MIB: Ryan Holiday’s Sex Tape Escapades

This week, we sit down with writer and media strategist Ryan Holiday who is the former director of marketing for now bankrupted and controversial manufacturer American Apparel. He is the author of six books, including “The Daily Stoic” and most recently “Conspiracy: Peter Thiel, Hulk Hogan, Gawker and the Anatomy of Intrigue.”

Holiday was covering the Hulk Hogan vs Gawker and founder Nick Denton litigation, which was bankrolled by Thiel (who owned 10% of Facebook pre-IPO), and leads to a $140 million verdict against Denton & Gawker. Soon after, both Thiel and Denton reach out to Holiday, to share the parts of the story that never made it into court. Thus was conceived an idea for a book.

When doing research on Holiday in preparation for this interview, I was surprised to learn that he had written a book — The Daily Stoic — I had previously read. The book has become extremely popular in Silicon Valley and Among NFL players and coaches.

He discusses how certain web-only media outlets became digital sweatshops. The reinvigoration of media outlets like the New York Times and Washington Post are a direct response to this click happy blogs; so too are the rise of podcasts and audible books for people who want more in-depth discussions as opposed to superficiality.

His favorite books are referenced below; our conversation transcript will be available here tomorrow.

You can stream/download the full conversation, including the podcast extras on iTunesBloombergOvercast, and Soundcloud. Our earlier podcasts can all be found on iTunesSoundcloudOvercast and Bloomberg.




Ryan Holiday’s Authored Books

Conspiracy: Peter Thiel, Hulk Hogan, Gawker, and the Anatomy of Intrigue by Ryan Holiday

The Daily Stoic: 366 Meditations on Wisdom, Perseverance, and the Art of Living by Ryan Holiday

Trust Me, I’m Lying: Confessions of a Media Manipulator by Ryan Holiday

Ego Is the Enemy by Ryan Holiday

The Obstacle Is the Way: The Timeless Art of Turning Trials into Triumph by Ryan Holiday

Growth Hacker Marketing: A Primer on the Future of PR, Marketing, and Advertising by Ryan Holiday

Ryan Holiday’s Favorite Books

The 48 Laws of Power by Robert Greene

The Fish That Ate the Whale: The Life and Times of America’s Banana King by Rich Cohen

Tough Jews : Fathers, Sons, and Gangster Dreams by Rich Cohen


The Brass Check: A Study of American Journalism by Upton Sinclair

Life by Keith Richards


Grant and Sherman: The Friendship That Won the Civil War by Charles Flood

Grant and Sherman: Civil War Memoirs (2 Volumes) by Ulysses S. Grant

Memoirs of General W.T. Sherman by William Sherman

Sherman: Soldier, Realist, American by B. H. Liddell Hart


Alexander Hamilton by Ron Chernow

Washington: A Life by Ron Chernow

Titan: The Life of John D. Rockefeller, Sr. by Ron Chernow

Letters from a Stoic by Seneca

Meditations by Marcus Aurelius



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