Ryan Holiday (@RyanHoliday) is a strategist and writer. He dropped out of college at 19 to apprentice under Robert Greene, author of The 48 Laws of Power, and later served as the director of marketing for American Apparel. His company, Brass Check, has advised clients like Google, TASER, and Complex, as well as many prominent bestselling authors. Holiday has written four previous books, including The Obstacle Is the Way, which has been translated into 17 languages and has a cult following among NFL coaches, world-class athletes, TV personalities, political leaders, and others around the world. Ryan lives on a small ranch outside of Austin, Texas, and his latest book is Ego Is The Enemy.
Ryan and Tim cover a lot in this conversation, including:
Meltdowns and how Ryan handles them
Workaholics Anonymous — How it works, what worked for him, what didn’t
The tipping points for his last book, The Obstacle Is the Way
External versus internal obstacles
Sherman versus Grant leadership and “success”
Howard Hughes versus Elon Musk
Thinking of “first principles”
If you only have 5 minutes, listen to what Ryan believes is one of the biggest threats to your creativity.