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Dear Friend, Subscriber, and Category Pirate,

Shelly Rood is Jane Bond.

Captain Shelly is a 16-year Army intelligence officer who spent her career doing one thing: reading situations most people couldn’t see, synthesizing what it meant, and briefing decision-makers on what to do about it.

She was exceptionally good at it.

She was also in the wrong place at the wrong time with the wrong people.

Just like Charlie Chaplin’s Little Tramp. Not the decorated hero walking a linear path. The lovable character who keeps ending up in the middle of someone else’s mess, getting arrested for a riot he was just standing near.

Pirate Shelly was very generous she was with her pain and Career and Life Quakes. She shared how her marriage to a fellow ROTC officer that unraveled into infidelity and abuse. The insecure male superiors who punished her for outperforming them.

So she pivoted.

She went to seminary. She became a chaplain. She built a course on moral injury. A community of 154 female veterans with 1,600 conversations in a single year. A bot, called Digital Shelly. A Substack. A second marriage she describes as life-changing.

What Shelly has done, without necessarily using this language until now, is category design her own life. She took a superpower the Army trained her for, named the problem nobody else was solving for female veterans, and built an entirely new category of support around it. A peer intelligence system, where women who’ve been through it brief the women who are currently in it. She named it. She framed it. She’s claiming it.

That is what a Creator Capitalist looks like. The woman veteran narrative has always been handed to someone else to write. Shelly became a category of one and picked up the pen herself.

Here’s how to navigate this conversation:

• 05:05 – Jane Bond and the bunker in South Korea: What a tactical all-source intelligence officer actually does, and why Shelly’s version of the job was cooler than most.

• 08:18 – The Little Tramp: Why Shelly Rood is Charlie Chaplin’s character, not the decorated straight-line hero, and why that framing is more honest and more useful.

• 10:21 – Detroit rooftops and the freshman 15: How she ended up in ROTC, a sorority, and the rifle team all at the same time.

• 15:16 – Institutional betrayal: The sorority incident that made her choose the uniform over the Greek letters.

• 17:20 – Sharing of partners: Christopher asks her to repeat herself. She does.

• 22:18 – Ten years and a son: The marriage, the infidelity, the drinking, the divorce. And what it looked like from inside a military community where that behavior was normalized.

• 31:51 – Accused of forgery. Accused of plagiarism. Failed grenade training: The pattern of being punished for competence, and the five years of hard thinking it took to understand why.

• 38:56 – The news director who couldn’t finish the phrase: Shelly’s television career, the insecure boss, and Eddie on what it costs to be right versus what it costs to keep your job.

• 43:10 – Moral injury: The concept that’s only been named in the last decade, why the only path through it is understanding the why, and why Charlie Chaplin’s audience always understands what the Tramp doesn’t.

• 47:16 – Who takes care of the women: Shelly on the woman veteran narrative, what’s wrong with how it’s currently told, and what she wants to write instead.

To connect with Shelly:

• Follow Shelly on LinkedIn

• Listen to the Hardcore and At Ease Podcast

• Check out Mission Ambition

Arrrrrr,

Category Pirates 🏴‍☠️

Eddie Yoon

Christopher Lochhead

P.S.—Shelly is a living example of what happens when someone takes their lived experience, names the problem only they are positioned to solve, and builds a category around it.

If you’re ready to do the same, the Academy 4.0 is where that work gets done. If you’ve been watching from the sidelines wondering whether the Academy is the right next move for you, Shelly’s story is probably the most honest answer we could give.

→ Learn more about the Academy here.

→ Apply 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.

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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 →]

Arrrrr! 🏴‍☠️ Welcome to a 🔒 subscriber-only edition 🔒 of Category Pirates. Each week, we share radically different ideas to help you design new and different categories. For more: Audiobooks | Category design 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,

Captain Shelly Rood’s job was to know things that other people didn’t.

As a tactical all-source intelligence officer in the United States Army, she ran teams of analysts across multiple intelligence disciplines:

• Image intelligence

• Human intelligence

• Signals intelligence

• “I could tell you, but I’d have to hurt you” intelligence

Captain Shelly’s job was to take the raw data flowing in from every source and synthesize it into a coherent picture. She’d brief the decision-maker with the clearest, most accurate reading of reality she could construct.

What was happening? So what does it mean? Now what do we do?

In every intel brief, an area will exist called ‘analyst note,’ and that’s where the true expert gets to share their read on the situation to the decision maker, possibly in an attempt to sway the briefing outcome. Analysts’ notes are the “hears what that means” portion of the briefing.

She briefed full-bird colonels, one-star to three-star generals. She gave intel briefings ten stories underground in a bunker in South Korea. She led covert briefings overseas and ran security programs for 4,000 soldiers.

Captain Shelly was exceptionally good at reading situations.

We could all use an intelligence officer for our lives.

Especially when we face life quakes.

What’s a life quake?

Let’s ask Bruce Feiler, the Category King of Life Quakes.

Pirate Bruce spent years crisscrossing America collecting hundreds of life stories for what he called the Life Story Project. He coded those stories for dozens of variables and published his findings in Life Is in the Transitions.

His core discovery: we experience a disruption (a meaningful life change) every 12 to 18 months. Most of those we navigate with relative ease. But about one in ten becomes what Feiler calls a “lifequake”.

A massive, forceful burst of change that leads to a period of upheaval, transition, and renewal.

His research found that the average person goes through three to five of these in their adult life, and the average transition takes about five years.

Do the math.

That means we spend roughly half our adult lives in an unsettled state. Feiler identified 52 distinct types of disruptors across five categories (body, love, work, identity, and beliefs) and found that the transitions they trigger don’t follow the neat, linear stages that a century of psychology promised us. Life, he argued, is nonlinear.

And the transitions that reshape life are nonlinear, too.

Captain Shelly was no stranger to life quakes.

• She married her ROTC sweetheart right out of college.

• Endured infidelity, excess drinking, and abuse/violence.

• She divorced her ex-husband when her son was four.

But she also endured Career Quakes.

• Targeted by insecure male superiors who saw her competence as a threat.

• Falsely accused of plagiarism because her intel work was “too good”.

• The chain of command that often put inferior leaders above her.

Every time she outperformed a weak boss, she got punished for it.

Make no mistake, Captain Shelly is no pushover.

She was captain of the rifle team. The best shot in her unit. A five-foot fireball who won awards for feats of strength in her sorority, before she chose the uniform over the Greek letters. Distinguished Military Graduate at WMU.

She grew up swinging hammers on rooftops in Detroit for her grandfather’s construction company—a third-generation business at Seven Mile and Van Dyke, the same neighborhood where 8 Mile was filmed.

Don’t mess with Captain Shelly.

How did she respond to these life and career quakes?

She became her own intelligence analyst.

• She left the military

• She went to seminary.

• She became a chaplain.

• She built a course on intimate partner violence.

• She built a series of cohorts to help female military vets.

• She built intellectual property on 8 “Wildflower” profiles of female veterans.

• She just launched her own Substack and created the Pirate Shelly AI bot!

Captain Shelly became a Creator Capitalist.

Today, Shelly is remarried.

She has two more children. She says she’s the best she’s ever been. She’s a chaplain, a podcast host, a broadcast television executive, the founder of a community called Others Over Self with 154 members and 1,600 conversations in 2025 alone, and the creator of the state’s official Woman Veteran Peer Support Program in Michigan, going nationwide. She teaches courses on moral injury and intimate partner violence based on lived experience.

Pirate Shelly is a successful business owner and federal contractor getting ready to celebrate the ten year mark.

The problem she is solving is that the military has more Iron Man (playboy, rule breakers) than Captain Americas (ethical and physically strong). That leaves many women veterans without a narrative of their own.

Her Superpower is exactly what it always was.

She just does it now for a different mission.

She reads situations, synthesizes data, constructs narratives, and briefs decision-makers. But this time, she is briefing the military women who disproportionately are the caretakers of aging parents, struggling friends and more. Because if we take care of these military women, everyone wins.

This mini-book is about how to use AI to have your own Career Intelligence Officer as you navigate Career Quakes.

Because career quakes are coming.

For some of you, they’re already here. AI is the biggest quake in a generation. It might be the biggest quake ever.

Entire categories, industries, and societies are being reshaped. Companies are restructuring. Re-starting with AI as their co-founder.

And somewhere in your life, a personal quake is going to collide with all of it.

We speak with more experience on this than we’d like.

The question isn’t whether you’ll face career quakes. You will. The question is whether you’ll be wise enough to let them build you.

Shelly was. Here’s how.

P.S. Quakes create the most growth. Because they force you to grow.

The Three Rings to Rule Them All

Your career doesn’t exist in a vacuum.

It sits at the center of three concentric rings. Each one is capable of remaking your life (or wrecking it) in ways you never saw coming.

• Ring one: Global quakes. What happens around us matters. War, economic shifts, and rising inflation on the price of carbondigulators. We are not alone in the world.

• Ring two: Organizational quakes. Who runs the company? Who controls the budget? Who gets into the meeting? Whoever decides if you’re in or out?

• Ring three: Personal quakes. Your relationships. Your sense of purpose. The stuff the therapist asks about.

Most career advice picks one ring and pretends the other two don’t exist.

The business books obsess over global change. As if knowing a trend is coming makes you ready for it.

The leadership books obsess over promotions and organizational chess. As if climbing the ladder matters. Especially a ladder learning on the status quo building, which is already on fire.

The self-help books obsess over purpose and connection. As if your inner life is separate from the category quake happening around you.

The rings don’t move independently.

They interact. They amplify each other. They collide.

And the interaction effects (the place where category transformation meets organizational chaos meets personal upheaval, at the same time), that’s where people get built.

Or crushed.

Especially if they were only watching one ring.

Let’s go deeper.

Ring 1: Global Quakes

Seven world quakes you will face.

These are forces you can’t control and didn’t choose. They can cascade downward. A pandemic triggers remote work, which reshapes capital flows, which rocks industries, and which forces your company to restructure.

One quake.

Seven layers deep.

1. Geopolitical: Wars, pandemics, geopolitical change.

2. Demographic: Birth rates, aging populations, migration shifts.

3. Technology: Steam engine. Assembly line. Internet. AI.

4. Economy: Recessions, booms, interest rates, and capital markets.

5. Regulatory: One law, one signature, one ruling.

6. Industry: Category violence and Category Design.

7. Cultural: Social movements, generational value shifts, the zeitgeist.

To say nothing about the potential impact of meteors, aliens, or your weird neighbor Jim.

Each of the 7 quakes in the global ring can be a tailwind or a headwind.

These are not forces you can overpower, outmaneuver, or outrun. But you do have the power to choose your lens. To reframe your perception of them entirely.

Many legendary breakthroughs are forged in crisis.

Ring 2: Organizational Quakes

Seven category quakes reshaping work, and what they’re doing to you.

These happen inside the walls of your professional life. They’re more personal than global quakes but still largely done TO you by the organization, the boss, or the structure you’re operating in.

Or at least that’s how it can feel.

But just like the global quakes, a green and positive quake isn’t always a blessing. A red and negative quake isn’t always a burden.

1. Promotion: Too fast and you’re in over your head. Too slow and resentment breeds.

2. Compensation: More money isn’t always a blessing. Less money always stings. How you get paid shapes the outcomes that build your reputation capital.

3. Leadership: A great boss accelerates your career by a decade. A terrible one sets it back farther.

4. Role & Responsibility: Too much authority without clarity sets you up to fail. Wrong-fit jobs can turn a career you love into dread.

5. Transition: The lateral move. The industry jump. The step down you take to eventually go up. The step back to become a parent.

6. Change in Control: Merger, acquisition, IPO, bankruptcy. Life-changing wealth or wipeout, decided above your pay grade.

7. Betrayal & Blessing: You’ll be stolen from and screwed over. You’ll also receive credit you didn’t fully earn. Be prepared for both.

Ring 3: Personal Quakes

Seven quakes life does to you.

“Life is fired at us point-blank.” -José Ortega y Gasset

These are the original lifequakes (the legendary) Bruce Feiler studied—and they belong in any honest career framework. Because the idea that your career exists separately from your life is one of the most damaging lies the professional world tells.

1. Love: Your spouse is the highest-ROI career decision you’ll ever make. Divorce is experienced as something close to death.

2. Children: Having them changes every calculation. Not having them is its own quake. Children can multiply the highs and lows of your career.

3. Family: The unexpected phone call or the slow march of caregiving hugely impacts your career. Family can be the sanctuary from the storm.

4. Health: The wealth of health is almost always taken for granted. Until it is slowly or suddenly taken away.

5. Peace & Violence: Peace isn’t the absence of conflict. It’s the foundation you stand on for everything. If evil violently attacks you or someone you love, you will experience a seminal before/after in your life. Violence (or fear of it) changes everything. Peace changes everything, too.

6. Relationships: Humans need each other desperately. The right people are worth more than any credential. The wrong ones are deadly to your soul.

7. Purpose: You hit the goal, get the title, and feel not-so-satisfied. Or purpose finds you. And doesn’t let go. Work can be a means or an end in itself.

Pirate zebra whole:

When work shifts…

• FROM: being the thing you do.

• TO: the thing you were designed to do and only you can uniquely do.

You win.

And the world wins too.

Seven Core Truths About Quakes

Here is what we believe to be true—based on our own careers, on the data, on the hundreds of career stories we’ve studied, and on the three military stories in this book.

#1: You can’t stop quakes.

Read more

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Dear Friend, Subscriber, and Category Pirate,

Last week, the same day Creator Capitalist launched, Pirate Christopher gave a keynote in San Diego. He built the entire speech around what happens when knowledge and execution become free, and creation becomes the only thing that matters.

He closed with something that won’t leave people’s heads:

“If you connect your different to making the biggest possible difference at scale with AI, you will have a different career. If not, you’ll suffer the fate of a knowledge worker.”

There’s no third option.

He’s given many a monster keynote.

But this was different. Multiple men and women came up to ask if they could just hug him. He clearly struck a chord.

The decades old Knowledge Worker deal is done

For 67 years, the Knowledge Worker deal was simple: acquire valuable knowledge, get paid to apply it. Knowledge is power. Execution is everything.

You were raised on that deal. You were rewarded for it. Promotions, titles, salaries—all of it is designed to keep you applying existing knowledge to existing problems. The system told you that knowing and executing were valuable things. And you believed it, because the paychecks confirmed it.

Creating—the thing every five-year-old does without thinking—got relegated to the margins. To the weekend. To the “when I have time” pile. The thing that used to come naturally became the thing you needed permission for.

Now knowledge is free. Execution is free. And creating—having a point of view, naming a problem nobody else has named, building a framework that didn’t exist before, designing something so different that people reorganize their thinking around it—is the only thing that’s scarce.

The irony is brutal: the thing the system trained out of you is the only thing the market will pay for now.

A five-year-old creates naturally. A fifty-five-year-old has been trained out of it.

Get a few kids together. Give them paper and crayons. Leave the room for 20 minutes.

They’ll draw. They’ll invent. They’ll argue about whose drawing is better. They’ll make up stories about what they drew. They’ll collaborate, compete, and create—without anyone telling them to. Without a framework. Without permission. Without a strategy meeting first.

Every five-year-old is insanely creative. They won’t shut up. They’re full of ideas. They have more curiosity in a single afternoon than most boardrooms generate in a quarter.

So you’d think by the time they’re 55, with decades of experience and knowledge layered on top of that natural creativity, they’d be the most creative people alive.

The opposite happens.

Somewhere between five and fifty-five, we got trained to stop creating and start executing. To stop asking “what if?” and start asking “what’s the deliverable?” To stop seeing what isn’t there yet and start optimizing what already is.

The system rewarded us for it. Promotions, titles, salaries, corner offices—all of it designed to keep us applying existing knowledge to existing problems inside existing structures.

AI just made that entire reward system obsolete. The executing and the knowing—the things the system trained us to prioritize over creating—are now the cheapest things on the planet.

The creating—the thing every five-year-old does without thinking—is now the most valuable.

This is either terrifying or the greatest opportunity of your life.

It depends entirely on whether you have a framework for it.

If you’re still trying to outsmart AI by knowing more, or outwork AI by executing harder, you’re going to lose. You’re playing the 67-year-old game with 67-year-old rules, and the rules just changed.

If instead you connect your different—your superpower, the thing people come to you for, the thing that makes the biggest difference possible—to making a difference at scale with AI, everything changes.

One person can now build what used to take an entire company. The Silicon Valley conversation has moved from “when will we see the first billion-dollar one-person company?” to “when will we see the first billion-dollar ARR one-person company?”

The tools are here. The moment is here. The question isn’t whether AI will replace you.

The question is: what should you create?

Three things to sit with before Friday.

1. When was the last time you created something that didn’t exist before?

Not edited. Not optimized. Not iterated on someone else’s work. Actually created—from scratch—a framework, an idea, a point of view that was yours. If you can’t remember, that’s the signal. The system trained the creating out of you. It’s still in there. But you have to go looking for it.

2. What do people come to you for that you’ve never charged for?

The thing colleagues ask you about in the hallway. The thing friends text you about on weekends. The thing you do so naturally that it feels like it shouldn’t count as expertise. That’s your superpower. And it’s probably the most valuable thing about you—precisely because you’ve never treated it that way.

3. If you could only do one thing for the rest of your career, what would it be?

Not the thing you’re good at. Not the thing on your resume. The thing that—if everything else went away and you could only keep one piece of what you do—you would choose. That’s where the creating lives. That’s what AI can’t replicate. And that’s the foundation of everything a Creator Capitalist builds on.

Write your answers down. Don’t type them. Don’t ask AI. Sit with them.

Friday: Career Quakes drops.

AI is the biggest career quake in a generation. Maybe the biggest ever.

We keep using that word—quake—because it’s precise. Not a disruption. Not a trend. Not a “shift in the landscape.” A quake. The kind that shakes all three rings of your life simultaneously: the global forces you can’t control, the organizational forces reshaping your workplace, and the personal forces that decide whether you break or build.

Most career advice picks one ring and pretends the other two don’t exist. The business books obsess over global disruption. The leadership books obsess over promotions. The self-help books obsess over purpose. None of them talk about what happens when all three rings go red at the same time.

On Friday, we’re releasing a new mini-book called Career Quakes. It’s about the moments that shake your career—and the framework for using them to build instead of break.

Career Quakes is a paid publication. More on how to access it below.

If you’re ready to become a Creator Capitalist through this quake—not just read about it—the Creator Capitalist course closes Friday.

Everything in this email—the five-year-old who stopped creating, the 67-year-old Knowledge Worker deal that just expired, the question of what you should create next—the Creator Capitalist Course is the system for answering it.

Your superpower. Your Four Capitals. Your offer ladder. Your pricing. Framework by framework, with AI tools built into every step. The course includes the $100 Complete Collection of the book (hardcover, ebook, audiobook) plus three guided modules.

119 people went through this course last year. They uncovered $425M in quantified outcomes they didn’t know they had.

The course closes Friday, March 27 at midnight. We haven’t opened it in over a year. We don’t know when we’ll open it again.

This is the week to go all in on being a Creator Capitalist.

Get the Course + Book

Already bought the book and want to upgrade? Email hello@categorypirates.com with your receipt for a discount code.

Not ready for the course? Join the inner circle.

If you want to start jamming on these ideas with the thinking partner that makes them personal—and get access to everything we publish, including Career Quakes on Friday—the Founding Membership is the way in.

Founding members get:

• The Pirate Eddie Bot—the only AI trained on Category Design and Creator Capitalism

• 30+ audiobooks

• Free copies of our six full-sized books (A Marketer’s Guide to Category Design, The 22 Laws of Category Design, The Category Design Toolkit, Snow Leopard, Thinker’s High, and Lightning Strike Marketing)

• Invites to founder-only virtual workshops (held two to three times a year)

• The Category Vault and the full 250+ mini-book library

Become a Founding Member

Arrrrrr,

Category Pirates 🏴‍☠️

Eddie Yoon

Christopher Lochhead

P.S. — Not ready for the course or Founding? Get the book:

• Paperback on Amazon — $35

• Ebook — $35 (instant access)

• Audiobook — $35 (instant access)

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

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Dear Friend, Subscriber, and Category Pirate,

Lydia Flocchini is a lawyer who decided the law wasn’t enough.

Nick Kringas is a restaurateur, SEO pioneer, and serial category designer.

Together, they walked into a legal tech conference with a $24,000 budget, a two-week runway, and a question that stopped attorneys cold: Are you AI invisible?

They left with a signed client with $90,000 in revenue, 15 warm prospects, and a pipeline trajectory toward $300,000 to $1,000,000 in annual recurring revenue.

That’s a lightning strike. And it's exactly what a Creator Capitalist looks like in action.

If you read Lightning Strike Legends, you already know their receipts. This conversation is where you hear them tell it themselves—and where the story gets a lot more interesting.

The value of a business bandmate.

We borrowed these words from a LinkedIn post by Pirate Lydia

Most people build careers. Very few find their business bandmate.

One of the most important and rare things in business is finding someone you’re meant to build with. Not just collaborate. Not just partner. But someone who sees the world the way you do and challenges you to see it differently.

I found my bandmate through the Category Design Academy. I still remember when Pirate Eddie Yoon said, “Lydia, you need to meet Nick Kringas. He’s also in legal.”

What began as a few conversations quickly turned into a shared point of view.

We talked about the shifts reshaping hashtag#legal -AI, private equity, generational change, and how marketing and business development are evolving in an AI-driven world. We call this the 𝗔𝗜 𝗩𝗶𝘀𝗶𝗯𝗶𝗹𝗶𝘁𝘆 𝗥𝗲𝘀𝗲𝘁.

Then Nick told me he was rebranding his company and asked me to help. The timeline was tight. He knew I had led rebrands before. I said yes.

From there, we got to work- building, collaborating, and sharing ideas leading up to the PILMMA's AI for PI Expo and beyond.

And somewhere along the way we formed a partnership with a shared mission and purpose to help law firms navigate the market siege.

I'm excited to share that Nick and I are now featured in 𝗖𝗿𝗲𝗮𝘁𝗼𝗿 𝗖𝗮𝗽𝗶𝘁𝗮𝗹𝗶𝘀𝘁, 𝗖𝗵𝗮𝗽𝘁𝗲𝗿 𝟭𝟰: 𝗙𝗶𝗻𝗱 𝗬𝗼𝘂𝗿 𝗕𝗮𝗻𝗱𝗺𝗮𝘁𝗲𝘀.

“This is the story of how two solo pirates became bandmates—and why finding your bandmates might be the most important decision you make as a creator capitalist.”

This isn’t just our story. It’s about orchestrating a lightning strike, one of the most valuable skills you can learn as a creator capitalist.

𝗪𝗵𝗮𝘁 𝘀𝗵𝗼𝘂𝗹𝗱 𝘆𝗼𝘂 𝗹𝗼𝗼𝗸 𝗳𝗼𝗿 𝗶𝗻 𝗮 𝗯𝗮𝗻𝗱𝗺𝗮𝘁𝗲?

1. Shared language: We think in category design. We don’t follow markets, we create them.

2. Shared experience: First-generation. Children of immigrants. Shaped by the American Dream. That gives you resilience and a lens rooted in possibility.

3. Deep expertise: Nearly 50 years combined in legal. Millions in outcomes. Your intellectual and reputational capital are your leverage.

4. Challenge each other: A bandmate sharpens your thinking. We challenge ourselves all the time to think differently and reject the premise.

5. No ego: You elevate each other. Always.

6. Shared mission: We want to help the injured and the attorneys who serve them. Belief and conviction in your mission are everything.

We’ve also been fortunate to learn from Eddie Yoon and Christopher Lochhead 🇺🇸🇮🇱🏴‍☠️,true bandmates we admire and aspire to.

I’m incredibly grateful to be on this journey with Nick, and part of a community that pushes me to think bigger and grow.

Your bandmate might be in our Pirate Ship

Lydia joined the second cohort. Nick joined the third. Eddie connected them. They started talking about the legal industry from opposite coasts—Lydia in Silicon Valley watching AI ads on every billboard, Nick in New York, talking to personal injury lawyers still measuring success in a different kind of billboard.

Same industry. Same category design lens. Complimentary superpowers.

What the Academy gave them individually was just as important as the introduction. Lydia said it plainly: it wasn’t just category designing her business. It was category designing her—who she wanted to be in this next chapter. Nick said that after joining the Academy, he started waking up in the middle of the night with ideas he couldn’t turn off.

That’s what deep thinking does when you’re surrounded by people doing the same.

Then Nick mentioned a conference. Two weeks away. Lydia said yes before she’d thought it through.

What you don’t get in the mini-book is the moment Nick knew he’d found his person. He’d been going back and forth with Lydia for days—him thinking about the long game, her pulling him back to earth with pipeline math. Then she showed him a languaging framework she’d built from weeks of their conversations, texts, and Slack messages. He had a tear in his eye. He called it a masterpiece.

That’s called Relationship Capital.

That lead to Intellectual Capital.

“Are you AI invisible?”

That’s the problem they named, framed, and claimed.

Law firms have spent years and fortunes on SEO. What Nick and Lydia discovered in their data: among the 80 law firms they analyzed, the ones that invested most heavily in SEO had a median AI visibility score of zero. The correlation between SEO authority and AI visibility?

0.076.

AI doesn’t respond to the same signals SEO does. The playbook that made you visible to Google actively makes you invisible to AI.

Every personal injury attorney who woke up at night worrying about where their next case would come from just got a new reason to worry—and a new category of solution to buy.

The minute the lawyers at the conference started using the words back at them—“wait, am I AI invisible?”—Nick and Lydia had already won the framing and naming game.

This is what the four Creator Capitals look like when they compound. Intellectual capital—a problem nobody had named. Reputation capital—two people already known in the space. Relationship capital—a bandmate found inside the Academy. Financial capital—a $24,000 bet with a 12x return. You don’t stumble into that. You build it. (And the book walks you through it.)

If their story resonates with you…

It’s in the book. The lightning strike playbook. The bandmate framework. What it means to be a creator capitalist who owns what they create instead of renting out their expertise to someone else’s company.

Creator Capitalist is out now. Nick and Lydia’s full story is one of the featured case studies. If reading this makes you think that could be me—that’s exactly who we wrote it for.

Get the book here: creatorcapitalist.ai/

Here’s how to navigate this conversation:

• 00:00 – When the student is ready: Lydia’s Odyssey from maritime law to legal tech to the Academy—and why timing is everything.

• 10:59 – Nick’s superpower revealed: How 30,000-foot market thinking showed up in a Greek restaurant before he ever heard the words “category design.”

• 16:54 – The bar, the restaurant, and the borrowed $139,000: Nick’s origin story as an intuitive category designer—and why losing the bar shaped how he sees the world.

• 24:22 – How they found each other: Two different cohorts, opposite coasts, one industry, and an introduction from Eddie.

• 33:05 – From advisor to bandmate: How the partnership formed faster than either expected—and why the moment Nick read Lydia’s languaging framework, he had a tear in his eye.

• 41:09 – The lightning strike: Two weeks, $24,000, a corner booth, and “Are you AI invisible?”

• 47:05 – When they parroted the words back: The moment Nick and Lydia knew they’d won the framing and naming game.

• 55:52 – The first client paid for the strike: The ROI math on a category-designed lightning strike.

• 1:01:00 – The data that changes everything: 80 law firms, a 0.076 correlation, and why heavy SEO investment predicts AI invisibility.

• 1:09:37 – “The AI you use today will be the worst AI you use”: Christopher on the compounding returns of AI as a thinking partner.

• 1:15:07 – Finding yourself before finding your bandmate: Why the individual work in the Academy made the partnership possible—and why Lydia wouldn’t let Nick touch the flag.

This is what Creator Capitalism looks like in practice.

Not a side hustle. Not a consulting arrangement. A category, a co-creator, a lightning strike, and a business that didn’t exist 90 days ago generating six-figure recurring revenue.

Nick and Lydia are the case study. Creator Capitalist is the playbook. The course is where you do the work.

Creator Capitalist is available now—and the course closes March 27th. If you’ve been waiting for proof that this is real, you just read it.

→ Get the book and join the course here.

Arrrrrr,

Category Pirates 🏴‍☠️

Eddie Yoon

Christopher Lochhead

P.S.—Nick and Lydia didn’t stumble into this.

They did the work—the Academy, the individual thinking, the willingness to plant a flag in a category nobody had named yet. Their bandmate was sitting in a different cohort. Their category was sitting in an industry everyone else had written off as change-resistant.

Our current cohort is graduating soon. The next one starts in May. If you’ve been watching from the sidelines wondering whether the Academy is the right next move for you, Nick and Lydia’s story is probably the most honest answer we could give.

→ Join the waitlist here.

And if you’re not ready for the Academy yet—start with the book. Creator Capitalist is available now. The course closes March 27th.

→ Buy the book and join the course 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

Dear Friend, Subscriber, and Category Pirate,

The whole world is asking the same question right now: what’s the future of work?

And the answers everywhere are the same. Doomsday panic or empty optimism. Learn AI. Upskill. Pivot. Adapt. Hustle harder. None of it names what actually comes after the Knowledge Worker era ends. None of it proposes a system.

Three years ago, we started working on one.

What comes after the Knowledge Worker? How do I stop building someone else’s category—and start getting paid to be me?

Today, we publish the answer.

Creator Capitalist is live.

694 pages. Three years in the making. The complete system for designing a career where you own what you create—and your different makes dollars.

This book took longer than we planned. That used to frustrate us. Now we’re glad. Because if we had just shipped it, Creator Capitalist would have been a book. Instead, it became a category. And over the course of a year, a movement.

We did primary research with 1,000 US adults. We interviewed hundreds of professionals. We produced dozens of podcasts. We built a course and ran it for a year with 119 people. We wrote dozens of mini-books. We got help from legendary people who gave us their time, their thinking, and their stories.

Somewhere along the way we realized: this isn’t our book. It never was.

It belongs to anyone who refuses to be turned into a replaceable Knowledge Worker. Anyone who knows—deep down—they’re here to create, not comply.

Free people, free people. That’s the game now.

Get the book

This isn’t a typical book purchase. Creator Capitalist is built to be a career transformation—not a weekend read. It’s available as a single format, a complete collection, or bundled with the full course. Pick the one that matches how ready you are to make the shift.

• $100 — The Complete Collection: Audiobook and ebook available immediately. Hardcover (shipped to you). All three formats. The full 694-page system.

• $35 versions

  • $35 Paperback on Amazon

  • $35 Ebook (instant access)

  • $35 Audiobook (instant access)

Get Your Copy at creatorcapitalist.ai

And when you buy the book this week, you get the Mount Rushmore Outcomes Analysis for free (see more below).

The course is open—for the first time in a year. It closes March 27.

We haven’t opened enrollment in the Creator Capitalist Course since last year’s R&D cohort. 119 people went through it. They generated $425 million in quantified outcomes. We took everything we learned, rewrote the book around it, and rebuilt the course from the ground up.

Today it’s open again. On March 27, it closes.

The Creator Capitalist Course — $500

The course includes everything in the $100 Complete Collection—hardcover shipped to you, audiobook and ebook available immediately—plus three modules with AI-powered exercises:

• Module 1: Position Yourself — discover your superpower, write your POV statement, make yourself different (not just better)

• Module 2: Plan for Success — audit your Four Creator Capitals, build your financial runway, design a life that funds freedom

• Module 3: Get Paid To Be You — build your Good / Better / Best offer ladder with pricing examples, turn your knowledge into income

The book gives you the system. The course walks you through implementing it—with guided exercises, AI tools, and the frameworks built into every step.

If you want the full experience, this is it. And it won’t be available again until we decide to reopen it.

Get the Course + Book

Want to add the Founding Subscription? Bundle it for $250 (normally $350—save $100). You’ll get Founding-tier access to Category Pirates on Substack, including The Pirate Eddie Bot, the Category Vault, and the full mini-book library. You’ll receive instructions via email after purchase. Available only to our Creator Capitalist Course members.

GET THE COURSE + BOOK — enrollment closes March 27.

Launch-week bonus: Buy before March 20

Everyone who buys Creator Capitalist this week—any format, any price point—gets the Book Rushmore Outcomes Analysis free.

$425 million in quantified outcomes from 119 Creator Capitalists. 25 trap-to-transformation stories. Category science on what actually drives results. The kind of analysis a consulting firm would charge five figures for.

Buy on creatorcapitalist.ai and we’ll send it automatically. Buy on Amazon and email hello@categorypirates.com with the subject line “CC Book Rushmore” and we’ll send you the PDF.

Available until March 20, 2026.

If you’ve been jamming with us—whether you’re in the Founding 50, an Academy alum, a subscriber, or someone who’s been circling this idea for months—you didn’t just support a book. You helped build a category.

We are Creator Capitalists.

And today, the movement gets loud.

Join the movement

Arrrrrrr,

Category Pirates

Eddie Yoon

Christopher Lochhead

Arrrrr! 🏴‍☠️ Welcome to a 🔒 subscriber-only edition 🔒 of Category Pirates. Each week, we share radically different ideas to help you design new and different categories. For more: Audiobooks | Category design podcast | Books | Sign up for a Founding subscription to ask the Pirate Eddie Bot your category design questions.

Subscribe now

Dear Friend, Subscriber, and Category Pirate,

Lightning Strike Legends is a new mini-book series.

We will share outcomes of real pirates executing real strikes and getting real receipts.

This first one belongs to Pirates Lydia Flocchini and Nick Kringas. Two Category Design Academy alumni. Different cohorts and different coasts. Children of immigrants who know what hardship looks like and aren’t afraid of it.

Both are proven Creator Capitalists.

The strike you’re about to read didn’t work because they followed a marketing playbook. It worked because they’d already built the Creator Capitalist foundation underneath it. The capitals came first. The revenue followed.

Pirates Lydia and Nick each have an abundance of the Four Capitals: Reputation Capital, Relationship Capital, Financial Capital, and, most importantly, Intellectual Capital.

• Pirate Lydia can take any legal tech sales funnel and grow it using magic words.

• Pirate Nick sees new categories everywhere and knows how to create them.

• They have both created massive economic outcomes for others.

If you’d like to read more about them, you’ll have to turn to page 619 of our Creator Capitalist book! Or listen to the Creator Capitalist podcast we did with them next week.

Now they are creating massive economic outcomes for themselves too.

Here’s what they did. They planned a Lightning Strike in three weeks, invested $24,000, signed a $90,000 recurring client on Day 2, generated $270,000 likely to close, and had a total potential pipeline of up to $1,000,000!

4x ROI before they caught their flights home. 11x near-term potential ROI with a near 42x ROI in the total pipeline.

We’re not just bragging about Pirates Nick and Lydia (though we are.)

We are trying to shake the unbelief out of you.

However, some don’t like having their beliefs challenged. You can see it in some of the negative reviews for our Lightning Strike Marketing book.

For the record, we love negative reviews.

They are informative if you read them correctly.

These folks are disappointed about what they learned. But Lightning Strike Marketing is not a teaching book. It’s a Transformation book. The context of a Teaching book is a classroom. The context of a Transformation book is getting into the arena and slaying dragons.

The purpose of the book is to get you to take action and make it rain revenue.

Do You Believe There is Buried Treasure?

We are trying to tell you there is buried treasure right in front of you.

But you can’t get the treasure by just reading a book.

Outcomes require action.

This is like the joke of the two economists walking on the sidewalk. One says, “Look, there’s a $100 bill in front of us.” The other says, “That’s impossible. If a $100 bill was actually there, someone else would have picked it up.” And they walk right past it.

Our favorite quote in the negative review is “They have the audacity to sell it for $100.”

But what happens when a $100 book results in $90,000 in real revenue on Day 2 of the strike? And another $270,000 in near-term pipeline has the potential upside to $1,000,000?

Is it audacious? We think it is audacious and generous.

More than one thing can be true.

Creator Capitalist launches March 17. If you want to start mapping your own buried treasure before the book drops—join the waitlist at creatorcapitalist.ai. You’ll get the Introduction and Section 1 opener immediately.

We don’t care nearly as much about bad reviews of a book as a bad review about yourself, your superpowers, and the potential upside of the new category you’ve been sitting on.

That’s what we’re trying to help you believe.

Creator Capitalists unlock massive economic abundance.

Lightning Strikes produce real revenue.

You just need to pick it up.

Just like Nick and Lydia.

Proven Creator Capitalists Join Forces

Nick Kringas is the oldest son of a Greek immigrant who built a bar near a General Motors plant and lost it.

Nick was caddying that summer when his mom called, crying. We lost the bar. He was the oldest child. He began negotiating a forbearance with the mortgage company before leaving for college.

Like many children of immigrants, Nick had to become a Pirate early on.

He borrowed $139,000 against his parents’ house to open an authentic Greek restaurant. His mom is in the kitchen. His dad is out front. Family style, run-out-of-food-three-days-in-a-row successful.

Pirate Nick was an intuitive Category Designer.

The market figured out that following Pirate Nick was a good idea. Competition has copied Nick everywhere he’s gone.

As other ‘authentic Greek’ restaurants followed, Pirate Nick taught himself SEO from a home study course. He pivoted and built an agency for personal injury law firms, grew it fast, and watched it commoditize.

That’s when he found Play Bigger.

Lydia Flocchini is the oldest daughter of immigrant parents.

Twenty-six years in legal tech. She is a lawyer by training and also a category designer by instinct. She led marketing for Thomson Reuters’ flagship legal research product when they were the Category King. Then she caught the startup bug and joined Lex Machina to invent legal analytics from scratch, which was later acquired by LexisNexis.

She kept building, kept scaling, and kept delivering for everyone around her.

Then she stopped.

Not because things were going badly, but because Pirate Lydia realized everyone else was benefiting from her superpower, but she hadn’t fully capitalized on it as a Creator Capitalist.

Pirates Lydia and Nick are not just exceptional because they’re talented.

They’re exceptional because they’ve both spent their lives carrying weight that not everyone has to carry. The burden of not just providing for themselves, but for parents who sacrificed everything to give them a shot, for families who depended on them to get it right.

This is also known as the American Dream.

That kind of pressure doesn’t break people like Nick and Lydia.

Here’s what most people miss when they hear stories like Nick’s and Lydia’s: you think they had something you don’t. They didn’t. They had the same thing you have—years of Intellectual Capital trapped inside other people’s businesses, Reputation Capital locked inside institutions, Relationship Capital they’d never activated, and Financial Capital they’d never structured for investment. The difference is that they finally saw it. Creator Capitalist exists to help you see yours.

The only thing they were missing was each other.

They met inside the Category Design Academy. Different cohorts on different coasts. Pirate Eddie connected them, seeing two people working in the legal space from opposite ends of the country, whose superpowers are even more powerful together.

Nick was the strategist. Always seeing the whole field. Always asking what’s happening at the category level before asking what to do about it.

Lydia was the revenue scientist, marketer, and writer. The former CMO, who had been accountable to boards throughout her career, knew that marketing without a number attached to it is considered arts and crafts.

He asked her to review his Languaging. She gave him feedback. They kept talking.

What started as an advisor and founder became something more valuable.

They became a band.

Two people who had done enough work on their own superpowers to recognize what the other one had.

Pirate Nick said it plainly, “I wanted a thinking partner, not someone coming in and out of my life.”

Then Nick mentioned a conference. Three weeks away.

Lydia said yes before she’d thought it through.

That’s the moment this story really starts.

Nick and Lydia found what we call Business Bandmates—and how to find yours is one of the most important chapters in Creator Capitalist. Chapter 14 breaks down exactly what to look for, how to know when you’ve found them, and why the right bandmate compounds everything you’ve already built. Join the waitlist to be the first to get our new book, Creator Capitalist, here.

The OG Problems in Personal Injury: The Invisible Victim and Settle for Safety Attorneys

Before we get to the strike, you need to understand their problem and POV.

A problem worth solving and a point of view worth defending—these are two of the most important things a Creator Capitalist must have before they do anything else. Without them, you don’t have a business. You have a hobby with expenses.

Do not execute a Lightning Strike until you do the core Category Design work.

Pirate Nick had been jamming on the core category problem in personal injury law back when he was in Strategy Therapy with the Pirates.

The conventional wisdom about Personal Injury (PI) law is:

1. PI has too many clients faking and inflating injuries.

2. PI attorneys are ambulance chasers.

3. PI law is too big as it is.

But Nick knows how to reject the premise. His POV is that:

1. There are too many victims who don’t get the legal help they need.

2. PI attorneys are too risk-averse, settling for too little, too fast.

3. PI law should be billions of dollars bigger.

Is he right? Let’s look at some weird data.

1. Each year, there are 400K PI clients.

2. 5.1MM/year medical consulted injuries from motor vehicles.

3. 5.45% of PI leads turn into a consult, the lowest of any law field.

4. 96% of PI cases settle before reaching trial, per Clio and the DOJ.

Are there excessively litigious folks who inflate their injuries? Sure.

But the numbers suggest there are exponentially more people who suffer in silence.

Here are the three stages of how a person becomes a personal injury client.

• The Invisible Victim. You get hurt, but medical help comes before legal help.

• The Perplexed Prospect. You Google lawyers, but have no idea what to do.

• The Undervalued Client. You find a PI attorney who settles for less.

Most people handle a personal injury and hope their insurance covers as much as possible. Or worse, they end up in medical bankruptcy. As high as two-thirds of all bankruptcies are medical.

This is despite the fact that personal injury legal pricing is as missionary as they come.

Your PI attorney is paid only if and when you are paid. Otherwise, victims pay nothing. The incentives are so strongly aligned that they can be paid one-third of the settlement.

Ambulance chaser has a greedy connotation. But the data shows attorneys aren’t chasing ambulances, they’re watching them drive past. And when they do take a case, they don’t fight hard enough. They fold.

The problem with PI attorneys is not that they are too greedy, but not greedy enough.

That’s why PI lawyers love SEO. It was the one form of client acquisition that was easy. You optimized your website, you ranked for the right terms, and the phone rang. On the other end was a prospect who refused to be an Invisible Victim or Perplexed Prospect.

Then AI happened.

Google is no longer the default first step anymore. Now, when a personal injury happens, more and more people open an AI before they open a search engine.

Because of AI, it’s not just the victims who are invisible.

The personal injury lawyers are invisible, too.

Invisible Victims Can’t See AI Invisible Lawyers

Pirate Eddie has recent, first-hand experience as an Invisible Victim.

Pirate Eddie broke his ankle as he walked from the men’s locker room to the pool deck at Lifetime Fitness. He wasn’t running. He was wearing running shoes. He was walking to the sauna when the next thing he knew, his Apple Watch was going bonkers, asking if he wanted to call 911.

As soon as he got home, he started asking AI medical questions. He got an X-ray at Urgent Care. He uploaded his X-rays to AI. He was told he needed surgery, so he asked about surgery outcomes.

He would repeatedly ask AI medical questions during his early recovery. After a while, it was easy and natural to start asking AI legal questions.

He knew AI was not a lawyer. But Pirate Eddie didn’t know what he didn’t know. And AI was perfect for asking the right questions.

Pirate Eddie wasn’t even aware he was an Invisible Victim. At some point, he became a Perplexed Prospect.

But the scary part for PI attorneys?

Google never got a glance from Pirate Eddie, who didn’t know any PI attorneys.

Which meant the PI attorneys were AI invisible too.

If your business is AI invisible, then it will be like your business doesn’t exist.

Quick zebra hole for the Pirates who want the practical takeaways from Eddie’s experience—skip ahead to ‘Category Science for the Win’ if you want to get back to the strike.

If you fall and break your ankle like Pirate Eddie at a gym, you will be facing a few mini-crossroads where you have to make rapid decisions that could matter. You will be presented with a lot of binary choices. Reject the premise and look for the third option.

1. To Ambulance or not?
   Right after, Pirate Eddie was asked if he wanted an ambulance. Or he could go home on his own. But the choice isn’t binary as there is a third option.
   You can call someone you trust and have them help you home. Have someone bring you crutches or a scooter.

2. More information is better.
   Right when he fell, two good Samaritans rushed to his side. He was grateful for their help, but never got their names. One said to him, “Let me know if I can help. I saw everything.” He wasn’t sure what that meant, but in hindsight, Pirate Eddie wishes he had gotten their contact info, as well as taken photos/videos of the fall area.

3. ER or tough it out?
   For an injury like his that wasn’t life-threatening, it’s tempting to tough it out. But once Pirate Eddie’s wife saw he couldn’t bear weight, she told him he needed an X-ray. But the choice wasn’t just ER or nothing. Immediate/Urgent care is the smarter choice.
   For an injury that isn’t life-threatening, Immediate/Urgent care will cost hundreds, whereas the ER can cost thousands.

Pirate Eddie asked Lifetime whether they would offset his out-of-pocket medical bills. They were polite and referred him to a third-party processor, and the claim was denied. Like most gyms, Lifetime requires members to sign a waiver.

Pirate Eddie’s revenue to Lifetime Fitness was nearly $4K per year. The entire experience left a bad taste in his mouth, and he canceled his membership, even though he knew another gym would require another waiver.

Gym unit economics mean that after a certain number of memberships, each dollar of revenue yields mostly profit. A good-faith gesture would be breakeven in one to two quarters, along with strong positive word of mouth. Lifetime value matters, ironically.

Okay, back to our originally scheduled program!

Organic click-through rates have dropped 61% for queries with AI Overviews per Seer Interactive. Someone gets rear-ended, is scared, opens Claude, and asks, "Should I call an attorney?" Who should I call in my city?

Those cases are gone before they ever hit a search results page. Can’t track them. Can’t retarget them. Can’t see them in Google Analytics. Just gone.

This is where Pirates Nick and Lydia Language a legendary POV in the Category Design Academy.

Are you AI invisible?

Category Science for the Win

Pirates Nick and Lydia had the right words.

Now they needed the right numbers. They conducted Category Science, built an index, and created a diagnostic.

Here’s what Nick and Lydia found.

Read more

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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

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Dear Friend, Subscriber, and Category Pirate,

New research is showing what we’ve suspected for a while: on average, AI is making people stupider over time.

Not because AI is bad. Because most people use it badly.

They show up with radical obvious—”write me a blog post about the 10 smart things to do in marketing for 2026”—and get radical obvious back. They skim it, copy-paste it, and move on. Their core premise never gets challenged. Their thinking never improves. AI becomes a mirror that makes them look smarter without making them actually smarter.

That’s the trap.

AI is, by definition, a synthesis of all existing knowledge. When you ask it obvious questions, you get the average of everything that’s already been said. You get a very polished, very fast version of what everybody already knows.

Creator Capitalists do the opposite.

They don’t use AI to do their thinking. They use AI to help their thinking. And the difference between those two things is the entire ballgame.

When you live in the obvious, AI makes you stupider. When you live in the non-obvious—and connect it to the obvious—you create legendary magic.

Here’s what that looks like in practice.

In this conversation, Pirate Eddie uploaded 20 Creator Capitalist profiles into Claude. Not structured data. Not a spreadsheet. Just stories—unstructured, messy, human stories about how 20 different people made the shift from Knowledge Worker to Creator Capitalist.

But here’s the part most people would skip: Eddie didn’t say “find me something cool.” He showed up with a hypothesis. A point of view. A specific lens he wanted to pressure-test.

That hypothesis is the difference between using AI to think for you and using AI to think with you. Without it, Claude would have produced a generic word cloud. With it, Claude produced category science—origin story buckets, career stage analysis, seniority distribution, company size breakdowns—that none of us would have created on our own.

Eddie brought the judgment. Claude brought the processing power. Together, they created Intellectual Capital that neither could have produced alone.

Creator Capitalist goes deep on how to use AI to scale your Intellectual Capital as a Creator Capitalist. The book launches March 17. Join the waitlist at creatorcapitalist.ai, and you'll get the Introduction and the opening of Section 1 for free, delivered to your inbox immediately. You'll also be able to order a full day early on March 16—before the public launch.

And then Eddie did something else that matters. He prompted the charts—”first one, horizontal bar. Second, vertical bar. Third, I don’t like pie charts, you come up with something different”—and Claude delivered visualization formats Eddie had never seen before. He said “look at our website, grab our color scheme” and got publication-ready graphics.

What would have taken a consulting team a week happened in one sitting. AI isn’t magic without thinking worth amplifying.

AI doesn’t need you to be clever. It needs you to give context. And context starts with having a point of view.

The conversation goes somewhere unexpected from there.

Bri didn’t recognize herself in the data. Claude categorized her as “accidental discovery”—but she would have placed herself in “frustration, trauma, survival.” Both are true. It turns out Creator Capitalist journeys look different from the inside than the outside. That tension—between how you see your own story and how the data sees it—opens up something none of us anticipated.

Christopher shares a moment of vulnerability that will surprise anyone who thinks confidence comes standard with success. And the Circleback Neenanana makes its official debut as a concept. (You’ll know it when you hear it. And you’ll immediately think of three people in your own life.)

The data itself—what the 20 profiles actually reveal about who becomes a Creator Capitalist and why—we covered in our mini-book last week.

This conversation is different.

This is what it looks like when three people sit down with AI-generated category science and start jamming on what it means, where it breaks, and what it tells you about your own path.

Here’s how to navigate this conversation:

• 00:01 – The setup: the book is days away, the Founding 50 are in, and Eddie has done something with Claude that changes how we think about category science.

• 00:44 – Word crunching, not number crunching: why analyzing unstructured stories with AI is fundamentally different from everything consulting has done before—and why it only works when you show up with a hypothesis.

• 06:18 – The Circleback Neenanana: Christopher on the special fuel of “I’ll show you”—and why some of the best Creator Capitalists were forged in the fire of getting screwed over.

• 08:31 – The less-celebrated paths are the majority: why frustration, hobby, and accidental discovery outweigh deliberate professional reinvention in the data—and why that should give you confidence.

• 15:11 – “I would not have placed myself in that bucket”: Bri on why Claude categorized her differently than she would have categorized herself.

• 23:48 – The meta-lesson: Christopher names what Eddie is demonstrating in real time. One person creating publication-quality category science with AI. “That’s the definition of leverage.”

• 29:02 – What AI can’t do: the human work—writing the profiles, knowing the people, bringing a hypothesis—is still everything. AI organized the data. Humans created the data.

• 32:40 – Does pedigree matter? Rafi Mohammed (PhD from Cornell) versus Coffeezilla (nobody knows his real name). Both Creator Capitalists. Christopher’s answer will not be diplomatic.

AI can produce the same faster than any human ever could. The people who show up with obvious get obvious back at unprecedented speed. The people who show up with a point of view, a non-obvious lens, a hypothesis worth testing—they get leverage that didn’t exist two years ago.

This conversation is proof. One hypothesis. One AI. Twenty stories. And category science that would have been impossible without both the human and the machine.

Chapter 20 of Creator Capitalist is called “Vibe Creating”—and it breaks down exactly how to work with AI as a co-creator, not a content machine. The book launches March 17.

The book launches March 17.

Join the waitlist at creatorcapitalist.ai.

Here’s what you get:

• 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.

• A launch-week-only bonus we’re announcing soon that won’t be available after March 21. Waitlist members hear about it first.

👉 Join the waitlist here.

The people who show up to AI with thinking worth amplifying are about to have the most unfair advantage in the history of work. The book shows you how to be one of them.

Arrrrrr,

Category Pirates 🏴‍☠️

Eddie Yoon

Christopher Lochhead

P.S. — If you listened to this episode and thought "I have a hypothesis I've never tested."

That's your Intellectual Capital talking. The book gives you the system for codifying it, scaling it, and getting paid for it. creatorcapitalist.ai. Free intro the moment you sign up.

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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

Arrrrr! 🏴‍☠️ Welcome to a free (for now) edition of Category Pirates. Each month, we publish mini-books that share radically different ideas to help you design and dominate new categories. Thank you for reading, and of course, forward this “mini-book” to any friends you think need to hop aboard the Pirate ship.

Subscribe now

Dear Friend, Subscriber, and Category Pirate,

You’re busy.

Your calendar is full. Your inbox never empties. People rely on you to get things done.

On paper, your career looks fine. Good education. Solid career trajectory. A résumé that others respect.

And yet something feels off.

You’re working more than ever. Your title and your office are bigger. But somehow you don’t actually feel powerful. You have many direct reports. You no longer have one boss, but many. So why does it feel like you work for all of them?

You feel helpless.

Most people don’t say that out loud.

For decades, most careers ran on the same operating system:

• 70% reactive: emails, requests, meetings, fire drills

• 20% active: collaborating and contributing to projects

• 10% proactive: thinking, creating, deciding what matters

This was the Knowledge Worker economy.

And it worked if you were great at reacting fast, responsively, and reliably. The system rewarded you. People built very real and often lucrative careers this way.

Then AI arrived.

Tasks that took hours to do got done in seconds. Previously impressive output now looks lame when AI can do so much so quickly. AI is bending the time and reality of work.

Being reactive was okay when you needed to react fast every now and then, and then mindlessly execute. You could go on autopilot and mentally relax. But when AI distorts time and productivity, expectations have increased exponentially. Since tasks take much less time, you are expected to do much more. You need the reactivity skills of an F1 driver.

The new reality looks more like this:

• 70% proactive: thinking, deciding what matters, creating

• 20% collaborative: working with AI agents and also humans

• 10% reactive: approving, managing, adding guardrails, and context

Execution became abundant.

Existing knowledge moved closer to being free. Reactivity is non-stop and no longer a competitive advantage. The greatest human cannot work faster than a GPU.

Being busy used to be a signal of a good knowledge worker.

Now, being busy is a poker tell that you are behind the times with AI.

The Value of Your Value Got Devalued

People do not know how to be proactive 70% of the time.

You were never trained for it. You were rewarded for memorizing and regurgitating. You were never expected to think about your thinking. Lots of people went from their parents, to professors to bosses telling you what to do.

Now you have to think on your own?

This is where the anxiety comes from.

The source of value moved upstream:

• From doing to deciding

• From knowing to judging

• From responding to framing

• From executing to designing

• From answering to questioning

• From technique to taste making

You’re busy inside a system that no longer pays for busyness.

That’s why you feel powerless. That’s why you feel helpless.

The good news is that value didn’t disappear. It relocated to people who can frame problems worth solving, see what others normalize or ignore, use AI to scale judgment (not replace it), create approaches that didn’t exist before, and decide what matters before execution begins.

These people are not busier. They are decisive. They are not reacting to the future. They are shaping it.

From Knowledge Worker To Creator Capitalist

The people who made the biggest difference in any era were never the best executors of existing approaches.

They were the ones who brought something different to the problem. A perspective, an insight, a way of seeing that others simply didn’t have.

What’s changed is not that different suddenly matters; it’s that everything else stopped mattering as much.

The world moved from a place where power came from how much you knew, how fast you responded, and how much you could execute—to a world where value comes from how much net new knowledge can you create, how easily can you apply that knowledge to create outcomes, and how can you codify it into Financial, Reputation, Relationship, and Intellectual capital.

You no longer have to trade your precious time for money. You can make money in your sleep. You can get paid to create. You get paid to be you.

This is the new category of work that comes after Knowledge Worker.

The Creator Capitalist.

Creator Capitalism is not about being a ‘greed is good’ raging capitalist. Nor is it purely about the artist’s view that creativity is all about the artist.

It’s the capacity to see problems others miss, frame opportunities others can’t articulate, combine ideas in ways that didn’t exist before, and convert them into a digital asset you can share, sell, and sleep while you make money.

In a world where execution is cheap and knowledge is free, you are no longer paid primarily for what you do. You are paid for what you create.

Creator Capital is the accumulated value of your difference.

Your perspective. Your pattern recognition. Your instincts. Your ability to see and solve problems that others can’t.

When you are paid to create, your work compounds instead of resets. Your income accelerates faster than your hours. Your career is no longer a treadmill—it reaches escape velocity.

That’s what our new book, Creator Capitalist, is about. Not the theory of why work changed—but the frameworks for making the shift yourself. (You can join the waitlist to be the first to get it on March 17th here.)

Let us introduce you to twenty people who prove it’s real.

Anyone can become a Creator Capitalist

Who actually does this?

Is this real? Or is this just a nice theory for people who were already successful?

Fair question.

In Pixar’s great movie Ratatouille, Chef Gusteau’s famous motto is “Anyone Can Cook.” The protagonist is a rat with refined taste named Remy who wins over the most revered and feared food critic in all of Paris, Anton Ego. Think Gordon Ramsey crossed with Simon Cowell and Ricky Gervais in a bad mood. Ego’s POV is that very few people can cook.

The movie is a battle of POVs. Anyone can cook, vs. very few people can cook.

If you haven’t seen it, you should. The movie is all kinds of hilarious and accurate. Chef and Restaurant Mogul David Chang grudgingly admits the most authentic movie about cooking ever is “that f*&#ing rat movie.”

Ego is eventually transformed by Remy’s cooking. He is humbled, then refines and integrates the two POVs. He says, “Not everyone can become a great artist, but a great artist can come from anywhere.”

That’s also true of becoming a Creator Capitalist.

We’re not saying everyone will become a Creator Capitalist. We’re saying a Creator Capitalist can come from anywhere—Singapore, Auburn University, a boat in Canary Wharf, Deutsche Bank, an esthetician school, a farm with zero internet.

One of our favorite things about our new book, Creator Capitalist, is the appendix.

(That’s a sentence nobody has ever written before.)

But it’s true. Because the appendix is where all twenty Creator Capitalist stories live, side by side—the origins, the struggles, the breakthroughs, the playbooks. It’s the part of the book people will dog-ear, screenshot, and send to their friends.

We’re going to give you a brief look at those twenty people right now. And what Pirate Eddie found when he studied all twenty will surprise you: the pattern is there is no pattern.

Trust that Pirate Eddie used all the category science to look for one.

The No-Pattern Pattern

We looked at everything.

Parenting. Education. Net worth. First job. Age. Gender. Seniority. Company size. Whether they came from trauma or privilege. Whether they started at fourteen or forty. Whether they had an PhD, GED or IUD.

None of it predicted who would successfully make the leap.

The only thing these twenty people have in common is that they have nothing in common. Different industries. Different starting points. Different superpowers. Different origin stories. The data refused to cooperate with a tidy narrative.

Which, if you think about it, is the most encouraging finding of all. Because it means the door isn’t locked to people who look a certain way, went to the right school, or had the right connections. The door is open. It’s just that most people are too busy to notice.

Here’s what we mean.

It doesn’t matter if you had wonderful or horrible parents.

Carylyne Chan grew up in Singapore with a psychopathic father who tried to murder her and her mother. She started her first internship at fourteen, not for enrichment—for survival. She wanted control over her physical safety. She had two startup exits and financial independence before she turned thirty.

Jeff Klimkowski’s origin wasn’t trauma—it was a deep childhood friendship with Sean Riley and Ryan Meegan that became the rock-solid foundation for DUDE Wipes. That’s an entirely different level of trust.

It doesn’t matter where you went to school or the size of your company

Joe Pine created his first Intellectual Capital in high school, compiling a Tolkien Linguistics Dictionary. “I am very much a nerd from way back.” His professor at MIT saw his potential and nurtured it.

Monroe Jones went to Auburn University to study architecture, following in his father’s footsteps. Architecture wasn’t his first love. One of his professors sat him down and said, “This is not your first love. What are you doing?”

It doesn’t matter what your first job was or how well you did on it.

Danny Bauer was a high-achieving principal who won every award available—and was on the verge of being fired for breaking the unwritten rules of school leadership. He cared more about student outcomes than staying in line.

Alexis Kowalsky went to esthetician school and got rejected from her dream job because they said she needed experience she couldn’t get without a job. So she was forced to become a solopreneur. She built Best Ever Skin, running herself ragged.

It doesn’t matter if you started young or later in life.

Carylyne Chan had two exits before thirty. Joe Pine has been building on the same body of intellectual capital for three decades—and his ideas feel fresher and more powerful today than when he published The Experience Economy in 1999. Roger Whitney reinvented himself in his forties, after finally achieving professional success, when he realized he was his own superconsumer.

It doesn’t matter how much money you had or didn’t have.

Pablo Gonzalez and his wife made a deliberate choice to lower their cost of living so he could invest in long-term leverage instead of short-term transactions.

Mike Maples Jr. left a successful career as a CMO to become a seed-stage venture capitalist—not because what he was doing was failing, but because he saw the future and it was beautiful and he didn’t want to miss it.

Your gender, your age, your height, your weight, your looks, your ethnicity, and your family of origin don’t matter.

The Pirates in this book aren’t unicorns.

They’re not trust fund kids. They’re not lottery winners. They didn’t get lucky breaks that you couldn’t get.

They’re people who saw a problem worth solving, had the courage to share their perspective, built the Four Capitals (Financial, Reputation, Relationship, Intellectual), and designed work they love instead of work they tolerate.

Some started as financial planners. Some started as music producers. Some started as lawyers. Some started as designers.

What they all have in common is this.

They stopped trading time for money and started building capital that compounds. They chose agency. They saw that today was the best time to start.

Creativity is abundant and emerges from anywhere

You might be saying, “But I’m not creative. How can I be a creator capitalist?”

There’s truth to this. Not everyone is as artistically talented as Monroe Jones. But creativity isn’t something you’re born with. Creativity stems from the desperation to solve a problem you see and that matters to you and others.

Look at where our Creator Capitalists started. Does each job scream creativity to you?

• Bri Clark was a solo designer.

• Melissa Andrews was in telecom.

• Nick Kringas ran an SEO agency.

• Adam Frankl was a startup CMO.

• Joe Pine was an employee at IBM.

• Danny Bauer was a school principal.

• Alexis Kowalsky was an aesthetician.

• Mike Maples Jr. was a VP of Marketing.

• Lydia Flocchini was a legal tech operator.

• Rafi Mohammed was a consultant at Monitor.

• Roger Whitney was a certified financial planner.

• Paul Millerd was in consulting/executive search.

• Holley Miller was a marketing director at Allergan.

• Jack Bigbee was the “data/tech nerd” on a marketing team.

• Jeff Klimkowski was an investment banker at Deutsche Bank.

• Jessica Gregson was running an advisory practice from a boat.

• Thomas Parrott was a direct-to-consumer/infomercial executive.

• Pablo Gonzalez was organizing charity events for young professionals.

Not one of them woke up one morning and said, “I’m going to be a Creator Capitalist.” They became one. Often accidentally at first. Then deliberately.

Isn’t there a pattern and a playbook?

Yes to a playbook. That’s in the book, and we give you a preview in this mini-book.

These six things form the playbook at the heart of our book. Here’s a preview. The book goes deep on each one, with all twenty stories showing you exactly how it works.

1. Each of them found their problem before their product

Here’s what separates Creator Capitalists from Knowledge Workers with good résumés: the problem found them before they found the product.

The most powerful problems are personal.

They are the problems that refuse to leave you alone, irritate you more than others, follow you across roles and industries, and connect directly to your lived experience.

Roger Whitney discovered his clients weren’t really asking money questions—they were asking identity questions about who they’d be when they stopped working. Rafi Mohammed turned a pricing hobby into an obsession after realizing that everyone from Fortune 500 CEOs to his local butcher had a pricing problem. Melissa Andrews saw that farms had zero connectivity while cities were fully wired—and nobody was asking why. Monroe Jones watched producers ridicule artists and decided the real problem in music was shame, not talent.

The problem you’re meant to solve is rarely “out there.”

It’s already been shaping your career. You just haven’t named it yet.

The book walks you through exactly how each of the twenty Creator Capitalists found their problem—and how you can find yours.

2. Every one of them delivered extraordinary outcomes

Most sell effort.

Some sell expertise.

Creator Capitalists sell outcomes. That’s the difference, and it’s the reason they have pricing power.

Holley Miller helped grow a brand from $25 million to $100 million in four years at Allergan—not by adding incremental sales reps, but by reframing the market. The product didn’t change. The belief about the category did.

Pablo Gonzalez helped a client create a $40 million dollar channel from a community-driven growth engine he built on a $6,500/month retainer—an ROI so asymmetric it permanently reframed how he understood the value of relationships.

Monroe Jones has been a trusted creative partner for 40+ years, mostly off the celebrity stage, working with U2, Stevie Nicks, and David Crosby—because he traded short-term credit for long-term Relationship Capital.

When you reliably deliver outcomes, the conversation changes.

You have pricing power.

Pricing power is the foundation of capitalism.

3. They Framed, Named, and Claimed their Superpower

Every Creator Capitalist had a breakthrough moment where the fog cleared, the language clicked, and everything changed.

She who frames, names, and claims the problem wins.

You must have clarity on the problem you are solving and be able to reliably deliver outcomes for a clear superconsumer. But even with this, it doesn’t help if you can’t explain it clearly, concisely, and compellingly.

When you frame the problem, you create a demarcation point in thinking by setting the context and forcing people to consider why this specific idea demands urgent attention.

When you name the problem, you choose a distinctive and sticky label that immediately captures its essence.

When you claim the problem, you become the solution. Not because your product is the best, but because every superconsumer knows your mission in life is to solve the problem.

Thomas Parrott spent months trying to category design his consulting business.

He thought his niche was taking US companies to the UK and Europe. He had done it before. He knew the territory. He had the skills. Except it wasn’t a category. It was a service delivery model with a brutal pipeline. Long sales cycles, complex deals, hard to scale. Then, during an Academy jam session, he mentioned “contribution margin” in the midst of a longer point. Eddie started waving his arms. Christopher started dropping f-bomb after f-bomb. The new category crystallized: Contribution Margin Growth Architect.

Within a week, Thomas had two huge clients. The sales cycle went from 30 weeks to 30 minutes. “I literally iterated what I was doing so clearly: I help e-commerce businesses find operational excellence by focusing on the levers of contribution margin to find solutions for financial misalignment at scale. And they said, ‘We’ve got something going on right now, we’d love to talk.’”

Danny Bauer had been talking about the right thing, the wrong way, for ten years.

His superconsumers—school leaders who cared more about student outcomes than staying in line—didn’t want leadership theory. They wanted leadership that works in real life. As he shared his POV in the Academy, “Ruckus Makers” was a throwaway line. The Pirates hit the brakes and helped him see that Ruckus Maker was not mere branding. It was a filter that drew his superconsumers straight to him like a tractor beam and repelled the risk-averse who weren’t ready.

Jessica Gregson’s advisory practice had many of the right ingredients.

They had experience, capability, care, and a strong advisory instinct. What it didn’t yet have was a named, claimed problem that pulled everything together.

Founder’s Block is the answer.

Founder’s Block existed intuitively before it existed strategically. Jess and her team could see it in clients, feel it in conversations, and work through it in practice—but it hadn’t yet been fully framed as the problem.

Extra Brain is built around a simple but powerful idea: founders don’t lack intelligence, ideas, effort, or ambition—they, at times, lack momentum. Founder’s Block stopped being an internal shorthand and became a rallying point—something clients could recognize themselves in.

Two small words. Massive meaning. Revenue growth 4x higher than the previous year.

Here’s the pattern: every Creator Capitalist in this book had a superpower long before they had the words for it. The naming didn’t create the superpower. It unlocked it. It gave them clarity, and clarity created confidence, and confidence created pricing power, and pricing power created freedom.

If you’re struggling to frame, name, and claim the problem, you’re probably not solving the right problem.

But if there’s something that’s been following you—a pattern you keep seeing, a frustration you keep feeling, a question you keep asking that nobody else seems to ask—that’s not noise.

Remember that framing, naming, and claiming are a mix of art and science. But it is more like a music lyric, poetry or a mantra.

You don’t grab hold of the lyric. It grabs hold of you.

So take a deep breath and recognize you must practice this in public. It will be scary like going on American Idol and singing in front of the world.

But the only way to write a song people can’t forget is to sing it in front of others.

Even if it is a bit out of tune.

The book walks you through the exact framework for framing, naming, and claiming your superpower—so you don’t spend years talking about the right thing the wrong way.

4. They all built The Four Capitals, accidentally at first

Nobody starts by planning all four. That’s the counterintuitive part. Creator Capitalists build four kinds of capital that make courage sustainable—but nearly every one of them started building before they knew what they were building.

Financial Capital (having a long enough runway to make the leap), Reputation Capital (the signal that travels ahead of you), Relationship Capital (the people who multiply your efforts), and Intellectual Capital (the ability to create outcomes for others while you sleep).

Carylyne Chan started building Reputation Capital at 14 with social enterprises, which led to Relationship Capital with school principals, which led to Intellectual Capital as she honed her ability to stay calm in chaos, which led to Financial Capital via a nine-figure exit and financial independence at 29.

Pablo Gonzalez’s wife became a force multiplier, not a constraint—freeing him to invest in Relationship Capital through community building that eventually created a $40 million channel for a single client.

Bri Clark built all four capitals by doing one thing: having the courage to publicly roast businesses’ websites. With love. But she roasted them.

The order doesn’t matter.

The sequence is different for everyone. What matters is that all four eventually get built. Because once they compound together, courage becomes rational. Not reckless.

The book gives you the framework for building all four capitals—which one to start with, how they compound, and when courage becomes rational.

5. They found their bandmates

No one creates a category alone.

The myth of the solo genius is just that—a myth. Every Creator Capitalist in this book found people who sharpened their thinking, expanded their reach, or complemented their blind spots.

Nick Kringas and Lydia Flocchini were two legendary legal pirates who decided to partner up. Two pirates, both crushing it in legal. Lydia was the builder—the operator who could take a category POV and make it real through storytelling, systems, processes, and people. Nick was the strategist—the captain who could navigate shifting seas and see the category opportunity. Together, they were better than the sum of their parts.

Jeff Klimkowski, Sean Riley, and Ryan Meegan started DUDE Wipes with deep childhood friendship as the foundation. Monroe Jones gave up songwriting credit to earn trust—and the more he gave up credit, the more abundance he got. Artists opened up. Songs got better. Relationships lasted decades.

The right collaborators don’t dilute your difference.

They amplify it.

The book gives you a framework for finding the right bandmates—and knowing the difference between collaborators who amplify your difference and ones who dilute it.

6. AI didn’t threaten them—It accelerated them

AI doesn’t replace Creator Capitalists. It makes them exponentially more powerful. But only if you’ve already built the foundation.

Jack Bigbee helped rebuild the Category Pirates business with AI as a co-founder—not by writing code, but by translating intellectual capital into scalable, interactive technology.

Nick Kringas saw that AI was going to transform how clients find and choose lawyers, so he and Lydia Flocchini created LawShift to help personal injury law firms survive and win as AI reshapes discovery.

Melissa Andrews used AI and connectivity to put Starlink on tractors—not because she had better technology, but because she asked better questions.

They used judgment, perspective, and taste with AI to amplify everything they were already doing.

The limiting factor is no longer technology. It’s you. The more human you are, the more powerful AI becomes.

The book walks you through a framework for using AI to scale your Creator Capital—not as a replacement for your thinking, but as an amplifier of it.

Now it’s your turn.

Ask Yourself Four Questions.

You just met twenty people who made the shift.

None of them had an unfair advantage that you don’t have access to. None of them followed a path you couldn’t follow. The only thing they had that you might not have yet is clarity—about the problem they were born to solve, the capital they needed to build, and the courage to do it in public.

If you’ve made it this far, something important has already shifted.

You now understand why being busy stopped working and where power actually went.

You’re no longer confused about why execution feels less valuable. You’re no longer blaming yourself for a system that quietly changed. You’re no longer mistaking motion for progress.

The most important thing Creator Capitalist gives you back is not confidence. (This is no whoo-whoo motivational mumbo-jumbo, new age crap-o-la.)

It’s clarity.

Clarity about why the rules shifted. Why your leverage shrank. Why your instincts were right. And why your different is no longer something to smooth out.

Once you have that clarity, power returns. Not as control over everything. But as control over what you choose to engage with.

You stop chasing approval. You stop over-optimizing execution. You stop waiting for permission to think.

You start deciding before doing. Designing instead of reacting. Creating direction others can follow.

That’s what power looks like now.

So here’s where it gets personal.

Twenty Creator Capitalists showed you what the shift looks like from the outside. But this isn’t about them. It’s about you. And it starts with four honest questions.

Question 1: Do you yearn for different?

The future is being built. Whether you participate or not. And right now, opting out is not neutral. It’s a decision to let other people’s priorities shape your future.

The original American Dream was never about money. It was about agency. The right to pursue opportunity. The freedom to own your future. But over time, that dream was quietly rewritten. The new promise became stability instead of upside. Security instead of agency. Retirement instead of relevance.

Don’t retire from work. Retire from work that drains you.

Question 2: Do you still want to play someone else’s game?

Most people spend their lives trying to win games they didn’t design.

They optimize for rules they didn’t choose. They compete on metrics they didn’t invent. They chase rewards defined by someone else. And then they wonder why winning feels empty.

The most successful people in the world do something different. They don’t fight harder for position inside existing games. They create games worth playing. Not by cheating. Not by escaping reality. But by reframing what matters. They decide which problems are worth solving, which outcomes actually count, which rules they’ll play by—and who they want on the field with them.

That’s category design. Master it, and you become a category of one—not a creator who competes, but a Creator Capitalist who owns.

What problem has been following you across roles, across industries, across years? What do people come to you for that they don’t go to anyone else for? What do you see that others normalize or ignore?

The book gives you the framework for designing it.

Question 3: Are you ready to build the four capitals?

It takes courage to be legendary.

Not the loud kind. Not the “burn the boats” kind. Real courage is the willingness to take on work that is hard, uncertain, worth doing, and visible enough to fail in public.

That kind of courage doesn’t come from motivation. It comes from preparation. Courageous people aren’t fearless. They’re prepared. They’ve built enough foundation underneath themselves that they can take a meaningful leap without destroying their lives if it doesn’t work.

Recklessness is acting without a basis. Courage is acting because you’ve built one.

That’s what the Four Capitals are for. Financial Capital gives you the runway to make the leap. Reputation Capital is the signal that travels ahead of you. Relationship Capital is the people who multiply your efforts. Intellectual Capital is the ability to create outcomes for others while you sleep.

You don’t need all four to start. Carylyne started with Reputation Capital at fourteen. Pablo started with Financial Capital by lowering his cost of living. Joe started with Intellectual Capital in high school. Bri started with the courage to share her thinking when no one was watching.

You start with whichever one you’ve already been building—whether you knew it or not.

The book shows you the framework for building them—and the order that makes courage sustainable.

Question 4: Do you believe your different can make a massive difference for others…and you?

This is the real question.

Your superpower is not your skill set. It’s not your résumé. It’s not your experience. It’s not even your intelligence.

Your real superpower is the specific way your different helps other people achieve massive outcomes and abundance.

The only advantage left is different applied to meaningful problems.

Creator Capitalists don’t win because they work harder. They win because they tap into what is uniquely theirs—their perspective, their instincts, their superpower—and apply it to the problems that matter most.

You are not late. You are not obsolete. You are, in fact, the only person in the history of humanity with your specific superpower.

Do you believe that?

We believe it with all our hearts. We believe you are designed to be different. We believe you are destined to make a difference.

Nothing about this path is guaranteed. Creator Capitalism is not safe. It’s not fair. And it’s not for everyone. It asks you to own your choices, trust your judgment, be responsible for what you create, and accept that different carries risk.

But it also offers something rare. A career that compounds instead of resets. Work that stays interesting instead of exhausting. And the chance to be well-paid for making the difference only you can make.

The future does not need more busy people. It needs people who can think upstream, think differently, create new value, and take responsibility for shaping outcomes.

You’re standing at the moment where power moved. With a decision to make.

Being busy without power was the symptom. The shift in how work creates value was the cause. Your different is the leverage.

And if you choose to play it—deliberately, courageously—and on your own terms, you won’t just survive a post-AI world. You’ll help shape it. By using who you are to create what’s missing. And getting paid (well) for making the biggest difference you can.

Knowing the shift and making the shift are two very different things.

This mini-book showed you that the world changed, that Creator Capitalists are real, and that the shift is available to anyone.

But knowing the shift happened and knowing how to make it are two very different things.

Creator Capitalist—the book—goes deep on all twenty stories. Not just who they are, but exactly how they found their problem, framed and named their superpower, built the four capitals, found their bandmates, and used AI to accelerate everything. The frameworks. The sequences. The mistakes. The breakthroughs. The specific moves you can make — starting now.

The future needs you.

Go create it.

Arrrrrrr,

Category Pirates

Eddie Yoon

Christopher Lochhead

P.S. - Creator Capitalist launches March 17th.

Join the waitlist to be the first to know when the book drops.

Each profile in the book is a full deep-dive—the origin, the struggle, the breakthrough, and the playbook behind their transformation. Here’s a taste of the 20 Creator Capitalists you’ll meet:

• Roger Whitney started as a certified financial planner, helping one client at a time. Became the creator of the Rock Retirement Club, unlocking the insight that retirement is an identity transition, not a financial event. 1,400 paying members, 8 million podcast downloads.

• Monroe Jones started as an architecture student at Auburn, but switched to music after a professor told him, “This is not your first love.” Became a trusted creative partner for 40+ years, unlocking the idea that studios must be sanctuaries from shame. Worked with U2, Stevie Nicks, and David Crosby — mostly off the celebrity stage.

• Carylyne Chan started as a fourteen-year-old intern in Singapore, working not for enrichment but for survival. Became a two-time startup founder, unlocking the superpower of calm in chaos. Nine-figure exit and financial independence before thirty. Angel invested in 70+ companies.

• Thomas Parrott started as a DTC/infomercial executive with a brutal 30-week sales cycle. Became the Contribution Margin Growth Architect, unlocking a category that collapsed that cycle to 30 minutes. Added a zero to his project size with the same level of effort.

• Danny Bauer started as a high-achieving school principal who won every award available — and was nearly fired for breaking the unwritten rules. Became the creator of Better Leaders Better Schools, unlocking the “Ruckus Maker” identity as a tractor beam for superconsumers.

• Melissa Andrews started as a telecom operator watching farms operate with zero connectivity while cities were fully wired. Became the creator of Connected Farms, unlocking “Digital Darkness” as the category name that worked across five countries. Cut her sales cycle from six months to six weeks.

• Jessica Gregson started running an advisory practice from a boat in Canary Wharf. Became the creator of Extra Brain, unlocking “Founder’s Block” as the problem founders couldn’t articulate. Revenue growth 4x higher than the previous year.

• Adam Frankl started as a startup CMO. Became the creator of the “developer-facing startup” category, unlocking a name for something thousands of founders were living but nobody had defined. Helped JFrog craft “Release Fast or Die” — five years later, it became the title on their S-1 IPO filing. His own book became an Amazon bestseller.

• Lydia Flocchini started as a legal tech operator across five companies. Became the co-creator of LawShift, unlocking the “Scaling Stall” as the silent killer of legal tech growth. One client generated $140K in pipeline in less than a month. Eddie told her to quadruple her prices. She did.

• Nick Kringas started as an SEO agency owner who generated over $400 million for personal injury firms. Became the co-creator of LawShift with Lydia, unlocking a new category as AI was about to destroy his old one. After one Strategy Therapy session, his client said, “$5,000/month toward solving this problem is nothing to me.”

• Rafi Mohammed started as a consultant at Monitor with a PhD from Cornell. Became the godfather of pricing strategy, unlocking the insight that everyone — from Fortune 500 CEOs to his local butcher undercharging for Korean-style ribs — has a pricing problem.

• Holley Miller started as a marketing director at Allergan. Became a category reframer, unlocking the belief shift that grew a brand from $25 million to $100 million in four years. The product didn’t change. The belief about the category did.

• Pablo Gonzalez started as a charity event organizer who lowered his cost of living so his wife could be the primary breadwinner. Became a community-driven growth architect, unlocking the power of relationships as leverage. Built a $40 million channel for a single client on a $6,500/month retainer.

• Joe Pine started as an IBM employee who compiled a Tolkien Linguistics Dictionary in high school. Became the creator of The Experience Economy, unlocking a category that’s been compounding for twenty-five years and still feels fresher than when he published it in 1999.

• Jeff Klimkowski started as an investment banker at Deutsche Bank, working 100-hour weeks, packing and shipping wipes by night. Became the co-founder of DUDE Wipes, unlocking a category that 20–30 VCs said would never work. $300K from Mark Cuban. Well over $300 million in retail revenue.

• Bri Clark started as a solo designer. Became someone who gets paid for transformation, not just design, unlocking all four capitals by publicly roasting businesses’ websites. Lives in a dry cabin in Alaska with no running water. Runs off mountains with a paraglider.

• Alexis Kowalsky started as an esthetician, rejected from her dream job because she needed experience she couldn’t get without a job. Became the owner of Best Ever Skin, unlocking the realization that discounts were costing her $200,000. Nearly tripled revenue in two years. Then bought a building.

• Jack Bigbee started as the “data/tech nerd” on a marketing team. Became an AI co-founder, unlocking the ability to translate intellectual capital into scalable, interactive technology for the Category Pirates business.

• Mike Maples Jr. started as a VP of Marketing / CMO. Became a seed-stage venture capitalist at Floodgate, unlocking a life where his comparative advantage compounds. Early conviction bets on Twitter, Twitch, and Okta. “I can’t believe I’m getting paid to do this stuff.”

• Paul Millerd started in consulting and executive search. Became the author of The Pathless Path, unlocking over $350,000 in royalties. When asked what number would interest him, he said, “$600,000.” Then released a $100 Italian-printed premium hardcover and sold 250 copies in two weeks to 22+ countries.

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

Subscribe now

Dear Friend, Subscriber, and Category Pirate,

Jeff Klimkowski is a different kind of CFO.

Yes he has the pedigree as a high flyer at Deutsche Bank.

Yes DUDE Wipes is massively successful, crossing $300MM in revenue last year.

But more importantly, he had a ton of skin in the game as a co-founder and as the OG line of credit for DUDE Wipes.

He’s an in the Arena CFO that would make Milton Friedman proud.

When your money and the company’s money are the same pile, you think differently about every dollar.

Jeff didn’t just become CFO. He redesigned what the role means.

At DUDE Wipes, four verticals roll up to the CFO:

• Finance and accounting

• FP&A

• Sales strategy

• Supply chain.

The problem with how the industry defines the job is that most people think it’s just the first one.

Jeff sits in every major Walmart and Target line review alongside Sean. He hears from the buyer’s mouth what their long-term strategy is—so his forecasts aren’t built on salespeople’s optimism alone. He goes to co-manufacturer meetings so he can look at the whites of the buyer’s eyes before he commits working capital to inventory.

This is not how most CFOs operate.

Most CFOs sit in a skybox. Jeff is on the field.

Zero free cash flow growth. That’s the goal.

Not because DUDE Wipes isn’t profitable. Because every dollar of EBITDA gets reinvested—into working capital, CapEx, and marketing—until free cash flow hits zero at year’s end.

Zero means Jeff is deploying capital at the exact speed the category demands.

Too much free cash flow? You’re not investing enough. You lack conviction. The category will outgrow you while you sit on cash.

Negative free cash flow? You’re over your skis. You’ll need to raise money, dilute equity, and lose control.

Zero is the surfer sitting in the pocket of the wave.

Jeff knows the max growth rate they can sustain in a given year because of this discipline. Right now: 50% per annum at zero free cash flow. When numbers get big, 50% is a big number.

And it’s not set-it-and-forget-it. They’re tweaking the plan constantly—rolling 12 months on the finance side, rolling 24 months on supply chain. New data in, new adjustments out.

The make-free-cash-flow button.

Eddie asked Jeff: when you need to push the free cash flow number, what do you press?

The first answer was boring and brilliant: cash collections from retailers.

Nobody was quarterbacking receivables. Invoices were getting lost in EDI transmissions. POs weren’t registering correctly between systems. Charge-backs went uncontested. It’s the kind of work nobody glamorizes—but hiring one person to own it improved cash collection by 40%.

Now they’re layering in AI agents to match invoices, flag errors, and automate the back-and-forth with retailer portals. The person quarterbacks. The agents do the grunt work.

Second answer: SKU-level demand planning. DUDE Wipes knows how much they’ll sell. The problem is the mix—selling the right product at the right time to the right channel. When a new innovation outperforms expectations, there’s a 90–120 day lead time before they can adjust production. AI that ingests retailer data and optimizes assortment by channel compresses that gap.

Real example: DUDE Wipes was running promotions at food retailers and only seeing 10–15% lift versus competitors. Why? They were selling out by Wednesday. Empty shelves for the rest of the week. High-growth category problems that only show up when you look at the data with precision.

Meet Diesel Dan.

Greg Brown, DUDE Wipes’ SVP of Ops and Technology, built an AI agent called Diesel Dan.

Here’s what Diesel Dan does: when the manufacturer finishes a production run, an automated report gets sent over. Diesel Dan reads the report, books trucks across three counterparties, maximizes weight and volume per load, and notifies the operations team. Fully automated.

Before Diesel Dan, inventory piled up at the manufacturer because trucks weren’t getting booked fast enough. That meant less production capacity. That meant slower growth. That meant working capital sitting in the wrong place at the wrong time.

Dan fixed the bottleneck. Stockouts dropped. Freight costs stabilized. And the operations floor went from reactive to predictive.

As Jeff put it: “Dan never sleeps, never guesses, and never forgets.”

This episode isn’t about spreadsheets.

Or accounting.

Or even AI.

It’s about what happens when the CFO stops being the department of no and starts designing the financial system that powers category creation.

Jeff’s approach works because the conditions force it. Skin in the game. A new category that didn’t exist. And a bootstrap discipline that makes every dollar earn its spot—or get cut.

That’s the Agentic CFO.

Here’s how to navigate this conversation:

• 00:00 – From Deutsche Bank to DUDE Wipes: Jeff’s origin story—the Wall Street Journal in the passenger seat, the dream job, and the childhood friends who derailed everything.

• 01:59 – The four verticals of a real CFO: Finance & accounting, FP&A, sales strategy, and supply chain. Why most people only know about the first one.

• 09:06 – Investing 18 months ahead of demand: Writing checks for CapEx three years out. Why Jeff sits in every Walmart and Target line review. And why he’s been wrong on the downside of every forecast.

• 16:54 – The VC rejection that saved DUDE Wipes: 20–30 meetings after Shark Tank. Every one said no. “You’ll never get guys to use wipes.” So they got profitable instead.

• 18:48 – “EBITDA is the most overrated metric on the face of the planet.” Jeff’s financial North Star: free cash flow equals zero. What that means, why it works, and how it sets the pace for growth.

• 26:35 – The make-free-cash-flow button: Cash collections, AI-powered invoice matching, and a 40% improvement from one hire.

• 31:23 – SKU-level demand planning with AI: The working capital problem nobody talks about—selling the right mix at the right time.

• 34:50 – Selling out by Wednesday: Why DUDE Wipes’ promotions were underperforming and what they found when they looked closer.

• 36:30 – Diesel Dan: The AI agent that books trucks, maximizes loads, and turned DUDE Wipes’ supply chain from reactive to predictive.

• 41:53 – Jeff’s AI wish list: Sales strategy, demand planning, and why legal is about to get 70–80% automated.

• 44:59 – Why Jeff said yes: Credibility, alignment with strategy, and the only pitch that works—”here’s how many thousands of hours this saves.”

This conversation is the case study. The Agentic CFO is the system.

In the mini-book, we break down Milton Friedman’s four ways to spend money, the four CFO archetypes (Arena, Dividend, Enabler, and Government), why free cash flow—not EBITDA—is the strategic metric of belief, and the five-step playbook for designing an Agentic finance system with AI agents.

Jeff is the Arena CFO. Which quadrant are you in?

Read The Agentic CFO

To connect with Jeff:

• Jeff Klimkowski on LinkedIn

• DUDE Wipes

Arrrrrr,

Category Pirates 🏴‍☠️

Eddie Yoon

Christopher Lochhead

P.S.—Remember Friedman’s matrix?

The Arena CFO wins because they have skin in the game AND a new category to build.

That’s not just true for CFOs. It’s true for careers.

The knowledge workers who thrive in the next decade won’t be the ones with the best resumes. They’ll be the ones who stop renting out their expertise and start owning what they create.

Our new book, Creator Capitalist, launches March 17th. We’re opening the Founding 50—exclusive early access for Academy alumni and founding subscribers.

Founding Subscribers can join the Founding 50 here.

You can become a Founding Subscriber here.

Or join the waitlist to get the book on March 17th 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.

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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:

Read more

Arrrrr! 🏴‍☠️ Welcome to a 🔒 subscriber-only edition 🔒 of Category Pirates. Each week, we share radically different ideas to help you design new and different categories. For more: Audiobooks | Category design 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,

Jeff Klimkowski didn’t plan on his career ending up in the toilet.

For more than a decade, he built a career in the high-stakes world of investment banking. He loved the work, the rigor, the precision, and the people. He learned how capital moves, how deals get done, and how to be a trusted advisor to CEOs.

At the same time he and a few childhood friends saw the future after having too many burritos and beer. Flushable wipes for men.

They called it DUDE Wipes.

What began as a side hustle with a sense of humor became something serious. And Jeff, the banker who once modeled billion-dollar companies in spreadsheets, decided to help build one from scratch.

He got up out of the stands and got into the arena.

But Jeff didn’t just become CFO. He re-designed the CFO role.

Most of the companies he dealt with as an i-banker were large, mature companies.

DUDE Wipes was a high-growth startup. Creating a new category was not in his Deutsche Bank training manual. He wasn’t just doing spreadsheet kung fu. He was wrestling down invoices. Planning for future growth and putting in the framework for scaling a massive brand.

He was determined not to dilute their equity and made sure the only outside capital was the original check from Mark Cuban (on Shark Tank), until they hit escape velocity. He wasn’t just CFO. He was also the primary seed investor and line of credit for DUDE Wipes using his i-banking bonuses to bankroll working capital.

He wasn’t an ivory tower CFO, but an in the arena CFO. With big-time entrepreneurial skin in the game. He went to customer meetings with Walmart so he could look at the whites of the buyer's eyes before he spent precious working capital on inventory. He met with his co-manufacturers to make sure supply and demand were aligned.

Jeff trained himself to be crazy about cash flow.

Because early on, DUDE Wipes cash flow and Jeff’s cash flow were one and the same.

At DUDE Wipes, he helped design the rhythm between cash and creativity, supply and storytelling, and data and demand. The systems he once used to evaluate companies became the systems he used to build one from the ground up.

Then, DUDE Wipes hit its first of many supply-chain constraints.

The perfect storm of rising demand, retail expansion, and a thin cash position forced a moment every CFO knows too well: the numbers were “right,” and the business was tight. The Dudes needed to change. Every move the traditional finance playbook recommended (slow down POs, tighten spend, delay production) would have destroyed the momentum DUDE Wipes needed to survive.

Once the category sees it, they can’t unsee it. That new demand has to go somewhere. Had the Dudes failed to scale, they would have designed a category for someone else to dominate. And they knew it.

Jeff rejected the premise.

The legacy CFO model (close the books, manage cash, control the budget, protect the quarter) was useless for high-growth, consumer product category-creation. The category moved faster than the Dudes thought possible. And Jeff realized finance couldn’t be backward-looking anymore.

So, he focused on a different category of finance for category creators. Finance who think it’s their job to power the company to create a new category, not just hit their target.

Jeff built real-time visibility, tore out processes that slowed the team, and created a rhythm between free cash flow and creativity that kept DUDE Wipes alive and growing.

Jeff represents the future of finance leaders—the Agentic Chief Financial Officer.

This mini-book is about the shift from measuring financial performance to multiplying financial potential. In the post AI world.

You’ll see how Jeff’s ability to reject the premise has grown DUDE Wipes into a $300M+ company.

Because an Agentic CFO doesn’t just run the numbers. They orchestrate outcomes and turn finance from a rear-view function into the operating system for speed.

You’ll also see:

1. Why the old CFO model is collapsing, and the reason legacy finance functions slow companies down.

2. The new mental model of the Agentic CFO, and why free cash flow (not EBITDA) is the strategic metric of belief.

3. How to use AI agents to build financial intelligence and turn timing, demand, and cash flow into a self-reinforcing system of growth.

Whether you’re a finance nerd or you just want to understand how Category Kings approach a P&L, this mini-book will help you consider a different lens and mindset for finance.

So grab your ledger. We’re going on an adventure.

Why Finance Has A Category Problem

For decades, the CFO was trained to master the past.

The job was about precision—closing the books, reducing variance, and forecasting next quarter’s numbers with absolute certainty. It was a noble pursuit, built on the belief that control equals certainty. But that discipline hardened into dogma.

Finance became the department of no.

A world of careful gatekeepers guarding budgets instead of guiding growth.

Inside too many companies today, the financial system still runs on an inherited logic from the industrial era. The goal is predictability and risk mitigation, and the reward is consistency. CFOs are told to “protect shareholder value,” which often means keeping everyone else from making bold moves that might screw up the quarterly earnings report.

You can’t create a different future if your lens is to protect the status quo.

What began as a system for enabling growth became a system for containing it.

The traditional finance mindset was built for an economy of factories, not digital feedback loops.

It valued control because control was scarce. The CFO was the keeper of truth. The one person in the room who knew where every dollar went. That authority came with power, but it also created isolation.

As companies scaled, their financial systems scaled with them.

• ERP platforms got bigger, and reporting cycles got longer

• Forecasting became a quarterly theatre of variance explanations and budget revisions

• Somewhere along the way, the discipline of finance started to focus on compliance

When compliance becomes the culture, curiosity disappears.

Now don’t get us wrong. We’re very big fans of legendary governance. And controls are an important part of the job, but they are in service of producing legendary outcomes.

Most CFOs didn’t choose this system. Universities, consulting firms, and Wall Street all rewarded prudence, perfection, and predictability. Finance became fluent in accounting but lost its imagination.

A rigid mindset is dangerous when markets move faster than spreadsheets.

While startups run real-time AI-powered simulations, many large organizations are still waiting for last quarter’s reports to be finalized. Their data lives in silos. Their teams operate in sequence, not in sync.

By the time a financial insight arrives, the opportunity has already passed.

This is a category problem.

Finance has been defined by what it measures, not what it makes possible. It has been positioned as a back-office function instead of a front-line capability. And like any category that stays frozen too long, the world moves on without it.

The world doesn’t need more cost controllers.

It needs Creators.

The problem is the identity that the old system creates.

Traditionally, CFOs have been trained to slow the business down.

• The safest decision was always to say “no.”

• The least risky move was always to wait and see.

• The highest praise came from preventing something, not creating something.

Finance is the only function in a company where doing nothing is considered a win.

Marketing wants growth. Sales wants acceleration. Product wants innovation. Ops wants efficiency.

But finance wants the world to hold still long enough to reconcile it.

CFOs became guardians of the reporting cycle, instead of designers of the business cycle. They could do everything “right” according to the old playbook and still suffocate the company they were hired to protect.

This is the premise you must reject.

Because when a category demands speed, and your identity demands caution, you are structurally incapable of leading the company where it needs to go.

Which brings us to the future.

Milton Friedman’s Four Ways to Spend Money

In 1975, University of Chicago economist Milton Friedman laid out one of the most elegant frameworks for understanding spending behavior. He identified four ways to spend money:

1. Your money on yourself: Most careful about cost AND value.

2. Your money on someone else: Careful about cost, less careful about value.

3. Someone else’s money on yourself: Careful about value, less careful about cost

4. Someone else’s money on someone else: Not careful about cost OR value.

#1 is like when you buy your first house. #2 is a gift for someone. #3 is an expense account lunch. #4 is the government, with no care for cost or value.

That’s why the Pentagon has failed seven consecutive audits.

That’s why they can only account for 39% of their $3.8 trillion in assets. That’s why Donald Rumsfeld stood at a podium on September 10, 2001, and admitted the Defense Department “cannot track $2.3 trillion in transactions.”

Bernie Sanders called the Pentagon “the only agency that has never passed an independent audit.” Chuck Grassley complained about “$14,000 toilet seats” and “warehouses full of spare parts they’ve lost track of.”

Left and right agree: when nobody owns the money, and nobody owns the outcome, waste isn’t a bug. It’s the system working as designed.

Friedman’s insight was ruthlessly simple and can also be used to explain different CFOs!

We adapted Friedman’s framework to how CFOs actually behave—based on two variables:

1. Whose capital are they deploying? (Their own money or OPM—Other People’s Money)

2. What kind of category are they operating in? (A new category they’re creating with no competition, or an old category they are competing in)

Plot those two variables, and you get four distinct CFO archetypes:

• Your Money + New Category = ARENA CFO

• Your Money + Old Category = DIVIDEND CFO

• OPM + New Category = ENABLER CFO

• OPM + Old Category = GOVERNMENT CFO

Each quadrant produces a radically different relationship with cash, risk, and accountability.

The Arena CFO (Your Money + New Category)

This is Jeff Klimkowski.

His cash and DUDE’s cash were the same thing. That forces precision—you can’t be reckless because it’s your money, and you can’t be timid because the category is moving faster than your spreadsheets.

Friedman would recognize this as the most careful spending of all. The Arena CFO obsesses over both cost AND value because failure means personal loss, and hesitation means someone else defines the category.

Jeff has a goal of Zero Free Cash Flow at year's end.

What? Don’t you want more Free Cash Flow? You don’t want to be like Jeff Bezos and be negative Free Cash Flow and land-grab like crazy?

Not Jeff.

He wants DUDE Wipes to be perfectly calibrated at year's end. Not too conservative to the point of not investing enough to grow the category. He knew that if DUDE Wipes didn’t invest, the legacy category would persist and toilet paper would continue to cause Itchy Butt Syndrome for billions of anuses in the world.

But if he invested too far over their skis, they would need to raise money and dilute their equity. He was calibrating capital to reality in real time—because he couldn’t afford to do anything else.

Zero FCF is the financial equivalent of a surfer sitting in the pocket of a wave.

The Arena CFO doesn’t sit in the skybox watching the game. They’re on the field, their body on the line with every play.

The Dividend CFO (Your Money + Old Category)

In 2004, Microsoft’s CFO John Connors did something Wall Street hadn’t seen in decades: he announced a $75 billion capital return to shareholders—a one-time special dividend of $32 billion plus ongoing buybacks and dividends.

Why?

Because Connors recognized a hard truth: Microsoft had won its category. The PC operating system war was over. And a CFO sitting on a mountain of cash in a mature category has two honest choices: return it to shareholders, or admit you’re just bad at deploying capital.

Connors chose to return it. “Our shareholders can invest this better than we can,” was the implicit message.

By the way, when companies buy back their stock, they are also saying, “we’ve run out of ideas.”

This is the Dividend CFO. They are careful about cost as it’s still their shareholders’ money, but focused on returning cash because the category no longer demands aggressive reinvestment. Friedman would call this the “birthday gift” quadrant—you’re still watching the price tag, but you don’t invest because you don’t see any upside.

The Dividend CFO isn’t a failure. They’re realists. When the category is mature, the highest-conviction bet is to stop pretending you have high-conviction bets.

The Enabler CFO (OPM + New Category)

This is the WeWork playbook.

Artie Minson served as CFO during WeWork’s hypergrowth phase—the era when SoftBank’s Vision Fund was pouring billions into the company at valuations that defied gravity. Minson’s job wasn’t to create cash flow. It was to enable Adam Neumann’s vision.

When you’re spending other people’s money in a new category, the incentives bend toward optimism. The capital feels infinite. The category feels inevitable. Your job becomes processing spend, not questioning it.

Friedman would recognize this as the “expense-account lunch” quadrant. You care about value (you want the vision to succeed), but you stop caring about cost because the bill isn’t yours.

Minson wasn’t incompetent. He was operating exactly as the incentives predicted. When you have no skin in the game but believe in the destination, you become an enabler—processing capital toward a future that may or may not materialize.

WeWork burned through over $13 billion before reality intervened.

The Enabler CFO is seductive. They sound like visionaries. But without ownership, vision becomes vapor.

The Government CFO (OPM + Old Category)

This is the Pentagon with a P&L.

The Government CFO operates in the most dangerous quadrant: spending other people’s money in a category someone else defined. They have no ownership stake in the outcome, and no urgency to redefine the game. The result?

Process over purpose.

When GM took $50 billion in taxpayer bailout money in 2008, critics called it “Government Motors.” But here’s the truth: GM was operating like the government long before the bailout.

From 2020 to 2023, GM ran Super Bowl ads four years in a row—at $7 million per 30-second spot, running 60-90 second executions with A-list celebrities. Will Ferrell. Dr. Evil. Netflix partnerships.

The message? GM is serious about electric vehicles.

The reality? In 2022, GM sold just 39,096 EVs—less than 2% of their total volume. Most of the cars in those Super Bowl ads didn’t exist. A 2023 Newsweek headline captured it perfectly: “GM Makes Great Electric Car Ads, but Where Are the Cars?”

Meanwhile, Tesla spent $0 on advertising and dominated the EV category.

This is the Government CFO in action. Spending $3.25 billion annually on advertising. Knowing the trade promotion math doesn’t work. Knowing 35-40% of every CPG marketing dollar is wasted. But continuing anyway because... “we did it last year.”

Nobody gets fired for maintaining the status quo. Nobody gets promoted for questioning the orthodoxy. The safest move is always to process the budget, hit the benchmarks, and let someone else deal with the consequences.

The Government CFO isn’t evil. They’re just playing the game the incentives created.

The Question Every CFO Must Answer

Which quadrant are you in?

Not which quadrant you think you’re in. Not which quadrant your title suggests. Which quadrant do your actual incentives create?

Because here’s Friedman’s uncomfortable truth: you will behave according to your incentives, regardless of your intentions.

If you’re spending OPM in an old category, you will drift toward process. You will optimize for benchmarks instead of breakthroughs. You will protect the quarter instead of creating the future.

The only way to escape the Government CFO quadrant is to change the incentives:

• Create ownership. Tie your compensation to outcomes that matter, not activities that check boxes.

• Create urgency. Redefine the category or get redefined by it. The status quo is a trap, not a strategy.

• Create accountability. Build systems where cash flow tells the truth faster than anyone can hide it.

The Arena CFO doesn’t exist because Jeff Klimkowski has superior willpower. The Arena CFO exists because Jeff built a system where his capital and his category forced precision.

That’s the system the Agentic CFO designs.

The Agentic CFO: The Category Designer Of Free Cash Flow and Agency

Across industries, a new generation of financial leaders is emerging.

They still care about discipline, precision, and accuracy. But they’re also learning to work with a new kind of teammate—AI agents that extend their reach, speed, and intelligence.

Soon CFOs will manage more agents than people.

When AI can handle reconciliations, forecasts, and variance reports in real time, the CFO’s role expands. Finance becomes less about closing the books and more about opening possibilities. It becomes the company’s connection between data, decision, and direction.

Great CFOs don’t just close the books, they create maximum agency through finance. They remove barriers that slow free cash flow. They match supply and demand with more precision. They ensure the company is default alive, needs the least amount of outside capital possible, so the company can control its own destiny.

The Agentic CFO sits at the center of that shift.

• They turn numbers into signal.

• They orchestrate outcomes instead of transactions.

• They lead teams of human and digital agents to maximize cash flow control and enterprise agency.

They help the company move with clarity. Decisions that once took weeks now unfold in hours. AI compresses time, which means the future belongs to leaders who can see change early and act with clarity.

Does that mean all the legacy financial tools are worthless?

No.

But one of them is actively misleading.

Agentic CFOs focus on free cash flow, instead of EBITDA.

EBITDA (earnings before interest, taxes, depreciation and amortization) is a lie.

EBITDA is what Charlie Munger called, “Bullsh*t earnings.”

It makes bankers and board members feel safe because it smooths over the messiness of reality. It seems like a predictable metric. But that’s the problem.

• EBITDA hides operational rot.

• It rewards bad working-capital habits.

• It can make a company look profitable while it quietly bleeds out.

If EBITDA is the story you tell Wall Street, free cash flow is the story you tell yourself. That’s why legacy CFOs optimize for EBITDA and the reporting cycle. But Agentic CFOs optimize for free cash flow and the reality of the business.

Free cash flow tells the truth about your business.

It shows whether demand is real. It exposes whether growth is healthy or painful. And it shows whether the business is building momentum or burning through cash.

Free Cash Flow is basically three components:

1. Working capital. This is the baseline, day to day cash required to

   1. Make stuff you can sell (e.g., inventory)

   2. Pay people to help you sell it (accounts payable)

   3. Collect cash from your customers (accounts receivable).

2. CAPEX (Capital Expenditures). These are bigger investments needed to fuel the future

   1. For Analog/Physical businesses, this is manufacturing lines, warehouses, IT, etc.

   2. For Digital businesses, this is software development costs, R&D, etc.

   3. This can also be acquisitions of other companies you buy

3. Operating Cash Flow. This is the net cash your business generates from selling stuff

EBITDA says, “We’re doing fine.”

Free cash flow says, “Prove it.”

To understand why Agentic CFOs care about cash flow above all else, let’s look at three companies with amazing free cash flow.

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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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Dear Friend, Subscriber, and Category Pirate,

This episode is about the most undervalued skill in the world right now: thinking.

Not “consuming content” thinking. Not “I read a thread on X” thinking. Not “my algorithm told me what to believe” thinking.

Real thinking.

The kind where you sit with an idea long enough that it changes you.

We call this Thinker’s High.

Today, we’re talking about where it came from, why we turned it into a book, and why it might be the most important thing we’ve ever made—for you and for the people in your life who need Category Design but don’t know it yet.

This is the book you hand someone when they ask: “What is this Category Design thing you keep talking about?”

Gift it to your coworker. Your kid heading to college. Your work spouse for Valentine’s Day. (Eight days away. You’re welcome. Get it here.)

Or gift it to yourself so you can see the world through a category design lens every single day.

But first—a taste of what’s inside.

Three Proverbs. Three Ways To Think Differently This Week.

Every proverb in Thinker’s High comes with four layers:

• What (the idea)

• So What (why it matters)

• Now What (what to do today)

• AI Prompts (to jam on the idea with your AI co-founder).

Here are three from three different chapters:

“He or she who frames the problem owns the solution.”

(Chapter 1: Clarity—from the Position Yourself Or Be Positioned mini-book)

What: The person who defines the problem sets the terms of the game. If you frame the problem, you decide what matters, what doesn’t, and what the solution must look like. Everyone else is forced to play on your field. Think about Salesforce: instead of “CRM software,” they framed the problem as “the death of installed software.” That single move made “cloud” the only credible solution—and Salesforce owned it. The same is true in careers: if you’re the one who names the enemy and makes others see it, you become the obvious choice to solve it.

So What: Most people rush to pitch solutions. But in markets—and in life—the power lies in problem definition. Economically, whoever frames the problem first captures disproportionate value, because they shape how capital, talent, and customers flow. Emotionally, people rally around the person who says, “This is what’s broken, and here’s why it matters.” Culturally, movements are built not on shiny solutions but on reframed problems: climate change reframed as a climate emergency, phones reframed as life hubs, AI reframed as the new operating system. Own the problem, and you automatically own the path forward.

Now What: Stop pitching your product or résumé. Start framing the problem. Write a one-sentence enemy statement: “The real problem with [old way] is [painful truth].” Then create a FROM-TO contrast that makes the old way look obsolete and your way look inevitable. Use this language in every investor pitch, job interview, and customer conversation. Make your name synonymous with the problem you’ve defined. Once you do, the solution points straight back to you.

AI Prompts:

• Draft 5 FROM-TOs that make the old way obsolete and my solution space inevitable.

• Rewrite my pitch deck opener so it starts with the framed problem, not the product.

• Show me examples of legendary companies that reframed their market’s problem and won.

• Create a 7-day publishing plan that frames and names the problem I want to own.

“Reject the premise.”

(Chapter 2: Courage—from The Innovator’s Delusion mini-book)

What: Every category is founded on invisible assumptions. Coffee must be made one pot at a time. Dolls must be beautiful with great clothes. When it comes to vacuum cleaners, the more horsepower, the better. Most fail because they never question it. Keurig, American Girl, and Roomba all rejected the premise. “Disrupt yourself.” “Act like a startup.” “Build a skunkworks team.” These are smart strategies until you realize they’re based on the wrong premise. When you play by the wrong rules, you don’t just lose—you disqualify yourself from the game you were built to win.

So What: Following the default playbook leads to default results. Startups win because they reject the premise. Incumbents can stay the Category King by rejecting the premise as well. Amazon rejected the premise by niching down on e-commerce books. After they became the Category King of e-commerce, they rejected the premise of being a retailer via Amazon Marketplace, allowing competitors to sell on their platform. Janus Motorcycles is thriving at a stunning 62% growth rate in a mature market. Why? Janus has crafted a unique motorcycling experience called “rambling.” This isn’t just about hopping on a bike; it’s about embracing the journey and ditching the daily grind for a leisurely adventure on two wheels. Because they’re not competing on speed or price. They’re redefining what riding can mean—creating a new niche and attracting loyal Superconsumers who want more than just a commute.

Now What: Question everything. It takes asking ‘why’ seven times like an annoying toddler until you can actually see the fundamental premise with clear eyes. Gather your leadership team and identify one dominant industry belief you want to reject. Then, reframe the conversation. The companies that win don’t adapt to the narrative. They rewrite it.

AI Prompts:

• What assumptions are we operating under that might no longer be true?

• Are we solving a problem—or reacting to someone else’s framing of it?

• What industry dogma do we need to reject to play our own game?

• If we designed the rules from scratch, what would they look like?

“Marketing that does not produce revenue is called arts and crafts.”

(Chapter 5: Marketing—from The 3 Marketing Metrics To Rule Them All mini-book)

What: Marketing isn’t decoration—it’s a weapon. If your campaigns aren’t driving pipeline, closing deals, or creating exponential word-of-mouth, then they’re not a strategy. They’re theater. The job of marketing is to generate belief that moves the market—and belief that moves the market should move revenue. Otherwise, you’re just coloring inside the lines and calling it growth.

So What: Too many teams treat marketing like a cost center or a brand awareness sandbox. They chase vanity metrics, polish taglines, and publish content that makes the team proud—but not the cash register sing. The result? Bloated campaigns, budget cuts, and a credibility gap with the CEO. Marketing isn’t about activity. It’s about acceleration.

Now What: Audit your marketing backlog. What projects are tied directly to revenue outcomes, and what’s just brand therapy? Rebuild your roadmap around Lightning Strikes that generate attention, word-of-mouth, and strategic pipeline. Tie every campaign to a dollar goal and a belief shift. If it doesn’t move revenue, cut it or fix it.

AI Prompts:

• Which of our current marketing activities directly drive revenue, and which don’t?

• What belief do we need to create in the market to accelerate deals?

• How can we turn our next campaign into a Lightning Strike that generates revenue now?

• If we had to cut 80% of our marketing, what 20% would we keep because it pays?

That’s 3 out of 52.

Each one designed to stop you mid-scroll and start you mid-thought.

(Already know you need this on your coffee table? You can get it here.)

Thinking About Thinking Is The Most Important Kind Of Thinking

Everyone’s scrambling to learn prompts. Watching tutorials. Optimizing what they feed AI.

Nobody’s asking: What am I actually thinking—and why?

There’s a difference between reflexive thinking and reflective thinking. Reflexive is fast, automatic, unquestioned. It makes you feel productive while you recycle the same ideas everyone else has. Reflective is where you pause and ask: Where did that belief come from? Is it a fact, a filter, or a feeling?

Most of us were taught what to think our entire lives. By school. By media. By marketing.

Thinker’s High is what happens when you pierce through being told what to think and start doing the thinking yourself.

It’s the dopamine hit you get when you shift from consuming ideas to generating them. Shaping them. Turning them into value that changes someone’s life.

Once you experience it, you get addicted. You start asking “why” five to seven times. You start realizing the assumptions you had were never yours. You start designing new futures instead of decorating old ones.

It’s a runner’s high for your mind. Except the more you do it, the more valuable you become.

Why A Book Of Proverbs (Not Another Mini-Book)

We’ve written over 200 mini-books.

Some of our best lines—the ones we come back to in our own jams, the ones Pirates quote back to us—get buried inside 10,000-word pieces. Highlighted once. Never found again.

So we asked: what if we extracted the sharpest lines across everything we’ve ever written and built a book designed to be used, not read?

We started with AI. Ingested all 200+ mini-books. Extracted roughly 4,000 candidate quotes. Built a scoring system. Then we went in as humans and picked the 52 that made the final cut.

10 chapters: Clarity. Courage. Treasure. Creativity. Marketing. Relationships. AI. Future. Simplicity. Legendary.

Open any page. Find what you’re looking for. Start thinking.

👉 Order your copy of Thinker’s High here.

Here’s how to navigate this conversation:

• 00:00 – What Is Thinker’s High? The origins of the concept and why human thinking is the most important skill in the age of AI.

• 04:59 – Thinking About Thinking: Why most of us have been taught what to think, not how to think—and why that distinction changes everything.

• 08:39 – The 10 Chapters: How we organized 52 proverbs across clarity, courage, treasure, creativity, marketing, relationships, AI, future, simplicity, and legendary—and how to use each one when you’re stuck.

• 11:47 – How We Used AI To Write This Book: We cranked the dial to 11, extracted 4,000 quotes, and learned what AI can and can’t do in the book creation process. A behind-the-scenes look at the process—useful for anyone writing books with AI.

• 14:57 – The Gift Strategy: Why this book was designed to be gifted—and why gifting is the most underused superconsumer strategy in the world.

• 15:24 – The Richard Bach Inspiration: How Pirate Christopher’s favorite childhood book inspired the serendipity design of Thinker’s High.

• 17:53 – Why It’s Not On Amazon: We walked away from the largest book retailer on earth. Because we practice what we preach.

You won't find it on Amazon.

On purpose.

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Category Pirates 🏴‍☠️

Eddie Yoon

Christopher Lochhead

P.S. - Each proverb comes with AI prompts designed to be jammed on with the Pirate Eddie Bot.

The prompts work with any AI.

But they work best with the Pirate Eddie Bot—who’s trained on our entire mini-book library and can take the proverb deeper, apply it to your specific business, and walk you through the full framework behind each quote.

Book + Eddie = the full Thinker's High experience. If you're a Founding Subscriber, you already have the Pirate Eddie Bot. If you're not, now you know what you're missing.

Join the inner circle here.

P.P.S. - This is Volume 1.

There will be a Volume 2. Probably a Volume 3. We’re building a collector’s set because words matter and the more mini-books we write, the more legendary quotes we extract. But this is where it starts.

Get your Volume 1 copy → CategoryPirates.store

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 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:

Read more

Arrrrr! 🏴‍☠️ Welcome to a 🔒 subscriber-only edition 🔒 of Category Pirates. Each week, we share radically different ideas to help you design new and different categories. For more: Audiobooks | Category design 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,

In Part 1 of Marketing As A Profit Center, we showcased how Tesla is using its new rental car business as profit-positive marketing for everything else.

In Part 2 of Marketing As A Profit Center, we showed how others are doing it and the true cost of Marketing As A Cost Center mindset.

Here, we show you the way out.

Because climbing the value ladder isn’t just an economic shift. It’s a transformational shift.

Companies don’t stay stuck at the bottom because the marketing team lacks ideas. They stay stuck because the system around marketing (the calendar, the politics, the budgeting rituals) is designed to keep them grounded.

Every organization has gravity, and most leaders mistake it for strategy.

Gravity always pulls toward the familiar.

Most marketing organizations are prisoners of the calendar. Plans locked months in advance. Optimized around buying media, filling channels, delivering impressions. But the calendar is a product of the lower rungs of the value ladder—where activities scale linearly with spend, and the safest move is to spread dollars wide enough that no single bet can be blamed for failure.

If you want marketing to ascend, you have to break this gravitational field

The 5 Step Playbook To Turn Marketing Into A Profit Center

Most marketers know something is wrong. Fewer know where to start fixing it.

The answer isn't better tactics—it's a different operating system.

One that changes how you talk, what you focus on, what you sell, and how it all connects.

Let’s jam. 🎸🏴‍☠️

Step 1: Stop Talking Like A Cost Center

George Carlin had the seven dirty words you can’t say on Television.

Pirate Christopher wonders why George Carlin stopped at seven?

The words you use shape how others see you.

When a CFO hears “marketing budget,” they hear “expense.” When they hear “marketing capital,” they hear “investment.” This isn’t semantics—it’s positioning. And if you can’t position yourself internally, you have no business positioning anything externally.

Marketers, there are seven dirty words you must no longer say in marketing.

Dirty word #1: Budgets

Nothing says cost center more than ‘my marketing budget’. Budgets say, “This is mine to spend.” Budgets create a ‘spend it or lose it’ mindset. Budgets create entitlement at annual planning time. This is how kids think about their allowances.

The word you want is Capital.

Capital forces you to think like a VC or PE fund. Your Board, CEO, and CFO are your Limited Partners (LPs), who have entrusted you with capital to grow.

Dirty word #2: Calendar

The moment we hear a marketer say “marketing calendar,” we know this is a peanut butter marketing situation. The marketer lacks courage and conviction and defaults to small bets that no one will blame them for.

The words you want are Lightning Strike.

Lightning Strikes create immediate revenue and word of mouth. Strikes can turn cost centers into profit centers. Do the category design work and augment it with Category Science, and you’ll have no fear.

Dirty word #3: Brand Awareness

When a marketer says we’re spending to build awareness, it’s a tell that they are about to light some money on fire. This is because most marketers fixate on building awareness of their brand or product.

The words you want are Problem Awareness.

Market a consumer’s problem, and they think you want to help them. Market your brand, and customers think you want their money.

Dirty word #4: Reach

No one cares how many people your marketing reached. Oh, so your creative flashed before a person who is multi-tasking, flicking between silly animal videos, and isn’t even in the category? Oh, you reached one million of these? See if your CFO cares.

The word you want is WOM.

Word of mouth creates more word of mouth. How many superconsumers are able to remember your problem and POV and repeat it to someone else? WOM trumps reach every time.

Dirty word #5: Impressions

No one cares how many people saw your marketing. Pirate Christopher has seen Pirate Eddie’s blue minivan on the Big Island many times. He’s ridden in Pirate Eddie’s blue minivan many times. Now, picture Pirate Christopher buying one. LOL.

The words you want are Installed-Base.

Great businesses don’t have customers or transactions, they have an installed base of Supers that they can easily market and sell to. Apple estimates the global iPhone user base is ~1.5 billion. Now that’s an installed base.

Dirt word #6: Campaigns

A campaign is a one-off event. One-off events don’t build momentum. One-off events don’t become assets. One-off events are and will always be a one-time expense that you can never get back.

The word you want is Flywheels.

Not funnels of campaigns. Your marketing must drive a Super to buy and get an outcome, which leads the Super to talk about the outcome, which leads more Supers to buy. Forever.

Dirty word #7: Brand Equity

Do brands matter? Of course. But too many marketers have fallen prey to the Big Brand Lie. They focus on brand awareness and equity metrics. They worry about making the logo bigger and pantones.

The word you want is Category Potential.

Are you building awareness of the new category and the problem it solves? Are you converting legacy supers to the new one? Categories make brands.

To reject the premise, you must reject the legacy language.

To change your language, you must change how you think.

To change how you think, you must change what you do.

If you change what you do, you will change the outcomes you enjoy.

Let’s get specific.

CMOs! It’s time to change the power dynamics between you and your C-Suite brothers and sisters. Aren’t you tired of the side eye glances when your marketing budget is flashed on the screen? Can’t you hear the thought bubbles?

• “Marketing budget. What a waste of money.”

• “I need the CMO’s budget. What are they thinking?”

• “We’d be better off buying lottery tickets than letting marketing light that money on fire.”

Here’s the secret that most CMOs miss:

Self-funding marketing changes power dynamics.

Do you remember the look on your parents’ faces when you, as an adult, picked up your first-ever dinner check? It’s a look of surprise and eventually a smile of satisfaction so deep you never forget it.

It’s the same look a CFO gives the CMO when the CMO says, “I can self-fund this. Don’t worry.”

The moment marketing clearly and transparently produces revenue directly (ticket sales, sponsorships, subscriptions, deal flow, ecosystem gravity), it stops being a “cost” and becomes an investment.

When marketing behaves like a business, it doesn’t need permission—it creates leverage. Revenue-driven marketing builds its own flywheel: money funds momentum, momentum funds belief, belief funds growth.

The more revenue marketing drives, the more optionality the company has—and the less marketing gets treated like a service department begging for headcount.

This is the line between marketing as decoration and marketing as destiny.

One burns cash and patience.

The other earns reinvestment and authority.

Step 2: Find & Focus On The Niche Of Your Core Business.

Every business has a core—the part that funds everything else.

At Amazon, it’s AWS: 17% of revenue, 60% of profit. At Apple, it’s iPhone. At Alphabet, it’s Search. These are the core businesses that fund everything else.

But you don’t have to be a trillion-dollar company to have a core. Even simple, one-category businesses have power SKUs and super-geos—the products and places where disproportionate value concentrates.

Take Ben & Jerry’s. At one point, Cherry Garcia was their #1 flavor. And two decades ago, just 3,000 out of 30,000 grocery stores accounted for over half of Cherry Garcia sales. The consulting recommendation wrote itself: don’t be out of stock in those 3,000 stores.

Not every CMO knows this.

Not every CEO knows this.

But most CFOs know this very well.

And the fastest way to get buy-in from the CFO is to ask, “What is our core business?” and market that. But answering, “What is your core business?” is not always as easy as it seems. Category Pirates defines your core business as the part of your business that:

• It is the centerpiece of your enterprise value (e.g., investors care the most about it)

• You have a powerful marketing flywheel that drives LTV and low CAC

• You are the Category King (76% of category economics)

• You are different in your product and/or business model

• Your supers get massive outcomes & drive WOM

• Aligns with the core problem to solve and POV

• Gets simpler over time

Your core can hide at different altitudes. Sometimes it’s a category. Sometimes it’s a category in a specific country. Sometimes it’s a single product, in a single market, in a single channel.

Take Colgate-Palmolive.

They operate in Oral Care, Pet Care, Personal Care, and Home Care.

So what’s the core?

Your first instinct might be Oral Care or Pet Care—both are #1 share positions where Colgate is the Category King. Both have strong marketing flywheels, powered by endorsements from dentists and veterinarians.

But the real answer is more specific: Oral Care in Latin America.

That’s where Colgate dominates market share. That’s where population and per capita income are trending up for decades. That’s what fuels Colgate’s dividends for the foreseeable future.

If your company has one category, one brand, one product—this exercise is straightforward. But for larger companies with many brands across many categories, finding the core takes real work.

Chris Zook’s Profit From the Core is one of Pirate Eddie’s favorite business books.

Zook defined your core as the part of your business where you have the deepest, most defensible advantage. Where your most profitable customers live. Where operating leverage compounds.

Put simply, it’s the system of products, customers, and capabilities that produces the majority of your profit with the least complexity. Everything sustainable grows from there.

His team at Bain did the Category Science to prove it. They studied mega-brands—companies with multiple products and categories under the same brand—and found something striking.

Zook found two things.

First, most mega-brands had one core business where they were the Category King. Not two. Not five. One.

Second, companies that were Category King in their core generated more than 2x the return on capital versus other mega-brands.

Dominance in your core isn’t a nice-to-have. It’s the whole game.

Why do we know this question is hard to answer? Because Category Pirates are still wrestling with it ourselves. More on that later.

Step 3: Launch An “Experience” Event For Your Core Business

Most companies treat events as brand building.

That is code for “who knows if this works?”

It’s arts and crafts with a bar tab.

Here’s how category designers think different:

Read more