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Ryan Holiday (Replay), Media Strategist & Bestselling Author

Today’s guest is Ryan Holiday. I had this wonderful guest on earlier this Spring and Ryan is a thought-provoking media strategist, bestselling author of three books, and he’s not even 30 yet – I’m so jealous! Most recently his very successful books is called, The Obstacle is the Way: The Timeless Art of Turning Trials into Triumph. He has been responsible for a number of manipulative stunts and media controversies, and has been accused of being a “media manipulator” which he writes about in his first book Trust Me, I’m Lying. And he’s only 27 years old! After dropping out from University of California at 19 to apprentice under Robert Greene, author of The 48 Laws of Power, he went on to advise many bestselling authors and multiplatinum musicians, including 50 Cent and Tim Ferriss, whom I had the honor of interviewing earlier this year (check out episode 60).

Ryan also served as Director of Marketing at American Apparel for many years, where his campaigns ended up being used as case studies by Twitter, YouTube, and Google and written about in AdAge, the New York Times, and Fast Company. Ryan now works as the media columnist for the New York Observer. And his work has appeared in Forbes, Fast Company, The Huffington Post, The Columbia Journalism Review, ThoughtCatalog and

Several takeaways from our interview:

  • Ryan’s formula for creative success that lets you turn obstacles into opportunities.
  • Why he chose to quit college… it wasn’t an easy decision.
  • How stoic principals can vastly improve your professional and financial life.
  • The value in negative thinking…

If you’d like to learn more about Ryan Holiday, visit his website and follow him on Twitter @RyanHoliday.

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