21 | RYAN HOLIDAY - Best Selling Author and former Director of Marketing at American Apparel
Play • 28 min

This week, Cory speaks to author, marketer and entrepreneur Ryan Holiday, who is well known for being a controversial media strategist, particularly when he was the Director of Marketing at American Apparel and founder of creative consulting firm Brass Check Marketing. Ryan, in addition, is a bestselling author of six books, including “The Obstacle Is the Way”, “Ego Is the Enemy” and “The Daily Stoic” and has written for several of the worlds largest publications while being a media columnist and editor-at-large for the New York Observer. He has a new book out today which you can get now on Amazon and elsewhere titled “Conspiracy: Peter Thiel, Hulk Hogan, Gawker, and the Anatomy of Intrigue”. In this week’s episode, he tells us why he left college at the age of 19, how he was then hired and mentored by prolific writers Robert Greene and Tucker Max, to landing an advisory position to American Apparel’s founder only to in only a year become its Director of Marketing. Ryan goes over his most controversial marketing campaigns, some of the best lessons he’s learned along the way and discusses his new book.


Ryan Holiday (@RyanHoliday) has never shied away from controversy, from leaving school at the age of 19 against his parent’s wishes to casting porn stars in commercials as the young marketing director of American Apparel. It has worked in his favor as he has risen the corporate ranks and then gone on to write over a half dozen books including Trust Me, I’m Lying: Confessions of a Media Manipulator, The Obstacle is the Way, and Ego Is the Enemy.

When it comes to giving others career advice, Ryan cautions against following a passion. “The common career advice is to find your passion, and that can somewhat be dangerous, right? Just because you’re passionate about something, doesn’t mean that you’re good at it,” said Ryan in his interview with Cory Levy on OFF RCRD.

Cory Levy spoke with Ryan about his journey as a controversial young marketing director and successful author of the OFF RCRD Podcast. Ryan’s newest book goes behind the scenes of a groundbreaking court case involving a famous sex tape, a professional wrestler, and tech investor Peter Thiel. The book, Conspiracy: Peter Thiel, Hulk Hogan, Gawker, and the Anatomy of Intrigue, is now available on Amazon.

Ryan credits his success to his mentors, including authors Robert Greene and Tucker Max. Because of his experience with mentors and how he’s been able to leverage their help to build his career, Ryan is often approached by aspiring writers to become their mentor.

More episodes
Clear search
Close search
Google apps
Main menu