How To Make Your Book A Perennial Seller with Ryan Holiday

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How do you make creative work that lasts? In today's show, Ryan Holiday explains how to write a Perennial Seller. We talk about positioning, changes in marketing and the book industry, how to make your body of work last, as well as balancing ego with serving the reader.

In the introduction, I talk about my visit to San Francisco. Click here to see the pics on Flickr.

Today's show is sponsored by Draft2Digital, where you can get free ebook formatting, free distribution to multiple stores, and a host of other benefits. Get your free Author Marketing Guide at www.draft2digital.com/penn 

Ryan Holiday is a best selling nonfiction author, media strategist, and book marketing expert who has worked with clients like Tim Ferriss, Tony Robbins, Google, and Penguin. His latest book is Perennial Seller: The Art of Making and Marketing Work that Lasts.

You can listen above or on your favorite podcast app or watch the video here, read the notes and links below. Here are the highlights and full transcript below.

Show Notes

• What is a perennial seller?

• The ingredients that make a book relevant long-term

• Balancing the ego with serving the reader

• The importance of positioning a book correctly

• Changes in the book industry around marketing

• Ryan's thoughts on the future for authors

You can find Ryan Holiday at RyanHoliday.net and on Twitter @RyanHoliday

Transcript of Interview with Ryan Holiday

Joanna: Hi, everyone. I'm Joanna Penn from thecreativepenn.com. And today, I'm back with Ryan Holiday. Hi, Ryan.

Ryan: Hi. Thanks for having me again.

Joanna: Oh, it's great to have you on the show. It was May 2014 when you last came on the show, so over three years.

Ryan: Oh, wow.

Joanna: I know.

Ryan: That's crazy.

Joanna: I know, it's really crazy.

Ryan: I mean, look, I think when you have, as you would understand, when you have your head in a book that you're writing, time both goes incredibly slow and incredibly quickly.

Joanna: Oh, yeah, absolutely. So, just in case people don't know you:

Ryan is a best selling nonfiction author, media strategist, and book marketing expert who has worked with clients like Tim Ferriss, Tony Robbins, Google, and Penguin. His latest book, which I have here for those on the video is, “Perennial Seller: The Art of Making and Marketing Work that Lasts,” and fantastic book. So let's get into it, so let's start with definitions.

What do you mean by “perennial seller”.

Ryan: Well, so it's an industry term, right? If you if you call up the fine prints on The New York Times bestseller list, you'll find that perennial sellers are not included in the bestseller list.

What they really mean by that are books that are more than a year old and that sell steadily without blowing the doors off. So, in publishing, the other word for it is a backlist title. A title that sells year in and year out, week in and week out.

It's not topping any charts but it remains perennially relevant and renewable in that way. And so, those are the books that I try to write. And I think ultimately, that's what most of us are trying to do as writers, that's sort of the goal, right? I want to be the book that people are still reading 10 years from now.

Joanna: Why do you think that the industry doesn't seem to value those books as much as ones that rocket and then disappear?

Ryan: Well, it's interesting. On the one hand, they value them very dearly in the sense that probably the majority of revenues in the publishing industry come from those titles.

The reason that a publisher can afford a building in Manhattan is not because it's new titles are selling like crazy, it's because books that they acquired 10 years ago or 15 years ago or 50 years ago are still selling.

Penguin Classics is an enormous revenue driver for a publisher like mine, Penguin Random House. Because those are books that they don't have to pay a royalty to an author to because Homer and Seneca, and Charles Dickens are all dead.

But also because those books continue to be relevant they get taught in schools, they get bought in airports, etc.

So, on the one hand, they're very valuable to the industry, and on the other hand, they're very rare. It's very hard to set out to do one of those things and it's very uncertain whether it will work.

A book like, “What to Expect When You're Expecting,” which has been in print for 30 years is the definition of a perennial seller. But it doesn't contain anything new in it, there's no groundbreaking advice, there's no celebrity on the cover. It's very ordinary in some ways and the fact that it's lasted is what's extraordinary about it.

I think if you're a publisher or you're an editor, it's hard to go, “Hey, this little book is gonna be the engine that could for years and years.” You want to focus on what's new and sexy, and what's going to get media attention, and what's going to sell right out of the gate.

And then if you think about it, the editor who acquired, “What to Expect When You're Expecting,” is almost certainly not at that publisher anymore. So, although the publisher, as a business, makes a lot of money from things that were created many, many years ago. The people who were there, often, aren't going to be there for many, many years. That makes sense.

Joanna: Really. And it's interesting because what you're saying there is a lot of the things aren't necessarily new, but you still need to continue to be relevant. So, how can an author evaluate a creative idea in terms of making up for any old seller. Like you said, you want to write books that are all perennial sellers.

What are some of the key ingredients that make something relevant long-term?

Ryan: I think what you're doing is you're looking for the timeliness in a timeless idea, right? So when Jeff Bezos says, “We want to focus on the things that don't change.” What he means is we want to be a cutting edge company that's driven by technology, that does great groundbreaking things.

But at the same time, humans who are going to be our customers, they're going to be the same. So they like things that are cheap, they like things that get delivered quickly, they like having a wide selection.

So, what are the timeless elements of your work? What are the timeless parts of the audience that you're reaching?

If you're writing a novel, that novel has to be really, really touching, or it has to be deeply emotional, or it has to be really entertaining. You have to actually think about where the audience is going to be with the book.

When I write my books, my books are nonfiction and I'm thinking, “Okay, they have to be very practical for the reader, they have to deliver a lot of value.” And then that value has to be value that's going to continue to be true over time.

So this book needs to be as true to a 17-year-old as it's going to be to them when they're 40, that's what's going to keep the book being recommended in work. So, you have to think about those things in advance.

I think, far too often, authors just make whatever it is that they're trying to make and then they hope that they magically checked off these boxes.

Joanna: It's a good point. But how do we deal with things like technology?

In “Perennial Seller”, you are talking about marketing, and marketing, of course, changes. And then for a novelist, I mean, even I read my books from 2011 and the cell phone technology was different.

How do we deal with that kind of technology? Because you're a tech guy and a lot of your audience are also a tech savvy.

How do we do that with the perennial seller?

Ryan: When I was writing the book, Snapchat was called Snapchat, and by the end of the book it was called Snap. And then by the time it went to print, Instagram had rolled out stories and largely replaced Snapchat as the main video social network.

One of the things I really thought about when I was writing this book is there's a lot of marketing in it is, how can I write about marketing in such a way that it's not going to feel dated very quickly?

I did a book on growth hacking a few years ago which is a sort of a futuristic sell of marketing. But what I would try to do in those books is go to the fundamentals, go to the mindset side of things.

If you're writing very, very tactically, you just have to know that you're probably going to have to update this book over time or it's going to get dated more quickly than a book that's about the sort of more timeless elements.

Joanna: And then another thing that's interesting is there are a lot of great books that fail to become perennial sellers or even fail to sell. And there are books that will probably stay in the public consciousness like, “Fifty Shades of Grey,” which probably is a perennial seller more than, say, a Pulitzer Prize winning novel.

How do you differentiate between a perennial seller in a commercial sense and something that people might consider quality literature in time?

Ryan: Well, that's what's so interesting is that I'm not sure I would define, “Fifty Shades of Grey” as a perennial seller.

It was unquestionably a bestseller, a runaway best seller. But there was a story, just a year or so ago, about thrift stores in London that were like, “Please don't bring any more copies of “Fifty Shades of Grey.”” because all these people had bought it and then they regretted reading it, and then they wanted to get rid of it. I would imagine that it's sales, although, because it was such a big success, it might be selling more than your average book.

I would imagine its sales rep went all the way up and then almost all the way down at this point. It was a phenomenon that had a few years, but there are many, many bestsellers who were even bigger than “Fifty Shades of Grey” in the early 1900s and the 1950s that are almost completely forgotten today.

Meanwhile, a book like “Moby Dick” comes out, it isn't exactly appreciated when it comes out, but it's now sold steadily for 150 years.

It's not that that writing a bestseller or writing a hit is somehow a bad thing to do and you shouldn't do it, what I really wanted to do is focus on a specific kind of book.

I think too many people are chasing trying to be a hit right now, when in some ways, it's actually easier and more attainable to make something that sells steadily over time.

Joanna: That's interesting. And I was just thinking about your concept of ego. I believe you have an Ego is the Enemy tattoo as well.

Ryan: I do, yeah.

Joanna: I've been thinking about this because partly, for me, people say, “What do you want your legacy to be? Do you want your books to live on after you die?” And I think that's partly actually an ego thing. It's to say, “I'm important enough that I want my work to live on.”

How do you balance that ego with serving the customer, the reader?

Ryan: It's not about leaving some sort of monument for history in my opinion, but it is about making something that continues to deliver value for people over time.

For instance in The Ego is the Emeny, if I die tomorrow, those books would continue to sell not because I would be in an obituary, not like Tom Petty.

Tom Petty's songs spike in popularity because his death is such a sort of a publicly mourn event. But because my books are selling for reasons that have nothing to do with me anymore, you know I mean?

It's like if you write a book that does a job for people and you get it out to a large enough audience, what then happens is that that audience continues to pass that book along, and they really don't even care that you're the one that wrote it. I do continue to market those books, no question, and I would encourage authors not to quit on their books.

But my point is, if you do it right, your book is an advertisement for itself, and each person that reads it generates more readers.

And so the legacy for me and when I'm thinking about a perennial seller, it's not about providing a legacy for my children. It's about creating something that lasts because it does a good job. And hopefully, I'll be around for as much of that as possible.

If you think about what backlist means in the publishing industry, a title is considered back list after one year. So, when we say something that's perennial, we really just mean that it's lasted for longer than that. And that if you can just push to be a little bit longer than the average book, you're going to do well.

Joanna: It's interesting because I think the Indie self publishing space is a lot more about back list, and making money off of the back list. But in the book, you talk about persistence, sacrifice, survival, and creative crisis, which all sort of big topics.

What mindset shifts and work practices are needed for an author to make it long-term?

Ryan: Well, your book is not going to stand the test of time if you don't put time into making it, right? So I think we like this idea of the author that locks themselves into a hotel room and then in two weeks they have a finished manuscript.

That can work, but I think it's more the exception than the rule. And so, it's really putting in the work is the first thing. If you're not doing the work, why would the work last?

And then asking yourself, why are you doing this? Again, if you're doing the book because you think it's going to make you famous, because you think it's going to make you rich, that's going to tend to actually decrease the quality of the work and it's going to make it harder for you to persist through than the negative parts.

I'm in the deep unpleasant part of a manuscript right now. And if I was doing this because I wanted everyone to say that I was awesome, I'm not sure that would get me through this period. But the fact that I think that this is really important, that it really means a lot to me and that I feel like I have something to say here, that's what gets me to sit in front of a computer for hours on end.

Joanna: Absolutely. So you talk about positioning in the book and genre.

What are some of the things that authors need to do to position the book?

Ryan: Well, first up, just knowing where your book fits in the market is very important. So, everyone goes, “Oh, I want to be like Malcolm Gladwell,” and it's like, “Well, have you worked at The New Yorker for 10 years?” You know, or, “Do you know everyone in New York media?” “Are you published by Little Brown?” These are things that matter.

You have to know where your work fits in the market, really honestly and objectively, I think that's part of it.

And also what genre is it in. I hear people go, “Oh, it's a little bit of this genre and a little bit of that genre, and a little bit of this genre.” And actually, that tends to make it very confusing for the reader. You think that by combining genres, you're getting three times the audience, let's say, but actually you're getting one third of the audience.

Every project has to be clear what it does for the reader, who that reader is, and why they should check it out. And these are things that are both creative decisions but also marketing decisions.

When I see a book that's got a crappy cover and then the author goes, “Oh, you shouldn't judge a book by its cover.” Well, it's like then what's the point of the cover?

I want the writer to take everything about the book as seriously as they take every word in the book.

Joanna: But it's interesting because you work with a lot of authors, and so do I, obviously. And it's very difficult being self-aware enough, especially when you've just written a book, to understand where it fits, especially with fiction.

I've gone back and repositioned books because I'm like, “Okay, maybe they fit there instead.”

Do you see that with authors and how do you help them through to actually figuring out where they fit?

Ryan: Well, first off, it's definitely an art, not a science. It's not as clear as we would like it to be. But I do tend to find that we're often in love with our own work to a degree that the audience isn't.

One of the reasons that editors are so important or collaborative partners are so important, or even a marketing person is so important is that they're seeing what you're doing for the first time from a much fresher perspective.

Harper Lee turns in “To Kill a Mockingbird” and her editor says, “This is not a fully formed novel.” Well, obviously, she thought it was or she wouldnt' have turned it in, right?

When Adele turns in her album “Twenty Five” at 25 years old, she thinks it's done and Rick Reuben says, “You know, it's not.” And in both cases, they spend almost two years reworking those masterpieces to be masterpieces.

You need that voice to go, “It's pretty good but it needs to be better in the following ways,” or, “You think that what's really interesting about this work is plot number A, but it's actually plot number B.” Or, “This theme that you weren't considering that's really intriguing to the average reader.”

And then you can merge those visions together. I think collaborative partners are essential on any project. If you're going in alone, the margin for error gets much, much higher.

Joanna: What's interesting is that you mentioned Harper Lee and Adele spending years on one project. And there's always these two positions, one, you keep working on the same thing to try and make that thing. And then, or you go with this sort of Isaac Asimov approach of write 500 books of which only two will be remembered, or Dickens, you know, incredibly prolific.

I'm on the more prolific side than the masterpiece side.

What do you think about that balance?

Ryan: I think Woody Allen's a great example of this too, right? Let's do a movie every year and five or ten will be classics, and some will be forgotten, but they're all good. He thinks they're all good, right?

I'm not a huge Woody Allen fan, but he wouldn't say that some are bad, it's just some are better than others.

I tend to be on the prolific side, too. I tend to work quickly, but that doesn't mean I'm rushing anything, right? So just because you work quickly doesn't…it's just that some authors work more quickly than others, but I don't think any of those authors should be rushed in what they're doing.

If you're proceeding with a book that you don't think it's as good as it can be, I think that's a mistake. If you can make great work more quickly than Harper, like, ideally, Harper Lee would have been more prolific, too. I think the world is worse off for her only having written one book.

I think quantity has a way to get to quality. But if you're not putting in the work, I don't think that work is going to last.

Joanna: I think you're right.

When you were last on the show three years ago, you have “The Growth Hacker Marketing,” you had, “Trust Me, I'm Lying,” which had varied reactions in the market.

How has your thinking changed on book marketing and also how has the industry changed?

Ryan: It's interesting. “Trust Me, I'm lying,” we're coming out the fifth anniversary edition next week or a week after. And it's been interesting for me to redo my first book and to remember that I thought it had to come out so quickly at the time. I thought if I didn't get it out, it wasn't going to sell.

And now, I wish I'd taken a little bit more time on it. So, that goes to our previous conversation, but I think what I've learned is that if a book doesn't make noise, it's very hard for it to get an audience.

It's okay to be controversial, it's okay to piss a few people off. If your book doesn't stand out, it in some ways, it almost makes it irrelevant how good it is.

Think about it. If you wrote a masterpiece but nobody knows that it exists, how is it? Is it really a masterpiece, and will it be seen as one?

I think marketing is essential on books. My rule of thumb is that you should stick with marketing on a book for as long as you put into writing it. So if you took a year to write it, your marketing campaign should be about a year.

But I think what often happens, and maybe you and I as marketers sort of understand this a little bit better is that someone will spend two years on a book and then two weeks marketing it, and then go, “People didn't like it, I'm going to start the next one, right?” And so they tell themselves they are being prolific but really they're afraid to really put their work out there and get behind it, and I think that's a mistake.

Joanna: Well, looking at your marketing, I've shared a lot of your articles. And this is the point, you actually write incredibly long content rich articles, and whereas, you were known before with “Trust Me, I'm Lying,” with the most stunt-based sort of things.

Has that been a big shift for you in terms of moving into content marketing, on personal branding around that deeper content?

Ryan: Not really. I think it depends on the project.

“Trust Me, I'm Lying,” is a controversial book, so I wanted controversial marketing. It would be weird to be too flashy about that, right?

“Perennial Seller” is a book about timeless work that sells itself. It would be weird if I was buying billboards in Times Square to advertise for it.

I think the marketing has to match the work. And if it doesn't, that's a problem in either direction. I do think getting attention is particularly important when you're launching your career as well.

One of the benefits of having a platform or building up a fan base is not that you need to do less marketing, but that your marketing shifts from speaking to the entire world to speaking to your tribe of people. That's definitely a change that I've tried to make.

Joanna: But have you found yourself? Because you're writing for some sort of bigger publications as well now.

Is that a deliberate targeting for your marketing, for you and the company, and your books?

Ryan: Yeah. I'm always trying. I tend to find that the best advertisement for your writing is more writing. I'm trying to write things that deliver value to people, and I am trying to think of different audiences.

If I'm going to write a piece about how a book gets made, that's going to be probably for aspiring writers.

If I'm writing a piece about dissecting an issue in the media, that's going to be for people who are interested in that. If I'm writing a book about an article about self-improvement, that's going to be somewhat of an advertisement for my philosophy and my self improvement books.

It is about thinking about who each piece is for. And I think trying to have a diverse number of subjects that you cover is very important. If I was only writing about writing in book marketing, that tribe gets very small very quickly. I want to have a big tent with lots of different tribes in it.

Joanna: Yeah. And it's interesting because I've been refocussing on content marketing. But a lot of people think that it's done, that social media rule, video rule, you know, other things have taken over. Do you think there's still a place for the long-form content marketing?

If someone is launching a nonfiction book now should they be going back to the SEO fundamentals of long-form?

Ryan: Well, I don't know about SEO, but I think it's interesting. You wrote a book. So you want people to read it. You could be amazing at video but there's going to be a huge percentage of people who are watching those videos who only watch videos and don't read books.

Meanwhile, if you create articles by definition, the people who read them are people who read, right? So, I tend to see people's investment in these various platforms and not stopping to ask, “Am I really building a relationship with an audience around my writing?” Which is the thing that I do.

I think, certainly, there are opportunities out there for other different types of marketing and I think you should take advantage of them. But, the idea that because Facebook rolled out video, that the main form of human communication for thousands of years is suddenly going to become irrelevant, it's just preposterous to me.

Joanna: Yeah. And I guess it's also a personal preference.

Have you calculated that you have more words out in articles that you do in books?

Ryan: I would imagine, yeah, I would imagine at this point I probably do.

And look, here's the thing that I was to authors, it's like, okay, you just wrote a 60,000-word nonfiction book. That is many, many articles that you can break up. You can reuse that same content.

You could take 2,000 words from the book, edit that down to 1,500 words, then add 500 new words in terms of better transitions, and an intro, and a conclusion. And all of a sudden you have an amazing 2,000 word article that, frankly, is gonna stand out against other articles better because you put sort of book level effort into it.

Whereas, everyone else is writing these crappy list of books. I've been really putting in that work is important. And yeah, I see them as both advertisements for my books and ways to continue to explore the ideas that are in my books.

Joanna: I agree with you on that. See, the problem with content marketing is people are taking blog posts and turning them into books instead of the other way around.

What are your thoughts on that, the blog to book approach?

Ryan: I think if you are blogging and building an audience, and then you're creating a higher quality versions of some of those same ideas into a book, I think that makes sense.

I think the problem is people have very low standards for what they write online. I've worked on a number of projects with some internet marketers and they're really effective copywriters, and they don't understand that there is an enormous difference between the quality of prose in copywriting and what there is in a book.

Copywriting is keep reading, keep reading, and eventually, I'll tell you why you're reading this. Or eventually, I'll sell you something in exchange for reading.

A book has to deliver the value itself. With copywriting, I tend to find there's no there, there. Because that's the whole point, you're trying to get me to keep scrolling and so I get to a box and then I click ‘Okay' and give you my credit card.

Well, with a book, you've already given me your credit card in a sense. And so every page has to deliver a return on that investment.

I tend to find people are going about it the wrong way. I think people want to write in a more secluded setting with a longer term view in mind, and then you want to adapt that writing for the more fluid environment of the internet. And rather than trying to write ephemoral stuff for the internet and try to make it last in a book.

Joanna: Absolutely.

I do quite a little featured stuff for my show. And I love the idea of the Bowie bonds and buying into an artist feature. And we're seeing a lot of that kind ICAs, the queen offerings that people are doing, the economy, the block chain economy for independent artists.

Given that we're looking at perennial selling and where artists are going, where do you think the world is going for artists in the next 10 years?

Ryan: Well, there's an interesting site that just launched called Royalty Exchange that lets you bid on the rights to royalties from songwriters and artists, and now, writers. So, I think it is interesting.

People have forgotten that when you do this right, if you create a book that like, “What to Expect When You're Expecting,” that would have been an incredible asset to have acquired in the early '80s. That's a book that just spins off royalties, it doesn't have a lot of marketing, it's almost all profit.

Intellectual property is incredibly valuable. If you could think about a world where Shakespeare retained the copyrights to his works. Over the last 500 years, he would have accumulated billions of dollars if you think about all the things that have been based on those plays.

I am hopeful that this perennial content, there will be more innovations in how writers are able to monetize their work. I think, obviously, self publishing is a viable medium now, and allows sort of mid-list authors and successful authors to monetize their work.

I've also seen with mine, even though I traditionally publish and I make royalties from them, my books do well. I'm able to monetize my work because I have that direct relationship with my audience.

We've created posters that are based on my books and coins, and different products that I can sell directly to those readers. And since I'm not trying to sell them through a store, the margins are pretty good.

I know who my targeted customer is, and it creates a universe around the product. I think anyone who builds a platform where they have direct access to their fans is going to be well suited for whatever the future of media happens to be.

Joanna: Fantastic. And writing is definitely not going away.

Ryan: No. People thought that television was going to destroy radio, and radio is still around. People thought that the internet was going to destroy newspapers and “The New York Times” is having one of its best years ever.

We tend to think that new technology eliminates old forms, but in fact, they continue to soldier on. And the longer that a form has been around, the longer it is likely to continue to stay is what the research tends to show.

Joanna: Absolutely. Where can people find you and your book online?

Ryan: Yes, yes. So ryanholiday.net, I'm @RyanHoliday on pretty much every platform. And then “Perennial Sellers” should be everywhere books are sold. I think you have the British edition, right?

Joanna: Oh, yes. Does yours not look like this?

Ryan: No, no, is that the paperback or the hardcover?

Joanna: It's the paperback.

Ryan: Okay, yes. So in the UK, it's a paperback, and in the U.S., it's a hard cover. But, yes, so it's everywhere.

Joanna: That's interesting you say that, because I was actually gonna ask you, why isn't it a hard back? So, that's because of the UK.

Ryan: Yeah. And they did sort of a fancy version of the paperback. I have a great UK publisher, and they know the market really well. And so they were like, “Here's what we think,” and I said, “Awesome, let's do it.” And it's done really well. I think it's in second or third printing already.

Joanna: I've seen it in laser bookshops, but I'm going to buy an American one because the books I actually think I want to keep as perennial books on my shelf. I am starting to write hard backs, so it's interesting how that's happening now.

Ryan: Yeah. Well, it's like we thought ebooks were gonna replace hard cover books, but you know, print books are having an amazing run the last couple years because people are buying. People are going or discovering books on “The Daily Stoic,” which is one of my books is the deal on book club today. And so, we're selling a ton of digital books but I would imagine in six months, we'll see a corresponding spike in print sales because people would have really liked it and go, “Oh, I want to have a copy to keep.”

Joanna: Yeah, and an audio as well. The benefits of nonfiction. Anyway, thanks so much for your time, Ryan.

Ryan: Thank you so much.

Joanna: That was great.

Ryan: All right. Awesome. Thank you.