Perennial Seller: The Art of Making and Marketing Work that Lasts

Perennial Seller: The Art of Making and Marketing Work that Lasts

In my 2013 personal annual review, I wrote that I wanted to build something that would last 100 years. I have made no progress over the last four years. It is such a large and intimidating goal that it seems impossible to begin. Where to start? What are the steps along the path? Ryan Holiday's "Perennial Seller" promises to help us "make something that can stand the test of time," and he delivers.

The book surprised me with its focus on the marketing side of things. A quarter of the book is about actually creating a masterpiece. The remainder of the book deals with the positioning, marketing, and platform strategy needed to make a work grow and endure. This part of the process had always been a mystery to me. I was one of those naive people who thought writers just handed off their works to their publishing companies ("kissing it up to God") and then their work was done.

Holiday insists that great creators see "every part of the process as their responsibility" and he relentlessly pushes us build a platform to connect with our fans. I had never thought about having a pre-built platform/network of people to help jumpstart the spread of my work. It's such an obvious idea that I can't believe I hadn't been doing it before. And to give us a clear and achievable target, Holiday quotes Kevin Kelly who says:

Anyone producing works of art — needs to acquire only 1,000 True Fans to make a living

Beyond the importance of a platform strategy, I found Holiday's thoughts on the advertising interesting. While the initial launch is an important opportunity, he discounts the long-term importance of advertising:

If a product is going to sell forever, it must have strong word of mouth. It must drive its own adoption. Over the long haul, this is the only thing that lasts

But how to rate this book? It's certainly not great literature itself. Most of Holiday's recent work (including his "Obstacle is the Way" is written according to the same formula. Find a bunch of great quotes and then include a very thin veneer of analysis and add some link to modern situations.

Having followed Holiday for years, I feel like he recycles the same guys (Churchill, Epictetus, Lincoln, Robert Greene, Aurelius) over and over again. He seems brilliant and widely read when you first encounter him, but repeated exposure threatens to expose the shallowness beneath the surface. I'm particularly concerned by his increasing promotion of James Altucher (one of his clients at Brass Check) who follows a similar but less well-executed formula for writing his own mediocre books. See my 2-star review of Altucher's "The Choose Yourself Guide to Wealth" for why I think this is a bad direction for Holiday.

Yet this book accomplishes what few other books have - it made me change my behavior. Taking Holiday's advice that, "the best time to have built your network was yesterday. The second best time is right now," I have started to set up my own "platform" for connecting with people who enjoy my book reviews. One day, when I write my great American novel, I'll be well-prepared to begin the next step of the journey: turning it into a perennial seller.

My highlights below


The book that Connolly wrote, Enemies of Promise, explored contemporary literature and the timeless challenges of making great art.

No wonder people think creative success is impossible. With this short-term mindset, it more or less is.

They are examples of a phenomenon known in economics as the Lindy effect. Named after a famous restaurant where showbiz types used to meet to discuss trends in the industry, it observes that every day something lasts, the chances that it will continue to last increase.

The works of Homer and Shakespeare, along with hundreds of other dead playwrights and philosophers — despite all being available for free online — still sell hundreds of thousands of copies per year.

It will teach you:

  • How to make something that can stand the test of time
  • How to perfect, position, and package that idea into a compelling offering that stands the test of time
  • How to develop marketing channels that stand the test of time
  • How to capture an audience and build a platform that stands the test of time

Part I - THE CREATIVE PROCESS: From the Mindset to the Making to the Magic

The more books we read, the clearer it becomes that the true function of a writer is to produce a masterpiece and that no other task is of any consequence. —Cyril Connolly

Even the best admen will admit that, over the long term, all the marketing in the world won’t matter if the product hasn’t been made right. In fact, it’s a classic “measure once, cut twice” scenario, in that the better your product is, the better your marketing will be. The worse it is, the more time you will have to spend marketing and the less effective every minute of that marketing will be.

Phil Libin, the cofounder of Evernote, has a quote I like to share with clients: “People [who are] thinking about things other than making the best product never make the best product.”

“Lots of people,” as the poet and artist Austin Kleon puts it, “want to be the noun without doing the verb.”

To create something is a daring, beautiful act. The architect, the author, the artist — all are building something where nothing was before. To try to create something even better than anyone has ever done it before is even bolder.

I quoted that Orwell line too. “You should only be a writer,” I said, “if you can’t not be a writer"

“Literature is a wonderful profession,” the friend explained patiently, “because haste is no part of it. Whether a really good book is finished a year earlier or a year later makes no difference.

Yet for all these contemporary influences, Lucas’s most profound source material was the work of a then relatively obscure mythologist named Joseph Campbell and his concept of a “hero’s journey.” Despite the trendy special effects, the story of Luke Skywalker is rooted in the same epic principles of Gilgamesh, of Homer, even the story of Jesus Christ. Lucas has referred to Campbell as “my Yoda” for the way he helped him tell “an old myth in a new way.”

As Hemingway supposedly said, “There is nothing to writing. All you do is sit down at a typewriter and bleed.” This is a wonderful, seductive line as we consider sitting down at our own proverbial typewriters. The problem is that it is preposterous and untrue. It is directly contradicted by Hemingway’s own meticulously edited, often handwritten manuscript pages. The John F. Kennedy Presidential Library has some forty-seven alternative endings for Hemingway’s A Farewell to Arms. He rewrote the first part of the book, by his own count, more than fifty times. He wrote all of them, trying them like pieces of a puzzle until one finally fit.

Creative people naturally produce false positives. Ideas that they think are good but aren’t. Ideas that other people have already had. Mediocre ideas that contain buried within them the seeds of much better ideas. The key is to catch them early. And the only way to do that is by doing the work at least partly in front of an audience. A book should be an article before it’s a book, and a dinner conversation before it’s an article. See how things go before going all in.

You don’t have to be a genius to make genius — you just have to have small moments of brilliance and edit out the boring stuff.

In asking questions and soliciting input, you’re not letting other people determine what you work on. But by thinking this way you substantially reduce the fantastically inhuman pressure to be great simply by epiphany or a visit from the muses. Instead, it’s about finding the germ of a good idea and then making it a great product through feedback and hard work.

Successfully finding and “scratching” a niche requires asking and answering a question that very few creators seem to do: Who is this thing for? Instead, many creators want to be for everyone... and as a result end up being for no one. Picking a lane isn’t limiting. It’s the first act of empowerment we take as a creator. Recently Charlie Rose asked Lin-Manuel Miranda, creator of the blockbuster musical Hamilton, what set him apart from some of the smarter, more talented kids he had gone to school with. Miranda answered: “’Cause I picked a lane and I started running ahead of everybody else... I was like, ‘All right, THIS.’”

John Steinbeck once wrote in a letter to an actor turned writer, “Forget your generalized audience. In the first place, the nameless, faceless audience will scare you to death, and in the second place, unlike the theater, it doesn’t exist. In writing, your audience is one single reader. I have found that sometimes it helps to pick out one person — a real person you know, or an imagined person — and write to that one.

Just as we should ask “Who is this for?” we must also ask “What does this do?” A critical test of any product: Does it have a purpose? Does it add value to the world? How will it improve the lives of the people who buy it?

One of the best pieces of advice I’ve gotten as a creator was from a successful writer who told me that the key to success in nonfiction was that the work should be either “very entertaining” or “extremely practical.” Notice they didn’t say, “Should be very fulfilling to you personally” or “Should make you look super smart” or “Capitalize on some big trend.”

An essential part of making perennial, lasting work is making sure that you’re pursuing the best of your ideas and that they are ideas that only you can have (otherwise, you’re dealing with a commodity and not a classic).

As Goethe observed, the most original artworks “are not rated as such because they produce something new” but because they are saying something “as though it had never been said before.”

The higher and more exciting standard for every project should force you to ask questions like this: What sacred cows am I slaying? What dominant institution am I displacing? What groups am I disrupting? What people am I pissing off?

The point is that you cannot violate every single convention simultaneously, nor should you do it simply for its own sake. In fact, to be properly controversial — as opposed to incomprehensible — you must have obsessively studied your genre or industry to a degree that you know which boundaries to push and which to respect.

Our goal here is to make something that people rave about, that becomes part of their lives. The buried insights found in those other great works were not put there on the first pass. Work is unlikely to be layered if it is written in a single stream of consciousness. No. Deep, complex work is built through a relentless, repetitive process of revisitation.

These words of Steven Pressfield in his wonderful book The War of Art are a haunting and humbling reminder: “The counterfeit innovator is wildly self-confident. The real one is scared to death.”

Part II - POSITIONING: From Polishing to Perfecting to Packaging

The first wake-up call for every aspiring perennial seller must be that there is no publisher or angel investor or producer who can magically handle all the stuff you don’t want to handle. Sending in your proverbial manuscript is not the end of the hard work on a project — it’s not even the end of the beginning of the amount of work required. There will be no knock on the door, metaphorically or otherwise. Perennial sellers are made by indefatigable artists who, instead of handing off their manuscripts to nonexistent caretakers — “kissing it up to God,” to use a Hollywood expression — see every part of the process as their responsibility. They take control of their own fate. Not simply as artists but as makers and managers.

Seth Godin explains that “being really good is merely the first step. In order to earn word of mouth, you need to make [your product] safe, fun, and worthwhile to overcome the social hurdles to spread the word.”

When it comes to feedback, I think Neil Gaiman’s advice captures the right attitude: “Remember: When people tell you something’s wrong or doesn’t work for them, they are almost always right. When they tell you exactly what they think is wrong and how to fix it, they are almost always wrong.

Amazon has developed an internal culture that encourages physically writing out ideas, policies, suggestions, problems, and solutions — write to think is their belief. For that reason, Amazon actually requires managers who are launching a new product to write a press release about it before the idea is even given the green light. If they can’t come up with a way to express their idea in exciting and compelling terms at this early stage, well, thank God it was caught in time before they launched that dud.

Or, worse, a product pitch that bores you out of your mind because they haven’t put the time or thought into making it exciting.

There’s actually a famous line from an episode of Sex and the City, written long before Lady Gaga’s career was even conceived, that charts her exact trajectory: “First come the gays. Then the girls. Then... the industry.”

Regardless, you must start somewhere — ideally somewhere quantifiable. By which I mean: Who is buying the first one thousand copies of this thing? Who is coming in on the first day? Who is going to claim our first block of available dates? Who is buying our first production run? The number is going to differ for every kind of product and for each different niche. But there are rules of thumb. For books, the superagent and publishing entrepreneur Shawn Coyne (Robert McKee, Jon Krakauer, Michael Connelly) likes to use ten thousand readers as his benchmark.

Work that is going to sell and sell must appear as good as, or better than, the best stuff out there. Because that’s who you’re competing with: not the other stuff being released right now, but everything that came before you. A new TV show is competing with on-demand episodes of Breaking Bad and Seinfeld and The Wire. A new book is competing with Sophocles and John Grisham.

That saying “You can’t judge a book by its cover”? It’s total nonsense. Of course you can judge a book by its cover — that’s why books have covers.

At some point in every project I work on, I find myself recommending that the creator take the time to consult the book The 22 Immutable Laws of Marketing. The first seven laws of this classic marketing tome deal with the art of positioning and packaging. Not branding or style, but something deeper and also broader. Law 2, for instance, is about the art of categorization. “If you can’t be first in a category,” the law states, “set up a new category you can be first in.”

You’re going to need to explain to reporters, prospective buyers or investors, publishers, and your own fans:

  • Who this is for
  • Who this is not for
  • Why it is special
  • What it will do for them
  • Why anyone should care

You must deliberately forsake all other missions. If your goal is to make a masterpiece, a perennial seller for a specific audience, it follows that you can’t also hope that it is a trendy, of-the-moment side hustle.

Nabokov, a writer’s writer if there ever was one, said it best: “Literature is not only fun, it is also business.” To survive in business, you must make other people (and yourself) money. You must serve customers. To believe otherwise is bad business.

Most people are aware that Winston Churchill was both a politician and a statesman; fewer are aware of his brilliance as a writer or his passion for painting. He published his first book at twenty-three and his second at twenty-four, two works that made him an international celebrity at a young age. In his sixties, Churchill would begin a multivolume set titled A History of the English-Speaking Peoples, which took twenty years to finish and publish (he fought a world war in the middle of it). He would later win the Nobel Prize in literature.

Part III - MARKETING: From Courting to Coverage, Pushing to Promotion

As Peter Drucker put it: “[Each project] needs somebody who says, ‘I am going to make this succeed,’ and then goes to work on it.”

There is this great line from venture capitalist Ben Horowitz: “There is no silver bullet.... No, we’re going to have to use a lot of lead bullets.”

What did Steven do? He had the idea to pay to print approximately eighteen thousand copies of The Warrior Ethos in a special “Military Edition” that was not for sale. Then he gave those copies away through contacts he had in the armed services.

Someone I trusted said it was good. Now hopefully the same thing has happened to you. And so it goes... These are all organic, natural recommendations of products or ideas — and they are, without question, the single most powerful force in the life of a product. No one has the steam or the resources to actively market something for more than a short period of time, so if a product is going to sell forever, it must have strong word of mouth. It must drive its own adoption. Over the long haul, this is the only thing that lasts.

Anything that requires advertising to survive will — on a long enough timeline—cease to be economically feasible.

As Seth Godin has written, creating successful word of mouth begins with a single customer. “Sell one,” he says. “Find one person who trusts you and sell him a copy. Does he love it? Is he excited about it? Excited enough to tell ten friends because it helps them, not because it helps you? Tribes grow when people recruit other people. That’s how ideas spread as well. They don’t do it for you, of course. They do it for each other.”

Regardless of the tools used, though, what you’re saying is the same: Hey, as many of you know, I have been working on ______ for a long time. It’s a ______ that does ______ for ______. I could really use your help. If you’re in the media or have an audience or you have any ideas or connections or assets that might be valuable when I launch this thing, I would be eternally grateful. Just tell me who you are, what you’re willing to offer, what it might be good for, and how to be in touch.

The publisher and technologist Tim O’Reilly puts it well: “The problem for most artists isn’t piracy, it’s obscurity.”

Cory Doctorow, a well-known science fiction author and editor of one of the biggest blogs in the world, has explained, “Although it’s hard to turn fame into money in the arts, it’s impossible to turn obscurity into money in the arts.

The question, then, is: What is the right price to create a perennial seller? This is going to be controversial, but my answer is: as cheap as possible without damaging the perception of your product. (And by the way, with the exception of ultra-high-status premium brands, I think damaging the perception of your product through price is very hard to do.) The reason for this is that a classic of any kind has two characteristics: 1) It’s good, and 2) it has been consumed by a lot of people (relatively, at least). One of the best ways to build a readership, viewership, listenership, user base, or customer base early on is by making it cheap.

It is humbling, though, that the single most effective campaign I did for any of my books was discounting The Obstacle Is the Way. The publisher reduced the price of the ebook from $9.99 to $3.99 and ran a promotion in a newsletter that specializes in cheap ebooks. Sales more than tripled week over week and stayed steady — so steady that Amazon’s algorithm actually kept the discounted price for over a year, effectively subsidizing the cheaper price on my book as a loss leader for their customers. (It’s a promotion I’ve now run several times with other books to great success — including once on Labor Day, when we sold close to five thousand books in twenty-four hours.) Even after the discount ended, sales stayed elevated. Price is marketing.

As a general rule, however, the more accessible you can make your product, the easier it will be to market. You can always raise the price later, after you’ve built an audience.

Creators often forget that — that influencers are typically hyperfans (Carson was a comedian; he loved comedy), and their continued success depends on being seen as tastemakers and leaders.

What’s the best way to ask someone to endorse or share your work? Trick question. The best way is not to ask.

But the whole reason those lists matter so much is because they don’t take solicitations.

The way I describe this process is “trading up the chain.” In an interconnected media age, outlets pick up and re-report on each other’s stories. By starting with a small podcast where I could tell the story on my own terms, which led to a pickup on a small site that covers a niche, and then sharing and spreading that piece so it was seen by the right people, I was able to ultimately go from a tiny show to one of the biggest and most influential outlets in the world.

When my company works with musicians, we start by finding the most obscure and specific outlets you can think of. That’s how we get buzz going—we want to create the appearance that interest is bubbling up organically (which, because of our approach, it is).

At the most basic level, my only strategy for finding and getting media is straightforward. I google reporters’ names to find their email addresses and phone numbers (yes, they’re publicly available). Then I reach out and explain what I’m doing or what I’ve done. I let the work and the fact that it matches what they cover — that it’s interesting and compelling, and likely to do well for them — do most of the talking for me.

What all these stories have in common is that instead of hoping — or pitching, a more active form of hoping — that the media would cover these wonderful folks for their intrinsic merits and worth, they took matters into their own hands. They did things that created media opportunities for reporters. They did something that broke through the noise, that made a statement, and they did most of the legwork to boot. The sizzle sold the steak.

The most newsworthy thing to do is usually the one you’re most afraid of.

There is another way to attract earned media: a technique called “newsjacking,” popularized by the marketing thinker David Meerman Scott. He defines the concept as “the process by which you inject your ideas or angles into breaking news, in real time, in order to generate media coverage for yourself or your business.”

A rational, efficient advertising campaign involves two key things: knowing how much a customer is worth to you (or a customer’s LTV—lifetime value) and knowing how much it will cost to acquire that customer via the advertising you intend to use (or CPA—cost per acquisition).

Part IV - PLATFORM: From Fans to Friends and a Full-Fledged Career

I had acquired what, to my mind, is the most valuable success a writer can have — a faithful following, a reliable group of readers who looked forward to every new book and bought it, who trusted me, and whose trust I must not disappoint. —Stefan Zweig

Becoming a perennial seller requires more than just releasing a project into the world. It requires the development of a career.

There is a theory by Kevin Kelly, the founder of Wired magazine. He calls it 1,000 True Fans: “A creator, such as an artist, musician, photographer, craftsperson, performer, animator, designer, videomaker, or author — in other words, anyone producing works of art — needs to acquire only 1,000 True Fans to make a living.

The great Stoic Marcus Aurelius once admonished himself to be a “boxer, not a fencer.” A fencer, he said, has to bend down to pick up his weapon. A boxer’s weapon is a part of him — “all he has to do is clench his fist.”

The best way to create a list is to provide incredible amounts of value. Here are some strategies to help you do that:

  • Give something away for free as an incentive. (Maybe it’s a guide, an article, an excerpt from your book, a coupon for a discount, etc.)
  • Create a gate. (There used to be a Facebook tool that allowed musicians to give away a free song in exchange for a Facebook like or share—that’s a gate. BitTorrent does the same thing with its Bundles—some of the content is free, and if you want the rest of it, you’ve got to fork over an email address.)
  • Use pop-ups. (You’re browsing a site and liking what you see and BOOM a little window pops up and asks if you want to subscribe. I put such pop-ups at the back of all my books.)
  • Do things by hand. (I once saw an author pass around a clipboard and a sign-up sheet at the end of a talk. It was old-school, but it worked. Also, at the back of my books I tell people to email me if they want to sign up, and then I sign them up by hand.)
  • Run sweepstakes or contests. (Why do you think the lunch place by your office has a fishbowl for business cards? Those cards have phone numbers and email addresses. They give away a sandwich once a week and get hundreds of subscribers in return.)
  • Do a swap. (One person with a list recommends that their readers sign up for yours; you email your fans for theirs.)
  • Promise a service. (The last one is the simplest and most important. What does your list do for people? Promise something worth subscribing to and you’ll have great success.)

To get your first one hundred subscribers, Noah recommends doing this:

  • Put a link in your email signature. How many emails do you send a day?
  • See which social networks allow you to export your followers and send them a note asking them to join.
  • Post online once a week asking your friends/family/coworkers to join your mailing list.
  • Ask one group you are active in to join your newsletter.
  • Create a physical form you can give out at events.

As is true for so many things, the best time to have built your network was yesterday. The second best time is right now. The best time to get to know people and develop relationships is before you have some favor you want to ask them (this is called being a human being).

It’s hard to put it better than Alexandre Dumas does in an exchange in The Count of Monte Cristo. In it, the pretentious Danglars is showing off his expensive art collection, specifically his paintings from the “old masters.” “I do not like the modern school,” he says, expressing his disdain for the popular work of the day (which, as it happens, was early-nineteenth-century Parisian art). To which the sarcastic Monte Cristo replies, “You are quite right, Monsieur. On the whole, they have one great shortcoming, which is that they have not yet had the time to become old masters.”

Ian Fleming once wrote to his publisher, “I bet your other authors don’t work as hard for you as I do.”

The best marketing you can do for your book is to start writing the next one. It is frustrating because it is depressingly, frustratingly true. More great work is the best way to market yourself.

As Goethe’s maxim goes, “The greatest respect an author can have for his public is never to produce what is expected but what he himself considers right and useful for whatever stage of intellectual development has been reached by himself and others.”

Some people are not your fans and never will be. But there is still something to be done there: Colonel Parker, the infamous manager of Elvis Presley, came up with the idea to sell “I Hate Elvis” memorabilia so that Elvis could profit from his haters too. Everyone should know who their detractors are and rile them up every once in a while just for fun.

There’s another reality of creative businesses that we need to consider: Most of the real money isn’t in the royalties or the sales. For authors, the real money comes from speaking, teaching, or consulting. Silicon Valley entrepreneurs might do well by their business, but they might do even better investing in their friends’ companies.

To do our work without a platform is to be at the mercy of other people’s permission. Someone else must fund us, someone else must give us the green light, someone else must choose to let us make our work. To a creative person, that is death. Having an audience that we own? That we’re bound together with like hand and fist? That is life. Yet as I’ve said before: This does not just happen. It must be built. So don’t wait. Build your platform now.

CONCLUSION - What’s Luck Got to Do with It?

As Nassim Taleb puts it, “Hard work will get you a professorship or a BMW. You need both work and luck for a Booker, a Nobel or a private jet.”

When Kevin Kelly put forth his idea about having one thousand true fans, he wasn’t saying you’d live like a king. He wasn’t saying you wouldn’t have to work hard, or that the struggle would be over. He was saying that you’d be able to make a living. He predicted that technology had made it possible to work and survive as an artist. Nowhere did he say that it would be easy or that you’d be filthy rich.

As for being lucky? The football coach Bill Walsh once explained the coaching strategy behind his Super Bowl–winning San Francisco 49ers as not being rooted in a relentless, aggressive pursuit of victory, but as something a little more counterintuitive — something that embraces the role of chance. After designing the right standards and assembling the right members for the team, Walsh explained that his goal was to “establish a near-permanent ‘base camp’ near the summit, consistently close to the top, within striking distance.” The actual probability of winning in a given year depended on a lot of external factors — injuries, schedule, drive, weather—just as it does for any mountain climber, for any author, for any filmmaker or entrepreneur or creative. We do know with certainty, however, that without the right preparation, there is zero chance of successfully making a run to the summit.

Because, as Arthur Miller wrote in Death of a Salesman, successfully fulfilling our creative need is “greater than hunger or sex or thirst, a need to leave a thumbprint somewhere on the world. A need for immortality, and by admitting it, the knowing that one has carefully inscribed one’s name on a cake of ice on a hot July day.”

When I asked Craig Newmark what it felt like to know that he had created something used by millions of people, something that’s still going strong after twenty years, his answer was the perfect note to end this book on: “It feels nice for a moment, then surreal, then back to work.”


For a set of detailed case studies on books that I’ve worked on (which have sold millions of copies worldwide) plus additional, extended interviews with many of the brilliant experts quoted in this book, just send me an email at You can also go to


I’d thank my son, Clark, for his help, but to be perfectly honest he did not do anything to make this book possible.

James Altucher wrote a case study about writing, Choose Yourself, which you can read here:

Thanks to Robert Greene for suggesting I give Structure of Scientific Revolutions another chance many years ago. Here’s a history of the book: