How to build a Substack newsletter from scratch (and watch Pirate Eddie do it in real time)
Our latest loot for Founding Subscribers: a front-row seat to building a Substack from zero.
This is a đ´ââ ď¸ Founding MembersâOnly đ´ââ ď¸ 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.
Dear Friend, Subscriber, and Category Pirate,
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 donât die because of writing. They die because theyâre built like everyone elseâs: random topics, no clear POV, no real flywheel.
Weâve spent years studying what makes newsletters break through the noiseâand creating one that does. We wrote the playbooks on:
How To Write A Top 1% Newsletter (differentiated POV, radical language, non-obvious insights)
How To Become a Top 444 Author (turning ideas into a publishing model that compounds)
And now, instead of just telling you how to do it, weâre showing you.
What if you could watch a top Substack get built from zero in real time and steal the playbook for yourself?
Pirate Eddie and his wife Kristen are launching a brand-new Substack called Big Island Memory Making.
Theyâre starting at zero.
15 free subscribers.
0 paid subs.
Just an idea, a POV, and the same tools you have.
As a Founding Subscriber, youâll get a front-row seat to the entire build-out:
How to frame a POV â Why niche-down is the secret to scale-up.
How to write for the top 1% â Non-obvious insights, not recycled takes.
How to build an audience from scratch â No peanut-butter spreading. Just compounding content.
How to use Substack + AI together â Your own âalways-onâ concierge that educates Superconsumers while you sleep.
How to monetize early (and ethically) â Turning a newsletter into a profit center, not a cost center.
Because at the heart of every great newsletter is Intellectual Capitalâyour non-obvious insights, your POV, your way of seeing the world.
Most people let those ideas rot in Google Docs or Zoom calls.
Youâll 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 worldâonly this time, youâre watching in real time.
Do you need another Substack to read? No. You need a Substack that shows youâstep by stepâhow to build a top-performing one.
And thatâs what Founding Subscribers are going to see:
1. Proof in the arena
This isnât 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. Thatâs the category theyâre creating.
And theyâre 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 donât 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 isnât the niche. Itâs the practice. Getting into the arena keeps our swords sharp and ensures weâre writing not just from the past, but from the future.
2. A blueprint to build your own Substack + AI bot
Publishing is easy. Scaling is hard. Most people confuse hitting âsendâ with making ideas spread.
What youâll 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.
Thatâs 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 theyâre 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 POVâwhile making money while you sleep.
3. Why weâre in love with The Big Island (and why you might fall too)
The island is alive. Itâs the youngest land in the world, still forming itself through fire and ocean. And it has a way of forming you, tooâmaking you think bigger, freer, and weirder.
Thatâs 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 thatâs given them so much.
And as a Founding Subscriber, you donât just get to watch them build a Substack. You get to see what it looks like when Intellectual Capital is infused with passionâand why the best categories arenât just smart. Theyâre 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 creationsâlike this whisky-smoked donut:
Out on the water, after wrapping the draft of Snow Leopard, we spotted whales breaching just offshoreâa 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 & Kristenâs Big Island home. Maybe one day weâll host a full-blown Category Design Academy alumni gathering there. Whoâs coming???)
Founding Subscribers get complimentary access to Big Island Memory Making at the Founding Tier through September 30, 2025.
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 Galindoâs 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.
Thatâs $2,500 of value added to your Founding membership. Free. For a limited time.
Still on the fence?
Category designing our Founding Subscriber tier has been one of the joys of 2025. This is where our Superconsumers live, and weâll 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 âtextbookâ 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 valueâor 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 isnât a pile of perks. Itâs the only system built to take you from raw ideas â sharpened Intellectual Capital â 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 weâve been taught to value
If you donât want access to it, let us know at hello@categorypirates.com and weâll opt you out.
Arrrrrr,
Category Pirates đ´ââ ď¸
P.S. â Want to start a paid newsletter but not sure how to define your POV or build it into a category of one?
Thatâs one of the things we teach inside the Category Design Academy. Month one is all about sharpening your Point Of Viewâthe non-obvious truth only you can teachâand turning it into a foundation strong enough to build a paid newsletter, a book, or a business.
And you wonât be doing it alone. Youâll jam with Libby, our Academy AI, who acts like a coachâpushing you past the generic, asking the hard questions, and forcing you to make your POV undeniable.
Youâll also be part of a crew of likeminded Piratesâfounders, executives, and creators who are designing their own categories-of-one. Youâll learn from each other, challenge each other, and celebrate the breakthroughs together.
Applications for the Fall 2025 cohort are now open.