Feb 2, 2023 · 40m · american-optimist
Ryan Holiday: How Stoicism Changed the World · Joe Lonsdale
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In this episode of American Optimist, host Joe Lonsdale interviews author Ryan Holiday about his journey from exposing media manipulation to revitalizing ancient Stoic philosophy for modern readers. Together, they explore the four cardinal virtues, civic duty, and how practical wisdom can counter cultural cynicism and broken media incentives.
How this conversation actually went
Every chapter scored 0–10 on four independent dynamics. Hover any point for the reasoning behind the score. Joe holds 23.7% of the talking time here. How this is scored →
Joe as informed peer 3.8 Guest teaching 3.1 Guest disagreement 0.6 Joe pushing back 0.2
speaking balance: gold is Joe, purple is the guest (3 minute bins)
Sharpest disagreement ▶ 30:34 Holiday dismantles the Brown University Marcus Aurelius protest
Holiday forcefully rejects the modern trend of labeling ancient emperors like Marcus Aurelius as modern colonizers, calling the framing historically ignorant.
Hardest push from Joe ▶ 22:40 Lonsdale on modern culture's rejection of beautyLonsdale challenges modern cultural cynicism, asserting modern art rejects classical beauty solely to tear things down.
Biggest teaching moment ▶ 33:33 Holiday educates on Musonius Rufus and gender in StoicismHoliday reframes the critique of Stoicism as male-only by citing first-century philosopher Musonius Rufus advocating that virtue is genderless.
Joe holds their own ▶ 20:08 Lonsdale cites Cato's Letters influencing the FoundingLonsdale demonstrates deep historical knowledge by citing the 1720s Cato's Letters and their direct influence on the American Declaration of Independence.
the scores for every segment, with the reasoning behind each
| Chapter | Topic | Joe as informed peer | Guest teaching | Guest disagreement | Joe pushing back | Why |
|---|---|---|---|---|---|---|
| Joe Lonsdale Introduces Ryan Holiday | 3 | 2 | 0 | 0 | Joe introduces Ryan and asks him about his background and early career with Robert Greene and American Apparel. The atmosphere is warm, collaborative, and conversational. | |
| Sensationalism and the Broken Incentives of Modern Media | 4 | 3 | 1 | 1 | Lonsdale and Holiday discuss media manipulation and how algorithms incentivize outrage, with Lonsdale sharing personal anecdotes about his own tweets. | |
| Publishing 'The Obstacle is the Way' and Modernizing Stoicism | 4 | 4 | 1 | 0 | Holiday explains writing 'The Obstacle is the Way' and how Marcus Aurelius and Epictetus viewed mortality (memento mori). Lonsdale contributes a quote about Marcus Aurelius and his children. | |
| The Four Cardinal Virtues and Civic Duty | 3 | 3 | 0 | 0 | Holiday outlines the cardinal virtues and explains how Stoics embraced civic duty rather than retreating into isolation. Lonsdale agrees and connects it to personal leadership. | |
| Strategic Marketing of Ideas: 'Ego is the Enemy' | 3 | 2 | 1 | 0 | Holiday talks about rebranding humility into 'Ego is the Enemy' and temperance into 'Discipline is Destiny' to overcome audience resistance, comparing modern education to Aesop's fables. | |
| Classical Foundations of the American Founding | 5 | 3 | 0 | 0 | Lonsdale and Holiday discuss how the American founders drew heavily from classical Roman figures like Cato and Cincinnatus. Lonsdale mentions Cato's Letters and the naming of Cincinnati. | |
| Plutarch's Biographies vs. Modern Iconoclasm | 4 | 3 | 1 | 1 | Holiday contrasts Plutarch's focus on virtue with modern biographical iconoclasm, using the removal of Robert E. Lee's statue in New Orleans to argue that critique must be paired with celebrating virtuous figures. | |
| Evaluating Flawed Leaders and MLK's Rhetorical Strategy | 4 | 3 | 1 | 0 | Lonsdale and Holiday discuss Thomas Jefferson and Martin Luther King Jr.'s strategy of holding flawed founders to their stated ideals rather than erasing them. | |
| The Origin of Stoicism in the Public Agora | 4 | 4 | 0 | 0 | Holiday recounts the origin story of Zeno shipwrecked in Athens founding Stoicism in the Stoa Poikile within the Agora. Lonsdale adds context regarding Phoenician dye. | |
| Critiquing Anti-Western Civ Movements & Misreading History | 4 | 4 | 2 | 0 | Holiday and Lonsdale critique protests against Western classics, citing the student protest at Brown University against a Marcus Aurelius statue as ahistorical anachronism. | |
| The 2,000-Year Great Conversation vs. Modern Cynicism | 4 | 3 | 0 | 0 | Holiday and Lonsdale conclude by defending the 2,000-year conversation of Western philosophy against cynicism, emphasizing optimism and living virtue through action. |
Statements from this episode (18)
Holiday: 2011 media manipulation tactics are now cyber warfare playbooks
“And so a lot of the things that I was talking about in that book are now part of the sort of like cyber warfare playbook or the media manipulation playbook.”
Holiday: Media dislikes Trump the most while giving him the most publicity
“You know, like, look, there's no one the media dislikes more than Trump, and there is no one who has gotten more free publicity from said media than Trump, right?”
Lonsdale: Media focused exclusively on three controversial tweets out of 3,500
“I know, I mean, even for myself, I think I checked, I have 3500 tweets as of the time we're recording this, and I think there's been like three of them that were controversial, then the media like wrote all the stories about those, nothing else, even though th…”
Holiday: Media and algorithms effectively govern America by shaping public opinion
“Technology, different words is true then, or true now, but he was basically saying that, look, America is a company, is a country governed by public opinion, so what governs public opinion governs a country, and so these algorithms, the mediums that we use, so…”
Holiday: Positive messengers must master the media tools exploited by bad actors
“The worst people in our society are the most adept at exploiting and using the media and or viral ideas and what we have, what people who have positive messages or real perspectives or lessons to teach people have to do much, a much better job of figuring out …”
Holiday: Publisher cut advance by over half for 'Obstacle is the Way'
“They gave me, I think, less than half what I've gotten for my first book, for my second book about what became my second book, which is about Stoke philosophy.”
Holiday: 'The Obstacle is the Way' approached two million copies sold
“You know, which is, you know, sold a million and a half, two million, on the verge of two million copies.”
Holiday: Stoicism centers on responding to uncontrollable events with four virtues
“Stoicism is built actually around the same cardinal virtues as Christianity, courage, self-discipline, justice, and wisdom. And the idea was that we don't control what happens to us in life, but We can always respond to what happens to us in life with those vi…”
Holiday: Stoics engage in public life by default unlike Epicureans
“The distinction in the ancient world, the two rival schools are Epicureanism and Stoicism. And Seneca, one of the great Stoics, is saying, like, an Epicurean will get involved in public life if they have to. And he says, a Stoic gets involved in public life un…”
Holiday: Building a better mousetrap fails without intentional framing
“There's that Emerson quote where he says, you know, if you build a better mousetrap, the world will beat a path to your door. That's not how life works. Like you have to create a compelling reason for people to be interested. You have to think about what their…”
Holiday: Modern society babies teenagers instead of teaching classical philosophy
“A seventeen-year-old is more than capable of reading a philosophical text, or reading Plutarch, or any of these, like, we baby our kids when it comes to books as if, like, for literally thousands of years, people, you know, your kid, your seventeen-year-old A …”
Holiday: Society's virtue collapse stems from abandoning moral narratives
“The means by which society has been communicating these timeless ideas. Of course it's by example, but it's also by narrative and myth and the art that you have up in your house, the stories you tell them, the movies you watch, you know, the people you support…”
Holiday: Famous Revolutionary War slogans originated in Addison's play Cato
“Even like, even some of the famous lines, like, give me liberty or give me death. I regret I have but one life to lose my country. Those are lines from the play.”
Holiday: MLK effectively used Thomas Jefferson's own words to force progress
“Martin Luther King was incredibly educated, incredibly well-read, and he, what he did was he would study, say, a Thomas Jefferson, and then he would take Thomas Jefferson at his word,
Right?
And force people who liked Thomas Jefferson to try to live up to thos…”
Holiday: Cultural mess stems from tearing down classical ideas without replacement
“I think you can trace a little bit of the mess that we're in now to the tearing down of those ideas and the failure to replace it with something else.”
Holiday: Brown University students campaigned to remove Marcus Aurelius statue
“There's actually a protest at Brown University the last couple years. They wanted to pull down, there's a stat, an equestrian statue of Marcus Aurelius on campus,”
Holiday: Stoic Musonius Rufus argued for genderless virtue in ancient Rome
“Musonius Rufus, who's Epictetus's philosophy teacher, is like, He gives a speech on, he says, should women be taught philosophy? He says, is virtue the same in men and in women? And he makes this argument, you know, in Rome around the first century that virtue…”
Holiday: Daily Stoic newsletter reaches over 500,000 subscribers every day
“Look, the Daily Stoic email goes out to over a half a million people every day. That is the, without a doubt, the largest collection Of people interested in stoic philosophy to ever have been assembled at one time in human history, right?”