s leadership prioritizes survival, while dissenters grapple with the human cost of such alliances.

Key Takeaways

• Facebook’s growth-first mindset clashes with global governments’ rising regulatory and ethical concerns.
• The board’s casual authority and transactional approach underscore Mark’s unchecked control.
• Internal debates reveal stark divides: negotiate with power (even extremists) versus principled collaboration.
• The tobacco analogy and far-right strategy crystallize Facebook’s existential crisis: profit vs. public trust.

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31. A Heartwarming Story

Overview

The chapter recounts a pivotal moment in 2016 when Diego Dzodan, a Facebook executive in Brazil, was arrested due to WhatsApp’s refusal to comply with a court order to share encrypted messages tied to a drug trafficking case. The incident exposes internal tensions at Facebook, particularly Mark Zuckerberg’s prioritization of public messaging over employee welfare, and catalyzes the author’s growing disillusionment with the company’s leadership.

The Arrest and Legal Fallout

Diego’s arrest stems from a Brazilian judge’s insistence that Facebook and WhatsApp are functionally the same entity—a claim bolstered by Mark’s past public statements. Despite Facebook’s legal team arguing the companies are separate, the judge cites Mark’s earlier call for Brazilians to protest WhatsApp’s temporary shutdown as evidence of their alignment. Diego, who had no direct involvement with WhatsApp, becomes collateral damage in a battle over encryption and corporate accountability.

Mark’s PR Obsession

Mark views Diego’s arrest as a storytelling opportunity, drafting a self-congratulatory post framing the incident as a heroic stand for user privacy. The draft emphasizes Diego’s loyalty (“Count on me!”) and positions Facebook as a defender of safety, despite the messages in question involving a drug cartel threatening a judge’s life. Colleagues, including legal advisors, warn that the post would undermine Diego’s defense and inflame Brazilian authorities, but Mark remains fixated on spinning a “heartwarming” narrative.

Internal Pushback and Risks

Facebook’s general counsel and policy team urge Mark to reconsider, stressing that publicly conflating Facebook and WhatsApp would sabotage their legal strategy. They warn that the post could endanger Diego further and normalize arrests of employees in Brazil. Meanwhile, the author highlights Mark’s absence of meaningful action—such as leveraging political connections—to secure Diego’s release, contrasting it with their own efforts to pressure Brazilian officials behind the scenes.

Diego’s Release and Aftermath

After less than a day in jail, Diego is released following an appeals court ruling. While the immediate crisis resolves, the author grapples with Mark’s indifference to Diego’s plight. The episode shatters their faith in Facebook’s leadership, revealing a pattern of prioritizing growth and optics over ethical responsibility.

Personal Reckoning

The author realizes their hope for Mark to evolve into a responsible leader was misplaced. Mark’s actions—or lack thereof—during Diego’s arrest symbolize a broader failure to weigh human costs against corporate ambitions. This disillusionment, compounded by the author’s pregnancy and logistical constraints, solidifies their decision to leave Facebook, despite uncertainties about their next steps.

Key Takeaways

• Corporate vs. Human Priorities: Mark’s focus on crafting a “heartwarming” narrative over Diego’s safety underscores a disconnect between Facebook’s public ideals and its internal values.
• Legal Naivety: Attempts to weaponize encryption as a PR tool backfire, exposing Facebook’s poor grasp of geopolitical and legal realities.
• Leadership Accountability: The incident reveals a toxic culture where employees are expendable in service of growth and image control.
• Breaking Point: For the author, Diego’s arrest becomes the final straw in a series of ethical compromises, forcing a reckoning with Facebook’s moral bankruptcy.

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Careless People Summary

32. What to Not Expect When You’re Expecting

Overview

The chapter recounts a harrowing journey through pregnancy, childbirth, and near-fatal complications, set against the backdrop of growing concerns about the Zika virus and the isolating pressures of corporate life. What begins as a quiet reflection on a work-related trip to Brazil spirals into a visceral exploration of maternal fear, systemic healthcare failures, and the fragility of life.

The Shadow of Zika

A casual read of a New York Times article about Zika virus outbreaks in Brazil triggers a panic when the narrator realizes she traveled to the epicenter of the crisis—Jodo Pessoa—during her pregnancy. Haunted by graphic descriptions of babies with microcephaly, she obsessively researches the risks, confronting guilt over unknowingly endangering her child. Her doctor dismisses her concerns but orders an ultrasound, which offers little reassurance. The medical team admits they lack clear diagnostic criteria for Zika in utero, leaving her in limbo.

Birth and Breakdown

Months later, the narrator delivers a healthy baby girl, Xanthe, but the relief is short-lived. Moments after birth, she begins shaking uncontrollably, dismissed as exhaustion until nurse Lauren notices alarming blood loss. The situation escalates rapidly: swelling, convulsions, and a near-fatal amniotic fluid embolism plunge her into emergency surgery. As doctors fight to save her life, she battles to stay conscious, terrified of leaving her newborn and husband behind.

Life Support and Isolation

Waking in an ICU, intubated and restrained, the narrator grapples with disorientation and terror. Unable to speak, she scribbles frantic questions about her baby’s safety. Tom reveals Xanthe is healthy but discloses he named their daughter without her input—a moment layered with grief and resignation. Medical staff later explain she survived over 35 transfusions after her blood stopped clotting, a stark reminder of how close she came to death.

A Fragile Recovery

Discharged but physically shattered, the narrator faces the reality of caring for a newborn and toddler while recovering from near-fatal hemorrhaging. Back home, she hides worsening symptoms from Tom to avoid further burdening him. The trauma crystallizes her resolve to leave Facebook, but physical debilitation and maternal guilt stall action. The chapter closes on a haunting note: maternal mortality in the U.S. is rising, a “modern American way to die” juxtaposed against her high-tech Silicon Valley life.

Key Takeaways

• Maternal vulnerability: Pregnancy complications like amniotic fluid embolisms remain poorly understood and lethal, exacerbated by systemic gaps in U.S. healthcare.
• Silent suffering: The pressure to minimize pain—whether from dismissive doctors or self-imposed stoicism—perpetuates isolation during crises.
• Corporate vs. caregiving: High-stakes tech careers often clash with the raw, bodily demands of parenthood, forcing impossible choices.
• Guilt and survival: Trauma reshapes identity, leaving lasting scars even when physical recovery seems possible.

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33. Do We Have to Go into This?

Overview

This chapter captures a period of intense personal vulnerability and professional friction as the narrator navigates postpartum health crises, workplace pressures, and ethical dilemmas at Facebook. Struggling with prolonged medical complications after childbirth, she faces relentless demands from her boss, Joel, whose behavior escalates from inappropriate to coercive. Meanwhile, her attempts to raise alarms about political manipulation on Facebook’s platform are met with indifference from leadership, highlighting a growing disconnect between the company’s profit motives and its societal responsibilities.

Health Struggles and Workplace Tensions

The narrator’s physical recovery is marred by severe blood loss, fatigue, and unresolved medical issues. Despite being on maternity leave, Joel and his assistant bombard her with work demands, including mandatory video calls where Joel’s unprofessional conduct—lying in bed during meetings and probing invasively about her health—crosses boundaries. His insistence on discussing her bleeding and breastfeeding becomes a power play, weaponizing discomfort to assert control.

The Hyderabad Offsite

Joel pressures the narrator to attend a leadership retreat in India shortly after her return to work, ignoring her medical team’s advice and her fears of hemorrhaging during the grueling 20-hour flight. When she raises concerns about breastfeeding and health risks, Joel feigns ignorance, demanding she “explain breastfeeding” to him. The company’s “solution” involves sending a breast pump and assigning HR representative Stacey Tomey to accompany her—a gesture that underscores their dismissal of her legitimate fears.

Performance Review and Systemic Indifference

On her first day back, Joel conducts a retaliatory performance review, criticizing her for being “unresponsive” during maternity leave—a period that included a medically induced coma. HR’s complicity becomes clear when Stacey admits awareness of the unreasonable workload imposed during her leave. The narrator’s attempts to seek support are met with hollow assurances, reflecting a culture that prioritizes productivity over employee well-being.

Political Misinformation and Corporate Complicity

At the Hyderabad strategy meeting, the narrator highlights how authoritarian regimes like Duterte’s in the Philippines exploit Facebook’s algorithms to spread disinformation and consolidate power. She connects this to broader risks, including the upcoming U.S. election, but is met with blank stares and dismissal. Joel and leadership openly prioritize profit over integrity, celebrating ad revenue from inflammatory campaigns like Trump’s while downplaying Facebook’s role in democratic erosion. The chapter underscores Facebook’s incentivization of outrage-driven content and its refusal to reckon with the consequences.

Key Takeaways

• Power Dynamics: Joel’s manipulation and HR’s complicity reveal systemic workplace toxicity, where vulnerability is exploited and boundaries ignored.
• Ethical Erosion: Facebook’s leadership prioritizes profit and political ad revenue over addressing platform misuse, enabling authoritarian regimes and misinformation.
• Personal vs. Professional Conflict: The narrator’s physical and emotional strain mirrors the broader tension between corporate ambition and human cost, both individually and societally.

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Careless People Summary

34. The Facebook Election

Overview

The chapter captures the tense, emotionally charged atmosphere at Facebook headquarters in the wake of Donald Trump’s 2016 election victory. A company-wide meeting reveals stark ideological divides between Republican leaders like Joel Kaplan (VP of Global Public Policy) and distraught Democratic employees. The gathering underscores Facebook’s struggle to reconcile its self-image as a neutral platform with its growing influence over politics, while internal tensions over race, immigration, and corporate responsibility simmer beneath the surface.

Ideological Fault Lines

Joel Kaplan’s visible satisfaction with Trump’s win contrasts sharply with the grief and fear expressed by many employees. He dismisses concerns about Trump’s rhetoric or policies, framing the election as a victory for Republican priorities like tax cuts and deregulation. His focus on policy gains—while sidelining ethical questions—highlights a disconnect between leadership’s priorities and the anxieties of rank-and-file staff. Kaplan openly admits disappointment that Trump might not cut entitlement programs like Social Security, revealing a hardline fiscal conservatism that prioritizes ideology over broader societal impacts.

A Room Divided

The meeting exposes raw emotions: a young employee voices fears for Black and Hispanic friends, while others reference internal tensions like “All Lives Matter” graffiti and pro-Trump posters appearing on campus. A white employee’s awkward attempt to “be an ally” draws silent discomfort, particularly as the overwhelmingly white, male DC policy team—projected on the wall—reacts with visible disdain. The lack of diversity in the room becomes glaring, underscoring Facebook’s homogeneity and its failure to address systemic inequities within its own walls.

The Elephant in the Room

When an employee directly asks if Facebook’s role in the election contributed to Trump’s victory, Elliot Schrage (VP of Communications and Public Policy) deflects, insisting Facebook’s mission is simply to “make the world more open and connected.” This dismissal mirrors Mark Zuckerberg’s later public denial that fake news on the platform swayed voters. The exchange lays bare leadership’s refusal to reckon with the company’s power—or the ethical implications of monetizing political polarization through targeted ads.

Key Takeaways

• Leadership’s ideological blinders: Republican executives like Joel Kaplan celebrated Trump’s agenda, dismissing employee concerns about marginalized communities as secondary to fiscal policy wins.
• A culture of avoidance: Facebook’s leadership deflected accountability for the platform’s political impact, hiding behind platitudes about connectivity while ignoring internal and external critiques.
• Diversity as an afterthought: The lack of racial and gender diversity in key teams exacerbated tensions, leaving minority employees feeling unheard and unprotected.
• The myth of neutrality: Despite branding itself as apolitical, Facebook’s internal rhetoric and ad-driven business model revealed deep entanglement with partisan agendas.

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Careless People Summary

35. Angry at the Truth

Overview

The chapter unfolds against a backdrop of escalating tensions, revealing Mark Zuckerberg’s growing isolation from the consequences of his decisions. A chaotic airport scene sets the tone: forgotten passports, misplaced medication, and staffers scrambling to shield him from accountability. This personal disarray mirrors Facebook’s institutional chaos, as Zika-fueled paranoia drives absurd extremes like “Operation Perfect Sperm”—a blend of sealed rooms and bug suits designed to protect Mark’s family plans while exposing his obsession with control.

Mid-flight, a reckoning brews. Elliot Schrage confronts Mark with irrefutable evidence of Facebook’s role in Trump’s election, detailing microtargeted ads and voter suppression tactics. Mark’s fascination with the campaign’s “ingenuity” clashes with his team’s unease, underscoring a rift between ethical concerns and corporate opportunism. This tension spills into crafting a post-election response, where Mark’s vague pledges to “explore solutions” betray a refusal to admit systemic failures. His defensive timestamping of statements—“I posted this at 9:30pm…”—reveals a leader more attuned to optics than impact.

Geopolitical ambitions unravel in Peru. A botched attempt to engineer a “chance” meeting with Xi Jinping—thwarted by Chinese security—exposes Mark’s naivety about global power structures. Meanwhile, a sycophantic roundtable with world leaders underscores their reliance on Facebook’s influence, as figures like Rodrigo Duterte nap through hollow discussions. Even Diego Dzodan, who sacrificed freedom for Facebook in Brazil, becomes a disposable pawn, dismissed in seconds by a CEO who barely recognizes his name.

The chapter crescendos with Barack Obama’s blistering critique, accusing Facebook of destabilizing democracies. Mark’s furious deflection—labeling Obama a “lame duck”—lays bare his hypersensitivity to criticism and inability to reconcile Facebook’s power with its societal toll. Through failed statesmanship, transactional loyalty, and ethical blind spots, the narrative paints a portrait of a leader—and a company—trapped in a self-constructed bubble, where accountability is outsourced, consequences are deflected, and unchecked influence thrives unchallenged.

The Airport Incident and Passport Debacle

Mark Zuckerberg’s frustration simmers as the Facebook team scrambles at the airport before departing for the APEC summit in Peru. His anger—directed at accusations of Facebook’s role in Trump’s election, logistical mishaps, and forgotten passport—reveals his detachment from accountability. Staffers deflect blame, with Andrea taking responsibility for the passport oversight. The absurdity peaks when Elliot suggests asking Peru’s president to waive entry requirements for Mark. The delay worsens when Mark realizes he’s missing medication, forcing the team to postpone the flight.

Zika Concerns and "Operation Perfect Sperm"

Months earlier, Mark’s team grappled with his fear of Zika exposure jeopardizing plans to expand his family. Elliot’s whispered call to the narrator about ovulation timing and Zika mitigation spirals into extreme measures: sealed conference rooms, a custom-built Facebook-controlled structure in Peru, and even a head-to-toe “bug suit” proposal. The narrator navigates awkward negotiations with Peruvian officials to accommodate Mark’s demands, culminating in a lavish Facebook pop-up venue at APEC—a physical manifestation of Mark’s insulated world.

Inflight Reckoning: Facebook’s Role in Trump’s Victory

During the flight, Elliot confronts Mark with a damning breakdown of Facebook’s inadvertent role in Trump’s election. Embedded staff, microtargeted ads, voter suppression tactics, and Trump’s data-driven “Project Alamo” are laid bare. Mark shifts from skepticism to fascination, admiring the campaign’s ingenuity. The narrator recoils at the ethical implications, recalling Sheryl Sandberg’s earlier interest in recruiting Trump’s digital strategist, Brad Parscale. Elliot pushes Mark to publicly acknowledge Facebook’s impact, but Mark resists, framing criticism as media retaliation for disrupting traditional news revenue.

Crafting the Post-Election Response

A tense drafting session unfolds mid-flight as Elliot urges Mark to commit to concrete reforms. Mark’s eventual post—a vague pledge to combat misinformation—reflects his reluctance. Key concessions, like partnering with fact-checkers, are watered down to “exploring” solutions. The post deflects blame, framing Facebook’s actions as incremental progress rather than systemic failure. Mark’s defensive timestamp explanation (“I posted this at 9:30pm…”) underscores his inability to grasp the gravity of the moment.

The Xi Jinping Encounter That Wasn’t

The narrator orchestrates a backstage “spontaneous” meeting between Mark and China’s President Xi by securing adjacent dressing rooms at APEC. Xi’s security detail thwarts the plan with a militaristic human wall, leaving Mark visibly stung. The failed encounter highlights Mark’s naivety about geopolitical power dynamics and China’s deliberate avoidance of Facebook’s influence. Despite the setback, Mark proceeds to host a meeting with other heads of state, though his earlier curiosity about global governance has faded into disengagement.

Key Takeaways

• Mark’s insulated worldview and refusal to accept responsibility—for both personal oversights and Facebook’s societal impact—reveal a leader disconnected from consequences.
• Facebook’s tools enabled Trump’s campaign to exploit data-driven microtargeting and voter suppression, yet internal reactions ranged from horror to admiration.
• Attempts to position Mark as a global statesman falter, exemplified by Xi’s deliberate snub and Mark’s tone-deaf response to election interference criticism.
• The APEC trip underscores Facebook’s unchecked power and the ethical vacuum in its leadership, as symbolic gestures replace meaningful reform.

A Disposable Asset

Diego Dzodan’s encounter with Mark Zuckerberg underscores the disconnect between Facebook’s leadership and its most loyal employees. Despite Dzodan’s sacrifice—jailing himself in Brazil for the company—Mark initially fails to recognize him, requiring a reminder of Dzodan’s identity. The interaction is cold and transactional, with Mark offering a robotic thanks before pivoting to more pressing crises, like navigating Ivanka Trump’s awkward involvement in the Breakthrough Prize ceremony. Dzodan fades into the background, symbolizing how even high-stakes loyalty is easily overshadowed by the platform’s relentless political and public relations machinery.

Power Dynamics in the Grand Hall

The roundtable with global leaders devolves into a display of sycophancy rather than accountability. Presidents and prime ministers—including Justin Trudeau, Enrique Peña Nieto, and Michelle Bachelet—avoid confronting Mark about Facebook’s role in misinformation, election interference, or tax evasion. Instead, they lob soft questions about replicating Facebook’s success or leveraging connectivity for governance. Rodrigo Duterte, a Facebook-boosted leader, naps through the session. The leaders’ reluctance to challenge Mark reveals their dependence on Facebook as a political tool, prioritizing access to its influence over holding it accountable.

The Obama Reckoning

Mark’s meeting with Barack Obama erupts into conflict, exposing his hypersensitivity to criticism. Obama directly blames Facebook for amplifying fake news and destabilizing democracies, urging Mark to address these threats. Mark dismisses the feedback, framing Obama as a “lame duck” and downplaying Facebook’s impact. His fury—replaying Obama’s critiques “as if trying to beat them into submission”—highlights his inability to reconcile Facebook’s power with its societal consequences. The clash leaves Mark visibly wounded, revealing his thin skin and isolation from meaningful accountability.

Key Takeaways

• Hierarchy of Loyalty: Even employees who risk everything for Facebook are expendable in the face of Mark’s shifting priorities.
• Leaders in Fear: Global politicians avoid confronting Facebook’s harms, prioritizing their own electoral survival over accountability.
• Criticism as Kryptonite: Mark’s defensive reaction to Obama underscores his inability to engage with critiques from peers he respects, signaling a dangerous detachment from reality.
• Shifting Power: As world leaders court Mark, his indifference grows, reflecting Facebook’s unchecked influence in shaping political landscapes.

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Careless People Summary

36. Rosebud

Overview

The chapter captures a pivotal moment during a tense flight where Mark’s competitive nature, obsession with legacy, and political ambitions collide. After losing repeatedly to the narrator in board games, Mark’s refusal to accept defeat sparks a broader confrontation about his leadership style. This sets the stage for revelations about his plans to reshape media, run for president, and cement his legacy—all while the narrator grapples with disillusionment over his escalating ambitions.

Board Games and Blowups

Mark’s frustration boils over after losing multiple rounds of Ticket to Ride and Settlers of Catan to the narrator, whom he accuses of cheating. Their argument evolves into a critique of Mark’s “win-at-all-costs” mentality. The narrator points out how his obsession with short-term victories (like clinging to the “Internet.org” branding despite regulatory backlash) undermines long-term goals. Mark begrudgingly concedes the point but shifts focus to his fixation on legacy.

Legacy, Speeches, and Presidential Aspirations

Mark’s preoccupation with his Harvard commencement speech and annual “personal challenges” reveals his desire to be remembered for more than Facebook. His 2017 challenge—visiting early presidential primary states like Iowa and New Hampshire—alarms the narrator. The team scrambles to plan logistics, but no one challenges Mark directly, even as he openly mimics campaign-trail optics (farm visits, church meetups, rodeos). The narrator confronts Elliot, who dismisses her concerns, signaling the team’s reluctance to push back.

Remaking Media (and Reality)

Mark outlines plans to dominate the news industry: either buying the New York Times or creating a “fifth estate” controlled by Facebook. He dismisses partnerships with traditional media as “compromising with a dying industry.” The narrator recognizes this as a power grab to control both news creation and distribution—a strategic asset for a potential presidential run. Mark’s vision reflects his defiance post-2016 election criticism and his belief that Facebook’s role in Trump’s win proves its kingmaker potential.

The “Rosebud” Moment

As the plane descends, Mark asks the narrator for her thoughts. She references Citizen Kane’s “Rosebud”—a nod to William Randolph Hearst’s media monopoly and political ambitions. Mark, unfamiliar with the film, doesn’t grasp the warning. Elliot explains the comparison, but Mark shrugs it off, asking, “Is that a bad thing?” The exchange underscores his detachment from historical parallels and his determination to reshape power structures on his own terms.

Key Takeaways

• Mark’s political ambitions solidify: His state-visit “challenge” mirrors a presidential campaign strategy, leveraging Facebook’s influence.
• Control over media = control over narrative: His plans to dominate news ecosystems highlight a desire to weaponize information for power.
• Defiance, not reflection: Criticism post-2016 election hardens Mark’s resolve to double down on dominance rather than reform.
• The narrator’s breaking point: The trip exposes her disillusionment with Mark’s moral trajectory, signaling her eventual exit.
• Echoes of history: The Citizen Kane reference foreshadows the dangers of unchecked ambition and media monopolies.

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Careless People Summary

37. Man of the People

Overview

The chapter captures Mark Zuckerberg’s calculated transformation into a public figure with political undertones. Amid a meticulously orchestrated cross-country tour—visiting factories, churches, Pride events, and rural communities—he crafts an image of a relatable, globally minded leader. Behind the scenes, his team optimizes social media posts and refines his persona, while his hiring of political strategists and publication of a lofty manifesto hint at ambitions beyond Silicon Valley. However, cracks in this polished narrative emerge during a land dispute in Hawaii, exposing tensions between his public image and private actions. Parallel to this, the narrator grapples with a dire health crisis, anchoring the personal stakes of maintaining employment at Facebook.

Crafting the Public Persona

Mark’s road trip through battleground states—Iowa, Michigan, Ohio, and others—is a strategic play for visibility. Photographers like Charles Ommanney, who documented U.S. presidents, capture him engaging with blue-collar workers, LGBTQ+ communities, and recovering addicts. These curated moments, amplified on Facebook, frame him as a “man of the people.” His lifestyle shifts—ditching fast food for fruit salads, daily workouts—signal a readiness for public scrutiny. Consultants David Plouffe and Ken Mehlman, architects of Obama’s and Bush’s campaigns, join his foundation, further blurring the line between tech mogul and political aspirant.

The Hawaii Land Scandal

Mark’s $700-acre Kauai estate becomes a liability when lawsuits against Native Hawaiians—including deceased individuals—over land titles spark outrage. Headlines like “Man of the People Mark Zuckerberg Sues to Keep Native Hawaiians Off His Kauai Estate” clash with his carefully constructed image. Initially vowing to sell the property, Mark pivots to a workaround: a retired professor covertly buys the disputed plots on his behalf. The scheme backfires when the professor brags about being paid $6,000 monthly by Zuckerberg, reigniting accusations of neocolonialism.

Corporate Machinations and Political Ambitions

Facebook’s board approves a new stock structure allowing Mark to leave for up to two years to pursue “government service”—a thinly veiled nod to a presidential run. Internal texts between Mark and board member Marc Andreessen (“The cat’s in the bag and the bag’s in the river”) reveal casual confidence in sidelining shareholder concerns. Despite board hesitations, Mark secures control, cementing his dual identity as CEO and aspiring statesman.

The Narrator’s Health Crisis

Amid Mark’s political maneuvering, the narrator faces a looming medical nightmare: Lynch syndrome, a genetic condition causing aggressive precancerous growths in their bowel. With twelve growths removed post-childbirth and no clear answers, doctors recommend a full bowel removal to prevent cancer. The narrator’s dependency on Facebook’s health insurance traps them in the company, despite job inquiries at Google and think tanks.

Key Takeaways

• Mark Zuckerberg’s cross-country tour and hiring of political strategists signal a deliberate shift toward national leadership, framed by social media optimization.
• The Hawaii land scandal undermines his “man of the people” image, exposing ethical contradictions and sparking public backlash.
• Facebook’s revised stock structure prioritizes Mark’s political aspirations over corporate transparency, drawing internal and legal scrutiny.
• The narrator’s health struggles highlight the human cost of corporate dependency, particularly in a broken healthcare system.
• Mark’s hypersensitivity to media criticism mirrors the vulnerabilities of a politician, not a detached tech CEO.

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38. Let Them Eat Cake

Overview

The chapter captures a pivotal moment of personal and professional reckoning for the narrator as tensions with Sheryl Sandberg escalate against the backdrop of Donald Trump’s inauguration and the historic Women’s March. Set during a flight back from Davos, the narrative juxtaposes the narrator’s growing disillusionment with Facebook’s leadership, financial entanglements, and Sheryl’s detachment from real-world crises with the grassroots energy of the protests unfolding nationwide.

The Davos Aftermath and Sheryl’s Inner Circle

The flight home from Davos reveals the toxic dynamics within Sheryl’s team. Despite outward displays of loyalty, her closest advisers privately mock her during a WhatsApp group chat, criticizing her reliance on stale anecdotes (like the oft-repeated “Pigtails and Pony” story) and her refusal to address Facebook’s controversies. The narrator notes the hypocrisy of these same individuals later showering Sheryl with praise, highlighting a culture of performative obedience. Sheryl’s obsession with controlling her public image—demanding front-row admiration from her team—clashes with the narrator’s quiet rebellion, such as refusing to applaud or offer flattery.

Financial Chains and Silent Dissent

Facebook’s equity grants loom large as a barrier to leaving the company. The narrator reflects on how lucrative stock options—worth millions over four years—trap employees in silence, even as ethical concerns mount. Sheryl’s tendency to “shoot the messenger” discourages honesty, with colleagues like Elliot and Joel advising against raising unresolved issues (e.g., Sheryl’s unresolved arrest warrant in Seoul or the stalled “Project Family”). The financial stakes underscore the moral compromise of staying, particularly for the narrator, who is the primary earner for her family.

The Women’s March vs. Sheryl’s Indifference

As millions protest globally, the narrator tries to engage Sheryl with news of the historic Women’s March, only to be met with apathy. Sheryl redirects the conversation to superficial topics: redecorating her ski house, private jet logistics, and Melania Trump’s attire. The contrast between the grassroots movement (sparked by a Facebook post) and Sheryl’s disinterest underscores her detachment from the platform’s societal impact. The narrator’s silent frustration peaks when Sheryl prioritizes Melania’s fashion over the march, evoking the infamous “Let them eat cake” sentiment.

Key Takeaways

• Culture of Fear: Dissent at Facebook is stifled by financial incentives and Sheryl’s punitive response to criticism, fostering a culture of sycophancy.
• Ethical Disconnect: Leadership’s focus on image over substance—exemplified by Sheryl’s indifference to the Women’s March—reveals a gap between Facebook’s public mission and its internal priorities.
• Personal Cost: The narrator grapples with the moral toll of staying at Facebook, weighed against the financial security her equity grants provide.
• Power Dynamics: Sheryl’s manipulation of her team (e.g., inviting subordinates to her jet’s bedroom) and fixation on status symbols illustrate the corrosive effects of unchecked power.

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Careless People Summary

39. Facebook Feminist Fight Club

Overview

The chapter delves into the undercurrents of discontent among women at Facebook, catalyzed by the formation of the secret Feminist Fight Club (FFC). This grassroots group emerges as a response to systemic gender inequities and leadership’s performative solutions, contrasting sharply with Sheryl Sandberg’s public advocacy for women. The narrative follows the author’s personal reckoning with harassment, bureaucratic indifference, and the ethical compromises demanded by Facebook’s power structures.

The #Ally Bot Debacle

Management’s response to the FFC’s activism—a bot designed to reward men for basic allyship—highlights the company’s preference for optics over accountability. The bot awards “Ally badges” tied to performance reviews, sparking outrage among FFC members. Women critique the absurdity of praising men for minimal decency while their own experiences of harassment and discrimination go unaddressed. One member quips, “You don’t get a cookie for not being a scumbag,” underscoring the bot’s hollow symbolism.

Whispered Warnings and Global Harassment

The FFC becomes a lifeline for women sharing stories of harassment across Facebook’s global offices. The author recounts a colleague’s warning about a predatory manager and reveals a pattern of misconduct shielded by corporate silence. From Korea to California, women trade hushed advice to avoid abusive superiors, knowing formal complaints often lead to retaliation, not justice. The open-office design and geographic distance offer no protection, as power imbalances enable predators to operate with impunity.

Elliot’s Indifference and Legal Gambits

After confronting HR head Elliot about Joel’s harassment and being met with dismissiveness, the author pivots to legal channels. During a separate investigation into Facebook’s practices in the Philippines, she documents Joel’s behavior with company lawyers. Joel’s allies soon pressure her to stay silent, invoking “loyalty” as a threat. When investigators ask if she wants to pursue action, the author confronts Elliot again, who implies compliance is the only path to safety.

Retaliation and the China Ultimatum

Joel retaliates by stripping the author of her leadership role in Asia unless she oversees Facebook’s controversial China operations—a policy she morally opposes. Choosing integrity over career advancement, she accepts a diminished role in Latin America and Canada. Joel and Elliot retaliate further, forcing her to recruit her own replacement for Asia while still demanding she work on China initiatives. The move exposes the company’s willingness to weaponize ethics against dissenters.

Key Takeaways

• Collective Action vs. Performative Fixes: The FFC’s solidarity contrasts with leadership’s empty gestures (e.g., #ally bot), revealing systemic indifference to gender issues.
• Silence as Complicity: Facebook’s culture protects harassers, leaving women to rely on informal networks for survival.
• Retaliation Over Resolution: Reporting misconduct often triggers punishment, not accountability.
• Ethical Compromises: Employees face impossible choices between career advancement and personal integrity, particularly in morally fraught projects like Facebook’s China expansion.
• Leadership Failure: Sandberg’s public feminism and internal HR structures crumble under scrutiny, prioritizing reputation over meaningful change.

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40. Greetings from Beijing

Overview

The chapter plunges into the ethical quagmire of Facebook’s pursuit of a foothold in China, despite the platform being banned in the country. Narrated from the perspective of an unwilling leader thrust into managing Facebook’s China policy, the story reveals the company’s morally fraught strategies to appease the Chinese Communist Party (CCP). As the narrator uncovers internal documents, they confront Facebook’s willingness to compromise user privacy, enable surveillance, and align with authoritarian demands—all while grappling with the human cost of these decisions.

Facebook’s China Ambitions

By early 2017, Facebook’s leadership—including Mark Zuckerberg, Joel Kaplan, and Vaughan Smith—had intensified efforts to penetrate the Chinese market. Despite the platform’s ban, China already contributed an estimated $5 billion annually (10% of total revenue) through ads sold to Chinese businesses targeting users abroad. The narrator, reluctantly taking charge of China policy, discovers a labyrinth of opaque strategies and high-level political maneuvering, including partnerships with influential figures like Henry Kissinger and former U.S. Treasury officials.

The Surveillance Pitch

Internal documents reveal Facebook’s explicit offer to the CCP: leveraging its platform to advance China’s global influence and enforce “safe and secure social order.” This included promoting state-aligned narratives like “the China dream” and enabling surveillance through real-name profiles and compliance with local laws. The company positioned itself as a tool for mass data collection, implicitly suggesting it could grant China access to user information—publicly or privately—to monitor dissent.

A chilling section of the pitch quotes Chinese Minister Lu Wei: “Liberty cannot exist without order,” signaling Facebook’s readiness to align with censorship and state control. The narrator speculates whether Facebook would directly handle content moderation (deleting posts, scanning private messages) or outsource it to a Chinese partner, raising questions about accountability for human rights abuses.

Internal Debates and Ethical Red Flags

Facebook’s leadership openly debated the risks of self-managing censorship versus using a local partner. Pros included retaining control and avoiding profit-sharing, while cons highlighted dire ethical consequences: employees could face responsibility for data requests leading to “death, torture, and incarceration.” Shockingly, Joel Kaplan edited the final document to soften this language, replacing it with a vague reference to governments that “do not respect international human rights standards.”

Despite these warnings, Zuckerberg and executives prioritized maintaining direct communication with the CCP over mitigating harm. The narrator reflects on Facebook’s indifference to the human toll of its decisions, noting how far leadership was willing to go to secure market access.

Key Takeaways

• Forced Compliance: The narrator’s involuntary role underscores Facebook’s loyalty-testing culture and its prioritization of growth over employee agency.
• Financial Incentives: China’s $5 billion revenue stream drove aggressive, ethically dubious strategies to bypass the platform’s ban.
• Surveillance as a Bargaining Chip: Facebook positioned user data and censorship tools as leverage to gain CCP approval, ignoring risks to global users.
• Moral Evasion: Internal documents reveal deliberate obfuscation of human rights risks, with leadership downplaying consequences like torture or imprisonment.
• Corporate Complicity: The chapter lays bare how tech giants can enable authoritarian regimes, trading ethical boundaries for market access.

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Careless People Summary

41. Our Chinese Partner

Overview

This section delves into Facebook’s covert efforts to penetrate the Chinese market through Project Aldrin, a partnership with Hony Capital (codenamed “Jupiter”). The initiative required Facebook to comply with stringent Chinese censorship demands, including localized data storage, content moderation tools tailored to government needs, and direct collaboration with Chinese authorities. The chapter exposes the ethical and operational compromises Facebook made to appease the Chinese Communist Party (CCP), while highlighting internal concerns about hypocrisy, data security risks, and the potential fallout from public exposure.

Strategic Partnership with Hony Capital

Facebook’s entry into China hinged on Hony Capital, a private equity firm tasked with managing Chinese user data and enforcing state-mandated censorship. Hony would oversee a content moderation team aligned with CCP directives, including scrubbing banned topics and sharing user data with authorities. Facebook developed advanced tools—facial recognition, photo tagging, and virality counters—to automate censorship. These tools allowed Hony to monitor and remove content globally, even if it originated outside China.

Censorship Infrastructure and Emergency Protocols

The collaboration included extreme measures to suppress dissent. An “emergency switch” could isolate regions like Xinjiang, while an “Extreme Emergency Content Switch” targeted viral posts during politically sensitive periods (e.g., the Tiananmen Square anniversary). Content reaching 10,000 views by Chinese users triggered automatic scrutiny. Notably, these tools were tested in Hong Kong and Taiwan, despite Facebook’s public claims of respecting regional autonomy.

Collaborative Efforts with Chinese Authorities

Facebook courted CCP approval by offering technical expertise, including AI and VR briefings, and inviting Huawei—a firm linked to state surveillance—into its Open Compute Project. A draft letter from Mark Zuckerberg to China’s Cyberspace Administration pledged cooperation in combating “terrorism,” a term the CCP broadly applies to Uighur activists, Falun Gong, and Tibet advocates. Meanwhile, the CCP exploited Facebook ads to spread propaganda denying human rights abuses.

Data Infrastructure and Security Risks

To support Chinese operations, Facebook partnered with Google and Pacific Light Data Communication to build a U.S.-China undersea cable, despite warnings about data interception. The company also deployed Points of Presence (PoP) servers in China, risking exposure of non-Chinese users’ data under local laws. Internal documents acknowledged high risks of Chinese espionage, including compromised credentials and malware attacks on Facebook’s network.

Internal Conflicts and Public Contradictions

Facebook’s actions starkly contradicted its global policies. While refusing data localization in Russia, Indonesia, and Brazil, the company surrendered Chinese user data to the CCP. Internal emails admitted much censored content wasn’t illegal but merely “objectionable to authorities.” Staff feared leaks exposing discrepancies between public statements and private dealings, even proposing “leak co-ordination” with Chinese officials to mitigate fallout.

Key Takeaways

• Facebook developed bespoke censorship tools for China, enabling real-time suppression of dissent and compliance with CCP demands.
• User data for Chinese citizens—and potentially non-Chinese users—was stored locally, exposing it to government access.
• The company prioritized market access over ethical standards, collaborating with controversial entities like Huawei.
• Internal risk assessments flagged high probabilities of espionage and U.S. government retaliation.
• Facebook’s actions in China starkly contrasted with its resistance to similar demands from other governments, revealing strategic hypocrisy.

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Careless People Summary

42. Respectfully, Senator

Overview

The chapter delves into Facebook’s high-stakes strategy to launch its platform in China while navigating ethical dilemmas, potential political fallout, and public distrust. Central to the narrative is the tension between the company’s expansion ambitions and its awareness of how compromising with China’s authoritarian regime could damage its reputation and invite scrutiny from U.S. lawmakers. Internal documents reveal meticulous planning to spin the narrative, suppress criticism, and prepare Mark Zuckerberg for hostile congressional questioning—all while sidestepping full transparency.

Strategic Preparations and Public Perception

Facebook’s entry into China hinged on a carefully orchestrated rollout, starting with a “Representative Office” and a planned New York Times op-ed by Nicholas Kristof. The op-ed aimed to frame Facebook’s presence as a benign force for global exposure, downplaying its compliance with censorship. Internally, the team fretted over hypothetical headlines accusing Facebook of enabling Chinese surveillance, conducting focus groups that starkly revealed public skepticism about the company’s commitment to privacy.

To mitigate backlash, Facebook allocated funds to co-opt potential critics like Human Rights Watch, seeking to “neutralize” opposition. Meanwhile, Zuckerberg set a modest success metric: capturing just 20% of China’s internet users—still a massive audience compared to Russia’s market.

Anticipating Congressional Backlash

Joel Kaplan, Facebook’s policy chief, flagged China as a top risk, prompting a “United States Impact Analysis.” The report predicted lawmakers would weaponize the launch to posture as tough on China, triggering hearings across multiple congressional committees. Critics, including intelligence officials, were expected to accuse Facebook of hypocrisy for resisting U.S. surveillance reforms while kowtowing to Beijing.

Zuckerberg’s rehearsed defense centered on claims that Facebook would operate under the same constraints as domestic Chinese platforms. This ignored the volatile nature of censorship in authoritarian regimes, where permissible speech could become punishable overnight.

Crafting Evasive Responses

Preparing for congressional questioning, Facebook’s legal and PR teams drafted non-answers to deflect scrutiny. A key tactic was outsourcing censorship decisions to “Jupiter” (a joint venture partner), despite Facebook owning the underlying technology. When pressed on data access, Zuckerberg was coached to insist Chinese data would be siloed—a half-truth that ignored the presence of global user data on Chinese servers (via PoP infrastructure).

Internal comments revealed a willingness to obscure facts. Joel Kaplan advised withholding details about PoP servers unless directly asked, highlighting a strategy of minimal disclosure.

Ethical Boundaries and Mock Hearings

In “Murder Board” sessions, Zuckerberg practiced deflecting questions about red lines, such as surrendering encryption keys. The team even gamed out comparisons to Nazi collaboration, scripting Zuckerberg to call the analogy “unfair” and pivot to China’s economic achievements. This underscored a broader pattern: prioritizing mission-driven expansion over moral accountability.

The Senate Hearing and Aftermath

During a 2018 Senate hearing, Senator Catherine Cortez Masto pressed Zuckerberg on whether Facebook would comply with China’s censorship and data-localization laws. He dodged, claiming ignorance of China’s demands—a blatant falsehood, given Facebook’s years of collaboration with Chinese authorities to develop compliant tools. His evasive response, coupled with vague assurances, buoyed Facebook’s stock price, illustrating how obfuscation paid off.

Key Takeaways

• Strategic Deception: Facebook prioritized market access over transparency, crafting narratives and technical loopholes to obscure its cooperation with Chinese censorship.
• Congressional Gamesmanship: The company anticipated political backlash and rehearsed legally defensible—but ethically dubious—responses to avoid perjury.
• Ethical Flexibility: Internal discussions revealed a willingness to compromise user safety and privacy in authoritarian regimes, despite public pledges to the contrary.
• Consequences of Evasion: Zuckerberg’s misleading testimony shielded Facebook from immediate fallout but deepened skepticism about its accountability.

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Careless People Summary

43. Move Fast and Break the Law

Overview

This section delves into Facebook’s aggressive and legally dubious efforts to penetrate the Chinese market, revealing a pattern of high-stakes maneuvering, covert operations, and ethical compromises. Central to the narrative is the tension between Mark Zuckerberg’s obsession with entering China and the escalating risks faced by employees, the company’s integrity, and its relationship with the Chinese government. Key events include the secret launch of apps in China, the suppression of dissident Guo Wengui’s account under government pressure, and the internal chaos sparked by leaks to the media.

Hiring Dilemmas and Political Risks

The chapter opens with the challenge of hiring a China-based employee to manage government relations—a role fraught with danger due to China’s strict State Secrets Law. The author grapples with the ethical implications of recruiting someone who could face imprisonment if accused of sharing sensitive information. This concern is underscored by the fate of Lu Wei, the former head of China’s Cyberspace Administration (CAC), who was imprisoned after his pro-Facebook stance backfired. His downfall, linked to a highly publicized visit to Facebook’s headquarters, illustrates the precariousness of political alliances in China.

Negotiations with the New CAC Leadership

After Lu Wei’s removal, Facebook pivots to negotiate with his successor, Zhao Zeliang, who adopts a harder line. Zhao explicitly ties Facebook’s entry into China to its willingness to censor content, using exiled billionaire Guo Wengui as a litmus test. He demands Facebook take action against Guo’s criticism of the Chinese government, framing it as a prerequisite for cooperation. This pressure culminates in Facebook temporarily suspending Guo’s account in 2017—a decision later revealed to be directly influenced by Zhao’s threats, despite public denials.

Covert App Launches and Shell Companies

In a bold move, Facebook secretly launches apps in China through shell companies like Leaplock and IvyCo, circumventing legal requirements. The apps—rebranded versions of Moments and Flash—are stripped of Facebook’s branding and operated via a Chinese subsidiary fronted by employee Ivy Zhang. Internal documents reveal deliberate obfuscation: Ivy is paid through a third-party HR firm, and the apps’ user data is stored outside China, violating local laws. Senior leadership, including Zuckerberg and Sheryl Sandberg, initially remain unaware of these operations, which are later exposed by a New York Times investigation.

Internal Chaos and Legal Reckoning

The exposure of Facebook’s clandestine activities triggers internal panic. Legal and communications teams scramble to contain fallout, with executives downplaying the severity of violations. Revelations about fraudulent registration documents—including a fake office address and Ivy’s husband’s unauthorized involvement—highlight the haphazard execution of the China strategy. Despite warnings from Facebook’s CFO and lawyers about tax discrepancies and illegal hiring practices in China, the company continues to prioritize market access over compliance.

Aftermath and Ongoing Risks

Even after the apps are shut down, Facebook persists in testing China’s limits, applying for licenses under Ivy’s name and funneling $30 million into a murky “start-up incubator.” The chapter closes with unresolved legal exposure: Facebook’s chief representative in China operates without proper permits, leaving the company vulnerable to employee grievances or government crackdowns.

Key Takeaways

• Ethical Compromises: Facebook repeatedly prioritized market access over legal and ethical boundaries, censoring critics like Guo Wengui under direct government pressure.
• Covert Operations: The company employed shell companies, rebranded apps, and obscured employee relationships to sidestep Chinese regulations.
• Internal Dysfunction: Leadership tolerated high-risk, poorly executed strategies, ignoring warnings from legal and financial teams.
• Vulnerability: Facebook’s illegal hiring and operational practices in China left it exposed to regulatory blowback and internal whistleblowing.
• Public Deception: The company misled Congress, investors, and the media about its activities in China, framing censorship as technical glitches.

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44. Emotional Targeting

Overview

The chapter delves into a 2017 scandal involving Facebook’s targeted advertising practices, specifically its exploitation of teenagers’ emotional vulnerabilities. A leaked internal document reveals the company’s ability to monitor and target users aged 13–17 during moments of psychological fragility—such as feelings of worthlessness, anxiety, or body image concerns—to serve them ads for products like diet teas or beauty treatments. The narrative exposes internal conflicts among Facebook’s leadership, attempts to downplay the issue, and the moral compromises made to protect the company’s reputation and revenue.

The Leaked Document and Its Implications

A confidential Facebook presentation, created for an Australian bank, outlines how the company tracks teens’ online activity—including posts, interactions, and even deleted selfies—to identify emotional states like insecurity or stress. This data is then used to serve hyper-specific ads. The document’s leak sparks immediate backlash, with Facebook’s policy and safety teams caught off guard. Internal discussions reveal that such targeting is routine, extending beyond teens to groups like new mothers and ethnic minorities.

Internal Reactions and Ethical Concerns

Within Facebook’s crisis response team, reactions are mixed. While some employees express horror at the ethical implications, others treat the practice as business-as-usual. A privacy staffer confirms that customized emotional targeting is widespread, with teams actively developing tools to let advertisers automate the process. Efforts to propose an independent audit are shut down by executives like Elliot Schrage, who warns against creating a paper trail that could invite legal scrutiny.

Corporate Denial and Public Deception

Despite internal acknowledgments of guilt, Facebook’s leadership orchestrates a cover-up. A false public statement claims the company “does not offer tools to target people based on their emotional state,” contradicting internal evidence. Senior executives, including Sheryl Sandberg, approve the lie. A junior researcher in Australia is scapegoated and fired, while advertising executives privately express frustration, arguing that emotional targeting is a core part of Facebook’s business model.

The Advertising Executive’s Perspective

A call with a senior Australian ad executive highlights the disconnect between Facebook’s public denials and its internal pride in emotional targeting. The executive argues that precision ad targeting—including exploiting vulnerability—is a key revenue driver. Sheryl Sandberg’s subsequent praise of Facebook’s “competitive advantage” in age- and gender-based targeting underscores the hypocrisy, as it contradicts the company’s claims of innocence.

The Aftermath and Ongoing Risks

Years later, the consequences of these practices become tragically clear. The suicide of British teen Molly Russell, linked to Instagram content tagged with “Feeling Worthless,” exposes the real-world harm of emotional targeting. Internal documents later acknowledge a “palpable risk” of such incidents, but Facebook’s leadership continues prioritizing profit over accountability.

Key Takeaways

• Facebook systematically exploited teenagers’ emotional vulnerabilities for profit, using invasive data tracking to serve targeted ads during moments of psychological fragility.
• Internal culture prioritized revenue over ethics, with executives lying to the public and scapegoating low-level employees to avoid accountability.
• The 2017 scandal foreshadowed later tragedies, revealing how unchecked corporate practices can have devastating real-world consequences.
• Sheryl Sandberg and other leaders publicly contradicted internal realities, highlighting a pattern of deception to protect the company’s image.

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Careless People Summary

45. A Fish Rots from the Head

Overview

The chapter paints a stark picture of Facebook’s internal decay, tracing the erosion of trust between employees and leadership. Once a source of pride, the company now grapples with moral disillusionment, leadership detachment, and a culture increasingly indifferent to real-world harm. From tone-deaf executive responses to crises like Charlottesville and sexual harassment complaints, to the chilling indifference shown toward a contractor’s medical emergency, the narrative reveals a company struggling to reconcile its self-image as a force for good with the mounting collateral damage of its decisions.

Leadership Disconnect

Senior leaders like Sheryl Sandberg and Elliot Schrage appear oblivious to employee concerns. Sandberg expresses frustration that interns prioritize questions about ethics over business strategy, missing the generational shift in workplace values. Schrage’s attempt to boost morale by invoking Mark Zuckerberg’s “moral authority” backfires, highlighting how out of touch leadership is with staff who question whether that authority exists at all. Meanwhile, Zuckerberg doubles down on nostalgic, self-congratulatory narratives during company Q&As, framing critics as outsiders who “just don’t understand.”

Diversity Efforts as Theater

Joel Kaplan, Facebook’s VP of Global Public Policy, hosts awkward “diversity brown bag sessions” that devolve into performative gestures rather than meaningful dialogue. When an FFC member directly raises the issue of sexual harassment accountability, a senior male colleague shuts down the conversation, asking when women will “focus on work.” HR deflects with bureaucratic responses, reinforcing the perception that these sessions are mere pantomimes. Employees of color and women grow increasingly cynical as systemic issues remain unaddressed.

Charlottesville and Prioritization Failure

After the deadly Unite the Right rally in Charlottesville, employees push for Zuckerberg to address Facebook’s role in amplifying hate groups. However, a trivial question about gym overcrowding dominates the Q&A voting, underscoring a broader apathy among staff. Internally, Facebook had been warned about hate groups on its platform but delayed action until the eve of the rally. Leadership dismisses public criticism as a “witch hunt,” further alienating employees who see the company’s inaction as complicity.

Nationalist Rhetoric and Deflection

Zuckerberg and Sandberg adopt a defensive, tribal mindset, framing Facebook as a misunderstood victim under siege by external critics. This “us versus them” mentality mirrors nationalist propaganda, fostering a culture of “organized innocence” where employees are encouraged to see themselves as righteous pioneers. Internal dissent is stifled, and critics are dismissed as outsiders lacking the vision to appreciate Facebook’s mission.

The Seizure Incident

A contractor suffers a violent seizure in the office, foaming at the mouth and bleeding, while nearby employees—including her manager—ignore her, citing busyness or bureaucratic detachment. The incident becomes a metaphor for Facebook’s cultural decline: once a place where employees felt camaraderie, it’s now marked by cold indifference. The FFC members who step in face institutional barriers, as contractors are treated as disposable labor.

Key Takeaways

• Leadership denial: Executives prioritize self-mythologizing over accountability, dismissing ethical concerns as distractions.
• Performative inclusion: Diversity initiatives lack substance, reinforcing systemic inequities rather than addressing them.
• Moral apathy: Trivial issues like gym access overshadow urgent societal harms, reflecting a workforce increasingly numb to Facebook’s real-world impact.
• Deflection tactics: Criticism is framed as persecution, insulating leadership from scrutiny while deepening employee disillusionment.
• Cultural decay: Once marked by energetic idealism, Facebook’s culture now tolerates human suffering in pursuit of corporate efficiency.

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46. Myanmar

Overview

Myanmar’s explosive embrace of mobile internet in the mid-2010s turned Facebook into a lifeline—and a weapon. As telecom companies bundled the platform with cheap data plans, it became synonymous with the internet itself. But this unchecked growth came at a devastating cost. A single fabricated post in 2014, accusing a Muslim tea shop owner of rape, spiraled into deadly riots when content moderation failures allowed nationalist figures like monk Ashin Wirathu to amplify hate. With no Burmese-speaking staff and broken reporting tools, Facebook’s teams in Dublin struggled to act until violence erupted.

The platform’s technical infrastructure crumbled under cultural and linguistic realities. Burmese text, incompatible with non-Unicode systems, rendered posts unreadable to moderators. Unofficial, stripped-down Facebook apps dominated downloads, lacking basic safety features. These flaws weren’t oversights but symptoms of systemic neglect: executives dismissed fixes as low-priority even as elections approached. In 2015, pro-democracy candidates found their accounts mysteriously suspended after mass reporting, while junta-backed disinformation flourished. Civil society groups sounded alarms about racist slurs like kalar, but moderators allowed them to spread, deepening divisions.

Behind the chaos lay leadership indifference. Requests for Burmese-speaking staff or crisis experts were brushed aside, with executives insisting teams “did exactly what they were supposed to do.” Bureaucratic paralysis stalled hiring as internal reports exposed coordinated hacking campaigns. By 2017, this apathy enabled genocide. Military operatives hijacked verified celebrity pages to flood feeds with anti-Rohingya propaganda, framing the minority as existential threats. Fake accounts stoked fear, while hacked activists faced arrest. Facebook’s security teams identified malicious groups coordinating violence but took no action—even as the UN documented mass atrocities fueled by the platform.

The Myanmar military’s exploitation of Facebook revealed a stark truth: the company’s growth-first ethos left its systems weaponizable. Moderators lacked language skills and cultural context, automated tools failed to detect hate speech, and leadership dismissed crises with callous quips like “Drop a bomb on it.” While Sheryl Sandberg and Mark Zuckerberg prioritized expansion, their platform became a blueprint for state-backed terror. The result wasn’t just broken algorithms but a moral collapse—one that turned a nation’s digital awakening into a nightmare of fire, blood, and silence.

Facebook's Role in Myanmar's Internet Surge

Myanmar’s rapid adoption of mobile internet between 2013 and 2017 transformed Facebook into the de facto internet for millions. Telecom partnerships preloaded Facebook on phones, and data plans often exempted Facebook usage from limits. This ubiquity made the platform inseparable from daily life—and its flaws catastrophic.

2014 Riots and Content Moderation Failures

A fabricated Facebook post in 2014, alleging a Muslim tea shop owner raped a Buddhist woman, ignited deadly riots. The post was amplified by Ashin Wirathu, a nationalist monk dubbed the “Burmese Bin Laden.” Facebook’s content team, lacking Burmese-speaking staff, delayed removing the posts for hours. Moderators in Dublin relied on a single contractor—unreachable during the crisis—to assess the content. By the time the posts were removed, violence had already erupted, leading Myanmar’s junta to temporarily block Facebook.

Systemic Neglect and Technical Barriers

Behind the moderation failures lay deeper technical neglect:

• Facebook’s interface and reporting tools weren’t translated into Burmese.
• The platform couldn’t process Myanmar’s non-Unicode text, rendering posts unreadable to moderators outside the country.
• Unofficial, stripped-down Facebook apps dominated downloads, lacking basic reporting features.
  Efforts to fix these issues were dismissed as low-priority, despite Myanmar’s 60 million users.

Election Interference and Internal Sabotage

Before Myanmar’s landmark 2015 election, Facebook’s dysfunction enabled targeted suppression. Pro-democracy candidates’ accounts were mass-reported as fake and suspended. Civil society groups used secret channels to alert Facebook’s policy team to hate speech and junta-backed disinformation. Moderators in Dublin, suspected of bias, allowed slurs like kalar (a racist term for Muslims) to proliferate. Meanwhile, activists faced arrest for posts deemed critical of the military.

Leadership Indifference and Hiring Paralysis

Repeated pleas to Facebook’s leadership for dedicated Myanmar staff—including a Harvard-connected human rights expert—were rebuffed. Executives dismissed concerns, insisting content teams “did exactly what they were supposed to do.” Hiring approvals stalled over bureaucratic excuses, even as internal reports confirmed coordinated hacking campaigns and fake accounts inflaming ethnic tensions.

Escalation to Genocide

By 2017, military-linked operatives weaponized Facebook to orchestrate violence against Rohingya Muslims. Fake news, hacked accounts, and incendiary posts stoked fear, culminating in a genocidal campaign documented by the UN. Survivors described mass rape, arson, and executions—all amplified by a platform that prioritized engagement over safety. Facebook’s security team identified malicious groups coordinating attacks but took no meaningful action.

Section 2 will cover the aftermath of the genocide, international scrutiny, and Facebook’s delayed response.

Military Exploitation of Facebook

The Myanmar military weaponized Facebook by hijacking verified accounts with massive followings—including fan pages for celebrities and national heroes—to disseminate hate speech and misinformation. According to Paul Mozur’s New York Times investigation, military-linked troll accounts amplified this content, silenced critics, and stoked online conflicts. Facebook acknowledged removing some inauthentic accounts but avoided probing ties to the military, despite clear evidence of state-backed manipulation.

Facebook’s Role in Escalating Violence

A UN report detailed Facebook’s central role in enabling human rights abuses, documenting widespread anti-Muslim rhetoric, including dehumanizing slurs like kalar and narratives framing Rohingya as existential threats to Buddhism and racial purity. Extremist groups like MaBaTha, led by monk Wirathu, openly used the platform to incite violence. Death threats and harassment targeted not only Muslims but also activists, moderates, and dissenters.

Systemic Failures in Content Moderation

Facebook’s safeguards in Myanmar were critically flawed:

• Moderators lacked Burmese language proficiency and cultural context.
• Burmese text, not rendered in Unicode, complicated automated detection of hate speech.
• Reporting systems were opaque and unresponsive, even as internal data revealed Myanmar hosted 45% of Southeast Asia’s most active hate speech accounts.
  The UN criticized Facebook’s refusal to share country-specific hate speech metrics, hindering accountability.

Leadership Neglect and Indifference

The chapter attributes Facebook’s inaction to apathy among senior leaders. Joel, head of Facebook’s policy for conflict regions, dismissed crises with flippant remarks like “Drop a bomb on it.” Executives like Sheryl Sandberg and Mark Zuckerberg allegedly prioritized growth over implementing safeguards, despite years of warnings. The failure to act—described as “sins of omission”—reflected a systemic disregard for vulnerable communities.

Key Takeaways

1. Myanmar’s military exploited Facebook’s infrastructure to orchestrate state-backed hate campaigns.
2. Facebook’s inadequate moderation, language barriers, and opaque reporting systems enabled systemic abuse.
3. Leadership indifference—not resource constraints or malice—allowed human rights violations to escalate unchecked.

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Careless People Summary

47. It Really Didn’t Have to Be This Way

Overview

This chapter traces Sarah’s escalating struggles with systemic power imbalances, harassment, and institutional betrayal at Facebook. As Joel’s influence grows under Trump’s administration, his unchecked behavior becomes more brazen, culminating in public humiliation and physical harassment at a company offsite. Sarah’s attempts to protect herself—by seeking a transfer, confiding in HR, and pursuing an internal investigation—are systematically thwarted, exposing the company’s prioritization of power over accountability. The chapter closes with her abrupt termination, leaving her financially vulnerable and emotionally shattered.

The Offsite: Harassment in Plain Sight

The Trump administration’s rise solidifies Joel’s dual role as Facebook’s policy gatekeeper and political lobbyist, blurring ethical lines. At Elliot’s offsite event, Joel’s behavior escalates from creepy remarks to overtly sexualized aggression. He publicly labels Sarah “sultry” despite her deliberate efforts to appear unremarkable, then physically grinds against her during a karaoke session. Coworkers witness these acts but offer only fleeting sympathy, leaving Sarah isolated. A conversation with HR’s Stacey—who cryptically hints at darker company secrets—convinces Sarah that reporting Joel will backfire.

A Blocked Escape

Desperate to flee Joel’s orbit, Sarah negotiates a transfer to Javi’s growth team, proposing critical election-integrity projects in Germany. Despite alignment with Javi’s priorities and public scrutiny from Uber’s harassment scandal, Joel or Elliot block the move. In a tense meeting, Elliot feigns ignorance about Sarah’s documented struggles, implying her complaints threaten the status quo. When Sarah confronts him about the injustice of losing her job—and the financial stability tied to her equity—Elliet coldly terminates the discussion, signaling her expendability.

The Investigation Farce

After Uber’s Susan Fowler sparks industry-wide reckoning, Facebook’s HR opens a superficial investigation into Joel. Investigators twist facts to exonerate him: they dismiss his “sultry” comment as benign (claiming he was looking at a photo), ignore blocked hiring requests, and deem his invasive questions about Sarah’s postpartum body “unprovable.” The process shifts blame to Sarah, framing her as a poor communicator and underperformer. Elliot and HR weaponize Joel’s sabotage of her hiring efforts as grounds for dismissal, despite Sarah’s meticulous documentation.

The Firing

Sarah’s final performance review devolves into a legal ambush. Chief employment lawyer Heidi Schwartz joins Elliot to coldly terminate her, denying her even a farewell to her team. Escorted out by security, Sarah’s last interaction—a misinformed congratulations from a clueless executive—underscores the company’s detachment from its human consequences. The chapter closes with Sarah’s visceral panic over her family’s future, juxtaposed against Facebook’s sprawling, indifferent headquarters.

Key Takeaways

• Power Protects Power: Joel’s political clout and proximity to leadership shielded him from accountability, prioritizing Facebook’s government relations over employee safety.
• HR as a Liability: Internal investigations were performative, designed to silence victims rather than address misconduct.
• Systemic Retaliation: Attempting to transfer or report harassment triggered punitive measures, trapping targets in abusive dynamics.
• Personal Cost: Sarah’s firing—and loss of equity, health insurance, and stability—highlights how institutions punish those who challenge entrenched power.

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Careless People Summary

48. Just Business

Overview

This chapter serves as a raw, reflective account of the author’s disillusionment with Facebook after years of witnessing its moral and operational decay. It grapples with the tension between the platform’s original idealism—its potential to unite people globally—and its transformation into a tool for manipulation, surveillance, and violence. The narrative underscores the systemic failures of leadership to prioritize human dignity over profit and power, even when solutions were within reach.

The Exit and Its Weight

The author recounts their departure from Facebook, framing it as part of a broader pattern of silencing dissent, particularly toward women and critics within the company. Despite efforts to advocate for change from within, they describe feeling like “the grit in the machine”—ineffective and ultimately expendable. The emotional toll of this failure lingers, compounded by the knowledge that staying would have been equally untenable.

From Promise to Poison

Early memories of Facebook’s impact—reconnecting families, empowering marginalized communities, and fostering global connections—are starkly contrasted with its current role in amplifying hate, autocracy, and exploitation. The platform’s evolution into a “machine to turn people against each other” is portrayed as a betrayal of its founding vision. Specific examples, like enabling genocide in Myanmar and collaborating with authoritarian regimes, highlight the human cost of this shift.

The Myth of Inevitability

A central argument emerges: Facebook’s destructive path was not unavoidable. At critical moments—responding to election interference, hate speech, or crises like Myanmar—leadership consistently chose profit and expansion over accountability. The author rejects the idea that ethical decisions would have jeopardized the company’s success, pointing to its vast resources as proof that “a different path was possible.” Instead, executives prioritized vanity projects (like Mark Zuckerberg’s “artisanal Wagyu beef” ventures) and political maneuvering.

Indifference as Strategy

The chapter dissects the psychology of Facebook’s leadership, describing a culture of “lethal carelessness.” Decisions enabling violence or misinformation are framed not as tragic mistakes but as deliberate, calculated choices. The more harm Facebook causes, the less its leaders seem to care—a cycle the author attributes to unchecked power and a lack of consequences. Their indifference is portrayed as both a moral failing and a business strategy, where human suffering is collateral in pursuit of growth.

Key Takeaways

1. Ethical failure was a choice: Facebook’s leadership had ample resources and opportunities to mitigate harm but repeatedly prioritized profit.
2. Power corrupts incrementally: Small, daily compromises—not grand, singular decisions—normalized the company’s destructive practices.
3. The human cost is systemic: From Myanmar to U.S. elections, Facebook’s tools disproportionately empower autocrats and extremists.
4. Silencing dissent is strategic: Marginalizing critics (especially women) allowed toxic cultures to persist unchallenged.
5. No redemption arc: The author offers no hope for internal reform, framing leadership’s indifference as entrenched and deliberate.

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Careless People Summary

Epilogue

Overview

The epilogue ties together the fates of key figures from Facebook’s inner circle, the author’s personal journey post-Facebook, and the looming ethical battles in tech. It juxtaposes the unchecked rise of Meta’s power with the author’s advocacy work, while raising urgent questions about artificial intelligence’s role in global conflict and corporate accountability. From political scandals to life-threatening pregnancies, the narrative underscores how personal and systemic recklessness collide in a world shaped by Silicon Valley’s decisions.

Joel’s Loyalty and Meta’s Influence

Joel’s public support for Brett Kavanaugh during the Supreme Court nomination hearings sparks internal backlash at Facebook. Despite issuing a half-hearted apology, he doubles down by hosting a celebration for Kavanaugh, signaling his alignment with power over principle. His promotion to Meta’s upper echelons cements his role in pivotal decisions, including content moderation during the January 6 riots and lobbying efforts to stifle competitors like TikTok. His trajectory embodies Meta’s prioritization of political maneuvering over ethical governance.

Fallout for Facebook’s Leadership

• Elliot’s Exit: Resigns after Facebook’s ties to Definers, a Republican opposition firm, surface. The firm targeted critics like George Soros with anti-Semitic smears. Though Elliot takes responsibility, internal investigations later reveal Sheryl Sandberg’s involvement.
• Sheryl Sandberg’s Downfall: Once a corporate icon, Sandberg faces scrutiny for misusing company resources—including staff support for her Lean In foundation and efforts to suppress negative press about her ex-boyfriend, Activision CEO Bobby Kotick. Her departure in 2022 marks a symbolic end to her carefully curated legacy.

Mark Zuckerberg’s Metaverse Gambit

Zuckerberg shifts from apology tours to unabashed self-mythologizing, rebranding Facebook as Meta and pouring billions into the metaverse. Critics compare the venture to past failures like the Facebook Phone or Libra cryptocurrency. Despite skepticism, Zuckerberg’s control remains unchallenged, with Meta’s stock buoyed by AI hype. His focus on virtual worlds contrasts sharply with real-world crises the company continues to fuel.

Personal Resilience and Advocacy

The author navigates a high-risk pregnancy following a near-fatal amniotic embolism, defying medical warnings to welcome a healthy child. Parallel to this personal triumph, she collaborates with activists like Ifeoma Ozoma to pass California’s Silenced No More Act, empowering whistleblowers. She also challenges Meta through shareholder resolutions and a SEC complaint, highlighting the company’s opaque dealings with China and resistance to accountability.

AI: The New Cold War Frontier

The author’s work on U.S.-China Track II Dialogue exposes existential questions about AI in warfare: Should autonomous systems control nuclear retaliation? Can open-source AI models avoid fueling geopolitical arms races? Meta’s push for open-source AI clashes with experts like Sam Altman, who warn it risks handing China technological supremacy. The debate underscores Meta’s recurring pattern of prioritizing growth over global consequences.

Key Takeaways

1. Meta’s Unchecked Power: Leadership like Joel and Zuckerberg wield disproportionate influence over policy and public discourse, shielded by corporate structures that evade accountability.
2. Ethical Erosion: From Definers’ smears to Sandberg’s resource abuse, Meta’s culture rewards loyalty over integrity.
3. Personal vs. Systemic Risk: The author’s advocacy and health struggles mirror broader battles against corporate and technological recklessness.
4. AI’s Existential Stakes: Autonomous weapons and open-source AI models demand urgent governance—a challenge complicated by Meta’s profit-driven agenda.
5. The Cycle of Carelessness: Without transparency, Meta’s past failures—amplified by AI—threaten to reshape global conflict and democracy itself.

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