Arrrrr! 🏴‍☠️ Welcome to a 🔒 founders-only edition 🔒 of Category Pirates. Each week, we share radically different ideas to help you design new and different categories. Founding subscribers can access the entire archive of 200+ mini-books and audiobooks. If you’re not a paid subscriber, hop aboard!

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Dear Friend, Subscriber, and Category Pirate,

So. About that job of yours.

The one you got hired for. The one you got promoted for. The one that, somewhere between the last offsite and the next one, quietly became a job nobody’s actually paying for anymore.

You probably felt it before you could name it. A Monday morning where the thing you’re best at feels weirdly less valuable than it used to. A meeting where someone under 30 mentions an AI Agent and everyone nods like they understood. A LinkedIn post from a peer announcing they’ve “transitioned into a new chapter” (translation: got laid off and is now a fractional something).

This is a category shift.

CFOs are watching their role morph from scorekeeper to category architect. Marketers are watching the cost center they’ve defended for decades get reframed as the highest-leverage profit engine in the company. Knowledge workers are watching the premium on “knowing things” collapse while they’re still mid-sentence explaining what they know. And careers, the supposedly linear thing your parents told you to build, are turning into a series of ruptures that either break people or remake them.

The old way was to work harder at the job you were given.

The new way is to redesign the job itself.

These 7 audiobooks are a field guide for the second move.

Listen in order or pick your rupture

You can go straight through the list, or jump to the audiobook that matches the function getting rewritten underneath you right now. Either works. What doesn’t work is pretending the rewrite isn’t happening.

Careers used to be ladders. They aren’t anymore.

This audiobook reframes the modern career as a series of Career Quakes. The layoff that reroutes you. The market shift that invalidates your specialty. The quiet realization that the role you trained for isn’t coming back. Most people treat these as failures. Creator Capitalists. treat them as the raw material for becoming irreplaceable.

You’ll learn why the people who come out stronger aren’t the ones who avoided the quake, they’re the ones who used it to design a new category of work only they can occupy.

If the ground has moved under you in the last 18 months, start here.

Peter Drucker named the knowledge worker in 1959. AI is un-naming them in 2026.

This audiobook doesn’t mourn the knowledge worker. It buries them and hands you the blueprint for what comes next. The 6-step shift moves you from selling hours, to selling outcomes, to selling outcomes AI can’t replicate: judgment, taste, POV, and category authority.

The uncomfortable part is that “being really good at your job” is no longer a moat. The freeing part is that you don’t need permission to build a new one.

If you bill for time, this audiobook will make you deeply uncomfortable. That’s the point.

The CFO role is getting split in half.

On one side: the Agentic CFOs who use AI Agents to run reporting, close the books, and monitor cash in minutes instead of weeks, freeing them to design the future of the business. On the other side: the CFOs still doing the work the agents now do, wondering why their influence is shrinking.

This audiobook introduces the Friedman Matrix and shows how the best CFOs are moving from scorekeeper to category designer. They’re in the arena shaping the P&L, not reporting on it.

If you’re a CFO, a founder working with one, or anyone who thinks finance is a back-office function, this one rewires the org chart in your head.

Tesla spends roughly zero dollars on traditional advertising.

And yet every Hertz rental counter that hands out a Model 3 is a multi-million-dollar marketing asset Tesla didn’t pay for. That’s not a coincidence. That’s category design.

Part 1 of this series opens with the Tesla case study and uses it to introduce a radical idea: marketing, done right, isn’t a cost. It’s a profit-positive engine that uses adjacent categories (like rental cars) to build demand for the primary one (like buying a Tesla).

If the word “marketing” makes your CFO flinch, this audiobook is the antidote.

Here’s the ugly truth most CMOs already know but can’t say out loud.

The reason marketing gets cut first in a downturn is because marketing teams agreed, at some point, to be measured as a cost. Once you accept cost-center framing, you’ve already lost the budget fight. Every quarter. Forever.

Part 2 makes the case for why that framing has to die, names the executives who keep it alive (usually accidentally), and lays out what marketing looks like when it’s structured as the growth engine instead of the expense line.

This is the audiobook to send to your CFO before the next budget cycle.

Parts 1 and 2 diagnose the problem. Part 3 is the prescription.

Five concrete steps for marketers who want to stop defending their budget and start owning the P&L. It covers how to restructure your team around profit contribution, how to price your output like an asset instead of a line item, and how to use Category Design to build marketing programs that generate revenue on their own.

If you’re a CMO trying to survive the next earnings call, or a founder trying to figure out whether your marketing leader is playing offense or defense, start with Parts 1 and 2, then run through Part 3 with your team.

Every audiobook above names a role getting rewritten.

Lightning Strike Legends shows you what happens when two people decide to rewrite theirs at the same time.

This audiobook is the behind-the-scenes story of a single Lightning Strike that produced a 4x ROI in three weeks. It’s tactical, specific, and refreshingly unromantic about how category momentum actually gets built. No vague “go viral” advice. Real choreography: what was launched, when, by whom, and why it worked.

It’s also the audiobook to listen to last, because it answers the question all six previous audiobooks raise. Which is: if the job is getting rewritten, what do I actually do on Monday?

Lightning Strike Legends is one answer. Not the only answer. But it’s proof the answer exists.

The job you were hired to do is not the job the market is now paying for.

That’s the throughline running through all seven of these audiobooks, which is why we dropped them in the same batch instead of spacing them over six months. The rewrite is happening now. The Category Designers who see it first get to design the new role. Everyone else gets assigned to one.

So. Press play. Take the walk. Let the headphones do what meetings can’t.

And when you hear the audiobook that names the thing you’ve been feeling but couldn’t quite say out loud, don’t be surprised. That’s sort of the whole point.

Arrrrrrr,

Category Pirates

Eddie Yoon

Christopher Lochhead

P.S. - Audiobooks show you the rupture. The Academy is where you learn to design what comes after it.

If any of these audiobooks land, there’s a real next step sitting right in front of you.

Category Design Academy Cohort 4.0 applications close this Sunday, April 27. The cohort starts May 4.

The Academy is where pirates go to stop reacting to category shifts and start designing them. It’s where the CFO in your head becomes the Agentic CFO. Where the marketer in your org chart becomes the profit center. Where the knowledge worker clocking hours becomes the category authority who gets paid for outcomes.

Listening is the diagnosis. The Academy is the prescription.

👉 Apply before Sunday here.

Arrrrr! 🏴‍☠️ Welcome to the Pirate Street Journal, a free weekly read on category design, markets, and what it means to think different. For more: Audiobooks | Creator Capitalist podcast | Books | Sign up for a Founding subscription to ask the Pirate Eddie Bot your category design questions.

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Dear Friend, Subscriber, and Category Pirate,

When the market breaks, category designers get to work

Pirate Eddie was on Schwab Network last Friday.

The data he walked through wasn’t encouraging.

Disposable personal income down 1% in February. Personal consumption expenditures up 5%. GDP at 0.5% last quarter, down from 4.4% the quarter before. Michigan consumer sentiment is sitting at 47.6%, down 11%.

Consumers are spending more than they have and feeling worse while they do it.

Is that bad news for you?

Only if you’re playing the old game.

Smart money is already moving.

While most companies are playing defense, smart money is making directional bets on what comes next.

Costco is building gas-only stations for the first time in company history. A 40-pump station is already open in Mission Viejo. A 240-pump station is planned for Honolulu in 2027. That is a CapEx commitment that says: we believe high gas prices and inflation are the new operating environment.

Anheuser-Busch just bought 85% of Beatbox Beverages for half a billion dollars.

Why? Because while wine is down 7.7%, spirits are down 4%, and beer is down 4%, Beatbox did $340 million in retail last year at 50% year-over-year growth. Sweet and spicy cheladas. Off-premise occasions. Music culture identity. A container designed for how younger consumers actually want to drink.

Beatbox didn’t beat the beer category. It created a new category.

And Anheuser recognized what was happening before it was obvious.

Down markets don’t shrink categories. They sort them.

When consumer spending contracts, it doesn’t contract equally. Nice-to-have dollars shrink. But they don’t disappear. They get redirected.

Consumers stop spending on things they’ve already done. Things they’re bored of. Things that feel like more of the same.

They choose different.

And that is not a headwind for a category designer.

When people stop spending automatically and start choosing deliberately, the question becomes: what are they choosing between? Who named the problem they didn’t know they had? Who framed the decision before anyone else thought to?

That’s your job.

The companies bleeding right now optimized for execution inside someone else’s map. The ones gaining ground built their own.

Beatbox didn’t ask how to win in beer. Costco didn’t ask how to compete on gas price. They asked: what category could we design that doesn’t exist yet where we will win?

That is exactly the question this market is demanding right now.

There is no better time to build a new category

A down market feels like bad news. But for category designers, contraction is signal. It tells you precisely where the old map stopped working and where the new one needs to be drawn.

When consumers choose different, they need new language to describe what they’re choosing. They need someone to name the problem. They need a category that didn’t exist before.

Category designers don’t just do well when markets contract. They stop being at the mercy of market cycles altogether.

When you own a category, you’re not competing inside someone else’s shrinking market. You set the price. You define the problem. You decide what winning looks like.

The economy shifts around you, not beneath you.

That’s how your life’s work compounds.

If that framing resonates, there are two ways to go deeper.

1. The Category Design Academy’s next cohort begins May 4. Applications close April 27. This is where people who’ve been most right about something for the longest time finally get the language, the frameworks, and the structure to build around it. Apply here.

2. If you want a thinking partner that will push back on your category thesis and help you name the problem no one else is naming, The Pirate Eddie Bot is built for that. It’s the only AI trained on category design and Creator Capitalist, and it comes with a Founding membership. Become a Founding Subscriber here.

Arrrrrrr,

Category Pirates 🏴‍☠️

Eddie Yoon

Christopher Lochhead

P.S. — Your superconsumers are also sorting their categories. Including yours.

The question is whether you’re building the category they’re choosing next.

New markets don’t just need new products. They need new language. The companies that win in a down market are always the ones who named what was happening before anyone else had words for it. Beatbox didn’t just make a different drink. They named a different occasion. Costco isn’t just selling gas. They’re naming a new kind of membership value.

And it starts with language.

The Academy is where that language gets built. Not handed to you, but excavated from what you already know, sharpened by a room of people working on real things, and stress-tested until it holds.

The books give you the model. The Academy gives you the room to build with it.

If you’re ready to name the category this market is creating space for, applications close April 27. [Apply here →]

Not ready for the Academy? The Pirate Eddie Bot is the only AI trained on Category Design and Creator Capitalism, and it’s included with a Founding membership. [Start here →]

This is a 🏴‍☠️ Founding Members 🏴‍☠️ post. Founding Members get access to the Pirate Eddie Bot to ask category design questions, weekly actionable insights, the full library with 30+ audiobooks 2000+ mini-books, and more. See the Founders Deck here.

Subscribe now

Dear Friend, Subscriber, and Category Pirate,

Jim Cramer asked Jensen Huang a simple question last week.

If AI is so awesome, then why are companies laying people off?

Jensen’s answer should be framed on the wall of every CEO in America.

“For companies with imagination, you will do more with more. For companies where the leadership is just out of ideas, they have nothing else to do. They have no reason to imagine greater than they are. When they have more capability, they don’t do more.”

Read that again slowly.

This is the man who built the most important tech on earth.

This is the man who built the most valuable company on earth.

This is the man who says he sees one trillion dollars of demand for 2 of his products.

He just put every CEO on notice.

If you use AI to cut headcount, it means you ran out of ideas.

Pirate Christopher has been an officer and director of public companies.

He knows how this works. Anything that gives leadership air cover to cut the people they wanted to cut anyway, companies take it. The technology is convenient cover for decisions that were already made.

Do you work for a company whose CEO who Pirate Jensen says lacks imagination?

We see you. We feel for you as you endure a current or coming Career Quake.

Your job changed overnight. Or you got the call. Or you can feel it coming and you’re not sleeping well.

The fear and disruption are real. And the instinct to react is completely human:

• Network harder.

• Scramble and update your resume.

• Put your head down and try to outwork whatever is coming.

You can’t dodge a quake. You can’t avoid a quake. You can’t change the fact that your CEO lacks the imagination or courage to use AI to create an abundant future like no one has ever seen before.

Their ceiling is not your ceiling.

Don’t be reactive. Be proactive.

This isn’t an AI quake. It’s an imagination quake.

Our Career Quakes mini-book maps exactly this: the organizational ring just went red for a lot of people, and the reflex is to blame the global ring.

AI is not the problem.

What’s different between the companies expanding and the companies cutting is the same thing that has always been different: whether the people at the top can imagine a bigger future than the one they’re currently in.

Jensen didn’t say AI elevates companies. He said AI elevates people with imagination.

Every carpenter could become an architect. Every plumber could become an engineer. The tool expands what’s possible for people who know what they’re trying to build.

Creator Capitalists are builders. You are a builder.

Don’t wait to find out if your CEO has an imagination ceiling.

The Creator Capitalists we work with who are navigating this right now aren’t asking, “Will AI take my job?”

They’re asking a completely different question: what is the category only I can design, and how do I build it before everyone else figures out what I already know?

Ask one question to elevate your imagination

Creator Capitalists are not people who suddenly had a brilliant idea.

They’re people who fell in love with a problem. They know how much time, money, and joy this problem costs people. They are on a mission to solve this problem, no matter what it takes.

And for them, AI is like having Steph Curry join your pick-up basketball team.

Just pass AI the ball and watch it go in.

Which brings us to the only question worth sitting with this week:

What problem have you fallen in love with and believe AI has elevated your imagination and ability to solve it with a powerful POV only you can bring to the world?

Take your time with this. The real answer doesn’t come fast.

What is the problem you’ve been quietly watching play out exactly the way you said it would? The problem that feels so obvious to you that you assumed everyone else must see it too.

They don’t. That’s not a coincidence. That’s your category.

Two Ways to Incubate Your Imagination

If you’re mid-quake right now, there are two places worth your time.

Because you don’t have to take your Creator Capitalist journey alone.

The first is The Pirate Eddie Bot—the only AI on the planet trained on Category Design, Creator Capitalism, and 200+ Category Pirates mini-books. Pirates are calling it the most valuable AI they’ve ever used. They have used it to find the language that made clients stop negotiating, design Lightning Strikes that generated thousands in new revenue, and name categories they’d been sitting on for years. It’s included with a Founding membership. If you want a thinking partner that will actually push back on your answer to that question—start here. If you’re already a founding member, dive in here.

The second is the Category Design Academy. This is the room where people who are tired of rebuilding in the rubble of someone else’s imagination come to design their own category. It’s not for everyone—it’s for the people who read Jensen’s quote and thought: that’s me. I have more imagination than the room I’m in. And it’s time to do something about it.

If that’s you, applications open today.

Jensen spent his shift at Denny’s hoping to make it through. The biggest tip he ever got was two or three dollars. Now he’s building technology that has increased computing demand by one million times in two years.

He said he hopes to die on the job.

That’s what it looks like when someone found their category.

Arrrrrrr,

Category Pirates 🏴‍☠️

Eddie Yoon

Christopher Lochhead

P.S. — The room where people stop rebuilding in someone else’s rubble is opening this week.

The Category Design Academy is not a course. It’s not a coaching program. It’s a room where people who already have something real—a business, an expertise, a point of view the market hasn’t caught up to yet—finally get the language, the strategy, and the community to build around it.

The people who belong here are doing six figures, have driven real outcomes, and are done explaining what they do to clients who don’t get it. They want to own a category. They want pricing power. They want to stop sounding like everyone else.

If you read Jensen’s quote and felt something—if you’ve been the most right about something for the longest time and you’re ready to stop waiting for permission to build around it—this is the room.

Category Design Academy applications are open now. [Apply here →]

Not ready for the Academy? The Pirate Eddie Bot is the only AI trained on Category Design and Creator Capitalism—and it’s included with a Founding membership. [Start here →]

This is a 🏴‍☠️ Founding Members–Only 🏴‍☠️ post. Founding Members get access to the Pirate Eddie Bot to ask category design questions, weekly actionable insights, the full library with 30+ audiobooks 2000+ mini-books, and more. See the Founders Deck here.

Subscribe now

Dear Friend, Subscriber, and Category Pirate,

Something happened in our Category Design Academy workshop this morning that stopped the room.

Pirate Mary Johnson has coached people through the transition from freelancer to business owner for years. She said the number one thing—every single time—is being afraid to charge what you’re worth.

Then she read Chapter 17 of Creator Capitalist.

“I hadn’t thought about worth in terms of value in that way until that chapter.”

Pirate Christopher teared up. He told her: once you put something into the world, it’s not yours anymore. What it means to you is not what it means to other people. And what Chapter 17 meant to Mary—a woman who has spent years trying to help people make this exact mindset shift—was something none of us expected.

The fear isn’t that you don’t have enough. It’s that you’ve never had a framework to see what you have—and put a number on it.

That’s what the four questions below are designed to do.

But first—here’s what’s happening right now.

The shift is happening with or without you

77% of US adults wish they could be paid to create. 75% believe they have unique skills that set them apart. 1 in 3 want to be a Creator Capitalist.

Most of them won’t move. They’ll think about it for another year. Another promotion. Another credential. And the people who did move will already own the conversation.

But right now, people aren’t waiting. They’re going down the rabbit hole and not coming back up. They’re posting without being asked. They’re buying the book and reviewing it the same day.

A stranger we’ve never spoken to posted this on LinkedIn yesterday:

“This exact thing is happening to me right now with Category Pirates. I signed up to their email list last week. Went down a rabbit hole in their links. Now I’m seeing them everywhere—both in my inbox and social media. The inundation that I willingly signed up for is building trust at rapid speed. And it’s only a matter of time until I buy their new book.”

We didn’t ask for that. We didn’t know this person existed. A category is being born in public—and strangers are narrating it in real time.

The question is whether you’re going to watch this happen—or get inside it.

You already know. You just don’t have the framework to act on it.

You know you have more value than your title suggests. You know your ideas have been making someone else money. You know the old playbook—credentials, promotions, loyalty—stopped paying the way it used to.

You’ve known it for a while.

That knowing isn’t the problem. You don’t need more motivation. You don’t need another podcast to “inspire” you. You don’t need discipline.

You need a framework that turns what you already know into something you can see, name, price, and build on. A way to take the last 10 or 15 or 20 years of expertise and lay it out in front of you so the path forward becomes obvious.

That’s what Creator Capitalist is. 694 pages of framework.

And today, we’re going to distill those 694 pages into four questions you can sit with right now—and walk away with more clarity than most professionals get in a decade of wondering.

The questions give you the structure. The bot gives you the lens.

We tested these four questions using ChatGPT, Claude, and Gemini. They produced decent career advice. Thoughtful, even. “Find your niche.” “Build a personal brand.” “Consider freelancing.”

Then we asked the same four questions using The Pirate Eddie Bot.

The answers were different. Specifically different. Because the bot knows what a Superpower IS in the context of Category Design. It knows how the Four Capitals compound. It knows the difference between pricing time and pricing outcomes. It’s trained on 200+ mini-books of thinking that don’t exist anywhere else.

Generic AI gives you generic answers. The Pirate Eddie Bot gives you YOUR answers—through the only lens designed for this shift.

It doesn’t reflect your career back at you. It reflects your career through the Creator Capitalist framework. And what you see in that reflection is the clarity most people spend a decade chasing.

Here’s how to access the questions and the thinking partner behind them.

Below are the four questions that compress the core of Creator Capitalist into one sitting.

These are the same questions we ask people who pay $10,000 to be inside the Academy. They’re the questions that have generated the biggest breakthroughs across three cohorts. The questions that 119 people in our R&D cohort used to uncover $425M in quantified outcomes they didn’t know they had.

You have access to these questions AND the thinking partner that makes them produce real answers—The Pirate Eddie Bot. The questions give you the structure. The bot gives you the lens. Together, they do what years of journaling and “I should really figure this out” thinking haven’t—because they give you the Creator Capitalist framework to think through, not just think about.

This is how you sit down, engage in the deep thinking the book is designed to provoke, and walk away with something you can act on. Not next month. Today.

Not yet a Founding member? Join here and get access to the questions, The Pirate Eddie Bot, and the full 250+ mini-book, audiobook, and founder deck library.

Haven’t gotten the book yet? 200+ people have gotten their copy since yesterday. Here’s where to go:

• Paperback on Amazon — $35

• Ebook — $35 (instant access)

• Audiobook — $35 (instant access)

• The Complete Collection — $100 (hardcover + ebook + audiobook)

• The Course + Book — $500 (closes March 27—first time open in over a year)

Buy before March 20 and get the Book Rushmore Outcomes Analysis free—$425M in quantified outcomes from 119 Creator Capitalists. We’ll send it automatically.

694 pages distilled into one sitting: the four questions that show you what you’ve been sitting on

These four questions come from Chapters 3, 16, and 17 of Creator Capitalist. Each one builds on the last. Run them in order. Don’t rush. Sit with each one before moving to the next. The goal isn’t to finish—it’s to see.

Read more

This is a FREE 🏴‍☠️ Founding Members 🏴‍☠️ post. Founding Members get access to the Pirate Eddie Bot to ask category design questions, weekly actionable insights, the full library with 30+ audiobooks 200+ mini-books, and more. See the Founders Deck here.

Subscribe now

Dear Friend, Subscriber, and Category Pirate,

Last week, a spider chart from Anthropic’s new labor market impact report made waves. It shows two things: the blue area is what AI can theoretically do across every job category. The red area is what people are actually using it for.

Look at the gap.

In business and finance, computer science, architecture, engineering, management, education, and legal, AI can theoretically handle the vast majority of tasks. But actual usage? A tiny red sliver in the center.

That gap is the entire Creator Capitalist thesis in one image.

Remember, you don’t have to outrun the bear, just the slowest person?

• You don’t have to master AI at the blue level.

• You just need to be ahead of the red.

• Red is dead.

And the people moving toward the blue? We call them Creator Capitalists.

“Learning AI” Leaves You in The Red

Learning AI is a legacy Knowledge Worker’s response.

It treats AI as one of many skills, books, or classes to add to your resume. The problem is that AI is happening in real time, and knowledge takes months or years to be codified in a class, book, or some other form of legacy expertise.

By the time you find an AI expert, that expertise has expired.

And you will be far behind.

When Category Pirates started its AI journey over a year ago, we were told by an expert that we had to:

• Upload documents, quizzing, and correcting ChatGPT for 4-6 hours per day

• Repeat 7 days a week for 6 months

This seemed really daunting and demoralizing to start!

It turns out the advice was wrong.

Was the expert getting great results? Yes. Was it because of the hundreds of hours of training? Not likely, given the memory limitations of LLMs at that time.

It was far more likely a correlation than a causation. OpenAI was shipping its most aggressive model improvement run in history at the same time.

• September 2024: o1-preview launched with chain-of-thought reasoning roughly 8× better at complex tasks.

• November 2024: Projects and persistent Memory launched, making the manual daily uploads redundant.

• December 2024: o1 full release — 89th percentile on Codeforces, PhD-level accuracy on science benchmarks.

• February 2025: GPT-4.5 cut hallucinations by 40% (61.8% → 37.1%) and improved factual accuracy by 4× over GPT-4o on standardized knowledge tests.

This meant that a beginner was just as well-positioned as an expert.

You are far better off building as a beginner than learning from an expert. That's the Creator Capitalist approach to AI—and it's one of the reasons we devoted two full chapters of the book to it.

‘Build with AI’ in the Near Blue

19-year-old Zach Yadegari had just been rejected by his dream colleges like Stanford, MIT, Harvard, Columbia, Princeton, Duke, and Cornell. Despite his 4.0 GPA and 34 ACT score.

And yet, he just sold Cal AI, his $30 million ARR photo-based calorie tracking app, to MyFitnessPal for $50 million.

Zach didn't build in the deep blue at the farthest reaches of the spider chart. He didn't try to solve problems AI can't touch yet. He built just outside the red, in the shallow blue, where the models were good enough, the category was proven, and the timing was right.

Cal AI wasn't science fiction. MyFitnessPal already had a photo calorie feature. What Zach did was execute it faster, with better models, to a younger audience that the incumbents had stopped paying attention to. That's why MyFitnessPal bought it. You don't acquire what you can't build. You acquire what someone else already built, scaled, and owns.

Zach is 19. He didn't have a pedigree, a network, or a decade of experience. He had a point of view and the tools to build on it. That's Creator Capitalism.

Creator Capitalists don’t learn AI. They build with AI. They show up with judgment, perspective, and a problem worth solving—and they use AI to scale what makes them different.

Play with AI in the Far Blue

One person with a point of view and AI can now produce what used to require an entire team. We watched it happen live on our podcast last week when Pirate Eddie uploaded 20 unstructured Creator Capitalist profiles into Claude and produced category science—data visualizations, origin story analysis, career stage breakdowns—in one sitting. Work that would have taken a consulting team a full week.

Eddie didn’t “use AI.”

He was playing with it. Much like an orchestra conductor says, what if we played this much faster and quieter? Or an NBA coach tells Steph Curry he has a green light to shoot from half-court. Or an amazing chef decides, what if I made a savory cannoli?

Pirate Eddie asked Claude (his wife calls it Cleddie), please turn these words into magic numbers. And make it pretty.

He brought a hypothesis. AI brought processing power. Together, they created Intellectual Capital that neither could have produced alone.

If you’re an alumni of the Creator Capitalist course, you can check out the full report in the Mighty Network space.

Don’t Wait for Permission

Some people aren’t waiting for permission.

Mary Johnson—CXO, Mischief Maker, and a Category Design Academy Student—posted this last week:

“I know for a fact that the only reason I haven’t started and exited multiple successful companies is because of my own mental model limitations based on all the crap I have told myself over the years. The person I needed to become who is capable of those multiple exits didn’t exist until now. And she currently knows that NOW is the time for her to emerge and GSD.”

Mary didn’t post about learning a new tool. She posted about becoming a different person. That’s the shift. The obstacle was never the market, the timing, or the technology. It was the story she was telling herself about what she was allowed to become.

She also said something that should make every professional reading this sit up:

“If you aren’t creating net new value by becoming a Creator Capitalist, you will be left behind over the next 24 months and be on the wrong side of the door to this party.”

Twenty-four months. That’s Mary’s timeline. Given what we just saw in those two viral posts—AI theoretically capable of most knowledge work, and a live demo of it replacing a day’s work in four minutes—twenty-four months might be generous.

Name what you see that others don’t

Here’s what we’ve noticed working with hundreds of professionals over the last few years: the people who successfully made the Creator Capitalist shift didn’t start with a business plan. They didn’t start with a website. They didn’t start with a side hustle.

They started with a conversation.

They sat down—with a mentor, a thinking partner, a co-founder, or increasingly with AI—and they answered one question honestly:

What do I see that other people in my industry don’t?

That question is the seed of everything. Your Superpower. Your Intellectual Capital. Your point of view. The problem you were born to solve. Every Creator Capitalist in our book traces their origin back to a moment where they named something nobody else was naming.

Thomas Parrott was a DTC executive who thought his niche was taking US companies to Europe. One jam session later, “Contribution Margin Growth Architect” crystallized—and his sales cycle collapsed from 30 weeks to 30 minutes.

Danny Bauer was a school principal talking about leadership the right way for ten years—but using the wrong words. One throwaway line in the Academy became “Ruckus Makers,” and it acted like a tractor beam for the exact leaders he wanted to serve.

Melissa Andrews and her husband were building an agricultural connectivity company, but the market didn’t know they existed. Then Tom, Melissa’s husband, coined “Digital Darkness” on a plane—two words that captured an entire category. It worked in Australia, New Zealand, the UK, Canada, and the US.

The naming didn’t create their superpower. It unlocked it. Clarity created confidence. Confidence created pricing power. Pricing power created freedom.

Once you have articulated what you see that others don’t, start building with it in the near blue.

Then start playing with it in the far blue.

Build and Play with the Pirate Eddie Bot

The Pirate Eddie Bot is the only AI on the planet trained on the Creator Capitalist framework, the Four Creator Capitals, Category Design, and 200+ Category Pirates mini-books. ChatGPT doesn’t know what a Superpower is in the context of category design. Claude doesn’t know the difference between a Knowledge Worker and a Creator Capitalist. No generic AI can walk you through the specific frameworks in our book—because those frameworks don’t exist anywhere else.

The Pirate Eddie Bot does.

Tell it what you do. Tell it what you’ve built inside your company. Let it show you what you own that you don’t realize you own—and what it could be worth if you codified it under your name. Let it push back. Let it ask you the questions your boss would never ask because the answers would make you too expensive to keep.

The bot won’t just help you see your Intellectual Capital. It’ll help you figure out how to package it, price it, and turn it into something that pays you—whether you make the leap next month or next year.

👉 Founding Subscribers can start jamming with the Pirate Eddie Bot here.

The book drops in six days. But the people who walk into March 17 having already audited their Intellectual Capital—having already seen the number, felt the sting, and started mapping what it’s worth—they’re going to read the book like a blueprint, not a concept.

Start today. The bot is waiting. And it won’t judge your puke.

Upgrade to Access Pirate Eddie Bot

Creator Capitalist launches March 17.

Join the waitlist at creatorcapitalist.ai.

You’ll get the Introduction and Section 1 opener immediately, early ordering on March 16, and a launch-week bonus we’re announcing soon.

The Anthropic chart showed you the gap. The GPT-5.4 demo showed you the speed. Mary showed you the mindset. The Pirate Eddie Bot gives you the first step.

Six days.

Arrrrrrr,

Category Pirates 🏴‍☠️

Eddie Yoon

Christopher Lochhead

This is a FREE 🏴‍☠️ Founding Members 🏴‍☠️ post. Founding Members get access to the Pirate Eddie Bot to ask category design questions, weekly actionable insights, the full library with 30+ audiobooks 200+ mini-books, and more. See the Founders Deck here.

Subscribe now

Dear Friend, Subscriber, and Category Pirate,

You’ve spent 15, 20, maybe 30 years accumulating assets. You just haven’t been tracking them—because they were always deposited into someone else’s account. The company’s balance sheet. The military’s mission. The tech firm’s valuation.

You built their categories. They kept the equity.

And now you’re standing at some version of the same crossroads: Do I keep going? Or do I finally build something that’s mine?

If you’ve been reading Category Pirates for any length of time, you’ve heard us talk about the Four Creator Capitals. Probably more times than you’d like. We’ve referenced them in mini-books, taught them in the Academy, built workshops around them.

So why are we breaking them down again?

Because after working with hundreds of pirates—we’ve realized most people think they understand the capitals. They can name them. They nod along when we describe them. But few have actually mapped their own.

And the gap between understanding a framework intellectually and applying it to your own life is where most people stay stuck. Sometimes for years.

On March 17, we publish Creator Capitalist—the most important thing we’ve written since Superconsumers and Play Bigger. The book goes deep on all four capitals and gives you the complete system.

But we don’t want you to walk in cold.

If you’ve been wondering how people actually get paid to be themselves—not as a slogan, but as an economic reality—this is the flywheel that makes it work.

Below, we’ll break down each capital with a story that shows what it looks like in practice. Then, at the end, we’ve included a self-assessment so you can map where you actually stand—before the book even comes out. (Fair warning: some of the questions are uncomfortable.)

And if you already know this is for you—join the waitlist at creatorcapitalist.ai. You’ll get the Introduction and the opening of Section 1 for free immediately, and you’ll ne able to order a full day before the public launch on March 17.

Let’s get into it.

The Four Creator Capitals

Think of these as four interconnected assets. Each one amplifies the others. Together, they form the foundation for a career where you own what you create—and get paid accordingly.

1. Financial Capital

Financial Capital is the money you’ve saved, invested, or built that lets you cover your expenses and fund your ambitions. It’s the resource that makes courage rational.

Most people think they need millions before they can make a move. They don’t. They need enough—enough to cover their version of “pay for the party” while they build everything else.

Pirate Christopher was 18 years old, broke, and struggling with his first startup. Regular school didn’t work for him, so he self-curated an education—books, tapes, courses. His perspective on money was shaped by growing up without it. Lack of money owned him.

That shifted at a seminar where a workshop leader named Bix Bickson was going back and forth with a woman in the audience. Money was the excuse for every problem in her life. She believed she couldn’t make money. She believed only crooked people got rich. Struggling was part of her identity. Christopher sat there nodding along—because lack of money owned him too.

Finally Bix said: “There is a lot of money in the world, right?” She kept arguing. He kept asking. She finally snapped: “YES. There’s a lot of money in the world, Bix.” And he said: “GREAT! Now go out and get some!”

Christopher thought Bix was kind of mean. But then he thought: What if Bix is right?

Ten years later, at 28, Pirate Christopher was a millionaire running marketing for a publicly traded software company in Silicon Valley.

Your relationship with money is more important than your money.

Your relationship with money is more important than your money.

Your relationship with money is more important than your money.

When you see money as a tool instead of the goal, you gain clarity. And clarity is what lets you design a financial runway instead of just hoping one appears.

The VP of Engineering sitting on $2M in vested RSUs has a different Financial Capital challenge than the retired Colonel with a military pension. But they both need to answer the same question: How much runway do I actually need to make my move—and do I already have it?

Most people have more than they think.

2. Reputation Capital

Reputation Capital is the signal that travels ahead of you.

It’s what problems people associate with your name. And in a crowded world, being known for something specific matters more than being competent at everything.

Holley Miller was the Director of Marketing for the healthcare business at Allergan. While she was there, she helped grow a brand from $25 million to $100 million in four years.

The outcome was incredible. But how she did it was the real story.

She didn’t add incremental sales reps. She reframed the market. She focused on educating buyers about what was missing, what outcomes actually mattered, and why the old way of doing things no longer made sense. The product didn’t change. The belief about the category did.

After that, people started calling Holley, she had a reputation for outcomes. They wanted to know if she could help them get the same result.

That’s when she realized she had a superpower. She helped create a 9-figure outcome in an extremely cost-efficient way that nobody thought was possible. Any rational company would pay low 8 figures for a low 9-figure outcome. Holley was being paid 6 figures instead.

So she decided to value her value. She left and founded Grey Matter Marketing—where she now helps life sciences companies 4x their revenue using the same frameworks she built inside someone else’s company.

Holley didn’t build her reputation by promoting herself. She built it by reframing a problem so clearly that people couldn’t stop talking about the result. The calls came to her. That’s Reputation Capital at work.

3. Relationship Capital

Relationship Capital is the small number of people who multiply your efforts.

We’re talking about the eight to ten relationships that open doors, pressure-test your ideas, create trust at speed, and amplify your reach when it matters. Careers don’t scale linearly. People do.

When Charles Barkley was drafted by the Philadelphia 76ers, he wasn’t getting playing time. As a rookie, he did what most ambitious people do—he went to someone he respected and asked for advice. Moses Malone was a Hall of Fame player and the star of the team. Barkley asked him: “Why am I not getting more playing time?”

Moses’s response: “Because you’re fat and lazy.”

Barkley went home and cried that night.

But then he did something most people don’t. He listened. He went back to Moses and asked for help. Barkley weighed 300 pounds at the time. Moses said: “Let’s lose 10 pounds.” Barkley did. Then Moses helped him lose another 10. And another. Each drop meant more speed, higher jumps, more results, more playing time.

At 250 pounds, Charles Barkley became a starter and began to wreak havoc on the league. He earned the nickname “The Round Mound of Rebound” and went on to become one of the greatest players in NBA history—and now earns about $21 million per year as the most entertaining sports TV pundit alive.

When Barkley was inducted into the Hall of Fame, Moses Malone introduced him. When Moses passed away, Barkley gave the eulogy and called him “Dad.”

Moses Malone was the kind of friend who…

• Saw more upside in Barkley.

• Loved him enough to tell him the truth.

• Yearned to play with a fit (not fat) Barkely.

That’s Relationship Capital. Not a LinkedIn connection. Someone who cared enough to say the thing nobody else would say—and then showed up every day to help you do something about it. The people who change your career aren’t the ones who tell you you’re great. They’re the ones who tell you the truth and stick around for what comes next.

One of the more uncomfortable exercises we do with professionals in the Academy is asking: Who are the five people who would vouch for you tomorrow if you announced you were starting something new? Most people can name them instantly. Very few have ever activated those relationships. And even fewer have someone in their life willing to say “you’re fat and lazy”—and mean it as an act of love.

4. Intellectual Capital

Intellectual Capital is what happens when what you see, what you know, and what you believe gets turned into assets that outlive your time and effort.

Knowledge alone doesn’t create leverage. Codified knowledge does.

The surgeon who’s performed 10,000 procedures has extraordinary knowledge. But that knowledge is trapped in her hands—she can only see so many patients in a day. The moment she codifies that knowledge into a framework, a course, a diagnostic tool, or a piece of content, it scales beyond her time. That’s the shift from Knowledge Worker to Creator Capitalist.

Pirate Eddie learned this the hard way.

When he was 23—fresh out of college and consulting for high-growth companies—he built an Excel model and strategic framework for CFOs navigating rapid scale. It was brilliant work. Original thinking. The kind of framework that makes a client say “where has this been my whole career?”

Someone else at the firm recognized the value. They claimed it. They wrote a book based on it. And they drove tens of millions in consulting fees from Eddie’s intellectual property.

Eddie’s ideas. Someone else’s name. Someone else’s wealth.

He was 23. He didn’t know better. But most of the professionals reading this are 42, 48, 55—and they’re still making the same mistake. Every framework you’ve built inside a company. Every strategic model sitting on a shared drive. Every approach you’ve refined over decades that your colleagues use without crediting you. That’s your Intellectual Capital. And right now, it’s generating value for someone else.

If you don’t put your best thinking out there under your name, someone else will. The longer you wait, the more Intellectual Capital you leave on someone else’s balance sheet.

The book covers all four capitals in depth—including the specific frameworks for building each one. Join the waitlist at creatorcapitalist.ai to be first in line on March 16.

These four capitals aren’t separate buckets. They’re a flywheel.

• Your Intellectual Capital feeds your Reputation Capital—when you publish a framework that solves a real problem, people notice.

• Your Reputation Capital attracts Relationship Capital—the right people want to collaborate with someone who thinks differently.

• Your Relationship Capital drives Financial Capital—opportunities, partnerships, and revenue follow trust.

• And your Financial Capital fuels more Intellectual Capital—when you’re not scrambling for the next paycheck, you can invest in creating your best thinking.

Once this flywheel starts spinning, it compounds. You become what we call a Category of One—someone who can’t be replaced or commoditized—because your combination of capitals is unique to you.

“IRON” Mike Steadman went from running a struggling podcast agency to earning $25K+ contracts within months of designing his POV and building offers around his Superconsumers.

Pablo Gonzalez quit corporate construction, invented “Digital Word of Mouth,” and turned his frameworks and event planning knowledge into equity stakes—dramatically increasing his personal wealth and freedom.

They didn’t start from scratch. They mapped what they had, packaged it differently, and pointed it at people who valued it most.

That’s what the Creator Capitalist framework does. It turns what you already have into what you’ve always wanted: a career you own, work that compounds, and income that isn’t capped by someone else’s org chart.

Now here’s our challenge to you.

Don’t just read this and nod. Here are four questions to answer. If you can answer yes to all four, you’re in great shape.

If not, then you will want to dig deeper.

Because it says you’re not ready.

Go through each one. Be honest. The point is to see clearly where you are and where the opportunity is hiding.

Financial Capital

Question 1: Do you have 18-36 months of runway to sustain your current lifestyle if your income stopped today, until you can stand up your Creator Capitalist venture that pays you to be you?

How many months could you sustain your current lifestyle if your income stopped tomorrow? Write the number down. And don’t guess—find the real number based on what’s in your accounts right now.

Your goal is NOT to never work again.

Your goal is to make the leap to do the work you were designed to do.

To use your different, to make a massive difference for others and get paid to create.

That’s why your runway matters more than your retirement.

Are you worried your runway isn’t long enough? Chapter 6 of the book breaks down exactly how to calculate your “pay for the party” number and build a runway around it.

Reputation Capital

Question 2: If someone Googled your name right now, would they find your superpower?

Or would they find your LinkedIn title at someone else’s company? Your pedigree and education, that isn’t unique to you?

Or do you find your superpower. “I solve X problem for Y people to unlock Z outcome?”

Can you describe what you’re known for in one sentence—without referencing your employer? Not “I’m the VP of Strategy at [Company].” Something like “I help mid-market CFOs turn financial complexity into a competitive advantage.” If you can’t do that yet, your Reputation Capital is locked inside an institution.

It exists. It’s just not portable.

Chapter 7 teaches you how to unlock your Reputation Capital to create opportunities for you.

Relationship Capital

Question 3: Can you name five people—right now—who would take your call tomorrow and actively help you if you said “I’m building something new”?

Not people who’d say “that’s great, keep me posted” and then forget.

People who would buy your offer, tell others about it and/or write you a check.

Got five? Great job Pirate!

Chapter 8 helps you catalyze your Relationship Capital. For example, do the five people you just named know each other? Isolated relationships add value linearly. Connected relationships compound.

The best Creator Capitalists don’t just have strong individual relationships—they build constellations where their people know, trust, and amplify each other.

Intellectual Capital

Question 4: Do you have a proprietary process, playbook and intellectual property that makes you money while you sleep?

Think about the last time a colleague, client, or friend came to you with a problem—and you solved it in 15 minutes using a mental framework you’ve been refining for years. You probably shrugged it off. “That’s just how I think about things.”

That framework is Intellectual Capital. And right now, it lives only in your head.

Ask yourself: if you left your company today, would your best thinking leave with you—or stay behind on their servers, in their slide decks, embedded in their processes? How many frameworks, models, or approaches have you built over the years that other people use without crediting you? Have you ever seen someone present your thinking under their name—and felt that specific sting of watching your Intellectual Capital generate value for someone else?

What your answers are telling you

If you went through all four and thought “I have more than I realized”—you’re right. You do. Most people in your position do. The gap isn’t in what you have. It’s in the fact that nobody ever gave you a system for seeing it, organizing it, and building a flywheel around it.

That’s what Creator Capitalist is.

If you went through all four and felt uncomfortable—that’s the right response. Discomfort means you’re seeing the gap between where you are and where you could be. That gap is the entire reason we wrote the book.

Want a faster read on where you stand? We built a Creator Capitalist quiz on the website. Take it, get your results, and see how ready you are to make the shift. Take the quiz at creatorcapitalist.ai

Here’s what the waitlist at creatorcapitalist.ai gets you:

The free opening of the book—immediately. The Introduction and the start of Section 1, delivered to your inbox the moment you sign up. Start reading today.

Early ordering on March 16—a full day before the public launch. You’ll be reading and posting while everyone else is still finding out the book exists. The people who move first on launch day set the tone for the conversation. We want you to be one of them.

And if you want to go even deeper before the book drops—The Pirate Eddie Bot is the only AI on the planet trained on the Creator Capitalist framework, the Four Creator Capitals, Category Design, and 200+ Category Pirates mini-books. This thinking doesn’t exist anywhere else. Ask it about your Superpower. Challenge it on your Intellectual Capital. Let it push back on your blind spots. Start jamming on your capitals now so you’re three steps ahead while everyone else is still cracking the spine. Founding subscribers have full access.

Upgrade to the Founding Membership

Whether you take the quiz, go deep with the bot, or sit with the self-assessment above—do something with this before March 17.

The book gives you the complete system. The system works better when you don’t walk in cold.

Join the waitlist at creatorcapitalist.ai.

Arrrrrrr,

Category Pirates 🏴‍☠️

Eddie Yoon

Christopher Lochhead

This is a 🏴‍☠️ Founding Members–Only 🏴‍☠️ post. Founding Members get access to the Pirate Eddie Bot to ask category design questions, weekly actionable insights, the full library with 30+ audiobooks 2000+ mini-books, and more. See the Founders Deck here.

Subscribe now

Dear Friend, Subscriber, and Category Pirate,

Your best ideas are making someone else rich.

Not because you lack knowledge—the opposite, actually. You’re swimming in valuable, different knowledge. You’ve spent years learning your craft, developing a unique point of view, creating processes, solving problems, and achieving results.

The problem isn’t a lack of knowledge. It’s three mental traps:

“My knowledge is too specialized to scale.” It’s not. Every master was once a beginner looking for guidance. There are TikTok stars teaching quantum physics to teenagers.

“My work is too personal to systematize.” It’s not. Even the most bespoke services have underlying patterns. Therapists are building million-dollar online practices.

“I just know what works. I can’t explain how.” Not true. You just haven’t broken it down into learnable components. Fighter pilots break down split-second decisions into practical training.

These traps keep smart, experienced people stuck as Knowledge Workers—getting paid to apply what they know, instead of getting paid for what they create.

And here’s the part that should make you uncomfortable: every week you stay stuck in those traps, your knowledge inches closer to free.

AI is making existing knowledge and the ability to execute inside a system, process, or company closer to free every day. Roughly 70% of what most people got trained to do—memorize, respond, execute—AI can now do for close to free.

The value of your value got devalued.

Unless you turn it into something you own.

It’s the SAT problem.

Remember the SAT?

Reading, writing, and math—three completely different skills, one test.

Some people are great with words. Some people are great with numbers. Very few are great at both. And almost nobody can make it simple, clear and look good so it is easy to communicate.

The same thing is true for building Intellectual Capital.

That used to be a real barrier. If you wanted to go from Knowledge Worker to Creator Capitalist—if you wanted to take what you know and turn it into something you own—you needed a team.

Here’s what that looked like in the old world:

• An analyst to turn data into insights: $80–120K/year on average

• A writer or editor to turn insights into story: $50–80K/year on average

• A graphic designer to make it all look sharp: $45–60K/year on average

That’s potentially a quarter-million dollars in support staff before you’ve earned a dime from your ideas.

No wonder most Knowledge Workers stay Knowledge Workers.

That world is gone.

We just ran a Creator Capitalist Outcomes analysis—pulling together qualitative feedback from course alumni, converting it into quantitative patterns, and identifying 25 key transformations people experienced.

That’s consulting-team work. Two weeks. Tens of thousands of dollars.

We did it in a fraction of the time with Claude.

And this isn’t about AI as a generic buzzy concept. It’s about what Claude specifically does that collapses three barriers at once:

• Words → Numbers. It takes real human comments—messy, qualitative, unstructured—and converts them into structured, analyzable data. The kind of work you’d hand to a junior consultant and say “make sense of this.”

• Numbers → Words. It takes data and builds narrative around it. What does this number mean? Why does it matter? What do you do about it? That’s the What / So What / Now What framework in action. Genuine analytical thinking you can direct and refine.

• Makes both look good. Formatting. Design. Presentation. The stuff that makes people actually want to read, share, and act on your work. Like having a production team that never sleeps.

AI and the Creator Capitalist movement are happening at the same time because one enables the other.

The barrier between Knowledge Worker and Creator Capitalist just got radically smaller.

Good with words but not numbers? The gap closes. Good with numbers but can’t write? The gap closes. Have the ideas, but can’t make them look professional? The gap closes.

The old image of the solopreneur “wearing all the hats”—scrambling to do everything themselves, badly—is fading. Not because the hats went away. Because you finally have a co-pilot that’s genuinely good at the ones you’re not.

So here’s the uncomfortable question.

What is it costing you to wait?

Not in some abstract, motivational-poster sense. In real terms.

Every week you sit on an idea you haven’t published, someone else is publishing theirs. Every month you delay building intellectual capital, you’re paying the invisible tax of staying a Knowledge Worker—trading time for money, building someone else’s asset, watching your best insights evaporate inside a company Slack channel.

The tools are here. The playbook exists. The cost of entry just dropped by six figures.

A year ago, going from “I have an insight” to “I have a published, designed, data-backed piece of intellectual property” required a team, a budget, and a timeline. Today it requires a Claude account and a weekend.

The gap between “I should do this” and “I’m doing this” has never been smaller. Which means the opportunity cost of not doing it has never been higher.

There will never be a better time to become a Creator Capitalist than right now.

Not next quarter. Not when you “figure it out.” Not when you have more followers or a better title or a clearer niche. Right now—while the tools are new, the playbook is open, and most people are still frozen in the three mental traps we listed above.

The window where you can build a moat around your Intellectual Capital before everyone else catches on? That window is open today. It won’t be open forever.

That’s why we wrote Creator Capitalist.

694 pages. The entire transformation from Knowledge Worker to Creator Capitalist—how to discover your superpower, how to build the Four Capitals (financial, reputation, relationship, and intellectual) so they compound into each other, how to find the problem worth solving, and how to turn what you know into Intellectual Capital you own. Step by step. Frameworks, examples, and exercises you can use the day you read them.

This is the book that walks you through it. All of it.

And right now, 34 people are already reading it—weeks before anyone else on earth—as part of the Founding 50.

The Founding 50 is early access to Creator Capitalist, plus a front-row seat to our Lightning Strike.

We’re executing a coordinated book launch in public on March 17. The ad spend, the content calendar, the conversion numbers, the wins and the embarrassing failures—documented and shared as it happens. And we’re already posting learnings from the strike inside the community. Conversations are happening. People are sharing their own IC. The thing is live.

There are 16 spots left. The door closes tomorrow, February 26, at midnight PT.

Early access to Creator Capitalist is only available to our Founding Subscribers and Category Design Alumni. To sign up and become a Founding Subscriber, head here. Don’t want to join the inner circle? Join the waitlist and be the first in line on March 17th.

Total cost: $135. That’s the $100 Shopify bundle (hardcover + ebook + audiobook) plus the $35 Amazon paperback on Strike Day.

Step 1: Buy the $100 Shopify bundle now. The full ebook lands in your hands immediately. Hardcover arrives at your door in ~10 days. Audiobook drops before March 17.

Step 2: Buy the $35 Amazon paperback on March 17 (Strike Day).

Step 3: Join the war room sessions.

• March 6 (8–9am PT / 11am–12pm ET)—War Room #1. Full game plan reveal. Strike schedule, content calendar, ad strategy—everything on the table.

• March 13 (8–9am PT / 11am–12pm ET)—War Room #2. Pre-strike briefing. Final adjustments. The dress rehearsal.

• March 17—STRIKE DAY. Christopher on stage in San Diego. All 50 buy on Amazon. Reviews go up. Everyone posting on LinkedIn.

• March 20 (8–9am PT / 11am–12pm ET)—Debrief. The real numbers. What worked. What bombed.

16 spots. Early access ends tomorrow at midnight. Then the door shuts, and the war rooms start without you.

👉 Claim one of the 16 remaining spots and get your copy of Creator Capitalist here:

Read more

This is a 🏴‍☠️ Founding Members–Only 🏴‍☠️ post. Founding Members get access to the Pirate Eddie Bot to ask category design questions, weekly actionable insights, the full library with 30+ audiobooks 2000+ mini-books, and more. See the Founders Deck here.

Subscribe now

Dear Friend, Subscriber, and Category Pirate,

Creator Capitalist is the most important book we’ve published since Superconsumers and Play Bigger.

We don’t say that lightly. 682 pages. A year of podcasting, teaching, and writing about Creator Capitalism—all of it leading to this book.

And as of today, you can be one of the first people on earth to read it. Link to get your copy below. 🏴‍☠️

Early access to Creator Capitalist is only available to our Founding Subscribers and Category Design Alumni. To sign up and become a Founding Subscriber, head here. Don’t want to join the inner circle? Join the waitlist and be the first in line on March 17th.

Creator Capitalism matters more than ever right now.

AI has made existing knowledge and the ability to execute inside a system, process, or company closer to free every day.

You can’t out-execute AI. And yet that’s exactly what most people are trying to do—doubling down on the same skills that made them successful as knowledge workers: apply existing knowledge, execute inside existing systems, get paid for time.

It’s the completely wrong move. As Pirate Christopher says, the emphasis is on the wrong syll-able.

Roughly 70% of what we all got trained to do—memorize, respond, execute—AI can now do for close to free. And most people are responding to this by working harder at the thing that’s being devalued. Not because they’re stupid. Because it’s all they know. Because it invalidates their identity to admit the game changed.

This is the biggest shift in work in 70 years. Most people don’t see it. And the ones who do see it don’t know what to do about it.

Creator Capitalist is about what to do about it.

The book walks you through the entire transformation.

• How to discover your superpower—the thing only you can see and do.

• How to build the Four Capitals—financial, reputation, relationship, and intellectual—so they compound into each other.

• How to find the problem worth solving, the niche worth owning, and the business bandmates worth building with.

• How to use AI to scale your judgment instead of replace it.

• How to design a career where you get paid to be you—not for your time, not for your title, but for your different.

This is a book of frameworks you can use the day you read them.

Not “build a personal brand.” Not “start a side hustle.” Not the creator economy.

This book is about the shift from Knowledge Worker—where you got paid for what you knew and how fast you could execute—to Creator Capitalist, where you get paid for what you create, what only you can see, and how your different makes a difference for others. Where your ideas become the product. And you stop trading your precious time for money.

The book is done. And you can start reading it today.

This isn’t a pre-order or a waitlist.

You can buy the bundle and the full ebook lands in your hands immediately. Hardcover arrives at your door in about 10 days. Audiobook drops before March 17.

But the book isn’t the only reason we’re writing you today.

We’re executing a Lightning Strike on March 17—in public—and we’re bringing 50 of you inside the war room to watch it happen.

Last week we shared the full 16-week operating plan. The strike schedule, the ad strategy, the content calendar, the CFO guardrails. If you missed it, go read it.

This week, we’re opening the door. And you can join today.

We’re calling it the Founding 50.

We’re recruiting 50 Academy alumni and Founding subscribers to be the first people on earth to read Creator Capitalist—and to get a front-row seat to the entire launch as it happens.

This is the kind of behind-the-scenes, real-money, real-results campaign we’d normally package as a $5,000 course.

Your cost of entry? Buy the book.

$135 total. That’s the $100 Shopify bundle (hardcover + ebook + audiobook) plus the $35 Amazon paperback on strike day.

Here’s what you get:

• The full ebook, immediately. Buy the bundle and start reading today—before anyone else on earth.

• The hardcover + audiobook. Hardcover ships to your door. Audiobook drops before launch day.

• The actual strike playbook. The real document we’re working from—timeline, content calendar, ad strategy, targets. Not a summary.

• Three live war room sessions. Watch us walk through the game plan, share real-time results, and course-correct live.

• A full post-launch debrief with real numbers. What worked. What bombed. What we’d do differently.

• Access to our private community platform. Behind-the-scenes updates throughout the entire campaign.

Why only $135? Because we need you more than you need us. 50 verified Amazon reviews on March 17. 50 people in the LinkedIn comments leading up to strike day—sharing posts, commenting on launch content, posting about what you’re learning as you read. 50 people holding us accountable to execute every single thing we said we’d do.

You’re buying this book anyway. Might as well get the backstage pass.

Spots close February 26.

(If you’re not a Founding subscriber, you can join here and then head back to this post to join the Founding 50. Or join the waitlist for Creator Capitalist here.)

Join the Founding 50 and get your copy of the book here:

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This is a 🏴‍☠️ Founding Members–Only 🏴‍☠️ post. Founding Members get access to the Pirate Eddie Bot to ask category design questions, weekly actionable insights, the full library with 30+ audiobooks 2000+ mini-books, and more. See the Founders Deck here.

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Dear Friend, Subscriber, and Category Pirate,

We’ve spent the last five years telling you how to do things different.

$100 books. Category design. Intellectual Capital. Why Amazon ads are a casino. Why publishers take your money and give you nothing.

Now, it’s time to shut up and do it.

On March 17, our new book, Creator Capitalist, launches—and instead of quietly hoping the algorithm notices, we're doing our Lightning Strike for the book in public.

The decisions, the ad spend, the wins, the embarrassing failures—documented and shared as it happens.

Most launches are private because most launches are embarrassing.

When was the last time an author (or anyone) showed you their actual marketing plan?

Their ad spend?

Their conversion numbers?

Never.

Nobody wants you to see the math. Publishers don’t. Amazon doesn’t. Most authors don’t—because the math usually looks terrible.

We already showed you what happens when you run Amazon ads. We already showed you why the $100 book flips the math on paid marketing.

Now we’re showing you what it looks like to execute a coordinated launch using everything we’ve been teaching.

Welcome to our Lightning Strike for Creator Capitalist. And we want you inside the war room while we pull it off.

Here’s what we’re doing (you’re invited to join us.)

Two strikes. Two audiences. One bestseller. Sixteen weeks.

Strike 1 lands on March 17—the same day Pirate Christopher is on stage at a tech conference in San Diego. (That's not a coincidence.)

Strike 2 lands on April 16 at Military Creator Con in Dallas, to share category design and Creator Capitalist with our beloved veteran entrepreneurs.

Between now and then: 5x/week LinkedIn posts from both Pirate Christopher’s and Pirate Eddie’s profiles. 80–100 posts over four months. Paid ads funded only by revenue we’ve already earned. Claude Cowork building real-time dashboards and AI ghostwriters for both profiles.

Pirate Bri is leading the AI experiment. It might work. It might crash. When you join the Founding 50, you’ll see it either way.

We’re recruiting the Founding 50. The entry point is absurd.

We’re looking for 50 Academy alumni and Founding subscribers who want to help launch Creator Capitalist—and learn how to execute a Lightning Strike for their own book, course, or business.

We’re not handing you a graphic and asking you to “please share.” And we’re not starting another Discord that goes quiet after two weeks.

Here’s what the Founding 50 get:

• The ebook, immediately. Buy the Shopify bundle, and you get early access to the full Creator Capitalist ebook—all 682 pages—before anyone else on earth.

• The full strike playbook. The actual document we’re working from—timeline, content calendar, ad strategy, targets. Not a summary. The real thing, so you can study how a category-designed launch gets built and adapt it for your own.

• Zoom war rooms. Regular calls where we walk through the plan, share results, take your feedback, and course-correct together. Every session recorded so you can rewatch, take notes, and steal the playbook for your own launch.

• A community space to coordinate. A private space for the Founding 50 to hang out, see what’s being posted, know when to jump into comments, and talk shop. A backstage pass for the entire launch.

Total cost: $135.

That’s the $100 Shopify bundle (hardcover + ebook + audiobook) plus the $35 Amazon paperback on strike day.

$135 for a front-row seat to what we’d normally package as a $5,000+ course.

Here’s the thing: you’re buying this book anyway. So you may as well join the tailgate party and get the launch playbook at no extra cost.

We’re pricing it this way because we need you more than you need us. 50 verified Amazon reviews on March 17. 50 people in LinkedIn comments on strike day. 50 people holding us accountable to post every single day.

What we ask in return:

• Buy the $100 Shopify bundle to claim your spot in the Founding 50 next week.

• Buy the $35 Amazon paperback on March 17.

• Leave an honest Amazon review by March 24.

• Show up on LinkedIn. Jump into comments. Share a post when it hits.

• Attend the Zooms. Give honest feedback. Ask questions.

That’s the deal.

This is a Founding Members opportunity. If you’re not a Founding subscriber yet, this is about as clear a reason to join as we’ve ever given. The Founding 50 invitations go out next week—exclusively to Academy alumni and Founding Members. Between this, the Pirate Eddie Bot, the full mini-book library, and a front-row seat to every move we make over the next four months—you’re getting more than we should ever offer for $350.

👉 Become a Founding Member here.

This is the full 16-week operating plan for the Creator Capitalist Lightning Strike.

We’re sharing this for one reason: so you can steal it.

But first—a confession.

We outsourced this (almost). Talked to a marketing consultant with a solid track record launching books. Good guy. Knew the playbook. Problem was, his playbook was the same playbook every marketing consultant runs. Boost posts. Run ads. Hope for traction.

It wasn’t category designed.

A conventional launch treats the book as the product and marketing as a cost center. Spend money, get attention, pray the attention converts, hope you break even.

A category designed launch treats the launch itself as Intellectual Capital. Marketing generates revenue before the book ships. The audience isn’t buying—they’re participating. Content created during the launch becomes the next product. Every ad dollar is funded by dollars the launch already earned.

The launch doesn’t support the book. The launch, the book, and the course are the same thing—designed to compound into each other.

If you have something to launch—book, course, product—the structure below is yours to adapt.

One caveat. This plan will change. A good strike lets you move fast when reality shows up with better information than your spreadsheet. Post goes viral in week 3? Pour fuel on it. Ad test bombs in week 5? Pull the budget—don’t “give it more time” like the Amazon ads casino wants you to. We’ll document the pivots as carefully as we document the plan.

You’ll notice this plan is almost entirely LinkedIn.

No Twitter. No TikTok. No Instagram carousels. No “repurpose across 7 platforms.”

Simplicity is velocity. The consultant wanted us on 4+ platforms at once—which is how a small team gets spread thin enough to be mediocre everywhere. We’d rather be undeniable in one place than forgettable in five.

LinkedIn is where our Superconsumers live. It’s where the algorithm rewards consistency and conversation—two things we can control. All-in.

Let’s dive into our Lightning Strike plan. 🏴‍☠️

Week 1 — This week (Feb 10–15):

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This is a 🏴‍☠️ Founding Members–Only 🏴‍☠️ post. Founding Members get access to the Pirate Eddie Bot to ask category design questions, weekly actionable insights, the full library with 30+ audiobooks 2000+ mini-books, and more. See the Founders Deck here.

Subscribe now

Dear Friend, Subscriber, and Category Pirate,

We just kicked off our first-ever AI Clone Cohort—a small group of pirates building AI versions of themselves using the frameworks we’ve been developing with our own Pirate Eddie and Pirate Christopher bots.

We’re learning a ton. And we want to share what we’re figuring out in real time.

And the first thing we’ve learned?

Almost everyone is using AI wrong.

Not “wrong” as in they’re bad at technology. Wrong as in they’re obsessing over the wrong lever—and it’s costing them the one thing category designers can’t afford to waste.

Their differentiation.

Here’s what we mean:

We know a guy—smart guy, successful—who spent six months uploading documents into his ChatGPT. Hundreds of files. Training data. Transcripts. Frameworks. He was convinced this was why his AI was producing great results.

“You have to train it,” he told us. “Upload everything. The more context you give it, the better it gets.”

We think he may have been wrong.

AI wasn’t getting better because of his uploads. The underlying model was getting better the entire time he was “training” it. He attributed the improvement to his effort—when really, OpenAI was just shipping better software every few weeks.

This is the most common mistake people make with AI. They obsess over the context window and ignore the prompt. The context window is your content. The prompt is your thinking.

If you dump all your content into an AI with a generic prompt, you get generic output that sounds like everyone else.

You’ve just commoditized your own Intellectual Capital.

A category designer doesn’t use AI the way everyone else does—because category designers don’t think the way everyone else does.

The prompt is where your Point Of View lives.

It’s where your frameworks, your language, your different lens gets encoded into the machine.

Generic prompt = generic output = commodity.

Category-designed prompt = differentiated output = transformation.

After months of testing across Claude, ChatGPT, Gemini, Grok, and our own Pirate Eddie Bot—building AI clones, writing mini-books, designing categories, running a business—we’ve landed on something we haven’t seen anyone else say clearly.

There are four things that determine the quality of your AI output.

And almost everyone has the priority order backwards.

1. Model Quality—Which LLM are you using?

This matters more than anything else. Not all models are built the same—and they’re getting more specialized, not less.

ChatGPT has gone consumer. It’s optimized for the masses. Claude writes circles around it. Grok is built for real-time social data. Gemini is wired into Google’s ecosystem.

This is category design in action.

Each LLM is designing for a different use case—a different category of user. The question isn’t “which AI is best?” The question is “which AI is best for what I’m trying to do?“

You wouldn’t hire a tax accountant to design your brand—so why would you use a consumer-optimized chatbot to do deep strategic work?

2. Prompting—How you talk to AI.

This is the skill that holds its value. Models will change. Pricing will shift. Context windows will expand.

But your ability to give clear, structured, step-by-step instructions? That stays valuable no matter what else moves underneath you.

Here’s the difference:

A bad prompter barfs everything at AI in one giant paragraph and walks away. “Here’s everything I know. Figure it out.”

A good prompter does the same brain dump—gets everything out of their head first—but then adds the layer most people skip.

Direction.

“Here’s everything I know. Now here’s what I want you to do with it. Step by step. For this audience. In this format. In this tone. Toward this outcome.”

The brain dump is the raw material. The prompt is the blueprint. You need both. Most people only do the first part and wonder why the output feels like a B-minus book report.

Prompting is a skill. The people who are intentional about it get wildly better output than the people who aren’t.

Your prompt is how you teach AI to think like you.

Not like the internet. Not like a generic business consultant. Like the person who has spent years building Intellectual Capital in a specific category.

If you can’t articulate your thinking clearly enough to prompt an AI, you can’t articulate it clearly enough to sell it to a client, either. The prompt is a forcing function for clarity.

3. What You Pay—Free, $20, or $200?

This one’s a parabola, not a straight line.

Free is limiting. Twenty bucks a month unlocks a massive leap. But jumping to $200 doesn’t give you 10x more. It depends on your use case.

Pay enough to unlock the model you need. Don’t assume expensive means useful.

4. Context Window—What you upload.

Here’s where everyone gets it wrong.

The context window—how much information you feed AI—is also a parabola. Upload nothing, AI has no foundation. Upload everything? AI gets confused. It can’t prioritize. It doesn’t know what matters.

We learned this the hard way. We overloaded one of our bots with too much training data. The result? It got worse. It couldn’t find the signal in the noise.

Enough context is powerful. Too much is poison.

Think of it through the lens of the Four Creator Capitals. Your Intellectual Capital is your best content—your sharpest frameworks, your clearest POVs, your most battle-tested ideas. The context window should get your best Intellectual Capital, not all of it.

Curate, don’t dump.

So what does the right priority look like?

Pick the right model for the job. Learn to prompt well. Pay for what you need. And be surgical—not sloppy—with what you upload.

Now go use this.

Take the prompting principles from this post and go try them right now.

If you’re a Founding Member, you already have access to the Pirate Eddie Bot—an AI trained on 200+ Category Pirates mini-books, every framework, every POV, every piece of languaging we’ve built over the last three years.

Here’s a challenge:

Open up the Pirate Eddie Bot and prompt him using all five principles at once. Give him a role. Tell him who you are. Walk him through your problem step by step. Paste in an example of what “good” looks like for your business. Then compare that output to what you were getting before.

The difference will be obvious.

Some prompts worth trying today:

You are my category design strategist. I run [your business]. Help me identify whether I’m competing in an existing category or designing a new one. Here’s how I currently describe what I do: [paste your positioning]. Pressure test it.

I need to find my super geo. Here’s what I know about my best customers: [details]. Help me figure out where more of them are concentrated.

Here’s a piece of content I wrote. Help me write something similiar about [insert new topic]. Here’s what I currently think about it [insert your current POV]. 

The better you get at prompting, the more valuable the Pirate Eddie Bot (or any other LLM) becomes.

(Not a Founding Member yet? Founding includes unlimited access to the Pirate Eddie Bot, digital copies of all 6 of our big books, the conversation thread below, the entire Founder’s Deck, and more. Join as a Founding Member here. →)

Here’s How To Actually Become A Better Prompter

Most people treat prompting like Google search. Type a question. Hit enter. Hope for the best.

That’s not prompting. That’s wishing.

The people getting the best output from AI—the ones building businesses, writing books, designing categories with it—they treat prompting like a conversation with a very smart, very literal colleague who has zero context on your life.

Here are the principles that actually matter:

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Dear Friend, Subscriber, and Category Pirate,

We get this question all the time:

“How do I transfer category design to my team?”

It’s a reasonable question. You’ve read the mini-books. You’ve internalized the frameworks. You see the world differently now—and you want your team to see it too.

So what do most people do?

They drop a pile of reading assignments on their team’s desk. “Here, read these 20 mini-books. Then we’ll talk.”

And then nothing happens.

The problem isn’t your team. The problem is the approach.

Pirate Tom Schwab, founder of Interview Valet, ran into this exact wall.

He’s all in on category design. He wanted to teach it to his team. But he knew dumping a mountain of content on them wasn’t going to work.

So he tried something different.

He opened up the Pirate Eddie Bot—and started talking.

Not typing. Talking.

In about 30 minutes, Tom had a conversation with the Pirate Eddie Bot about who he was trying to teach, what he wanted them to learn, and what the end goal was. The Pirate Eddie Bot broke it down into a 3-month curriculum—what to focus on each month, each week, and which specific mini-books would have the biggest impact for his team.

30 minutes. A full training plan. Built by conversation.

Tom is now using that plan to execute and evangelize category design across his entire team.

You don’t transfer knowledge. You install thinking.

This is the distinction that changes everything.

When you give someone a stack of books, you’re asking them to do the synthesis work themselves. To connect the dots. To figure out what matters and what doesn’t. To translate theory into their specific context.

That’s a lot to ask—especially when they’re also doing their actual job.

Your team still needs to read. That’s how thinking changes.

But there’s a massive difference between “here’s 20 mini-books, good luck” and “here are the 3 mini-books that will shift how you see our business—read them in this order, and here’s what to focus on in each one.”

The first approach is overwhelming. The second is a path.

Your team doesn’t need to read everything. They need to read the right things, in the right order, for the right outcome.

That’s what the Pirate Eddie Bot helps you figure out.

It’s trained on every Category Pirates mini-book. Every framework. Every nuance. So when you have a conversation with it, you’re not guessing which content matters most—you’re getting a curated curriculum designed around your team, your business, and your goals.

Not sure what matters most for your team to learn?

Start there. Ask Eddie.

Tell him what your business does, where your team seems stuck, and what you’re trying to accomplish. He’ll help you figure out where the biggest gaps are and what will move the needle most.

When you implement this, here’s what changes:

You stop being the bottleneck.

Right now, every category decision runs through you. Every POV conversation. Every strategic call that requires someone to think different—it’s all waiting on you.

When your team thinks this way, they can move without you in the room. They can have conversations with customers you’re not part of—and nail the POV anyway. They can push back on “best practices” without needing you to give them permission.

You get people to jam with. People who speak the language. People who see what you see.

And the business?

It scales beyond your personal bandwidth. Your vision stops being stuck inside your head—and starts moving through your entire organization.

And the result?

You become the bottleneck for your own company’s growth. The thing you see so clearly can only move as fast as you can move. Your vision is stuck inside your head.

Tom figured this out. Now you can too.

Here are the 5 steps to build a category design training plan for your team:

Using the Pirate Eddie Bot.

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🏴‍☠️ REMINDER: We're hosting a live AMA with Pirate Jack (the Native Digital who built the Pirate Eddie Bot) TODAY at 10 am PT / 1 pm ET. If you want to build your own bot and learn the technical details that actually matter, get the details grab your spot here. Paid subscribers get free access.

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Dear Friend, Subscriber, and Category Pirate,

Here’s what nobody tells you about being CEO:

The job isn’t hard because you don’t know what to do. It’s hard because you can’t be everywhere at once. Your strategy is clear. Your priorities are obvious. But the business moves faster than you can clarify, and by the time you’ve explained the “why” to one team, three others have already drifted.

Legacy CEOs manage through hope.

Agentic CEOs manage through architecture.

We wrote The Agentic CEO to show you exactly how Category Designers are using AI to multiply the three areas that create the most leverage: Strategy, People, and Numbers. Not as a “productivity hack.” As a fundamental redesign of what the CEO role actually does.

If you haven’t read it, stop here. Read it first:

If you have read it, this post is your tactical guide.

We’re breaking down the five steps to turn your one-sentence strategy into executable logic that runs without you, and how to create your own User Manual. With the exact prompts. With real examples from CEOs who’ve done it. With the tactical moves that turn “I wish my team would get this” into “my agents enforce this automatically.”

Here’s what’s wild: The CEOs making this shift aren’t just moving faster.

They’re stepping back while the business accelerates.

Let’s show you how.

An AI agent is not a chatbot.

Or a fancy dashboard. Or a productivity tool bolted onto old workflows.

An AI agent is a persistent, goal-oriented, outcome-driven digital worker that can monitor signals continuously. Reason over context and constraints. Take or recommend action. Learn from feedback. Coordinate with other agents.

Think less of an assistant.

Think more about a co-founder executive who never sleeps, never forgets, and never gets political.

Agents don’t just answer questions. They do stuff. Produce actions and outcomes by themselves. They run loops. And CEOs who understand loops beat CEOs who stare at reports.

Agentic CEOs use AI to multiply the parts of the job that create the most leverage:

• Strategy

• People

• Numbers

This isn’t about automating tasks. It’s about amplifying judgment, insight, clarity, and alignment at a scale that was nearly impossible before.

Let’s break down each role and how AI becomes your multiplier.

Role 1: The Strategy Simplifier

Remember: Strategy is what you remove.

The fastest way to accelerate execution is to eliminate the decisions, projects, and conversations that slow everything down. Simplify until only the essential path remains. When strategy becomes obvious, motion becomes easy.

AI helps you simplify faster. Here are a few ways to start:

• Use AI to distill competing Languaging and POV into a one-sentence strategy.

• Run transcripts of leadership meetings through AI to spot themes, risks, and decisions.

• Offload repetitive explanations into an AI agent (like Delphi) that reinforces priorities across the company.

• Use AI tools to identify patterns and places where the strategy is drifting or where teams are working on things that don’t matter.

This is how strategy becomes a system. AI helps you clarify it, compress it, and repeat it until the organization runs on it.

• It forces prioritization—you piss off 9 to serve 1 Superconsumer.

• It creates autonomy—decisions happen without permission because the logic is encoded.

• It collapses ambiguity—what you do and don’t do becomes binary.

• It lets you move at speed under uncertainty because the strategy doesn’t require a meeting to execute.

• It aligns humans instantly because they’re not guessing what matters—the system already told them.

Pre-AI, this was already a superpower.

Post-AI?

It becomes executable logic. AI agents don’t need motivation. They need clarity.

The One-Sentence Strategy was never about memory. It was about autonomy.

And clarity is exactly what a One-Sentence Strategy provides.

Here’s an example Nike should have followed.

• Nike’s one-sentence strategy: “We serve athletes.”

  • Product Agent: Does this make an athlete measurably better?

  • Pricing Agent: Does this price exclude serious athletes for casual hype?

  • Marketing Agent: Does this storytelling prioritize lifestyle over performance?

  • Partnership Agent: Does this partner increase athlete credibility—or dilute it?

This is why Nike lost runners to Hoka.

They didn’t lose talent. They violated the sentence. Agents would have flagged it instantly.

Role 2: The People Multiplier

If people get wealthy with you, they’ll follow you anywhere.

Clint leads with clarity, not charisma. His User Manual removes interpersonal friction. His incentives reward outcomes. His standards create missionaries instead of employees.

Missionaries protect momentum because they’re committed to the mission.

AI builds alignment without micromanagement by helping you:

• Use leadership-mirror tools to spot blind spots you may not see in yourself.

• Use sentiment tracking to catch cultural drift before it becomes dysfunctional.

• Analyze communication patterns to see where trust is slipping or where tension is forming.

• Generate the first version of your User Manual by feeding AI your decisions, messages, pet peeves, expectations, and leadership patterns.

Owning the people becomes an engineering problem instead of an emotional guessing game.

You can use the AI prompt guide below to create your own User Manual.

Role 3: The Value Creator

CEOs who can’t explain the business can’t scale it.

A company’s market value grows when you understand what creates value, what destroys it, and what must be true for momentum to continue. Cash flow, unit economics, margin, and demand signals are navigation tools. You have to treat numbers as the business’s language.

When the math is simple and visible, decisions become obvious.

AI turns the numbers into a real-time guidance system.

• Create scenario models to see how pricing, hiring, or demand changes will impact cash flow

• Build cash flow agents that warn you when margins tighten or when customer behavior shifts

• Model financial futures using Monte Carlo simulations and understand your best-case, worst-case, and most-likely outcomes long before they materialize

Owning the numbers gives you confidence, and AI gives you confidence with far more precision.

The question is: how do you actually build this?

How do you turn your strategy into a system that runs without you?

How do you encode your judgment so agents can enforce tradeoffs in real-time?

How do you collapse months of alignment work into automated intelligence?

Below, we’re breaking down the exact five steps to build your Strategy Simplifier Agent—with the prompts, the logic, and the tactics that turn “I wish my team would get this” into “my agents enforce this automatically.”

We’ll give you the framework to build your Strategy Simplifer Agent and People Multiplier User Manual system.

If you’re a Founding Member, keep reading.

If you’re not, upgrade here to get access to the full tactical breakdown, the Pirate Eddie Bot to pressure-test your strategy and ask your category design questions, access to all 6 of our big books, and the weekly insights that help you build a legendary category.

How To Build Your Strategy Simplifier Agent: The 5-Step System

Here are five steps get started and build your Strategy Simplifier Agent:

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This is a 🏴‍☠️ Founding Members–Only 🏴‍☠️ post. Founding Members get access to the Pirate Eddie Bot to ask category design questions, weekly actionable insights, the full library with 20+ audiobooks 150+ mini-books, and more. See the Founders Deck here.

Subscribe now

Dear Friend, Subscriber, and Category Pirate,

Most people who want their own Pirate Eddie Bot aren’t chasing a shiny object.

They’re drowning in their own generosity.

They’ve spent years publishing their best thinking—posts, talks, decks, frameworks, half-formed ideas that became breakthroughs for other people. And now the problem isn’t “How do I create more?” It’s: How does anyone actually find, use, and benefit from what I’ve already given away?

That’s the quiet tax of being a missionary.

Your Superconsumers don’t want a scavenger hunt through your archives.

They don’t want to “start at the beginning” or read 47 posts to get one clear answer.

They want your thinking, synthesized for them, in the moment they’re stuck.

The Pirate Eddie Bot is not just a chatbot. It’s a personal librarian trained on a point of view. A way to turn a lifetime of generosity into clarity, leverage, and outcomes—without asking people to dig.

And when people see that working in the wild, they all ask the same question:

“How do I build this for myself?”

Almost everyone who wants to build their own Pirate Eddie Bot gets stuck in the same place.

When the work stops being conceptual and becomes technical.

You’ve read the mini-books. You can see the bot in your head. You know what you want it to do.

Then the real questions hit:

• Which files actually go in, and what format should they be in?

• What breaks when someone asks a weird question?

• Do I even have the time to figure this out?

Then you stall because turning ideas into a working system is a different skill entirely.

In 2025, we published Identity At Scale: How We Built The Pirate Eddie Bot, And How To Create Your Own.

In this mini-book, we shared a step-by-step look at how we built the Pirate Eddie Bot—and how anyone could build their own version using Delphi.

It became one of our top-performing mini-books and laid out the full instructions.

And still, to this day, one question shows up more than any other: “How do I actually build my own Pirate Eddie Bot?”

That question exists for one reason:

Jack Bigbee.

Pirate Jack is the Native Digital who built the Pirate Eddie Bot—and helped us build Lucy. He’s the person who translated our thinking, archives, and constraints into a working Delphi system.

He has been almost entirely exclusive to Category Pirates. He hasn’t taken on outside clients. He hasn’t taught this publicly.

Until now.

For the first time ever, we’re hosting an AMA with Jack.

(Keep reading to get access.)

If you’ve spent your career being radically generous with your thinking, this is for you.

If you’ve ever wished your ideas could work harder—without you working more—this is for you.

And if you’ve read Identity At Scale and thought, “Okay, now what?”—this is it.

In this live jam session, you can:

• ask Jack real questions about building a Delphi bot

• walk through the technical steps that actually matter

• understand where people get stuck—and why

You bring your questions.

Jack brings the experience of actually building these systems in the wild.

Together, we’ll jam on what it actually takes to turn your thinking into a working digital self.

This is where the playbook meets reality. Where the abstractions break. And where you leave knowing what to do next.

(If working with Jack has ever been on your mind, this AMA is the first step.)

Join us on January 14 at 10 am PT / 1 pm ET.

If you’re a paying subscriber—monthly, annual, or founding— you can attend for free (register at the link below.)

If you’re not, you have two options:

• become a subscriber to Category Pirates and get access to over 200+ mini-books and 25+ hours of category design conversations (and when you sign up for Founding, you’ll get access to the Pirate Eddie Bot).

• or grab a $50 AMA-only ticket

Get Your $50 AMA-Only Ticket

🏴‍☠️ Register for the AMA with Jack

Click the link below to register for the AMA and get the link to join:

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This is a 🏴‍☠️ Founding Members–Only 🏴‍☠️ post. Founding Members get access to the Pirate Eddie Bot to ask category design questions, weekly actionable insights, the full library with 20+ audiobooks 150+ mini-books, and more. See the Founders Deck here.

Subscribe now

Dear Friend, Subscriber, and Category Pirate,

Everyone is publishing the same year-end post right now.

LinkedIn is a wall of identical reflections—trend lists, lessons learned, tidy summaries that differ in wording but not in substance. They look thoughtful, responsible, and complete. They also quietly guarantee that next year will look an awful lot like this one.

Most people call this reflection.

We think that’s only half the job.

What matters is orientation.

Reflection asks, “What did I do?” Orientation asks, “Where am I standing—and is this position strong enough to break me out of the pack?” One creates a sense of closure; the other determines whether anything actually changes.

This is where breakthrough years are actually decided.

Not in trend predictions. Not in resolutions. But in whether you’re willing to reject the premise everyone else is accepting—and choose a different vantage point before the year even begins.

Everyone has goals for the new year.

Very few people ask the right questions.

If you want 2026 to be a breakthrough year, the three questions that matter most are below.

If you’re reading this and wondering whether you’re in the right room for a breakthrough year—this is the room we’ve been building for a long time.

Category Pirates didn’t start as a newsletter.

It started as a place for people doing smart work that wasn’t adding up—founders who weren’t confused about how to work harder, but about where to aim. People who sensed the problem wasn’t effort, but orientation.

The biggest breakthroughs don’t come from new tactics.

They come from a shift in vantage point—naming the real problem, rejecting the premise, and choosing a different position before the market forces one on you. Once that snaps into place, momentum follows naturally.

That’s why this has always been a thinking-first room.

We don’t chase trends here.

We don’t optimize for noise.

We slow things down just enough to help founders see what others miss—so they can move faster in the direction when it actually counts.

In 2025, we saw that orientation compound in a very real way.

One of the most meaningful experiments we ran this year was the Pirate Eddie Bot. What started as a way to help founders pressure-test their thinking quickly turned into one of the most effective things we’ve ever built—not because it gave answers, but because it asked better questions.

At the same time, we quietly launched the Founders side of the newsletter.

What happened surprised even us.

The conversations inside the Founders Deck were sharper. The outcomes coming out of Pirate Eddie Bot were clearer. And over and over, we saw the same pattern: when founders had a place to orient—and a thinking partner to jam with—momentum followed.

So as we look ahead to 2026, the move isn’t to invent something new.

It’s to double down on what worked.

Which is what brings us to the next experiment.

We’re actively building a Pirate Christopher Bot.

Not as a “tool.”

As a thinking partner trained on how Pirate Christopher actually helps pirates orient when the stakes are real.

No polite feedback. No surface-level suggestions. And yes—R-rated conversations.

As we build this next layer, we want your perspective in the room.

1. What would actually move the needle for you in 2026?

2. What do you want more of from us—and less of?

3. What kind of help from us would make the biggest difference right now?

Tell us in the comments what you want to see from us Pirates next.

If orientation is how you win the year, Creator Capitalists win the decade.

If there’s one thing we know for sure heading into 2026, it’s this: 2026 is the year of the Creator Capitalist.

Not creators chasing algorithms. Not founders grinding harder. But people who turn judgment, POV, and craft into assets that compound.

More people are realizing the real leverage isn’t attention—it’s ownership.

Not doing more work, but doing work that keeps paying you back.

If orientation decides whether a year breaks through, Creator Capitalism decides whether the work you do actually compounds.

It’s the difference between having a good year and building something that keeps working long after the year is over. The book is coming in March. The course relaunches in March too. (If you don’t want to wait, you can get started now.)

This is about choosing to be on the right side of a structural change.

If orientation helps you claim 2026, Creator Capitalism helps you claim the decade that follows.

Here’s what this all means for you:

We’re heading into 2026 with clarity about where we’re investing our time, energy, and best thinking.

Here’s how that shows up depending on how you’re sailing with us:

If you’re a free subscriber:

You’ll still get occasional free posts and previews to your inbox—and chances to jump into Pirate Eddie Bot promos and experiments when we open them up.

If you’re a monthly subscriber:

You’ll keep getting our Friday drops, including podcasts, mini-books, and the core Category Pirates thinking you’ve come to expect.

If you’re a Founding subscriber:

This is where we’re going all-in.

You get:

• Full access to the Pirate Eddie Bot

• Early access to the Pirate Christopher Bot as it comes online

• Our full audiobook library

• All five of our big books

• Wednesday Founder-only posts that break things down in a tactical, practical way

And more!

This is the inner circle—the room where we test ideas, pressure-test thinking, and turn POV into real outcomes.

If you’re an annual subscriber:

First, thank you.

If you’re on an annual plan, you’ve been some of our earliest and most loyal supporters. You backed Category Pirates before there was a Founders Deck, before Pirate Eddie Bot, before we fully understood what this community could become. That matters to us more than we’ve probably said out loud.

That clarity we’ve gained from the Pirate Eddie Bot is shaping our plans for 2026.

Looking ahead, we expect to move away from the annual plan and focus our energy on a single, all-access experience: the Founders Deck—where the work is more hands-on, more practical, and more connected to real outcomes.

If you’re reading this and thinking, “Wait… I supported you early—what does this mean for me?” that’s a fair question.

We don’t have all the details locked yet, but we do want you to know this: we care deeply about doing right by our annual subscribers, and we’re actively exploring thoughtful ways to welcome you into the Founders experience in a way that feels generous and intentional.

We’ll share more soon—before any changes take effect—and we’ll make sure there are no surprises.

For now, just know this: your support helped make everything that exists today possible. We’re genuinely grateful you’re here—and we can’t wait to help you unlock exponential outcomes in 2026 and beyond.

Three questions to category design your future in 2026

If you want 2026 to be a true breakout year—not just busier, louder, or more exhausting—these are the three questions that matter most.

(They’re the same questions we’ve been wrestling with behind the scenes as we plan our own 2026.)

Ponder them. Reflect on them as the year turns. Or jam on them with the Pirate Eddie Bot and see what your thinking reveals.

Read more

Dear Friend, Subscriber, and Category Pirate,

It’s Christmas Eve (Merry Christmas, Pirates 🏴‍☠️).

You love your family.

You really do.

You also wouldn’t mind 20–40 minutes where no one asks you a question, hands you a device to fix, wants your opinion on AI, politics, or whether this is “a good time to finally start something new.”

The holidays have a way of being loud—even when they’re warm.

Full of good intentions, overlapping conversations, and just enough chaos to make thinking quietly feel like a luxury.

That’s what long walks, empty kitchens, slow dishwashing, and headphones were invented for.

So we dropped a bunch of audiobooks to help you survive the holiday season—with your sanity (and curiosity) intact.

And instead of tossing 14 audiobooks at you randomly, we organized them by the kind of quest you might be on right now.

Because even a small pocket of momentum beats starting from zero in January—and this is a good week to protect it.

Pick one 3-book listening path.

Choose the path that matches the tension you’re feeling right now:

• Building A Business That Survives Reality

• Turning Thinking Into Leverage (Books As Assets)

• Designing the Game You’re Actually Playing

• From Teaching To Transformation

• Seeing Around Corners Before The Market Does

You don’t need to listen to all 14 (but you can if you want, or need, to 🏴‍☠️).

Start at the beginning and stop when something clicks.

Path 1: Building A Business That Survives Reality

This path is for when things feel a little tighter than the headlines admit.

When customers are more hesitant. When “growth” starts to feel fragile. When the question quietly shifts from “How do we scale?” to “How do we not break?”

This isn’t doom-and-gloom thinking.

It’s durability thinking.

These three audiobooks help you stop chasing demand, stop leaking value, and start building a business people won’t walk away from—no matter your age.

Solving For Churn: How Non-Obvious Bundles And Business Models Reduce Churn, Without Relying On Price

Churn isn’t a pricing problem. And it’s not a product problem either.

It’s a business model and value architecture problem.

This audiobook breaks down why modern customers binge, bail, and disappear—and how the smartest companies reduce churn by designing Non-Obvious bundles, deeper customer intimacy, and category-level loyalty instead of relying on discounts or feature wars.

You’ll learn why Serial Churners are the enemy of long-term value, why Supers are the only customers that really matter, and how to design offerings people don’t want to cancel—even when they’re tightening budgets.

Listen here:

How To Make Money In A Recession: 5 Steps To Create Demand For Your Product, Service, Or Platform

Recessions aren’t the worst time to build.

They’re the worst time to fight for demand—and the best time to create it.

This audiobook shows how downturns force buyers to redraw their “Must Have vs. Nice to Have” lists—and why category creators who understand this emerge stronger while competitors burn cash chasing shrinking attention.

Instead of reacting with discounts, this gives you a clear path to elevating what you do from optional to essential by reframing the problem you solve at the category level.

Listen here:

How To Build Your First (Crazy Profitable) Business As A Teenager: 18 Radical Ideas For 18-Year-Old Entrepreneurs And Younger.

Despite the title, this isn’t about age.

It’s about first-principles business thinking.

This audiobook strips business down to its rawest form: solving real problems, getting paid for outcomes, and building leverage without permission, capital, or credentials. It’s a reminder that the most resilient businesses aren’t built with complexity—they’re built with clarity, urgency, and scrappiness.

If you’ve over-engineered things or drifted too far from the fundamentals, this audiobook snaps your thinking back to what actually works.

Listen here:

Path 2: Turning Thinking Into Leverage (Books As Assets)

This path is for when you know you have something valuable in your head—but it’s not compounding yet.

You’ve written.

You’ve shared ideas.

You’ve shipped content.

But it still feels fragile. Like effort resets to zero every time you stop pushing.

This path reframes books not as creative output—but as economic infrastructure.
Not something you publish once, but something that keeps working for you.

These three audiobooks show how ideas scale, why most books fail to do so, and how to design intellectual capital that compounds instead of evaporates.

How To Become A Top 444 Author: Turn Your Breakthrough Ideas Into A Best-Selling Book

This audiobook comes from a Category Science study of the Top 444 best-selling business books of the last two decades.

Not advice.

Data.

It shows why some ideas scale and most don’t—and why writing “a good book” is very different from writing a book that creates leverage, authority, and long-term upside.

You’ll learn the difference between Author-Centric vs. Idea-Centric books, why category choice matters more than writing skill, and how the most successful authors ascend into larger, more durable categories where their ideas can actually travel.

Listen here:

Engineering A Best-Selling Business Book: Why some ideas scale and others do not.

This audiobook is about designing ideas that spread.

It breaks down the Obvious vs. Non-Obvious framework, why most books accidentally become commodities, and how language, framing, and category choice determine whether an idea sticks—or dies quietly on a shelf.

If you’ve ever wondered why some books change how people think while others are skimmed once and forgotten, this gives you the blueprint.

This is about engineering scale before you write a word.

Listen here:

The $100 Book: Why Book Economics Is Broken And How Authors Can Leverage Pricing To Increase The Value Of Their Intellectual Capital

This audiobook takes on a taboo question most creators never ask:

Why are books—one of the most powerful transformation tools in the world—priced like commodities?

Using real data, real publishing economics, and a live case study, this audiobook shows how pricing signals value, how underpricing destroys authority, and why the future belongs to creators who price for outcomes, not access.

It reframes a book as a declaration—not a discount—and shows how pricing can be the strike that creates a category of its own.

Listen here:

Path 3: Designing the Game You’re Actually Playing

This path is for when you’re doing everything “right” and still feel uneasy.

Revenue might be growing.

The product might be strong.

The team might be busy.

But underneath it all is a quieter question: Are we actually building something that wins long-term—or just competing well inside someone else’s game?

These three audiobooks help you step back, diagnose where you really stand, and see the category forces shaping your future before they shape it for you.

The Category Design Scorecard: How Do You Know When You’re Looking At A Category Creator Versus Just Another High-Growth Company?

This audiobook is a mirror.

It objectively shows whether you’re a company trying to Be the Winner, Be the Best, or Be Different—and why only one of those paths consistently creates outsized value.

Built from an analysis of Fortune’s fastest-growing companies, the scorecard walks you through five non-negotiable dimensions of category leadership: POV, future vision, radically different offers, data flywheels, and customer outcomes.

It removes ambiguity and wishful thinking. You don’t guess where you stand. You score it.

Listen here:

The Category Science Of Category Pirates: A Below-Deck Look At The Weird Data That Drives Our Decisions And Path Forward

This audiobook shows what happens when you stop relying on intuition—and start listening to weird data.

It’s a below-deck look at how Category Science works in the real world: how Superconsumer signals, behavioral patterns, and non-obvious data reveal where categories are actually headed.

More importantly, it teaches you how to run Category Science on your own business—so you can spot future demand, course-correct early, and avoid drifting into category neglect.

Listen here:

The Trillion-Dollar Future: How To Size Your Category Prize With Superconsumer AI Agents

Sizing the prize isn’t just math—it’s belief disguised as math.

This audiobook explains why spreadsheets alone consistently understate category opportunity, and how Superconsumers reveal how big the future can be if you’re willing to design for it.

Using Superconsumer AI Agents, this shows how to fuse belief, data, and imagination into a credible story of exponential growth—one that aligns teams, investors, and partners around a future worth committing to.

If you’ve ever felt your ambition outpaced your models, this closes the gap.

Listen here:

Path 4: From Teaching To Transformation

This path is for when information isn’t the problem anymore.

You’ve read the books.

You’ve watched the talks.

You know what “good strategy” sounds like.

This path is about crossing the line from knowing to becoming—from transferring ideas to creating outcomes that alter behavior, identity, and direction.

These three audiobooks reframe what learning, leadership, and leverage look like in an AI-first world—and why the future belongs to people who design transformation, not just content.

Transformational Books: Why $100 Books, Non-Obvious AI Bundles, & Category Design Are The Keys To Designing The New Business Book Category

Most books are built to be consumed.

Transformational books are built to be lived.

This audiobook exposes why the traditional publishing model undervalues both authors and readers—and how a new category of books is emerging that prices for outcomes, not pages.

It shows how $100 books, non-obvious bundles, and AI companions turn ideas into systems people return to, talk about, and act on. This isn’t about writing more. It’s about designing work that changes someone’s trajectory—and gets valued accordingly.

Listen here:

The Agentic Executive: Why The Future Of Work Is Managing AI Agents, Not Just People

The future of leadership isn’t managing people harder.

It’s orchestrating intelligence.

This audiobook explains why the managerial pyramid is collapsing and how executives who learn to command AI Agents will create exponentially more value than those who don’t.

It reframes “effectiveness” in an AI-first world—from activity and headcount to outcomes and leverage—and shows how leaders move from doing the work to designing systems that work for them.

Listen here:

Path 5: Seeing Around Corners Before the Market Does

This path is for when the present feels misleading.

The numbers still look fine.

The dashboards still update.

The experts still sound confident.

And yet, something feels off.

This path helps you spot category shifts while they’re still deniable—before they show up in earnings calls, headlines, or analyst notes. Not by guessing the future, but by learning how to read behavioral signals, generational shifts, and simplicity patterns that always precede market change.

The Next 10 Years For Netflix: How The Streaming Giant Can Create The Next Giant Film Category

This audiobook isn’t about Netflix.

It’s about how category leaders get blindsided when they confuse brand power with category power—and how new categories form at the edges of attention.

Using Netflix as a case study, it shows why gaming isn’t the next big opportunity, how creator-led content is reshaping entertainment, and why Native Digital behavior matters more than legacy media instincts.

It’s a masterclass in spotting where a dominant company’s assumptions no longer match reality—and what that teaches you about your own category.

Listen here:

The Digital Education Crisis: How Native Analog Teaching Is Failing Native Digital Students & The Massive Opportunity Ahead

This audiobook names one of the largest, slowest-moving category failures in plain sight.

It explains why Native Analog systems—built for memorization, credentials, and status—are failing Native Digital learners who live in a world of immediacy, creation, and outcomes.

More importantly, it shows how category neglect creates massive opportunity: when incumbents can’t adapt, new categories emerge. Education just happens to be early, obvious, and instructive for every other industry.

This is how you learn to see generational category shifts before they become irreversible.

Listen here:

Simplicity Is Velocity: Why Less Wins When Designing Your Category, Your Products, And Your Languaging

Complexity feels smart.

Simplicity wins.

This audiobook shows why simplicity isn’t a design preference—it’s a competitive advantage that accelerates decision-making, adoption, and growth.

Through examples across products, categories, and Languaging, it explains how leaders who simplify faster than competitors move ahead while others get stuck explaining themselves.

If you want to move quickly when the market shifts, this is how you cut through the noise and act decisively.

Listen here:

Our entire library of audiobooks is available to Founding Members. If you’re already a Founder, you’re set. Pick a path and press play. If you’re not, this is one of those moments where upgrading actually does what it says on the tin: it unlocks everything—including every audiobook you just read about, the Pirate Eddie Bot, our Founder Content library, and our entire library of 300+ publications. Upgrade here.

Five paths. Fourteen audiobooks. Zero obligation to listen to all of them.

This is your permission slip to take the long way around the block.

To “check on the dishes” for a little longer than necessary.

To put the headphones on, nod politely, and disappear into a better line of thinking for 20–40 minutes.

If you do listen to one, tell us which path you picked—and why—in the comments.
We’re always curious what quest Pirates are on.

However you’re spending the holiday, we hope it includes a little quiet, a little laughter, and at least one moment where your brain gets to stretch again.

Merry Christmas, Pirates 🏴‍☠️

Arrrrrrr,

Category Pirates

Eddie Yoon

Christopher Lochhead

P.S. - Our next book, Thinker’s High, is coming soon.

It’s 52 weekly provocations—one per week—designed to pull you out of default thinking, sharpen judgment, and remind you what it feels like to actually enjoy thinking again.

Stay tuned. 🎄🏴‍☠️

This is a FREE 🏴‍☠️ Founding Members–Only 🏴‍☠️ post. Founding Members get access to the Pirate Eddie Bot to ask category design questions, weekly actionable insights, the full library with 20+ audiobooks 150+ mini-books, and more. See the Founders Deck here.

Subscribe now

Dear Friend, Subscriber, and Category Pirate,

We were going to close the free Pirate Eddie Bot trial yesterday.

Instead, we’re extending it through the end of the week. That’s unusual for us as deadlines force decisions. Decisions force movement.

(If you already know you want to try the Pirate Eddie Bot, you can start here.)

Maybe AI feels intimidating. Or you’re skeptical that the Pirate Eddie Bot can generate outcomes. Like six figure outcomes for some of our Founding Tier pirates.

Keep reading.

This is the only free Founder post we’ve ever published.

We keep these behind the curtain for a reason.

Founder posts are where we do the implementation work of Category Design—walking through the tactical practical steps behind the ideas, showing how to apply them in real businesses, and often how to implement them with AI.

They’re written for people who aren’t just curious about Category Design, but are on a serious quest to design and dominate a new category.

But this week, we’re doing things different.

Because we went back to our Superconsumers. People who’ve used the Pirate Eddie Bot deeply as part of their real work. And we asked a simple question:

What outcomes did you get from the Pirate Eddie bot?

They weren’t just getting answers, like an AI librarian. They were getting accelerated transformation. In days.

Once we saw that clearly, keeping it private felt irresponsible.

Here’s a note we received yesterday from Pirate Rachel, who’s currently in her complimentary week of access:

“One session in and I’ve already reorganized my book chapters into a spine that actually makes sense. I know what each chapter gives the reader now. I’m also quickly learning how to talk to Eddie so he can help me organize my thinking—without writing for me.

Huge.”
—Rachel

That’s not about speed. That’s about structure. To help her create intellectual capital that will make her money while she’s sleeping.

The Permission Slip Problem

Everyone wants outcomes.

They think the missing ingredient is knowledge. They think maybe the Pirate Eddie bot can give them answers to their questions. They tell themselves, “I’ll be ready to act when I have the clarity to know what to do.”

But it’s just not a clarity or knowledge problem.

It is the problem that too many are waiting for a permission slip.

Pirate Eddie bot can answer your questions, providing the clarity and knowledge you need. But Pirate Eddie bot can also kick your a** with love and when needed.

That’s how transformation works.

Transformation starts the moment you take ownership of your thinking and actions.

People don’t describe the Pirate Eddie Bot as “useful.”

Yes, they describe it as a thinking partner. A guardrail. A co-founder. A mirror they didn’t know they needed.

But they also describe the Pirate Eddie Bot as a sparring partner. Because it refuses to let you off the hook.

• It doesn’t let you hide in optionality.

• It doesn’t reward you for being clever.

• It doesn’t let you outsource judgment.

• It keeps handing the work back to you.

Transformation doesn’t come from knowing more. It comes from taking responsibility for what you already know.

That’s the line most people never cross.

So they keep asking for answers—because answers feel safer than decisions.

Pirate Eddie Bot drives disciplined decisions and direction

Let’s talk about Pirate Nick.

Nick is the founder of ApricotLaw. Three years ago, his legacy category started dying. Revenue was contracting. He knew a pivot was coming, but couldn’t see clearly enough to move with conviction.

Nick didn’t use the Pirate Eddie Bot to “get ideas.”

He used it to discipline his thinking.

He ran his assumptions through it. He pressure-tested his category. He clarified his superconsumer. He locked a POV instead of endlessly iterating.

The result? In his words, not ours:

“The outcome so far is over $100,000 per year in recurring revenue. This is the very tip of the iceberg.”

Now, let’s be clear.

The Pirate Eddie Bot didn’t create the $100K.

It removed the fog that was preventing Nick from doing the work he already knew how to do.

That distinction matters.

The Pirate Eddie Bot did not:

• tell Nick what to sell

• write his offers

• generate magic copy

• promise him anything

What it did was more dangerous.

It forced him to stop drifting. It forced him to name the real problem. It forced him to choose.

That’s where the money came from.

And Nick wasn’t alone.

Pirate Eddie Bot accelerates Category Design

Pirate Lydia uses the Pirate Eddie Bot as a true thinking partner across category creation, GTM, and execution—building new categories while carrying real operational responsibility.

When we asked her what actually shifted, she didn’t hesitate:

“Eddie Bot helped me invent two new categories today—two AI companies I’m incredibly excited about. The Eddie Bot has been a big part of my success.”

What stood out wasn’t just ideation.

Lydia used the Pirate Eddie Bot to surface judgment gaps she’d missed—like ethical and explainability considerations inside a legal PRD she was drafting late at night.

She jams with the Pirate Eddie Bot whenever inspiration hits—sometimes at 4 a.m.—that always-on access mattered because category work doesn’t happen on a schedule.

She also used the Pirate Eddie Bot to help other people understand category design—clarifying POVs, explaining tradeoffs, and translating abstract ideas into language they could actually use.

And she’s very clear about the counterfactual.

“If the Pirate Eddie Bot didn’t exist, my first year as a solopreneur would’ve looked very different.”

Without it, Lydia would’ve spent far more time stitching together drafts alone, waiting on calendars to align, and manually assembling logic from our mini-books.

What changed was speed with standards.

Pirate Eddie Bot cuts your rework by 50%

Pirate Jennifer came to the Pirate Eddie Bot already moving fast—but paying for it in drift, rework, and second-guessing.

The cost wasn’t effort. It was sequence.

“I eliminated about six weeks of rework by using the Pirate Eddie Bot to stop drift and accelerated my category sequencing timeline by roughly 50% once Eddie Bot entered the picture.”

Before Eddie Bot, documents were rebuilt multiple times, sequencing was blurred, and outcomes arrived slower than they needed to.

What changed wasn’t effort or intelligence.

It was focus.

Pirate Eddie Bot Tells You the Brutal Truth

Pirate Sean came to the Pirate Eddie Bot wondering if his POV was truly differentiated.

It’s the quiet question almost every category builder carries—am I actually onto something, or just remixing what already exists?

“When I ask EddieBot, “Have you seen something like this before?” and the answer was essentially “Looks net new to me,” it gives me confidence we’re on the right track.”

That confirmation mattered because Sean wasn’t looking for encouragement.

He was looking for truth.

Pirate Eddie Bot helped Sean pressure‑test language, mental models, and the coherence of the category before launch—and even shape the Lightning Strike itself.

Sean put it this way:

“Category Pirates is a deep library of insight. Eddie Bot is the tool that distills it. It helps you navigate the concepts, connect ideas, and quickly surface the articles most relevant to your quest. It’s the closest thing to having Eddie sitting beside you while you build.”

Once you see it that way, the question quietly shifts.

If you’re already inside the Category Pirates library, why wouldn’t you be using the tool designed to help you think through it?

Pirate Paul came to the Pirate Eddie Bot in August, expecting help—but not honesty.

“I thought Eddie Bot’s response to something I shared was f**king brutal. Then I reread it and realized—it was exactly what I needed.”

That honesty turned vague thinking into structure: a clear POV, a villain, a three‑year plan, and a category worth committing to.

That’s when it clicked. This wasn’t a tool trying to please him.

It was a thinking partner willing to push back. Paul describes it as having permanent access to a world-class strategist—someone he could think out loud with, admit uncertainty to, and quickly turn raw ideas into structure.

And Pirate Eddie bot’s brutal truth and honesty might be higher than the real Pirate Eddie!

Six months earlier, Paul had vague ideas. Now he has the truth, which gave him clarity, momentum, and a plan he’s actually executing.

Pirate Eddie Bot is a confidant that gives confidence

Pirate Holley found that the Pirate Eddie Bot didn’t take responsibility away—it made her more confident carrying it.

She carries the weight of category design inside her firm—often alone, often under pressure.

“It’s been said before that being a category designer can be kind of lonely. While I have an amazing team, I’m really the growth architect and category designer for my firm. It can feel like a lot of responsibility.”

The Pirate Eddie Bot didn’t remove the weight of decisions. It made that weight easier to carry.

It acted as a counsel and sounding board—helping her think through category tradeoffs, client conversations, and board-level dynamics without drifting or second-guessing.

That mattered because category design isn’t just intellectually hard.

It’s emotionally heavy. And often lonely.

Pirate Eddie Bot gives constructive criticism

Pirate Don didn’t expect the Pirate Eddie Bot to push back when he was feeling unsure.

He went to it asking the real question: do I actually have something big here—or am I telling myself a nice story?

“Eddie Bot is a very good way to integrate Category Design thinking into the context of your business. Pirate Eddie Bot will tell me when it’s a good start but not good enough and how to make it legendary.”

What mattered most was that the Pirate Eddie Bot didn’t default to encouragement.

It pushed back, challenged the thinking. It helped him pressure-test the idea against real Category Design standards instead of vibes.

What Don found wasn’t certainty handed to him.

It was a way to wrestle unfinished ideas into something solid enough to commit to.

Across different industries, stages, and ambitions, the same pattern kept appearing.

People didn’t walk away saying:

“I got great answers.”

They walked away saying things like:

• “I stopped rebuilding the same document for the fifth time.”

• “I realized I was avoiding the hard decision.”

• “I can see the category now.”

That’s not information.

That’s an identity shift.

And identity shift is what makes outcomes compound.

If you’ve made it this far, Kit probably says it best.

“One of the guys I know (Pirate Eddie) has driven over $100M in growth strategies in his lifetime and uploaded his brain and voice into this AI. Why wouldn’t you want that at your fingertips?”

At this point, not trying it becomes the stranger choice (you can sign up for your free trial here).

So rather than leaving you to poke around randomly, we want to be explicit about how to use the next seven days—so you experience the same shift we’ve watched play out again and again.

By working the thinking the right way.

Seven Days To Your $100K Transformation

Let’s be clear about something up front.

Seven days isn’t enough to master this. And it’s definitely not enough to “finish” anything meaningful.

It is enough to start something most founders never do.

Over the next seven days, we’re going to give you a clear theme for each day—paired with a small set of prompts you can return to again and again.

Seven days won’t complete the journey. But it will make one thing very clear:

You’ve crossed a line.

Once that happens, you’ll understand why nobody serious ever wants to go back.

Day 1: Reject the premise

Most founders are just operating inside an unexamined assumption.

An assumption about:

• what business they’re really in

• what problem actually matters

• what customers truly care about

The danger isn’t bad thinking. The danger is confident thinking built on a false premise.

That’s why Day 1 is not about improving your ideas. It’s about questioning the frame those ideas sit inside.

If the premise is wrong, better execution only gets you to the wrong place faster.

Don’t come into Pirate Eddie Bot with polished language. Don’t try to sound smart. Dump your thinking as-is.

You’re not asking the Pirate Eddie Bot to fix anything yet. You’re asking it to challenge what you’re taking for granted.

Here are some prompts to start:

Prompt 1: Surface the hidden assumption

Here’s how I currently describe my business/category. What assumptions am I making that I’m treating as facts?

Prompt 2: Attack the ‘of course’ statements

What am I assuming customers already believe, understand, or agree with that might not actually be true?

Prompt 3: Test the frame itself

If this assumption turned out to be wrong, what part of my strategy would immediately break?

You’ve had a successful day one if you don’t feel “clear.”

You’ll feel:

• slightly uncomfortable

• less certain than you were yesterday

• aware that something you’ve been building on might not hold

Day 1 isn’t about answers.

It’s about creating enough doubt to make real thinking possible.

Day 2: Name the real problem

Symptoms are comfortable.

Problems are not.

Most founders are very good at describing what’s not working:

• leads are low

• sales cycles are long

• pricing feels hard

• customers don’t “get it”

Those are symptoms.

They’re downstream effects.

Pricing power, differentiation, and momentum only show up once the real problem is named clearly enough to confront—clearly enough that it makes people uncomfortable.

Day 2 is not about improving your solution.

It’s about naming the problem that makes your solution necessary.

If you get the problem wrong, everything else becomes noise.

You’re not asking Eddie Bot to help you sound better. You’re asking it to help you stop solving the wrong thing.

Prompt 1: Separate symptoms from the real problem

Here are the issues I keep running into with customers. Which of these are symptoms—and what problem might be causing them?

Prompt 2: Make the problem unavoidable

What problem, if solved, would make everything else easier—or irrelevant?

Prompt 3: Test the problem for category power

Is this a problem people already know they have—or one they don’t yet have language for?

You’ve had a successful Day 2 if:

• your problem statement feels sharper—but also heavier

• you realize you’ve been underplaying what’s actually at stake

• parts of your solution suddenly feel secondary

Day 2 isn’t about being clever.

It’s about naming the problem you’re willing to build a category around.

Day 3: Draw the line

Clarity requires exclusion.

Always.

Most founders think they have a positioning problem. What they really have is an avoidance problem.

They’re afraid to draw a hard line because:

• it feels risky

• it feels smaller

• it feels like saying “no” to opportunity

So they hedge.

And hedging is the fastest way to drift back into the existing market.

Day 3 is not about finding more customers.

It’s about deciding who this is not for—and being willing to live with that decision.

Until you draw a line, everything stays fuzzy.

On Day 3, you’re not asking Eddie Bot to help you grow faster. You’re asking it to help you stop trying to please everyone.

Prompt 1: Identify the wrong customer

Who keeps showing interest in my work but makes everything harder once they engage?

Prompt 2: Name the Superconsumer

Who does this work really well for—and why do they care more than everyone else?

Prompt 3: Test your willingness to exclude

If I fully committed to this Superconsumer, who would I have to stop trying to serve?

You’ve had a successful Day 3 if:

• your audience feels smaller—but clearer

• some opportunities suddenly feel like distractions

• your message gets simpler instead of broader

Day 3 isn’t about being exclusive for the sake of it.

It’s about choosing the people who make your category inevitable.

Day 4: Lock the POV

By now, you should feel tension.

You’ve questioned your assumptions. You’ve named the real problem. You’ve drawn a line around who this is for.

Day 4 is where most people instinctively soften—because locking a POV means being willing to be wrong in public.

A POV is not a positioning statement. It’s not messaging. It’s not a slogan.

A POV is a belief about the world you’re willing to organize your business around.

Day 4 is not about finding the perfect sentence. It’s about choosing the belief you’re willing to defend. Come in ready to be challenged.

You’re not asking Eddie Bot to make your POV sound nicer.

You’re asking it to pressure-test whether it can survive.

Prompt 1: State the belief plainly

Here’s what I believe about my category that most of the market doesn’t agree with yet.

Prompt 2: Attack your own POV

If someone strongly disagreed with this POV, where would they attack it first?

Prompt 3: Test your willingness to stand alone

If this POV costs me opportunities, which ones am I willing to lose?

You’ve had a successful Day 4 if:

• your POV feels simpler but riskier

• you’re slightly nervous to say it out loud

• parts of your old story no longer fit

That’s not recklessness.

That’s commitment.

Day 4 isn’t about being provocative.

It’s about choosing the belief you’re willing to build around—even if it costs you in the short term.

Day 5: Collapse the decision set

Day 5 is not about making better decisions.

It’s about making fewer decisions—on purpose.

We’re removing:

• Too many initiatives.

• Too many priorities.

• Too many “we could also…” conversations.

Every extra option becomes a hiding place.

Because momentum doesn’t come from choosing perfectly. It comes from choosing decisively.

Come in with everything you’re juggling.

You’re not asking Pirate Eddie Bot to help you optimize all of it. You’re asking it to help you discard the “maybe” paths.

Prompt 1: List the competing bets

Here are all the initiatives, ideas, or paths I’m currently trying to pursue. Which of these are competing with each other?

Prompt 2: Force the single bet

If I could only make progress on one thing for the next 90 days, which choice would unlock everything else?

Prompt 3: Remove the escape hatch

What option am I keeping around purely for emotional safety?

You’ve had a successful Day 5 if:

• your to-do list suddenly got shorter

• some ideas you liked no longer feel necessary

• your next week feels simpler, not busier

That’s not constraint for constraint’s sake.

That’s leverage.

Day 5 isn’t about being narrow forever.

It’s about choosing one direction long enough for momentum to show up.

Day 6: Make it real

Great thinking that only works in your head doesn’t work.

If your idea:

• needs explanation

• collapses when someone repeats it

• sounds smart but not actionable

It isn’t real yet.

Day 6 is not about polishing language.

It’s about making sure your thinking can travel—from you to someone else—without you in the room.

Categories don’t spread through decks. They spread through people.

Come in with the thing you think is clear.

Your POV. Your problem statement. Your category narrative.

You’re not asking Pirate Eddie Bot to rewrite it for you. You’re asking it to test whether it survives translation.

Prompt 1: The repeatability test

If a Superconsumer tried to explain this to a colleague, where would they stumble or get it wrong?

Prompt 2: Kill the insider language

What parts of this only make sense if you already agree with me?

Prompt 3: Translate to action

What decision should someone make differently after hearing this?

You’ve had a successful Day 6 if:

• your language got simpler, not duller

• your idea feels easier to say out loud

• you stop needing follow-up explanations

That’s not dumbing it down.

That’s making it usable.

Day 6 isn’t about sounding impressive.

It’s about making sure your thinking can move without you pushing it.

Day 7: Decide who you’re becoming

By now, something should feel different.

Not finished. Not solved. Different.

Day 7 is not about producing anything new. It’s about deciding who you are now that you can’t unsee what you’ve seen. The biggest trap after clarity is pretending nothing changed.

Come in reflective, not reactive.

You’re not asking Pirate Eddie Bot for the next move. You’re asking it to help you name the shift that already happened.

Prompt 1: Name the shift

Based on this week, how has my thinking changed—and where am I no longer willing to compromise?

Prompt 2: Close the old doors

What ways of working, thinking, or deciding am I no longer available for?

Prompt 3: Commit forward

If I act from this POV for the next 90 days, what becomes inevitable?

You’ve had a successful Day 7 if:

• you feel more grounded, not euphoric

• you’re less interested in advice

• you’re clearer about what not to do

That’s identity taking hold.

Day 7 isn’t the end of the work.

It’s the moment the work stops being optional.

And once that happens, the real question isn’t whether seven days was enough.

It’s whether you want to keep building alone—or keep building this way.

The Pirate Eddie Bot trial is now open through the end of December 21st.

No further extensions.

If you want to experience what judgment clarity actually feels like—not read about it—this is the simplest way to do that.

👉 Start your seven-day trial here

This post isn’t going anywhere.

You can come back to it every day. Use it as your launch pad. Or follow it step by step.

The seven days aren’t about rushing.

They’re about interrupting patterns.

Once you’ve seen what it feels like to think this way—to stop hiding behind answers and start making decisions—it’s very hard to unsee.

Arrrrrrr,

Category Pirates 🏴‍☠️

Eddie Yoon

Christopher Lochhead

P.S. - If this got your brain buzzing and you want to go deeper on using AI as a thinking partner (not a content machine)…

Then you might enjoy a few related mini-books from the Category Pirates library:

• The Pirate’s Guide To AI: How To Build With AI Like It’s The Greatest Co-Founder You’ve Ever Had [Part 1]

• Vibe Creating: Why Building With AI Starts With Being As Human As Possible

• Identity At Scale: How We Built The Pirate Eddie Bot, And How To Create Your Own

And if you want to actually practice that way of thinking (not just read about it), don’t forget to sign up for the Pirate Eddie Bot while the trial is still open.

Subscribe now

Dear Friend, Subscriber, and Category Pirate,

Every year, millions of people say they want to write a book.

Almost none of them do.

Not because they can’t write but because they don’t have a system that turns their ideas into something undeniable. Or they aren’t sure the juice is worth the squeeze.

The world is starving for books that actually transform people. Books that unlock outcomes. Books that hit with the force of a breakthrough. Books someone sees on their shelf and thinks, “That thing changed my life.”

Those are the books people proudly pay $100 for—because the value lives in the transformation, not the page count.

And you can write one.

We wondered if AI could write our books for us?

We tried to be an AI ghostwriter training it on all our content. We asked Lucy (our ChatGPT) to write the first draft.

It can’t.

It couldn’t write a book that matters, transforms, or becomes the dog-eared artifacts people return to for years. Writing the first draft of a transformational book is a tall task for any human writer too.

You can’t write a first draft about transformation unless you have lived it yourself.

You can’t just be a one-hit-wonder, but have unlocked transformations many times.

For you and for others.

We got a template, but templates can be thinking traps

Lucy was able to build us a mini-book template, reviewing our 200+ mini-books.

It seemed like a good idea at first. We were no longer looking at a blank page.

But templates turn off your brain. You default to monkey see, monkey do thinking. When you stop thinking, you stop writing with clarity and courage.

Our template became a thinking trap.

Don’t use AI for the first draft, but for first principles.

Once we stopped fantasizing about a magic ghostwriter, we discovered what AI can do. It remembers all the gems in the jam session that can be forgotten. It reflects your thinking back to you. It reveals gaps you didn’t know were there. AI helps you think about your thinking.

It collapses fog.

And when you combine an AI prompt stack for your thinking with a writing template, Substack, and a repeatable mini-book process?

Writing becomes inevitable. You stop trying to “be a writer.” You start becoming an architect.

The book that once felt impossible begins to assemble itself around you.

This year, something important happened on the pirate ship. Pirates started writing and releasing their own premium books. Pirate Paul Millerd did it. Pirate Chris is writing his version. Pirate Cole is writing his.

The water is warm.

Now it’s your turn.

Reject the premise of traditional book writing.

Wake up at 5 a.m. Lock yourself away. Drink black coffee and wrestle blank pages. Wait for inspiration. Pray for motivation.

Repeat.

Suffer.

But Pirates know better.

Writing isn’t discipline. Writing is a system. A system of thinking, writing and thinking

Once you have your system, writing stops being mystical or mysterious. It becomes procedural. The book that once felt distant becomes the obvious outcome of a deliberate process.

You don’t need a decade of discipline to write a powerful book.

You need a structure that does the heavy lifting for you.

You need a system that guides your thinking, sharpens your POV, and builds momentum with every step.

That’s what these 7 steps are designed to do and are the exact steps we use to write our books.

7 Steps To Start Writing Your $100 Book

Follow these to start writing your $100 book (even if you’ve never written a book before).

Here’s how to do it:

Read more

Subscribe now

Dear Friend, Subscriber, and Category Pirate,

Every self-publishing author has a moment when they look at their Amazon dashboard and ask, “Should I try running ads?”

It seems rational.

Amazon is the largest bookstore on earth. Ads theoretically boost visibility. And there are endless YouTube gurus claiming to “crack the code” with simple settings and a little patience.

When we launched Lightning Strike Marketing, we decided to test ads.

Pirate Eddie spent six weeks inside Amazon’s ad platform, running multiple campaigns, tracking spend, monitoring royalties, and doing the one thing every Category Designer in the world has to do:

Follow the money, and see if the story matches the math.

What follows is the high-level narrative you’ll want to understand before you ever consider running Amazon ads yourself. We share the gory details, the a-has, and the frustrations. By the end, you’ll know the strategic takeaways so you can quickly grasp the truth (from our point of view).

Let’s start with the thing we learned first, and the thing most authors never discover.

Surprise #1: You can’t measure what you earn.

The promise of Amazon ads rests on an illusion that you can spend $X and know whether it drove $Y in sales.

That isn’t true.

Pirate Eddie found three different “numbers” that claim to describe your book sales:

Read more

This is a 🏴‍☠️ Founding Members–Only 🏴‍☠️ post. Founding Members get access to the Pirate Eddie Bot to ask category design questions, the full Category Pirates library with 150+ mini-books, and more. See the Founders Deck here.

Dear Friend, Subscriber, and Category Pirate,

Most founders, creators, and entrepreneurs think they have a Point of View (POV).

But what they actually have is:

• A tagline

• A slogan

• A vibe

A category POV isn’t decoration, branding, or poetic word choice.

A POV is the operating system of a category.

It’s the set of beliefs that bends the world in your direction. It’s the story that makes demand chase you, instead of you chasing demand. It’s the lens through which people understand what the hell your “new and different thing” even is and why they should care.

This is why Category Designers obsess over POV.

Because POV is how you reject the premise, quit the old game, and create a new one.

In this post, you’ll see what it means to refine your POV. You’ll get an example of a Category Design Academy member working through the POV for his category. And you’ll also get several simple (and powerful) AI prompts you can use to collapse months of POV confusion into hours of clarity.

(If you haven’t read this mini-book yet, check it out before diving in.)

What Is A POV?

A POV is a belief system that includes:

1. The Non-Obvious problem you’re naming

2. The enemy causing the damage

3. The new future you’re evangelizing

4. The path that gets people there

5. The Languaging that makes all of the above sticky, repeatable, and spreadable

A POV is how you name the Existing Market Trap, reframe the game, redefine success, and give your Superconsumers a narrative they can repeat.

Most importantly, a POV makes the old world look obsolete.

Let’s look at an example.

Markham Rollins: Retirement Transformed

Markham and Jody Rollins have a clear mission: Help retirees design their second act.

But their earliest POV drafts lived in the head, not the gut:

“Retirement Drift is a collapse of rhythm, community, and purpose.”

That’s not wrong, it’s just a bit clinical. There’s no blood. No stakes. And no emotional voltage.

Then, Markham joined the Category Design Academy and started jamming with us. He explained his POV, and we pressure tested it. He jammed with AI, and we shared feedback.

Here’s where he landed:

“Retirement Drift isn’t a quirk. It’s theft. Rhythm collapses, friends thin out, and purpose leaks away until whole years blur into a beige fog. You wake up and think, ‘I’m not needed anymore.’ Days melt together. You feel guilty you’re not happier.”

Now that’s a POV.

Markham realized Retirement Drift isn’t passive. It’s decay engineered by a set of cultural lies:

• “Work was the problem.”

• “More free time will fix you.”

• “Slowing down equals healing.”

Those lies became the enemy that hits us with unavoidable stakes:

“Ignore it, and the slide accelerates. Bodies fray. Marriages hollow out. Curiosity calcifies. The person you promised you’d become after work never shows up.”

This is what happens when someone stops describing a market and starts creating a new one. Markham didn’t nail his POV on the first draft. He jammed with us in the Academy, and he jammed alone with AI by feeding it drafts, asking tough questions, and forcing it to sharpen the category Languaging.

He stopped forecasting a “better retirement.”

He started backcasting a different identity FROM “Retired” TO “Rediscovered Contributor.”

Just like:

• Airbnb moves people from Tourists to Live There travelers.

• Salesforce moves people from software owners to cloud operators.

• Markham and Jody move people from Retired to Rediscovered Contributors.

The category = the system.

The identity = the shift the system produces.

The a-ha: POVs don’t appear out of thin air.

POVs are designed.

The simplest way to create one is to use AI the way Category Designers do—as a co-founder that helps shape your thinking, refine your drafts, refine your Languaging, and design your future.

Now, it’s your turn.

10 AI Prompts To Sharpen Your POV

Whether you’re training your own AI Agent or using the Pirate Eddie bot, use these prompts when feeding it your POV drafts, transcripts, notes, and iterations.

These help the AI learn how you think, not just what you write.

1. Expose The Non-Obvious Problem

Read more