Creating work that lasts from “Perennial Seller” by Ryan Holiday

No One Said It Was Easy… 15 Steps To Create Work That Lasts

Tips and Tricks from “Perennial Seller” by Ryan Holiday

Parker Klein ✌️
10 min readMar 3, 2024


1. Focus on the product first

All the marketing in the world won’t matter if the product hasn’t been made right.

Legendary investor and Y Combinator founder Paul Graham explains, “The best way to increase a startup’s growth rate is to make the product so good people recommend it to their friends.”

You can’t make something that lasts if it’s based on things, on individual parts that themselves won’t last, or if it’s driven by an amateur’s impatience.

2. Be patient. Put in the work

Art can’t be hurried. It must be allowed to take its course. It must be given its space — and can’t be rushed or checked off a to-do list on the way to something else.

“There is nothing to writing. All you do is sit down at a typewriter and bleed.” — Ernest Hemingway

If there is any magic in creative expression, it’s how small, even silly ideas can become big, important, awe-inspiring works if a person invests enough time in them.

Those who think they can rush their way to that finish line — or have complete confidence they will get there without breaking a sweat — end up disappearing just as quickly. It takes time and effort and sacrifice to make something that lasts.

“If it’s worth doing, it’s worth doing right.”

3. Play the long game

“If you focus on near-term growth above everything else, you miss the most important question you should be asking: Will this business still be around a decade from now?” — Peter Thiel

“If you listen to the greatest music ever made, that would be a better way to find your own voice to matter today than listening to what’s on the radio and thinking: ‘I want to compete with this.’ It’s stepping back and looking at a bigger picture than what’s going on at the moment.” — Rick Rubin

4. Pick your audience

Stephen King believes that “every novelist has a single ideal reader” so that at various points in the process he can ask, “What will ______ think about this?” (For him, it’s his wife, Tabitha.)

For any project, you must know what you are doing — and what you are not doing. You must also know who you are doing it for — and who you are not doing it for — to be able to say: THIS and for THESE PEOPLE. In some cases, that might be an enormous niche.

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.

5. You must be persistent

What are the chances that your prototype is perfect the first time? The Great Gatsby was rejected several times. WD-40 is named after the forty attempts it took its creators to nail the working formula.

“The first draft of anything is shit.” — Ernest Hemingway

No one can guarantee that your project will be a success, but it can be safely said that if you quit on it before your audience does, it’s guaranteed to fail.

“Success always requires an unstoppable author.” — Stephen Hanselman

6. Communicate how it will change people’s lives

Audiences can’t magically know what is inside something they haven’t seen. They have no clue that it will change their lives. You can’t be the self-conscious wallflower in the corner, hoping that people will see through the act and just know how great you are. Someone is going to have to tell them. It has to be obvious!

We have to take this thing that means so much to us and make sure that it is primed to mean something to other people too for generations to come. That it will stand out among a crowded field of other creators sincerely attempting to do the exact same thing. That it will be the best that it is capable of being and that the audience it is intended for is primed to love it. And the best person in the world to accomplish this difficult task? You.

There is nothing more badass for a reader than to see themselves as the hero. They also want to be able to see their friends, family, and colleagues — so they can recommend it to them.

7. Work on your pitch

In an elevator, when you’re actually pitching people, you’re also going to need to explain what ______ is, why there is a market for it, and why people should read it.

You’re going to have to describe to other human beings what this project is in an exciting and compelling way. 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.

“Speak in short one-sentence answers and don’t go in with all the legalese. Talk about the movie as a movie and the effect it will have on the audience from an emotional point of view. If you continue to be boring, I will hire an actor in New York to pretend that he’s Errol Morris. . . . Keep it short and keep selling it because that’s what is going to work for you, your career and the film.” — Harvey Weinstein

8. Focus on what you’re doing

If you’ve fallen into the sway of tracking your fellow creators on social media or you check the charts every week to see what other people are doing, you’re going to sap yourself of the discipline required to do what you are trying to do.

“What’s required is “confidence in yourself and the belief that you are on the right path, and not led astray by the many tracks which cross yours of people who are hopelessly lost, though some are wandering not far from the true path.” — Seneca

A person on a singular mission can’t be distracted; he can’t chase every colored balloon he comes across. If your goal is to create a perennial seller, you can’t measure yourself against people who aren’t aiming for the same thing — you can’t be endlessly checking industry charts or lists, and you can’t be distracted by the trends and fancies of other creators who are hopelessly lost.

9. Take responsibility

Adults create perennial sellers — and adults take responsibility for themselves. Children expect opportunities to be handed to them; maturity is understanding you have to go out and make them.

“Customers will not come just because you build it. You have to make that happen and it’s harder than it looks.” — Peter Thiel

Who is going to sell your movie, your app, your artwork, your service if not you? Even if you pay someone else a lot of money, how hard are they really going to work?

CEOs are very busy. They have meetings, phone calls, business dinners, and countless other day-to-day responsibilities. So, naturally, CEOs delegate the marketing to other people. But this is a huge mistake. If you delegate anything, you should delegate the chairmanship of the next fund-raising drive.

10. Be humble

Accepting your own insignificance might not seem like an inspiring mantra to kick off a marketing campaign, but it makes a big difference. Humility is clearer-eyed than ego — and that’s important because humility always works harder than ego.

It is my job as the marketer of my work to make people care, and that’s not going to be possible if I start with any illusions or entitlements. Instead, I’m going to start fresh. I’m going to win my readers, customers, and fans for the first time, one person at a time, all over again.

The mark of a future perennial seller is a creator who doesn’t believe he is God’s gift to the world, but instead thinks he has created something of value and is excited and dedicated to get it out there. Guess what? A sense of entitlement is not how you’re going to reach them. Hunger and humility make the difference.

11. Minimize your ask

When we say, “Hey, check this out,” we’re really asking for a lot from people.

The more you reduce the cost of consumption, the more people will be likely to try your product.

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.

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.

An effective strategy is to be cheaper and easier than the things they’re currently buying and using.

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.

12. Build relationships

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

Marc Ecko never asked for anything — he just made great work and sent it to select influencers he knew might appreciate it. Eventually, he got his first shout-out on the air, and the brand was never the same.

Always put yourself in their shoes: How would you feel if everyone wanted a piece of you? How would you feel if you got dozens of emails a day from total strangers trying to trick you into endorsing products, essentially for free? You’d be overwhelmed. Or you’d be jaded. The fact that most creators — especially big companies — just hire PR agencies to do this pitching for them is an opportunity for the DIY creators who don’t. Be a person. Be nice. Think relationship first, transaction second.

Treat everyone like they could put you on the front page of the New York Times . . . because someday you might meet that person.

The best time to have built your network was yesterday. The second best time is right now.

13. Start small

It’s better to start with smaller media and smaller features, then work your way up to the big score.

Make some noise. With the timeline we’re considering — years and years of relevance — in the end no one will remember being “offended” by something. The world will just remember having heard about it in the first place.

The real goal is establishing a presence or building a reputation and profile. Publicity is about temporarily breaking through the noise — if only for a single news cycle — and contributing to the word of mouth that a product eventually needs to succeed.

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. (I don’t assume it should be interesting to them because it’s interesting to me. I make it interesting, period.) There’s no real trick to it other than that. Nor does there need to be. If there is a secret to media, it is in the work you’ve made — in the risks you take and the things you do.

What many creators fail to realize is that the media is desperate for material. Reporters sit around all day hoping to find good stuff, anxious to beat their (many) competitors in getting to it.

14. Do things that aren’t sexy

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 resource 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.

Audiences often need to hear about things multiple times and be exposed to them from multiple angles before they’re willing to give something a chance.

“I urge authors to consider how long it took them to write their books and see them published and to devote at least that much time to pushing them.” — Barbara Hendricks

15. Keep creating

The best marketing you can do for your book is to start writing the next one. More great work is the best way to market yourself.

Woody Allen goes for “quantity” as a way to get to quality. “If you make a lot of films,” he said, “occasionally a great one comes out. Films never come out in the end how you expect them to at the start.”

“If you do something and it turns out pretty good, then you should go do something else wonderful, not dwell on it for too long. Just figure out what’s next.” — Steve Jobs

Don’t be afraid to try crazy things. Don’t let your brand tie you down to the point where you don’t explore or experiment. It is precisely these little endeavors that might illuminate a new direction for your career. They might expose you to a new community or group who will eat up your other work.

We have to try to leave our mark nonetheless, and try not only once, but again and again.

“It feels nice for a moment, then surreal, then back to work.” — Craig Newmark

#UseTwos ✌️

Use code “baller”

Save this list in Twos ⬇️

Read all of my notes on “Perennial Seller” by Ryan Holiday ⬇️



Parker Klein ✌️

Former @Google @Qualcomm @PizzaNova. Building Twos: write, remember & share *things* (