Books that fundamentally changed how I think. Each challenged my assumptions and opened up new ways of seeing the world that continue to influence me today.

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  The Cause — The American Revolution and its Discontents, 1773-1783
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  The Machiavellians — Defenders of Freedom
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  Modernity without Restraint — The Political Religions; The New Science of Politics; and Science, Politics, and Gnosticism
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  Benjamin Franklin — An American Life
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  The History of the Ancient World — From the Earliest Accounts to the Fall of Rome
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  Elon Musk
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  The Ancient City — A Study on the Religion, Laws, and Institutions of Greece and Rome
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  Leonardo da Vinci
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  How to Build a Car — The Autobiography of the World's Greatest Formula 1 Designer
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  One Hundred Years of Solitude
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  Steve Jobs
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  The Tinkerings of Robert Noyce — The Man Behind the Microchip
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  Seeing Like a State — How Certain Schemes to Improve the Human Condition Have Failed
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  The Dream Machine — J.C.R. Licklider and the Revolution That Made Computing Personal
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  The Sovereign Individual — Mastering the Transition to the Information Age
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  The Beginning of Infinity — Explanations That Transform the World
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  Surely You're Joking, Mr Feynman
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  Softwar — An Intimate Portrait of Larry Ellison and Oracle
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  Ashlee Vance's Elon biography
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  The Mythical Man-Month — Essays on Software Engineering
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  Mindstorms — Children, Computers, and Powerful Ideas
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  Masters of Doom — How Two Guys Created an Empire and Transformed Pop Culture
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  Skunk Works — A Personal Memoir of My Years at Lockheed
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  Structure and Interpretation of Computer Programs
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  Thinking in Systems — A Primer
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  Superintelligence — Paths, Dangers, Strategies
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  The Whole Earth Catalog
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  Zero to One
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  The Hard Thing about Hard Things
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  Founders at Work — Stories of Startups' Early Days
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  Showstopper — The Breakneck Race to Create Windows NT
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  Dealers of Lightning — Xerox PARC and the Dawn of the Computer Age
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  The Making of the Atomic Bomb
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  PG's essays — Hackers & Painters
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  The Rise and Fall of American Growth
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  The Big Score — The Billion Dollar Story of Silicon Valley
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  Finite and Infinite Games — A Vision of Life as Play and Possibility
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  A Pattern Language — Towns, Buildings, Construction
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  The Selfish Gene
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  The Lean Startup
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  Marginal Revolution (if it has to be a book, Stubborn Attachments)
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  Revolution in the Valley — The Insanely Great Story of How the Mac Was Made
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  Uncanny Valley — A Memoir
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  LessWrong — Rationality: From AI to Zombies
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  Slate Star Codex(/ACT)
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  The PayPal Wars — Battles with eBay, the Media, the Mafia, and the Rest of Planet Earth
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  The Cathedral and the Bazaar — Musings on Linux and Open Source by an Accidental Revolutionary
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  The Diamond Age — Or, A Young Lady's Illustrated Primer
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  What the Dormouse Said — How the Sixties Counterculture Shaped the Personal Computer Industry
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  Zen and the Art of Motorcycle Maintenance
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  The Rise of Theodore Roosevelt
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  Titan (on Rockefeller)
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  The Power Broker — Robert Moses and the Fall of New York
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  Gödel, Escher, Bach — An Eternal Golden Braid