Perennial Seller by Ryan Holiday


In *Perennial Seller: The Art of Making and Marketing Work That Lasts*, Ryan Holiday creates a playbook for writers, creators, and artists to make exceptional work and get noticed. And yes, those are two separate skills.

Creating great work is hard and takes time, but so is getting that work in front of other people. But, don’t think just because you’ve captured attention means your work will sell (look at this example of someone who had 2 million followers and couldn’t sell more than 50 items).

Creating work that lasts and marketing that work is two sides of the same coin. To create a true perennial seller, both skills are needed. You’ll learn the perfect formula for doing so in this book.


You can’t want to make something timeless, and then focus on metrics that aren’t

Holiday writes, “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.” Writers and business leaders want to create something that lasts a long time, but then agonize over social media followers and blog views–things that are pointless. People say they want to create timeless work, but then spend energy trying to figure out how to make their post go viral instead of how to make sure it lasts for 15 years. There’s a fundamental flaw there in the logic. “If you focus on near-term growth above everything else,” investor Peter Thiel writes, “you miss the most important question you should be asking: Will this business still be around a decade from now?”

Perennial, defined

A perennial seller is something that, over time, has continued success and finds an audience that loves the product, whatever it is. Perennial’s aren’t defined by their initial success, because the initial success is irrelevant if it’s going to last for 20 years.

The true act of creation is to make things that last

“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

If you want great marketing, start with a great product

No one who spends 1/4 of the time making and 4/5 of the time marketing will be a perennial seller. Making something worth buying, writing something worth reading is the first (and fundamental step) to creating timeless work. “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 co-founder of Evernote says, “People [who are] thinking about things other than making the best product never make the best product.” You start by *wanting* to make the best product.

Ideas are worthless

Everyone has ideas. Ideas for “the next big thing,” ideas for a book, ideas for how they want to turn their life around. But ideas are worthless. They mean nothing to the world. “The difference between a great work and an idea for a great work is all the sweat, time, effort, and agony that go into engaging that idea and turning it into something real. “Lots of people,” Austin Kleon says, “want to be the noun without doing the verb.”

Work on things that last (and don’t hurry)

As famous astronaut Jeff Bezos put it, “Focus on things that don’t change.” You can’t expect something to last if it’s built on top of, explains, or piggybacks off something that doesn’t last or is constantly changing.

The beautiful thing about writing and creating timeless stuff is that you don’t have to hurry. You’re not trend-chasing. If the thing is *truly* timeless, whether it comes out next month or in two years shouldn’t matter; it should be equally relevant. So take your time and make it great. “It’s better to play the longer game,” Holiday writes. “Leave behind the hype and ephemeral infatuations for the time capsule and the one-hit wonders.”

Great work is created little by little

“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.”

Inspiration is a function of doing the work

“Getting into action generates inspiration. Don’t cop out waiting for inspiration to get you back into action. It won’t!” – Robert Evans | Planning a project is important, but don’t get so bogged down in the details you forget to do the work. Plus, no matter how *perfect* the plan is, it’s just an idea if you don’t actually do the work on it. And remember what we said earlier about ideas?

You have to know who your project is for (and who it’s not for)

Charlie Rose asked the creator of Hamilton, Lin-Manuel Miranda, what set him apart from other kids he went to school with. Miranda replied, “Cause I picked a lane and I started running ahead of everyone else…” If you don’t know who you’re making something for, how do you know you’ve successfully created something? If you can’t identify who will buy your thing, why do you expect anyone to buy your thing?

Project brief: One sentence, one paragraph, one page

For every new project or creative endeavor write out exactly what your project is supposed to be, who it’s supposed to help, and what it’s supposed to do in one sentence, one paragraph, and one page. What are the things that matter and what are the things that don’t?

This is a _ that does _. This helps people .

What is it? Is it a modern piece of experimental art? Is it a low-budget YouTube video with friends? What genre is it in? Brain Koppelman, screenwriter and creator of Billions, told Seth Godin, “Everything that has a clear path to commercial success is in a genre.”

Jon Favreau, when dreaming up Iron Man, said in an interview once that his vision depended entirely in Robert Downey Jr. being Iron Man. Everything else–actors, set, story–revolved around him.

You must do this because, a Holiday writes, “An unaimed arrow rarely hits a target.”

Holiday’s “book about Stoic philosophy,” became, for an elevator pitch, “a book that uses the ancient formula of the Emperor Marcus Aurelius to teach people how to not only overcome obstacles but thrive because of them.”

Packaging matters

“A great package on a great product is what creates an explosive reaction,” Holiday writes. Catcher in the Rye sold well when it was first published, but sold over 1.25 million copies in the early pulp paperback edition. The cover was provocative and the blurb sucked you in: “This unusual book may shock you, will make you laugh, and may break your heart–but you will never forget it!”

You must stay focused (distraction is tempting)

“Nothing has sunk more creators and caused more unhappiness than this,” Holiday writes, “our inherently human tendency to pursue a strategy aimed at accomplishing one goal while simultaneously expecting to achieve other goals entirely unrelated.” If you want to create a new way of doing a non-profit, you can’t also expect to chase a big payday (and succeed). Seneca writes one must have, “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.” If you want to create a piece of timeless art, you can’t compare yourself to the people who are trying to get a billboard ranking next week or who are playing a different game altogether. A decade from now, you’re going to wish you stuck it out and kept pursuing the hard thing.

Anything that gets or keeps customers is marketing

Anything you do that creates new customers or keeps old ones is marketing: giving away a free chapter in a book, showing up to a local event and sponsoring it, signing books at a local book store, signing people’s emails up by hand.

Piracy is better than obscurity

Don’t be fooled into thinking your content or thing is so special that it can’t be given away for free. Tim O’Reilly said it best when he said, “The problem for most artists isn’t piracy, it’s obscurity.” Holiday continues, “we spend a lot of time insisting that nobody steal our work or get it for free…but we forget that being unknown is a far worse fate for an artist than being underpaid.” Cory Doctrow, a blogger and science-fiction author gripes on the same point: “Although it’s hard to turn fame into money in the arts, it’s impossible to turn obscurity into money in the arts.” This is especially true if you have another, high price paid offer like consulting or a course. If just one session of consultation or a speaking gig gets booked from free content, it’s worth it.

“Trade up the chain”

It’s tempting to want to start out on the biggest media outlet you can get, but it’s often smart to start small. Most outlets pick up stories from smaller ones. “By starting with a small podcast where I could tell the story on my own terms,” Holiday explains, “led to a pickup on a small site that covers a niche, and then sharing and spreading that piece out 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 in doubt, “newsjack”

The idea of “newsjacking” was popularized by David Meerman Scott and he defines it 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.” When everyone is talking about X, position yourself and your product to also talk about X.


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