(2025-12-26) The Best Of Category Pirates2025

The Best Of Category Pirates 2025.

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.

2025 ended up being Category Pirates’ best year ever.

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

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

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

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%.)

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*

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.

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

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

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 $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.

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.

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.

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.

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

And guess what?

Founding Subs grew 25 times in 6 months.

Substack ARR kick-started back to growth.

So we folded AI into our other product offerings

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

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

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.

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

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.

What is changing is speed.

For the first time, we can reliably produce three to four big books per year

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.

n 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.

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.

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.

Not to transform you for you.

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