Michael Saylor, executive chairman of Strategy and a corporate Bitcoin advocate, has released a 38-book leadership curriculum called “Upgrade the World,” laying out a reading program for decision-makers in business, politics, finance, and technology.
The list stretches across history, war, economics, political philosophy, energy, technology, and money. It begins with Will Durant’s civilizational history, runs through Jared Diamond’s geographic framework, John Keegan and Livy on war, Nassim Nicholas Taleb’s writing on uncertainty, and Murray Rothbard’s Austrian economics, then closes with energy, digital technology, and Bitcoin. The endpoint is Saifedean Ammous’ The Bitcoin Standard and Satoshi Nakamoto’s Bitcoin white paper.
From MIT and enterprise software to Bitcoin
Saylor said his education and career have revolved around one question: how technology can improve the human condition.
He studied science, technology, and society at the Massachusetts Institute of Technology, founded the enterprise software company MicroStrategy, wrote the technology trends book The Mobile Wave, and later came to view Bitcoin as a technology that can store and transmit “economic energy.”
Out of those experiences, Saylor says human prosperity cannot rest on goodwill alone. In his framing, it depends on scientific knowledge, engineering, energy, capital, markets, property rights, and effective institutions working together. He summarizes the basic conditions of civilization as “clean air, clean water, clean food, clean energy, and clean money.”
Institutions, in his view, need enough order to protect life, property, and contracts. They also need enough freedom to allow experimentation, competition, and creative destruction. Too little order leads to violence and disorder; too much suppresses creativity and drifts toward tyranny. Prosperity sits between those poles, in a market order that can coordinate billions of people without erasing individual autonomy.
Saylor argues that modern leaders often repeat similar mistakes: launching wars they cannot win, creating rules that cannot be followed in practice, mistaking luck for skill, treating propaganda as knowledge, and optimizing systems so aggressively for efficiency that they become fragile.
He also points to the misuse of scarce energy and capital by governments and companies, the forced maintenance of inefficient systems that survive only through power, and the suppression of human creativity in the name of administration. Group psychology is part of the course as well. Leaders can be swept up by mass fervor, or place themselves directly in front of a social force that can no longer be stopped. Saylor says the goal is not ideological conformity. It is judgment.
That judgment, he says, requires long historical memory, a theory of human action, respect for uncertainty, a clear understanding of violence and power, and the ability to track changes in capital, energy, and technology. It also requires knowing whether a technology has durable value or is only a fashionable narrative.
Starting with civilizational memory
The largest share of the course is devoted to Will and Ariel Durant’s 11-volume The Story of Civilization and the shorter The Lessons of History. Together, they account for close to one-third of the full program.
The Story of Civilization spans Asia and the ancient Near East, Greece, Rome, the Middle Ages, the Renaissance, the Reformation, the Enlightenment, the French Revolution, and the Napoleonic era. Saylor says the importance of the Durants lies less in perfect alignment with every point of modern scholarship than in the scale of observation. They place religion, family, commerce, banking, war, philosophy, technology, law, art, institutions, and individuals inside a time frame measured in centuries.
Within that structure, ideas become institutions, institutions accumulate power, prosperity produces more complex social orders, and success can breed complacency along with capability. Saylor recommends reading The Lessons of History first as a map for the broader course, then reading it again after finishing the full sequence.
How far geography can explain outcomes
After civilizational history, Saylor includes Jared Diamond’s Guns, Germs, and Steel, which examines why societies diverged so widely in wealth, military power, technology, and political organization. Diamond emphasizes geography, climate, food production, domesticable plants and animals, disease exposure, population density, the orientation of continents, and the spread of technology.
Saylor says that framework reminds leaders not to overestimate willpower while underestimating inherited conditions. Countries do not choose their geography, river systems, disease environments, or natural resources, and those facts shape population, trade, military organization, institutions, and the spread of knowledge.
At the same time, he says Guns, Germs, and Steel should not be treated as a complete theory of causation. Geography affects history, but it does not write history by itself. Human agency, institutions, culture, leadership, ideology, and property rights still matter.
War, Rome, and political resilience
For war and strategy, Saylor recommends John Keegan’s A History of Warfare and surviving portions of Livy’s history of Rome.
He offers a simple rule: do not start a war you cannot win, cannot finance, cannot control, and cannot end on acceptable terms. He describes war as a machine that consumes lives, energy, capital, legitimacy, information, and time, often producing second-order effects that the initiator did not foresee.
The Second Punic War is one of the cases he emphasizes most. Hannibal repeatedly defeated Roman armies and threatened the survival of the Roman Republic, yet Rome endured through its political institutions, manpower mobilization, alliance structure, strategic depth, and capacity to absorb extraordinary losses. For Saylor, that distinction captures the gap between battlefield genius and civilizational capability. Tactical brilliance matters, but long-term survival depends on whether institutions can absorb disaster, learn from failure, and adapt.
Taleb’s Incerto and the problem of fragility
The fourth section of the program is Nassim Nicholas Taleb’s five-book Incerto series: Fooled by Randomness, The Black Swan, The Bed of Procrustes, Antifragile, and Skin in the Game.
Saylor reduces Taleb’s central argument to one question: not whether a forecast is correct, but how much exposure exists when it is wrong. If the future cannot be predicted with precision, then the rational response is not a more elaborate forecasting model. It is to cap ruin risk, preserve optionality, encourage distributed experimentation, and let systems learn from small failures.
Fooled by Randomness deals with the confusion of luck and skill. The Black Swan looks at how low-probability, high-impact events dominate history. Antifragile shifts the issue from prediction to design, arguing for systems that grow stronger through volatility, stress, and error.
Saylor says many highly optimized systems look efficient in ordinary times but reveal that every layer of resilience has been stripped out once a shock hits. In his phrasing, “efficiency without survivability is just hidden fragility.”
Rothbard as the theoretical spine
Among all the authors on the list, Saylor places libertarian economist Murray Rothbard at the theoretical center of the course. He calls Rothbard the program’s “theoretical spine” and recommends Man, Economy, and State, Power and Market, The Ethics of Liberty, An Austrian Perspective on the History of Economic Thought, and the five-volume Conceived in Liberty.
Rothbard starts from purposeful human action and builds out discussions of value, exchange, prices, production, capital, interest rates, money, banking, business cycles, and government intervention. Saylor highlights one point in particular: rules do not eliminate the incentives and scarcity they ignore. They redirect behavior into avoidance, substitution, black markets, corruption, or institutional failure.
Still, he says Rothbard should be read critically, not treated as doctrine. He suggests placing Rothbard’s critique of government and constitutional systems alongside the strongest arguments for constitutional government, federal authority, and institutional checks and balances, including The Federalist Papers and Alexis de Tocqueville’s Democracy in America.
Saylor says Rothbard’s greatest strength is theoretical consistency. That is also why readers need to test whether his historical explanations, political inferences, and rhetoric simplify reality too much.
Rockefeller, Morgan, and what capital really is
For business and institutional power, Saylor turns to Ron Chernow’s Titan and The House of Morgan, one focused on industrial capital, the other on financial capital.
Titan traces John D. Rockefeller and the rise of Standard Oil through vertical integration, operating discipline, logistics, accounting, pricing, competition, monopoly, reputation, and public legitimacy. Saylor says Rockefeller did more than accumulate assets. He built an integrated system that reduced costs, set standards, coordinated infrastructure, and outlasted rivals over time. The same discipline that produced extraordinary efficiency also concentrated economic power.
The House of Morgan follows the Morgan banking dynasty and the formation of the modern financial system, showing the relationship among banks, corporations, governments, central banking, war, regulation, and financial crises. Saylor argues that capital is not just money. It is trust, knowledge, competence, organization, relationships, reputation, information, and productive capacity accumulated over long periods.
Energy, knowledge, and technology
In the energy and technology section, Saylor recommends Daniel Yergin’s The Prize, David Deutsch’s The Beginning of Infinity, and his own The Mobile Wave.
The Prize uses the history of oil to show how energy shapes industrialization, transport, war, national power, business organization, and the global economy. Saylor says modern civilization rests on abundant energy. Agriculture, manufacturing, sanitation, transport, communications, computing, defense, and urban life all depend on humanity’s ability to convert energy into useful work. Even financial and digital systems remain grounded in the physical world.
Deutsch’s The Beginning of Infinity represents the knowledge side of the framework. The book argues that new solutions can keep emerging if societies allow conjecture, experimentation, criticism, and error correction.
Within Saylor’s scheme, energy represents the capacity to act, knowledge represents the capacity to imagine, and technology turns knowledge into scalable capability. Markets and institutions determine whether those capabilities are used effectively, suppressed, monopolized, or weaponized.
Why Saylor included The Mobile Wave
Saylor also placed his own 2012 book The Mobile Wave as the 37th core text. He said he was “somewhat hesitant” to include it, but considered it useful as an experiment in technology forecasting.
The book attempts a first-principles analysis of what happens when computing becomes mobile, software dematerializes products and services, and billions of people remain connected to networked intelligence. It examines the effects on education, commerce, media, payments, healthcare, transportation, employment, and corporate structure.
Saylor says readers should not treat the book as authority. They should treat it as a record of forecasts that can be checked against what followed: which calls were right, which were incomplete, and which second-order effects were missed.
For him, the key to technology forecasting is not guessing a specific device. It is recognizing a new capability, understanding its economic edge, and then tracking what happens when that capability spreads at scale in a competitive society. Digital transformation often does more than make old institutions run faster. It can dematerialize them, redistribute power, alter economic models, and eventually create a very different system.
The final stop: The Bitcoin Standard and the Bitcoin white paper
The final core book in the course is Saifedean Ammous’ The Bitcoin Standard. Saylor treats air, water, food, and energy as conditions for biological life, and money as the tool that coordinates economic life. On that view, civilization needs “clean money” capable of preserving the economic energy created by labor, creativity, and capital across time and space.
He argues that when a monetary system breaks down, prices, contracts, investment, and all long-term calculation are affected. The Bitcoin Standard moves from shells, stones, metals, coins, gold, paper claims, and state money to digital money, asking what qualities let a good carry value across time and distance. The book presents Bitcoin as a scarce-supply, global, decentralized digital hard money governed by protocol rather than political discretion.
Saylor says the book’s main value is its monetary analysis, while some of its cultural and social conclusions should be treated as the author’s claims rather than universal laws. He recommends reading Rothbard first for money and political power, then Yergin for energy, Deutsch for knowledge, and The Mobile Wave for digital transformation before arriving at The Bitcoin Standard.
After that, he says, readers should go directly to Satoshi Nakamoto’s original white paper. Commentary can provide context, but engineers, in his words, ultimately have to return to the specification, the code, and the machine in operation.
Read every author adversarially
Even with the course’s strong point of view, Saylor repeatedly tells readers to adopt what he calls “adversarial reading.” Durant should be checked against modern historical scholarship. Diamond should be balanced with institutions, culture, and human agency. Keegan should be read against Clausewitz. Livy should be separated from modern historical method.
Rothbard should face the strongest arguments for constitutional government and public authority. Taleb’s skepticism should itself be questioned. The capitalists in Chernow’s books should be studied, not worshiped.
Yergin’s history of energy should not be mistaken for a guarantee that the future will replay the past. Deutsch’s optimism about progress depends on institutions that permit criticism and correction. The Mobile Wave should be checked against the world that actually emerged. The Bitcoin Standard should be compared with the white paper, the code, the live network, monetary history, and competing theories of money.
Saylor says readers should ask three questions of every work in the program: what does this framework see that others miss, where does it oversimplify reality, and if it is correct, which decisions would need to change?
This article first appeared on ABMedia.