On Becoming a Perennial Seller as an Artist: Interview with Ryan Holiday

What does it take to be a perennial seller, and can any artist do it? Here to answer those questions, and more, is my friend Ryan Holiday. Ryan is a genius marketer and best-selling author of several books including The Obstacle is the Way, Ego Is the Enemy and Perennial Seller.

On Becoming a Perennial Seller as an Artist: Interview with Ryan Holiday

We jump right in by talking about how to create something that lasts – the message at the heart of his Perennial Seller book. In fact, Ryan believes in this message so much that he insisted on reading Real Artists Don’t Starve before he would help me with the launch! He needed to be sure it was a book with a message he could stand behind. It was an interesting experience for me and we dig into what that process was like for both of us.

Because he felt so strongly about this, I wanted to know if he has ever worked on something he didn’t believe in. Ryan said yes. He either believed in the project initially and then dug in only to find it wasn’t a good fit, or he’s been distracted by the price tag of the project or the name of the person involved. And in the end all of those were regrettable experiences!

On this episode of The Portfolio Life, we also how much time we should spend on creating something versus marketing it, common pitfalls we can avoid as artists, and something he is failing at right now.

Listen to the podcast

To listen to the show, click the player below (If you’re reading this via email, please click here).

Show highlights

In this episode, Ryan and I explore:

  • What is one critical question to ask yourself during the creation process?
  • How is creating and marketing a book like a legal trial?
  • What does it take to create a perennial seller, and what are some examples?
  • What makes a creation endure?
  • If you are traditionally publishing your book, why is it a mistake to only sell to your email list?

If it’s done right the work brings people to you.

Ryan Holiday

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The process of creating a perennial best-seller

  1. The creative phase. This is the phase during which you take your idea to your first draft of the manuscript.
  2. Polishing and positioning phase. Editing, refining, picking your title, your cover, your release date. Basically ensuring you have accomplished what you set out to accomplish.
  3. Marketing. This is the launch phase. During this phase you bring in your marketers, your influencers, you get attention for your creation and you sell it.
  4. The platform you build around the work. During this phase you build loyalty and relationship with your reader. The person you are trying to reach with your next book. The body of work you’re making as a creator. You establish a fan base or brand around your initial idea.

It’s going to be hard for you to continue doing what you do if you die of starvation!

Ryan Holiday

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Lessons from The Obstacle is The Way

  • What makes this a book people recommend to others, and why does that matter?
  • Why does giving away copies make a difference?
  • Why it doesn’t matter how long ago any book was published.
  • How not to be transactional after you give someone your book.


What have you learned about creating a Perennial Seller, and how will you apply that to your next creation? Let us know in the comments.