Grow: How Category Pirates invented a new form of publishing

The Grow interview series is designed to share the nuts and bolts of how writers have gone independent and grown their audiences on Substack. It has been lightly edited for length and clarity.

We invited Eddie Yoon, Nicolas Cole, and Christopher Lochhead, who write Category Pirates, to share insights on how they created value for readers and a circular way for them to support Category Pirates’ work.

Eddie, Cole, and Christopher.

 

What’s your Substack about in one sentence?

Non-obvious ideas for people who want to create exponential breakthroughs in business and in life.

Who reads your Substack? 

People who want to think differently and create new market categories instead of competing in old market categories: founders, executives, investors, marketers, creators, writers, and students. 

Our readers range from CEOs of the largest global companies to the sexiest startups and growing number of solopreneurs. 

What do you uniquely offer readers? 

Most business content is authored by one individual. Category Pirates is, to the best of our knowledge, the only business-writing band: three individual thinkers who have come together to consistently co-create. Our readers don’t just experience one singular point of view of the world. They are exposed to ideas that can only be created at the magical intersection of different points of view.

Growth by the numbers

• Started Substack: January 2021

• Launched paid subscriptions: February 2021

• All subscribers: 17,000

• Paid subscribers: #4 paid Substack in Business

Meaningful growth moments

All subscribers growth chart

1. Getting started. The three of us originally set out to write a book on the subject of category design, a business growth discipline that focuses on radical differentiation to create exponential new demand. After about a year of working together, we realized we had a larger opportunity to write more than one book together. We made a commitment to co-creating as a group and started our Substack.  

2. First big milestone. We started publishing longform newsletters. Conventional wisdom is, short newsletters “perform better.” But the more we published, we realized our readers really enjoyed our in-depth explanations. So we published an 8,000-word letter and started calling our newsletters mini-books, to signal to readers that these weren’t intended to be newsletters you just skim. 

3. Published a book for free. We had been publishing on Substack for about a year, and in that time had written enough mini-books to string together into a cohesive book—The Category Design Toolkit. We decided to do the opposite of what most authors and publishers do: we gave the PDF of the book away for free the day it came out. We did a launch on Twitter and offered anyone interested in the book to download it for free in exchange for their email address. We captured 2,500+ emails in about 12 hours. Some napkin math told us that getting people to buy a $20 book is way less advantageous than getting a small percentage of those free readers to subscribe to our newsletter for $200/year. We essentially used the book as a lead-gen magnet for our Substack.

4. Published book number two. Six months later, we did the same thing for our next book, Snow Leopard. This time, we captured even more free emails, converted even more free subscribers to paid, and sold more print and e-books (at a higher price point) than before. This confirmed our approach that we could use our paid newsletter to essentially “get paid to write” books—our subscribers giving us our “advance” instead of a publisher, and keeping 100% ownership of the end product.

5. Today. We now have one of the most unique and powerful publishing flywheels in the world—and as far as we know, very few writers or publishers even know you can do what we’re doing. We hope to keep evangelizing our approach to writing and publishing digital assets.

Why did you decide to go paid?

The radically candid answer is: because people don’t value free things. Going paid forces people to feel invested in what they’re reading—which is a forcing function for learning. 

Relative to the outcomes, our newsletter is the cheapest investment you could possibly make in yourself. So being paid is 100% a “gesture” that forces readers to decide whether or not they are committed to reading, learning, and taking action based on the frameworks and new ways of thinking we share.

What’s your content strategy?

We publish “mini-books”—newsletters of roughly 8,000 words—every one to two weeks, with short curation newsletters in between directing readers to other mini-books in our archive, prompting them to upgrade. 

Category Science 101, a recent mini-book by Category Pirates

We combine thinking, storytelling, and data, written like a suspense novel. It is what makes our content so different in the business world. 

Most newsletters, authors, or “thought leaders” only do one of these three things well. But we strive for all three—and since there are three of us co-authoring the mini-books, our combined skill sets allow us to do this easily, efficiently, and consistently. 

We spend 20 to 30 hours per week writing the mini-books and want readers to understand that these are assets worth pouring a cup of coffee (or rum), closing the door, and sitting with in deep thought. Every six months or so, we then stack a handful of relevant mini-books together and publish a cohesive print book, monetizing them again. 

How did the three of you meet, and how do you work together? 

Christopher was working on his first book, Play Bigger, and ended up reaching out to Eddie regarding some research. Christopher had previously been a client of Cole’s. The three of us shared a lot in common and originally set out to write a book together. But after about a year of working together, it became clear we loved collaborating and the three of us were capable of producing much more than “just a book.” So we scrapped that first book and instead started a Substack. 

We’ve become great friends and thoroughly enjoy the co-creative process. Every Friday, we hop on Zoom together for about two hours and jam on a topic. Cole takes notes, essentially transcribing the conversation in real time, and then follows up with a first draft a few days later based on an idea and direction we all agree has potential. 

From there, Christopher and Eddie hop into the draft and add writing of their own—sometimes entire sections, other times comments and suggestions on things we can expand on. Cole then incorporates these new ideas and edits into a second draft, and then we all do a final read-through. 

What’s the sharpest insight you can offer other writers about growing a Substack publication?

Great writing isn’t about “writing.” It’s about thinking. 

You could be the most talented writer on Planet Earth, but if what you are writing is regurgitated “thinking,” then you aren’t a great writer. You’re a replaceable writer (because that “thinking” exists in hundreds of other places). 

If you want to grow your Substack, don’t think about how to become a better “writer.” Think about how to “think” differently, and then communicate that different thinking to the people who will value that different thinking the most.

What advice have you received about growing your publication that didn’t prove helpful? 

People said: “Nobody reads newsletters. Newsletters are saturated. People don’t like to read anymore. Your newsletter needs to be short. It needs to be like a TikTok video. You need to use memes.” Blah, blah, blah. 

The masses have been saying this for a decade (newsletters “died” back in 2009, they said). None of it is true. 

The reality is, people don’t have short attention spans—they have short consideration spans. If you are writing and publishing valuable, different thinking, and if that thinking helps your target readers unlock meaningful outcomes and breakthroughs in their lives, then it doesn’t matter if your content is 100 words or 1,000 or 10,000 or 100,000 words, readers will read all of it. Word count is, and has always been, a terrible measure of value.

Takeaways

• Make your best work free. Great writing is the best marketing. Category Pirates give away their books for a limited time to drum up excitement and harvest new sign-ups to their Substack. From there, they can enter into a relationship with readers through subscriptions. 

• Share your process. Instead of writing and publishing a book all at once, Category Pirates shares their work as they go. This allows them to be supported by readers on an ongoing basis and get feedback on their writing before it’s released in book form. 

• Band together. Three minds coming together on a subject can create more innovation than one. In a saturated market, Category Pirates were spurred on by their first forays into collaboration.

 

What questions do you have for Eddie, Christopher, and Cole that we didn’t ask? Leave them in the comments!

To read more from this series on growing your publication, see our interviews with BowTiedBull, Justin Gage, Noah Smith, Carissa Potter, Jørgen Veisdal, Anne Byrn, Nishant Jain, Michael Fritzell, Glenn Loury, Erik Hoel, Jessica DeFino, Mike Sowden, Elizabeth Held, Jonathan Nunn, Polina Pompliano, Michael Williams, Judd Legum, and Caroline Chambers.