Ryan Holiday is a media strategist and prominent writer on strategy and business. After dropping out of college at nineteen to apprentice under Robert Greene, author of The 48 Laws of Power, he went on to advise many bestselling authors and multiplatinum musicians. He served as director of marketing at American Apparel for many years, where his campaigns have been used as case studies by Twitter, YouTube, and Google and written about in AdAge, the New York Times, and Fast Company.

His first book, Trust Me I’m Lying—which the Financial Times called an “astonishing, disturbing book”—was a debut bestseller and is taught in colleges around the world. He is the author of two other books and is now published in 16 languages. He currently lives in Austin, Texas with his rebellious puppy, Hanno and pet goats.

“Success is being able to do what you want. Often the people with the most money are the least free.”Click-To-Tweet

In This Episode:

  • The concept of parent-child fit and why it was missing for him
  • Finding the people who understood him in college
  • Learning under Robert Greene
  • His method for ideating and organizing thoughts
  • Why his work can be exhilarating and exhausting
  • The on-going journey to find inner peace
  • The destructiveness of one’s “ego”
  • How his experience at American Apparel create an intersection of his intellectual work and personal life



“Writing – I was naturally good enough that I could lose myself in it.”

“The nice part about writing is that it’s so hard and it’s never as good as you want it to be”

“When I’m working on a book, that’s probably when my wife is least happy, because that’s when I’m prone to disappear in the middle of a conversation, or a drive, or an experience. I’m drawn to another place.”

“The ego that comes with being successful early is the worst possible thing you can introduce.”

“The thing that makes them so good and focused, ironically or paradoxically deprives them of enjoying the fruits of that labor fully the way a different person might envision that it would feel.”

On ego: “The world was not big enough for Alexander the Great, but a coffin was sufficient.”

“The idea that you don’t have to pull an answer out of your ass is a freeing thought. You can just say I don’t know enough to answer.”


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Ryan Holiday is an American author, marketer, and entrepreneur. He is a media strategist, the former Director of Marketing for American Apparel and a media columnist and editor-at-large for the New York Observer.