How Ryan Holiday Built a Million Dollar Content Empire | 107
The Nathan Barry Show
Saying yes early, learning to say no later
Nathan and Ryan discuss the value of saying yes to opportunities early and the later skill of saying no strategically.
The secret to building a content machine that reaches millions, all without spending a dime on ads? According to Ryan Holiday, it starts with making content people actually want to consume. In this live interview from Austin, Texas, Ryan pulls back the curtain on how Daily Stoic went from an obscure philosophy discussed only in academia to a global phenomenon. From cultivating an audience one platform at a time to transforming a single piece of content into a multi-platform strategy, discover the counterintuitive lessons from a master of timeless ideas and modern media. This isn't just about stoicism; it's a masterclass in building a resilient, impactful career designed to stand the test of time.
Timestamps:
00:00 Building a timeless content machine
02:17 Why ditch every ad and pivot to content?
06:07 The power of algorithms and meeting your audience where they are
08:27 Creating content you genuinely want to make
10:49 The Marathon video and turning experiences into content
13:26 Crafting a content flywheel that actually works
16:46 How a team translates one piece of content across mediums
20:09 What is a "pseudo event" and why do you need one?
24:21 From ghost town to content goldmine
28:47 Expanding your "set" beyond the studio
32:50 The value of "certification" in content creation
34:54 Lessons from Ghost Town Living's organic growth
39:46 How content creation impacts your life and thinking
42:36 Embracing different mediums, no matter your personal preference
45:11 Writing as a lagging indicator of deep work and research
47:53 Why AI can't replace the human touch in deep work
51:38 The process behind "Conspiracy": a narrative nonfiction deep dive
55:08 Parenting for wisdom: cultivating curiosity and deep dives
1:01:11 Navigating demand when starting out
1:05:06 Balancing art and commerce for long-term impact
1:08:52 The freedom of a profitable business
1:11:58 The ongoing challenge of discipline
If you enjoyed this episode, please like and subscribe, share it with your friends, and leave a review. I read every single one.
Learn more about the podcast: https://nathanbarry.com/show
Follow Nathan:
Instagram: https://www.instagram.com/nathanbarry
LinkedIn: https://www.linkedin.com/in/nathanbarry
X: https://twitter.com/nathanbarry
YouTube: https://www.youtube.com/@thenathanbarryshow
Website: https://nathanbarry.com
Kit: https://kit.com
Follow Ryan:
Website: https://ryanholiday.net
X: https://twitter.com/ryanholiday
Instagram: https://www.instagram.com/ryanholiday
LinkedIn: https://www.linkedin.com/in/ryanholiday
Daily Stoic: https://dailystoic.com
The Painted Porch: https://paintedporch.com
Featured in this episode:
Kit: https://www.kit.com
The Painted Porch: https://www.paintedporcom
Daily Stoic: https://dailystoic.com
Daily Dad: https://dailydad.com
Backroad Ventures: https://www.backroad.co
Ghost Town Living: https://www.youtube.com/@GhostTownLiving
Kit Studios: https://kit.com/studios
Highlights:
02:04 - From ads to in-house content creation
07:03 - People finding Ryan through the "algorithm" for free
12:25 - How one experience creates multiple content assets
20:51 - How a tuna recipe went viral for Matthew McConaughey
31:00 - The art of "certification" and making real life content come alive
46:57 - Why physical note cards are crucial for deep work
1:07:56 - Profit as permission to create more art
The AI-powered Podcast Player
