How Ryan Holiday Built a Million Dollar Content Empire | 107

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Dec 11, 2025

Ryan Holiday, a bestselling author and media entrepreneur behind Daily Stoic, shares his secrets to building a content empire without ads. He discusses how to make genuine, engaging content and leverage algorithms for wider reach. Ryan reveals the power of transforming personal experiences into multi-format content and creating a content flywheel for maximum efficiency. He emphasizes the importance of nurturing curiosity in children and balancing creativity with commerce. Dive into his insights on crafting timeless, impactful narratives that resonate across platforms.

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ADVICE

Replace Ads With Valuable Content

Replace paid ads with content that people want to find because content provides long-term, valuable discovery.
Invest resources into making useful content instead of microtesting ads that users skip.

INSIGHT

Meet Audiences Where They Are

Design content to meet people where they already are so algorithms surface your work for free.
Use platforms’ strengths to translate deep ideas into accessible formats for new audiences.

ADVICE

Build Multiuse Content First

Create one primary piece that can be repurposed across formats to maximize ROI on time.
Turn long-form work into articles, clips, social posts, and other assets automatically.

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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

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Learn more about the podcast: https://nathanbarry.com/show

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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