Episode · The Daily Stoic · 2026-10-16
Books mentioned on Inside Ryan Holiday’s $250K Reading List
You could spend a lot of time and money earning an MBA, or you could start with these books that will change how you think about business, leadership, and success. Watch this episode on Ryan Holiday's YouTube channel: https://www.
Ryan Holiday recommended Meditations by Aurelius Marcus, Trillion-dollar Coach by Eric Schmidt and others, What I Learned Losing a Million Dollars by Jim Paul and others, Billion Dollar Lessons by Paul Carroll and others, How I Built this by Guy Raz and others, Good to Great by Jim Collins, Unreasonable Hospitality by Will Guidara, Zero to One by Peter A. Thiel and others, The 22 Immutable Laws of Marketing by Al Ries and others, The $100 startup by Chris Guillebeau, The Lean Startup by Eric Ries, Thinking in Bets by Annie Duke, The Hard Thing About Hard Things by Ben Horowitz, Essentialism by Greg McKeown, The 33 Strategies of War by Robert Greene and others, The 48 Laws of Power by Robert Greene and others, Mastery by Robert Greene, The Laws of Human Nature by Robert Greene, The Art of Seduction by Robert Greene and others, To Risk It All by Admiral James Stavridis and others, Sailing True North by Admiral James Stavridis USN, How to Think Like a Roman Emperor by Donald Robertson, Thoughts of a Philosophical Fighter Pilot by James B. Stockdale, Titan by Ron Chernow, Steve Jobs by Walter Isaacson, Benjamin Franklin by Walter Isaacson, Team of Rivals by Doris Kearns Goodwin, The Fish That Ate the Whale by Rich Cohen, Shoe Dog by Phil Knight and others, and Mistakes Were Made (but Not by Me) by Carol Tavris, and discussed The Wealth of Nations by Adam Smith.
Books mentioned, in the order they came up
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Meditations
Meditations by Marcus Aurelius is a collection of personal reflections and Stoic philosophy written by the Roman emperor.
Recommended“My whole life was changed by a copy of Mark Sprelius' Meditations that I bought for $9 on Amazon. It changed me personally and also professionally.”
Where to get it
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Trillion-dollar Coach
Trillion-dollar Coach by Eric Schmidt, Alan Eagle, and Jonathan Rosenberg is a leadership manual that details the management philosophies and coaching strategies of legendary executive Bill Campbell.
Recommended“Here is Trillion Dollar Coach. This is written by Eric Schmidt, one of the most successful business CEOs of all time. But this is about one of the greatest leadership coaches of all time who mentored and coached Steve Jobs, Larry Page, and some of the biggest CEOs in the history of Silicon Valley.”
Where to get it
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What I Learned Losing a Million Dollars
Recommended“What I Learned Losing a Million Dollars is about a trader on the Chicago Stock Exchange who blows it in the 80s and loses over a million dollars. Obviously, today they're playing with slightly larger amounts of money, but this one is really good.”
Where to get it
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Billion Dollar Lessons
Recommended“Billion Dollar Lessons. Again, you can learn as much from people's very expensive failures than you can from their successes.”
Where to get it
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How I Built this
How I Built This by Guy Raz and Nils Parker is a business and entrepreneurship book that chronicles the unexpected, challenging paths to success taken by the world's most inspiring founders and creators.
Recommended“Guy Raz has interviewed basically every CEO of a big or new company of the last generation or so. This book, How I Built This, is incredible. Actually, funny story. We have a hardcover of How I Built This up there in the book tower. Can't have that one. I don't think it's coming out anytime soon.”
Where to get it
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Good to Great
Good to Great by Jim Collins is a popular business book exploring how companies transition from being mediocre to achieving sustained greatness.
Recommended“Jim Collins, good to great. This one's very important.”
Where to get it
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Unreasonable Hospitality
Unreasonable Hospitality by Will Guidara is a celebrated business and leadership book that details how extraordinary, personalized service can transform a great organization into an unforgettable experience.
Recommended“Unreasonable Hospitality, one of the great restauranteurs and hospitality experts. This book is great.”
Where to get it
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Zero to One
Zero to One by Peter A.
Recommended“Peter Thiel, who I wrote a book about zero to one. Obviously, controversial guy, but his thinking here is incredible. Everyone should read this.”
Where to get it
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The 22 Immutable Laws of Marketing
The 22 Immutable Laws of Marketing by Al Ries and Jack Trout is a classic business book that outlines fundamental marketing principles and strategic positioning rules for companies seeking market dominance.
Recommended“As far as marketing goes, I'd also throw in the 22 immutable laws of marketing. This is both a marketing and a business and a life strategy...”
Where to get it
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The $100 startup
The 100 Startup by Chris Guillebeau is a practical guide to building a modern micro-business based on personal passions and low startup costs.
Recommended“But I do like the $100 startup. Noah Kagan's also written some interesting stuff...”
Where to get it
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The Lean Startup
The Lean Startup by Eric Ries is a highly influential business and management book that introduces a methodology for creating and launching businesses through iterative product releases, validated learning, and minimum viable products.
Recommended“Eric Ries talks about this in the lean startup. Very good.”
Where to get it
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Thinking in Bets
Thinking in Bets by Annie Duke is a popular nonfiction book exploring how to make better decisions under conditions of uncertainty and how to avoid evaluating choices solely based on their eventual outcomes.
Recommended“Andy Duke talking about this thinking in bets.”
Where to get it
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The Hard Thing About Hard Things
The Hard Thing About Hard Things by Ben Horowitz is a candid entrepreneurship and management guide that addresses the brutal realities of running a business, making difficult decisions, and leading through crisis.
Recommended“Ben Horowitz, hard thing about hard things. You will have to make hard decisions in life and in leadership. Very important.”
Where to get it
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Essentialism
Essentialism by Greg McKeown is a practical guide that encourages readers to focus on the vital few pursuits rather than the trivial many, aiming to achieve more through deliberate elimination.
Recommended“McAllen's essentialism, also really good.”
Where to get it
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The 33 Strategies of War
The 33 Strategies of War by Robert Greene and Don Leslie is a strategic guide that distills historical military conflicts and tactical principles into actionable lessons for navigating competitive modern environments.
Recommended“I'd also throw in Robert Greene's stuff. 33 Strategy of War. This is an incredibly powerful book...”
Where to get it
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The 48 Laws of Power
The 48 Laws of Power by Robert Greene and Joost Elffers is a provocative guide examining historical strategies for acquiring and navigating power.
Recommended“I would also add in the 48 Laws of Power. You don't have to be one of the people in the book, but you want to be able to protect against...”
Where to get it
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Mastery
Mastery by Robert Greene is a non-fiction book that explores the paths to true expertise by examining the lives of historical figures, contemporary masters, and the dynamics of mentorship.
Recommended“It's one lesson a day from all of his books. 33 Strategy of War, Laws of Human Nature, 48 Laws of Power, Art of Seduction, Mastery.”
Where to get it
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The Laws of Human Nature
The Laws of Human Nature by Robert Greene is a dense and insightful exploration of human behavior, emotional mastery, and the underlying patterns that drive people throughout their lives.
Recommended“It's one lesson a day from all of his books. 33 Strategy of War, Laws of Human Nature, 48 Laws of Power, Art of Seduction, Mastery.”
Where to get it
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The Art of Seduction
The Art of Seduction by Robert Greene is a psychological exploration of power dynamics, human desire, and the subtle strategies behind interpersonal charm and influence.
Recommended“It's one lesson a day from all of his books. 33 Strategy of War, Laws of Human Nature, 48 Laws of Power, Art of Seduction, Mastery.”
Where to get it
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To Risk It All
Recommended“I really like Admiral James Stavridis, his book Sailing True North and To Risk It All.”
Where to get it
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Sailing True North
Sailing True North by Admiral James Stavridis is an exploration of character and leadership told through the biographies of ten historical admirals.
Recommended“I really like Admiral James Stavridis, his book Sailing True North and To Risk It All.”
Where to get it
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How to Think Like a Roman Emperor
How to Think Like a Roman Emperor by Donald Robertson is a practical philosophy and self-help book that blends modern cognitive behavioral therapy with the ancient Stoic teachings of Roman Emperor Marcus Aurelius.
Recommended“How to Think Like a Roman Emperor. We had more leaders and business people who would think like a Roman emperor. They'd be more successful. This is Donald Robertson's book on Mark Shrullis.”
Where to get it
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The Wealth of Nations
The Wealth of Nations by Adam Smith is a foundational text in classical economics that explores the nature and causes of national wealth through the division of labor, productivity, and free markets.
Discussed“Maybe in your MBA, you're reading Adam Smith's Wealth of Nations, obviously important, bedrock of modern capitalism.”
Where to get it
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Thoughts of a Philosophical Fighter Pilot
Thoughts of a Philosophical Fighter Pilot is a reflective work by James B.
Recommended“which becomes not just this book, Thoughts of a Philosophical Fighter Pilot, which is some of the best essays and articles on leadership and adversity and difficulty that you'll ever read.”
Where to get it
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Titan
Titan by Ron Chernow is a definitive business biography detailing the life of industrialist John D.
Recommended“Chernow's Titan, incredible.”
Where to get it
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Steve Jobs
Steve Jobs by Walter Isaacson is an acclaimed biography that chronicles the tumultuous life, visionary intensity, and complex personality of the Apple cofounder through extensive collaboration and interviews conducted while Jobs was dying.
Recommended“Walter Isaacson, Steve Jobs, Elon Musk, great.”
Where to get it
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Benjamin Franklin
Benjamin Franklin by Walter Isaacson is an acclaimed biography that chronicles the life, intellect, and multifaceted career of one of America's most influential founding figures.
Recommended“His book on Benjamin Franklin, also incredibly successful and brilliant business person.”
Where to get it
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Team of Rivals
Team of Rivals by Doris Kearns Goodwin is a celebrated historical account examining Abraham Lincoln's remarkable political leadership and his strategy of appointing former political opponents to his cabinet.
Recommended“And then Team of Rivals, absolute must-read, Lincoln's genius as a wielder of an unwieldy cabinet.”
Where to get it
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The Fish That Ate the Whale
The Fish That Ate the Whale by Rich Cohen is a biography about Sam Zemurray, the historic figure known as the banana king who rose from immigrant poverty to build a massive fruit empire.
Recommended“This is actually written with Rich Cohen, who's one of my favorite writers, who did this book, Fish That Ate the Whale, about the Samuel Zamuri, who starts as the little guy...”
Where to get it
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Shoe Dog
Shoe Dog by Phil Knight is a candid and gripping memoir by the co-founder of Nike that chronicles the harrowing early struggles, relentless perseverance, and eventual global success of the iconic athletic brand.
Recommended“Of course, Shoe Dog, about Phil Knight, also very incredible.”
Where to get it
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Mistakes Were Made (but Not by Me)
Mistakes Were Made (but Not by Me) by Carol Tavris and Elliot Aronson investigates the psychology of self-justification, exploring how the human brain distorts reality to protect the ego from acknowledging error.
Recommended“So this book on cognitive dissonance, Mistakes Were Made But Not By Me, very important. Highly recommend...”
Where to get it
