The Best Of Category Pirates 2025

How we became an AI-first startup and had our best year ever

Arrrrr! 🏴‍☠️ Welcome to a 💎 free edition 💎 of Category Pirates. Each week, we share radically different ideas to help you design new and different categories. As a paid subscriber, you get access to an archive of 99+ mini-books, audiobooks, jam sessions, and every future post.

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Dear Friend, Subscriber, and Category Pirate,

We want to give a hearty thank you to Pirate Katrina as she sets sail on her own pirate ship, niching down within Category Design.

We are very excited for her and grateful for all she’s done, including helping us launch the Category Design Academy, Strategy Therapy, and Creator Capitalist courses. Each of those has made a big difference in helping you, our category design community, and with our mission: to unleash 100,000 category designers into the world to unlock massive abundance.

She not only helped push the digital wheelchairs of two Native Analogs, but helped us bridge Category Pirates from a teaching business into the transformation business.

We are excited to see what is next for you, Pirate Kat!

We are also stoked for new Pirates on the Pirate Ship!

Pirate Bri is captaining the pirate ship, overseeing all operations. Pirate Chris Stanley is helping us streamline and speed up our Big Book publishing. Pirate Jack is our AI Agent creator and vibe coder who is helping us rebuild Category Pirates as an AI-first business.

Our Pirate Interns continue to punch far above their weight: Pirate Miya leads audiobooks, Pirate Keegan works on AI addendums and agent training, Pirates Julien and Audrey support our Thinker’s High AI writing process, and Pirate Luke builds automations and infrastructure, and more.

2025 ended up being Category Pirates’ best year ever.

Thank you. 🙏

But it sure as hell didn’t start that way.

In the first half of the year, Pirates Christopher and Eddie had enough heated conversations to worry neighbors. At one point, Pirate Christopher’s wife even asked, “Are you guys… okay?”

The answer: Yes. Obviously.

These two lunatics plan to build, teach, and lead category transformations together until they keel over on their keyboards (and keep going on the other side of Heaven). Anger isn’t a problem for Pirates. It’s Pirate Christopher’s happy place. Anger is commitment wearing a leather jacket. Anger is love that gives a sh*t.

There was plenty to be angry about.

Q1 2025 was the first down revenue quarter in Category Pirates history.

The dollar amount wasn’t the issue. The signal was.

Something in the business was waving a giant red flag.

We had to stop pretending everything was fine and drink our own rum. Pirates can’t preach transformation if we’re not also in the arena getting punched in the face with everyone else.

So Pirate Eddie (reluctantly, heroically) became CFO.

Within a week, he was doing spreadsheet kung fu and uncovering stupid everywhere. (Pro tip: every plan in the world contains at least 10% stupid. Ours was closer to 20%.)

He even found a finance contractor we were paying thousands a month, whom neither Pirate could actually identify. When Eddie finally called the guy and asked, “Hey man, what do you do here?”, the guy replied, “Not much. You should stop paying me.”

Legendary answer. Months too late, but still legendary.

Once Eddie cleaned up the math, the story became obvious:

• Category Pirates looked like it was growing
• The growth was coming from shiny new toys (Category Design Academy, Strategy Therapy, etc.)
• While our Substack (the origin of the business) was flat-to-declining

We were chasing new shiny new toys, instead of asking the uncomfortable question:

What broke?

That’s when Pirate Christopher unleashed one of his trademark rants. Eddie (eventually) realized the rant wasn’t about him. It was about the situation. Rage is Pirate Christopher’s creative medium. Others paint with watercolor. Christopher paints with fire.

Then came the second fight.

A Korean Fire Chicken Noodle–level fight.

The topic? AI.

Both Pirates agreed AI was the biggest shift of our lifetimes. Both agreed we needed to rebuild Category Pirates from scratch. As AI-first, AI-native, AI-powered.

But they disagreed on one thing:

What is the next first step?

Christopher wanted speed. Eddie wanted clarity. Neither was wrong. Both were annoyed.

Perfect conditions for a breakthrough.

You can’t have breakthroughs without breakdowns.

It turns out AI wasn’t just “important” to the Pirate Ship.

AI was the wind in the sails, the tide under the hull, and the cannon that blew the doors off 2025.

Our ten most-read pieces of the year proves the point:

1. The Pirate’s Guide To AI: How To Build With AI Like It’s The Greatest Co-Founder You’ve Ever Had

2. 6 Steps To Turn ChatGPT Into A Category Design Co-Founder

3. Category Manifesto: 8 Steps To Frame Your Idea, Name The POV & Claim A Category

4. Creator Capital: It’s Time To Transition From Knowledge Worker To Creator Capitalist

5. Radical Agency: A Proven Framework For Taking Control Of Your Career, Money, And Financial Freedom

6. Intellectual Capital: 5 Ways To Turn Your Knowledge Into Content That Makes Money While You Sleep [Part 1]

7. Intellectual Capital: 5 Ways To Turn Your Knowledge Into Content That Makes Money While You Sleep [Part 2]

8. Reputation Capital: How The Currency Of Differentiation Creates Lifelong Opportunity

9. Vibe Creating: Why Building With AI Starts With Being As Human As Possible

10. The Big Retirement Lie: What The Financial Services Industry Doesn’t Want You To Know (And How To Design A Career Worth Doing For Life)

At first glance, it looks obvious that AI content wins. But the real through-line isn’t AI.

It’s transformation.

Transformation from doing what you’re told → creating what only you can create

Transformation from digital → AI-first

Transformation from who you are → who you were meant to become

This wasn’t a year of “learning.” This was a year of category redesigning our whole business.

Transformation is not teaching. People confuse “teaching” with “transformation” the same way they confuse a gym membership with abs.

Teaching is passive.

You sit.

You nod.

You listen.

You forget.

Transformation is confrontational.

You get rocked by brutal honesty.

You get inspired by radical courage.

You take a leap of faith, scared out of your mind.

You become who you were meant to be, making a difference for others that only you can make.

Are you ready to get in the arena and bleed for the outcome?

Most books are teaching books.

They are $20–$30 commodities.

You read them in a one-way conversation.

Our Lightning Strike Marketing book is the opposite.

It’s a book about transforming marketing from the way it was to the way it was meant to be, an unstoppable revenue and word-of-mouth-generating machine. They can be priced at $100 plus because they generate 1,000x return on investments.

It’s a two-way conversation, where the book reads you and asks you, “So, are you actually going to do this, or not?”

It’s $100 because it’s not a lesson.

It’s a lever. A push. A dare.

It comes with diagnostics, scorecards, AI prompts, and a framework that forces you to build a marketing system that generates revenue now and word-of-mouth long after.

So when we got our first one-star review, we celebrated.

Why?

Because the review revealed the exact misconception we’re fighting:

• They valued the book, not the outcome.

• They think books are commodities like textbooks.

• They only see audacity in the $100 price tag, not transformation value.

Everything we value, we were taught to value.

Many people were taught to value the wrong things.

If you’re sitting in the audience, $100 feels expensive. If you’re in the arena, trying to drive revenue this quarter, $100 is a rounding error on your way to a monster outcome.

(And yes, our next big book, Thinker’s High, is next. It’s almost here. Buckle up.)

Just ask the DUDE Wipes crew (Sean, Ryan, and Jeff) who:

• Leave half their marketing calendar open for spontaneous Lightning Strikes.

• Run marketing through their proprietary A–G system to drive word of mouth.

• Treat marketing like a M&A deal team, not a coloring book.

• Negotiate for creative freedom like pirates, not vendors.

• Buy sponsorships for cents on the dollar.

No other book explains their strategy. Nobody is teaching this in a class.

The DUDES are a one-of-one.

That’s the whole point. Transformation isn’t about learning someone else’s tactics. It’s about becoming someone new.

This was the moment the fog lifted for us.

We always thought of Category Pirates as a writing band.

Turns out we’re not (just) authors.

We’re agents of change.

People don’t come to us for ideas. They come to us because they want to create different futures.

AI made that brutally obvious.

In teaching mode, AI is an assistant. It edits drafts. Cleans structure. Polishes logic. AI is nice, helpful, and secondary.

In transformation mode, AI becomes a main character.

It was time to re-imagine how AI could deliver value to our Substack subscribers, who were and are the heart of our business. And it was relationship capital that made it possible.

Pirate Al Ramadan was incredibly helpful here, sharing what he had done training his personal ChatGPT and what he did with Delphi.ai. Pirate Eddie took Delphi and reached out to Pirate Jack Bigbee, a bad-ass vibe coder he worked with previously to develop a new product.

Pirate Eddie got to thinking about Superconsumers and thought that maybe, just maybe, the Pirates should have paid attention to the Founding Subscription tier on Substack.

So we put it together: Delphi + Pirate Jack + Founding Tier = the Pirate Eddie AI bot.

And guess what?

• Founding Subs grew 25 times in 6 months.

• Substack ARR kick-started back to growth.

• Substack cash flow grew even faster and higher than Substack reported ARR.

(More on that in a future mini-book, but suffice it to say that Substack needs to get better at math.)

So we folded AI into our other product offerings:

We converted much of the Category Design Academy curriculum to AI agents and bundled it with the Pirate Eddie AI Bot for a record-high Academy 3.0 cohort.

We used AI to launch big books faster and more powerfully, moving from one big book every year to three to four.

Category Pirates had its highest MRR in November 2025. If that trend continues, Category Pirates will double in 2026.

The Pirate Eddie AI Bot doesn’t help you write.

It helps you think.

It argues with you.

It challenges you.

It tells you the truth your inner coward is hiding from.

Pirate Donald Hawthorn (big-time CEO, board member, transformation ass-kicker) has been sparring with Pirate Eddie inside Category Design Academy 3.0.

One day, Eddie drops a breakthrough insight. It was an emotional, EQ, insight, not a rational, IQ, one.

Don laughs and says:

“Pirate Eddie Bot told me that two months ago.”

That’s when it hit us that we weren’t being replaced.

We were being multiplied.

That is the purpose of AI in transformation.

AI doesn’t make you smaller.

It makes you bigger.

The biggest lie in modern learning is that transformation comes from being taught.

Joe Pine wrote one of the best bars in the entire business writing canon.

You can read it in his Substack on Transformations here (and you should absolutely subscribe).

Here’s the a-ha:

In a transformation, the protagonist is not the teacher.

It’s you.

That single idea reframes everything.

AI isn’t here to do the work for you. It’s here to equip you to become someone capable of work you previously thought impossible. The work still belongs to you. The change still belongs to you. The outcome still belongs to you.

That’s exactly how we think about the Category Design Academy, now heading into yet another year as our highest-level transformation offering.

The Academy isn’t about consuming frameworks or memorizing ideas. It’s about watching people become different—using Category Design to redesign their work, their identity, and their future in real time.

And once again, the Pirates inside the Academy delivered.

Take Pirate Melissa.

Her category is Digital Darkness—the invisible reality that 68% of farms have no cell coverage. By framing, naming, and claiming that problem, Melissa became the Category Queen of connecting rural farms to technology. She didn’t sell software. She sold time—helping farmers reclaim hours they could invest back into their businesses or back into their families.

Hear Melissa walk through her transformation, in her own words, here:

Or Pirate Pablo, now the undisputed King of Relationship Capital.

Pablo took social capital and digital word of mouth and elevated them into a category of their own.

The result?

He more than doubled his income and was recruited by a fast-growing AI property management company—not because he chased opportunities, but because his category pulled them toward him.

Listen to Pablo explain how relationship capital became his category—and his growth engine—right here:

Then there’s Pirate Thomas.

He thought his category was UK expansion. It wasn’t.

Through the Academy, he realized he was the Category King of Contribution Margin. That single reframing paid for the Academy in one month and filled his consulting dance card for the next one to two years at 8curve—without chasing fake growth or vanity metrics.

Listen to Thomas walk through the moment he stopped chasing growth and started owning contribution margin:

And Pirate Nick turned a layoff into a category.

No resume. No job hunt.

He framed a new lane—How Solos Scale—learned how to spot and act on real market signal, and turned an idea into $30K in one weekend.

Hear Nick tell the story of how he turned a layoff into a category—and made the job hunt irrelevant—here:

We love these pirates. And we want more transformation and more different futures as fast as possible.

So we asked:

• What if we trained our AI on other legendary Creator Capitalists?

• Would transformations grow faster?

We think so.

Transformation accelerates when you stop learning from theories and start learning from legends.

One of the fastest ways to accelerate transformation is to learn from people who’ve already done it.

That’s why, after watching another year of Category Design Academy pirates transform their work and identity, we asked a simple question: What if we trained our AI on legendary Creator Capitalists—people who’ve already figured out how to turn thinking into leverage, categories into careers, and ideas into enduring capital?

The result is a growing library of conversations designed to do one thing: collapse the distance between insight and outcome.

And as a bonus, we’ve got you covered for the holidays.

If you’re looking for an escape from a boorish family member (or a thoughtful escape), we’ve got some podcasts for you:

Joe Pine is a living case study in Creator Capitalism.

He didn’t just write The Experience Economy and The Transformation Economy—he built an entire solo consulting business by turning his thinking into leverage and positioning himself as a guide to identity change.

In this conversation, we focus on: why writing creates clarity, how leaving a dominant company unlocked his category, and why transformation always starts with who you become—not what you buy.

Highlights:

• 06:06 – Books as Credential Capital: Joe explains how getting published by Harvard Business School Press and HBR positioned him as a trusted expert.

• 16:45 – Building Strategic Horizons: How meeting Jim Gilmore led to a legendary partnership and their co-authored category-defining work.

• 33:00 – Transformation Is Identity Change: Joe unpacks the core idea of his new book: All meaningful change begins with identity.

Rafi Mohammed didn’t build a career selling time—he built one by reframing how the world thinks about pricing. Through books, HBR articles, and a clear POV, he turned pricing into a category and created a business that pays for judgment, not hours.

This conversation unpacks how pricing is emotional, not mathematical—and why “earnership” is the real moat for Creator Capitalists.

Highlights:

• 09:40 – Pricing Isn’t Math. It’s Storytelling: Rafi explains why value is always relative, and how price signals shape customer expectations before they ever buy.

• 26:30 – Category Pricing in Action: From good-better-best models to reframing value, Rafi walks through how he helps clients escape the pricing trap.

• 57:45 – Why “Best” Is the Real Opportunity: Rafi breaks down why Superconsumers want to buy your most premium offering and how to let them.

Mike Maples Jr. has done what very few people do—successfully reinvented himself multiple times. From entrepreneur to VC to AI co-founder, Mike has consistently optimized for being the only, not the best.

This conversation is a masterclass in designing a career around comparative advantage and turning thinking into scalable capital.

Highlights:

• 00:40 - Burn Your Resume: Hear why Mike turned down millions to start from zero on his terms—and what it takes to make a big bet on yourself.

• 10:20 - Turn Thinking Into Capital: How Mike created an AI-driven system for scaling his intellectual capital—and why he thinks AI is a must-have skill for anyone who wants to excel and drive exponential outcomes.

• 20:45 - Credentialism Is Dead: What mass cognition is and why it makes creators more valuable than experts.

Monroe Jones built a legendary creative career not by chasing outcomes, but by disappearing into the work.

From a small town in Mississippi to producing for U2, Stevie Nicks, and David Crosby, Monroe’s story is about patience, generosity, and compounding creativity over decades.

This conversation reframes creativity as a long game—and slow dopamine as the most valuable currency creators have.

Highlights:

• 20:31 – Slow Dopamine in Action: Why creativity equals freedom, how to access the “bliss of self-forgetfulness,” and the reason real work compounds over decades.

• 31:25 – Inside the Studio with Legends: Monroe takes us behind the scenes with U2, Stevie Nicks, and David Crosby.

• 52:44 – Everyone Is Creative: The truth about why creativity is never scarce and how to find and trust your own unique stamp.

As we look ahead to 2026, we’re doubling down on what we now know—without question—to be true:

Category Pirates is a teaching and transformation business, built AI-first.

AI isn’t an add-on.

It isn’t a tool on the side.

It’s our co-founder.

And when AI sits at the center of the business, everything around it accelerates.

Thanks to Pirate Bri Clark, Pirate Chris Stanley, Pirate Jack Bigbee, and our intrepid interns, we’ve rebuilt the engine under the hood. What that unlocks for you shows up in three very real, very practical outcomes.

1. Helping You Turn Category Design Into Revenue You Can Count On

The core cadence you know isn’t going anywhere.

You’ll still get bi-weekly mini-books and the thinking you’ve come to expect. Layered on top of that, you’ll still see Founder’s Posts—shorter, sharper, and more behind-the-scenes. Content about the content. More practical. More tactical. More “here’s exactly how we’re using AI right now.”

What is changing is speed.

For the first time, we can reliably produce three to four big books per year—not as one-off heroic efforts, but as part of a continuous system. That means long-awaited projects finally come to life: Creator Capitalist (for real this time), The Agentic Executive, Snow Leopard Part Two (including the business model behind the $100 book), Thinker’s High: Volume One And Two, and more—including expanded Pirates Guides to AI.

All of it is designed with a single outcome in mind: helping you turn Category Design into revenue you can actually count on in 2026.

2. Removing The Bottlenecks That Slow Category Designers Down

One of the biggest lessons of 2025 was this: AI doesn’t just make things faster—it removes friction entirely.

Writing no longer has to be the bottleneck.

Publishing no longer has to be the bottleneck.

Turning ideas into intellectual capital no longer has to be the bottleneck.

In 2026, we’re designing for a world where anyone can become an author with AI. Where anyone can systematically build, refine, and compound intellectual capital over time. That’s why we’re relaunching our courses with AI woven directly into the experience—not as “bonus material,” but as the core engine.

Strategy Therapy plus AI. Creator Capitalist plus AI.

And a growing suite of Category Design–specific agents—Lightning Strike Agents, Category Manifesto Agents—designed to help you move from thinking to execution faster than ever before.

Less friction. Less waiting. More momentum.

3. Creating The Space To Take Bigger Bets

Once revenue grows and bottlenecks fall away, something else opens up: permission.

Permission to experiment.

Permission to take more swings.

Permission to explore ideas you would’ve ignored before because they felt too risky, too slow, or too uncertain.

That’s where 2026 gets really fun.

Expect new AI copilots—including a very on-brand, very unfiltered Pirate Christopher bot (yes, R-rated). Expect deeper Category Design Academy content that doesn’t just teach frameworks, but shows how those frameworks evolve in real time. And expect more hands-on workshops focused on Lightning Strikes, pivots, and scaling—designed to help you actually execute, not just understand.

Not to transform you for you.

But to equip you to build your own version of what comes next.

If 2025 was the year we rebuilt the engine, 2026 is the year we stop asking “if” and start testing “how far.”

Get ready for a legendary year!

Up next: A mini-series on Marketing As A Profit Center in 2026 and beyond.

Arrrrrr,

Category Pirates 🏴‍☠️

Eddie Yoon

Christopher Lochhead

P.S. – If this year made it painfully obvious how little independent thinking the world actually rewards, good.

That sensation has a name.

Thinker’s High.

It’s our next book, and it’s built for people who refuse to outsource their thinking—to trends, tools, or the loudest voice in the room.

Fifty-two provocations. One per week.

Not to teach you what to think—but to wake up the part of you that still can.

Launching soon. 🏴‍☠️