3 questions you need to answer before 2026 starts
What we’re building in 2026 and what it means for you.
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Dear Friend, Subscriber, and Category Pirate,
Everyone is publishing the same year-end post right now.
LinkedIn is a wall of identical reflections—trend lists, lessons learned, tidy summaries that differ in wording but not in substance. They look thoughtful, responsible, and complete. They also quietly guarantee that next year will look an awful lot like this one.
Most people call this reflection.
We think that’s only half the job.
What matters is orientation.
Reflection asks, “What did I do?” Orientation asks, “Where am I standing—and is this position strong enough to break me out of the pack?” One creates a sense of closure; the other determines whether anything actually changes.
This is where breakthrough years are actually decided.
Not in trend predictions. Not in resolutions. But in whether you’re willing to reject the premise everyone else is accepting—and choose a different vantage point before the year even begins.
Everyone has goals for the new year.
Very few people ask the right questions.
If you want 2026 to be a breakthrough year, the three questions that matter most are below.
If you’re reading this and wondering whether you’re in the right room for a breakthrough year—this is the room we’ve been building for a long time.
Category Pirates didn’t start as a newsletter.
It started as a place for people doing smart work that wasn’t adding up—founders who weren’t confused about how to work harder, but about where to aim. People who sensed the problem wasn’t effort, but orientation.
The biggest breakthroughs don’t come from new tactics.
They come from a shift in vantage point—naming the real problem, rejecting the premise, and choosing a different position before the market forces one on you. Once that snaps into place, momentum follows naturally.
That’s why this has always been a thinking-first room.
We don’t chase trends here.
We don’t optimize for noise.
We slow things down just enough to help founders see what others miss—so they can move faster in the direction when it actually counts.
In 2025, we saw that orientation compound in a very real way.
One of the most meaningful experiments we ran this year was the Pirate Eddie Bot. What started as a way to help founders pressure-test their thinking quickly turned into one of the most effective things we’ve ever built—not because it gave answers, but because it asked better questions.
At the same time, we quietly launched the Founders side of the newsletter.
What happened surprised even us.
The conversations inside the Founders Deck were sharper. The outcomes coming out of Pirate Eddie Bot were clearer. And over and over, we saw the same pattern: when founders had a place to orient—and a thinking partner to jam with—momentum followed.
So as we look ahead to 2026, the move isn’t to invent something new.
It’s to double down on what worked.
Which is what brings us to the next experiment.
We’re actively building a Pirate Christopher Bot.
Not as a “tool.”
As a thinking partner trained on how Pirate Christopher actually helps pirates orient when the stakes are real.
No polite feedback. No surface-level suggestions. And yes—R-rated conversations.
As we build this next layer, we want your perspective in the room.
What would actually move the needle for you in 2026?
What do you want more of from us—and less of?
What kind of help from us would make the biggest difference right now?
Tell us in the comments what you want to see from us Pirates next.
If orientation is how you win the year, Creator Capitalists win the decade.
If there’s one thing we know for sure heading into 2026, it’s this: 2026 is the year of the Creator Capitalist.
Not creators chasing algorithms. Not founders grinding harder. But people who turn judgment, POV, and craft into assets that compound.
More people are realizing the real leverage isn’t attention—it’s ownership.
Not doing more work, but doing work that keeps paying you back.
If orientation decides whether a year breaks through, Creator Capitalism decides whether the work you do actually compounds.
It’s the difference between having a good year and building something that keeps working long after the year is over. The book is coming in March. The course relaunches in March too. (If you don’t want to wait, you can get started now.)
This is about choosing to be on the right side of a structural change.
If orientation helps you claim 2026, Creator Capitalism helps you claim the decade that follows.
Here’s what this all means for you:
We’re heading into 2026 with clarity about where we’re investing our time, energy, and best thinking.
Here’s how that shows up depending on how you’re sailing with us:
If you’re a free subscriber:
You’ll still get occasional free posts and previews to your inbox—and chances to jump into Pirate Eddie Bot promos and experiments when we open them up.
If you’re a monthly subscriber:
You’ll keep getting our Friday drops, including podcasts, mini-books, and the core Category Pirates thinking you’ve come to expect.
If you’re a Founding subscriber:
This is where we’re going all-in.
You get:
Full access to the Pirate Eddie Bot
Early access to the Pirate Christopher Bot as it comes online
All five of our big books
Wednesday Founder-only posts that break things down in a tactical, practical way
And more!
This is the inner circle—the room where we test ideas, pressure-test thinking, and turn POV into real outcomes.
If you’re an annual subscriber:
First, thank you.
If you’re on an annual plan, you’ve been some of our earliest and most loyal supporters. You backed Category Pirates before there was a Founders Deck, before Pirate Eddie Bot, before we fully understood what this community could become. That matters to us more than we’ve probably said out loud.
That clarity we’ve gained from the Pirate Eddie Bot is shaping our plans for 2026.
Looking ahead, we expect to move away from the annual plan and focus our energy on a single, all-access experience: the Founders Deck—where the work is more hands-on, more practical, and more connected to real outcomes.
If you’re reading this and thinking, “Wait… I supported you early—what does this mean for me?” that’s a fair question.
We don’t have all the details locked yet, but we do want you to know this: we care deeply about doing right by our annual subscribers, and we’re actively exploring thoughtful ways to welcome you into the Founders experience in a way that feels generous and intentional.
We’ll share more soon—before any changes take effect—and we’ll make sure there are no surprises.
For now, just know this: your support helped make everything that exists today possible. We’re genuinely grateful you’re here—and we can’t wait to help you unlock exponential outcomes in 2026 and beyond.
Three questions to category design your future in 2026
If you want 2026 to be a true breakout year—not just busier, louder, or more exhausting—these are the three questions that matter most.
(They’re the same questions we’ve been wrestling with behind the scenes as we plan our own 2026.)
Ponder them. Reflect on them as the year turns. Or jam on them with the Pirate Eddie Bot and see what your thinking reveals.