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.

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 —

The Tim Ferriss Show is one of the most popular podcasts in the world with more than 600 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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