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Category Pirates Plunge Into AI: Behind The Scenes Sneak Peek

Today, we're releasing 5 mini-books as AI audiobooks.

Dear Friend, Subscriber, and Category Pirate,

Category Pirates are sailing into the sea of Generative AI technology.

We wanted to share a sneak peek into our AI goals, progress, and lessons learned, so we can sail together and help you avoid the choppy waters. 

Why Are We Doing This?

The goal is the same as always, to unleash 100,000 category designers to bring the future to today.  

While we're proud of the 30,000 subscribers on Substack, the launch of the Category Design Academy and Strategy Therapy course made us realize you (our pirate ship subscribers) are facing four hurdles:

  1. You don't learn the same way as everyone else.

  2. You have a ton of content to sort through and learn from.

  3. You'd like learning category design to be as easy as possible.

  4. You want us to coach/teach more, so we need more automation.

We're working on three things (using generative AI) to help lower these hurdles. 

  1. Creating audio mini-books using AI versions of Pirate Christopher and Eddie’s voices. 

  2. Building a pirate chatbot (a retrieval/recommendation LLM) trained on all our content. 

  3. Converting our own marketing funnel into a flywheel using automation and AI.

What’s Today’s Pirate Booty?

Today, we're releasing the following 5 mini-books as AI audiobooks:

Free subcribers can preview the mini-books, and paid subscribers have access to the full audiobooks. If you’re not one yet, consider hopping aboard the pirate ship!

Upgrade to paid

If you’d rather buy a specific audiobook or listen to the smooth narration of Jason DeFillippo, you can check out the audiobooks available on Amazon.

Ron Swanson Listening GIF

Audio Mini-Books? It’s about time! ARRR!

For the AI audiobooks, our goal is to help meet pirates at their preferred learning style. A bunch of pirates have asked for audio versions of the mini-books so they can listen while working out, driving, or enjoying their Dude Wipes

The challenge was the analog version took too much time to record on our own, and the audiobook creation took longer than the mini-book writing.

Said differently: The juice wasn’t worth the squeeze. 

So we needed a more real time and more automated solution. Enter, which allows us to create our own Pirate AI voices. 

But to be clear, the goal is always progress—not perfection. 

We expect there to be quirks and oddities in the audiobooks. They can have Tourette’s Syndrome with random yips. And intonation and inflection appear to change randomly when you re-render the text. Volume can go up and down unexpectedly. 

Though there haven’t been any unexpected swears yet, to Pirate Christopher’s dismay.

(Please let us know if you hear anything horribly inaudible in a comment so we can re-render and fix it.)

Hear Al Pacino GIF

The Process & Lessons Learned

The AI audiobooks aren’t perfect. is great. It sounds pretty close to Pirate Eddie and Pirate Christopher’s voice. It does save time versus recording it the analog way. 

Here’s the AI audiobook process we are perfecting: 

  1. Edit the mini-book text to make it friendly for

    1. Prose vs. Piratey writing style

    2. Punctuation and spacing matter

    3. Be prepared to spell words out phonetically (e.g., proper nouns)

  1. Render the text.

  1. Listen and quality control the text.

    1. Listen carefully for weird quirks and make note of them 

    2. Change the text to fix the quirks

    3. Or sometimes, just re-render it

  1. Finalize and launch the AI audio mini-book. 

What’s next in the Category Pirates Generative AI Journey?

We'll keep building out the audio mini-books, but we’ll also share what’s going on with our AI Chat Bot/LLM and our marketing flywheel automation. 

But as we build, we’re also writing our mini-book on the Piratey Path to 10x Your Business via Generative AI Tools. Here, we'll jam on:

  1. Why you must embrace versus fear AI

  2. How to navigate AI projects

    1. Scope it tightly

    2. Be proactive vs. reactive

    3. Build top-down vs. bottoms-up

  3. AI vis-a-vis the Content Pyramid

If you’d like a sneak peek, watch the above video. 

We share this with you for two reasons.

As good marketers we want to tease cool new tech we’re building for you. But, more importantly, we hope to inspire you. Building a custom LLM/AI chatbot is critical for all businesses and creators. 

Yet few are doing it.

With every exponential new category of communication platform that spreads human knowledge (printing press, telephone, radio, TV, internet, cloud, social, mobile, AI) comes a radical breakthrough in new categories.

(New categories, create more new categories.)

Now is the time to put everything you know into your own custom content AI.

If a three Pirate micro-business can do it, you can too.

So get busy putting everything you know into an LLM.

Who knows what you’ll find—you might even category design a whole new market.


Category Pirates

Eddie Yoon

Christopher Lochhead

Katrina Kirsch

PS: Help like-minded pirates “think different.”

If reading this opened your mind to new and different thinking, share it with a friend or click the ❤️ button on this post so more people can learn about Category Pirates.