Turning Adversity To Advantage: Ryan Holiday on Why The Obstacle Is The Way
About this episode
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 Learn more about your ad choices. Visit podcastchoices.com/adchoices
Listen to this episode in English to learn English
Podcast episodes are one of the highest-density ways to absorb English at native pace. Turning Adversity To Advantage: Ryan Holiday on Why The Obstacle Is The Way from The Rich Roll Podcast gives you natural dialogue, unscripted speech, and vocabulary that actually appears in real conversations.
In the Hinto app, every word in the transcript is tappable. Tap an unknown word, see the translation in your language instantly, and keep listening without breaking flow.
Episodes to Learn English
- Michelle Khare Is The Tom Cruise Of YouTube: How Anxiety Became Her Superpower Jul 27, 2026
- Malcolm Gladwell & Chris Chavez Think We're Selling Running All Wrong Jul 23, 2026
- What Are You Actually Capable Of? Mark Dowdle On Winning A 306 Mile Backyard Ultra Jul 20, 2026
- Episode 1,000: Rich & Julie Piatt Celebrate By Going Back To Where It All Began Jul 13, 2026
- Thrilling Tales Of Modern Men: Danny McBride On Ego, Grievance & The Stories Men Tell Themselves Jul 6, 2026
- Play Is The Miracle Drug: Dr. Kelly Starrett On Movement, Recovery, & The Wellness Trap Jul 2, 2026
- What Happened To The Vegan Movement? Rich & Simon Hill On The Rise & Fall Of Plant-Based Eating Jun 29, 2026
- Radiohead’s Ed O’Brien on Depression, Trauma & Finding Light Again Jun 22, 2026
- Fulfillment Maxxing: Why Offline Is The New Online & How to Feel Alive Again Jun 18, 2026
- Rachel Entrekin Runs On Joy: How She Won The Cocodona 250 Outright By Letting Go Of The Outcome Jun 15, 2026
- Touch Grass: Andrew Yang Returns To Talk Phone Addiction, AI's Cognitive Toll, & The Fight For Your Attention Jun 8, 2026
- ROLL ON: Enhanced Games Jun 4, 2026
- Paul Rosolie Met An Uncontacted Tribe & Is Trying To Protect Them: On Preserving The Amazon To Save All Life On Earth Jun 1, 2026
- How to Stop Sabotaging Your Own Life With Joe Hudson May 25, 2026
- Inside My 72-Hour Psychedelic Iboga Therapy With Julie Piatt May 21, 2026
- Smile, Or You're Doing It Wrong: Andy Glaze On Relentless Positivity, PTSD, & The Healing Power Of Movement May 18, 2026
- What's Going Right: Dr. Paul Conti On Self-Sabotage, Trauma & Why Being Hard On Yourself Is Slowing You Down May 11, 2026
- Pay Now, Love It Later: Why I Work Out at 4 AM & The Mindset That Wins The Long Game May 7, 2026
- David Epstein On Why Constraints Drive Creativity, The Myth Of Productive Freedom, & How Limits Make Us Better May 4, 2026
- What We're Still Getting Wrong About Women's Health & Fitness: Dr. Stacy Sims Live Apr 27, 2026
- ROLL ON: Stop Optimizing Your Life & Start Living It, Seeking Depth Over Algorithms, The Future of Podcasting, Artemis II, Media Diet & More Apr 23, 2026
- In Waves & War: Marcus & Amber Capone On Psychedelic Treatment For Veteran PTSD, Rebuilding Life After War & The Mission To Heal A Generation Apr 20, 2026
- Everything Is A Story: Journalist Nick Bilton Thinks AI Might End Humanity & How Stories Could Save Us Apr 13, 2026
- Rebuilding My Body & Starting Over After Spinal Fusion Surgery Apr 9, 2026
- The King of Moab: Ultrarunner Max Jolliffe On Winning Moab 240, Recovery From Heroin Addiction & Why Suffering Is His Greatest Teacher Apr 6, 2026
- Rich Speaks On Tiger Woods, Addiction & The Wounds That Fame Can't Heal Apr 2, 2026
- Arthur Brooks On The Crisis Of Meaning & How To Actually Find It Mar 30, 2026
- Decoding the New U.S. Dietary Guidelines with Simon Hill: What They Got Right, Wrong & Why It Matters Mar 26, 2026
- Future-Proof Your Brain from Dementia & The Lifestyle Levers That Keep You Sharp with Neuroscientist Dr. Tommy Wood Mar 23, 2026
- Stanford Professors Bill Burnett & Dave Evans On How To Design A Meaningful Life Mar 16, 2026