- The Pen Pivot
- Posts
- Ryan Holiday's Content Empire - The Daily Stoic
Ryan Holiday's Content Empire - The Daily Stoic

Welcome to The Pen Pivot!
At 9am (EST) every Monday, Wednesday, and Friday, we show content creators how to use produce better content, faster.
We’re trying a new format today.
We love sharing great tools with you.
But we also want to show you how great creators turn content into giant businesses.
So we’re toying with deep dives and breakdowns showing you how they do it.
Let us know what you think of the new format using the poll at the bottom.
Enjoy!
In today’s email:
Creator Of The Day 🎨 - Learn exactly how The Daily Stoic turns its content machine into millions of dollars per year.
Tool Of The Day 🛠️ - A tool to create an automated social media content calendar for you and your business.

-CREATOR OF THE DAY-
THE DAILY STOIC
The Daily Stoic is a masterclass in content monetization.
1.4 million YT subscribers
2.5 million IG followers
515K Twitter Followers
700K newsletter subs
In a niche that was barely heard of 5yrs ago.
You’re about to learn six ways this content empire turns content views/impressions into millions of dollars per year.
Use it as inspiration for your own content and turn your traffic into a full-time income.
Quick Summary:
The Daily Stoic is a media company that produces written, video, and audio content on the ancient philosophy of stoicism.
Meditations, musings, interviews, and more.
Its USP?
It focuses on how to apply it to modern life.
But how does a mindset/philosophy media company generate millions of dollars?
1. Books
Ryan Holiday - founder of The Daily Stoic - is a best-selling author.
All of the content drives traffic to the Daily Stoic Store where all of his physical books are for sale.
The books are very closely aligned with the content itself - they're all related to modern stoicism.
The more closely aligned your products are with the content that drives the traffic, the higher your conversion rates will generally be.
The pricing architecture of books for sale is also interesting.
You've got the option of buying a simple signed copy at a low price point.
As well as the option of buying a leatherbound edition at a premium.
You can also buy an 8-book bundle at a discount.
Give your audience options.

2. Physical Products
The products for sale in the Daily Stoic Store are mind-blowingly creative:
• Jewelry - pendants, rings, and medallions with stoic emblems/quotes
• Stoicism-themed calendars and prints
• Busts of stoic philosophers
• Journals
It’s a perfect example of how you can create products in any niche when you know your audience.

3. Digital Products
There are currently 9 digital courses for sale in The Daily Stoic store
$25-$99
Each one focuses on a different aspect of improving life with stoicism.
They include:
• Q & A Sessions
• Interviews with experts
• Exclusive email content
And more.
Digital products have higher margins and generally require less effort than physical products.
4. Membership program
For $249/year you get access to Daily Stoic Life:
• Ad-free, exclusive email content
• Access to a private community platform
• Discounts in the store
• A hardcover book on stoic wisdom
• Access to all courses
A very small proportion of your audience will be willing to pay you annually for access to additional value.
People love feeling as though they’re part of a like-minded community.
They’ll happily pay for the privilege.
Recurring revenue from superfans.
5. YouTube AdSense
With 1.4m subscribers and 2 x uploads/week, The Daily Stoic will easily be making 5 figures/month just from ads.
Some large creators choose to turn ads off.
But this is significant revenue to pump back into content and product creation.
6. Live shows
The latest YT videos drive traffic to a landing page for ticket sales.
Ryan Holiday's speaking events.
This won't be practical or valuable until you've built an established brand.
But boy can speaking engagements be lucrative.

Funneling Traffic Into Monetization Methods
There are 2 broad methods the Daily Stoic uses to funnel traffic toward these monetization methods:
• Direct links from content (eg. in YouTube vid descriptions)
• Content grows the email list → email content nurtures subscribers → emails contain links to monetization methods
Key Takeaways:
• Diversify - every niche has unique opportunities for monetization
• Build trust by being everywhere
• Be relentless with content
• Vary the price points. "Premium" fans will pay for extra value
• Own the audience and build a giant email list
Do you want more deep dives into how great content creators build their businesses? |

-TOOL OF THE DAY-
SOCOCAL
(Not sponsored)
Generate an automated 30-day social media content calendar based on your content objectives.
Quickly plan, create, and schedule social media content with its series of AI-powered tools and features.
Take the friction out of social content creation with automation and AI.
And that’s all for today!
See you next Wednesday 😃
Misya, The Pen Pivot