Category Pirates

Category Pirates

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

Authors! The status quo has got to go.

Category Pirates šŸ“ā€ā˜ ļø's avatar
Category Pirates šŸ“ā€ā˜ ļø
Nov 28, 2025
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Arrrrr! šŸ“ā€ā˜ ļø Welcome to a šŸ”’ subscriber-only edition šŸ”’ 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.


Dear Friend, Subscriber, and Category Pirate,

This mini-book is another love letter to our fellow authors and aspiring authors.

WAKE UP!

There are robbers in your house!

They are stealing your money and life’s work!

But there are two bits of good news. The first is that your neighbors at Category Pirates got a good look at all five in the gang. Their names are:

  1. HarperCollins

  2. Simon & Schuster

  3. Macmillan Publishers

  4. Hachette Book Group

  5. Penguin Random House

The second bit of good news is they didn’t take all your money.

They left you about 5-10%.

Below is a chart that Lucy (our Pirate-trained ChatGPT Pro) helped us build. It shows the percent of revenue that creators take home from major publishing platforms. We put the platforms we Pirates approve of in hot pink.

Shopify, X, Patreon, Substack, and OnlyFans share 80% or more of revenue with creators.

Bravo!

The original social media crew (YouTube, Meta, etc.) gives between 50% to 80% of revenue, which is still pretty good.

And Amazon’s self-publishing is way better than traditional publishing. But Amazon’s incentive structure is to give you a higher royalty if you price your books lower. Boo to Amazon. They are not as bad as the publishing gang of five, but Amazon is more like the local mafia dude who offers to protect you from the gangsters in exchange for protection money.

We reserve a special place for Audible (or Audacity, as we like to call them).

It’s a digital-first platform with awesome marginal costs and unit economics, just like their digital brothers and sisters. But they’ve chosen to steal money just like the OG traditional publisher crew by taking 60% to 75% of creator revenue for themselves!

Authors! Creators! The Status Quo Has Got To Go!

The Status Quo Has Got To Go!

The Status Quo Has Got To Go!

Category Pirates are designing a new book category that is worth $100 at the low end. One where Authors take at least 50% of revenue. One that could exponentially increase the total pie for everyone.

We’re calling this new book category Transformational Books (versus Reading Books).

More on this to come.

The good news is, we’re not alone.

Folks like Paul Millerd, author of The Pathless Path, are blazing the trail with us.

Why The Pathless Path Is Worth $100-$500 Per Book

When Paul clicked into a Zoom call with Penguin Random House, he was ready to jam on ideas for his book.

Instead, he sat through a rushed, overly confident pitch from a team that behaved as if the future of his book had already been decided. After brief introductions, the senior publisher and lead editor outlined their plan. They wanted to ā€œtake The Pathless Path to more people.ā€

The first step would be to take his book out of print, redesign the cover, and update the content.

Paul couldn’t hide his confusion.

Readers were buying the book in real time. He was selling thousands of copies a month.

The cover had become recognizable in his community. People were sending him messages about how much the book meant to them.

Nothing about the publisher’s proposal made sense.

He tried to understand the strategy.

  • They said they had better distribution.

  • That he would struggle as a self-published author.

  • They could get his book into markets he couldn’t reach alone.

  • They could send preview copies to big-name authors they knew well.

(Did you spot the ā€œBetter Trapā€ comparison? 🤮)

Paul joked that ā€œnothing was stopping them from sharing the book now if they believed in it that much.ā€ The joke didn’t land. The temperature of the call changed the moment he showed a hint of skepticism.

Still, he pressed.

He asked what ideas they had related to the book’s themes.

What he heard back was a set of generic marketing tactics that could have applied to almost any book on their list. There was nothing about unconventional careers, nothing about life design, nothing about the inner journey that had made The Pathless Path resonate with thousands of readers.

Finally, they delivered the offer:

$70,000 in exchange for lifetime rights, plus 70 years after his death.

Paul did the math in real time. In the month before the call, he had made about $10,000 in royalties from 2,000 copies sold. Sales were climbing. Readers were sharing it with their friends and colleagues.

The book had momentum.

The numbers didn’t add up (not even close).

Before the call ended, the publisher pushed him to say what would interest him. He hadn’t prepared a counteroffer because he didn’t expect the conversation to get that far. But something in him refused to play the role they expected him to play.

He took a breath and said, ā€œMuch higher.ā€

They asked him to name a number.

He surprised even himself when he said, ā€œ$600,000.ā€

That is not an answer from a writer. That is an answer from a writer who spent time at McKinsey and BCG. That is an answer from someone who sees a path from $300K in lifetime earnings to $1MM plus, but who understands expected value and the time value of money.

The air in the room drained.

The publisher didn’t know what to do with an author who believed his book was worth something. They told him he needed to talk to an agent. The call ended in awkwardness.

Paul closed his laptop and declared, ā€œI’m definitely not doing the deal.ā€

But instead of panic, he felt clarity. Instead of doubt, he felt conviction. Instead of worrying he had just made a reckless decision, he felt the unmistakable sense that he had narrowly escaped something that would have taken the soul out of his work.

Over the next few days, he kept returning to the same realization:

The traditional publishing model wasn’t built for creators.

It would never care about his book the way he cared.

It couldn’t sustain the level of attention, craft, and intention he wanted to pour into the work. It couldn’t match the momentum already coming from readers. And it couldn’t justify taking ownership of the thing he cared about most.

Paul realized his book was a hit, and he hadn’t even begun to explore how far he could take it.

So, he made a decision.

He would create the book he wished existed. He would choose craft over compliance, agency over approval, and creativity over compromise. He would make something beautiful and worthy of the ideas he cared about.

The result was a $95 Italian-printed, slipcased, art-forward collector’s edition of The Pathless Path that sold 250 copies in two weeks and shipped to 22 countries.

He invested real money and trusted his creative instincts. He built something no publisher would have ever approved. And he discovered he had Superconsumers who didn’t want a cheaper book, but a more meaningful one.

So when Paul saw we launched Lightning Strike Marketing for $100, he didn’t assume we’d lost our minds.

He saw someone else rejecting the same premise he had rejected.

On a call with Pirate Eddie, he started chanting: ā€œOne of us. One of us. One of us.ā€

Publishing is an outdated system that extracts upside from those who create it. When you zoom out, you start to see the pattern. Authors are playing a game they didn’t design, with rules that were never written in their favor.

That’s what this mini-book is here to expose:

  • Why publishing economics are fundamentally misaligned, and how you can redesign them in your favor

  • How the default publishing model puts authors in the ā€œBe the Winnerā€ and ā€œBe the Bestā€ traps

  • How to join the new publishing category that’s emerging for authors who choose to ā€œBe Differentā€ and want to own their economics, craft, and future

But first, we need to name the problem.

(If you haven’t read The $100 Book mini-book, we recommend starting there.)

Publishing Defaults Are Rigged Against Authors

Every author enters the publishing world believing they’re choosing between ā€œself-publishingā€ and ā€œtraditional publishing.ā€

They’re not.

What they’re actually choosing between is:

  • A legacy system optimized for publishers, not creators

  • A worldview that treats books as commodities instead of creative assets

  • A pricing psychology built for a 1960s supply chain instead of a 2020s digital economy

Most authors don’t realize this because the industry wraps its incentives in a warm blanket of prestige, credibility, and ā€œwe know best.ā€ But once you look a little closer, the publishing industry’s Category Design Scorecard strategy reveals itself in full.

The ā€œBe The Winnerā€ Publishing Game

This is the default for 95% of authors today.

But it’s the most psychologically seductive trap of all. You publish with a legacy publisher or on Amazon. You optimize for keywords, categories, metadata, and algorithms. You play the ranking game. You chase volume. You measure success by charts, badges, and the dopamine hit of ā€œ#1 Bestsellerā€ (a label given out more freely than Costco samples).

You discount.

You discount again.

You discount on Black Friday.

You end up in the $0.99 bargain bin. You get there even faster thanks to Audible’s $0.99 promotion that you can’t control!

The only winner in ā€œBe The Winnerā€ is the publisher.

This is the trap Paul could have fallen into on the call with Penguin Random House. The publisher promises credibility, distribution, and a way to make your book ā€œbig.ā€

Prestige has a price, and publishers know most authors will pay it.

  • The price is control.

  • The price is ownership.

  • The price is your creative autonomy.

The publisher captures the economics, controls the distribution, and decides what readers see. The publisher, not you, becomes the customer’s point of loyalty. You become indistinguishable from every other author shouting into the same digital aisle.

Worst of all: You are competing in a race to the bottom, where the bottom has no floor.

The ā€œBe The Bestā€ Publishing Game

Be The Best is where talented and thoughtful authors and creators (unintentionally) end up.

You work meticulously on your book until the copy shines. You fuss over sentences, structure, rhythm, and aesthetics. You make the book beautiful because the book matters. You do exceptional work, but get ordinary economics.

Most importantly, you get to raise your prices. Which is incredibly important as a first step.

But you can’t stop there.

The ā€œartistā€ lane, without a well-designed business model, can destroy your economics.

Why?

Because in Joe Pine’s progression of economic value, even a super-ding-dong premium-priced book is still a good. You must elevate to a service, experience, or transformation. Just like Pirate Paul Millerd has done with this $200 ā€œbuy one and get oneā€ gifting option and his $500 bundle with more Scooby snacks and a coaching call.

Play Bigger fell into the ā€œBe The Bestā€ publishing trap.

The ideas and concepts in the book Play Bigger are radically different.

But the business model was woefully conventional.

By every external measure, Play Bigger was a win. It became a global bestseller. It sold hundreds of thousands of copies. It shaped the language of the category design discipline. It created a movement.

It’s still one of the most cited business books of the last decade.

Even with that level of impact, the author economics are… ordinary.

Play Bigger created extraordinary value for readers, executives, founders, investors, and teams. But HarperCollins owns the rights, controls the pricing, and captures the majority of the margin. They also dictate the terms (from royalty structure to format to distribution) because that’s how the ā€œBe The Bestā€ publishing strategy is designed for authors.

  • Do exceptional work.

  • Elevate the category.

  • Win external recognition.

  • Make an exponential difference.

  • And still receive the smallest percentage of the value created.

Play Bigger was such a success, it exposed the limitations of the traditional model with painful clarity. Pirate Christopher estimates the book has made multiple millions of dollars, while all four authors made in the low six-figures—not each, collectively.

(Note: Pirate Christopher and his co-authors have made many millions by leveraging Play Bigger for consulting and advising services, speaking events, and net-new Intellectual Capital HarperCollins can never replicate.)

The Play Bigger experience is similar to the one talented authors have every year. You create something world-class, but you don’t control the economics that world-class work generates.

The system routes the upside somewhere else.

What’s Really Going On Here?

At the structural level, the publishing ecosystem is designed around three assumptions:

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