I love talking to smart people. Today's guest is certainly that — and so much more. Contravening millennial stereotypes, Ryan Holiday is a prolific, rising literary talent. A maverick media strategist. Not to mention a philosopher of sorts — a guy with big ideas often at odds with the status quo. An autodidact, Ryan dropped out of college at nineteen to apprentice under acclaimed author Robert Greene, author of (among many other great books) The 48 Laws of Power*, later graduating to advise many New York Times bestselling authors like Tim Ferriss and RRP #154 alum Tucker Max, multiplatinum musicians like Linkin Park and startups like Casey Neistat's ( RRP 73 & RRP 144 ) recently launched social media platform Beme. By the time he was legally allowed to drink (21!) Ryan had already ascended to director of marketing duties at American Apparel, where his iconoclastic campaigns and tactics have been used as case studies by Twitter, YouTube, and Google and written about in places like AdAge, the New York Times, and Fast Company. Ryan is also the bestselling author of 3 books, including Trust Me I’m Lying* – a highly entertaining and admittedly disturbing first hand look at the machinations behind digital media's dark underbelly — and The Obstacle Is The Way* – a modern and practical reframing of stoicism, the ancient Roman philosophy originated by guys like Marcus Aurelius, Seneca and Epictetus, with a focus on functional applicability of stoic principles for turning modern day obstacles into opportunities and adversity to advantage. If you think philosophy is purely academic — a useless waste of time reserved for the arrogant intellectual elite — Ryan has a message for you: think again. I really love this book. I found it to be eminently practical. An incredibly insightful and utilitarian tool box for navigating crises, strengthening character and maximizing excellence in any situation, irrespective of circumstance. On RyanHoliday.net and places like Thought Catalog and Observer (where he is editor at large), Ryan writes frequently on a wide variety of business and marketing related subject matters. But it's his fresh and unique take on real life stuff that keeps me coming back. Enjoy! Rich