The Life and Times of Ryan Holiday

On April 14, 2025, Ryan Holiday was in a hotel room in Annapolis, getting ready to walk onstage at the United States Naval Academy. He had spoken there more than half a dozen times since 2019, as part of a series on Stoicism and the pursuit of virtue. The invitation to this one had come the previous November, and the subject was wisdom. He had sent his slides over the night before so they could be loaded onto the projectors.

A call came. Would he leave out the part about the books?

Earlier that month the academy had pulled 381 titles from the shelves of its Nimitz Library, part of the Pentagon’s compliance with an executive order against what it called divisive theories. Among the removed books were Maya Angelou’s I Know Why the Caged Bird Sings and Ibram X. Kendi’s How to Be an Antiracist. Holiday’s presentation mentioned the removal, and he had been asked to cut the mention. He refused.

“I said I couldn’t do that,” he told CNN. “I couldn’t have spoken in front of these midshipmen about courage and about doing the right thing, and then remove, I think, a very reasonable objection to a very egregious concept.” (CNN)

His own account, published in The Free Press four days later, is three sentences long: “They asked me to delete this part of the speech. I declined. My lecture was canceled.”

By CNN’s account he learned of it an hour before he was due onstage. By his own, twenty minutes. Either way, he flew home to Texas and delivered the lecture to a camera instead, because a lecture hall can be closed and a recording cannot.

That episode is now the first thing many people know about him, and it is unintelligible without the rest of the life. A man who refuses an institution on principle is interesting only if you know what the principle cost him to acquire, and where he acquired it.

A government-town childhood

Ryan Clark Holiday was born on June 16, 1987, in Sacramento County, California, and grew up there. His father was a police detective and his mother a high school principal. He has described the place to The Guardian as “a sleepy, government town,” and his own account of the household is deliberately unglamorous: two parents who stayed together and had good jobs. (The Guardian)

He graduated from Granite Bay High School in 2005 and went to the University of California, Riverside, where he studied political science and creative writing. He did not finish. He left in his sophomore year, at nineteen, and moved to Los Angeles. The Guardian notes that his parents were troubled by it, less from ambition than from an inability to imagine a life off the school-to-college-to-job conveyor belt. (Wikipedia)

What he had instead of a degree was a correspondence. He had written a review of Tucker Max’s website and sent it to Max, and that connection put him in the orbit of the writers Max knew. It was through that world, by his own account, that he came to the attention of Robert Greene, the author of The 48 Laws of Power.

Nineteen, and a table in Los Feliz

The legend says he read The 48 Laws of Power, wrote to Greene, and was hired. The legend is wrong, and the correction matters, because it is the difference between a story about a clever letter and a story about how apprenticeships actually begin.

“There I was at 19 years old, sitting across from the great Robert Greene at The Alcove in Los Feliz,” Holiday wrote in 2025. Greene was complaining about how hard it was to find a good research assistant, and Holiday, who was nineteen and had nothing to lose, had to physically restrain himself from leaping across the table. “Fortunately, before I leapt out of my chair, Robert asked if I might have any interest in giving it a shot.” (RyanHoliday.net)

The work was not glamorous. Before transcription software existed, he spent hours transcribing interviews Greene had recorded for The 50th Law. He read the obscure books that Greene was glad to delegate. He found articles, scanned pages in libraries, worked through old archives, tracked people down. And he listened. “I did this for close to 7 years,” he wrote, “even after I became the director of marketing at American Apparel.”

Seven years is the number worth remembering. It is longer than most people spend in graduate school, and it overlapped with everything else in his twenties.

In parallel he took a job as an assistant at a talent agency in Beverly Hills. The Guardian’s Zoe Williams, who interviewed him at length, calls the combination of offers at nineteen the beginning of a long stretch in which he was, in his own phrase, “this wunderkind,” always the youngest specialist in the room.

The hype man writes a confession

He went to work in marketing at American Apparel and rose to director of marketing. The title is worth stating precisely, because the more flattering version of it has been repeated for a decade: he was not chief marketing officer, and Adweek introduced an interview with him under the line “We ask director of marketing Ryan Holiday.” (Adweek) Quillette’s own introduction to a long interview with him says he was chief marketing officer at twenty; in the interview itself he says only that he ended up running the department.

Greene was on the company’s board and brought him in project by project until he was running the department. “Basically, I came in to add one project, and then another, and the next thing I knew I was running the marketing department, which I had no business running at the time,” he told Quillette.

The methods he used there are the reason his first book reads the way it does. He planted stories by posing as an expert he was not. He bought traffic. He ran a campaign against a movie in order to make young men want to see it. He was, by his own description, a media manipulator, and at some point he decided to write down how the manipulation worked, which is a strange thing for a working manipulator to do.

Trust Me, I’m Lying: Confessions of a Media Manipulator came out in 2012. It is a confession written by someone still in the confessional, and it is the origin of everything that follows: the reputation for candor, the discomfort of his critics, and the suspicion, never quite retired, that the man explaining the trick is still running one.

He also learned a lesson at American Apparel that he has repeated ever since, about the founder Dov Charney. Every decision Charney made looked like a bad idea and several of them worked, and the danger of that experience is what it teaches. “An entrepreneur, by definition, succeeds by not listening to all the people who told him that it wasn’t going to work,” Holiday told The Guardian. “But then you learn this incredibly dangerous lesson, which is, don’t listen to other people when they tell you something is a bad idea. It sows the seeds of your destruction.”

The book that went into locker rooms

In 2014 he published The Obstacle Is the Way, and it did not sell. “It sold maybe 3,000 copies in its first week,” Holiday told The Guardian. “It did not exceed anyone’s expectations.”

His own explanation for what happened next is the most useful thing he has said about his own career: “It wasn’t until a year or so later that the sales really started to take off, when it began to make its way through professional sports.” (The Guardian)

That is exactly what happened. The New England Patriots and the Seattle Seahawks both brought him in to talk about the book. Erik Spoelstra gave copies to the Miami Heat, and Chris Bosh named it among the things he could not live without. By December 2016 it had sold more than 230,000 copies, and the NFL’s adoption of a book about a Roman emperor became a story in its own right.

The book works because its premise is narrow and true. It opens on a line from Marcus Aurelius, written in a tent on the Danube frontier: the impediment to action advances action, and what stands in the way becomes the way. Holiday takes that sentence as an operating instruction and spends two hundred pages showing it applied by people who were blocked and then were not.

Two more books followed in 2016: Ego Is the Enemy, on the internal force that defeats talented people, and The Daily Stoic, a devotional of 366 readings co-written with Stephen Hanselman. The second of those turned out to be the important one, not as a book but as a business.

The machine

The Daily Stoic began as an email. It started with roughly ten thousand subscribers in 2016. “We’ll go into 2026 with easily a million people getting it every day,” Holiday said in a 2025 interview. Readers asked to listen instead of read, so he recorded the readings, and the podcast followed in 2018. The brand now spans a website, a newsletter, a podcast, and an Instagram account with three million followers. (The Guardian)

The book sales are harder to pin down because the figures keep moving. The Guardian reported at least five million copies in October 2024, and his publisher now says more than ten million copies in more than forty languages. (Penguin Random House) The safest statement is that the number is in the millions, that it is rising, and that the ten million figure is the publisher’s own.

The bibliography

Nineteen books, counting the co-authored and the children’s titles. The table is the whole of it through 2025.

The reissues are not separate works, but they are worth naming: the four-volume Stoic Virtues boxed set of May 2026, and a tenth-anniversary edition of The Daily Stoic in October 2026 with more than sixty new translations and two bonus chapters. (Penguin Random House) No new original book is scheduled.

He also wrote the foreword to Gregory Hays’s translation of the Meditations, which is a small detail with a large meaning: the popularizer ended up in the front matter of the text he popularized. (Penguin Random House)

April 14, 2025

The lecture was about wisdom, and its argument was that wisdom is not a possession but a practice, and that the practice requires reading widely, especially books with which you disagree. The spine of the talk was James Stockdale, a Naval Academy graduate, Medal of Honor recipient, and prisoner of war in Vietnam, who studied Marxist theory at Stanford in the 1960s not because he was a Marxist but because he wanted to understand the adversary. Stockdale spent seven and a half years in Hanoi, and he credited Epictetus with giving him the strength to survive it. (Wikipedia) The lesson Holiday drew was that a leader who cannot read an enemy’s argument cannot lead anyone anywhere.

His slides said it directly. “Read critically, read dangerously.” “Read like a spy in an enemy’s camp,” which is Seneca. “Leaders must be independent thinkers, otherwise they are not leaders.” There was a screenshot of a New York Times article about the removals, and a photograph of the front of his bookstore in Texas, which carries a Rage Against the Machine lyric across the window: “They don’t gotta burn the books, they just remove ’em.” (CNN)

The academy’s leadership saw the slides. The request that came back was not for a change of topic or tone. It was for deletion.

The Navy’s public explanation, given to ABC News, was that it had made a “schedule change that aligns with its mission of preparing midshipmen for careers of service to our country.” It added: “The Naval Academy is an apolitical institution.”

Holiday’s answer to that is the part of the episode worth keeping. “I actually agree that the Academy should be apolitical,” he told CNN. “That’s what makes this political meddling in their access to books so troubling. And then to suppress criticism of that obvious mistake, is to model even poorer moral leadership to the midshipman.” (CNN)

He was less measured elsewhere. “The idea that there are topics that are off limits or that they can’t handle is absurd on its face,” he told ABC News. (ABC News) And: “If you can’t be trusted around Stacey Abrams’ memoir or Maya Angelou, you probably have no business being a Navy SEAL or holding an assault rifle or flying a fighter jet. You’re either an adult or you’re not.”

And the sentence that is really the thesis of the whole lecture, and of the life that produced it: “if you’re not thinking for yourself, you are, by definition, not leading.”

He gave the talk anyway, alone in a studio in Texas, and put it on the internet. The obstacle became the way, which is either a coincidence or the best possible advertisement for the book, and there is no way to tell the difference from outside.

What the critics say

The case against him is not that he is a fraud. It is that he is a marketer who found a philosophy and sold it, and that the selling shaped the philosophy.

Zoe Williams, in a long and genuinely admiring profile for The Guardian, put the sharpest version of it. His books, she wrote, “do not so much represent a meaningful through-line of the ancient philosophy, but instead pick up quotes and notions so freely, attach them to modern exemplars so randomly, that it’s like putting stoicism into a Magimix until the only building block of thought you have left is the alphabet.” (The Guardian)

The charge has a specific shape. Rockefeller as an example of overcoming adversity is a strange choice for a philosophy whose central claim is that wealth is not a good. A book about enduring what you cannot control, read by people who control a great deal, can become a technique for feeling virtuous about the arrangement.

Holiday’s answer is better than his critics usually allow, and he gave it in the same interview. “My initial attraction to stoicism is what it can do for you: how it can make you more resilient, more productive, think clearer, be a master of yourself,” he said. “This is a perfectly fine entry point into the philosophy. But if you miss what the philosophy is also asking of you, in terms of ethics and morals and its emphasis on the virtue of justice, how we’re interconnected and interrelated, then really, what you’ve just discovered is a recipe for being a better sociopath. Which is not what stoicism is.”

That is a fair statement of the danger, offered by the man who profits from the entry point. It is also, in a sense, the most Stoic thing about him: the acknowledgment that the thing he sells can be misused, stated plainly, without abandoning the selling.

There is a second criticism, quieter, from inside the academy. Philosophers who practise Stoicism professionally have been skeptical of him for a decade, on the grounds that a devotional is not a curriculum and that reading Marcus in fragments is not reading Marcus. Massimo Pigliucci, who organizes the annual Stoicon conference at which Holiday spoke in 2016, reported that some attendees looked at the keynote and objected that it was not Stoicism at all. (Wikipedia, citing The New York Times)

The objection is not wrong. It is also not the whole question. The Meditations was written by a man talking himself into the day, in fragments, for his own use. A reader who takes one fragment a morning for a year has read the book in something closer to its native form than a reader who takes a course on it.

The library next door

In July 2026, Holiday opened a room at 914 Main Street in Bastrop, Texas, next door to the bookstore he opened there in 2021. It is about 150 square feet, it once served as a barbershop waiting room, and it holds one kind of book: titles that have been removed from schools or libraries, or otherwise suppressed. Anyone can walk in and take one for free.

“That sort of got me going down this banned books rabbit hole,” he told CultureMap Austin, describing the origin of the project, and the origin was the cancelled lecture.

The shelves hold Tolstoy’s A Calendar of Wisdom, banned in the Soviet Union for its religious content, next to 1984, Fahrenheit 451, The Great Gatsby, To Kill a Mockingbird, and Huckleberry Finn. Readers send books by mail. The team restocks more often than they expected.

His defense of the project is the most precise thing he has said about censorship. People told him the books were not really banned, since you can still buy them on Amazon. “First of all, just because you can buy it on Amazon doesn’t mean it’s a good thing that it’s being removed from a library,” he said. “The point of a library is to make books accessible to people without them having to buy them.”

What the life adds up to

Strip out the marketing and the podcast and the boxed sets, and the biography has a simple shape. A nineteen-year-old talked his way into an apprenticeship and worked at it for seven years. A twenty-something ran marketing for a company whose founder was a genius and a wreck, and wrote a book about the machinery he had operated. Then he found a philosophy built for people who cannot control their circumstances, and spent a decade handing it to people who can.

The worst that can be said is that he made an ancient discipline safe for the people least likely to need it, and got rich doing so. The best is that he put a two-thousand-year-old practice into the hands of several million people who would never have opened Epictetus, and that when an institution asked him to trim a lecture about courage so it would not embarrass the institution, he declined, at some cost, and then built a library out of the refusal.

Both are true. The measure of a popularizer is not whether the popular version is the whole of the thing. It is whether a reader who starts there ends up somewhere deeper. On that measure the verdict is still out, and it will be settled one reader at a time, in the same small increments by which the practice itself works.

The hall in Annapolis stayed empty that afternoon. Something got built anyway.

Sources

• CNN, “US Naval Academy canceled author’s lecture that would have criticized book bans,” April 19, 2025
• ABC News, “Naval Academy cancels speech by podcaster amid cultural turmoil,” April 19, 2025
• Ryan Holiday, “This Is the Lecture That the Naval Academy Didn’t Want Me to Give,” The Free Press, April 23, 2025
• Zoe Williams, “The stoicism secret: how Ryan Holiday became a Silicon Valley guru,” The Guardian, October 28, 2024
• Ryan Holiday, “Without This, You’ll Never Reach Your Potential,” RyanHoliday.net, October 15, 2025
• Quillette, “The Demise of Gawker: An Interview with Ryan Holiday,” December 13, 2018
• Natalie Grigson, “Bastrop bookseller opens library for lending out banned books,” CultureMap Austin, August 5, 2026
• Penguin Random House, Ryan Holiday author page
• Wikipedia, “Ryan Holiday” (used for dates and for the bibliography, cross-checked against the publisher’s own editions)

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