Hey There Modern Authors,
I’ve always admired people who play the long game.
Not just those who succeed, but those who stick around long enough to make success inevitable.
Because here’s the truth: in today’s viral, hype‑driven world, most people want platforms, not perspective. They want followers, not philosophy. They chase visibility instead of credibility.
And that’s why Ryan Holiday fascinates me.
He’s the rare modern author who’s done something almost impossible:
He’s made wisdom cool again.
Let's talk about how, and what all of us can learn from his unconventional approach.
The Work Behind the Wisdom
Most people met Ryan when The Obstacle Is the Way exploded into a phenomenon. NFL teams read it in locker rooms. CEOs handed it to their teams. Suddenly “Stoicism”, a philosophy older than Christianity, was trending.
But that book wasn’t lightning in a bottle. It was lightning in a lab.
Years before, Ryan was a 19‑year‑old apprentice to Robert Greene, the legendary author of The 48 Laws of Power. While his friends were chasing internships or influencers, Ryan was chasing craft.
He wasn’t posting threads. He was transcribing interviews.
He wasn’t optimizing for reach. He was learning the rhythm of research.
He wasn’t networking. He was apprenticing.
That word matters. Because apprenticeship is the opposite of modern attention‑hacking.
He spent seven years serving one master: the mastery of learning itself.
He learned how to research a book, how to structure a narrative, how to market without gimmicks, and how to build an audience around ideas instead of noise.
By the time Trust Me, I’m Lying launched in 2012, he wasn’t guessing how publishing worked. He’d built the machine from the inside.
That’s the first lesson for any aspiring thought leader: your apprenticeship is your advantage.
Before you can teach, you have to learn. Before you build an audience, you have to build understanding.
And quite honestly, the process of writing including learning from others, is too often lost on smart, savvy people.
From Experiments to Essence
When Trust Me, I’m Lying hit shelves, Ryan wasn’t yet the “Stoic guy.” He was a sharp, controversial marketer exposing how media manipulation worked.
Looking back, that book wasn’t a brand. It was an experiment.
He was testing voice, tone, and conviction — what every Modern Author has to do early on. He was asking the questions we all wrestle with:
Who am I writing for?
What do I actually believe?
What problem am I obsessed with solving?
And he followed that curiosity until it led somewhere timeless: Stoicism.
He didn’t choose Stoicism as a niche. It chose him as a category.
Over the next decade, he didn’t dabble. He devoted.
Fourteen books.
A daily email.
Multiple podcasts.
A physical bookstore in Austin.
A community of millions anchored by a single through‑line: philosophy that helps people live better lives.
That’s not a marketing campaign. That’s category creation.
He built a body of work so consistent that even if you forget his name, you remember his worldview.
They stand for something.
The Real Meaning of “Wisdom Takes Work”
Ryan’s new book, Wisdom Takes Work, is the fourth and final in his “Virtue Series.” It’s also the perfect metaphor for how true thought leadership actually develops.
He’s spent a decade walking the talk, showing what it looks like to make wisdom a practice, not a performance.
The idea sounds simple: knowledge is information; wisdom is integration.
But in a culture that rewards hot takes and shortcuts, choosing to do the slow, hard work of building a philosophy is an act of rebellion.
It’s easy to write once.
It’s hard to write again, and make it deeper.
It’s easy to have a viral moment.
It’s hard to build a timeless message.
When Ryan writes about virtue, he’s chasing truth, not trends.
Every book builds on the last. Every launch reinforces the same belief: we don’t need new tricks; we need ancient tools, applied well.
That’s the backbone of thought leadership.
You’re not here to say new things. You’re here to say true things in new ways.
I’ve seen this play out firsthand with my work on Super Mentors.
When I first started writing and speaking about modern mentorship back in 2020, I knew I was onto something. People lit up when they heard the phrase. The concept resonated. But I also knew: to make it stick, I’d need to live with it. Build with it. Teach it. Refine it. Commit to it.
It was actually my brother Mark who told me, "You don't have to have a business model behind the message. If the concept is valuable, it'll come."
So I did.
Three years in, I still feel like I’m just getting started. But something’s shifted. I’m hearing others use the language: career accelerators, mutual projects, relationship capital, door openers. I see people reference Super Mentors in workshops, client conversations, even social posts.
The best part? I didn’t need to go viral. I just needed to stay consistent.
Building a category like Super Mentors isn’t about clever branding. It’s about being willing to go deeper than anyone else. To keep shaping the belief, the system, and the community around it.
Ryan has spent a decade at the center of Stoicism’s modern rise. If I want Super Mentors to shape the next decade of modern careers, I know what it takes.
It's one of the things I often push back on when someone is interested in joining the Modern Author community:
"How fast is ROI? How quickly will I make the investment back? What's the guarantee?"
I know what it takes to build something... the greater the something, the harder it is to give certainty as to the timeline.
Work. Patience. And relentless commitment to the long game.
If you aren't playing that game tl build something that matters beyond the book, then maybe authorship isn't for you?
The Modern Author’s Apprenticeship
If you look closely at Ryan’s career, you’ll see that he’s been in a lifelong apprenticeship, first under Robert Greene, then Tucker Max, then under the Stoic philosophers, and now under the work itself.
I spent 18 months digging, hunting, learning, and apprenticing before I felt like I knew enough to contribute.
Every Modern Author should study that trajectory. Because it reveals the path so many skip.
- Apprentice the craft – Learn the process before you scale it.
- Experiment in public – Use your early books or content to find your voice.
- Choose a category – Anchor your career around one big belief.
- Reinforce relentlessly – Every product, post, and partnership points back to that belief.
That’s how you move from author to authority.
Ryan's Launch as a Masterclass
Now, let’s talk about his latest launch over the past month, because it’s a blueprint for every aspiring Modern Author.
Ryan could’ve just tweeted “new book out.” Instead, he orchestrated a masterclass in community‑driven category leadership.
Here’s what he did right:
1. He built community before campaign
Ryan doesn’t have fans. He has a movement.
The Daily Stoic newsletter has over a million subscribers. His YouTube, podcast, and email list work together as a living ecosystem.
So when he launches, he’s not selling but he’s inviting his people to participate.
2. He made preorders an experience
Most authors beg for preorders. Ryan turned it into belonging.
He offered bonuses that reflected his philosophy, not gimmicks, but gifts:
Signed pages from the original manuscript.
Annotated bibliographies.
Private dinners at The Painted Porch bookstore.
You’re not just buying a book; you’re buying access to the practice of wisdom.
3. He created exclusivity through service
Scarcity isn’t about manipulation. t’s about meaning.
When Ryan says, “Once the doors close, they won’t open again until 2026,” it’s not hype. It’s a signal: the work matters enough to move on its own schedule.
He’s not performing urgency. He’s protecting integrity.
4. He centered it all around the category
Every touchpoint, from his copy to his videos, ties back to one idea: wisdom isn’t passive.
It takes effort. Reflection. Apprenticeship.
He’s not selling a product. He’s deepening a philosophy.
And after watching his last week, I sent about a dozen links to my marketing team for my new book to ensure our strategy maps to it (and so should you!)
Why This Matters for Every Aspiring Thought Leader
There’s a temptation in the creator world to think that if you just post more or go viral once, you’ll “make it.”
But the people who last, the ones who write, teach, and speak for decades, operate differently.
It sounds cheesy, but I'm not sure there's a better analogy.... they build amphitheaters, not campaigns.
Ryan Holiday is a case study in amphitheater‑building (you see the ancient Greek throwback there?)
Each book is a brick. Each video is a window. Each launch is another stone placed in service of something larger than himself.
That’s why his brand compounds. Because the work compounds.
And that’s what every Modern Author should aim for.
If you want to build a category that outlives the algorithm:
- Choose an idea that matters enough to work on for a decade.
- Build a system to explore that idea in different formats.
- Treat every project as part of your apprenticeship — not your arrival.
Making It Tactical: How to Apply the “Holiday Model”
If you’re serious about thought leadership, the kind that lasts, here’s how to put this into motion.
1. Pick a Problem Worth Apprenticing Under
Ryan apprenticed under Robert Greene. You can apprentice under your own idea. I'd say it this way... find something you'd be willing to work with a famous professor on for four semesters on.
Cone to their classes, do some research, help with their papers, and ultimately give some guest lectures.
Do it because you're so darn curious, you're game to invest in it.
Find something so rich, so complex, that it will take years to master, and that’s exactly why you should start now.
2. Define Your Category Early
Don’t write a general book. Write a book that names a space.
“Stoicism” became Ryan’s playground. What’s yours?
Think of it as planting your flag in a field you plan to farm for years.
3. Build a Flywheel, Not a Funnel
Ryan’s Daily Stoic isn’t a lead magnet. It's a habit machine.
Your goal isn’t conversion. It’s continuity.
How can you help your readers live your idea every day?
4. Make Your Launch a Reflection of Your Belief
If your book is about generosity, launch generously.
If your book is about clarity, make the process transparent.
If your book is about mastery, show the work.
Let your marketing embody your message.
5. Keep Apprenticing Forward
Even now, Ryan mentors others. He pays forward what Robert gave him.
Every Modern Author should do the same: not because it’s noble, but because teaching is how you cement mastery.
True Thought Leadership Isn’t Viral. It’s Shared Wisdom.
When people look back a decade from now and ask, “How did Stoicism become mainstream?” they’ll see Ryan Holiday’s fingerprints everywhere.
Not because he shouted the loudest.
Because he worked the longest.
He didn’t chase algorithms. He chased apprenticeship.
He didn’t optimize for speed. He optimized for staying power.
He didn’t just write about wisdom. He built wisdom into a business.
That’s what modern thought leadership really looks like.
And it’s the reminder every creator, coach, and author needs right now:
Because in a world obsessed with quick hits and clever hooks, the real differentiator isn’t timing.
It’s time.
And Ryan Holiday has proven what happens when you give an idea enough of it.
Keep creating Wisdom my friends (and let me know how I can help you create yours!)
Eric
Originally published in The Modern Author newsletter.
