How to build a Substack newsletter from scratch (and watch Pirate Eddie do it in real time)

This is a 🏴‍☠️ Founding Members–Only 🏴‍☠️ post. Founding subscribers get access to the Pirate Eddie Bot to ask category design questions, weekly actionable insights, and the entire library with 28+ audiobooks, 200+ mini-books, and more. See the Founders Deck here.

95% of people start a newsletter, send a few posts, and wonder why nothing happens.

They post. They wait. They hope.

And then crickets.

Newsletters don’t die because of writing. They die because they’re built like everyone else’s: random topics, no clear POV, no real flywheel.

We’ve spent years studying what makes newsletters break through the noise—and creating one that does. We wrote the playbooks on:

And now, instead of just telling you how to do it, we’re showing you.

Pirate Eddie and his wife Kristen are launching a brand-new Substack called Big Island Memory Making.

They’re starting at zero.

15 free subscribers.

0 paid subs.

Just an idea, a POV, and the same tools you have.

As a Founding Subscriber, you’ll get a front-row seat to the entire build-out:

• How to frame a POV → Why niche-down is the secret to scale-up.

• How to write for the top 1% → Non-obvious insights, not recycled takes.

• How to build an audience from scratch → No peanut-butter spreading. Just compounding content.

• How to use Substack + AI together → Your own “always-on” concierge that educates Superconsumers while you sleep.

• How to monetize early (and ethically) → Turning a newsletter into a profit center, not a cost center.

Because at the heart of every great newsletter is Intellectual Capital—your non-obvious insights, your POV, your way of seeing the world.

Most people let those ideas rot in Google Docs or Zoom calls.

You’ll see how to turn them into assets that scale.

This is the same way we built Category Pirates into one of the top Substacks in the world—only this time, you’re watching in real time.

And that’s what Founding Subscribers are going to see:

This isn’t just Pirates telling old war stories. Eddie & Kristen are practicing what we preach: niching down, building in public, and showing how to create a $0 CAC flywheel.

Their POV is sharp: multi-generational, multi-family milestone vacations are notoriously hard to pull off. The solution? One home that balances privacy and shared space, plus insider tips for navigating the Big Island. That’s the category they’re creating.

And they’re not doing it as a thought experiment. They have seven concrete goals:

• Equip their rental guests to design trips that maximize memory making

• Generate incremental leads for their property via digital content

• Use AI + intellectual capital to differentiate their rental

• Create revenue streams beyond rental income

• Build a family business with their adult kids

• Find a new adventure as empty nesters

• Prove out a $0 CAC marketing flywheel

All in all, it costs about $1,000/year to run (Substack is free, Delphi.ai powers the bot).

You don’t have to be in travel to learn from this. The principles are universal: niche down, clarify your POV, turn your Intellectual Capital into digital assets, and let AI scale your reach.

The point isn’t the niche. It’s the practice. Getting into the arena keeps our swords sharp and ensures we’re writing not just from the past, but from the future.

Publishing is easy. Scaling is hard. Most people confuse hitting “send” with making ideas spread.

What you’ll see in this build is how to take raw Intellectual Capital, frame it as a category POV, and scale it through Substack + AI so your ideas travel farther than you ever could on your own.

That’s exactly what Eddie & Kristen are doing.

Born and raised on Oahu, Eddie and his family have spent years making memories on the Big Island. Now they’re packaging those insights into a Substack and training an AI concierge on the content.

The lesson?

Whatever your category, Substack + AI is the best way to educate your Superconsumers on the problem you solve and your POV—while making money while you sleep.

The island is alive. It’s the youngest land in the world, still forming itself through fire and ocean. And it has a way of forming you, too—making you think bigger, freer, and weirder.

That’s why Eddie & Kristen are building Big Island Memory Making.

Not as a business experiment. But as an act of love. A way to share the place that’s given them so much.

And as a Founding Subscriber, you don’t just get to watch them build a Substack. You get to see what it looks like when Intellectual Capital is infused with passion—and why the best categories aren’t just smart. They’re personal.

How deep does our love run? Let us show you a few snapshots.

Every year, the Pirates gather on the Big Island to write, jam, and drink an unreasonable amount of Costco wine.

Chef Chris shows up with his legendary creations—like this whisky-smoked donut:

Out on the water, after wrapping the draft of Snow Leopard, we spotted whales breaching just offshore—a reminder that magic happens when you create in the right place.

(And yes, if you ever want to feel it for yourself, Founding members get $1000 off a stay at Eddie & Kristen’s Big Island home. Maybe one day we’ll host a full-blown Category Design Academy alumni gathering there. Who’s coming???)

If you are a Category Pirates Founding Subscriber as of September 30, 2025, you get:

• Full Big Island Substack library ($100 value)

• Access to the Big Island AI Concierge bot ($1,000 value)

• 10% off in home massages (4+) from Yasmine Mariano (~$60 value)

• 15% discount off of Chef Chris Galindo’s private meals (~$300 value)

• $1,000 off a week+ stay at their big island house if you book direct ($1,000 value). Just let us know your a Founding Subscriber.

That’s $2,500 of value added to your Founding membership. Free. For a limited time.

Category designing our Founding Subscriber tier has been one of the joys of 2025. This is where our Superconsumers live, and we’ll never stop adding more Scooby Snacks:

• Full Substack library ($200 value)

• Quarterly workshops ($100 value)

• AI templates and toolkits ($100 value)

• Free PDFs of our big books (~$150 value)

• Audiobook library & 3-packs ($2,000 value)

• Free access to special “textbook” content like our 115 FAQ ($149 value)

• Pirate Eddie AI Bot trained on 200+ books you can chat, text, or call ($1,000 value)

That alone adds up to $3,700 in value—or more than 10x your $350/year.

And now with Big Island Memory Making, the Category Pirates Founding Tier is worth $6,000 in total.

Put it all together and the Founding Tier isn’t a pile of perks. It’s the only system built to take you from raw ideas → sharpened Intellectual Capital → scaled newsletters, books, bots, and businesses.

If you want your ideas to scale, this is where you belong.

Never forget that:

• Thinking about thinking is the most important kind of thinking

• Content about the content is more important than the content

• Everything we value we’ve been taught to value

If you don’t want access to it, let us know at hello@categorypirates.com and we’ll opt you out.

Arrrrrr,

Category Pirates 🏴‍☠️

Eddie Yoon

Christopher Lochhead

Katrina Kirsch

That’s one of the things we teach inside the Category Design Academy. Month one is all about sharpening your Point Of View—the non-obvious truth only you can teach—and turning it into a foundation strong enough to build a paid newsletter, a book, or a business.

And you won’t be doing it alone. You’ll jam with Libby, our Academy AI, who acts like a coach—pushing you past the generic, asking the hard questions, and forcing you to make your POV undeniable.

You’ll also be part of a crew of likeminded Pirates—founders, executives, and creators who are designing their own categories-of-one. You’ll learn from each other, challenge each other, and celebrate the breakthroughs together.

Applications for the Fall 2025 cohort are now open.

👉 Apply here to define your POV, build your category, and finally launch the paid newsletter that scales your ideas.