Ryan Holiday’s Advice on What it Takes to Build Something that Sells Forever

The dream of every creative is to do some work that lives on forever. Work that is referred to in the annals of their industry as a defining work. Something that continues to sell, more and more as the years go on.

To build a perennial seller. That’s exactly what Ryan Holiday’s book, Perennial Seller, is attempting to teach you to do.

Is that not the kind of lasting success that every creative person strives for? To produce something that is consumed (and sells) for years and years, that enters the “canon” of our industry or field, that becomes seminal, that makes money (and has impact) while we sleep, even after we’ve moved on to other projects?

The book is split up into two broad sections. The first half of the book is telling us what a Perennial Seller looks like and what it’s going to take to build a product worthy of the mantle. The second half of the book is all about what it takes to tell people about that product so that what you’ve built can become something that sells regularly. If you’re not marketing a product, then no one is doing it for you.

Inside the two broad sections, there are two smaller divisions which give us four ideas around which the book is centred.

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

The beginning of the book sets the stage with a bunch of talk about where you need to focus in broad strokes if you want to build a product that lasts.

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.

And how we sabotage ourselves in the midst of making some attempt to build something that lasts.

And how to avoid falling for the seduction of short-term notability to focus on the real brass ring: Long-term success and renown.

And finally how almost every incentive that is lauded as something worthwhile is the exact opposite thing from what we should be aiming for if we want to build a creative work that lasts.

The truth is that they never give themselves a real shot at it. They fail because, strategically, they never had a chance. Not when almost every incentive, every example, every how-to guide they look to, even the cues they take from well-meaning fans and critics, leads Thom in the wrong direction.

Before you move further in this review, take a step back and write down how you measure success. Do you measure it against short-term things? Are you watching all those ‘stars’ around you for queue on what you should be doing?

Maybe don’t.

Part I: The Creative Process

Ryan Holiday started his writing career with Trust Me I’m Lying, which was an expose on how the media worked. His main gig is Brass Check which is a marketing firm. When he says that we prioritize marketing and sales over building a great product he knows of what he speaks.

While there are many different types of success in this world, and prioritizing marketing and sales over the product may lead to some of them, that is not how perennial success is created.

His job at Brass Check is to take a great product and help turn it into something that sells. In this book, he talks about working with James Altucher on a book and sending him back over many revisions to build something that was awesome instead of mediocre.

To be great, one must make great work, and making great work is incredibly hard. It must be our primary focus. We must set out, from the beginning, with complete and total commitment to the idea that our best chance of success starts during the creative process.

No marketing can save mediocre work. Mediocre work will have mediocre sales that will peter out. If that’s not what you want, and I’m assuming it’s not, then this first section is all about what it takes to build a creative product that blows people’s minds.

Building something that is awesome isn’t just having the idea for something awesome. It takes hard work. You will not build it, and they will not come.

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. The difference is not trivial. If great work were easy to produce, a lot more people would do it.

It will take hard work to build that business you want. The coaching clients that I work with that don’t see change are the ones that come back week after week and say they didn’t do the work we agreed they’d be doing.

They’re also the ones that I fire because I hate wasting my time. Are you willing to do the hard work it will take to build something that’s worth keeping around for the long term?

Remember that hard work is…hard. It requires giving something up.

In the course of creating your work, you are going to be forced to ask yourself: What am I willing to sacrifice in order to do it? Will I give up X, Y, Z? A willingness to trade off something — time, comfort, easy money, recognition — lies at the heart of every great work. Sometimes more, sometimes less, but always a significant sacrifice that needs to happen. If it didn’t everyone would do it.

Around my house, I give up TV almost every night of the week. Last night I read and then had an idea for a blog post I sketched out while I talked to my wife and she sewed. Netflix was put forward as an option, but turned down because we couldn’t sit together and watch something.

We didn’t say this, but we both decided to sacrifice easy entertainment in the face of something that was far more valuable for the long term. She made a beautiful dress for herself, and I learned more about running an awesome business.

Another great thought in this section is the idea of divorcing ourselves from the ‘easy and instant’ culture out there. While some awesome creative works can be built in a flash of inspiration and a few hours, most of them will take more time than you figured they would.

In the way that a good wine must be aged, or that we let meat marinate for hours in spices and sauce, an idea must be given space to develop. Rushing into things eliminates the space.

They’ll require testing. That may mean testing your book ideas in blog posts to better understand how you think about the ideas at the same time as gauging which ones resonate with your audience.

One of the ideas that I tested recently was my thoughts on saying NO to prospects that want to become clients when I spoke at WooConf 2017.

But when Rubin says that the best art divides the audience, he means that it divides the audience between people who don’t like it and people who really like it.

When I got my ratings, I either had full marks for being awesome or was called an ass. More people thought it was a great talk, but knowing that the idea was polarizing is perfect1.

The final great idea is the one that you must be scared of doing justice to your idea if it’s an idea that’s worth doing.

The more nervous and scared you are — the more you feel compelled to go back and improve and tweak because you’re just not ready the better it bodes for the project. Because your goal is one that should make any rational person tremble a bit.

The next book I read was Finish by Jon Acuff2. That book is all about not chronically starting new projects but finishing. It’s funny to read the advice in Finish about not worrying so much about perfection and instead get things shipped.

The two books are for different audiences. Where Perennial Seller is for Ready, Fire, Aim types3 Finish is for Ready, Ready, Ready, Aim, Aim, Aim some more types.

Which book resonates best with you depends on what you suffer from most. I’m more in the camp that needs to read Perennial Seller.

As you leave this section, remember that great creative work is not the product of a lightning strike. It’s hard-won hard work that requires focus and sacrifice.

Part II: Positioning

What’s the dream of the creative? I spoke about it recently at a local event. We dream that we will do work and that the masses will love it. The publisher will publish it without any revisions.

That’s a fantasy land.

Deep down, we all harbor a fantasy: We do creative work, throw it in the mail — someone else sends us a contract and doesn’t bother us again. No one gets to tell us what do to; our art remains pure and untouched.

Well, it’s time to abandon that desire and focus on what it’s going to take the amazing creative work you did and market it.

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.

In this section, Holiday says that we should at least be taking the same amount of time we took to build the product, to market it. You’re not done when you launch; you’re just barely starting.

If something isn’t selling, then remember it’s your fault.

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.

But this task of showing your work to the outside world starts before you launch your product. It starts in the first section as you were testing your ideas in the mainstream.

The fact is, most people are so terrified of what an outside voice might say that they forgo opportunities to improve what they are making. Remember: Getting feedback requires humility. It demands that you subordinate your thoughts about your project and your love for it and entertain the idea that someone might have a valuable thing or two to add.

I was recently talking with a friend that sold his company for a few million, and we both were in firm agreement that almost no one is going to steal your idea. First, they have their own ideas already and aren’t executing on them. Second, only you can do your idea your way.

That means, share your ideas. No one is going to steal them. If you can only find people that love your idea, work to find people that hate your idea. Find people to give you criticism so that you can take that and use it to refine your work.

Holiday is also a proponent of building around a niche at least at first4. Start with what makes you unique. Once you have an audience, you can branch out, but at first, you need that niche so that you can market effectively.

For creators, it is typically easier to reach the smaller, better-defined group. If you reach the smaller group and wow them, there will be many opportunities to spread outward and upward.

The final big idea from this section is an echo of what he talked about in the beginning. Don’t follow in-the-moment success if you want to achieve something that sticks for a long time.

I’ll leave you with these three quotes from the book. Stop and ask yourself again, what instant recognition are you looking for? How is it holding you back?

If your goal is to make a masterpiece, a perennial seller for a specific audience, it follows that you can’t also hope it’s a trendy of-the-moment side hustle.

Likewise, 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.

Too many creators are distracted by critics, by prizes, by buzz or media attention or impressing their friends, and they forget this. They forget their audience, customers, fans.

Part III: Marketing

This section is all about getting your work out to the people that will be interested in it and starts with a sobering reminder about your competition.

We are fighting not just against our contemporaries for recognition, but against centuries of great art for an audience. Each new work competes for customers with everything that came before it and everything that will come after.

Stop and think about that as you look at your offerings. What makes you stand out from all the others? A great question to ask yourself is: “If my company or customers wanted someone much better than I am, what would that person look like?”

Then become that person. Put those practices into your business so that you are the business your customers are looking for.

One of the fundamental concepts of this section is that you need to build word of mouth marketing if you want your product to keep selling because you can’t always be ‘on’.

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.

That should start with finding a niche and marketing to it5.

When my company works with musicians, we start by finding the most obscure and specific outlets you can think of.

The point to finding more and more obscure niches is that you can find one that you match with perfectly. Other influencers will follow deep niche sites, and you’ll get on their radar. Then you can expand out to a wider audience.

But just like Dash says in the Incredibles when his mom says that “everyone is special”, “That’s the same as saying no one is.” When you’re focusing on everyone or people like me, you’re focused on no one.

Once you’ve found that niche, you need to make sure that your product is easy to get into the hands of people. Holiday suggests that pricing very inexpensive at first is a great way to get your product into the hands of many people.

You can’t do this always, but remember with books particularly, you’re not going to become a millionaire. The books are almost always an introduction to some other offering.

Even after giving a lot of books away to drive discovery, at some point I would have to begin to charge, or that discovery wouldn’t be worth much. It’s quite rare where “free” is a strategy that works indefinitely. This is business, after all.

Another strategy is to get on the radar of an influencer and then stay on it.

When you find an influencer who likes your product, hold on for dear life. (Send them more stuff than they know what to do with — chances are they have influencer friends!)

When this influencer loves your work, they’ll share it, and you’ll build a wider audience. Remember, this influencer is gold so treat them like that. Send them thank you cards or something. Continually impress them.

Near the end, Holiday revisits the idea of taking a stand again and getting your work out there. You may have the next great novel in you, but if it stays inside, it doesn’t matter because no one will ever see it.

…no one gets coverage for thinking about doing something. You get coverage for taking a stand, for risking something, for going out there and creating news where there wasn’t any before. You don’t get coverage for what you feel or what you believe. Only what you do with those beliefs or feelings.

If you want attention, then you need to get your work out there. You need to take a stand in your niche and likely offend some people. If no one is telling you that you’re wrong, you may not have anything worthwhile to say.

Part IV: Platform

The final section is about the platform you have, or for some the platform you don’t have and never spent the time building.

Everyone wants a platform when they need one. People want to have a big list — they just don’t want to lay the groundwork for one beforehand.

If you want to launch a product next year, you need to start building a platform now. When I talk to clients about blogging, we keep it simple. A 2 line about page and then start writing. The only thing we add to that is a basic email list that emails the blog posts that get published.

You’re always trying to get the most direct connection with the people that like your ideas. That connection is your platform.

Becoming a perennial seller requires more than just releasing a project into the world. It requires the development of a career. It means building a fan base both before and after a project, and it means thinking differently than most people out there selling something.

Having a platform means that after you write that book, you have more stuff to say. You continue to have points for your followers to engage with you.

The best marketing you can do for your book is to start writing the next one.

While you spend time marketing the work you’ve just finished, you keep thinking about ideas for the next book and then when you’re finishing out the marketing for your current work, you start the next one.

The people that bought your first work will have some overlap with your second item and your third. Your second and third will reach different people, and some of them will look back at the other stuff you’ve done and get that as well.

The final thing that Holiday addresses in his conclusion is luck and the admission that luck plays a part in creating something worth the time of others.

It would be dishonest to talk about creating a classic, perennial seller and pretend that luck has nothing to do with it because luck matters a lot.

Luck is more than just random happenings though. It’s hard work and watching for the right opportunity to push the buttons hard. Like that right influencer finding you and then continuing to nurture that relationship.

Remember:

The more you do, the harder you work, the luckier you seem to get.

Recommendation for Perennial Seller by Ryan Holiday

As I said earlier, I’m a Ready, Fire, Aim type so this book was right up my alley. It made me rethink the current quarter goals and not worry so much about getting three books out in a quarter.

I got the video course out and did an awesome job on it. I learned some stuff about running it that would have been much harder to learn if it sold all the copies I originally wanted to. The other two books are going, but only one of them is likely to happen this year. The other will happen in 2018.

If you’re someone who starts a bunch of stuff but rarely finishes, then you should read Finish by Jon Acuff instead. It’s more about not getting stuck by perfectionism.

Then once you’ve got over some of your perfectionist hurdles, read Perennial Seller to get a great set of insights into what it takes to build something that’s worth purchasing decades from now.

Get Perennial Seller on Amazon
If you want to dive deeper into marketing check out my further reading on content marketing


  1. Members of my site will be getting a version of the talk in 2018 as bonus content as well. 
  2. I reviewed Finish already if you’re interested
  3. Yes that’s me 100%. I also burn bridges before I should. 
  4. He talked more about this on a recent Blinkist episode you should listen to
  5. Yes I wrote a book just about this call…Finding and Marketing To Your Niche
Perennial Seller: The Art of Making and Marketing Work that Lasts Book Cover Perennial Seller: The Art of Making and Marketing Work that Lasts
Ryan Holiday
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July 18 2017
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Bestselling author and marketer Ryan Holiday calls such works and artists perennial sellers. How do they endure and thrive while most books, movies, songs, video games, and pieces of art disappear quickly after initial success? How can we create and market creative works that achieve longevity?