Snow Leopard
Snow Leopard

Snow Leopard

Legendary writers, the ones who stand the test of time, create a category of one. (Location 33)

Regular leopards, the ones with golden fur and black spots, spend their entire lives competing against each other. They look the same. They act the same. They move in groups. They seek acceptance. The snow leopard does none of these things. In fact, it’s rare to see even two snow leopards together. Ever. (Location 34)

Unfortunately, as we wrote about in The “Me” Disease, the vast majority of people who want to be a “thought leader” or best-selling author in today’s digital, gamified world don’t have any leading thoughts. That is to say: they are not actually contributing new, differentiated ideas. (Location 50)

They want the outcome without the process. And since this has become such a desirable goal, there are now strategies for shortcutting your way to instant “status” gratification. (Location 56)

Which is why the most viral content caters to lowest common denominator emotions: rage, joy, wonder, sadness, shock, surprise, desire, and so on. (Location 64)

As a result, most people do not define “being a thought leader” as having something unique and different to say. The way the world defines a “thought leader” (especially the digital world) is by measures of public approval. (Location 65)

Out of nowhere, they start posting BGOs (Blinding Glimpses of the Obvious) because this sort of non-threatening content is the easiest way to get Likes and climb the perceived ladder of success without ruffling any feathers. (Location 70)

For those who don’t want to cater to the lowest common denominator, but still don’t have anything valuable to say, the other strategy is to add complexity to sound “smart.” (Location 75)

The truth is, ideas like these are easy to understand but hard to execute. And since simplicity doesn’t sell services, many academics and consultants complicate the language to make a simple idea feel like rocket science to justify their fees to come in and do the work. (Location 84)

In order to be a “thought leader,” you must be willing to LEAD WITH YOUR THOUGHTS. (Location 88)

This means it is your responsibility to say things people have not said yet. It is your responsibility to take risks, challenge conventional wisdom, and (dare we say) allow yourself to be creative—not in the art school “I’m-creative-just-like-you” way, but in the Elon Musk “I’m-going-to-Mars-F-U” sort of way. (Location 89)

It’s about taking the world somewhere new because you are already living in the future. And you’re on a mission to get everyone else there with you. (Location 92)

Unfortunately, most people who aspire to be a “thought leader” (by any definition of the term) struggle to make it past Levels 2 or 3 on The Content Pyramid. They mistake passionately sharing someone else’s ideas, or stating a “Blinding Glimpse of the Obvious,” for thought leadership. (Location 100)

So before you even start “playing the game” of writing and leading with your thoughts, you need to make a decision. (Location 126)

“Different” things don’t get accepted right away. Meaningful things take time to understand. And Non-Obvious connections require people to think—and guess what? Most people scrolling through social media don’t want to think. (Location 127)

If you want to be accepted, if you want lots of followers and engagement and badges that say you’re awesome (in the short term), then Tweet, post, and make videos catering to the lowest common denominator. (Location 129)

The problem is: the whole world might not be interested in what you’ve made. Let’s say you sat down and decided to write an essay about the importance of owning a farm of chickens. (Location 141)

The reason so many aspiring thought leaders create Obvious, non-threatening content is because their goal isn’t actually to “lead thoughts” in a different direction. Their goal is to increase the number next to their profile picture that says how many people on planet earth think they’re awesome—so they can use that number to book speaking gigs, sell products, or just fall asleep a little bit easier at night knowing they’re “Liked” online. (Location 150)

as a rule of thumb: people with giant audiences online tend to create the most surface-level, Obvious, content-free content. (Location 154)

This is a bit like what happens as a consumer when you move from Passive to Active consumption. You understand that all content is a trade. (Location 182)

Most people do not begin their journey as a writer, creator, or industry thought leader by creating original content. (Location 189)

Instead, they begin by imitating and curating thoughts, perspectives, insights, and ideas from people they admire. (Location 190)

In fact, some people stay at Level 2 their entire lives, mastering the art of curating other people’s ideas and never climbing further up The Content Pyramid. (Location 195)

Next is level of curation is adding your own opinion. You share something AND you tell the reader why you like it, don’t like, feel happy or sad or upset or inspired by it. Communicating your own opinion on the content you are sharing makes you a creator. (Location 208)

Above that is curation with insight. Opinions are easy—everyone has one. But what’s much more valuable than an opinion is an insight. This is what makes Ryan Holiday, Tim Ferriss, and other world-class curators so effective. (Location 210)

Whether you are curating other people’s thoughts, insights, stories, and perspectives, or creating your own, the end result can be organized in two overarching mega categories. (Location 216)

Gary Vaynerchuk creates Obvious Connections for his audience. His content is very linear and easy to understand. “You want to learn how to do content on social media? Here’s how to create content on social media.” A to B. One to two. Straight line. (Location 218)

Nassim Nicholas Taleb creates Non-Obvious Connections for his audience. His content is not linear. It’s abstract, and requires drawing connections between seemingly unrelated data points. (Location 219)

Obvious Connection content is simple by design. Its goal is less esoteric, more actionable, and engineered to move readers incrementally forward in some meaningful way. To be clear: there is nothing wrong with this. Some of our favorite books, podcasts, and YouTube channels create absolutely terrific Obvious Connection content. (Location 228)

Non-Obvious Connections stand the test of time. They matter now and way in the future. “This changed my life.” More importantly, most Non-Obvious Connections tend to gain in value over time as more and more people “get” it. (Location 233)

Think of this as Demand Capture vs Demand Creation. When you are drawing an Obvious Connection, the person already understands what you’re talking about—and all you’re doing is moving them forward. (Location 236)

From a thought leadership perspective, if your goal is to get attention and money quickly, it’s typically much easier to do so by incrementally moving someone forward three steps opposed to picking them up and planting them in a new universe. (Location 241)

Non-Obvious Connections require them to think—and remember, most people don’t want to “think.” (Location 243)

So, the pro of creating Obvious Connections for your readers is more immediate, and dare we say more “guaranteed” acceptance and approval. (Location 245)

The con of creating Obvious Connections for your reader is that, without some intentional category design & languaging, you are most likely just a slightly better version of the person (or company) who came before you, and there’s almost nothing about what you’re creating that is defensible against the person who comes after you. (Location 247)

(There actually isn’t a right or wrong answer to this question. It’s just worth pointing out how many people say they want the latter, but manically refresh their social media metrics and sales data clearly obsessed with the former.) (Location 261)

Non-Obvious Connectors are writers, creators, entrepreneurs, and thought leaders who change the world with their thinking. The unfortunate part, however, is that data shows us most people don’t want their thinking changed. (Location 263)

It took more than a century for Copernicus’ Non-Obvious Connection that the earth revolves around the sun, not the other way around, to become widely accepted. (Location 272)

He picks a topic, and then curates juxtaposing and surprising stories that, when held together, allow the reader to draw Non-Obvious Connections. (Location 281)

Talking to Strangers is a challenging and controversial excursion through history, psychology, and scandals taken straight from the news. (Location 286)

Again, it’s worth noting that while Non-Obvious Connections tend to have longer shelf lives, they also tend to sell less (and attract significantly less attention) than their Obvious counterparts. (Location 301)

The top of The Content Pyramid is Category Creation. Both Obvious Connectors and Non-Obvious Connectors can achieve the top of the pyramid. Even curators (like Ryan Holiday or Tim Ferriss) can achieve the top of the pyramid. (Location 307)

When you are first starting out as a writer, creator, or aspiring “thought leader,” you think your goal is to hit a home run. You want to write a best-selling book. You want to go viral. You want to win an award. (Location 313)

Your goal isn’t to write one great book—your goal is to write dozens, if not hundreds of great books. And your goal isn’t to create one viral video— your goal is to create hundreds, maybe thousands of viral videos. (Location 316)

What readers, listeners, viewers, and potential customers want isn’t you. It’s your category. The reason readers keep buying more Ryan Holiday books is because he keeps writing books about Stoicism, and his readers are obsessed with [category] Stoicism. (Location 336)

When you successfully build a unique and differentiated category (in which the reader is the Main Character, not you), you can create a dozen different revenue streams giving readers more of what they love [category] in a dozen different ways. (Location 339)

In fact, the more differentiated your category, and the more committed you are to giving readers more of what they want in that chosen category, the more likely you are to see the next business model opportunity hiding in plain sight. (Location 344)

Making money as a writer, creator, entrepreneur and thought leader is easy when you are known for a niche you own. (Location 348)

Climbing The Content Pyramid is not easy. Just like how running 26.2 miles (a marathon) isn’t easy. It hurts your legs. It makes you gasp for air. You end up in a puddle of sweat. You stink. And you’re exhausted for a few days. (Location 351)

Writing, creating content, and “leading people’s thinking in new and different directions” is no different. It’s hard. It takes work. (Location 355)

We Pirates hope to do this until we die. We are addicted to Thinker’s High. Every time we experience it, we want it to last longer. And when it goes away, we want to do it again (despite the fact that our heads hurt after it wears off). As both a creator and a consumer, “Thinker’s High” is your measure for success. (Location 359)

Once you have total clarity around your monthly spending, now consider how much money you have in savings/liquid investments and how many months you would be able to sustain your current style of living if your income was reduced to $0. (Location 384)

The reality is, most people make financial decisions based on what they want other people to think about them—opposed to what they truly want for themselves. (Location 407)

Your “ultimate goal” is not to make money as a writer or creator. It’s also not to make “a lot” of money as a writer or creator. (Location 413)

(This is sometimes called “horizontal income” because it rolls into your bank account even when you’re laying down.) These creations (assets) could be directly related to your craft: books and courses, eBooks and paid newsletters, etc. Or these assets could be indirectly related and purchased from the earnings generated from your craft: stocks and bonds, real estate, cryptocurrencies, and so on. (Location 416)

The point is: what you want is to create and/or acquire assets that pay you dividends regardless of whether or not you show up to the office. (Location 418)

how much does your party cost? If you make $1 million but spend $1 million on “your party,” you are “making a lot of money” and still poor. But if you make $1 million but only spend $100,000 and use the other $900,000 to build, buy, or invest in assets that will pay you forever, you’ve just gained 9+ years of runway. (Location 426)

The point is, these writers have a financial goal above all things, and make decisions accordingly. (Location 457)

[Money] If you are an Obvious creator making Obvious Connections in your content, then you are more likely to make money in the short-term. (Location 483)

Obvious content is incremental (“How to move from A to B”), immediate, urgent, and can usually be rationalized (Location 484)

Non-Obvious creators usually don’t become best-sellers overnight. They are way less viral. In fact, some of the best Non-Obvious creators became famous after their death. (Location 511)

A perfect example of this is the “money” difference between these two books: The Subtle Art of Not Giving A F*ck and Thinking, Fast and Slow. (Location 514)

If you want to make money NOW, write an Obvious book like The Subtle Art of Not Giving A F*ck (the book’s big idea is: if you want to be happy, just don’t give a fuck). But if you don’t want to optimize for (near-term) money, and would rather optimize for Time, Impact, Legacy, and/or Contribution to society, write a Non-Obvious book like Thinking, Fast and Slow (which articulates in great detail the two modes of thinking human beings juggle as we make our way through life). (Location 519)

Like a fine wine, Non-Obvious creators benefit the most from time. Their work becomes more and more true, more and more relevant, and over a long enough horizon, becomes representative of an entire decade or even generation of humanity. (Location 528)

The vast majority of writers, creators, and thought leaders say they want to “stand the test of time” or “have a legendary impact,” but then 2 seconds later point to some Obvious creator going viral on social media making a bunch of money (in the short term) (Location 549)

For example: it’s hard to solve your burn rate in the short term by creating Non-Obvious content. Because Non-Obvious content rarely makes (much) money in the short term, and all of the upside tends to come 5-10 years later (if your Non-Obvious content is successful at introducing new thinking and moving the world). (Location 561)

between—it’s important to understand what the “trade” is you’re offering the reader and customer. And the trade goes like this: if a reader is going to give you their attention and/or money, what they’re really giving you is time off their life. (Location 573)

What you’re really asking for is a chunk of their life. Because they’ll never get those 2 minutes, or 20 minutes, or 2 hours, or 20 hours back again. Ever. (Location 576)

What is the “value” of your content? What’s the “give-to-get?” What is the consumer giving (time, or time & money), and what do they expect to get in return? (Location 579)

The answer is almost always one of two extremes: either you are offering them something Obvious, cheap, easy-to-understand and consume (McDonald’s), or you’re offering them something Non-Obvious, expensive, and difficult-to-understand and consume that leaves them “wanting more” (a Michelin Star restaurant). (Location 580)

If you ever find yourself rationalizing the “value” of the thing you’ve created, convincing yourself that it’s “for everyone,” that’s a neon sign you’re using ill-constructed mental scaffolding. (Location 607)

Most writers spend their entire lives thinking the key to becoming a legendary writer is to read. And yes, while there is tremendous benefit to “studying the greats” and exposing yourself to a wide variety of perspectives and writing styles, the brutal truth is that most aspiring writers who read “a lot” end up mastering the craft of reading and never write a single thing. (Location 619)

Think of the knowledge you acquire through Active Consumption as potential energy. (Location 630)

The primary value a Curator provides is saving time. They’re McDonald’s. (Although, in rare exceptions, some Curators deserve a Michelin Star.) (Location 636)

What you’re trading is your attention in exchange for their organization and judgment. Instead of having to sift through hundreds or even thousands of articles, podcast episodes, YouTube videos, etc., on a given subject, you are “paying” someone else to do that hard work for you. (Location 643)

As a Superconsumer of a given subject or industry, you inherently understand what is worth “paying attention to” more than the average person. (Location 662)

Curate books people should read based on specialty. Curate books people can read in different time frames (quick reads vs beach reads vs year-long reads). Curate books by “price per page,” and share which ones are worth the time. Curate books by impact on the business world. (Location 670)

What makes curation valuable is the urgency, specificity, and importance of what is being curated. (Location 680)

The problem is, it’s hard for Curators to unlock new business models for themselves (such as charging for their unique insights) because their entire value (the “trade”) is based on their ability to organize content— not their expertise, perspectives, stories, original frameworks, and so on. The benefit you deliver is convenience, not wisdom. (Location 695)

Conventional wisdom in the digital, social world says to “build an audience, first” and then decide what you want to do with it later. The problem is, not all audiences are created equal. (Location 711)

The transition from Curator to Creator happens when you spend more time sharing your own expertise than you do other people’s. (Location 735)

Most importantly, leveraging a Direct-To-Creator business model is what elevates you out of “transactional business models.” (Location 749)

And you know you want your business model to be Direct-To-Creator—straight from the customer’s pocket into your pocket. (Location 755)

Non-Obvious content is Thinking. It’s the reason “Why” something works, happens, functions, etc. “Why” content is Non-Obvious and meandering because understanding requires context and the connection of disparate and oftentimes conflicting or polar opposite data points. (Location 765)

Obvious creators don’t have to risk being wrong (or being “exponentially wrong”), because Obvious content speaks to Obvious, commonly understood, and already desirable answers and outcomes. For example: “How To Write A Book.” The writer already knows the audience wants to write a book, and their job is to move them incrementally forward (from A to B) in order to unlock that already desirable outcome. (Location 769)

Non-Obvious creators, on the other hand, have to have the guts to stand in the middle of the town square with egg on their face. When you are a Non-Obvious creator, your content is working to provide answers that are not already commonly understood, (and in some cases: first educate people about problems that are not already commonly understood, before giving them answers to those problems that are not already commonly understood). (Location 772)

Again, most people want to believe they have what it takes to be a Non-Obvious Creator, and maybe functionally they do. But it’s the emotional side, the fear of being publicly rebuked, questioned, criticized, or simply wrong (and shamed as a result) that holds them back. (Location 778)

This content is the easiest to monetize because the reader/customer already knows what they want—and as long as you speak to what the reader/customer already knows they want, and can prove competence and credibility, it’s fairly likely they will buy what you’re selling. (Location 785)

Whether you write a book, or create a course, or put together a keynote speech, or hold monthly mastermind sessions, bookcamps, or workshops is sort of irrelevant. They’re all potential vehicles and they all work (some writers make a lot of money writing books, others make a lot of money selling courses, etc.). When in doubt, we are biased toward choosing digital vehicles over analog vehicles given their ability to scale on the Internet, but it’s up to you. (Location 803)

If you want to make money, achieve credibility, and advance your career in the short term, Obvious content is the place to start. However (going back to our “How much does the party cost?” and “Who is the party for?” questions), if creating Obvious content starts to make you money, and you get used to that newfound credibility and status, and you increase your style of living (you made it!) and burn rate as a result, it will become harder and harder to get off the Obvious content hamster wheel, transition, and rise to the next level of The Content Pyramid. (Location 828)

You’re stuck. You need to keep making money because you need to sustain your lifestyle so you create more and more Obvious content—and round and round you go. (Location 832)

But the likelihood this approach leads to any of them becoming a category-leading author with a library that compounds in value is very, very low. (Location 836)

Both Obvious and Non-Obvious creators can build tremendous careers for themselves. But the big difference between the two comes down to pricing power—and the older you get, the more important this becomes (because your time becomes more precious, which means you want to be able to charge more for your limited time). (Location 852)

The difference is that Obvious creators provide products and services. Whereas Non-Obvious creators provide experiences and transformations. And the more valuable the transformation, the more your expertise and insight is valued. (Location 854)

In fact, we find it’s more common for Non-Obvious creators to start out as Non-Obvious creators and never bother with Obvious creation at all. They would rather “do their own thing” and wait ten or twenty years (or even their entire lifetime!) for the world to “get” what they believe matters most—than waste time playing the Obvious game for money, status, and short-term impact. (Location 856)

What is interesting, however, is that Non-Obvious creators can also experience massive money and status outcomes, they are just usually delayed. (Location 862)

When you choose to defer responsibility over the “business” side of your work, particularly when you sign a book deal with a major publisher, (Location 875)

If the “trap” for Obvious creators is making money and achieving status in the short term, and then getting “hooked” on that money/ status and remaining on the Obvious content hamster wheel forever, then the “trap” for Non-Obvious creators is trying to capture money and status in the short term for their Non-Obvious work (by signing with a publishing company for an advance to “live on”) but giving up 90% of their long-term upside. (Location 880)

When first starting out, they need money to live on “now,” but don’t want to learn how to use Obvious creation to make that happen for themselves (to fund and fuel their Non-Obvious work), so they sell ownership in their Non-Obvious work long before its value has been realized. (Location 884)

In addition, Non-Obvious Creator business models are still DirectTo-Creator, but the portfolio leans less on products (books, courses, etc.) and services (speaking, consulting, advising, etc.), and more on experiences (super premium guru consulting & community-driven courses) and transformations (outcome-based services, digital products, books, advising, etc.). (Location 887)

Q&A consulting is when the questions that are asked are the same questions asked by different people. “How do I cut my costs? How do I market to my customers?” This becomes fairly straightforward with enough experience and can be a great (Obvious) way to monetize, (Location 891)

This is the type of consulting most Obvious content creators do. “My 5-how-to-steps” are like everyone else’s 5-how-to-steps. (Location 894)

Guru consulting is when your Non-Obvious content is unique and you are known as the only person in the world who can answer that question. Gurus tend to be quirky and part of the benefit is the experience and entertainment that comes with working with them. (Location 895)

Outcome-based consulting is when guarantee an outcome (or guarantee you’ll get pretty close). That’s 7-figure stuff—either cash or equity or both. In addition, there is oftentimes actual scarcity, but at a minimum there must be the perception of scarcity. (Location 899)

Since Non-Obvious Creators inherently have less volume (fewer shots on goal), by definition they have to charge higher prices for their limited time and volume. (Location 902)

His Non-Obvious business case was so powerful that the opposition dropped the lawsuit before Pirate Eddie even had his deposition training. (Translation: Non-Obvious thinkers can earn exponential money when the world “gets” the value of their unique intellectual capital.) (Location 911)

This is when the consultant is almost guaranteeing a certain outcome from the Non-Obvious content and the Obvious or Non-Obvious actions that get executed as a result. Outcomes can be things like “you’ll save 20-30% of your procurement cost,” (Location 914)

The point is: as a Non-Obvious writer and creator, you will always make the most money when you find ways to monetize the experience, outcome, or transformation and not just “the information.” (Location 920)

It’s a business that educates writers and gives them Obvious frameworks to solve Obvious problems they’re experiencing in their lives—everything from overcoming imposter syndrome and procrastination, learning how to start writing on Twitter and LinkedIn, and so on. It is unique. It is differentiated. But at its core, it is Obvious. (Location 933)

Whereas this book, and just about everything we publish here at Category Pirates, is Non-Obvious. (Location 937)

It would be foolish to think this Non-Obvious book would grow faster and generate more money, social media attention & status, and short-term impact than something like Ship 30 for 30—because Non-Obvious content doesn’t do that. (Location 938)

What most people don’t know, however, is that 99% of the insight and information in Play Bigger is the same insight Pirate Christopher gets paid (in cash and equity) by startups to explain individually to them—helping (Location 952)

Same information, same insight and knowledge, different business model. Pirate Christopher doesn’t need millions and millions of entrepreneurs buying his knowledge for $30. (Location 955)

What most people don’t realize is that almost all of the information that is in Pirate Cole’s $20 book is much of the same information he shares in all of the other ways he monetizes—except with more access. (Location 968)

To increase the “value of your value,” the key is to make access to you and your specialized knowledge more private and personal. (Location 973)

They feel closer to you, and get a different level of experience as a result. (Location 976)

This means you have successfully become known for a niche you own, and that niche has a tailwind behind it (that you have either created or accelerated) that will last long enough for you to exceed your “burn rate,” save and invest money, create and buy assets that pay you dividends long into the future, have a meaningful impact on the world, achieve a level of status that ensures new opportunities continue to fall into your lap, and allow you to do what you love every single day until the day your life comes to an end. (Location 982)

(Ryan’s first several books were on completely different topics. But when his “Stoicism” work started to tip, he went all in and continued writing about Stoicism until he eventually became known for this niche—which he now owns.) (Location 1000)

If and when it becomes crystal clear (as a result of your work, your contributions to the category, and your consistent output over a long period of time) what 1-2-3-4 words summarize your category, and 100 out of 100 people all say those same exact words when describing you, you win. (Location 1001)

In layman’s terms, this means that when you are the Category King (of any category or niche, big or small), you are the one who benefits the most from that category’s growth. (Location 1008)

You don’t have to worry about being “knocked off.” (The more people try to knock you off, the more they reinforce your Category King position!) (Location 1032)

The fact that you don’t know (and we don’t know) is a bigger problem than most writers and creators realize. You see, it’s amazing to be a legendary writer and Obvious or Non-Obvious creator, but what separates Category Creators is the languaging they’ve attached to their category. (Location 1039)

But “content marketing” is broad, and includes everything from creation to distribution to content management. (Location 1064)

More importantly, how much of the content being created (especially by enterprise companies and B2C companies) is actually worth reading? (Location 1069)

The “content management” subcategory of the mega content marketing category is growing faster than ever—and yet, according to Content Hacker, the #1 activity B2B companies outsource is content creation (by a mile). 86% of B2B organizations surveyed said they outsourced content creation. (Location 1072)

As we wrote about in our mini-book, The “Me” Disease, many marketers today have (unfortunately) caught Gary Vee-D, a “content disease” that leads creators and companies alike to believe the whole purpose of content creation is to “do it”—and to do it as often as possible. (Location 1080)

Reach & Frequency means “the more people (reach) who see my brand, more often (frequency), the better off we’ll be.” No, these advertising legends were successful because they owned a specific position in the customer’s mind (a category). (Location 1096)

The other 9 steps are about the amplification of the content (which means, if you don’t have a differentiated POV to begin with, what are the other 9 steps even in service of? More for more’s sake?). (Location 1135)

The business world has unknowingly created this Content Marketing Industrial Complex because “such a complex is said to pursue its own financial interests regardless of, and often at the expense of, the best interests of society and individuals.” (Location 1142)

When content marketers do this, they teach readers, listeners, viewers, and potential customers (and investors) to stop paying attention to them. The customers you care about (your Superconsumers) aren’t stupid, and they know regurgitations when they hear them. (Location 1166)

Lastly, content-free marketing leads to easier, faster, cheaper output. Output is noticeable. Output makes it look like the marketing department is doing something. (Location 1169)

Less resources for creating quality content (and/or increased outsourcing of content creation) leads to more content-free marketing. (How did the solution to the problem “our content marketing results are not great” become MORE CONTENT!?) (Location 1174)

If you are a founder, executive, investor, or small business owner and you’ve ever hired an SEO firm, a PR firm, or a social media agency, how good are they at coming up with compelling ideas? Most are not. Their job is basically to create content-free content and pump it into algorithms, spam email it to journalists, and pitch it anywhere and everywhere they can—with the hopes of getting a backlink or two to the other content-free content on your website. (Location 1179)

The book, and the coinciding strategy, is to quite literally pretend to “provide value” a few times before hitting the reader, viewer, or listener with (Location 1187)

If it’s not legendary, why are you doing it? (As soon as you change the mindset from “legendary volume” to “legendary content,” you will stand out.) (Location 1209)

Newsflash: what *time of day* you post your content is IRRELEVANT (ARRRRRR!!!!!!!) if what you’re posting is content-free. (Location 1237)

There is a cataclysmic-sized gap between these two examples. The first one is focused on me, me, me, and the second is focused on YOU, YOU, YOU. (Location 1257)

The problem here is that individuals and companies who have achieved nearly any level of success in their careers begin to drink their own rum and assume everyone should pay attention to them because of what they’ve achieved. (Location 1269)

We know the CEO of a major publicly traded tech company who wanted to start a weekly podcast but was stopped by their legal department and board for fear this CEO might say, “The wrong thing.” (Location 1286)

And the reason we believe this has become such a commonly accepted “strategy” for companies and their executives is because spewing undifferentiated thinking across 27 different platforms, costly as it might be, is the only way for a company to say *anything* without flagging HR, legal, the board, and a room full of executives. (Location 1301)

It’s about how many people are moved by your content enough to *share* it. (Location 1306)

Views, Likes, and follows are vanity metrics. Anyone can get views. The three of us Pirates watch stuff all the time we don’t really care about. It hooks our attention for a fleeting moment, and then it’s gone and we think nothing of it (videos of cats and raging Karens inside Wal-Mart come to mind). (Location 1310)

Your content should be so radically differentiated (aka: provide such new, valuable, differentiated THINKING) that you get emails from worried Supers saying, “Ummm, hi? Just checking in here. It’s been two weeks since you posted anything and I’m starting to go through withdrawals. Any update on when the next piece of content is dropping?” (Location 1321)

Somewhere along the way, marketing folks internalized the faulty belief that people owed them their attention. (Location 1328)

What’s hard is actually sitting there and thinking about the premise of the conversation being had in your category. Do you agree or disagree with the conventional wisdom? How come? And how did you arrive at your conclusion? Is this conclusion new and different in any way? If not, start over and try again. (Location 1342)

If you are “thinking” in the same direction as everyone else, you’re noise. You’re an inconvenient scroll. And yet, going back to how we started this chapter: 86% of B2B organizations surveyed said they outsource content creation. (Location 1346)

Right now, the “idea” portion of the content marketing supply chain, the nucleus, the “thinking,” has at most 10% priority. (Location 1359)

In fact, we would argue that most large-scale companies would be 100x better off reducing the person-power of their content marketing departments by 50-90% and reallocating those resources to publishing higher quality, more differentiated content less often. (Location 1362)

If you are a half-decent writer, mediocre marketer, but a courageous thinker, you can make a boatload (ARRRRRRRR!!!!) of money helping Content Marketing Industrial Complexes find their soul again. (Location 1391)

For example, Pirate Cole has built a legendary career working with startup founders, company executives, and investors on refining their thinking and publishing their unique insights at scale on the Internet (and there’s a reason Pirate Cole is 100x+ more expensive than the “ghostwriters” you find on (Location 1394)

Almost all thinking is reflexive (having an unconscious “reflex” in response) versus what Roger calls “reflective” (taking a moment to consciously reflect on how the past may have created a preexisting mental model keeping you from considering a new and different future). (Location 1415)

You become conscious of which model you are using to evaluate the information (which “lens” you are looking through). And then before you react, respond, or give in to your reflexive nature, you pause and first consider which mental model you’re using to examine the information being presented. You train yourself to be curious, to ask why, to suspend your past opinions, beliefs, and mental models, and to open the aperture of your mind and consider something different. (Location 1422)

The vast majority of conventional wisdom and strategy is thinking “what has been true” about the past. (Location 1430)

The vast majority of content about strategic thinking comes from academia and strategy consulting firms. (Location 1437)

Academia takes it one step further. Academics can’t publish without extensive research about the past. And any new information has to be rigorously peer reviewed by other professors who are experts about the past. (Location 1440)

For example: in 2008, the idea of Airbnb made no sense when evaluated through old mental models. As a result, nearly every venture capitalist said, “No way. You can’t rent out your living room as if it’s a hotel. That’s insane. Probably illegal. (Location 1447)

Most people (whether they realize it or not) are trapped in backward-looking reflexive thinking. (Location 1456)

Some of the “smartest” people on planet earth lose this thread. Some of the smartest people stopped reflective thinking a long time ago. We would even go so far as to say that being declared a smart person is almost certain to make you stupid. (Location 1461)

It’s crucial to understand which of these two consumption states you are creating for, and where you are “meeting the reader”—long before you write even a single word. Because if you try feeding Non-Obvious content (that requires reflection and a challenging of one’s own mental models) to someone in an Obvious (reflexive) state, you will fail to get their attention and/or they’ll likely become frustrated at your inability to cater to their preconceived notions. (Location 1472)

Reflexive readers want Obvious content. Reflective readers want Non-Obvious content. Knowing who you are creating for, and what their expectations are (and why) is half the battle to becoming a legendary writer, creator, and/ or entrepreneur. (Location 1477)

Both are meaningful and valuable to different types of consumers at different levels of learning. (There is a time and a place to play Chopin. And there is a time and place to play chopsticks.) (Location 1486)

But as you’ll soon discover, the art (and business) of becoming a legendary writer, creator, or entrepreneur is about finding strategic ways to move up and out of Obvious, incremental instruction and into exponential Non-Obvious thinking. (Location 1487)

The reader or customer doesn’t care how many words you write or how much effort you put into crafting the idea. All they care about is the problem you are solving, the solution you are providing, and the outcome you are unlocking for them. (Location 1493)

Conventional wisdom here says that with this simple framework in mind, your job as a writer, creator, or entrepreneur is to figure out how to solve problems “better” than everyone else, or how to provide “better” solutions, or how to unlock “better” outcomes than the competition. (Location 1499)

But this is reflexive thinking (which means it’s a very bad strategy). Your job is not to look at other people’s ideas, give in to an emotional reflex (“I’m going to crush you!!!”), and try to create something “better.” Your job is to reflect on your own mental models, “think,” and introduce the world to ideas that are new, different, and fresh. (Location 1501)

As a writer or creator, what you really are is an “Intellectual Capitalist” whose job is to “think”—and (Location 1505)

On the other side of the spectrum (Non-Obvious, Non-Obvious), your thinking is so out-of-the-box, so ahead of its time, that people struggle to wrap their minds around it. It’s differentiated to an almost unusable degree. Which puts you in the camp of all the other writers, thinkers, and creators who believe themselves to be brilliant, but can’t quite figure out how to get everyone else to see it too. (Location 1512)

The secret is in the middle: to be Obvious in Non-Obvious ways, or to be Non-Obvious in Obvious ways. (Location 1515)

The reason is because without both, your ideas are either so rudimentary (Obvious) they’re commodities, or they’re so complicated or unexpected (Non-Obvious) they’re confusing—which is just a different flavor of stupid. And when people are confused, their reflexive brain tells them to dismiss the idea and just move on. (Location 1516)

With this in mind, the easiest way to immediately differentiate yourself as a writer, thinker, and creator is to take an Obvious problem, solve it in a Non-Obvious way, and unlock an Obvious, already desirable outcome. (Location 1563)

Obvious problem, Non-Obvious solution. And this is how Pirate Cole built a multimillion-dollar ghostwriting agency working with hundreds of founders, executives, and investors in less than 18 months. (Location 1572)

The key, however, is making Non-Obvious problems seem easy, simple, and “Obvious” to solve for. As we’ll get into in the next section, if you present a Non-Obvious solution to a Non-Obvious problem, the person on the other side of the table is going to have a hard time a) understanding the urgency and importance of the problem, and b) understanding the importance and the action steps of the solution. (Location 1594)

But when you educate a reader or customer about a Non-Obvious problem, and then give them an easy, simple, highly actionable Obvious solution, all of a sudden… POOF! Their life is changed forever. (Location 1597)

The short answer for how to make Obvious content seem NonObvious is by using languaging to niche down, Name & Claim an idea, and/or invent a new term. (It’s not word-of-mouth marketing. It’s The Tipping Point! It’s not “hire a cleaning service and a dog walker so you spend less time doing things you don’t enjoy and can easily outsource.” It’s 4-Hour Work Week!). (Location 1701)

That’s what makes them Non-Obvious. Which means you need to train your mind to hold opposing, seemingly unrelated ideas long enough for your mental model (as we talked about at the beginning) to consider, “What must be true?” (Location 1708)

Solutions create problems, and problems create categories. (Location 1724)

This means today’s solutions are going to create tomorrow’s problems, and solving tomorrow’s problems before anyone else is just another way of saying “solving Non-Obvious problems.” (Location 1726)

But today’s solutions create tomorrow’s problems, and as soon as you buy your first Bitcoin, all of a sudden you are confronted by a slew of new and different problems: (Location 1729)

What you are NOT doing is trying to “catch” a new wave or trend. In the Obvious world, this is what reflexive thinkers “think” is innovation: something popular happens, and your job is to see and create a new solution for the existing problem. (Location 1737)

We want you to create demand. Instead of having a reflexive reaction to today’s innovations, reflect for a bit and think, “What could be true?” Consider what new, Non-Obvious problems today’s solutions might create in the future—and go create them. (Location 1742)

The Non-Obvious solution was to use technology and a giant wave pool to create that perfect wave, forever. (Location 1753)

You are a Superconsumer: You are passionate about something, and so you understand your own problems better than anyone else. (Location 1757)

You are a Category Designer: You can frame solutions to problems people didn’t know they had. (Location 1758)

You are a Languager: You can use language to transform a rational problem into an emotional one by “calling” it something. (Location 1759)

You are a Visionary: You can visualize Non-Obvious outcomes few people believe are possible. (Location 1760)

You are a Missionary: You are already living in the future, and will excitedly knock on people’s doors in an effort to “spread the good word.” (Location 1761)

Each one of these archetypes has the potential to come up with Non-Obvious insights—all from different vantage points. And it’s very possible that you are a magical combination of any or all of the above—a pirate wearing multiple pirate hats! (Location 1762)

But when the idea comes out of the oven and the body of work is sitting on a dinner plate, none of us know (or can accurately remember) whose idea it was. Because it doesn’t matter. (Location 1777)

As a writer, creator, and thinker, one of your top priorities in life should be to surround yourself with other pirates and build a pirate ship of your own. (Location 1782)

You consume content about it. You consume content about the content. You spend all day, every day, thinking about this “thing” you love so much—and deep down, some part of you wishes more people existed in the world who would be willing to “nerd out” about it with you. (Location 1790)

So much so, that your reaction (unless you are a Super of that “thing” yourself) will likely be, “Wow, this person is weird.” But they’re not weird. They are insanely knowledgeable about something niche, specific, and likely full of untapped value. Which means your job is to listen, “think,” and consider what “must” be true. (Location 1794)

The Category Designer is terrific at recognizing (and “listening for”) Non-Obvious problems. And the Superconsumer is terrific at leveraging their domain expertise to be able to articulate and share Non-Obvious problems. (Location 1803)

Journalists, speechwriters, even lawyers tend to be terrific Languagers. They have mastered the fundamentals of the written word, and possess an incredible awareness for the ways in which words trigger different thoughts and emotions in readers. (Location 1809)

But pinpointing a Non-Obvious problem, and creating an Obvious solution (or vice versa), isn’t the end of the road. The last leg of the journey requires you to find a Visionary who can help you imagine what the future will look like once this Non-Obvious problem is solved. (Location 1823)

Visionaries live in the clouds—for good and bad. They can imagine Non-Obvious outcomes better than anyone, but have trouble keeping their feet on the ground long enough to turn their daydreams into reality. Which is why the effectiveness of a Visionary is multiplied when she or he is surrounded by other more grounded pirates. (Location 1828)

90% of what we’ve been taught about entrepreneurship, business strategy, and marketing is wrong. (Location 1851)

Entrepreneurship advice like, “You want to find product-market fit,” and other business strategies rooted in conventional wisdom start with the way “it is.” For example, “disruption” is tied to “the way it is.” (Location 1858)

The beginning of Picasso’s career was spent, to put it bluntly, in Vincent Van Gogh’s shadow. (Location 1864)

In an analogy, this is how most writers, creators, and entrepreneurs think about product creation, innovation, digital transformation, and marketing. They start with “what exists,” and then aim to “disrupt” or “change” or “transform” the way it is. They assume the market. They say, “Impressionism is what people clearly want. So let’s do impressionism, but better.” (Location 1872)

angles,” Picasso was still playing by the rules someone else wrote. He might have been executing the rules a bit differently, or with his own “style,” but when the painting was hung to dry, it was still, by every definition, an “impressionist” (category) painting. (Location 1878)

Assuming the market isn’t what made Picasso, Picasso. (Location 1889)

Instead, the reason Picasso is one of the most well-known and highly valued artists of all time is because he stopped trying to create the future while simultaneously remaining rooted in the past. Said differently, he “quit” the game of Impressionism and he “created” a new game called Cubism. (Location 1892)

More importantly, what allowed Picasso to create a new category of art wasn’t just that he called it something different (although the languaging “Cubism” certainly helped it stick). It was that he also changed the way he defined success—that is to say, he introduced a new Point Of View of what he believed a painting should be. (Location 1897)

Instead of depicting objects from a single viewpoint, the artist depicts the subject from a multitude of viewpoints to represent the subject in a greater context. Objects are analyzed, broken up, and reassembled to an abstracted form. (Location 1901)

If your POV is bound to the way it already is, then you have just signed yourself up for a lifetime of competition (Picasso vs Van Gogh vs Monet vs Manet vs Renoir, etc.) before your journey has even started. (Location 1911)

Writers, creators, founders, investors, bankers, lawyers, the vast majority of the business ecosystem takes whatever is placed in front of them and says, “I accept the premise.” And there is very little questioning around whether we are having the right conversation (context) to begin with. (Location 1921)

If you are one of those fish, you spend your entire life living in water. All you know, and all you’ve ever seen, is water. You “accept the premise.” From the moment you were born, water. Your fish parents, all they ever talk about is water. Your aunts and uncles, brothers and sisters, all live happily ever after in water. Not once, ever, do you question whether or not you live in water. Everywhere you see is water. Why would there be anything except water? (Location 1946)

The world is not the same way it was yesterday. We REJECT the premise. And we are going to act as if the tomorrow we’re creating already exists, today. (Location 1967)

“Legendary builders must stand in the future and pull the present from the current reality to the future of their design. People living in the present usually dislike breakthrough ideas when they first hear about them. They have no context for what will be radically different in the future. So an important additional job of the builder is to persuade early like-minded people to join a new movement.” (Location 1970)

Imagine what breakthrough insight one of these legendary authors may reveal to the world, fundamentally changing the way the masses thought about your category of “thing.” (Location 2022)

The rule of thumb here is that if your tagline, and subsequent POV can easily work for someone else, that means you don’t have a POV. You have a meaningless brand and tagline (that could be used by lots of other companies). (Location 2057)

Most people point to the “No Software” POV as a strategic component of Salesforce’s success in designing a category. And it was. But most people also forget that Salesforce successfully Framed, Named, and Claimed the problem with the old category as well—and they did so with new languaging. (Location 2094)

The magic combination of Category Design is both Naming & Claiming the future (where you are going), as well as the past (“you don’t want that old thing, do you?”). (Location 2101)

Category Design is a game of thinking. You are responsible for changing the way a reader, customer, consumer, or user “thinks.” And you are successful when you’ve moved their thinking from the old way to the new and different way you are educating them about. (Location 2163)

When Henry Ford called the first vehicle a “horseless carriage,” he was using language to get the customer to STOP, listen, and immediately understand the FROM-TO: the way the world was to the new and different way he wanted it to be. (Location 2185)

And your Point Of View frames a new problem and a new solution in a provocative way. If marketing is your ability to evangelize a new category, and branding is how well you can associate your product with the benefits of the category, then languaging is how you market the category, and your brand within that category, based on your company’s unwavering, unquestionably unique point of view. (Location 2189)

Impotence has very negative implications attached to the word. If a man says he is impotent, it’s as though he has a character flaw. It means “not manly” or “unable to be a man.” That’s not a word very many men want to be associated with—meaning men don’t want to admit to having such a problem. (Hard to sell a solution to a problem no one wants to admit to having!) (Location 2214)

Languaging hints at the benefits that come with radically different manufacturing: An eBook is a dematerialized book. It can be produced infinitely, distributed infinitely, edited and uploaded in an instant, etc. One single letter “e” tells customers, “This thing isn’t created, distributed, or consumed the same way regular “books” are.” (Location 2257)

Languaging also hints at the benefits that come with radically different distribution: OnlyFans call creators who invite other creators to the platform using their referral link “Referred Creators,” which signals the benefits of their flywheel and the money you can earn as a result. (Location 2260)

If your languaging does not tell one of these 4 story arcs, no one is going to listen to what you have to say. There is no urgency. You are responsible not just for strategically using new words to frame new problems (or reframe old problems), but to also reveal whether the slope is positive or negative—are the numbers going up or down? (Location 2340)

Most writers don’t realize that differentiation in writing has very little to do with the actual words on the page, and has everything to do with the words you use to illustrate different thinking. (Location 2385)

The book is about “that magic moment when an idea, trend, or social behavior crosses a threshold, tips, and spreads like wildfire.” Said differently, the book is basically an explanation of how word-of-mouth marketing works. (Location 2388)

What made it seem novel was the new & specific language (the Framing, Naming, and Claiming) Gladwell used to redefine (or redesign) the topic. (Location 2391)

When you write, you are engaging in the process of clarifying your thinking. When you clarify your thinking, you have the opportunity to differentiate your thoughts from other unclarified thinkers and writers. When your thoughts become more and more differentiated than anything that currently exists, people listen. And when people listen, you become “the authority.” (Location 2426)

Writers think “books don’t sell,” and would rather take the perceived credibility of being published by a traditional publisher to warrant higher speaking and consulting fees. (Location 2475)

Let’s say the three of us weren’t Pirates, but folks pursuing prestige and credibility (as most who write and publish books with traditional publishing houses do). (Location 2538)

For example, Pirate Cole has been republishing his entire library of articles behind Medium’s paywall for more than 2 years—and has made more than $100,000 doing so. (Location 2579)

Instead of writing a book, first, you decide to create shorter-form content and distribute it via paid newsletter (on a platform like Substack). This allows you to: (Location 2582)

Said differently: instead of trading 90% ownership of your content for an advance that buys you six months or a year of time to write your book and then having to use your advance to fast-track your audience building and marketing, you can maintain 100% ownership and generate the same or more as your advance would have paid you, while (Location 2586)

Now let’s take Pirate Eddie’s Superconsumer math and say that the Top 10% of your customers generate 70% of the sales. This rings true, as the vast majority of our own books were big bulk orders by the top venture capital firms, Fortune 500 companies, and large conferences (if you want to know how New York Times best-sellers juice the rankings, this is how they do it). (Location 2590)

Whether you are an Obvious or Non-Obvious writer, creator, entrepreneur, or executive, the pinnacle of sharing your insights with the world is writing a book. (Location 2609)

Now, obviously we are not here to tell people how to crap out 200 pages of platitudes, slap a cover on it, and give themselves a new badge (“author”) to wear at tomorrow’s dinner party. Writing a book for the sake of writing a book is a waste of your time, and the reader’s. (Location 2616)

But ask these authors what makes one of their ideas (books) more successful than the others, ask them what caused some of their ideas to scale, and they all repeat the same answers: (Location 2641)

This is the most extensive research done on why certain ideas scale and others do not, leveraging modern business data through a Category Science lens. (Location 2651)

Books are the most professional and powerful way to present new ideas through a point of view. And why we were fascinated studying the best-selling business books of the past 20 years is not solely because we wanted to create a framework for engineering success ourselves. (Location 2655)

What this study (shockingly) revealed to us is that the publishing world, as well as the business world at large, doesn’t know the first thing about writing books that make a giant difference (and before completing this study, neither did we—despite the fact that we’ve sold hundreds of thousands of books in the past). (Location 2699)

But if you want to swing for the fences, then your big idea needs to fall into one of these 7 categories: Personal Development Personal Finance Insights/Thinking Leadership Case Study/Allegory Functional Excellence Relationships (Location 2719)

This is not an accident. As Pirate Cole says often: “The size of the question dictates the size of the audience.” Which means in order to reach millions of readers, or write a book that unlocks millions of dollars in revenue, you need to answer big, universal questions. If you don’t, it doesn’t matter how “good” you think the book is—the question the book is answering doesn’t have enough scale. (Location 2723)

While Personal Finance is the second-largest percent of revenue at 19%, it is 24% less productive and 18% less profitable than the average business book. (Location 2761)

What is interesting is its staying power. Insights/Thinking books have a flat 3-year CAGR, but are positive from 4 year to 15-year CAGRs. (Location 2774)

Idea-Centric books have slightly better unit economics generating slightly more revenue per unit, whereas Author-Centric books generate more Amazon reviews, but slightly less revenue per unit. (Location 2874)

Let’s say you are the CEO of a successful company (or maybe you’re a professor, executive, leader, creator, or anyone else who wants to make the future different), and you want to write a book. (Location 2910)

Ask yourself: Do you want acceptance? Or do you want to make a difference? (Location 106)

So, if you want to write a legendary business book, you want to consider how you can present Non-Obvious solutions to Obvious problems. This is the vast majority of the books on our Top 444 list. (Location 3033)

However, if you want to become known for a niche you own, and you want your reign to last decades (or even lifetimes), then you want to be in the business of educating the world on Non-Obvious problems— problems they didn’t know they had until you came along and opened their eyes. And then you want to give them an Obvious, candy-coated solution they can use right away to solve this newfound problem they now can’t get out of their mind. (Location 3062)

He or she who frames the problem owns the solution. (Location 3077)

Even though it’s harder (and takes longer) to educate the world on a problem they didn’t know they had, the timeline of your category dominance will last tremendously longer. (Location 3077)

So again: if you want fame and fortune now, provide Non-Obvious solutions to Obvious problems—but realize your shelf life will be shorter. (Location 3083)

But if you are willing to postpone fame & fortune a bit, and would rather build a more defensible moat around your niche (and optimize for impact, contribution, and legacy), then educate the world on Non-Obvious problems and give them simple, actionable, Obvious solutions they can put into practice right away to solve the problem they now know they have (because of you). (Location 3084)

If you want your book to resonate with a large number of people, your idea to “scale,” AND for your idea to be defensible and have a meaningful shelf life, then you need to either: Provide people with Obvious solutions to Non-Obvious problems Or educate people on Non-Obvious problems they didn’t (Location 3101)

Law #1: Clear, Not Clever (Location 3218)

So, don’t try to be clever. Just be clear. (Location 3224)

Law #2: Use Language That Signals The Primary “Benefit” (Location 3228)

The benefit of reading a book that provides an Obvious solution to an Obvious problem is that it’s simple. Easy to understand. Broken down into steps. Etc. (Location 3229)

So, use this language in the title or subtitle! “A Simple System” “Easy Exercises” “A Step-By-Step Approach” (Location 3230)

The benefit of reading a book that provides a Non-Obvious solution to an Obvious problem is that it’s surprising. Unconventional. Unknown, until now. So, use this language in the title or subtitle! “The Surprising Truth” “An Unconventional Approach” “The Little-Known Strategy” (Location 3232)

The benefit of reading a book that educates you about a Non-Obvious problem you didn’t know you were experiencing, and then gives you an Obvious answer or solution to solve it, is that it’s eye-opening. Shocking. Mind-boggling. So, use this language in the title or subtitle! “An Eye-Opening Perspective” “This Shocking Study” “A Mind-Boggling Research Report” (Location 3235)

Law #3: Title & Subtitle Should Mirror Obvious & NonObvious Pairing (Location 3243)

If you are writing an Obvious/Obvious book, then your Main Title & Subtitle should be Obvious/Obvious. (Location 3244)

If you are writing an Obvious/Non-Obvious book, then your Main Title & Subtitle should be some combination of Obvious/ Non-Obvious. (Location 3248)

If you are writing a Non-Obvious/Obvious book, then your Main Title & Subtitle should be some combination of Non-Obvious/Obvious. (Location 3251)

Do you want to make a difference? Then you need to divorce yourself from public approval. “Different” things don’t get accepted right away. Meaningful things take time to understand. And Non-Obvious connections require people to think—and guess what? Most people scrolling through social media don’t want to think. (Location 127)