Perennial Seller by Ryan Holiday: Summary & Notes


I’m a big fan of Ryan Holiday in general, and this book is another good one.

Generally an instruction manual for exactly what the title says: “Making and Marketing Work that Lasts”.  It’s one of his most actionable books, going into detail about the pre-, during and post-process of creating great work.  

Some of the most interesting parts of the book for me:

  • The creative process is one that meanders, develops and evolves over time. There’s no “lightning strike”, but rather “to make genius - you just have to have small moments of brilliance and edit out the boring stuff.”
  • The best way he suggests resonating with your audience is identifying a “proxy” from the outset, someone who represents your ideal audience, and then think about them throughout the creative process.
  • Suggested price to create a perennial seller? “As cheap as possible without damaging the perception of your product.”
  • “Create word of mouth.”

Definitely worth reading for any entrepreneurs, creators or artists alike.

Favorite Quotes

  • 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,” as the poet and artist Austin Kleon puts it, “want to be the noun without doing the verb.”
  • Art is the kind of marathon where you cross the finish line and instead of getting a medal placed around your neck, the volunteers roughly grab you by the shoulders and walk you over to the starting line of another marathon.
  • A book should be an article before it’s a book, and a dinner conversation before it’s an article.
  • “Either you’re controversial,” as the perpetually controversial writer Elizabeth Wurtzel advises creatives, “or nothing at all is happening.”
  • Nothing has sunk more creators and caused more unhappiness than this: our inherently human tendency to pursue a strategy aimed at accomplishing one goal while simultaneously expecting to achieve other goals entirely unrelated.
  • The most newsworthy thing to do is usually the one you’re most afraid of.

Detailed Notes


  • In other words, classics stay classic and become more so over time. Think of it as compound interest for creative work.
  • What if we start by just trying to make something that lasts longer than average?

This book examines every part of the process from the creative act to creating a legacy. 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

  • 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.
  • It’s why all the pre-work matters so much. The conceptualization. The motivations. The product’s fit with the market. The execution. These intangible factors matter a great deal. They cannot be skipped.
  • Above all, they have to want to produce meaningful work—which, I can say from experience, is often not the goal of the people in the creative space.
  • 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,” as the poet and artist Austin Kleon puts it, “want to be the noun without doing the verb.”
  • Why Create?
  • You must have a reason— a purpose— for why you want the outcome and why you’re willing to do the work to get it.
  • That purpose can be almost anything, but it has to be there.

Here are some good ones:

  • Because there is a truth that has gone unsaid for too long.
  • Because you’ve burned the bridges behind you.
  • Because your family depends on it.
  • Because the world will be better for it.
  • Because the old way is broken.
  • Because it’s a once-in-a-lifetime moment.
  • Because it will help a lot of people.
  • Because you want to capture something meaningful.
  • Because the excitement you feel cannot be contained.
  • These are the states of being that create great works of art— not passing or partial interest— and these are the states you should be seeking out.

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.
  • Art is the kind of marathon where you cross the finish line and instead of getting a medal placed around your neck, the volunteers roughly grab you by the shoulders and walk you over to the starting line of another marathon.
  • Art can’t be hurried. It must be allowed to take its course.
  • A truly successful band, or filmmaker, or entrepreneur— one whose career lasts decades— must think bigger and more long term than that.
  • Indeed, many studies have confirmed that creativity isn’t like a lightning strike. A creative work usually starts with an idea that seems to have potential and then evolves with work and interaction into something more.
  • Creative people naturally produce false positives.
  • 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.
  • 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.
  • How we put this into practice is simple:

Ask questions.

  • How can I give people a sample of what I’m thinking?
  • How does the idea resonate in conversation?
  • What does an online audience think of it?
  • What does a poll of your friends reveal?

These might seem like small questions in the face of a big task like creating a classic work that lasts— but classics are built by thousands of small acts.

  • Focusing on smaller, progressive parts of the work also eliminates the tendency to sit on your ass and dream indefinitely.
  • An audience isn’t a target that you happen to bump into; instead, it must be explicitly scoped and sighted in. It must be chosen.
  • Successfully finding and “scratching” a niche requires asking and answering a question that very few creators seem to do: Who is this thing for?
  • 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.
  • Let’s be clear: You can’t afford to wait until after it’s finished to figure out who what you’re making is for. Why? Because too often the answer turns out to be: no one.
  • The best way I’ve found to avoid missing your target— any target— entirely is to identify a proxy from the outset, someone who represents your ideal audience, who you then think about constantly throughout the creative process.
  • 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?
  • the key to success in nonfiction was that the work should be either “very entertaining” or “extremely practical.”
  • You want what you’re making to do something for people, to help them do something— and have that be why they will talk about it and tell other people about it.
  • The bigger and more painful the problem you solve, the better its cultural hook, and the more important and more lucrative your attempt to address it can be.

So the creator of any project should try to answer some variant of these questions:

  • What does this teach?
  • What does this solve?
  • How am I entertaining?
  • What am I giving?
  • What are we offering?
  • What are we sharing?
  • Srinivas Rao, “Only is better than best.” (Try to be the only one who is doing what you’re doing)
  • 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?
  • “Either you’re controversial,” as the perpetually controversial writer Elizabeth Wurtzel advises creatives, “or nothing at all is happening.”
  • The point is that you cannot violate every single convention simultaneously, nor should you do it simply for its own sake.
  • So we ask ourselves: Why are things the way they are? What practices should be questioned and which should remain sound?
  • I’ve come to realize that these are the tracking signs of a work that lasts. You want to provoke a reaction— it’s a sign you’re forging ahead.
  • 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.
  • A master is painstakingly obsessed with the details.
  • 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.

Part II: POSITIONING: From Polishing to Perfecting to Packaging

  • Audiences can’t magically know what is inside something they haven’t seen. They have no clue that it will change their lives.
  • Once you understand that this project’s chances of success or failure rest entirely on you, you must undertake a paradoxical and difficult task: finding and submitting your work to the feedback of a trusted outside voice (or, in some cases, voices).
  • Nobody creates flawless first drafts. And nobody creates better second drafts without the intervention of someone else. Nobody.
  • Put the website or the beta version of your app or your manuscript aside and grab a piece of paper or open a blank Word document. Then, with fresh eyes, attempt to write out exactly what your project is supposed to be and to do in . . .
  • One sentence.
  • One paragraph.
  • One page.
  • This is a ______ that does ______. This helps people ______.
  • Fill in this template at the three varying lengths.
  • “Everything that has a clear path to commercial success is in a genre.” - Seth Godin
  • This is why creators must know which variable( s) the project will hinge on. They must know which conventions of the genre they are observing and which ones they are taking a risk on by tweaking or subverting.
  • The most important part of the process is comparing the results of the exercise against the product we’ve made.
  • Too rarely, creators forget to consciously stop and compare their first attempt against their goal.
  • You must be able to explicitly say who you are building your thing for. You must know what you are aiming for— you’ll miss otherwise. You need to know this so you can make the decisions that go into properly positioning the project for them.
  • You need to know this so you can edit and refine the work until it’s so utterly awesome that your target group cannot resist buying it.
  • Marketing then becomes a matter of finding where those people are and figuring out the best way to reach them.
  • 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?
  • Today, in order to even have a chance at people’s attention, your project has to seem as good as or better than all the others. Three critical variables determine whether that will happen: the Positioning, the Packaging and the Pitch.
  • Positioning is what your project is and who it is for.
  • Packaging is what it looks like and what it’s called.
  • The Pitch is the sell— how the project is described and what it offers to the audience.
  • 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.
  • 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 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
  • What is it that you want? What is truly motivating you? What are you trying to accomplish with this project? The answer should be clear by now: I am making a ______ that does ______ for ______ because ______.
  • There are many different missions. Whatever yours is, it must be defined and articulated. Once that has occurred, there is one last thing you must do. You must deliberately forsake all other missions.
  • Nothing has sunk more creators and caused more unhappiness than this: our inherently human tendency to pursue a strategy aimed at accomplishing one goal while simultaneously expecting to achieve other goals entirely unrelated.
  • With a perennial seller as your goal, the track is clear: lasting impact and relevance.
  • “Selling out” is the label that so many creatives are afraid of being branded with. That’s absurd— as though there were some single standard of what artistic credibility and audience should be.
  • Perhaps to you success is a RAV4, whereas to someone else it’s a Bentley. I bought my wife a RAV4 with the income from my books. I like to drive it sometimes. It’s actually pretty nice. You know what that says about my work? Absolutely nothing. It’s a car.
  • You cannot expect to sell unless you’ve put the work in and made the sacrifices and decisions that allow success to happen. You have to be ready for what comes next: the real marathon that is marketing.

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

  • Marketing is anything that gets or keeps customers.
  • To have work that lasts, you can’t have a mediocre product or be a moron. You have to be brilliant at all of it.
  • “[Each project] needs somebody who says, ‘I am going to make this succeed,’ and then goes to work on it.” - Peter Drucker
  • That must be you. Marketing is your job. It can’t be passed on to someone else.
  • While marketing is a job and it’s your job, it’s also a fun and worthwhile job. You’re selling something you believe in, that you’re invested in, and that you know people will like.
  • Accepting your own insignificance might not seem like an inspiring mantra to kick off a marketing campaign, but it makes a big difference.
  • I remind myself: People are busy. They have no idea why they should care about this thing.
  • The only way the job will get done— to make people care— is if we do it ourselves.
  • Guess what? A sense of entitlement is not how you’re going to reach them. Hunger and humility make the difference.
  • We discover things by word of mouth.
  • 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.
  • A product that doesn’t have word of mouth will eventually cease to exist as far as the general public is concerned. Anything that requires advertising to survive will— on a long enough timeline— cease to be economically feasible.
  • Our marketing efforts, then, should be catalysts for word of mouth. We are trying to create the spark that leads to a fire.
  • From a marketing perspective, a proper launch is essential— much more than simply picking a random day to go live.
  • Yes, “launch windows” are artificial. But just because something is constructed, as I once heard a wise person say, that doesn’t mean it isn’t important.
  • The component parts of a launch— media, relationships, influencers, advertising, creating content— all take time and effort.

What Do We Have to Work With?

Other than the “when,” the most important part of a launch is the “what”— as in: What are we working with here?

Stuff like:

  • Relationships (personal, professional, familial, or otherwise)
  • Media contacts
  • Research or information from past launches of similar products (what worked, what didn’t, what to do, what not to do)
  • Favors they’re owed
  • Potential advertising budget
  • Resources or allies (“ This blogger is really passionate about [insert some theme or connection related to what you’re launching].”)
  • It is essential to take the time to sit down and make a list of everything you have and are willing to bring to bear on the marketing of a project.
  • 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.
  • For books, the free strategy is possible in a variety of iterations. Authors can give away whole chapters, excerpts as articles, or a free preview— or they can give the whole thing away for free to a select audience, or have events or sponsors buy copies that are in turn given away for free.
  • Today, smart creators realize that the bigger the audience they can reach with their music, the better.
  • We have to get them hooked somehow, and free is often the best way to do it.
  • humor writer George Ouzounian, also known as Maddox from, has given away almost 100 percent of his writing for free— without ads—
  • It’s quite rare where “free” is a strategy that works indefinitely. This is business, after all.
  • 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.
  • 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.
  • 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.
  • When a real person, a real human being whom others trust, says “This is good,” it has an effect that no brand, no ad, no faceless institution can match.
  • Most endorsements are organic, accidental even. The question is: How do we draw influencers to our work and increase our chances of it happening to us? How do we increase the odds for these accidents?
  • The first step is the hardest: making something really awesome that exceeds the expectations even of busy, important people with exacting taste.
  • There is no fiercer battle for attention than here, with influencers (and no one with higher standards).
  • 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.
  • One of the best ways I found to connect with people was very simple: I’d notice who was already wearing our clothes or wearing similar products. I’d email them to say hello and invite them to the factory and give them personal tours (something other companies couldn’t do). I’d send them nice emails and free products.
  • Think relationship first, transaction second.
  • I’ve always found that a critical part of attracting influencers is to look for the people who aren’t besieged by requests.
  • In my experience, the most effective use of influencer attention is not simply in driving people to check you out, but instead as a display of social proof.
  • Social proof sells. The perennial seller acquires it by being legit, and then comes up with interesting ways to use it to their advantage.
  • In my experience, almost everyone— from brands to artists— overestimates the value of traditional PR.
  • The question is whether press is usually an effect of a really good and popular thing or the cause of its goodness or popularity.
  • While the media might not necessarily convince customers, it definitely helps with recruiting investors and employees and impressing other important gatekeepers.
  • Still, this signaling is worth only so much— and it’s rarely worth more than other, more effective marketing techniques like discounting or personalized outreach.

OK, I Still Want to Get Press

  • If you are going to pursue a press-centric strategy, please listen to my advice on this: Start small.
  • Instead, you will have more success with PR if you treat it the same way you treated your product design: Identify your core audience and start there.
  • In this way, the modern media is really a seller’s market. Reporters want stuff.
  • 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. (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.
  • 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.”
  • I’ve bought quite a lot of it over the years (at least $20 million worth on behalf of clients), but as an effective tool for the launch of a product, advertising almost never works. It’s far more effective when there is already a considerable audience or sales track record.
  • 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).
  • The other reason that advertising isn’t an option for a lot of projects is that the real data required to answer the above questions is rarely available when launching something new.
  • When you do something unexpected or surprising, it almost always does better than going dollar for dollar against advertisers, who spend millions of dollars a year like it’s nothing
  • Creative advertising is probably the least competitive sector of advertising, because most brands either aren’t creative or are afraid to be.
  • The fact is, humor and levity will probably do more for your brand over the long term than trying to beat people over the head with brilliantly effective advertising copy. So if you are going to advertise— if you have determined that it is wiser to spend a dollar there than on anything else you might do— then at least make sure you have a good time and that your audience has one too.
  • It is true for marketing, just as it is for life. Principles are better than instructions and “hacks.”
  • When it comes to creating a perennial seller, the principle to never lose sight of is simple: Create word of mouth.
  • The best strategy is to try everything and see what works for your project— because it’s going to be different for every single project. When you find something, stick with it.
  • Marketing is the art of allocating resources— sending more power to the wheels that are getting traction, sending it away from the ones that are spinning. And investing in each strategy until the results stop working. Then find the next one!

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

  • In my definition, a platform is the combination of the tools, relationships, access, and audience that you have to bring to bear on spreading your creative work— not just once, but over the course of a career.
  • The ability to access and draw on our assets— whether they are social media or an email list or a phone call to a loyal ally or simply a popular body of work— is what makes an artist successful over the long term.
  • list, and it shouldn’t take the threat of being frozen out to get one started. Ideally, an email list is something you build up over the years, comprised of real, hard-core fans who know the real story about you and are never going to abandon you as long as what you make continues to be good. Right now, as of this writing, it’s the single most important and effective way to communicate with your potential audience and customers.

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.)

There is a second kind of “list” that matters just as much as the list I’ve been describing: your list of contacts, relationships, and influencers. Build success by building your network:

Some of Tim’s strategies:

  • 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 known but should be and will be.
  • Networking is not going to networking events and handing out business cards— that’s flyering. It is instead about forming, developing, and maintaining real relationships. It’s about being valuable and being available so that one day the favor might be returned.
  • Relationships Are a Platform Too
  • Developing the right relationships with the right people is the long game. This is how legacies are made and preserved.
  • If you see your career and your relationships as investments— if you give and help and build long before you ever need anything, if you continue doing great work over the long term— you’ll find that sometimes you won’t even need to ask for support.
  • The Most Important Relationship
  • While relationships with the “in crowd” matter and they help create an enduring career, nothing you build will last very long without the most important relationship of all: the one you have with your fans.

Build a Body of Work:

  • More great work is the best way to market yourself.
  • In fact, creating more work is one of the most effective marketing techniques of all.
  • The best way to become an author is to write more books, just as a true entrepreneur starts more than one business.
  • Very few of us can afford to abandon our gift after our first attempt, convinced that our legacy is secured.* Nor should we. We should prove to the world and to ourselves that we can do it again . . . and again.

Reach Out to New Fans

  • One of the things all creatives must do during their downtime is explore new ways of reaching new fans.
  • Choose never to become so settled into a rut or routine or type that you are constrained by it.
  • Everyone should know who their detractors are and rile them up every once in a while just for fun.

Build an Empire:

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.)
  • 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?
  • (You never know what can happen.)
  • 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 the parts of the experience or community surrounding my work that I can improve or grow?
  • (Live events, conferences, memberships, personalized products, etc.)
  • Most important, the great fear that this will somehow be a distraction or will take away from his production has not come to pass. Nor is it the case for the most successful multidisciplinary creators.

One Last Thing

  • 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.
  • So don’t wait. Build your platform now. Build it before your first great perennial seller comes out, so that you have a better chance of actually turning it into one.

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

  • In the first half, we focused on the standards for our products and projects. Making sure that we made something that put us within striking distance of the top— something close to the best in class for our field. We checked and rechecked and prepared ourselves.
  • The second half was about actually attempting that trip to the summit. It was about making our best effort on the ascent, knowing that there are no guarantees. Knowing that we’ll need the right weather conditions and timely breaks to make it. How long it takes, how far we might get remains to be seen. But we’re going to try— because that’s who we are. This is what we do.
  • “It feels nice for a moment, then surreal, then back to work.” - Craig Newmark (on knowing that he created something to be used by millions of people, that was going strong after twenty years)

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