Ryan Holiday – The College Dropout Who Made Ancient Philosophy Modern
When Ryan Holiday dropped out of the University of California, Riverside at just 19 years old, his parents weren’t exactly thrilled. Most people would have called it a mistake. But Holiday saw something different—an opportunity that would eventually transform him into one of the most influential philosophers of our generation.
Today, at 37, Holiday has sold over 5 million books in more than 40 languages, amassed over 150 million podcast downloads through The Daily Stoic, and built a daily newsletter reaching 1.5 million engaged readers. His books have been embraced by NFL coaches, Olympic athletes, Fortune 500 CEOs, and Academy Award-winning actors.
But Ryan Holiday’s story isn’t about overnight success or viral fame. It’s about something far more profound: the patient, deliberate application of 2,000-year-old Stoic wisdom to modern life.
From Sacramento to the Front Lines of Marketing
Born on June 16, 1987, in Sacramento, California, Holiday grew up in a household that valued service and structure. His father was a police detective, his mother a high school principal. Nothing in his upbringing screamed “future philosopher”—yet the seeds were already being planted.
At 19, during a conference with radio and television host Dr. Drew Pinsky, Holiday asked for a book recommendation. Dr. Drew pointed him toward the Stoics. That single recommendation changed everything.
“To say that recommendation changed my life does not go far enough,” Holiday later reflected. “It has in fact directed the entire course of my life.”
Reading Marcus Aurelius’s Meditations was what author Tyler Cowen calls a “quake book”—it shook everything Holiday knew about the world. But unlike most college students who discover philosophy and then promptly forget it after finals, Holiday saw something practical, something he could actually use.
The Robert Greene Years: An Unconventional Education
After leaving college, Holiday moved to Los Angeles to work at a Hollywood talent agency. But his real education was about to begin when he became a research assistant for Robert Greene, the bestselling author of The 48 Laws of Power.
Greene became what Holiday describes as a “surrogate father”—a mentor who taught him not just how to write, but how to think, research, and understand power, human nature, and the patterns of history.
This apprenticeship was crucial. While his former classmates were sitting in lecture halls, Holiday was learning the craft of writing from one of the masters, diving deep into historical research, and seeing firsthand how ideas could be packaged and shared with millions.
Working with Greene, Holiday co-created The 50th Law, which became a New York Times bestseller in 2009. He was still in his early twenties.
The American Apparel Era: Success and Its Discontents
Holiday’s unconventional path led him to become the Director of Marketing for American Apparel at just 21 years old. It was a position most MBA graduates would kill for, and Holiday was barely old enough to rent a car.
He was brilliant at it—creative, strategic, and willing to push boundaries. But success came with a cost. The world of marketing, media manipulation, and manufactured controversy began to take its toll.
This period would later inspire his first book, Trust Me, I’m Lying (2012), an exposé of how the modern media ecosystem works, who benefits from it, and how it can be manipulated. The book was controversial, eye-opening, and established Holiday as someone who understood the mechanics of attention and influence.
But more importantly, this era taught Holiday something essential: success without wisdom is hollow. All the professional achievement in the world couldn’t provide what he was really looking for—peace, purpose, and a life well-lived.
Ryan Holidays Stoic Trilogy That Changed Everything
In 2014, Holiday published The Obstacle Is the Way, a book that would quietly revolutionize how millions of people think about adversity.
The book wasn’t designed to go viral. It was about facing pain, suffering, and difficulty—and using those things as fuel. Not exactly light reading. But it struck a nerve at exactly the right time.
Athletes picked it up. Coaches passed it around locker rooms. Business leaders started quoting it in boardrooms. The New England Patriots and Seattle Seahawks both invited Holiday to their headquarters to discuss the book’s ideas. NBA All-Star Chris Bosh called it something he “couldn’t live without.”
By December 2016, the book had sold over 230,000 copies. But more than sales numbers, it had started a movement.
Holiday followed with Ego Is the Enemy (2016), which examines how ego sabotages our goals whether we’re just starting out, experiencing success, or facing failure. The book uses historical figures as case studies to illustrate the perils of egotism and the power of humility.
Then came The Daily Stoic (2016), co-authored with Stephen Hanselman—a daily devotional containing 366 meditations on Stoic wisdom. This book reached #2 on the Wall Street Journal bestseller list and has become a bedside staple for millions seeking daily philosophical guidance.
Stillness Is the Key (2019) completed what many call Holiday’s “Stoic trilogy,” exploring how inner calm and stillness are critical to achieving our goals and performing at our best in an increasingly chaotic world.
As of 2024, these books have collectively spent over 300 weeks on bestseller lists and continue to introduce new readers to ancient philosophy every single day.
The Four Virtues Series: Going Deeper
Not content to rest on his success, Holiday launched an ambitious new project: exploring each of the four cardinal Stoic virtues in depth.
Courage Is Calling: Fortune Favors the Brave (2021) examines the most foundational virtue, using stories of historic and contemporary leaders to show how to conquer fear and practice courage in daily life.
Discipline Is Destiny: The Power of Self-Control (2022) celebrates the awesome power of self-discipline in a world of temptation and excess, featuring stories of those who have seized this ancient idea.
Right Thing, Right Now: Good Values, Good Character, Good Deeds (2024) emphasizes the importance of ethical behavior and integrity, exploring the virtue of justice.
The series demonstrates Holiday’s evolution as a thinker—he’s no longer just translating ancient wisdom, he’s building a comprehensive philosophical framework for modern living.
The Daily Stoic Empire: Philosophy as Practice
What truly sets Ryan Holiday apart isn’t just his books—it’s the ecosystem he’s built around Stoic practice.
The Daily Stoic Podcast, launched in 2015, has become one of the most successful philosophy podcasts in the world, with over 150 million downloads to date and approximately 2 million monthly downloads. The podcast features daily meditations (2-3 minutes of Stoic wisdom every weekday) and long-form interviews with everyone from Tim Ferriss and Malcolm Gladwell to Matthew McConaughey and Camila Cabello.
The Daily Stoic Newsletter reaches 1.5 million engaged subscribers every single morning, delivering practical Stoic wisdom directly to their inboxes. Over seven years, this newsletter has essentially published seven books’ worth of content—completely free.
The Daily Dad Podcast and Newsletter applies Stoic principles to fatherhood, growing 30% year-over-year and helping parents navigate one of life’s most important roles.
The Daily Stoic YouTube Channel has garnered 63 million views and 4.4 million hours watched, creating what Holiday calls “the largest Stoic library in the world.”
Together, these platforms reach millions of people daily, making ancient philosophy accessible, practical, and relevant to modern challenges.
The Painted Porch: Philosophy in the Physical World
In 2020, during the pandemic, Ryan Holiday and his wife Samantha opened The Painted Porch Bookshop in Bastrop, Texas. It’s not just any bookstore—it’s an independent shop on historic Main Street that embodies Holiday’s values.
The store carries all of Holiday’s titles alongside carefully curated selections—books Holiday has used while writing, books he and Samantha have loved over the years, and works that represent the best of human thought and creativity.
“If people want to discover new books and have a unique experience, they come to us,” Holiday explains.
The bookstore represents something important: in an age of Amazon and algorithms, Holiday created a physical space where ideas matter, where browsing is encouraged, and where community can form around books and philosophy.
It’s Stoicism in action—building something real, something valuable, something that serves others.
Life on the Ranch: Walking the Stoic Talk
Holiday lives with his wife and two sons on a 40-acre ranch outside Austin, Texas, in Bastrop County. The ranch includes a small herd of cows, donkeys, and goats.
This isn’t affectation or philosophical theater—it’s intentional. The Stoics believed in living close to nature, in physical work, in the rhythms of life that connect us to something larger than our egos.
Holiday regularly talks about how much he loves being a dad, playing with his kids, and walking through the fields. Stoicism, to him, isn’t about being emotionless or denying pleasure—it’s about not letting those things control you.
“Stoicism isn’t about feeling nothing,” Holiday often explains. “It’s about not letting those feelings run your life.”
The Criticism and the Response
Not everyone has embraced Holiday’s approach to Stoicism. Some academic philosophers have questioned whether his work constitutes “real” philosophy.
At Stoicon 2016, an annual conference for academics and practitioners of Stoicism, some attendees were skeptical. Massimo Pigliucci, a philosophy professor at City College of New York, recalled people asking, “Wait a minute, that’s not Stoicism.”
Holiday’s response was characteristically Stoic: he acknowledged the criticism, stayed humble, and kept working.
“I say that my books are books that feature Stoicism as opposed to being works of Stoicism,” he explained. “I think it’s incredibly hard to add something new to the canon of ancient philosophy as a modern person. There is room to translate, extrapolate and illustrate—and that’s what I did.”
Gregory Hays, the classicist whose translation of Marcus Aurelius’s Meditations became a bestseller, offered a different perspective, saying Holiday’s work is “very much in the spirit of its ancient models” and praising him as “a great storyteller.”
The New York Times credited Holiday with contributing to the increased popularity of Stoicism, describing him as “leading the charge for Stoicism” which has gained particular traction among Silicon Valley entrepreneurs, athletes, and business leaders.
Why Ryan Holiday Matters
In a world drowning in content, Holiday has created something different. His work isn’t about motivation—it’s about perspective. His books don’t tell you what to do; they ask you to reconsider how you see the world.
That’s deeper. And it lasts longer.
Holiday has succeeded where countless philosophers have failed: he’s made ancient wisdom accessible without dumbing it down, practical without being shallow, and popular without being pandering.
His approach is slow, patient, and deliberate. He reads ancient texts, takes notes, thinks deeply about them, then writes. The result isn’t “content”—it’s meditation.
And when the world gets chaotic—as it does, constantly—that kind of message doesn’t just sound nice. It saves people.
The Three Stoic Disciplines in Action
Holiday organizes Stoic philosophy around three core disciplines, captured beautifully in a quote from Marcus Aurelius he often cites:
“Objective judgment, now at this very moment. Unselfish action, now at this very moment. Willing acceptance, now at this very moment, of all external events. That is all you need.”
Perception: How we see the world determines our experience of it. The obstacle is the way. The problem is the opportunity.
Action: We must act despite uncertainty, difficulty, or fear. Courage, discipline, and virtue aren’t theoretical—they’re practiced.
Will: We must accept what we cannot control and find peace within that acceptance.
This framework runs through all of Holiday’s work, offering a practical roadmap for navigating modern life’s complexity.
The Legacy in the Making
At 37, Ryan Holiday is still building. His exclusive partnership with Backyard Ventures in 2025 reflects the continued growth and evolution of his multimedia empire.
But the legacy isn’t really about downloads, book sales, or social media followers—though his 4.5 million combined following is impressive.
The legacy is in the lives changed. The person who read The Obstacle Is the Way before a difficult medical diagnosis and found strength. The father who subscribed to The Daily Dad and became more present with his children. The entrepreneur who embraced Ego Is the Enemy and built something meaningful instead of just big.
Holiday has taken philosophy—something most people associate with dusty classrooms and impossible terminology—and made it a daily practice for millions.
He’s proven that ancient wisdom isn’t obsolete; it’s essential.
And he’s shown that success without wisdom is hollow, but wisdom shared generously creates ripples that extend far beyond any individual life.
The Stoic for Our Time
Ryan Holiday’s story is far from over. With new books in development, expanding podcast audiences, a growing community, and an unwavering commitment to Stoic principles, he’s just getting started.
But perhaps what makes Holiday most compelling isn’t his success—it’s his genuineness. He doesn’t come off as a guru. He doesn’t sell 30-day transformations. He’s not peddling quick fixes or easy answers.
Instead, he offers something rare and valuable: timeless wisdom, patiently translated, generously shared, and consistently practiced.
In a world that rewards flash over substance, Holiday has built something enduring. In a culture obsessed with overnight success, he’s demonstrated the power of patient, deliberate work. In an age of superficial self-help, he’s revived something deeper—philosophy as a way of life.
That’s not just a career. That’s a calling.
And millions of people around the world are grateful he answered it.
Ready to explore Stoic philosophy? Visit DailyStoic.com to subscribe to the free daily email, listen to The Daily Stoic Podcast, or visit The Painted Porch Bookshop in Bastrop, Texas to discover your next great read.
Ryan Holiday’s Essential Reading:
- The Obstacle Is the Way – Transform adversity into advantage
- Ego Is the Enemy – Conquer the greatest obstacle to success
- The Daily Stoic – 366 days of Stoic wisdom
- Stillness Is the Key – Find peace in a chaotic world
- Courage Is Calling – Embrace the foundational virtue
- Discipline Is Destiny – Master the power of self-control