Issue 4: Ryan Holiday

17 min read

Tiny Digital Worlds and Open-World Marketing is as much a mindset as it is a framework of principles that stack on top of each other to produce an emergent outcome other 1 than the individually connected parts.

Because we will all “stack the bricks” of our Tiny Word differently, the expression of what we build will always be as unique as our fingerprint.

There is, therefore, no objectively “best” or “correct” way to build our Tiny World. In the same way, every painter, even when using the same paints and canvas, will produce masterpieces that are vastly different, speaking in the vocabulary of their unique perspectives and worldviews.

Each brushstroke, every choice of hue or texture, embodies a decision based on individual experiences, tastes, and narratives.

In the realm of Tiny Digital Worlds, our “palette” comprises our unique stories, the emotional connections we forge, and the rich, serialized narratives we craft to engage our audience.

Like the painter’s finished canvas, our Worlds are a manifestation of our ethos, a living tapestry that evolves over time, ever-responsive to the needs and desires of those who inhabit it.

And just as no two masterpieces can be meaningfully compared, each Tiny World stands as its own testament to the infinite diversity of human creativity and connection.

As I share my best thinking in these essays and email series, my aim is twofold.

First, I’m codifying the principles of Tiny Digital Worlds, enabling you to either intuitively grasp the concept (and build your World) and/or become an official Tiny World Builder (a paid membership tier that will be available in early 2024). Here, we will cultivate these Worlds collaboratively among like-minded peers.

Second, within some of these Tiny World Newsletters, I also spotlight businesses that, albeit unknowingly, resonate with the ethos of Tiny Digital Worlds, serving as compelling case studies that illuminate the versatility and universal appeal of this approach.

Today, I aim to explore the expansive world Ryan Holiday has meticulously crafted over the past decade or more.

The examination will unfold in three parts: an initial look at the backstory, an analysis of the key components that constitute Ryan’s “world,” and a concluding reflection that isolates both the less successful and most effective aspects, as observed through the lens of Tiny World principles.

It’s vital to clarify that my intention is not to pit my initiatives against Ryan’s but to offer a nuanced spotlight on his efforts.

While doing so, I’ll point out specific elements that resonate with me or fall short from a subjective standpoint.

1. Backstory: Ryan Holiday

Ryan is an author (of about 14 books to date) and modern-day Stoic.

Websites: ryanholiday.net, dailystoic.com, dailydad.com, and thepaintedporch.com (Bookshop in Austin, Texas).

I’ll start with some backstory for context before I look at what Ryan is doing through a Tiny World lens to the degree I can as an observer.

I don’t know Ryan personally, and we’ve never communicated, or I would likely have more nuances to share.

Ryan’s claim-to-fame, where he first made a big splash in 2012, is his work on “media manipulation,” basically how news and media can be “gamed” for exposure. (Trust Me, I’m Lying: Confessions of a Media Manipulator.)

I own a few of Ryan’s books and have always enjoyed reading them.

While I own ‘Trust Me, I’m Lying,’ I’ve never read it. According to Amazon, I purchased it on July 26, 2012 (I think the cover and subtext of the subtitle grabbed me back then).

My favorite book is probably Perennial Seller: The Art of Making and Marketing Work that Lasts (2017), which I purchased on July 20, 2017.

It’s a book that draws attention to many of the principles I hold dear, like building something people will continue buying or engaging with for years.

(The insights I remember: Aim for longevity from the get-go, quality over quantity, master the 1,000 True Fans concept, and build “a platform” you own that opens up a direct relationship with your audience.)

But I also enjoyed reading Conspiracy: Peter Thiel, Hulk Hogan, Gawker, and the Anatomy of Intrigue about the lawsuit between Gawker Media and wrestler Hulk Hogan, as well as Peter Thiel’s involvement in the dispute, which I found fascinating (take away: don’t mess with a billionaire! especially someone as strategically patient as Thiel).

My critique of Ryan is that he’s a brilliant distiller, “translator,” and interpreter of the works of others (ancient philosophy, with a focus on Stoicism), helping us understand ancient wisdom in a way that is relevant and applicable to our lives.

I don’t believe he’s an originator of novel ideas. This is not criticism. He’s exceptionally talented at drawing on the wisdom of ancient philosophers, such as Epictetus, Seneca, and Marcus Aurelius, providing his own insights and commentary.

There’s a real skill in taking age-old ideas and making them accessible and relevant to people today. He packages these ancient concepts in a way that’s easier to digest and apply, which can be helpful for modern readers who don’t care about reading the dense works of ancient philosophers.

2. Non-DRM Perspective

(DRM is the acronym for direct-response-marketing.)

On March 7, 2023 (the day I turned 50!), Ryan published an article, This Decision Changed My Life and My Business, an excellent place to start this journey.

“I used to spend six figures a year on Facebook ads for Daily Stoic.”

It’s a short read, and it’s worth reading for context. (Ideally, do it now and then come back.)

Ryan opens by framing how some authors he knows spend upwards of $20,000/month on publicists or co-ops (to get extra prominent placement at airport bookstores).

Ryan recognized that spending money on advertising, even though he was getting a positive ROI, would amount to absolutely nothing the moment he turned off the advertising spigot.

Someone gets shown an ad and buys something, that’s great. But the people who get shown an ad and do nothing? What a lost opportunity! What a waste of their time and yours.

There are two ways of looking at this, of course. I’ll play devil’s advocate from both perspectives.

Most die-hard paid media experts and agencies would say, “If you’re putting in a buck and getting back more than a buck, don’t stop! That’s free money and customers.”

I can see the logic of the argument. But I can also see the perspective Ryan is making.

Of course, I have no idea what his ROI was. 120% is perhaps a safe guess based on his sites and the tiny margin on book sales.

A 120% ROI would equate to, using the $20,000/mo quoted, a $24K return. Or $4K/mo in profit, excluding any costs associated with managing the ad spend.

So, less than $4K indeed.

Spending $20K/month and paying an agency or employee leaves little room for profit, and it’s likely a break-even affair at best.

As Ryan implies, there’s an opportunity cost in doing this. So why not allocate those resources to creating something more enduring? This is a strategy that resonates with me.

Ryan goes on to say:

But several years ago I made a decision that changed my business and radically transformed my career.
I stopped spending money on all of that.
So I took that money and did something very different with it: I used it to start making stuff.

Taking the money he was spending on advertising, he hired people to create content — videos, articles, emails, etc.

“Some people might shrug and say, ‘Yeah that’s called content marketing,’ but it’s actually a deeper philosophical shift,” says Ryan.

The “deeper philosophical shift” Ryan implies, I believe, boils down to creating and owning the “thing” that’s permanent and valuable, that people can find and read or watch, and for it to have an impact, moving them closer to Ryan’s “Rome.”

(While I touched on the concept of “Rome” in email 3 of my welcome series, I’ll go much deeper into my idea of “Rome” in a future newsletter because it’s a fundamental and powerful concept within a Tiny World.)

However, as I’ve drawn attention to in Issues 2 and 3 of this newsletter, the dynamic that differentiates ‘content marketing’ from ‘world-building’ is the transformative experience embedded in the narrative arc of a World. The underlying themes we create for our citizens to find and experience.

Most ‘content marketing’ I see (and can’t bring myself to read most of the time) is shallow, one-dimensional perspectives that do little more than scratch the surface of an idea, let alone offer anything worth taking notes about.

When we thoughtfully add content “lego bricks” to our World, expanding it and our embedded themes, we create opportunities for people to find doorways into our World. This is a powerful expression of leverage.

I could stop making new content today … I could die tomorrow and the stuff we have made would keep on keeping on, reaching people, helping people. And this is really the best part.

While Ryan never mentions the concept of “world-building,” he discovered an expression of world-building — or, rather, open-world marketing.

3. RyanHoliday.net

WordPress powers RyanHoliday.net. His theme design, however, is unimpressive.

Ryan’s efforts seem impressively unimpressive after seeing how slick James Clear’s website design is (a custom theme built by Rafal Tomal, a very impressive designer).

One of my Tiny World principles is that design matters — or perhaps stated another way, our design contributes to the message our “city” says to our inhabitants.

It’s hard to excuse poor design in the era we operate in today.

His site has all the elements I expect to see linked in the navigation.

Putting design aside, his home page showcases the parts he wants to draw attention to, with an obvious priority in enticing people to join his email list (which I’m inferring is Ryan’s “Rome”).

Ryan maintains an active blog. Based on my analysis, he has around 3,800 pages in total, which is what I would expect for a site of this age (2007) from someone who is a prolific writer.

Ryan started building this email list when he recognized people were interested in his book recommendation, so in 2008, he created a “private email list,” which he notes on his subscribe page.

After being asked this question a thousand times, I put together a private email list of book recommendations. Each month, I send one email with 5 to 10 amazing books that I read, reviewed and think you’ll like. The email is simple and quick and that’s why its grown to become the sensation its become since 2008.

I found a LinkedIn article by Ryan, published on July 21, 2017, about how he built his platform to 80,000+ subscribers.

At the time, Ryan was using MailChimp for RyanHoliday.net and ConvertKit for the DailyStoic.com email. I can imagine this wasn’t ideal because, no doubt, he has many overlapping subscribers across the two brand domain lists.

He’s since moved everything to ConvertKit.

What I don’t like:

As noted, his design is unimpressive.

There’s no design continuity between his two main brand domains. Unless, of course, Ryan intentionally wants RyanHoliday.net and DailyStoic.com to be so jarringly different.

While there is an argument to be made that he does have “one world” containing two separate overlapping brands, from a visitor’s perspective, it feels more like two distinct “worlds.”

Someone can land on RyanHoliday.net and remain clueless about DailyStoic.com. Until they click an email or nav link that redirects to the other domain, which looks very different and, I suppose, for some, can feel jarring.

More about Ryan’s World a little later.

What I like:

At the end of each year, Ryan compiles a recap of the best books he’s read that year. On his subscribe page, he directly links to these lists (articles) going back to 2011.

I like this because it aligns with one of my ‘open-world’ principles of freely expanding our world without the need/requirement for someone first to subscribe.

Someone can one-click, read one or more list compilations, and then decide whether they go “all in” and subscribe (perhaps now with a better email address — their primary/personal one — not a throwaway one).

4. DailyStoic.com

DailyStoic.com was launched in the fall of 2016.

This site is much the same as RyanHoliday.net but with a slightly nicer design.

DailyStoic.com doubles up on what RyanHoliday.net does.

There’s another active blog and another active email subscription (this time with the addition of his paid membership, Daily Stoic Life, for $249, then $99/yr after that).

DailyStoic.com is also the “home” of his Daily Stoic Podcast and (Shopify) Store for courses and special edition signed books (RyanHoliday.net links to both).

The bullseyes for all of Ryan’s properties are his email lists (his “Rome”). In a case study on ConvertKit, Ryan said, “The Daily Stoic newsletter is the product.”

Email is his way of delivering oversized value to his subscribers, not to sell to them. This aligns with another principle of Tiny Digital Worlds, where sales are an emergent property of fostering relationships first.

Part of what makes the content so relevant is that Ryan divides it up based on how familiar and interested his subscribers are in his work.

His subscribers come from all over the world, and for many, his website is the first time they’re learning about stoicism.

“What frustrated me about a lot of the philosophy writing out there, particularly on Stoicism, is the writer assumes all sorts of interest and knowledge on behalf of the reader that usually isn’t there,” says Ryan. “I’m a nerd about philosophy, but I try to meet people where they are.”

A ConvertKit tweet from March 24, 2021, points to a case study from which a screenshot of Ryan’s ConvertKit account is shared.

It’s unclear whether this is the subscriber count of RyanHoliday.net and DailyStoic.com or just one.

I can’t see the logic of managing two separate CK accounts, which would be wasteful insofar as paying for thousands of duplicate subscribers. So, I suspect this is both.

175K in Jan 2020 and 315K at the end of that year. That’s impressive!

I can’t find any more recent data, but it’s not hard to imagine he’s breached a million subscribers by now, or very close (2023).

5. DailyDad.com

This seems to be Ryan’s newest brand.

It follows the same formula as his two main brands. As with the others, the primary focus is to drive people to join his email list — “the product,” using Ryan’s previous framing.

There’s a blog, another (Shopify) store, and a landing page that points to a $41 course, “The Parent-To-Be: A Daily Dad Parenting Challenge.”

6. Traffic

Paid:

Because I have no insider information, everything here is inferred and speculative, so I’ll keep this to broad strokes.

We know Ryan’s doesn’t pay for traditional advertising (like FB ads), based on the article I cited from March 7, 2023.

But what we do know is that he’s been using The Creator Network (also see here) by ConvertKit with great success:

“The Creator Network is now driving more new subscribers for Daily Stoic than all our other traffic sources combined.”

(I’ll talk more about The Creator Network in a future newsletter, a channel I’ll use once my paid tier — Tiny World Builders — is live.)

Books:

Ryan has sold millions of books that distill the wisdom of ancient philosophers such as Epictetus, Seneca, and Marcus Aurelius. These books are perennial sellers and will likely remain relevant indefinitely.

So, it’s easy to infer that his books drive a significant portion of new, well-qualified awareness to his sites.

Books, specifically those timeless treasures that address our inherent human needs and desires, act as “engines” of awareness, “conduits” into our Worlds.

It’s a beautiful, elegantly simple system — earning royalties on one side of the coin and driving some significant percentage of his readers into his “worlds” and onto his email lists, on the other side, where those relationships are closer, more direct, and personal.

Social:

Across all the socials (YT, Twitter/X, IG), Ryan has millions of “followers” and “subscribers” he can leverage to the degree the platforms allow within their ever-throttling algorithms.

He maintains separate social media accounts for DS, RH, and DD.

SEO:

This is something that just (mostly) happens, an emergent property of expanding a World that’s indexable to the search engines.

I doubt Ryan thinks much about this. With around 3,800 pages on RyanHoliday.net and 1,400 on DailyStoic.com, this happens organically.

It’s gravy like it should be.

Looking at his page code, it doesn’t look like he is using an SEO plugin like The SEO Framework (my preference). But I see Open Graph meta tags, snippets of code that control how URLs are displayed when shared on social media.

Ryan’s theme code is a bloated mess, and load times and page size are reflected poorly on both Pingdom (results) and Google PageSpeed Insights (results).

As with thoughtful design (choosing a performance-optimized theme engine like GeneratePress and GenerateBlock as one’s design canvas over an “off the shelf” mass market theme), there’s no excuse for poor website speed results, as blazing-fast WordPress-optimized managed hosting is inexpensive and widely accessible (I use Rocket, which costs between $30 – $100/mo depending on needs).

Ryan may be on decent hosting. I can’t tell because Cloudflare is obfuscating the upstream host. But his theme is undermining his overall performance.

There are structural improvements Ryan can make that will dramatically improve the visitor experience, affording better opportunities for people to discover relevant CYOA (choose your own adventure) content.

I’ll briefly touch on this next, but a deep dive into the structure of a World will be for another time (and one of the areas of emphasis within Tiny World Builders).

Visitors:

On Wednesday, December 8, 2021, Amazon announced the cessation of its website ranking and competitive analysis service, which has been available to the public for more than 25 years.

Similarweb seems to have filled the void, so I’ve used their service to get a “sense” of visitor volume to Ryan’s two main brands.

I do not know how accurate these stats are, but the data is likely directionally useful, especially when comparing other sites (which I’ve added for context).

• ryanholiday.net (Global Rank: #209,917 / Total Visits: 259K)
• dailystoic.com (Global Rank: #47,006 / Total Visits: 1.7M)
• dailydad.com (Global Rank: #723,546 / Total Visits: 73.7K)
• fs.blog (Global Rank: 55,781 / Total Visits: 1.4M)
• jamesclear.com (Global Rank: 34,926 / Total Visits: 2.3M)
• tim.blog (Global Rank: 23,556 / Total Visits: 3.7M)
• digitalmarketer.com (Global Rank: 208,286 / Total Visits: 256.4K)
• every.to (Global Rank: 155,071 / Total Visits: 368.1K)

Note: The stats above change daily. The links are live, so they will reflect higher or lower values from what I have here.

7. Ryan’s Tiny World

Looking at archive.org (Wayback Machine), Ryan’s two main brands have moved through a spectrum of iterations from their inception till now.

My assessment is based on having no insider insights into Ryan’s business decisions. Strategy is mostly “invisible” when looking in from the outside.

I suspect that when Ryan decided to launch dailystoic.com, it wasn’t a trivial decision to determine if it should be a separate brand and domain, even when this seems to be a favored option of his.

I was the same in the mid and late 2000s. I started with AndreChaperon.com, then picked up AffiliateBully.com (I cringe at that domain name now), then AutoResponderMadess.com as the home of my premier email course, and later, SphereofInfluence.io for Sphere of Influence (and many other domains).

It wasn’t until 2015 that I decided to go the other way and consolidate everything within one brand domain … a single World for everything. The move took about two years. None of this shit is easy to move.

I’ve drawn a World Map for Ryan’s “worlds.” The sizes roughly represent the percentage of traffic each domain receives.

While multiple “worlds” work, my preference, for reasons I’ll unpack in more detail some other time, is to use a single domain to represent a World.

When our “stuff” primarily serves the same audience (or a significant overlap), breaking out our worlds into separate pieces can, on balance, be a net negative.

I believe there to be significant usability benefits to having a single “world,” as well as logistical, technical, and from a search engine perspective.

One of the structural components missing from all of Ryan’s sites is “silos” (or “hub pages”) from which thematically similar content is clustered, making it easier to find and browse.

What I know about Stoicism can fit on the back of a napkin, so I will use a different example to demonstrate what I mean.

The business and learning I care about can probably be broken down into categories like this, for example:

• Decision Making
• Creativity
• Productivity
• Self-Improvement
• Mental Models
• Learning

(Etc, etc.)

Think of these as well signposted “archways” that lead off a common Town Square. Once someone self-selects an archway from which they want to explore further, more specific “doorways” can be opened and entered — an article or essay is one expression of a doorway.

While Ryan’s blogs have categories, they’re incredibly hard to find and certainly don’t represent accessibly “signposted archways.” I found nowhere to see what all his categories are.

8. Conclusion

“Every action is a step toward the short game or the long game. You can’t opt out, and you can’t play a long-term game in everything. You need to pick what matters to you. But in everything you do, time amplifies the difference between strategies that work in the short term and ones that work in the long term. The long game allows you to compound results. The longer you play, the bigger the rewards.” (Source.)

Ryan’s “Rome” — the “product” using his language — are his email lists (across various domains). It’s not apparent to me why RH and DS are separate domains, brands, and email lists.

When there is a long-term strategic advantage to moving/consolidating brands, going through the pain of doing this can be a worthwhile endeavor.

Because RyanHoliday.net came first and Ryan, after all, runs a personal brand, it makes sense that his domain name represents the North Star of his World, with DS being a subset of it.

• RyanHoliday.net
• RyanHoliday.net/daily-stoic/

(DailyStoic.com could 301 redirect to the above page, so it could still be used as a CTA in podcast interviews and book blurbs.)

I can also make a case to add DD.

• RyanHoliday.net/daily-dad/

This is the route James Clear has taken:

• https://jamesclear.com
• https://jamesclear.com/atomic-habits

… where AtomicHabits.com is a 301 to the above Atomic Habits page. It’s elegantly simple.

Ryan is also paying for and managing multiple Shopify stores, which could be consolidated, offering better cross-selling opportunities.

When thinking about a single World/domain vs. Worlds spread over multiple websites, a primary consideration is user and customer experience for our “citizens.”

If the audience across the “brands” is essentially the same (a significant overlap), having a single World makes the most sense. I believe RH and DS share an audience — Ryan being the central character.

(There is an argument in favor of an author who writes in both fiction and nonfiction genres and uses different pen names to keep their work separated across various websites, thus creating multiple Worlds.

I wonder: If the internet existed during George Orwell’s time, he might have maintained a personal blog about writing craft under his real name, Eric Arthur Blair, at EricArthurBlair.com.)

The aspects of any World that are immediately perceptible — what I’ve highlighted here as the “outer world” — represent only the tip of the iceberg, so to speak. They are the external markers that can be observed and analyzed, as I have done to the degree I can.

Beneath this surface layer lies the “inner world,” a curated narrative space that acts as the cradle for transformative experiences (see newsletter issues 2 and 3). It’s here where powerful tools like tailored narrative-driven email sequences come into play, enabling us to forge more intimate and direct relationships with our audience.

Operating within a single, unified World can simplify this complexity.

However, it’s crucial to remember that what we see — these tactics — are governed by underlying strategies, often opaque to external observers.

Thus, while I’ve dissected elements of Ryan Holiday’s world, I acknowledge the hidden decision-making processes that are inevitably at play and invisible to us looking in from the outside.

André