In partnership with

This edition is brought to you by Doola

Good morning to all new and old readers! Here is your Saturday edition of Faster Than Normal, exploring the stories, ideas, and frameworks of the world’s most prolific people and companies—and how you can apply them to build businesses, wealth, and the most important asset of all: yourself. 

Today, we’re covering Ryan Holiday and his journey from a college dropout to a bestselling author and modern Stoicism advocate, turning adversity into a platform for success and self-growth.

If you enjoy this, feel free to forward along to a friend or colleague who might too. First time reading? Sign up here.

What you’ll learn:

• How Ryan Holiday made stoic wisdom accessible to the modern world

• Lessons on building a direct line to your audience, using your current position to build for the future, and using physical spaces to enhance digital reach

• Quotes on creating value, persistence, and self-evaluation

Cheers,

Alex

P.S. Send me feedback on how we can improve. We want to be worthy of your time. I respond to every email.

Ryan Holiday

As a teenager, Ryan Holiday was adrift. College didn't suit him. He dropped out at 19. Most 19-year-olds who drop out of college end up living in their parents' basement. Not Holiday.

He had an asset many young people lack: curiosity. And he knew how to read. Really read. He devoured books on marketing, philosophy, and history. This self-education would prove crucial.

His break came when he landed an apprenticeship with Robert Greene, author of "The 48 Laws of Power." Greene saw something in the young Holiday. Raw talent, perhaps. Or just sheer determination.

"Ryan was different," Greene said. "He had a hunger for knowledge you rarely see in someone so young."

This apprenticeship led to a job as marketing director for American Apparel. At 21. Most people that age are still figuring out how to do laundry. Holiday was running marketing for a major clothing brand.

But it wasn't all smooth sailing. American Apparel was controversial. Scandal-prone. Holiday found himself in the middle of PR firestorms. Repeatedly. It was stressful. Exhausting. But educational.

He learned how the media really works. The good, the bad, and the ugly. This knowledge became the basis for his first book, "Trust Me, I'm Lying." It was a hit. Suddenly, Holiday was an author.

But his real breakthrough came with his next book, "The Obstacle Is the Way." It introduced Stoic philosophy to a new generation. In a practical, accessible way.

"I wanted to show how these ancient ideas could solve modern problems," Holiday said.

The book struck a chord. It sold over a million copies. NFL coaches assigned it to their teams. CEOs recommended it to their employees. Holiday had found his niche.

More books followed. Each one a bestseller. "Ego Is the Enemy." "The Daily Stoic." "Stillness Is the Key." Holiday became the face of modern Stoicism.

Critics emerged. Some academics accused him of oversimplifying complex ideas. Of commercializing philosophy. Holiday shrugged it off.

"My goal is to make these ideas useful," he said. "If that means simplifying them, so be it."

Today, Holiday's books have sold over 5 million copies worldwide. He runs a successful online course platform. He owns a bookstore in Texas. He's a sought-after speaker and consultant.

Not bad for a college dropout.

But Holiday isn't resting on his laurels. He continues to write, to explore new ideas. His latest book, "Discipline Is Destiny," came out in 2022. It hit the bestseller lists. Again.

"Success is nice," Holiday said. "But it's not the point. The point is to keep learning, keep growing. That's what Stoicism teaches us."

From aimless teenager to philosophical entrepreneur. That's the Ryan Holiday story. It's not rags-to-riches in the traditional sense. But it's a story of transformation. Of finding purpose. Of turning obstacles into opportunities.

And isn't that what entrepreneurship is all about?

Lessons

Lesson 1: Build a direct line to your audience. Holiday ditched traditional marketing and focused on creating content. He took his ad budget and built a content team instead. "I stopped spending money on all of that," he says. This shift allowed him to connect directly with his readers. He now has over 200,000 email subscribers and millions of social media followers. It's not just about reach. It's about ownership. You control the relationship. No middleman. No algorithm changes. Just you and your audience.

Lesson 2: Use your current position to build for the future. When Holiday was planning to leave American Apparel, he didn't check out. He doubled down. He invited people to tour the factory. He took on extra projects. He built relationships. "I am still benefiting from that work today," he says. Your current job isn't just a paycheck. It's a platform. Use it to build skills, connections, and opportunities for your next move.

Lesson 3: Use physical spaces to enhance digital reach. Holiday opened a bookstore in rural Texas. On paper, it doesn't make sense. But it's more than a store. It's content. It's a story. It's a destination. "The Painted Porch as a business makes very little sense on its own," he admits. "Yet it's accomplished so much–not only has it gotten tons of publicity, but it's been a story I have been able to tell... in my content as well as make my content in." Sometimes, the most powerful digital moves happen offline.

Lesson 4: Simplify complex ideas for mass appeal. Holiday takes ancient philosophy and makes it accessible. Some academics criticize him for this. He doesn't care. "My goal is to make these ideas useful," he says. "If that means simplifying them, so be it." This approach has led to millions of book sales and a massive following. It's not about dumbing down. It's about translating. Find the core of an idea and express it in a way that resonates with people's daily lives.

Lesson 5: Embrace the power of note-taking. Holiday uses index cards to capture quotes and thoughts from his reading. Each card gets a topic or theme. This system allows him to easily retrieve and connect ideas later. "My note cards are my external brain," Holiday says.

Lesson 6: Write simply, but not simplistically. Holiday's writing style is straightforward. He avoids jargon and complex sentences. But don't mistake simplicity for lack of depth. His books distill complex philosophical ideas into actionable advice. "I try to write the way I talk," he explains. This approach makes his work accessible to a wide audience. It's a reminder that clarity trumps complexity.

Are you ready to level up your E-Commerce business?

doola is the ultimate Business-in-a-Box solution for E-Commerce entrepreneurs. We handle all the unsexy yet critical back-office tasks, from entity formation and bookkeeping to business analytics and tax filings, so you can focus on growing your dream business.

We’ve helped over 10,000 entrepreneurs from over 175 countries start, run, and scale their E-Commerce business from anywhere in the world.

Start or Scale your E-Commerce business today

Ryan Holiday Quotes

On creating value: "Make things that matter to people, that help people. Make a constructive contribution to humanity."

On persistence: "Great entrepreneurs are never out of the game for long. They slip many times, but they never fall."

On self-evaluation: "The ability to evaluate one's own ability is the most important skill of all. Without it, improvement is impossible."

On focus: "It's time to sit down and think about what's truly important to you and then take steps to forsake the rest."

On execution: "Instead of pretending that we are living some great story, we must remain focused on the execution- and on executing with excellence."

On innovation: "An entrepreneur is someone with faith in their ability to make something where there was nothing before."

On perspective: "Thinking about and being aware of our mortality creates real perspective and urgency. It doesn't need to be depressing. Because it's invigorating."

On resilience: "Choose not to be harmed—and you won't feel harmed. Don't feel harmed—and you haven't been."

On obstacles: "The obstacle in the path becomes the path. Never forget, within every obstacle is an opportunity to improve our condition."

On continuous improvement: "Each time, you'll learn something. Each time, you'll develop strength, wisdom, and perspective. Each time, a little more of the competition falls away. Until all that is left is you: the best version of you."

Further Readings

• This Is the Secret to Business and Artistic Success

• Ryan Holiday: Do modern-day stoics make the best leaders?

• Ryan Holiday: How Challenges Become Opportunities For Entrepreneurs

That’s all for today, folks. As always, please give me your feedback. Which section is your favourite? What do you want to see more or less of? Other suggestions? Please let me know.

Have a wonderful rest of week, all.

Recommendation Zone

⎯

Hire remote employees with confidence

Two years ago, I hired an offshore assistant for the first time. Since then, I’ve recommended many people do the same. It’s been one of the highest leverage things I’ve done, helping with everything marketing and customer support (for The Intelligence Age) and personal matters and email management.

Athyna is a service that quickly (<5 days!) finds remote employees across 150+ countries for you or your team. They cover roles from sales and marketing to creative and product, and have worked with companies like Facebook, Zoom, Uber, Microsoft, Salesforce, and Amazon.

I’ve personally used Athyna and recommended them to my Brother, Will, who runs a fashion label, and several close friends running their own businesses. To date, they’ve all had very positive experiences.

If you’re in the market for talent, visit their website to explore options and cover all your hiring needs.

Why Faster Than Normal? Our mission is to be a friend to the ambitious, a mentor to the becoming, and a partner to the bold. We achieve this by sharing the stories, ideas, and frameworks of the world's most prolific people and companies—and how you can apply them to build businesses, wealth, and the most important asset of all: yourself.

Faster Than Normal is a ‘state' of being’ rather than an outcome. Outlier performance requires continuous, compounded improvement. We’re your partner on this journey.

Send us your feedback and help us continuously improve our content and achieve our mission. We want to hear from you and respond to everyone.

Interested in reaching Founders, Operators, and Investors like you? To become a Faster Than Normal partner, apply here.