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Episode 238: How to Create Something – The Art of Making and Marketing

Ryan Holiday, stop writing books that are just for me!

With “Perennial Seller” you just answered an obsessive question I’ve had for years: What makes something, someone, some product, some art, withstand the test of time?

What is the magic sauce? The secret formula?

What makes something sell a million copies a year (music, art, books, products, etc)… forever?

I want to know.

I’ll try my best to summarize our conversation and your book but people should buy the book for your 1000s of examples:


If you write what everyone else is already thinking, then nobody needs to read your work, or use your product.

They already have it.

It doesn’t matter if you are 50% better than anyone else.

Nobody understands how to judge that except the experts in your field. And those experts don’t care about you. They might even hate you.

Create your own field. And be 1000% the best in that field.


The 100th person who writes a “50 Shades of Grey” style book, or a disco pop EMD album can…MAYBE…get 1% of the audience.

If you find an underserved audience, you can get 100% of it.

There’s an important side effect of this: IF YOU ARE DOING SOMETHING FOR THE MONEY…YOU LOSE.

Because the rest of the world is competing for that dollar.

Money is a side effect of creativity, quality art, creating something unique, and building your marketing into that art.


Test out sample chapters. Release songs on YouTube. Keep iterating. Keep digging for your authentic voice.

In comedy, it took Louis CK 20 years of telling jokes before he found his voice when talking about dating and parenting.

Don’t look for LOTs of fans at first. Look for the hard-core fans. The ones who will stick with you while you go on this crazy ride. The ones who will share.

What my prior podcast guest, Kevin Kelly, calls “The One Thousand True Fans”.


Ryan told me that “Smokey and the Bandit” beat “Star Wars” at the box office the same weekend they both opened.

I did not know that! It almost seems like blasphemy to me.

John Grisham only sold a few thousand copies when he first published “A Time To Kill”. Only much later did it sell millions.

Catcher in the Rye had a slow start. Now sells a million copies a year.

The best works of art and the best products have to fight the masses to find their right audience. But when they do, the audience will reward them.

Write or create what is unique to you, find the 1000 true fans. The ones who are hard-core and love the value you bring. And serve that market over and over.

That divides the winners from the non-winners.


“Choose Yourself” could have been another ranty personal development business book (“Blah!”).

Instead I wove in a personal story of struggle and loss and pain. Pain that changed me and still does every single day to (hopefully) lesser extent.

This is what makes a story both unique (it’s my story) and universal (everyone experiences pain, everyone wants to solve it).

Too many people play a persona (“my life is perfect so let me teach it to you”) and that’s inauthentic.


Star Wars is a perfect example. It’s the ‘arc of the hero’. A boy who struggles, encounters problems, faces them, lives forever. I.e. Jesus. Krishna. Buddha.

Star Wars is a sci-fi western (great example of “idea sex”) where he innovated on the graphics but used a story that was basically “Focus grouped” for thousands of years. Thousands!

So he stuck within the rules of a genre (actually several that he combined) but also made it uniquely his own.

This is the key to successful art.

Telling a story that is personal to you AND resonates with everyone is very difficult. It takes practice. It takes marketing. It takes listening. That’s why these are the items that become perennial sellers.

It’s worth it to build that skill. How do you do it:

  • Understand the history of what you love
  • Learn from the best
  • Practice over and over
  • Build marketing into your art.
  • Experiment, learn, repeat
  • Follow the rest of the advice in this article.


Ask yourself, “Who is this actually for?” Who is your fan?”

“A lot of creators struggle with this,” Ryan said. “You make this great work and then you think the world is eagerly anticipating it, but they’re not.”

You have to have a sense of honesty internally to know who your stuff is for. So you need to ask the right questions from the beginning.

You have to connect strongly with those initial hard core fans.

Combine your creative idea with the heart of another human being.

The people who struggle with your struggle. The people who will be better off when they read your writing or use your invention.


If you do something new, people will not like you. SOMEONE will hate you.

“When the moon landing happened,” Ryan told me, “It had 93% market share. That’s incredible.

“But think about it. That means 7% of the audience turned on the TV, saw Neil Armstrong stepping on the moon and said, ‘oh, this is boring. I’m going to change the channel.”

Be ok with that.

Iron Maiden had a lot of people hating them. And yet they focused on their core audience and became one of the most popular rock bands ever despite playing music that would NEVER make it on the radio.

The TV show, “Seinfeld” was on the verge of cancellation it’s first few years.

But Jerry Seinfeld already had a hard-core following not only among fans but even among network executives.

Having network executives as hard-core fans guaranteed him the runway he needed to succeed with the wider audience.

The Beatles had a hard core following from 1957 on that, even when their label rejected them in 1962 (“Guitar bands are going out of style”), their hard core fans kept them afloat and a year later they were catapulted to success.

Your hard core fans buys you “marketing capital” that you “spend” on expanding to a wider base.

If you go for just the wider base, you face the competition too early and end up as an also-ran.

And remember, the moment you first start – NOBODY at all cares about you.


I don’t hit publish unless I’m actually feeling physical fear about doing it.

If you don’t want to divide the audience, don’t hit publish.


Nobody really cares about you. Every industry is turning upside down. Everyone is worried about their own jobs and agendas.

You can’t just be better than everyone else. There’s “infinite shelf space” as Ryan puts it.

You’re competing against “Breaking Bad”, Google, Trump’s tweets, old episodes of Seinfeld, Harry Potter, etc.

If you want to be out there and noticed. If you want your vision to succeed. If you want your product used…you need to talk about it. You need to represent it. You need to write about it. You need to be about it.

The marketing has to be part of your art. Even the Beatles made entire movies (art and marketing at the same time) to support their true creativity (the music).

Marketing is no longer about ad space. It’s another important outlet of your creativity.

And if it doesn’t work. Move on. You don’t have one idea in you. You have 1000s.


Most things fail. The ones who succeed, pick up from their failure, figure out what went wrong, figure out how to validate an idea better with an audience, and then go back and try again.

They try over and over until they find that hardcore audience that will listen.

Validation is a cure for stupidity.

They go back again and again until their skills are refined. John Lennon and Paul McCartney met in 1958. They played and played and played and refined.

In 1962 their label rejected them (“Guitar bands are on their way out”).

The rest is history.

Now you can create history.

And Ryan, one final note. Please keep writing all-star books so you can keep coming back on the podcast.

And keeping writing books that will make my life better.

And then letting me ask you any question I want about them. Because the’s the way I roll.

You’re a good guy and, of course, welcome any time but I’m really mostly interested in reading things that make my life better. So keep at it.

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