The Daily Stoic email surpassed 500,000 subscribers.

I joined the team at 50,000 subscribers.

Here's 11 things I've learned about building a big audience and creating quality content:
1/ Simplify

Emerson said great writing uses “the language of the people.”

Bad writing uses big words.

People don’t want big words. If they want complex ideas, they want them made simple.

@RyanHoliday writes in a favorite @dailystoic email: if it’s not simple, it’s bullshit: Image
2/ Lengthen your timeline

Steve Martin once said that anyone who stays with an instrument for 40+ years will inevitably be able to play it.

500K subscribers was an inevitability for Daily Stoic.

Because @RyanHoliday plans to stay with it "until I drop dead."
3/ Good content wins

We use @ConvertKit to send the Daily Stoic email.

It shows new subscribers, unsubscribers, opens, etc.

@RyanHoliday doesn't know the login for Convertkit.

He doesn't care about numbers. If the content is good, numbers follow. He focuses on the content
4/ Solve problems

No one wakes up thinking, I need some philosophy.

"But they do wake up with problems they need solutions to," Ryan Holiday says. "As it happens, Stoicism provides a lot of those solutions."

To secure readers, solve their problems. Make something they need.
5/ Keep it concise

Daily Stoic emails are short (~500 words).

"Because I realize most people are very busy," Ryan Holiday says.

I like @morganhousel's rule: Make your point & get out of the way.

Better to leave people wanting more than feeling like you wasted their time.
6/ Meet people where they are

Daily Stoic has a podcast, a YouTube channel, Instagram, Twitter, & TikTok.

In a perfect world, Ryan Holiday would just write books, articles, & emails.

"But you gotta meet people where they are," he says. Then you can take them where you want.
7/ Show don't tell

From @RobertGreene, Ryan Holiday learned the power of illustrating ideas.

Ryan doesn't explain Stoicism to you. He shows you Stoicism.

People don't like lectures. People like stories.

The mantra that informs Ryan's approach to writing: show don't tell.
8/ Become a habit

Daily Stoic emails go out at the same time every day.

When you show up at the same time, you become part of a person's routine.

Weekly works too:

@JamesClear's "3-2-1 Thursday"
@tferriss' "5-Bullet Friday"

As @jspector writes, Image
9/ Hire experts

In mid-2021, we hired @mattragland to be our "Convertkit ninja"

Matt optimized our systems & processes and allows everyone to focus on what they do best.

"Pay for professional help," Ryan Holiday says, "if you think pros are expensive, try hiring an amateur."
10/ Consistency compounds

We have a Google Doc called "UNSENT"—it's 152 pages.

When asked how he produces so much, Ryan Holiday says he just writes a little bit every day.

“Compound interest is one of the most powerful forces on earth. And you can apply that to your own work.
11/ Just start

If you’re thinking about starting a newsletter…

Before I started mine, I told Ryan Holiday I was waiting to know for certain what to write about.

"Just start," he said

“You're better off starting imperfectly than being paralyzed by the delusion of perfection.”
TL;DR

11 lessons from @dailystoic surpassing 500,000 email subscribers: Image
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More from @bpoppenheimer

Sep 7
50% of books sell fewer than 12 copies.

90% of books sell fewer than 2,000 copies.

I’ve worked with authors who have sold MILLIONS of books.

Here are 13 things 90% of authors don't do…
1/ Test the ideas

As @RyanHoliday says…

Before it's a book, it should be an article.

Before an article…a conversation.

Think about how long it takes to read a book.

If an idea can't hold someone's attention for a couple minutes, don't write about that idea.
2/ Draw from timeless material

The Lindy Effect observes: the life expectancy of an idea/product/business increases over time.

@RobertGreene & @RyanHoliday want their books to hold up for decades.

So they root their books in ideas/stories/quotes that have held up for decades.
Read 17 tweets
Sep 1
Everyone thinks of John Mayer as a musician.

But his genius extends so far beyond music.

Here are 11 lessons from John Mayer on writing, creativity, and building an audience:
1/Turn off the reader

“Writer's block,” John Mayer defined, “is when the reader in you isn’t loving the writer.”

”It’s not a failure to write, but a failure to catch the feedback loop of enjoying what you’re seeing.”

When he writes, John said, “I turn off the reading brain.”
2/Take the trip inside

A young writer said her songs weren’t speaking to people.

“I think it’s because,” Mayer told her, “you haven’t made the trip inside. You haven’t truly made the trip inside."

What connects with people, he said, is when you’re connecting with yourself.
Read 15 tweets
Aug 27
The #1 lesson from working with bestselling authors (and it applies to whatever you do):

“Creativity” is a phony, made-up word for “lots of tedious work.”

Let me prove it to you with a story…
Tinker Hatfield revolutionized the shoe industry.

In 1985, Nike's shoe department was struggling. So it held a 24-hour shoe design competition.

Designers across all departments had to take part.

Including Tinker, then a corporate architect...
Tinker won the competition and was transferred to Nike's shoe-design department.

As he learned about Nike's innovative footwear technology, Tinker was amazed.

Nike was doing a terrible job educating the public about its innovative footwear technology.

Tinker had an idea...
Read 11 tweets
Aug 24
Ryan Holiday announced that his 14th book is available for preorder.

I’ve been his research assistant for the past 4 years.

Here’s 10 things I’ve learned from Ryan about writing, reading, self-discipline, and life:
1/ Production is a function of process

If you develop a process and commit to that process, Ryan likes to say, books come out the other side.

Books aren’t feats of genius, works of magic, or flashes of inspiration. They’re products of process.
2/ You’re the sum of your influences

I once asked Ryan about his unique writing style.

He credited his favorite writers.

“The key is that no one has the same combination of influences,” he said. “It feels like me because I’m the only person to combine my interests in my way.”
Read 15 tweets
May 21
Paul Graham, founder of Y Combinator, has a theory of genius.

In the recipe for greatness, 1 ingredient always gets overlooked.

THREAD: The Bus Ticket Theory of Genius
When we talk about what it takes to do great work, we usually focus on the importance of having 2 things:

•natural ability
•determination

When you study those who have done great work, a third ingredient consistently shows up:

An obsessive interest
To explain this point, Graham uses the example of bus ticket collectors. Bus ticket collectors have striking features:

• they care about bus tickets
• they don’t care if anyone cares that they care

That turns out to be a pretty powerful combination.
Read 18 tweets
May 10
Every day, @dailystoic sends an email with a life lesson rooted in the teachings of Stoicism.

I've read every one for 4 years straight (700,000+ words of wisdom).

Here are 11 Stoic lessons that will change your life:
Focus only on what you can control

Stoicism's foundational practice: differentiating between what is up to you & what isn't.

Up to you: attitudes, wants, opinions, habits, etc
Not up to you: weather, economy, what others do/say/think, etc

Then, focus only on what is up to you
Grab the smooth handle

Epictetus: “every situation has two handles.”

E.g. someone is rude to you: you can take it personally and get pissed off OR you can tell yourself they're having a bad day, it has nothing to do with you, & shrug it off.

Always grab the smoother handle.
Read 15 tweets

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