How Fortune Favors the Brave with Ryan Holiday

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Ryan Holiday

How Fortune Favors the Brave


What can principles that were written over 2,000 years ago teach us about today? I think they can teach us A LOT. There’s a reason why stoicism has been around for so long, and played a critical role in the development of leaders like Teddy Roosevelt, some of the world’s top CEOs, and even NFL coaches like Pete Carroll. Stoic principles help us understand what we can and can’t control, how to better perform under pressure, how to live a life of high integrity, and so much more. At its core though, stoicism teaches us the timeless truth of why we should be a person of virtue.

And now, thanks to people like my guest today, stoic philosophy is seeing a massive resurgence. It’s a great time for it too. Burnout and overwhelm are on the rise, and it seems harder than ever to unplug in today’s world. Stoicism helps us slow down, be deliberate with our actions, and intentional with our life’s purpose.

In today’s episode, Ryan will tell us how stoicism can be the key to building wealth, finding inner peace, and developing discipline. I’m so excited for you to listen to it and I think you’ll walk away with lessons you can apply to your life today. Now, please help me welcome back the one-and-only Ryan Holiday to The School of Greatness!

“Fear could be a sign that you’re on the cusp of something. Fear indicates growth.” @ryanholiday  

Ryan Holiday is a best-selling American author, public-relations strategist, bookstore owner and host of the podcast The Daily Stoic. He is a former director of marketing for American Apparel.

If you’re interested in learning how and why timeless stoic principles have helped SO many of the world’s most prolific thinkers and doers achieve their dreams, then this episode is for you. Whether you dive deep into the philosophy as a whole or just listen to this conversation, I’m confident you’ll gain value from it. Please join me for Episode 1,171 of The School of Greatness!

“All accomplishments are ephemeral. All that matters is what you do for the people you care about.” @ryanholiday  

Some Questions I Ask:

  • Why do you think it is so hard for people to face their insecurities, their shame, their fears, and their doubts?
  • What is something from the Stoics that everyone should learn right now to help them have more courage and live a greater life?
  • What is your thought process on reaching financial goals in the context of a philosophical point of view?
  • What would the Stoics be investing in?
  • What process did the Stoics use to heal anger and anxiety?
  • Where would you like to be a year from now internally?

In this episode, you will learn:

  • How fear is actually a good thing.
  • Why people struggle to have courage and how to overcome that.
  • Why thinking about our own mortality can help us rather than hurt us.
  • The biggest lessons we can learn from stoicism when it comes to finding peace, wealth, and developing discipline.
  • And much more…
Connect with
Ryan Holiday

Transcript of this Episode

Music Credits:


Kaibu by Killercats

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