Joshua Keel

How to Craft a Perennial Seller

October 9, 2019

I’ve been following Ryan Holiday for a while. I get his book recommendations newsletter, and I read a lot of the articles he posts to Medium, Thought Catalog, and his own blog. He’s a great writer, and we share a lot of values, judging by the titles of his books: Ego is the Enemy, The Obstacle is the Way and Stillness is the Key.

What a great statement of practical philosophy and personal priorities those three titles are. Ryan is someone I look up to and admire, but also consider a peer. We’re around the same age, and love reading and writing about the things that matter to us.

I don’t feel as if Ryan is somehow far above me, and I could never stand where he stands. I do, however, know that he has figured out some things I have not. I don’t have his writing success, or his marketing know-how, his seemingly enormous book collection, or his keen interest in Stoicism. Ryan is someone I can learn from and relate to.

That’s why I was so excited to read his book Perennial Seller: The Art of Making and Marketing Work that Lasts. In it, Ryan shares personal reflections on all that made him the superstar author he is today, as well as advice and insight based on his marketing experience with American Apparel, and the many authors and creative professionals he consults with through his company Brass Check.

I learned a ton from this book. Here are some of my takeaways, divided by chapter.

The Creative Process

Create damn fine work. That is where marketing starts. If you were a salesman, would you rather sell an amazing product you fully believe in, or a crappy one you struggle to find anything good to say about?

As artists and creatives, we’re also salespeople. We’re in charge of letting people know who we are and why our product (our art, music, writing, app) is worth buying. But what sells? Good shit sells. When I find something that amazes and inspires me, I want to share it with others. That’s how stuff sells. People are driven by their own love of your product to share it with their friends, to shout it from the rooftops of Twitter.

Without a great product, you don’t have anything to market. You focus first on building something amazing, then you’ll have something worthy of telling people about. It’s in the creative process itself that our marketing efforts begin. Our focus has to be on making great art. Then all the rest can follow.


Before you even start working on your project, figure out who it will be for. Why does someone need this thing you’re making? What is it going to do for them?

Ryan asks us to fill in the blanks as we think about our project. “This is a _____ that does _____. This helps people _____.” To fill these out, you’re forced to think through what exactly it is you’re trying to accomplish with your work.

This is where you have to develop some empathy. Are you doing your art primarily for yourself, or do you want to move someone to think or act differently, to feel inspired or understood? When people are interacting with your work, they’re having an experience. What kind of experience do you want it to be?

Will it be a boring experience that will make them yearn for their Netflix queue? Or will it be carefully crafted to change their lives and inspire them to be better human beings?

Positioning helps you make sure it’s the latter. You go in with a plan for what you want your work to mean to people, and you make sure at every step that you’re executing on that vision.


What Ryan says about marketing surprised me. He’s actually not that big on traditional press and media. The big thing I learned was that TV appearances, radio, and New York Times profiles equal credibility, but they don’t necessarily drive sales as much as you might think.

What does drive sales? Engagement with individual people. The people on your email list. The people who show up at your book signing. In other words, word of mouth. Engage your audience, build it person by person, and create true fans. Those fans will be more than happy to tell anyone they know about you and your work.

One of the most interesting things Ryan talks about is the principle of giving people a reason to be excited about you. If you do want traditional media coverage (and who wouldn’t?), follow reporters. Get to know the people in your space who report on work like yours. Listen to the podcasts where your niche is being talked about.

Then, reach out to people. Offer them something. You’re not asking for a favor from them. You’re telling them about something interesting that’s going on (your work!) and why they should care about it. Everyone in the media is looking for their next lead on a story. They want to cover something fascinating. Make their job easier by first being fascinating, and then letting them know how they can make a great story out of it.

Build relationships. Not one-sided exchanges where you’re pushing your work, but full-fledged, reciprocal relationships where you’re willing to do favors for the other person, and they you, because you like each other and want to see the other succeed.


Your platform is a direct way to talk to your audience. It’s what allows you to distribute your work. It’s what helps you be heard in a noisy world. Without a platform, your work is invisible.

You should own your platform. That way you can weather the ups and downs and changes in technology that will inevitably come. If you wake up tomorrow and Facebook and Twitter are gone, how are you going to communicate with your people?

Eliminate the middleman by building up an email list that only you control. This is the core of your platform. If you have an email list, you have a direct connection to your audience, and no one can say otherwise.

Your platform is made up of people. People who follow you on Twitter, or came to your show, or signed up for your newsletter. And those connections with your fans are your most valuable capital. Without them, you’re sunk.

So how do you build a platform, when you’re starting from zero? Person by person. Conversation by conversation. Be interested in others (because hell, they are interesting, if you take the time to notice). Develop friendships with other creators. Get to know your peers. Forge connections—because you never know when that connection could be your next opportunity for something amazing.

And when you’ve built an army of friends who have let you into their Inbox, you have the ability to make a living from your creative work. You have a platform.

If you want to make work that matters, and if you want to make a living doing it, go out and get yourself a copy of Perennial Seller. It’s right up there with Steven Pressfield’s The War of Art among the list of books I’d recommend to new artists and creative folk of all stripes. And that’s saying something, because The War of Art is one of my favorite books of any kind. Just buy the dang book, and thank me later.

Oh, and if you like what you read here, why not sign up for my weekly newsletter? I’ll send you my thoughts on being a wiser, kinder, more creative human.

P.S. Ryan Holiday didn’t pay me to write this. I’m just a huge fan. See aforementioned “word of mouth”.