Ryan Holiday is one of my career idols. I know I’m not twelve years old anymore so maybe I can’t use the world “idol” but honestly, he is the career version of how I felt about the Backstreet Boys in 1997. Ryan just “gets it” when it comes to the media, marketing, PR and selling your wares. He was the director of marketing for American Apparel in his early 20s and is the bestselling author of some of my favourite non-fiction books: Ego is the Enemy, The Obstacle Is The Way & his newest book Perennial Seller which have sold hundreds of thousands of copies each. It was an honour to interview him on the topic of his new book, we discussed how to make work that lasts and lives on.
EMMA: Did anything in particular motivate you to write this book? Was it observing an online world full of creators and consumers of here-today-gone-tomorrow tweets/blogs/podcasts?
RYAN: Part of it was just waiting up one day and realising that almost everything I liked was old. My favourite bands had released their first albums before I was born and are still going strong decades later. The movies I find myself watching and re-watching aren’t in the theatres; they are on television—the so-called classic films. My favourite places in Los Angeles are The Original Pantry Cafe, Langer’s Deli and the Los Angeles Athletic Club—the youngest of which opened in 1947 and the oldest…1880. I remember picking up The Great Gatsby in high school for the first time and being shocked that something intended to be so timely—about the Jazz Age—could still feel so timeless more than a half century later. How many times have I re-read it since? A half dozen? My three favourite novels, The Moviegoer, Ask the Dust and What Makes Sammy Run? have a combined age of 210.
But more directly towards my career—the open secret in the publishing industry is that the backlist is where all the money is. The so-called “perennial sellers” are such a force in the industry that the New York Times actively screens them from appearing on the bestseller list. So while the general public thinks it’s all about the new hits, the real power is in creating work that lasts. I’ve tried to write books that will last and I try to only work on projects that have a chance to sell year in and year out. Otherwise, what’s the point? You only get to do so much in your life, you might as well focus on stuff that’s going to matter.
EMMA: Being bold and unique with your vision is of course a good thing. But how does a creative wanting to make a perennial seller get around the publishing industry who are often so afraid to take chances? Like Hollywood they seem to play it so so safe and don’t back things without proof.
RYAN: In a weird way, focusing on perennial sellers is a way to play it safe and fly under the radar. There is lots of competition to be the next big diet book or celebrity memoir or critically acclaimed novel. I’ll tell you there weren’t a lot of people wrestling to write books about Stoic philosophy in 2014. My publisher thought it was just a good enough idea to give it a little bit of money and then mostly leave me alone. That book has soldgoing on 400,000 copies now, close to a 100,000 in the UK alone. Now there is competition in that space, but I think the writers will find that it’s bad to follow other people’s leads.
The point is: You want to do something new and interesting or unusual because that’s where there is open space to be yourself. But you also want to root it in something timeless and accessible. Otherwise you just end up turning people off.
EMMA: Why do you think something like Harry Potter ended up being a perennial seller?
RYAN: Well, the series just celebrated its 20th anniversary. Soon enough there will be kids reading it who weren’t even born when the novel was released. That’s the definition of perennial. Of course, one way to last is to be really big when you come out—and Harry Potter was, certainly. But I would argue that the real reason that series has lasted is because it’s rooted in the timelessness of coming of age, of the Hero’s Journey, of our childish love of fantasy and magic. J.K; Rowling built an entire universe too. She didn’t stop at one book. She didn’t coast or exploit her fans either. She made that series perennial.
EMMA: Do you think deep down we all want to be remembered for something we make?
RYAN: Nobody sits down to make something they hope will be immediately or quickly forgotten. Elon Musk compares starting a business to “eating glass and staring into the abyss of death,” and no one would willingly do all that if they thought their efforts were going to disappear with the wind. But of course, most work is forgotten. I think that’s a shame (and unnecessary.) The reason I set out to study these books that had lasted was partly selfish. I wanted my own work to benefit from what these great creators had learned.
EMMA: People often get embarrassed for wanting to make lots of money from our art. As we’re often made to believe that art is meant to be “pure” and we shouldn’t “sell-out” – you talk about this in the book. What are your views in terms of your own work?
RYAN: Selling out is such a bullshit notion. The only way you can be a sell out is if you think you’ve abandoned the principles behind your creative expressions. That hater says you’re a sell out because you made money? Who cares? Look, the whole point of marketing art is to reach an audience. Why anyone would artificially constrain that audience is beyond me. That being said, there are all sorts of things I won’t do as a writer. I don’t like scammy sales letters, I only want to write and make the books I like. But again, that’s my internal compass about what I feel good about. It is in no way influenced by what other people might think.
And the other part of this that I think people miss is: If you can create financial freedom, artistic freedom will follow. Jay Z’s music has gotten better the more successful he’s become as a businessman. Why? Because he doesn’t care if it sells or not or is on the radio or not. He cares if he is beating himself. He cares if it is improving his reputation as a musician.
EMMA: You reference a lot of cultural moments, books, films, celebrities in the book and it’s obvious you read a lot. Do you think we should carve out time to read during our work day?
RYAN: Writers are lucky in that reading is part of the job…if not the job itself. Overall I think it’s a travesty that someone could spend their day dicking around on email, accomplishing nothing and their boss would think they were productive, but if they leaned back in their chair and read a book that gave them 20 good ideas for the next year the boss would say, “I don’t pay you to sit around and read all day.” When I was at American Apparel I would leave early or take long lunches to read. Not because I was lazy but because it was how I was getting good at my job.
EMMA: I like how you criticised the 20%/80% split (the theory that 20% of your time should be spent making, 80% should be spent promoting it). After all you can’t promote something successfully if it’s rushed and shit. Do you have any tips for how to self-promote in a way that feels good?
RYAN: The key for me is to treat marketing like it’s part of the creative process. You make something—you have to be creative. You market something—you have to be as creative or more creative. Treat it like it is its own artistic medium. I think someone like Banksy does this well. It’s not just the work but how the work will be seen, shared, what the media narrative will be. It’s all on the same continuum for me. Even answering these questions in this interview, I don’t see it as an obligation. I see it as a chance to 1) talk to a cool audience 2) work out my own thinking about things I might not have considered 3) that it’s a privilege to be able to talk about my work (how many creators are killing just to get out of obscurity? So I don’t like the entitlement that too many creators have about marketing.)