A daily dose of Stoicism: How author Ryan Holiday doubled his email list one newsletter at a time

What do Marcus Aurelius, George Washington, Theodore Roosevelt, and General James Mattis have in common?

Their leadership style comes back to a 2,000-year-old philosophy: Stoicism.

Modern day definitions often pin stoicism as emotionless or boring, but the tenets of the philosophy come down to four values: courage, temperance, justice, and wisdom. Stoicism boils down to a singular idea: we don’t always control what happens to us, but we always control how we respond.

“We know that people don’t necessarily wake up and think, ‘Today is the day I’m going to start looking into an ancient school of philosophy,’” says Ryan Holiday, founder of The Daily Stoic. “But they do wake up with problems they need solutions to. It just happens that Stoicism provides a lot of those solutions.”

Holiday single-handedly brought back stoicism into popular culture with his 2014 book The Obstacle Is the Way—a modern day primer for how to thrive under pressure. You’ll find a copy on shelves of coaches, business leaders, and celebrities alike.

After the book’s runaway success, he began The Daily Stoic in 2016 as an online resource applying the lessons and wisdom of stoicism to modern life. Every morning, Holiday sends a short, 500-word newsletter on a particular topic, story, or idea that ties back to ancient philosophy.

Thanks to a chaotic 2020, stoicism is more popular than ever. “Often people look to Stoicism to get them through periods where there are large societal shifts that they can’t control,” says Holiday. “Of all the horrible things to be accused of, making philosophy popular and accessible doesn’t feel like a particularly bad one.”

Since launching The Daily Stoic newsletter, Holiday sent over 2,000 emails to 160 million people—the equivalent of five full-length books. In the last year, his email list grew over 50%, to a whopping 320,000 subscribers that wake up every morning with a dose of stoicism in their inboxes.

Even with all of that growth, his open and click rates remain steady over the past six years: 40% opens and 3% clicks.

We sat down with Holiday to find out more about the nuts and bolts of how he made his newsletter the foundation of his marketing strategy—and what drove such impressive growth.

Making email the foundation of The Daily Stoic marketing strategy

Holiday is a writer first, marketer second.

No stranger to the marketing and advertising world, Holiday had built a career pulling off (sometimes shameless) publicity stunts for companies like retail giant American Apparel and controversial author Tucker Max. He knew too well that once you give up ownership of your writing, it becomes something else.

“Most writers are dependent on an agent or an editor at a magazine or at a book publisher. When I started Daily Stoic, I wanted to write directly to my audience,” he says.

That’s sort of the dream as a writer anyway. You go direct. No gatekeepers.

—Ryan Holiday

What matters for your own email list is not the email marketing itself, but the why behind it. Before launching Daily Stoic, Holiday started a “ Reading List Email” where he still sends book recommendations once a month. “I announced the Daily Stoic email list to that list,” he explains, “which got us our first 10,000 subscribers or so. Since then, it’s largely been word of mouth.”

I wanted to build a relationship directly with my audience and reach a point where I’m not at the mercy of other people’s permission.

—Ryan Holiday

Takeaway #1: Understand the “why” behind your newsletter

Ryan sees far too many writers launching newsletters without a clear purpose. “I subscribe to very few newsletters,” Holiday explains, “and almost none of them are ‘news’ about the person. It has to be real content. Real stuff. Real value.”

“A lot of people want to have a big email list, but they have no real reason why anyone would sign up,” he says. “You have to come up with a good reason for the newsletter to exist. An audience isn’t a target that you happen to bump into.”

That’s exactly why he turned to Kit. “Even more than social, email is the way,” says Holiday. “Kit is more central to me than any publication.”

Building his email list may take plenty of effort, but for Holiday, the payoff is worth it—it means he can pursue his own projects, on his own terms. “I recently announced my newest book, The Boy Who Would Be King, which is the first book I’ve published myself,” he says.

We announced [the book] for pre-order to the Daily Stoic list and nearly 10,000 readers clicked through on the first day. The best part is that whether it sells a thousand copies or a million copies, I’ve already taken out most of the rewards: I got to make the book I wanted to make.

—Ryan Holiday

Takeaway #2: Encourage new subscribers with a variety of incentives

The Daily Stoic offers a variety of incentives to encourage new sign-ups. The welcome page offers seven different downloadable resources, from an introduction to stoicism to journal prompts and more.

If you’re going to create a newsletter, make sure you’re delivering something subscribers need or want, beyond the marketing value to you personally.

For Ryan, the Daily Stoic newsletter is the product

Holiday hit on the daily email cadence as a way to deliver value to his subscribers—not to sell to them. Part of what makes the content so relevant is that Holiday 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 Holiday. “I’m a nerd about philosophy, but I try to meet people where they are.”

I’ve been doing newsletters for 10+ years but I didn’t think I could pull off a daily newsletter.

—Ryan Holiday

Holiday’s daily emails follow a specific format designed to maximize subscriber value, not his own sales. While Holiday will announce new initiatives, books, or sales through the newsletter, it’s not the main purpose. Most days, the email focuses on a specific aspect of Stoicism, usually tied to current events.

Take this recent example:

It’s a simple design—a header and a CTA button. A few internal links. But the rest? Well-written, relevant content to an audience hungry for wisdom—hand-delivered by Holiday every single day.

That’s exactly what he promises on signup, and so that’s what he delivers. That dedication to consistency has led to a veritable who’s who of subscribers. “It’s just mind blowing to me. I’ll get emails from billionaires, Fortune 500 CEOs, professional and college athletes and coaches, bestselling authors, publishers and entrepreneurs,” Ryan says. “I’ll hear snippets from the emails get quoted by politicians in speeches, and athletes and coaches in interviews. It’s weird but it makes me take each email very seriously.”

Takeaway #3: Don’t assume all subscribers are starting at the same point

Holiday always wants to make sure people get the best first impression—so giving new subscribers the best possible welcome is crucial for Daily Stoic’s success.

“When people come into Daily Stoic they have different interests, different levels of understanding. You want people to be put on a track that lets them go at their own speed,” he says. “Let’s say someone signs up on my piece on how to be a great leader, or the art of journaling, we want the first emails they get to match that interest. Otherwise, potential lifelong readers bounce out because you’re not showing them what they want or need.”

Kit’s visual automations system makes it so easy to customize email sequences and see exactly how a subscriber is going to flow through those sequences.

—Ryan Holiday

Based on the location of signup, subscribers receive a different welcome flow—subscribers who come directly to the website, for example, are treated differently than referrals from social media. “We have a handful of different onboarding tracks based on where and why you signed up,” he says. “Most people who sign up generally for the daily email don’t know that they aren’t just getting random emails—they’re getting a handful of our absolute best emails first. So that segmentation that Kit does for us is really helpful.”

Takeaway #4: Deliver content your audience wants to read

Since The Daily Stoic is an email designed to be part of a morning routine, Holiday makes sure each email offers an aha moment subscribers can take with them throughout their day.

Holiday divides his email into three parts. “The first sentence has to grab the reader by the throat and pull them in. From there, my intention with every email—from the structure to the words I use and the stories I draw on—is to be very, very practical,” he says. “Finally, I always try to leave the reader with something they can actually apply to their life. That’s how every email ends: with a thought or a question or an idea that can be acted on and applied in the pursuit of living a better life.”

Writing an email newsletter should include:

• A distinctive voice (yours!) that directly addresses your subscribers
• A clear, actionable call-to-action at the end of the email
• Relevant, personal content that aligns with your original signup offer
• Focuses on benefits to the reader, rather than sales or features

How does Holiday know he’s delivering what subscribers want? People keep opening—and reading—his emails.

“We just try to put out great content that helps people live better,” he says.

Takeaway #5: Create a consistent email cadence

Doing that many emails—at 500 words a pop—takes hard work and discipline. But it’s not the scramble you’re imagining. “People sometimes ask how I write the email every morning, which of course, I don’t,” he says. “I write for a couple of hours every day, and I write in batches,” he says. “I have a Google Doc we call ‘UNSENT’, which is 152 pages long. We’re probably 3-4 months ahead at any time, and then every few weeks we schedule it out.”

Creating a consistent cadence means stockpiling content ahead of time and batching it so you’re not constantly wondering what the topic of the newsletter will be. Then, using Kit’s scheduling tool, creators can set up the emails at all once, for several weeks at a time.

Before you launch, write several drafts to keep ahead of the demand. But Holiday stresses that a daily newsletter isn’t for everyone. When you’re creating your own newsletter, deliver it at a pace you know you can achieve, whether that’s daily, weekly, monthly, or quarterly.

Expanding the Daily Stoic universe

While the Daily Stoic newsletter serves as the linchpin of Holiday’s marketing strategy, it’s not the only channel he uses to reach his audience. Email is the foundation of his marketing strategy, and Kit’s visual automations give him the flexibility to scale his email marketing program up and down without repetitive or manual tasks.

“When you have a strong email list, you can start strong in other mediums,” he says. “In 2018, we started producing an audio version of our daily email and that podcast seems to be the fastest growing new medium: 3 million downloads a month. But we launched it through the email list.”

In addition to the podcast, the website publishes editorial-length profiles, stories, advice, and interviews, while the Daily Stoic YouTube channel boasts nearly a quarter million subscribers. Often, he’ll add email courses, downloadable assets, and other offers based on other marketing campaigns. He also promotes these ideas via social media, with over a million followers on Instagram and 223,000 on X/Twitter.

Holiday dedicates much of the website to explaining the different aspects of Stoicism and adapting some of the lessons from his daily emails into blog posts and other pieces of content. “I think our “ What is Stoicism?” piece and our “ Who Is Marcus Aurelius?” piece drive a hunk chunk of new subscribers,” he says. “But I’ve also written a lot of other stuff that helps people solve problems. Dealing With Stress: 12 Proven Strategies For Stress Relief From Stoicism and How To Overcome Procrastination Based On Ancient Philosophy, for example.”

Every other channel connects back to the newsletter, which serves as the centerpiece for any new marketing efforts as the Daily Stoic expands.

To capture email interest, he “has a link to subscribe to the daily email in the bios and often add it in captions and tweets.” Once someone lands on the website from one of his other marketing channels, Holiday uses Kit’s landing pages to encourage people to subscribe:

Takeaway #6: Deliver both free and premium content to the same audience

The Daily Stoic email is actually two different emails every day, with a paid and a free tier.

Says Holiday, “We use Kit’s [tagging and segmenting] features to send an email to two different groups: Daily Stoic and Daily Stoic Life. Daily Stoic Life is our paid version, with extra emails, (ad-free), access to a private learning community, quarterly Q&As, and discounts in The Daily Stoic store and on Daily Stoic challenges and courses.”

With Kit, you can set up your paid newsletter for free with Kit Commerce. This tool lets creators sell paid newsletter subscriptions right alongside their digital products.

Once you’ve set up a paid tier, you can use the data you’ve already collected from your subscribers—in Holiday’s case, whether or not they’ve purchased merchandise, books, or engaged with articles on his site—to change the content subscribers receive.

Holiday uses Kit’s segmentation by tagging subscribers based on their behavior and the data you’ve collected and then grouping those tags together into segments. This video explains exactly how to use them:

This makes sure that every subscriber receives an email that’s relevant and personal to them.

Takeaway #7: Add additional value with custom email sequences

Automating emails takes a lot of work off of Holiday’s shoulders, especially when it comes to managing them alongside the daily newsletter.

To create a new Automation:

1. Go to the Automations page in your Kit account. If you’re not already a Kit creator, create your account here.
2. Click, “Create a new Automation.”
3. From here, you can choose a Form, a Tag, a Custom Field, or when a product is purchased to make this Automation start for a subscriber. This entry step is what will trigger the Automation.
4. Add additional logic or entry points as needed using the “+” sign. You can add up to 5 entry points to a given Automation.

This video shows you exactly what it looks like in action:

How to use Kit to build a successful newsletter

A daily newsletter requires many moving parts, from a dedicated writing practice to a specific cadence. But of course, The Daily Stoic isn’t just an email anymore.

Holiday has turned a 2,000-year-old philosophy into an empire, with the daily email forming the center of a marketing strategy that includes content marketing, conversion-optimized landing pages, and social media. It’s these engines that help drive new subscribers and keep the flywheel running.

Powered by Kit, Holiday has been able to bring The Daily Stoic to millions of people—without having to create a complicated email marketing machine. “Just like the best marketing is having a good product, we think the best way to get subscribers and keep them is to write great content, stuff that makes people’s lives a little bit better.”

Kit makes it easy to focus on what matters: your content. Try your free Kit account and start growing your newsletter today.