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 missteps to famous entrepreneurial gambles, this episode is a deep dive into the a ... Show More
Yesterday
Michael Ovitz: The Business of Relationships
Michael Ovitz co-founded CAA and helped reshape Hollywood, then took the same playbook into tech investing and advising founders. In this conversation, he breaks down the operating rules that kept CAA from losing clients, and the personal disciplines that kept him grounded when t ... Show More
1h 36m
Jan 27
How McDonald’s Took Over America | Ray Kroc [Outliers]
Ray Kroc turned McDonald’s from a single roadside restaurant into a system built to scale. At 52, after decades selling paper cups and milkshake machines, he opened the first McDonald’s in 1955 and helped grow it to nearly 8,000 restaurants worldwide. This Outliers episode breaks ... Show More
50m 20s
Jan 20
Morgan Housel: Wealth is What You Have Minus What You Want
Morgan Housel breaks down the exact framework he uses to build wealth, minimize financial stress, and buy freedom. While most financial advice focuses on how to get rich, Morgan explains why the skills needed to stay rich are completely different. You will learn why "boring" inve ... Show More
1h 57m
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
Sep 2024
Ryan Holiday: Why You Need to Reparent Your 14-Year-Old Self & How to Overcome the Fear of Not Being Good Enough
<p>What would you tell your 14-year-old self?</p> <p>How do you quiet the “not good enough” voice?</p> <p>Today, Jay welcomes Ryan Holiday, renowned philosopher, bestselling author, and host of The Daily Stoic. With over 10 million copies of his books sold globally, R ... Show More
1h 29m
Oct 2025
3760: Sangfroid: The Art of Being Cool Under Pressure (and Success) by Ryan Holiday on How to Be More Composed
Discover all of the podcasts in our network, search for specific episodes, get the Optimal Living Daily workbook, and learn more at: OLDPodcast.com. Episode 3760: Ryan Holiday explores the timeless virtue of sangfroid, the art of keeping calm under pressure, and how it has shaped ... Show More
10m 33s
Oct 2024
Ryan Holiday on How Stoic Principles Can Help You Thrive in Modern Society
"How Do You Master Stillness in a World of Chaos?" In this inspiring episode, I sit down with one of the brightest minds in modern-day philosophy, Ryan Holiday. Together, we explore the wisdom behind Stoicism and how its timeless principles can help us navigate through the chaos ... Show More
55m 54s
Dec 2024
Consumerism, Guilty Consciences, and Crippling Anxiety | ASK ME ANYTHING
<p>In this episode of Ask Me Anything, Ryan Michler and Kipp Sorensen dive into a candid discussion about the relentless cycle of consumerism, exploring how modern holiday traditions have strayed from their meaningful roots. They share insights on battling guilt when taking perso ... Show More
1h 22m
Dec 2024
How to STOP Living in Fear and Find Your Purpose in Life | Ryan Holiday : 1236
<p>Fear is quietly running your life—and it’s holding you back from the purpose and success you deserve. In this episode, we revisit Dave chatting with one of the keynote speakers for the Biohacking Conference 2025, Ryan Holiday, the bestselling author of <em>Courage Is ... Show More
1h 15m
Sep 2024
Turning Trials into Triumph: Ryan Holiday (The Daily Stoic)
Can ancient philosophy be the key to modern success? Ryan Holiday, a leading thinker of his generation, believes so. From NFL quarterbacks to corporate CEOs, many credit Holiday's work with introducing them to the transformative power of Stoic philosophy. In this episode, Ryan ta ... Show More
48m 34s