Ryan Holiday: Think Like a Stoic, Timeless Leadership Principles for Modern Entrepreneurs | Leadership | YAPClassic

Young and Profiting (YAP) with Hala Taha: Entrepreneurship and Self-Improvement PodcastFriday, July 24, 2026

Show Notes

Ryan Holiday's approach to leadership was shaped through patience and years of unglamorous work. After dropping out of college at 19, he apprenticed under bestselling author Robert Greene, learning writing, research, persuasion, and human nature before becoming the marketing director of American Apparel at just 21. Those experiences laid the foundation for his rise as a bestselling author and one of the world's leading voices on Stoicism. In this episode, Ryan shares how Stoicism can help entrepreneurs strengthen leadership skills, sharpen decision-making, and maintain a resilient mindset during tough times.

In this episode, Hala and Ryan will discuss:

(00:00) Introduction

(01:32) Robert Greene’s Influence on Ryan’s Career

(09:52) Provocative Marketing Lessons From American Apparel

(18:18) Ryan’s Path Into Stoic Philosophy

(19:44) The Stoic Approach to Life and Business

(27:13) The Four Stoic Virtues for Personal Development

(32:21) Mastering Clear Decision-Making Under Pressure

(38:18) The Dangers of Ego in Leadership

(40:34) How Stoicism Drives Productivity

(41:52) Building Ethical Habits and Leadership Skills

(50:41) Stoic Habits for Profiting in Life

Ryan Holiday is a bestselling author, entrepreneur, media strategist, and one of the leading modern voices bringing Stoic philosophy to mainstream audiences. He served as director of marketing at American Apparel before founding his creative agency, Brass Check. Ryan’s books, including The Obstacle Is the Way and The Daily Stoic, have sold more than 2 million copies in 30 languages. His work helps leaders and creatives apply Stoic principles to overcome challenges.

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