Ryan Holiday

Ryan Holiday is best known for translating ancient Stoic wisdom into practical tools for navigating contemporary life.

At 19, he dropped out of college to apprentice under Robert Greene, author of The 48 Laws of Power — an unconventional start that set the stage for a career defined by curiosity, risk, and contrarian thinking. He went on to become Director of Marketing at American Apparel, navigating both the brand’s meteoric rise and its chaotic, controversial culture. These experiences shaped Holiday’s insights into strategy, human behaviour, and leadership.

After American Apparel, Holiday founded Brass Check, a creative agency advising clients such as Google, TASER, Complex, and some of the world’s most influential authors and entrepreneurs. His books including The Obstacle Is the Way, Ego Is the Enemy, Stillness Is the Key, and The Daily Stoic have sold millions of copies in over thirty languages.

Holiday’s audience spans NFL coaches, world-class athletes, political leaders, entrepreneurs, and everyday readers, all drawn to his guidance on cultivating resilience, self-mastery, and ethical judgment in an unpredictable world. His work explores failure, doubt, and the human ego as lived experiences, drawing from history, philosophy, and his own unconventional career. Ryan Holiday challenges readers and listeners to confront obstacles head-on, rethink what success means, and reflect on how daily habits shape character.

His podcasts, The Daily Stoic and The Daily Dad, reach millions, and his email newsletters engage 1.5 million readers worldwide. Away from the digital spotlight, Ryan Holiday finds balance on a ranch outside Austin, Texas, raising cattle, donkeys, and goats — a daily practice of the Stoic principles he champions: presence, patience, and intentionality.