There’s a reason the world is obsessed with how the ultra-wealthy think: money buys power, influence, and a lifestyle most of us can’t fathom.
But what if the real story isn’t about mansions and yachts? What if it’s about the mindset that propels people to the top—and keeps them there, often at the expense of others?
Here are 16 books that pull back the curtain on the dark, ruthless, and sometimes morally ambiguous strategies the affluent use to stay ahead.
1. The Richest Man in Babylon by George S. Clason
Don’t let the ancient Babylonian setting fool you—this book’s lessons about wealth accumulation are as ruthless as they are timeless. While it masquerades as simple parables about saving and investing, the underlying message is darker: those who don’t follow these “laws” deserve their poverty. The book essentially argues that financial success is a moral imperative, and those who fail to achieve it are simply weak or undisciplined. What’s particularly unsettling is how it frames helping others—unless you’ve secured your wealth first, any generosity is painted as foolishness rather than kindness.
The book’s most chilling advice might be its insistence on paying yourself first, regardless of your obligations to others. Sure, it’s solid financial advice, but the complete lack of nuance about life circumstances reveals a worldview where misfortune is always self-inflicted.
2. Think and Grow Rich by Napoleon Hill
Napoleon Hill spent 20 years studying the wealthiest Americans of his time, and what he discovered wasn’t just a success formula—it was a blueprint for obsession that borders on the pathological. The book’s central premise, that thoughts can materialize into riches through sheer force of will, sounds empowering until you realize it implies that poverty is essentially a choice. Hill’s philosophy suggests that anyone who isn’t rich simply isn’t thinking hard enough, completely dismissing systemic barriers, discrimination, or plain bad luck.
What’s even darker is the book’s treatment of failure and adversity. Hill frames every setback as a “blessing in disguise” that separates the worthy from the unworthy—a convenient philosophy for those already at the top looking down.
3. Rich Dad Poor Dad by Robert Kiyosaki
Kiyosaki’s blockbuster hit presents two worldviews: his “poor dad” (his actual father, an educated government employee) and his “rich dad” (a friend’s father who became wealthy). But beneath the surface of financial education lies a disturbing contempt for traditional employment and those who choose it. The book essentially argues that having a job makes you a sucker, that paying taxes is for chumps who don’t know better, and that financial manipulation is not just acceptable but admirable.
Perhaps most troubling is how the book encourages readers to view relationships transactionally. Kiyosaki advocates surrounding yourself only with those who can advance your financial goals, essentially reducing human connections to potential revenue streams.
4. The 48 Laws of Power by Robert Greene
If there’s one book that lays bare the Machiavellian mindset of power-seekers, it’s this one. Greene doesn’t just describe power tactics; he celebrates manipulation, deception, and ruthlessness as virtues. Each “law” reads like a masterclass in sociopathy: crush your enemies completely, use others’ work but take the credit, play on people’s need to believe to create a cultlike following. This isn’t just a book about power—it’s a manual for those who believe that morality is a luxury they can’t afford.
What makes it particularly dark is its matter-of-fact tone, as if destroying others for personal gain is as natural as breathing. There’s no consideration of ethics, no discussion of whether these tactics should be used—just cold, calculated strategies for domination.
5. Atlas Shrugged by Ayn Rand
Rand’s magnum opus isn’t just a novel—it’s a 1,200-page manifesto declaring selfishness as the highest virtue. The story of industrialists going on strike might seem like fiction, but its philosophy has influenced countless wealthy individuals who see themselves as the “producers” carrying ungrateful “parasites” on their backs. The book’s core message is chilling: altruism is evil, and those who can’t produce value deserve to perish.
What’s most disturbing is how the book dehumanizes anyone who isn’t a captain of industry. The poor, the disabled, the unlucky—they’re all painted as leeches who deserve their fate. In Rand’s world, compassion isn’t just weakness; it’s a moral failing.
6. The Millionaire Next Door by Thomas J. Stanley and William D. Danko
This book shatters the flashy millionaire stereotype, but what it reveals instead is arguably more disturbing. Through extensive research, Stanley and Danko discovered that most millionaires live like misers, obsessing over every penny while maintaining ordinary facades. The dark truth? These millionaires view spending on anything beyond the bare necessities, including their own families, as a weakness. The book glorifies extreme frugality to the point where denying your children experiences or opportunities becomes a virtue, as long as it preserves wealth. One particularly chilling chapter details how wealthy parents deliberately keep their adult children financially dependent to maintain control, all while preaching self-reliance.
What’s most unsettling is the book’s underlying message: true wealth requires sacrificing not just luxuries, but often relationships and life experiences. The millionaires profiled measure success purely in net worth, viewing those who enjoy their money as failures who lack discipline.
7. The Wealth of Nations by Adam Smith
While often celebrated as the foundation of modern economics, Smith’s masterwork contains some deeply troubling ideas about human worth and social hierarchy. The “invisible hand” concept sounds benign until you realize it’s used to justify letting the poor starve because market forces deem them expendable. Smith’s vision of capitalism treats workers as mere cogs in a machine, arguing that their suffering is necessary for economic efficiency. He describes how dividing labor makes workers stupider and more machine-like, yet presents this as progress.
The book’s most disturbing aspect is how it reduces all human interaction to market transactions. Compassion, community, culture—all become inefficiencies to be eliminated in pursuit of wealth accumulation. Smith’s work laid the intellectual foundation for every wealthy person who’s ever said “it’s just business” while destroying lives.
8. The Prince by Niccolò Machiavelli
Though written for political rulers centuries ago, this book has become required reading in business schools and boardrooms worldwide. Machiavelli’s advice—it’s better to be feared than loved, cruelty can be merciful if used correctly, and deception is essential to power—reveals why so many wealthy individuals seem sociopathic. The book doesn’t just permit immoral behavior; it argues that refusing to be ruthless makes you unfit to lead. Modern billionaires have internalized these lessons, viewing kindness as something to fake when useful but never genuinely feel.
What makes The Prince particularly dark is its complete separation of success from virtue. Machiavelli teaches that maintaining power justifies any action, from betraying allies to crushing the innocent. It’s a playbook for those who sleep soundly after ruining lives because they’ve convinced themselves it was necessary.
9. The Fountainhead by Ayn Rand
While Atlas Shrugged gets more attention, Rand’s earlier novel might be even more revealing about wealthy mindsets. The story of architect Howard Roark teaches that genius justifies any behavior, including terrorism—Roark bombs a building because others modified his design. The book’s message is clear: if you’re talented enough, rules and other people’s rights don’t apply to you. This philosophy resonates deeply with tech billionaires and financial titans who believe their wealth proves their superiority.
The book’s treatment of relationships is particularly toxic. Love becomes another form of transaction where emotional manipulation is reframed as strength. Characters who show genuine care for others are portrayed as weak and contemptible, while those who use and discard people are the heroes.
10. Zero to One by Peter Thiel
Thiel’s startup manual reveals more than just business strategy—it exposes a worldview where monopolistic dominance isn’t just good business, it’s a moral imperative. The book explicitly argues against competition, teaching entrepreneurs to crush rivals and create monopolies because shared prosperity is for losers. Thiel’s philosophy is that truly successful people don’t improve existing systems; they create new ones where they alone hold power.
What’s most chilling is the book’s vision of the future: a world divided between a tiny elite who control revolutionary technology and everyone else who becomes increasingly irrelevant. Thiel doesn’t see this as a problem to solve but as the natural order. His advice essentially boils down to: be the one doing the replacing, not the one being replaced, with zero concern for those left behind.
11. How to Win Friends and Influence People by Dale Carnegie
Carnegie’s classic might seem like harmless self-help, but scratch beneath its friendly surface and you’ll find a manual for sophisticated manipulation disguised as social skills. The book teaches readers to feign interest in others purely to extract what they want, to never tell someone they’re wrong even when they are, and to make people feel important only to control them. While Carnegie frames these as ways to be “likeable,” wealthy readers have weaponized these tactics to build networks of people who don’t realize they’re being used. The darkest chapter might be the one on making people glad to do what you want—essentially, psychological manipulation rebranded as leadership.
What’s particularly insidious is how the book has normalized fake empathy in business culture. Countless executives have learned to mirror emotions they don’t feel and express concern they don’t have, all while viewing human connections as tools for advancement. Carnegie created a playbook for those who see authenticity as inefficiency.
12. The Art of War by Sun Tzu
This ancient military treatise has become required reading in business schools and corporate boardrooms, and for disturbing reasons. Modern wealthy elites don’t just see business as war-like—they see it as actual war, where destroying “enemies” is not just acceptable but necessary. Sun Tzu’s teachings about deception, using spies, and attacking where the enemy is weakest have been adapted to justify corporate espionage, hostile takeovers, and crushing smaller competitors. The book’s philosophy that “all warfare is based on deception” has given moral cover to those who lie and cheat their way to fortune.
The most chilling application is how the wealthy use Sun Tzu’s strategies against their employees and partners. Concepts like “know your enemy” become “maintain files on everyone,” and “divide and conquer” justify keeping workers fighting each other instead of organizing for better conditions.
13. The Lean Startup by Eric Ries
While marketed as an innovation methodology, this book reveals a dark truth about how modern wealth is created: through rapid experimentation on users who become unwitting test subjects. The “fail fast” philosophy sounds progressive until you realize it means treating people’s data, privacy, and sometimes safety as acceptable casualties in the pursuit of market fit. Ries’s framework has been used to justify launching half-baked products that harm users because hey, it’s just an “experiment.”
What’s truly disturbing is the book’s complete disconnection from human consequences. Everything is reduced to metrics and pivot decisions, while real people affected by these “experiments” become mere data points. This thinking has enabled tech billionaires to test addictive features on children, experiment with democracy through social media, and disrupt entire industries without considering the human wreckage left behind.
14. Good to Great by Jim Collins
Collins studied companies that made the leap from good to great, but what he uncovered—and celebrates—is often brutal. The book’s concept of “getting the right people on the bus and the wrong people off” sounds reasonable until you see how it’s applied: mass layoffs reframed as “upgrading talent” and a culture where human beings are disposable if they don’t fit the vision. The book lionizes CEOs who ruthlessly cut anything that doesn’t contribute to greatness, including loyal employees who built the company.
Most disturbing is the book’s “Hedgehog Concept”—the idea that great companies focus monomaniacally on one thing. In practice, this has justified destroying communities through outsourcing, eliminating product lines people depend on, and abandoning any social responsibility that doesn’t directly drive profits. Collins presents sociopathic focus as wisdom.
15. The 4-Hour Workweek by Tim Ferriss
Ferriss’s lifestyle design manifesto reveals an ugly truth about wealth: it’s often built on exploiting global inequality and outsourcing your problems to people desperate enough to handle them cheaply. The book teaches readers to hire virtual assistants in developing countries for pennies on the dollar, to automate away human interaction, and to view traditional work as something only suckers do. What Ferriss presents as “lifestyle design” is a guide to joining the global elite by stepping on everyone else.
The book’s darkest element is its complete moral vacuum regarding the externalities of this lifestyle. Those virtual assistants working for $3/hour? Are the customers dealt with by automated systems? The colleagues left to pick up your slack? They’re not people—they’re inefficiencies to be optimized away. Ferriss created a blueprint for narcissistic wealth that sees other humans as obstacles to your beach vacation.
16. Sapiens by Yuval Noah Harari
While not explicitly about wealth, this book has become a favorite among tech billionaires for disturbing reasons. Harari’s sweeping history of humanity reduces everything—religion, human rights, nations—to “shared fictions” that only matter if people believe in them. For the wealthy, this becomes justification for reshaping society according to their vision because hey, it’s all made up anyway. The book’s discussion of how agriculture was “history’s biggest fraud” resonates with elites who see most human progress as mistakes they’re destined to correct.
What’s most chilling is how billionaires have interpreted Harari’s work as permission to play god. If human rights are just stories we tell ourselves, then why not rewrite them? If consciousness might be hackable, why not be the one doing the hacking? Harari’s academic observations become blueprints for those who believe their wealth gives them the right to redesign humanity itself.
