Perennial Seller by Ryan Holiday

I finished this book in April, 2025. I recommend this book 7/10.

Why you should read this book:

Ryan Holiday knows a thing or two about marketing. In this book, he shares how to market your product without a billion dollar investor or huge marketing budget. But rather than trying to strike it rich with one big lucky swoop, you dig in for the long haul. How you have to be the champion of your creation and push it up the mountain.

Get your copy here.

🚀 The book in three sentences

1. Make excellent content

2. You have to champion it all the way

3. Don't count on luck or fame; do the work

   
   

📝 My notes and thoughts

• P3. People claim to want to do something that matters, yet they measure themselves against things that don't, and track their progress not in years but in microseconds. They want to make something timeless, but they focus instead on immediate payoffs and instant gratification.

• P24. This is not a question of "purity." It's simple. Compare two creators: one who cares less about what he's making and more about what it can do for him (make money), and another who, upon sitting down, says, "This is my life's work" or "this is what I was put on this planet to make." Who would you bet on? Every project must begin with the right intent. It might also need luck and timing and a thousand other things, but the right intent is nonnegotiable—and, thankfully, intent is very much in your control.

• P46. The absence of an intended audience is not just a commercial problem. It is an artistic one. The critic Toby Litt could have been talking about all bad art and bad products when he said that "bad writing is almost always a love poem addressed by the self to the self." What audience wants that? The best way I've found to  avoid missing your target—any target—entirely is to identify a proxy from the outset, someone who represent your ideal audience, who you then think about constantly throughout the creative process. Stephen King believes that "every novelist has a single ideal reader" so that at various points in the process her can ask, "What will ... think about this?" (For him, it's his wife, Tabitha.) Kurt Vonnegut joked that you have to "write to please just one person. If you open a window and make love to the world, so to speak, your story will get pneumonia." 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 a person—a real person you know, or an imagined person—and write to that one."

• P49. 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 would should be either "very entertaining" or "extremely practical." Notice they didn't say, "Should be very fulfilling to your personally" or "Should make you look super smart" or "Capitalize on some big trend." Those concerns are either secondary or implied. It's better to be focused on those two timeless use cases of enjoyability or utility.

• P51. So the creator of any project should try to answer some variant of questions. In short: What are these people going to be paying for? If you don't know—if the answer isn't overwhelming—then keep thinking.

  • What does this teach?

  • What does this solve?

  • How am I entertaining?

  • What am I giving?

  • What are we offering?

  • What are we sharing?

• P53. Being brave and brash is not only more fun creatively, it saves you from going head-to-head with the Facebook (a social network with billions of dollars in revenue) or the Catcher in the Rye of your space. It saves you from a costly war of attrition that you will likely lose. The higher and more exciting standard for ever project should force you to ask questions like:

  • What acred cows am I slaying?

  • What dominant institution am I displacing?

  • What groups am I disrupting?

  • What people am I pissing off?

• P54. With Born to Run, Bruce Springsteen said he was trying to make a record that would "grab you by the throat and insist that you take that ride, insist that you pay attention." He said he was aspiring to make the "greatest rock record [he'd] ever heard." Brashness, newness, boldness—these attitudes are not at all at odds with perennial sales. In fact, it's an essential part of the equation. Stuff that looks, sounds, reads, and performs like everything else in its field today has very little chance of standing out tomorrow. That's exactly what you don't want.

• P59. "I think what we do is to tell the best story we can, the best way we can, and produce it in the best way possible, and then see how the world reacts to it." Ignore what other people are doing. Ignore what's going on around you. There is no competition. There is no objective benchmark to hit. There is simply the best that you can do—that's all that matters.

• P66. It's not "promotion" we're talking about here—that comes later. Instead, prior to release, considerable efforts needs to be spent polishing, improving, and, most critically, positioning your project so that it has a real chance of resonating with the intended audience. Even the most delicious dish must be properly plated (and presentation affects the taste—that's a fact). The difference between a nice contemporary hit and a lasting icon is made in these decisions, and this process is not necessarily done quickly. It may be that the editing and refining of a work may take as long as the initial flurry of creation—it could be that the last mile takes longer than all the others put together.

• P89. You must create room for the audience to inhabit and relate to the work. You must avoid the trap of making this about you—because, remember, you won't be the one buying it. In a way, Robert's insistence on diversity wasn't coming only from his very real sense of fairness and tolerance. There was a genius business logic to his choices as well: Each master was a conduit in to a new community to whom the book might appeal and be promoted. This was a marketing asset—or rather, a pre-marketing asset—built directly in during the writing and editing phases.

• P97. At some point in the near future (the third section of this book), you're going to have to describe to other human beings what this project is an exciting and compelling way. You're going to need to explain to reporters, prospective buyers or investors, publishers, and your own fans:

  • Who is this for

  • Who this is not for

  • Why it is special

  • What it will do for them

  • Why anyone should care

• P113. Your product needs a champion. 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." That must be you. Marketing is your job. It can't be passed on to someone else. There is no magical firm who can take it totally off your hands. Even if you're famous, even if you have a million Twitter followers, even if you have a billion dollars to spend or fancy credentials—it's still on you and it still won't be easy. It's on you to take this great thing you've made and reach as many people as possible with it.

• P127. However many of these relationships you have, however tenuous or weak you might feel they are, put them all in a spreadsheet. Lay it all out—names, outlets, promises, debts—and see what you've got to work with. If it's a tiny spreadsheet, that's okay. If that is the case, though, I'd take a minute to consider what this says. Is it that you'll need to go it alone and make up for this lack of resources with extra hustle and intensity? Or would waiting until you 're better supplied and prepared make the most sense? A general wouldn't even think about going into battle without knowing how many troops and weapons and supplies he has. And he certainly wouldn't go into battle if he determined that he didn't have enough of any one of those things to make the difference.

• P133. Which is why as creators we have to get more comfortable with giving people a taste of your work—or, in some cases, giving some people the entire meal for free. That 's how we build an audience and gather momentum. I think you'll find you're already more comfortable with this idea than you know. Would you charge a reporter if she wanted to try your product? If a celebrity walked into your resturant, wouldn't you comp his meal? If you heard that a social media star with millions of followers loved your stuff, would you think twice about mailing her a bunch of it? Our initial audience is just as important. We have to get them hooked somehow, and free is often the best way to do it. Many of the much bigger, much more profit-focused companies have to accept this same uncomfortable fact of modern life too. How may of your friends mooch off somebody else's HBO or Netflix account?

• P164. Meanwhile, there are plenty of easier things they haven't done or don't want to do that would produce results right now. Taking time off work or hiring a babysitter so you can write fifty personally crafted emails—that's hard and unsexy. Paying for a plane ticket and a hotel so you can give a talk at a major nonprofit—that's time and resources intensive. Joining a group or a cause to build relationships you can draw on later—hard, unsexy, and difficult to quantify. Spending serious money to create samples and give them away to targeted audiences? That's hard and understandably, feels like the opposite of selling. Working on improving your product until it screams "Share me with everyone you know"—that's less fun than buying a back-page ad that everyone (who still reads newspapers) will see. Most people wish they could just cut a check and be done with it. They'd like to see the tangible results of their promotion in newsprint on the morning of launch day. I've felt those same impulses—paying for media always seems easier than earning it—but they are worth resisting. Save your money.

• P170. A perennial producer requires perennial marketing. Yes, we want to start off strong—but we need to stay strong. For this reason, our efforts need to be lean. We can't rely on a silver bullet—we need a cache of lead bullets. Which is why if you have to choose between spending money to pay for a publicist or buying your own products and giving them away to the right early adopters, you should go with the latter every time. One is a direct route to word of mouth; the other is a detour and depends on being at the right place at the right time in the right news cycle.

• P193. Never dismiss anyone—you never know who might help you one day with your work. His rule was to treat everyone like they could put you on the front page of the New York Times...because someday you might meet that person. Play the long game—it's not about finding someone who can help you right this second. It's about establishing a relationship that can one day benefit both of you. Focus on "pre-VIPs"—The people who aren't well know but should be and will be. It's not about who has the biggest megaphone. A great example for me was meeting Tim Ferriss. He hadn't sold millions of books then and didn't have a huge platform. Now he does. 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).

• P202. Ian Fleming once wrote to his publisher, "I bet your other authors don't work as hard for you as I do." He was right. Most think they're too good for it, or they are too sensitive to push hard enough. I remember early on I asked my agent what separated his bestselling clients from his small ones. He said, "Success almost always requires on unstoppable author." Throughout my career, I've seen this played out not just in books but in all products.

• P208. "You go from project to project with your heart in your mouth," John McPhee has said. Abandoning proven material or comfortable stomping grounds to start from scratch is a scary prospect because, as McPhee reminds us, "Your last piece will never write your next one for you." Each time you do this, it not only increasers your mastery in your chosen craft, but as a result it also increases your odds of creating something brilliant and lasting. The key is that you must do it—you must create, create, create.

• P213. "[Our] new environment may well select for artists who are particularly adept at inventing new career paths rather than single-mindedly focusing on their craft." In other words, it's favoring people who can move horizontally and integrate vertically, who can create innovative empires, not just produce work. Some questions to ask yourself:

  • What are new areas that my expertise or audience would be valuable in? (Think of celebrities investing in companies or starting their own.)

  • Is it possible to cut out the middleman like a label or a VC and invest in myself? (Like when musicians buy back their masters or authors get their rights reverted. Jay Z has famous line that sayd if you don't own your masters, you're a slave—which is partly true.)

  • Can I help other artists or creatives achieve what I have achieved? (Be a consultant, coach, or publisher/label head/ producer.)

  • What are other people in my field afraid to do? What do they look down on? (These are almost always great opportunities.)

  • What can I do to make sure that I am not dependent on a single income stream? (You never know what can happen.)

  • If I took a break from creating, what would I do instead? (Maybe there is some long-lost passion to rekindle.)

  • What are part of the experience or community surrounding my work that I can improve or grow? (Live events, conferences, memberships, personalized products, etc.)

• P224. 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 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.