The Tim Ferriss Podcast, Episode 4: Ryan Holiday


“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.

And…want to win some cool stuff today? Tweet out your favorite quote or line from this episode, using the following format, and I’ll pick a few of my favorites for prizes:

“[Insert quote]” More: #TFS”

To encourage other people to retweet, try and keep your entire tweet to 125 characters or fewer. The iTunes link above will be automatically shortened.

Deadline is 8:30pm PST.

QUICK FAVOR — If you haven’t already, can you pretty please:

1) Leave a review of the podcast on iTunes here?
2) Vote as “helpful” the reviews you most agree with? Here’s the link. The vast majority are 5 stars (290 out of 333), but there’s some wild Haterade, too, if that’s your thing.

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 —

Posted on: May 6, 2014.

Watch The Tim Ferriss Experiment, the new #1-rated TV show with "the world's best human guinea pig" (Newsweek), Tim Ferriss. It's Mythbusters meets Jackass. Shot and edited by the Emmy-award winning team behind Anthony Bourdain's No Reservations and Parts Unknown. Here's the trailer.

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Comment Rules: Remember what Fonzie was like? Cool. That’s how we’re gonna be — cool. Critical is fine, but if you’re rude, we’ll delete your stuff. Please do not put your URL in the comment text and please use your PERSONAL name or initials and not your business name, as the latter comes off like spam. Have fun and thanks for adding to the conversation! (Thanks to Brian Oberkirch for the inspiration)

37 comments on “The Tim Ferriss Podcast, Episode 4: Ryan Holiday

  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!