What is *Red Team* by Micah Zenko about?

*Red Team* explores the practice of red teaming—adopting adversaries’ perspectives to identify organizational vulnerabilities. Micah Zenko traces its origins in military strategy, CIA counterterrorism efforts, and business applications, using case studies like the hunt for Osama bin Laden. The book provides frameworks to challenge assumptions, avoid groupthink, and enhance decision-making through structured skepticism and alternative analysis.

Who should read *Red Team*?

Security professionals, corporate strategists, and policymakers will find *Red Team* invaluable. It’s particularly relevant for leaders in cybersecurity, risk management, and military planning, as well as executives seeking to anticipate competitor moves. Zenko’s blend of historical examples and practical advice caters to anyone responsible for high-stakes decision-making.

Is *Red Team* worth reading?

Yes—*Red Team* is praised for its rigorous research and actionable insights into mitigating blind spots. While critics note ambiguities about whether red teaming is an innate skill or teachable practice, the book remains essential for understanding adversarial thinking. Its real-world applications in security and business make it a standout resource.

Who is Micah Zenko, the author of *Red Team*?

Micah Zenko is a political scientist, Senior Fellow at Chatham House, and former Council on Foreign Relations expert. With a PhD from Brandeis University, he’s authored books on military operations and national security. His work combines academic analysis with insights from 250+ interviews with red team practitioners.

What is red teaming according to Micah Zenko?

Red teaming is a disciplined process of simulating adversarial perspectives to stress-test strategies. Zenko frames it as a tool to combat groupthink, challenge assumptions, and uncover hidden risks. Originating in military war games, it’s now applied to cybersecurity, corporate strategy, and counterterrorism.

What are real-world examples of red teaming in the book?

Key examples include: - The CIA’s pre-9/11 counterterrorism simulations. - The NYPD’s post-9/11 threat scenarios. - U.S. Army reforms through the University of Foreign Military Studies. - Corporate exercises to hack internal systems or disrupt business models.

How does red teaming differ from traditional analysis?

Traditional analysis optimizes existing plans, while red teaming seeks to dismantle them. Zenko emphasizes role-playing, war gaming, and alternative hypotheses to expose flaws. Unlike consensus-driven methods, red teams operate independently to prioritize critical inquiry over confirmation bias.

What are the key takeaways from *Red Team*?

1) Institutionalize adversarial thinking to avoid complacency. 2) Separate red teams from operational planners to maintain objectivity. 3) Use structured techniques like “pre-mortems” to anticipate failures. 4) Apply lessons across contexts—from cybersecurity to product launches.

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Micah Zenko

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Visão geral de Equipe Vermelha

Descubra como organizações de elite expõem suas próprias vulnerabilidades antes que os inimigos o façam. O "Red Team" da Zenko revela os seis princípios por trás do pensamento adversarial militar e corporativo que revolucionou a cibersegurança. Quais pontos cegos estão custando caro para você agora que um "cético destemido" poderia identificar?

Escolha como a história é contada

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Capítulo 1

When Red Teams Save the Day: Inside the Secret World of Adversarial Thinking

Imagine being the person who could have prevented 9/11. In the years leading up to the attacks, a small team within the Federal Aviation Administration repeatedly exposed alarming vulnerabilities in airport security. They smuggled fake bombs past screeners, accessed restricted areas, and boarded aircraft undetected. Their warnings? Systematically ignored. This wasn't incompetence-it was institutional blindness, the kind that plagues organizations worldwide. When the 9/11 Commission investigated the attacks, they concluded: "What happened on 9/11 was not a failure in the system, it was a system designed for failure." This pattern repeats across industries and institutions. From military disasters to corporate collapses, organizations consistently fail to identify their own weaknesses. In 2014, General Motors recalled millions of vehicles with faulty ignition switches linked to at least 119 deaths-despite employees having flagged the issue years earlier. The problem wasn't that GM lacked information; it was that they had created a culture where employees were trained to use watered-down language that understated safety issues. Enter red teaming-a structured approach to challenging an organization's plans, systems, and assumptions by adopting an adversarial perspective. Originally developed in military and intelligence circles, this practice has spread to corporations, cybersecurity firms, and homeland security agencies. Through the stories of over 200 practitioners-from former CIA directors to ethical hackers-Micah Zenko's investigation reveals how organizations can overcome their blind spots before disaster strikes. Whether preventing terrorist attacks or avoiding market failures, red teams offer a powerful tool for seeing what we otherwise cannot: our own vulnerabilities.

Capítulo 2

The Fundamental Problem: You Cannot Grade Your Own Homework

Organizations develop strategies, plans, and processes essential to their functioning. Yet they face a fundamental dilemma: determining when these standard approaches are producing suboptimal outcomes or leading toward disaster. The central challenge is that "you cannot grade your own homework" - a simple phrase that encapsulates a complex organizational challenge that affects institutions from Fortune 500 companies to government agencies. Self-assessment creates dangerous blind spots that can have catastrophic consequences. The CIA's post-9/11 detention and interrogation program serves as a stark example, where effectiveness was evaluated by the same personnel who developed it. Despite numerous requests for external review from Congress and other oversight bodies, the CIA never commissioned proper independent analysis. This internal echo chamber led to years of ineffective and ethically questionable practices. An informed red team could have provided realistic evaluation of the torture program and recommendations for revision or termination, potentially saving both resources and lives. Senior leaders often cannot identify their organization's most dangerous shortcomings due to two fundamental constraints: cognitive biases and organizational dynamics. Cognitive biases like mirror imaging (assuming others think like you) and confirmation bias (favoring information that supports existing beliefs) make self-evaluation difficult. The Dunning-Kruger effect compounds this problem - the least competent people are also the worst judges of their own performance. This creates a dangerous feedback loop where incompetence breeds overconfidence, leading to poor decision-making at critical junctures. Organizational biases further exacerbate these problems in ways that become deeply embedded in institutional culture. As economist Thorstein Veblen observed, employees become "captured" by institutional culture and adopt their bosses' preferences, often unconsciously. This "going native" phenomenon is especially prevalent in hierarchical organizations or those requiring deep immersion in specialized knowledge, such as intelligence agencies, medical institutions, and financial firms. Military officers score significantly lower than the general population on openness to new ideas, demonstrating how certain organizational cultures actively discourage divergent thinking and creative problem-solving. Though leaders frequently claim to welcome dissent and alternative viewpoints, employees rarely risk their careers by highlighting problems or challenging conventional wisdom. One Marine officer aptly noted: "Your ability to mind read is more praiseworthy than your ability to think critically." This explains why GM employees avoided direct language about safety issues, using euphemisms like "does not perform to design" instead of "stalls" or "dies," contributing to dozens of preventable deaths. Similar patterns emerged in NASA's Challenger disaster and Boeing's 737 MAX crisis, where organizational pressure to maintain schedules and profits overshadowed safety concerns. Red teaming addresses these blind spots through three core techniques: simulations (modeling scenarios to test strategies), vulnerability probes (testing defensive systems as an adversary would), and alternative analyses (challenging assumptions through structured techniques). Whether comprised of external consultants or internal employees, red teams help institutions visualize themselves outside daily routines, evaluate plans objectively, identify vulnerabilities, and potentially improve performance. Successful implementations at companies like IBM and organizations like the U.S. military demonstrate how structured opposition can lead to better outcomes and more resilient organizations.

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Capítulo 3

The Boss Must Buy In: Leadership Support Makes or Breaks Red Teams

The most critical factor determining red team success is genuine leadership support. As retired Marine Lieutenant General Paul Van Riper emphatically declares: "Unless the commanders themselves want it, support it, resource it, institutionalize it, and respond to it, it won't matter." This fundamental truth has been demonstrated repeatedly across military, corporate, and government organizations. This essential buy-in must manifest in several concrete ways. First, bosses must recognize specific vulnerabilities within their organization that red teaming can address. This recognition often comes only after a catastrophic failure has occurred, as with the FAA's red team created in response to the 1988 Pan Am Flight 103 bombing over Lockerbie, Scotland. Some forward-thinking leaders, however, proactively seek red teaming before making consequential decisions, both to improve outcomes and provide strategic "cover" if things go wrong. Microsoft, for instance, regularly employs red teams to probe new software releases before launch, demonstrating preventive rather than reactive leadership. Buy-in must cascade effectively throughout the organizational hierarchy. When red teaming is merely imposed from above without proper context and instruction on its value, junior leaders often "sleepwalk" through the process, treating it as just another box to check. This occurred with Marine Expeditionary Forces when red teams were mandated without adequate explanation of their purpose and potential benefits. Similar patterns emerged in corporate settings where red team exercises were treated as perfunctory compliance requirements rather than valuable strategic tools. Leaders must demonstrate their commitment through tangible resource allocation, including dedicated personnel, adequate funding, and protected time. This means avoiding the common pitfall of treating red teams as "dumping grounds" for underperforming employees or temporary assignments for staff between "real" jobs. Successful red teaming requires skilled practitioners who can think critically and communicate effectively. Leaders must also create an environment where red teamers can speak truthfully without fear of retribution, even when their findings challenge the boss's own strategies or pet projects. Exemplary leaders like General David Petraeus actively cultivate this environment, noting that "you have to create a culture that preserves and protects the iconoclasts." This includes attending red team exercises, publicly recognizing valuable insights, and promoting skilled red teamers. The consequences of inadequate leadership support can be severe, as demonstrated by the pre-9/11 FAA red team experience. Despite consistently exposing serious security vulnerabilities, the team was systematically undermined by leadership who sometimes tipped off airports about upcoming inspections or explicitly instructed team members to omit certain findings from their reports. When frustrated team members eventually went public with their concerns in 2001, they faced retaliation rather than having their warnings heeded-a tragic example of leadership failure with catastrophic consequences. Implementation authority is another crucial aspect of leadership support. Ideally, whoever commissions the red team should have direct authority to authorize implementation of its findings, or at minimum, direct access to those who do. The boss must make informed decisions about implementing recommendations based on comprehensive risk assessment and available resources. Red team exercises that are conducted but ignored can be more dangerous than no red teaming at all, as they create a false sense of security while critical vulnerabilities remain unaddressed.

Capítulo 4

Outside and Objective, While Inside and Aware: Finding the Right Balance

Red teams must balance competing demands: maintaining semi-independence and objectivity while remaining sensitive to the organization's environment and resources. They must avoid institutional capture while contributing to the core mission. As Jami Miscik, former CIA deputy director of intelligence, noted: "They cannot be a separate back-office group that studies their navels, and isn't engaged with the rest of the building." Three factors guide successful red team positioning: structure (where the team sits organizationally), scope (what activities it pursues), and sensitivity (how it operates and provides findings). Misunderstandings about these factors frequently cause red team failure. Structurally, red teams should be semi-independent, ideally on a dotted line reporting directly to senior leadership. Sometimes their relationship to the institution should be widely known, as with business war games; other times they should report only to the boss, as with General Petraeus's "directed telescope" reviews conducted by outside experts who reported findings directly and confidentially to him. Getting structure right ensures access to people and information. One Army colonel placed his red team in the middle of headquarters to signal their importance and ensure access. For outside teams, access depends on how tightly scoped the engagement is. Proper scoping prevents "scope creep" by establishing who or what is being red teamed, for how long, with what flexibility, and to what end. Red teams should calibrate their intensity appropriately-not overwhelming security teams but gradually increasing sophistication so lessons can be implemented. Red teams must operate with sensitivity, doing their homework about the institution's concerns, regulatory environment, resources, and timelines. They should never conduct "gotcha" exercises that embarrass individuals, nor cause inadvertent disruption. As Charles Henderson of Trustwave Holdings notes: "Our job isn't to break into a computer network or building, it's to improve the security of the client." The CIA Red Cell exemplifies effective positioning. Created after 9/11 to challenge conventional intelligence thinking, it evolved from making officials uncomfortable to becoming a structured, sought-after posting. Its impact comes partly from the Red Cell brand itself, with senior officials like Robert Gates valuing that they "never fallen off the edge of the world" while still stirring minds. Michael Hayden, CIA director from 2006-2009, found their work "a little too much like science fiction at times" but read everything they produced because he "wanted to have my mind stirred."

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Capítulo 5

Fearless Skeptics with Finesse: The People Who Make Red Teams Work

Successful red teams require members who think differently from everyone else in the organization. They're often self-described "oddballs" and "weirdoes"-critical, divergent thinkers inherently skeptical of authority and conventional wisdom. As Lieutenant Colonel Daniel Geisenhof put it, "In many ways, we are in the land of misfit toys." While most people believe they think outside the box, few actually do without training. Humans naturally exhibit "existence bias"-assuming current conditions must be correct, which overvalues precedents and status quo. Effective red teamers escape these constraints through distinct personality types, proper training, or semi-independence. Three variables correlate with good red teaming. First, personality traits: successful red teamers are quick-thinking, adaptive, self-motivated, and fearless in pursuing truth, yet curious and willing to learn. Rodney Faraon, former CIA analyst, notes they're "like method actors" who internalize adversaries' motives and values. They must balance skepticism with finesse-as Marissa Michel explains, "You can have great ideas, but if you are crotchety nobody will pay attention to you." Second, red teamers often aren't career "climbers"-they prioritize speaking truth over being team players. Military "terminal colonels" no longer seeking promotion make excellent red teamers because they'll speak honestly. Third, experience matters: the best red teamers are widely read (especially in history), have held multiple positions, and communicate exceptionally well through storytelling rather than dry presentations. Many have witnessed large systemic failures firsthand, helping them envision future vulnerabilities. The UK Ministry of Defence's red team found that effective red teamers often possess "a fringe effect of minor autism"-logical thinkers who may lack social awareness but can identify flaws others miss. This explains why hackers and security professionals often excel at red teaming; they naturally think about how systems can be subverted. Red teaming skills can be taught through courses like those at the University of Foreign Military and Cultural Studies, which focus on metacognition-thinking about thinking. However, some people simply cannot be red teamers, lacking the ability to fully embrace the adversarial mindset. Most red teamers serve in the role temporarily (1-2 years) to avoid becoming captured by institutional biases. The ultimate goal is to "infect" the organization with red teaming approaches, creating mini-red teamers who carry these skills back to their regular positions.

Capítulo 6

Have a Big Bag of Tricks: Keeping Red Teams Effective

Effective red teamers must be eclectic and broad-minded, with a diverse toolkit that prevents their work from becoming routine or predictable. When red team approaches become anticipated, they're easily subsumed into an institution's normal processes, losing their disruptive value. Smart red teamers never reveal all their tactics during initial engagements. As retired Marine Colonel Mark Monroe advises: "Never show all your cards, and always leave them wanting more." They must remain flexible, ready to adapt techniques mid-engagement when initial approaches fail to gain traction. NYPD Counterterrorism Bureau chief James Waters, who runs commissioner's tabletop exercises, emphasizes: "Don't fight the scenario." During simulations, if participants anticipate consequences and propose correct responses, Waters immediately introduces new unexpected challenges rather than rigidly following the script. The best red teamers also demonstrate self-awareness and humility by recognizing unsuccessful engagements and learning from them. The military employs highly realistic simulations to prepare service members for overseas deployments. These range from tabletop exercises to elaborate war games like Millennium Challenge 2002, a $250 million exercise involving 13,500 service members. In this exercise, retired Marine Lieutenant General Paul Van Riper, leading the opposition force, used unconventional tactics to sink nineteen virtual U.S. ships including an aircraft carrier in the opening minutes-demonstrating the dangers of untested military concepts. In the private sector, Benjamin Gilad conducts business war games through moderated discussions rather than data-driven simulations because "the second you put numbers into a computer, you move from reality to fantasy." He uses Porter's Four Corners Model to force executives to assume competitors' roles by wearing their logo shirts and handling their products. This helps them understand rivals' likely responses to strategic decisions. As facilitator, Gilad's role is "to call bullshit on everybody in the room, especially the executives," reminding them, "I am the market and I want to save your jobs." Technology increasingly enhances the red teamer's toolkit. Army Brigade Combat Teams in Afghanistan conducted "honesty analyses" of Afghan security patrols by comparing commander reports with GPS tracking data. Business strategist Mark Chussil builds complex quantitative simulations to predict competitor reactions to different strategic options. Law firms employ computer simulations from consultancies like Lex Machina to model potential litigation outcomes. However, these technologies remain pointless without humans who can flexibly apply them and translate findings into actionable insights for the targeted institution.

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Capítulo 7

Be Willing to Hear Bad News and Act on It: The Hardest Part

For red teaming to succeed, findings and recommendations cannot simply collect dust on shelves-they must be heard and implemented to the extent the boss deems possible. Organizations sometimes try to avoid uncomfortable findings by "gaming" engagements-denying information access to analysts, increasing security during vulnerability probes to ensure defense "succeeds," or taking systems offline during penetration tests to avoid exposure. Every red teamer has stories of leaders who stubbornly denied shortcomings even after they were exposed. One white-hat hacker reported identifying the same network vulnerability at a Fortune 100 technology firm for over a decade, with the company repeatedly ignoring recommendations to fix it. In such cases, the institution is merely going through motions without learning or improving. This resistance to bad news explains why the FAA's pre-9/11 red team saw no evidence of meaningful corrective action despite documenting serious security failures. It explains why the Marine Corps red team in Afghanistan (2011) was "almost entirely marginalized"-referred to as "kids at the card table at Christmas." It explains why a Marine colonel who bluntly presented critical findings about Afghan partnerships to General Stanley McChrystal was rebuffed with "It sounds like you're telling me how to run my war." The targeted institution needs absorptive capacity to implement red team findings, which might require additional funding, personnel changes, or painful adjustments to standard procedures. A monitoring process should track implementation progress. Red team exercises that are conducted but ignored can be worse than none at all, as leadership falsely believes their systems were properly scrutinized. In 2010, McKinsey was hired to "pressure test" the ObamaCare rollout and warned of likely glitches six months before launch, but their findings were disregarded, resulting in a political disaster. The challenge for red teams is operating successfully within an institution while maintaining independence to challenge it-existing in a sweet spot between institutional capture and irrelevance. As health expert Gregory Pirio noted, effective red teamers resemble ronin samurai who were "free to tell the shogun that he was an idiot" because they were "de-institutionalized."

Capítulo 8

Red Team Just Enough, But No More: Finding the Right Frequency

Calibrating the frequency of red teaming is crucial-too much can be as problematic as too little. For institutions facing scheduled events or consequential decisions, a one-time red team effort may suffice, like the alternative analyses used to assess probabilities that Osama bin Laden was in Abbottabad in 2011. For ongoing operations, excessive red teaming prevents institutions from implementing previous recommendations. As James N. Miller puts it: "You can't red team everything to death, or else you won't get anything done. But for big important projects, getting independent eyes on it can be invaluable." Military red teamers use the acronym GICOT-"Good Idea Cut Off Time"-to know when to conclude their efforts. Frequent testing can demoralize employees who feel constantly scrutinized. It can build walls of mistrust between staff and red teamers. And red teams that cry wolf too often lose credibility-as Robert Gates noted, "You only have to be wrong three times in a row for people to stop paying attention to you." Conversely, too infrequent red teaming breeds complacency. The optimal frequency depends on how dynamic an institution's environment is. Ben Gilad recommends multinational companies commission external analyses every five years, while nuclear facilities require force-on-force inspections every three years, and companies facing persistent cyber threats might need quarterly penetration tests. The cyber penetration testing process illustrates this challenge. White-hat hackers almost always gain unauthorized access, typically through human error like default passwords or successful phishing attacks. They deliver reports with prioritized corrective actions, but organizations typically fix only about three-quarters of severe vulnerabilities and rarely address less critical ones. This creates what one expert calls "cybersecurity on a hamster wheel"-a frustrating cycle where the same vulnerabilities reappear in subsequent tests. At a 2014 conference, not one of 300 security professionals reported having adequate resources or personnel to protect their networks. The overarching best practice is flexibility in adapting best practices. Red teamers resist dogma because it contradicts effective red teaming. Red teaming is more art than science-neither abstract expressionism nor paint-by-numbers, but somewhere between, unique to each red teamer's background and skills. Success depends on both the red team and the targeted institution playing their respective roles in implementing these interrelated best practices.

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Capítulo 9

The Future of Red Teaming: Beyond the Hype

Red teaming has become both "oversold and under-appreciated at the same time," according to Mark Mateski, founder of the Red Team Journal. The term itself has become trendy, with security firms rebranding standard penetration testing as "red teaming" to command higher fees. Chris Nickerson, a prominent security professional, notes his company rarely uses the term publicly anymore because "it has become so co-opted by so many people." Despite these challenges, red teaming inevitably produces one of two valuable outcomes. First, it delivers novel insights that couldn't have emerged organically within the institution. The structural elements that make organizations function smoothly-hierarchy, formal rules, unit cohesion, behavioral norms-are precisely what inhibit creative thinking. Properly resourced red teams overcome these limitations. Second, even when red teaming fails to impact an organization, it reveals something about that institution's thought processes and values. Failures typically stem from leaders believing red teaming is unnecessary because they would already know about problems or their employees would tell them-both dangerously flawed assumptions. Red teams should challenge conventional wisdom, identify blind spots, reveal vulnerabilities, and consider worst-case scenarios-but they should never make final decisions. Though it might be tempting for leaders to delegate decision authority to red teams, especially amid partisan gridlock, this fundamentally misunderstands their purpose. The future of red teaming depends on maintaining a balanced view of its utility. Red teams make a demonstrable difference when properly structured and empowered, helping leaders process complex information and make consequential decisions. However, they have limitations and shouldn't replace an institution's planning components. Red teaming isn't a cure-all but rather a conceptual approach with specific tactics for particular challenges. As retired Lieutenant Colonel William "Razz" Rasgorshek explains using an analogy from his combat pilot experience: Just as night vision goggles create blind spots that pilots must compensate for by scanning side-to-side, "there are certainly blind spots in our brains. It is a matter of educating people how blind spots develop, showing them that they exist, and then educating them so they can practice in order to control the interference of the blind spots. That is what red teaming can do."

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Temas principais em Equipe Vermelha

adversarial thinking
institutional blind spots
structured dissent
vulnerability assessment
cognitive bias mitigation

Citações de Equipe Vermelha

What happened on 9/11 was a system designed for failure.
You cannot grade your own homework.
Incompetence breeds overconfidence.
Your ability to mind read is more praiseworthy than your ability to think critically.
Unless the commanders themselves want it...it won't matter.

Personagens de Equipe Vermelha

Micah ZenkoAuthor and investigator of red teaming practices
Paul Van RiperRetired Marine Lieutenant General
Thorstein VeblenEconomist who observed institutional capture

Sobre o Autor

Micah Zenko, autor de Red Team: How to Succeed By Thinking Like the Enemy, é um especialista em segurança nacional e membro sênior da Chatham House, renomado por seu trabalho em tomada de decisões estratégicas e prevenção de conflitos. Doutor pela Brandeis University, a carreira de Zenko abrange funções no Belfer Center de Harvard, no Departamento de Estado dos EUA e no Council on Foreign Relations, onde sua pesquisa se concentrou em operações militares e avaliação de riscos.

Seu livro inovador, que mistura estratégia de negócios e estudos de segurança, baseia-se em mais de 250 entrevistas com líderes em inteligência, contraterrorismo e setores corporativos para revelar como o pensamento adversarial pode transformar o planejamento organizacional.

As obras anteriores de Zenko incluem Between Threats and War: U.S. Discrete Military Operations in the Post-Cold War World, analisando a estratégia militar, e Clear and Present Safety, em coautoria com Michael A. Cohen, que desafia equívocos sobre a segurança global. Como Diretor de Pesquisa e Aprendizado no McChrystal Group, ele assessora organizações em metodologias de red teaming para antecipar vulnerabilidades. Colaborador frequente do The Atlantic, Foreign Policy e The Guardian, as percepções de Zenko são citadas tanto por formuladores de políticas quanto por executivos da Fortune 500. Red Team é amplamente utilizado por planejadores militares e líderes corporativos, consolidando a reputação de Zenko como a principal autoridade em desafiar suposições institucionais.

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@Cashflowbubu

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@Chloe, Solo founder, LA

117

"Perfect balance between learning and entertainment. Finished ‘Thinking, Fast and Slow’ on my commute this week."

@Raaaaaachelw

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@Matt, YC alum

108

"Reading used to feel like a chore. Now it’s just part of my lifestyle."

@Erin, Investment Banking Associate , NYC

254

"Feels effortless compared to reading. I’ve finished 6 books this month already."

@djmikemoore

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@SofiaP

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@Jaded_Falcon

201

"It is great for me to learn something from the book without reading it."

@OojasSalunke

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@Leo, Law Student, UPenn

483

"Makes me feel smarter every time before going to work"

@Cashflowbubu

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1,000,000+ curious minds.

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Um livro. Muitas maneiras de ouvi-lo.

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