The Tim Ferriss Podcast: Ryan Holiday (#4)

“The impediment to action advances action. What stands in the way becomes the way.” — Marcus Aurelius

This post includes:

– Sponsor intro (please visit them)

– Episode description

– Quick favor

– Show notes and tons of useful links, including mentioned books and documentaries

This episode of The Tim Ferriss Show is sponsored by HipDial, which I’ve been a fan of for ages.

I use HipDial for conference calls: no stupid PIN numbers, no hitting #, and you get a text when people join, so you don’t have to wait. It’s rocks–try it for a free month, and you’ll never go back.

Now, on to the main event…

My guest is Ryan Holiday, who became Director of Marketing at American Apparel at age 21 (!). He’s a beast.

Since dropping out of college at 19 to apprentice under strategist Robert Greene (author of The 48 Laws of Power), Ryan has advised many New York Times bestselling authors and mega-multi-platinum musicians. He is a master of the media, and he knows how to build massive buzz while responding to unexpected crises. He can compete or counterpunch with the best.

I hired Ryan to help with the launches of The 4-Hour Body and The 4-Hour Chef. His unorthodox approaches always impress me.

I loved his new book (The Obstacle Is The Way) so much that I bought the audiobook format and produced it with him. It is the newest addition to The Tim Ferriss Book Club.

In this episode, we discuss dozens of topics, including the real-world strategies he uses to thrive (not just survive) when the world is exploding around him.

You can find the transcript of this episode here. Transcripts of all episodes can be found here.

Episode 4: Ryan Holiday

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Show Notes for Episodes 4 (Thanks, Ian!)

  • The surprising story of how Ryan was introduced to stoicism by Dr. Drew
  • What makes a “quake book”?
  • How Marcus Aurelius helped Ryan survive a tough breakup
  • About esoteric philosophical ideas that are excellent tools in the modern world
  • Deconstructing the “Big 3” stoics – Seneca | Epictetus | Aurelius
    • Is stoicism compatible with material or financial success, or are they completely at odds with one another?
    • Tim’s strategy for developing connections in Silicon Valley
    • Cultivating advantageous mentorships with peak performers
    • The story of Benjamin Franklin’s lending library…

  • What Ryan credits for his ability to “get shit done.”
  • What a day in the life of Ryan Holiday looks like (deflecting meeting requests, etc.)
  • Why e-mail can save time compared to a phone call
  • The most common mistake that new writers make
  • Delving into the writing process
  • How Ryan approaches goal setting and financial security

  • Friend curation, and the factors that guide Ryan’s decision making
  • Rapid-fire questions:
  1. Ryan’s fight entrance song?
  2. One thing he would change about himself?
  3. When he thinks of the word “successful,” who comes to mind, and why?
  4. If he could study any expert in the world, who would it be and why?
  5. Advice to his younger self?
  6. What Ryan orders at the bar?
  • Who should drop out of college versus who should stay in college
  • And much, much more…


  1. Fake Jeff Jarvis
  2. FelixSolomon
  3. Media Redefined by Jason Hirschhorn
  4. MariaPapova of BrainPickings
  • Ryan’s favorite blogs:
  1. Feedly
  2. Ta-Nehisi Coate’s blog
  3. Mark Cuban’s blog
  • Ryan’s Favorite Reddits:

Stoicism | Philosophy | History Porn | Ask Historians

Today I Learned | First World Problems | Reddit Books


  1. The Black Swan
  2. Fooled by Randomness
  3. Antifragile
  1. Oranges
  2. Levels of the Game
  3. The Survival of the Bark Canoe
  4. Plymouth Rock (Free Online)
  5. The Control of Nature
  6. Giving Good Weight


Connect with Ryan Holiday: Twitter | Website | Thought Catalogue | Observer


Just listen on Stitcher, or you can listen using the player below —

Episode 4: Ryan Holiday

The Tim Ferriss Show is one of the most popular podcasts in the world with more than 900 million downloads. It has been selected for "Best of Apple Podcasts" three times, it is often the #1 interview podcast across all of Apple Podcasts, and it's been ranked #1 out of 400,000+ podcasts on many occasions. To listen to any of the past episodes for free, check out this page.

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51 Replies to “The Tim Ferriss Podcast: Ryan Holiday (#4)”

  1. I am a fan of both Tim and Ryan. Great episode. The title of this book hits so deep. I am already using it in daily conversations. Love that you touched on the Ben Franklin Effect. Keep em coming!!

  2. Another great episode. Digging it, but I must admit it was pretty entertaining in the last episode to hear you, Kelly and Justin become progressively more slurred in your verbiage.

  3. Great episode Tim! I’m a big fan of Ryan Holiday and all his books, I can’t wait to pick up his latest book soon as well.

    Keep up the awesome work, loving these episodes!

  4. Just finished The Art of Learning on audible. Great recommendation. Looks like The Obstacle Is the Way is next on the list after I finish Flash Boys!

  5. I am all in for content, I found the interview inspiring, and you’re doing much better than I am doing. But I found myself being way much distracted by the lack of skill on Ryan speech, so much of “like”, “if you know what I mean”, and “eeehhh”, I think he could benefit of Carol Fleming works ( ), and talking about the sound of your voice and if anybody feels comfortable in their own voice, my candidate is Morgan Freeman. Probably he regrets being himself because he can’t listen to himself the same way other can hear him =) .

    Last, on my own self, English is not my first language, if you want to correct me, I’d appreciate it. Thanks

  6. Why people take breakfast at a bar/restaurant? Is it better to start the day? I can’t go out without having a coffee at home. I have a friend who always have a double expresso at a bar before going to work. Maybe it feels better to think you wake up and have to go to the bar instead to straight to work?

  7. How can I download this if I don’t use itunes? I burn podcasts onto cds and listen to them in my car’s mp3 cd player (very 2006, I know)

  8. Tim-

    I have listened to each of the podcasts. I know this is an experiment in progress, and you have refined the questions you have asked your guests over the four episodes. However, I think you have nailed it with the previous podcast.

    While I have gathered plenty of information from the podcasts with K. Rose, J. Waitzkin, and R. Holiday, I have only listened to each of these podcasts once. I have listened to the podcast with Doctors Starrett and Major and yourself three times now.

    The dynamic of having multiple guests with overlapping interests and expert knowledge created the feeling of a smooth, unforced conversation which touched on a wide range of interrelated talking points. It allowed the guests to feel comfortable sharing their unfiltered views (ok the wine may have helped a bit) and you were able to play moderator/bridge for Kstar and JAM. From my point of view, this is the best format for your podcast. I would love to see you reunite with Neil Strauss and Chase Jarvis for a discussion on the creative process and monetizing the products. Also, both guys have built communities of avid learners and self-improvers through their businesses (The Society and CreativeLive). I would be interested to hear their shared experiences as they have built those businesses.

    In closing, one of my favorite ‘interview’ shows was “Dinner for Five” hosted by Jon Favreau. The show, which aired on IFC, brought together writers, directors, actors and producers. The discussions felt authentic as the diverse group would discuss shared experiences, explore the aspects of the creative process, and laugh during the whole thing. That sounds a little disingenuous, linking Hollywood actors with authenticity, but they were just people discussing their professions.

    Thanks for sharing these podcasts. I’m excited to see what you have coming next.

  9. This is the single-best episode (including The Random Show) ever recorded, It’s going in the required listening section to my kids. Tons of writing, thinking, and just being a better human gems in this episode.

  10. Hey Tim, I just finished listening to Josh Waitzkin podcast #2 for the 3rd time and there is one thing that I think would be of HUGE help to me but also most people i guess: at one point he says that right now he’s more focused on UN-learning rather than learning.

    As i’m gaining life experiences and trying to always improve, i can absolutely say that learning is “easy” but unlearning years of bad habits, or changing a whole section of your mindset is so damn hard.

    Do you think that unlearning would make an interesting subject for a podcast or post? I’d love to know how to use and master NLP on a daily basis to slowly steer the ship in another direction. I had a presentation with Morgan Drmaj, a friend of Neil Strauss, and he suggested having a sheet in your pocket and that EVERY time you have a particular behavior that you want to change, you stop anything your doing, take your sheet, read it, then continue doing what you were doing. I think that’s a great trick but I’d love to learn more things for unlearning like this.



  11. Tim, I’m humbled by how good these episodes are. Having just interviewed Ryan myself ahead of the launch [Moderator: Link Removed], this is a really great schooling in comparing and contrasting against. The years of being interviewed yourself have really rubbed off and made you an excellent interviewer. Ed

  12. Loved the part about what a writer is saying is more important then academic credibility. Coming from a former professional athlete, reading Ric Flair’s autobiography was truly amazing true life stories told by the only man that could live to tell it. The book needed some serious editing but worth every moment reading it.

    Thanks, Tim and Ryan

  13. Excellent podcast. I wasn’t familiar with Ryan before this, and would have written him off based on his job title. Turns out I really like his philosophy and outlook on life.

  14. Love having all the links in the show notes. Thanks for another great episode. My favorite segments were Ryan’s daily routine and the list of influential books. This is such a great place to find unfamiliar material.

  15. Loving the podcast and I’m so happy I don’t have to use stitcher anymore, thank you for the rss feed in the last episode.

    Listening to episode two I probably took more notes that almost any podcast I’ve listened to before. Keep up the good work and thank you!

  16. Please bring Fight Club into it. The Ben Franklin Effect has also been addressed by Chuck Palahniuk in the book Choke.

    Practicing poverty can happen in any context. When you’re buying clothes, as an example, ask “Do I really need this? Would it have utility if I was homeless?”

  17. No doubt Tim Ferriss’ podcasts are the best and this one with Ryan Holiday sounds great as he takes us back to the roots and even I believe that from solution for most of our problems, ideas of innovation to running organisations can be found in the history of great men. I have been reading much about our King Cyrus The Great since childhood and also about many other Persian Zoroastrian Kings as I belong to this oldest religion. At the end of all reading we clearly understand his greatness, the reason why he has such great admirers and one of them was Alexander the Great who admired him to an extent that when he invaded Persia, destroyed everything but repaired the tomb of Cyrus and as its said that he always wanted to visit the tomb and learn much about how he managed such widest empire in history. I’ve read Cyropaedia and really loved this Forbes article of Ryan about Cyrus the Great.

    All through I’ve studied Management but love reading about Artificial Intelligence which gives us readers a magical experience where there’s much being said about enhancing human lives, making work easier, faster, better and building powerful technology which I think will takes us back to our roots one day when the futurists will seek inspiration. Please Tim, one podcast with Elon Musk or Chris Anderson about Drones or Steve Jurvetson if you can. 😀

  18. So much powerful info in this episode! If I can only highlight one thing, it would be Ryan’s thoughts on whether to drop out if college or not. He points out that most of the highly successful CEOs who dropped out actually began their business while still in school, only leaving once it became a legitimate opportunity. Ryan did the same thing.

    My input is always the same as when someone asks me if they should “try” MMA. If you are really unsure, then you are uncertain. And if you’re uncertain, you won’t have the confidence in your decision necessary to succeed.

  19. A lot stands out from this cast: Ryan sure gives this 26-year old a run for his money in terms of impact this far in life!

    More specifically, I love the recognition of walking as legitimate exercise and a good way to spend your time. It’s much more enjoyable, and much easier to commit to, than a lot of higher-intensity activities. Like Time said, highly underrated.

  20. Hi Tim, just a quick typo spot. Franklin’s bio is by Isaacson right?

    Best episode yet! Loved that Ryan brought up Farnam Street. Shane Parrish is an incredible guy!



  21. Amazed by quality and powerful content of first 3 episodes. They helped convert what could be a tedious long drive into useful action.

    However, I can’t find a link to an MP3 for Episode 4 that I can pop onto a thumb drive and into my car player?

    Finally, I would urge you to make an MP3 available for your YouTube episodes for those of us who can’t justify being tied to a tube for that long?


    Jay Honeycutt

  22. This interview was awesome. I was hooked from the moment I realized he worked for Tucker Max, but the more I listened the less I cared about what Ryan had done and looked forward to what he will do. The insight in this interview is awesome. It inspired me to think outside the box and expand my horizon on the material I consume. Thanks!

  23. Seriously, this Ryan guy is boring. Awesome book ‘am sure. But I get the feeling you might benefit from not jogging everyday and going on a hedonistic binge…like get over yourself a little. Then come back and write another awesome book.

  24. Thank you Tim and Ryan for introducing me to Stoicism. If it weren’t for you two I think I would never have picked up philosophy.

  25. Simply – one of the best interviews I have ever listened to. Thank you Tim and Ryan for your riffing, and insights into your thinking, humility and sources of learning. Gotta go back to this, again and again, so much to pick through and re-stock on. Hail, great men!

  26. This is certainly an episode to return to often. The book is great and adds more sparks of enthusiasm to my intrigue with stoic philosophy.

    Keep up the good work Tim. Podcast was a superb idea and is a constant source of inspiration for me!

  27. Tim, I just wanted to say that I am loving the podcast format – So much intellectual food for thought. Among the best of them was Ryan Holiday though – A truly great interview and one that generated many great nuggets of thought and things worth pursuing!

  28. Tim, I’ve just discovered your podcasts and I find them absoluately inspiring. No bullshit, just pure awesomeness and wisdom and strories that make you want to learn more, get the most of life and just be a better person. And each interview makes me believe again (as sometimes seeing things happening in your neighbourhood proves opposite) that PEOPLE ARE AMAZING CREATURES.

    Thanks for all your efforts!

  29. 1) Thank you and Ryan for this paradigm-shifting episode.

    2) Per your joking confession, can you afford the distraction of a 30-min voice coaching session? As a non-egotistical person (references available upon request) who appreciates their recorded voice, has studied multiple speech and singing techniques, and has spent the last four years coaching people to speech (and musical) excellence, I very much want to work with you. This flavor of learning will be different from your previous experiments (the reward of the new). And, while one session isn’t enough to solidify a new technique, you will hear a difference. I will conveniently be in SF tomorrow through the 17th of this month.

    Ryan, you would like the results of coaching as well, and I would be honored to work with you.

    3) The mentor gathering tips are especially helpful.

    4) I want this to basically follow your directions and have my name, Vivian Clifton, but WordPress seems to prefer otherwise #apologies.

  30. Tim: I am a huge fan. Due to a progressive hearing loss I rely on captions. Do you make transcripts available for episodes? Please consider captioning. I would be most grateful!

  31. Great, list of books here. Unfortunately, due to an overload of podcasts I am only reading fiction. I can’t really tell which ones are fiction or non-fiction :/

  32. I’m finding a lot of useful information in Tim Ferriss’ books and podcasts. Nice to see that “Stranger in a strange Land” is on your bookshelf, too. Also, Ryan Holiday mentioned that he is interested in doing some archaeology, the “Ghost Ranch” in NW New Mexico has wonderful seminars. Friends of mine have so enjoyed the courses that they participate in there.

  33. Hearing this certainly impacted my perspective on what is possible for one to achieve. Truly an inspiring listen. Thanks Tim and Ryan

  34. Around 78 min. -It’s important not to make friends with people who have Trauma or trouble. – I had to listen to that part a few times to believe he actually said that, How many millions of people did he just alienate? Got to love millennials.

  35. Really enjoyed this podcast tuned in to find out about stoicism and learnt so much more! Thank you 😊

  36. Tim, You mentioned that you use to volunteer at TiE, The Indus Entrepreneurs. I am one of the Global Board of Trustees of the organisation. I understand from you website, you are not doing any speaker engagements but it will be great to have in some capacity at our Global Event this year in December (14th – 16th) in Hyderabad, India. look forward to hearing from you.