Business Leaders Who Matter To Me: Ryan Holiday

Ryan Holiday, author, speaker, mentor

Over the past eight years, I have sought mentors from books and podcasts. I’m not sure I knew I was doing that in the beginning, but looking back, I was always looking for people I could learn from. I’ve never met most of these people—they’re not mentors in that sense—but they’ve been a big influence on me professionally. They’re important to me.

So I’ve launched a series where I will highlight some of these people in articles and podcasts of my own.

Today, I want to talk about…


Holiday has been on my mind a lot lately because I re-listened to his appearance on Cal Fussman’s podcast, and that prompted me to seek out his other appearances on various podcasts, including his interview on The James Altucher Show — the episode titled, “Competition is for Losers.

But I’ve admired Ryan Holiday for years, now, ever since my aunt gave me his book, “The Obstacle is the Way.” It quickly became one of my favorite books, to the point where I enjoy giving copies to others.

He’s the author of a number of books, including “The Perennial Seller.” A creative guide of sorts for professionals, leaders, and marketers. I am currently reading, “Trust Me, I’m Lying.” If you want to understand how the mainstream media industry works and why there is so much polarization in the news today, read this. It will completely change your perspective on many topics and it will introduce you to the world of media manipulation.

It is also worthwhile to check out Holiday’s appearance on “The Ask Gary Vee Show.” I say that because Gary Vaynerchuk and Ryan Holiday together tell it like it is. And Holiday’s website is loaded with great insights, including his recommended reading list.

I’ve learned I’m not alone in my admiration. He’s huge in professional sports, for example.

Here’s what so many people value about him:

  • His thoughts on the philosophy of stoicism (he actually makes it interesting, unlike many of my middle school teachers)
  • His method for simplifying one’s work
  • His ideas on self-reflection
  • His thoughts on reading
  • His opinions on writing
  • His knowledge of marketing

…all of it leads me to clearer thoughts, more motivation, fewer excuses, and more execution.

He inspired me to read the book, “Meditations” by Marcus Aurelias (specifically, he recommended The Modern Library version). Maybe a book by a Roman emperor sounds like it would be a bit, well, dated, but I was blown away by how applicable those ancient thoughts are to our lives today.  I’ve been fascinated by the Roman Empire ever since I visited Rome when I was in college, but I can’t say I would have read “Meditations” if not for Ryan Holiday.

I will continue to follow Ryan closely. He is someone that keeps me refining myself and my business. Holiday is a leader who has been a big part of my growth—even if we’ve never actually met.


Want to meet other entrepreneurs? Listen to our podcast, Entrepreneur Perspectives on Spotify, Stitcher, or Apple.

Image of Ryan Holiday was taken by ryan_holiday under the Creative Commons Attribution-ShareAlike 2.0 License.