Ryan Holiday returns to discuss Wisdom Takes Work — a conversation about learning, humility, and the difference between knowledge and wisdom. James and Ryan explore why AI can’t teach judgment, why doing hard things matters, and how practicing curiosity can lead to a wiser, more meaningful life.
Sep 30
Bill O'Reilly on Brokering a Secret Hostage Release Deal
Two weeks after one phone call, four hostages walked free from Gaza...A Note from James:After the election, before Trump was sworn in for his second term, Biden’s national security team needed to reach the president-elect about the hostages in Gaza.According to Bill O’Reilly, the ... Show More
33m 8s
Oct 2025
Stoicism’s Lessons on Becoming Wise - Ryan Holiday - #1001
Ryan Holiday is a podcaster, marketer and an author. If intelligence were enough, the smartest among us would also be the wisest. Yet time and again, they stumble over life’s simplest lessons. Wisdom isn’t about knowing more; it’s about seeing deeper. So how do we shed the illusi ... Show More
1h 52m
Nov 2024
Ryan Holiday: How to Win the War with Yourself
Ryan Holiday unpacks the subtle and not-so-subtle messages life sends us—and what happens when we ignore them. From mismatched tattoos and injured ankles, Ryan reflects on the lessons he’s learned about preparation, awareness, and humility. Using examples ranging from personal mi ... Show More
1h 43m
Mar 2021
Stoicism and Celebrating Success ft. Ryan Holiday
Ryan Holiday is a media strategist and the author of ten books including, The Obstacle Is the Way, Ego Is the Enemy, The Daily Stoic, Conspiracy, and Stillness is the Key. He joins Scott to discuss how the four virtues of stoicism (courage, temperance, justice, and wisdom) are in ... Show More
1h 7m
Aug 2023
The Discipline Expert: The 4 Surprising & Easy Habits ALL High Achievers Have! (Based On 2,000 Years Of Research) - Ryan Holiday
How can a 2,000 year old philosophy change your life in 2023?
In this new episode Steven sits down with the bestselling author Ryan Holiday. Ryan is best known for promoting the timeless life philosophy of Stoicism through his books, ‘Ego Is The Enemy’, ‘The Obstacle Is The Way’, ... Show More
1h 21m
Oct 2025
Stoicism (ft. Ryan Holiday), Solved
What does it actually mean to live like a Stoic? In this wide-ranging conversation with bestselling author and modern Stoicism evangelist Ryan Holiday, we unpack the origins of Stoic philosophy, why it exploded during turbulent times in ancient Greece and Rome, and how its princi ... Show More
2h 53m
Dec 2024
Ryan Holiday: Why I'm Embracing Death in 2025 (E316)
<p>Ryan Holiday is a bestselling author and expert on stoic philosophy, known for his books like ‘The Obstacle Is the Way’ and ‘Daily Stoic’. Through his work, he helps others apply ancient wisdom to modern-day challenges, exploring themes like discipline, perseverance, and self- ... Show More
54m 28s
Aug 2024
Ryan Holiday Wants You To Do The Right Thing, Right Now
Ryan Holiday is a renowned author, modern Stoic philosopher, and the driving force behind the resurgence of ancient wisdom in contemporary culture. This conversation explores the intersection of Stoicism and Ryan’s iconoclastic perspective on personal ethics, which emphasizes act ... Show More
1h 51m