Conversation with Ryan Holiday

Ryan Holiday is a media strategist for notorious clients like Tucker Max and Dov Charney. After dropping out of college at 19 to apprentice under the strategist Robert Greene, he went on to advise many bestselling authors and multi-platinum musicians. He is the Director of Marketing at American Apparel, where his work in advertising was internationally known.

Some weeks ago, Ryan sent me a copy of his first book so I could review it. Trust Me I’m Lying: Confessions of a Media Manipulator is a realistic (and somewhat depressing) analysis of the current status of the media, and what it means for us, its consumers. As I was reading it, and being a long time reader of his blog, I felt the urge to discuss some of his points face to face with him, so I asked him and he was open to having a call. For those that know me well, they know that I consider Ryan a big online influence of mine, so having this conversation was not only a pleasure but an honor. Thank you, Ryan.

Some of the topics we discuss on the call:

• Ryan tells us a bit about his new book and past experiences.
• Ryan’s motivations to write this book after working on media for so long.
• The depressing reality of mainstream media, and what may need to happen for it to change.
• Our assumptions with the media at an individual level and their implications.
• The way the media is designed, and the choices we’re left with.
• The impact of technology in the media landscape.
• Traditional media in the past, and our regression to its problems (plus new ones). Ryan’s belief that we’re worst than before.
• How Ryan chooses what to read and trust online.
• Limitations of the human mind when consuming entertainment as information.
• Problems with the crowd-sourcing model of information.
• Lack of accountability in mainstream media.
• Our concerns with immediacy as the main criteria for value.
• What happens when you add filter bubbles to “immediate entertainment” that we consume as information.
• How to know who’s dangerous in the media, who needs to be stopped or punished.
• Ryan explains how he reads so much, and his reading philosophy and methodology.

Relevant Links:

Ryan’s site
Trust Me, I’m Lying on Amazon