Episode 088: Ryan Holiday – How To Find The Best Mentor & Viewing Obstacles As Opportunities

Ryan Holiday is a fascinating thinker.  I appreciate his stories and the manner in which he views the world.  This conversation was entertaining and educational. Ryan is an incredibly interesting person.  During our time together, Ryan talked about stoicism and why he’s fascinated by it as well as you should be willing to work for free (as long as it’s for the right person).

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 most recent book, “The Obstacle Is The Way” is based on the Stoic exercise of framing obstacles as opportunities. The book has sold more than 100,000 copies and was reportedly read by the New England Patriots during their 2014 Super Bowl Victory over the Seattle Seahawks as well as distributed through the locker room of the Seahawks in the following offseason by the team's front office.

Episode 088: Ryan Holiday

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“The best leaders are process oriented… Not results oriented.  They are focused on doing great work more than on acquiring lots of money.”

The Learning Leader Show

Some Questions I Ask:

• What are the common characteristics of leaders who have sustained excellence?
• Why should we be willing to work for free?
• Why was it the right decision for Amelia Earhart to knowingly be paid less than her male counterparts?
• What did you learn working for Robert Green?
• Why don’t you like the title for your first book, “Trust Me, I’m Lying?”
• How do you “trade up the chain?”
• What is the proper strategy for your first book?
• What specific changes have you made to grow your following?
• What is your process for writing?
• Define a great learning leader…

In This Episode, You Will Learn:

• The importance on being process oriented rather than results oriented
• Why working for a fantastic mentor will massively accelerate your success
• Austin Kleon – “Say yes, until you can afford to say no”
• Why using a job as a journalist as a great excuse to interview people
• Stoicism is an ancient Greek school of philosophy. The school taught that virtue, the highest good, is based on knowledge, and that the wise live in harmony with the divine Reason (also identified with Fate and Providence) that governs nature, and are indifferent to the vicissitudes of fortune and to pleasure and pain.
• A very interesting Amelia Earhart story
• Why continuous learning is the key to success

“An hour of Sheryl Sandberg’s time is hard to quantify.  It is so valuable.”

Continue Learning:

• Go To Ryan’s Website: net
• Read: The Obstacle Is The Way
• Follow Ryan on Twitter: @RyanHoliday
• Read Robert Greene’s: The 48 Laws Of Power

You may also like these episodes:

Episode 001: How To Become A Master Connector With Jayson Gaignard From MasterMind Talks

Episode 034: Jimmy Hatch – Shot While Searching For Bowe Bergdahl And Sky Diving With Gabby Giffords

Episode 004: How Todd Wagner (and Mark Cuban) Sold Broadcast.com To Yahoo! For $5.7 Billion

Episode 010: Shane Snow – How To Accelerate Success Using Smart Cuts

Did you enjoy the podcast?

This was a jam packed episode full of great content.  Ryan Holiday is a leader who leads an very interesting life. Who do you know that needs to hear this?  Send them to The Learning Leader Show!

Episode edited by the great J Scott Donnell

Bio From RyanHoliday.net

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 most recent book, “The Obstacle Is The Way” is based on the Stoic exercise of framing obstacles as opportunities. The book has sold more than 100,000 copies and was reportedly read by the New England Patriots during their 2014 Super Bowl Victory over the Seattle Seahawks as well as distributed through the locker room of the Seahawks in the following offseason by the team's front office.

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.