Arrrrr! 🏴‍☠️ Welcome to a Free Post of Category Pirates. Each week, we share radically different ideas to help you design new and different categories. Founding subscribers can access the entire archive of 200+ mini-books, The Pirate Eddie Bot and Pirate Christopher bot, copies of our 7 Big Books, and 30+ audiobooks. If you’re not a founding subscriber, hop aboard!

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Dear Friend, Subscriber, and Category Pirate,

Here’s a fun thought experiment.

Open your favorite AI tool right now and ask it to do your job. Write the email. Build the deck. Summarize the report. Draft the proposal. It’ll do a pretty good version of all of it. In some cases, a better one than you would have produced on a Tuesday afternoon when you were tired.

Now ask it to build you 200 people who trust you, buy from you, refer you, and show up for you when it counts.

It can’t. It never will.

We had this conversation in the Academy last week. Pirate Christopher explained how a thought leader actually builds trust, and the answer was simple enough to fit on a sticky note: Be a trustworthy person. Say what you mean. Do what you say. And then Pirate Christopher dropped this bar:

“Who you are speaks so loudly, I can’t hear what you’re saying.”

That’s the part AI cannot touch.

A model can mimic your tone. It can copy your formatting. It cannot show up for someone on a Tuesday for three years running. It cannot keep a promise. It cannot, as Gina Bianchini puts it, create people magic: the thing that happens when humans gather around a shared point of view and discover they were never alone in their thinking.

People magic is the asset AI can’t steal. Community is where you store it. Category design is how you build the gravity that pulls people into it in the first place.

And the Four Capitals from Creator Capitalist are what compound inside it.

• Intellectual capital gives you something worth gathering around.

• Reputation capital is what gets built when you keep showing up the way Pirate Christopher described.

• Relationship capital is the deep, durable trust that turns an audience into a community.

• Financial capital is what all four make possible, the freedom to fund experiences your knowledge worker self has never let you dream about.

AI can speed up the first one. It cannot manufacture the other three.

Which is exactly what we’re getting into next Wednesday with one of our favorite Creator Capitalists on the planet: Gina Bianchini, CEO of Mighty Networks, the platform whose Hosts generated over $500M in 2025.

Pirate Gina, Pirate Eddie, and Pirate Christopher are running a free live event called “The Asset AI Can’t Steal” on Wednesday, May 27 at 11 AM PT.

We’ll get into:

• Why community is the one piece of your business AI cannot compete with

• How to find your superpower and build a category around it

• How the Four Capitals from Creator Capitalist compound when you’ve got a real community attached to your work

👉 Grab your free seat here.

Arrrrrrr,

Category Pirates

Eddie Yoon

Christopher Lochhead

Subscribe now

Dear Friend, Subscriber, and Category Pirate,

“Bet on yourself sooner” is the most popular piece of career advice on the internet.

But no one tells you how.

Good news. Linda’s story lays the practical and tactical out clearly.

Most people hear it and do the obvious thing.

They bet harder on the most visible capital they already have. They chase a bigger title (Reputation Capital). A bigger paycheck (Financial Capital).

Then they wonder why nothing compounds.

Linda Deeken did the opposite for twenty years.

And it’s the reason she can run her own thing now with more leverage than most of the partners who once outranked her. Five kids. Two sets of twins. A daughter with Down syndrome who also beat cancer. A husband with his own career. A solo consulting practice (Deeken Strategies) with agency and economics most W2 partners long for. A returning client roster that calls her because she “makes them better.”

She built all of that by quietly betting on the two non-obvious capitals first.

Relationship Capital and Intellectual Capital come first.

Relationship capital and intellectual capital compound silently.

Linda spent twenty years building these two capitals first. By the time she launched Deeken Strategies, the math was lopsided in her favor. The reputation and the financial returns came roaring in because the other two had been compounding the whole time.

Four moves that looked like sidesteps and were actually compounding.

Linda turned down Stanford for UW Madison at 17. Her father was older, her mother had her at 43, and Madison just made more sense for her family. She traded the diploma everyone in her future networking room would have recognized for time with people who would not be around forever.

How many of us would make that choice?

1 out of 100? 1 out of 1,000? Maybe even less.

She left Mercer for The Cambridge Group. Mercer had the bigger brand. Cambridge was 50% female partners who were working moms, the better operating model, and the path that would actually let her become both a serious consultant and a mother. Reputation down. Relationship and intellectual capital up.

She went to Miller Brewing Company for a year, had her first set of twins, then came back to Cambridge as a CMO, not a partner. Title down. Writing muscle up. The CMO role forced her to develop her own point of view instead of executing other people’s frameworks. That’s the season most consultants never get. It’s also the season that built the intellectual capital she now monetizes on her own.

She launched Deeken Strategies before she had the permission slip she wanted. By her own admission, that was the bet she wishes she had made sooner. She could only make it because the first three bets had already loaded the dice.

Her superpower is the outcome other people get when they work with her.

The way Category Pirates defines a superpower is different from how most people do it. Most people would say a superpower is what you’re good at. We say a superpower is the outcome you produce for others that you are best known for.

Linda’s clients describe her in three words: smart, humble, focused on your outcomes.

That combination is rare on its own.

It’s rarer still in someone running a household of seven. And it’s the languaging she earned by writing, by refining her POV through the CMO season, and by treating every client engagement like a long-term relationship instead of a short-term transaction.

She runs her household the same way she runs her client work. She has a SWOT analysis for each of her five kids. Strengths, weaknesses, opportunities, threats. She is not parenting her kids to become the best version of her. She is consulting them into the best version of them.

This is what integration actually looks like. The work feeds the parenting, the parenting feeds the work, and both halves get sharper because the same operating system is running underneath both.

Here’s how to navigate this conversation:

• 05:17 – Turning down Stanford at 17: The first time Linda chose relationship capital over reputation capital, and why she never built her identity around the diploma she didn’t get.

• 12:23 – Chemical engineering as a consulting prep school: Why studying the hardest thing makes the easier things easier, and why “learning the lingo” is the first move in building intellectual capital.

• 18:55 – Leaving Mercer for Cambridge: Trading the bigger brand for the operating model that would actually let her become both a serious consultant and a mother.

• 25:12 – The Miller detour: One year in corporate, a set of twins, a move to Milwaukee, and what she learned about herself in a job she didn’t love.

• 26:35 – The CMO role she designed: How Linda built a returning role at Cambridge that gave her flexibility AND forced her to develop a POV instead of executing other people’s frameworks.

• 29:08 – “Put me in coach”: The moment the CMO role stopped being enough and Linda launched Deeken Strategies.

• 45:53 – Smart, humble, oriented to your outcomes: The three-part combination that became Linda’s superpower and the languaging her clients use to refer her.

• 49:38 – Children as consulting projects: The SWOT-per-kid framework, why she rejects the “I want my kid to do what I never did” trap, and what Sarah is teaching the whole family.

• 1:04:19 – Own your own future, fearlessly: Linda’s closing convict to every woman watching from the sidelines.

What Linda is doing is not a one-off.

It’s a pattern.

The same pattern Creator Capitalist documents end-to-end. Bet on relationship and intellectual capital first. Develop your point of view. Find the work that builds your four capitals at the same time. And then, when you can’t bear NOT to bet on yourself any longer, bet.

She did it intuitively, over twenty years, without the framework. Imagine what that compounding looks like when you have the framework AND the twenty years ahead of you instead of behind you.

Connect with Linda:

• Follow her on LinkedIn here

Arrrrrr,

Category Pirates 🏴‍☠️

Eddie Yoon

Christopher Lochhead

P.S. The fastest way to figure out which capital you’re under-betting on.

Linda did this work over twenty years, mostly alone, by writing in the margins and pressure-testing her own thinking against clients who became friends. You don’t have to.

Become a Founding Subscriber, and you’ll get access to The Pirate Eddie Bot and the new Pirate Christopher Bot. They will challenge your premise, sharpen your POV, and stop you from doing what most people do when they say they’re betting on themselves, which is just betting harder on the capital they already have plenty of.

→ Become a Founding Subscriber to get access here.

Subscribe now

Dear Friend, Subscriber, and Category Pirate,

We have an exciting update for you.

A year ago this week, we launched the Pirate Eddie Bot. At the time, it was a librarian. You’d ask it a question, it would point you back to a mini-book, you’d go do your own thinking.

A year later, it’s a thinking partner. Pirates jam with it at 2 AM and walk away with categories they had been sitting on for years. They use it to design Lightning Strikes that produce six-figure outcomes. They send real Eddie text messages that say things like “the Pirate Eddie Bot is effing awesome.” (More on that in a minute.)

We’ve shipped a lot this past year, and we’re shipping even more today.

Here’s what’s launching today for Founding members.

Pirate Eddie Bot 2.0 ships today. This is our first major version upgrade since the bot launched a year ago. Going forward, the Pirate Eddie Bot will ship on a release cadence, the same way Anthropic ships Sonnet and OpenAI ships GPT. A new version will be released every six months.

Version 2.0 is so much better than 1.0 that it surprises even us. Every month, Founding members produce outcomes with it that we didn’t think a bot could produce.

Pirate Christopher Bot 1.0. Live for the first time, exclusively inside Founding. He’s the hammer to Eddie’s velvet. Where Eddie gives the direct answer, Christopher tells a story and reframes the question. Founding subscribers can access the Pirate Christopher Bot with the same password used for the Pirate Eddie Bot.

Of course, the Pirate Christopher bot won’t say “effing.”

Together, the two bots do something neither does alone. Ask the Pirate Eddie Bot. Paste the answer into the Pirate Christopher Bot. Watch the Pirate Christopher Bot push back. Run that back through the Pirate Eddie Bot.

It’s the closest thing to being in an Academy workshop without being in the room.

And here's everything else we shipped this past year. Already inside the Founding subscription.

Three new books shipped this year. Lightning Strike Marketing, Thinker’s High, and Creator Capitalist (available to Founding Members today).

24 new audiobooks.

24 new mini-books + access to the library of 250+ mini-books.

48 Wednesday Founder posts.

With that said, three things are changing this week.

1. The annual plan as you know it is ending today. Going forward, the annual tier and Founding are the same thing. Same benefits, access, and bundle. You will still see an annual option when you go to subscribe (Substack doesn’t let us remove it), but it is now functionally identical to Founding.

2. Founding pricing is moving Sunday May 17th at midnight. These are the final few days to lock in $350 forever. If you upgrade by Sunday, you get grandfathered in at $350 for life, as long as you keep renewing. That includes everything we just shipped today, this year, and next year. Starting Sunday at midnight PST, Founding moves to $375. Permanently. You can expect to see a modest price increase for new subscribers every year.

3. Both bots are now exclusively inside Founding. The Pirate Eddie Bot 2.0 and the Pirate Christopher Bot 1.0 live inside the Founding tier. That is the only place to access them.

What this means for you.

If you’re already a Founding member at $350: You are locked in at $350 forever, as long as you keep renewing. Your Pirate Eddie Bot password is the same for the Pirate Christopher Bot. You can access both bots here.

If you’re on the $200 annual plan: Many of you have been with us for years. As a thank you for your loyalty, we want to be radically generous. Starting today, you get the full Founding bundle at your same $200 price. Forever, as long as you keep renewing. Both bots. Every audiobook. Every mini-book. Every founder’s deck. You’ll receive your unique password for the bots in your inbox today.

If you’ve been on the fence: Now’s the time. After Sunday, the only way in is $20 a month for the library, or $375 for the Founding bundle.

The price is moving from $350 to $375 because the bundle is materially bigger than it was last year. Last year, you got one bot. Now you get two. Last year, there were 4 books; now there are 7.

👉 Lock in $350 Founding before Sunday May 17th at midnight here →

The best thing we’ve ever built.

In two careers, dozens of best-selling books, and several top 1% podcasts, we have never built anything that produces outcomes at this ratio.

For about a dollar a day, you get an AI thinking partner trained on every framework we have ever published. The same questions we ask people who pay $10,000 to be inside the Category Design Academy. Plus a second bot to push back on the first one. Available at 2 AM. Never runs out of words. Gets smarter every six months at no additional cost.

We hear it from Founding members every week. They opened the bot for one thing and walked out with the language for something they had been chasing for years. They closed deals they thought were dead. They named a category they had been circling for a decade.

It is the most leverage we have ever put inside a subscription. And it is the highest-leverage thing the people inside the Founding tier are using right now.

Pirates love it.

Kyle Okimoto has built his career on being rational. Cambridge Group strategy consultant. Head of strategy for Merrill Lynch’s wealth management business. Head of marketing at E*Trade. He’s launching a new category right now that helps families in Hawaii consolidate ownership of inherited commercial real estate.

He has access to every AI on the planet. He picked the Pirate Eddie Bot.

When Eddie asked him why, here’s what he said:

“I’ve known you for decades. I know your family. I know we have the same value system. I know your intellectual capital. I trust the rigor of your IC. I trust the integrity of your IC.”

A man who built his career on rational decisions made an emotional one. Around trust.

That’s what you get when you join as a Founding member.

One more thing. A group offer for teams.

For the first time, we’re opening a 10+ seat Founding bundle at $300 per seat. If you’re a CMO, a founder, or a team leader who wants ten people trained in category design with full bot access, you can register your team here.

Sunday is the line.

A year ago this week, we shipped the Pirate Eddie Bot 1.0. Today, 2.0. Six months from now, 3.0. A year from now, 4.0.

We’ll keep shipping. The price will reflect the work.

But the OG $350 only lives until Sunday May 17th at midnight. After that, it’s $20 a month for the library or $375 for Founding.

Join the the Founding Tier before Sunday

If you’ve been on the fence for a while, this is the week.

Arrrrrrr,

Category Pirates 🏴‍☠️

Eddie Yoon

Christopher Lochhead

Arrrrr! 🏴‍☠️ Welcome to a 🔒 subscriber-only edition 🔒 of Category Pirates. Each week, we share radically different ideas to help you design new and different categories. For more: Audiobooks | Category design podcast | Books | Sign up for a Founding subscription to ask the Pirate Eddie Bot your category design questions.

Subscribe now

Dear Friend, Subscriber, and Category Pirate,

You might be wondering what right two dudes have to write about motherhood.

That’s a legit question.

Pirates Christopher and Eddie are Category Designers, which makes us time travelers from the future.

We already see the future of millions of Creator Capitalists who use their different, to make a massive difference for others and get paid to create at scale. Creator Capitalists no longer trade time for money anymore, but monetize their Four Capitals while they sleep.

This includes mothers.

Mothers to be. New mothers. Empty nest mothers. Grandmothers. Great-Grandmothers.

What happens if abundance from your career is no longer tied to time?

What if you get paid for the value you create?

Not the time you donate.

Would that change the equation for motherhood? Should you have kids? When should you have kids? How many kids should you have?

These are all personal questions. Life design questions.

We believe everyone should have the agency to make their own decisions.

We are saying more than one thing can be true.

(When you start noticing. You’ll discover that we’re presented with many false choices. Who says you can’t have it all? Who says you can’t live your definition of a legendary life?)

• Careers are incredible.

• Children are awesome.

• Work can be wonderful.

• Motherhood is majestic.

• Women should have agency.

• The woman can/do create new value.

• The declining birthrate is a societal concern.

• Few things are more important than when a child needs their mom.

• Children need to see their mother make massive dents in the universe.

Our goal is to write with courage.

We love our mothers. We love our wives. And the many legendary women in our lives.

And. We also did our homework.

We gave the Category Pirates platform to six legendary women on the Pirate Ship. Five in a roundtable, one in a deep-dive podcast. What follows is their wisdom and wishes, their stories and scars, mapped onto the Creator Capitalist framework.

These are women who have built businesses, raised children (including kids with Down syndrome, autism, and cancer), navigated divorce, managed elder care, traveled the world for consulting engagements, and walked their kids to elementary school, sometimes in the same week.

Most are Category Design Academy alumni. They are moms. And they are incredible Creator Capitalists.

This is the future we co-wrote all together.

A different lens on motherhood.

And (we think) it looks beautiful.

You be the judge of that.

Evolution of Modern Motherhood

In 1950, about one in three American women worked outside the home. By 1999, it was nearly three in five. Economists called it the most significant labor market shift of the 20th century.

That was Motherhood 2.0. The promise was that women could have careers AND families. The system would adjust. Everyone would benefit.

The system did not adjust.

Instead, it asked women to do two full-time jobs simultaneously, career and household, while paying them roughly 82 cents on the dollar for the first one and nothing for the second.

Zebra hole alert!

We’re going down an academic zebra hole! Follow us at your own peril. Just know that none of us are PhD academics, and while economics is a valuable field, it is still part of social science.

Pirates should have a swig of skepticism with social science.

“Any field that had the word ‘science’ in its name was guaranteed thereby not to be a science”, Frank Harary, a mathematician.

There’s a reason why Physics is called Physics and not Physics Science.

But hey ho, let’s go!

There are two types of wage gaps: uncontrolled and controlled.

Uncontrolled data is what it sounds like. It’s the raw data without adjustments. It is comprehensive, but it can be noisy.

Controlled data is where you calibrate the data to be apples to apples (e.g., same qualifications, same life circumstances, same job).

Imagine if Pirate Christopher and Eddie were both at a business meeting and wore recorders around their necks, and we counted the number of words said per day. It would show that Pirate Christopher is a lot more talkative than Pirate Eddie.

That is uncontrolled data.

Now let’s adjust the data from words per day to words per hour. What you’d find is Pirate Eddie basically stops talking around 4 pm, when he runs out of words. He’d sit at dinner, listen intently, smile and react, but say very little. The words per hour before 4 pm are probably the same. Words per hour after 4 pm is where the difference is.

That is controlled data.

Academics looked at controlled data regarding the wage gap for the same job with the same qualifications, and women earn 99 cents on the dollar.

It’s basically parity. The number you usually hear, 82 cents, is the “uncontrolled” gap. Both numbers are real. But they’re measuring completely different things. The 82-cent number doesn’t mean employers are paying women less for identical work. It means women end up in different work.

The research on why is led almost entirely by women.

Claudia Goldin at Harvard won the 2023 Nobel Prize in Economics for proving it. Ruth Thomas at Payscale runs the annual reports that track it. Heidi Hartmann at the Institute for Women’s Policy Research quantified it.

The data isn’t some dude’s opinion.

Motherhood is the simplest explanation for the 17-cent canyon between the controlled and uncontrolled numbers.

Statistically, the motherhood penalty accounts for nearly 80% of the entire remaining wage gap. Motherhood changes which jobs women take, how many hours they work, when they get promoted, and whether they stay in the workforce at all. Pay transparency tools like Glassdoor and state-level disclosure laws have helped close the controlled gap to near-parity.

Both data points prove Motherhood 2.0 is structurally broken.

It asks women to choose between compounding their career or raising their family, and then penalizes them for whichever one they pick. The controlled gap closing to 99 cents is proof that the “equal pay for equal work” fight is nearly won. The uncontrolled gap widening to 82 cents and getting worse in 2026 is proof that the real battle was never about paychecks.

The gap is in the design of work.

The gap is in the design of motherhood.

This is called life design.

Going forward, we will use the uncontrolled numbers.

Because the controlled data, for all its precision, hides the very thing we’re trying to see. Controlling for job title and experience is like measuring the speed of runners who made it to the finals and concluding that everyone runs about the same pace. Technically true. But it completely ignores the thousands who never made the starting line.

The uncontrolled gap captures the full picture: who’s in the workforce, who left, who downshifted, who never got promoted, who took seven years off, and couldn’t get back in. It captures the mothers.

That’s the gap Motherhood 3.0 is designed to close. Not the paycheck gap, which is nearly solved. The participation gap. The ambition gap. The compounding gap. The gap between what mothers could build and what the 2.0 system allowed them to build.

The earnings hit women take after having children accounts for nearly 80% of the entire gender pay gap. Working women see their incomes drop sharply, on average, after having kids. That gap never fully recovers.

Now, some strange things are happening all at once.

The U.S. fertility rate hit a record low of 1.6 births per woman in 2024, and dropped again in 2025, well below the 2.1 replacement rate. Talented women are looking at the math and saying: no thanks.

455,000 women left the workforce in early 2025 between January and August 2025, the steepest decline since the pandemic. Return-to-office mandates nearly doubled. It looks, on the surface, like Motherhood 1.0 is making a comeback.

But here’s the number nobody is talking about: women launched 49% of all new businesses in 2024. Up from 29% in 2019. A 69% increase in five years. The highest share ever recorded. 14.5 million women-owned businesses generating $3.3 trillion in annual revenue.

And yet, not all the business numbers are up and to the right. Pirate Lydia says, “I gave a talk at Extraordinary Women in Tech. My dream is that in five years, women will receive 50% of the investment. At the time, it was 9%. Today, it is less than 2%. So we are going very, very backwards.”

Women are not going back to 1.0. But 2.0 isn’t working.

They’re building something new.

Let’s call it Motherhood 3.0.

Motherhood 1.0 was the stay-at-home mom. One income, one career, mom stays home. The “good mom” is defined by presence.

Motherhood 2.0 was the working mom. Two incomes, managed compromise, the second shift. The “good mom” is defined by her ability to juggle everything and never drop a ball.

Motherhood 3.0 is the Creator Capitalist mom. She designs her own career. She builds four compounding capitals: Financial, Reputation, Relationship, and Intellectual. She deploys AI to eliminate the logistical tax that crushed the 2.0 generation. And she integrates motherhood and career instead of compromising between them.

She does this by prioritizing Relationship and Intellectual Capital ahead of Financial and Reputation Capital.

Motherhood Prioritizes Relationship Capital

Motherhood is the choice of elevating Relationship Capital as first among equals.

Getting pregnant is a choice to put the Relationship Capital with your unborn child ahead of your Reputation Capital (e.g., your career), your Financial Capital (earnings), and your Intellectual Capital (pregnancy brain fog is real).

Women are often asked to put relationship capital first all the time.

In high school, Linda Deeken got into Stanford.

Most teens would be doing cartwheels. But Pirate Linda was the youngest of five children. Her mom had her later in life, in her early 40s. Pirate Linda knew Stanford had a price tag with ramifications.

The University of Wisconsin at Madison was a financial no-brainer.

Her father told her, “The Lord will always walk with you. And so the opportunities that are in front of you, the gifts that you have been given. He will actually take it right with you to its fullest expression. And so that can happen at Wisconsin. It can happen at Stanford. Make the choice that is the best choice for you.”

Linda made the choice that was the most loving to her family.

She chose Wisconsin.

She chose Relationship Capital over Reputation Capital.

It wouldn’t be the last time she made that choice.

Just like many women.

Linda said, “Have I had moments in my life where I’ve looked back and said, I wonder what, I wonder if? Sure. But I have been blessed and things have worked out swimmingly. And frankly I think it made me a harder worker. It made me invest deeper in myself because I felt like my dreams were my dreams, and I needed to make them happen.”

The Enduring ROI Of Relationship Capital

Relationships that stand the test of time have an odd power that perseveres.

Pirate Eddie has friends from junior high that have incredible meaning in his life. They were there for him when Pirate Eddie was a noob and a nobody. They’ve known him at his lowest and his highest. And those feelings compound as they age.

The other three Capitals are different.

Financial Capital can be volatile.

If invested well, Financial Capital compounds over time. But market bubbles, Madoff fraudsters, and excessive leverage/debt have destroyed many fortunes. As the late, great Charlie Munger put it, “There are only three ways a smart person can go broke: liquor, ladies, and leverage.”

Reputation Capital has a half-life.

Sadly, you are only as good as the last thing you did, and you are only as valuable as what you can do for others.

Pirate Eddie once spoke at a conference, where he met Jim Donald, who was next up after him. Jim was a three-time CEO of Starbucks, Albertson’s, and Extended Stay Hotels. He’s had an amazing career, but he noted the odd experience of the last day of being a CEO and the next day. Everyone wants your time when you are CEO, but the day after, it’s like you become invisible and never existed.

That’s why they call it a hamster wheel.

Intellectual Capital has staying power until it is trumped by new Intellectual Capital.

Pirate Aristotle was the man, until Pirate Galileo contradicted him on inertia, gravity, and astronomy and was tried, convicted of heresy, and arrested for life.

Blockbuster laughed Netflix out of the room when Reed Hastings asked Blockbuster to buy them for $50 million dollars. The great Tim Cook didn’t return Elon’s call when Tesla was about to go bankrupt, and he was ready to ask Apple to acquire them. Pirate Eddie was dismissed on CNBC for saying Tesla Model 3 supers were weird, in that they weren’t luxury car owners switching, but they were Prius, Camry, and Corolla owners trading up.

You should, of course, invest in and grow all the four Capitals.

But women and mothers who prioritize Relationship Capital have an edge that endures.

Let’s go back to Pirate Linda.

Pirate Linda’s dreams came true.

She studied Chemical Engineering because it was the hardest challenge.

She became an analyst at Oliver Wyman (then, Mercer Management Consulting), where she did amazing work for 5 years optimizing direct store delivery distribution, organizational design, and brand work.

She niched down in growth strategy at The Cambridge Group, where she met Pirate Eddie. She later became CMO at The Cambridge Group, then co-authored a piece on Category Design with Pirate Eddie that was featured in the HBR magazine.

Getting into HBR is <1%. Getting into the HBR Magazine is exponentially harder.

Now Pirate Linda runs a solo consulting practice that is more lucrative and rewarding than any role she has ever held.

Her clients, when asked why they hire her, say three words: “You make me better.”

Said differently, she built her Reputation Capital via the strength of her Relationship Capital.

Too many consultants better themselves first, before bettering their clients.

What is more remarkable is that she and her husband raised five children, including two sets of twins, one of whom has Down syndrome and survived cancer. Not to mention serious elder care for her parents.

It’s not just her clients who say, “You make me better.” It’s her kids and family.

“You make me better” is the integrated POV that Linda lives by.

Relationship Capital builds trust.

Trust unlocks opportunities.

Opportunities lead to outcomes.

Motherhood is an Incubator for Intellectual Capital

The conventional wisdom says women stopping work to have children hinders producing Intellectual Capital.

In reality, moms are forced to create massive amounts of Intellectual Capital.

We just don’t call it that.

What’s the difference between pets and livestock?

Names.

Languaging.

Moms are constantly learning as they navigate new, unexpected challenges with raising children. Moms are managing more people with the same 24 hours in the day. Moms work feverishly to produce outcomes (e.g., is my child gaining weight? Is my child in the right school?)

Constant learning. Time management. Outcome orientation.

Sounds like a ton of Intellectual Capital to us.

Meet Pirate Mimi Klosterman.

She was a Strategy Therapy pirate. Pirate Mimi homeschooled her eight children over 27 years. Most people would call that mothering. Mimi calls it R&D.

She watched parents flood out of traditional schools as kids got hammered by anxiety, bullying, and one-size-fits-all curricula that ignored autistic, dyslexic, ADHD, and gifted learners. She saw the same parents drowning in 100 curriculum options with no map.

But she’d already built the map over twenty-seven years.

So she productized it. Best School Options is Mimi’s Skool community, where parents stop guessing and start designing the education their kid was always meant to have. The free tier is the Explorer Roadmap, a $297 course given away to get parents in the door. The Collective is the $397/month live Q&A layer for parents who want guidance on their real situation. Underneath is her bigger play, Deschooling Hub, the “Netflix of learning” she’s building with tiered access, expert-led video, and TERA, an AI assistant that profiles each child’s strengths and learning style to design a personalized plan.

Mimi did not pause her career to mother. Her mothering was her career.

She compounded Intellectual Capital for 27 years before she ever charged a dollar for it. Now she’s monetizing it while she sleeps, helping the next wave of parents skip the part where they feel lost. If you’re a parent staring at a blank calendar wondering what comes next, here is her website and email her at mimi@bestschooloptions.com.

And if you’d like a free Scooby Snack, you can get it here!

As Pirate Tom Schwab says, what is ordinary to you is extraordinary to others.

These seem like routine acts of mothering. In reality, moms are constantly creating Intellectual Capital.

What’s not always happening is the conversion of Intellectual Capital into a digital asset that makes them money while they get what little sleep they can get.

Intellectual Capital Integrates Your Career and Motherhood

The conventional wisdom says career and motherhood are a zero-sum trade-off.

We reject the premise.

The Four Capitals, Financial, Reputation, Relationship, and Intellectual, don’t compete across these domains.

They compound.

For moms, they compound in a different sequence.

Relationship Capital first. Then Intellectual Capital. Then Reputation and Financial Capital.

Consultant Linda and Mom Linda are not two different people.

They’re the same person with the same superpower.

As she put it, “I view my children almost like a consulting experience. I can at all times tell you what their strengths are, what their weaknesses are, because in each of these cases, you are a real-life consulting project as it were to maximize what gives you joy, to maximize your outcomes, to leverage your skills and refine them, and then just smooth out the edges of your challenges.”

Her husband laughs about it. Her kids joke about it. But it works. Because the same posture that makes her invaluable to clients (smart, humble, your outcomes ahead of hers) is exactly what makes her the kind of mom whose children are thriving.

“That which I am learning and refining on a parenting and a home basis is that which I can deploy in a business setting as well. And that which I’m learning in the business setting, I redeploy back again to my family life.”

The Three Traps that Cause Smart Women to Stall

If moms already have the four capitals to be extraordinary Creator Capitalists, then why aren’t more of them?

Why isn’t Motherhood 3.0 already a thing?

Because three traps keep them stuck.

Let’s go through each one at a time.

Trap 1: The Waiting Trap

Read more

Arrrrr! 🏴‍☠️ Welcome to a Wednesday Founder Post of Category Pirates. Each week, we share radically different ideas to help you design new and different categories. Founding subscribers can access the entire archive of 200+ mini-books, The Pirate Eddie Bot, copies of our Big Books, and audiobooks. If you’re not a paid subscriber, hop aboard!

Subscribe now

Dear Friend, Subscriber, and Category Pirate,

Last week we introduced you to the first nine pirates from Cohort 3.0 of the Category Design Academy. This week, we’re back with the rest of the crew.

If you missed Part 1, you can read it here. Same rules apply. These pirates spent five months getting uncomfortable on purpose, reframing their businesses, raising their prices, walking away from the wrong clients, and jamming with each other in a way that turned a cohort into a crew.

Without further ado, here are the rest of the Category Design Academy 3.0 graduates:

Meet Sylvia Bowman

Sylvia’s Category: Flooring Integrity Service

Sylvia came into the Academy with three decades of expertise the rest of the construction industry quietly relies on and rarely names. She’s a commercial flooring expert who has spent her career watching building owners pay twice for the same floor, once when it gets installed wrong, and again when it fails.

Buildings get commissioned. HVAC gets commissioned. Electrical gets commissioned. But the floors, the surface every occupant touches every day, often get installed without anyone independently validating that the substrate, the moisture levels, the adhesive, or the warranty terms match what the building actually needs. So when the floor fails two years later, or fourteen years later, the building owner foots the bill while the manufacturer points at the installer and the installer points at the substrate.

Sylvia’s category is naming that gap and owning it. Flooring Integrity Service. A non-biased third party that works alongside the contractors during install to make sure the integrity of the floor matches what the building owner is paying for. The unintended consequence of getting this wrong is six and seven figures of rework on every major project. The cost of getting it right is a fraction of a percent of the flooring budget.

Sylvia’s Academy Wins

• Coined the Flooring Integrity Service and the Flooring Integrity Report as the languaging for the category she now owns, with neutrality as the central feature, because the contractor and the GC have no incentive to flag their own mistakes

• Anchored her POV in the line that finally explained what she does: spotting the unintended consequence created by today’s solution, the framing she pulled from chapter 11 of Creator Capitalist, and made her own

• Identified the building owner, the director of capital projects at a university, the school board, the developer of a hospital, as her actual Superconsumer, not the GC, because commissioning by definition has to be independent of the people doing the work

“Building owners don’t know what they don’t know. That’s not their fault. It’s the industry’s fault. And I’m done watching them pay for it.”

The Flooring Integrity Method

Sylvia’s superpower is making invisible expertise visible to the people who need it most. Most building owners hire a general contractor and assume the floors will get handled. They don’t. They get installed, which is a different thing.

Her three-move sequence: Build the economic argument, because a Flooring Integrity Service that costs a fraction of a percent of the flooring budget but prevents six and seven figures of rework is a barbell nobody can argue with. Validate during install, because the moment to catch a moisture issue is before the adhesive goes down, not after the floor is failing. Deliver the Flooring Integrity Report at the end, because the building owner needs documentation that’s non-biased and survives every change of contractor, manager, and warranty claim that follows.

You can learn more about Sylvia and her work here.

Meet Eric Hanson

Eric’s Category: Dual Use Technology for Military Medicine

Eric is a physician, a 17-year Air Force flight surgeon, and the founder of MilMed Connect, a Techstars portfolio company that lives at the intersection most people didn’t know existed. The intersection between high-growth life science companies and the part of the U.S. military that actually buys things.

Most med tech, biotech, and pharma companies are focused on the civilian market. Of course they are. That’s where the cap rates are. But Eric has spent 14 years quietly proving that there’s a parallel game running underneath the civilian one. Build a version of your technology that meets military operational requirements, what the field calls C-SWaP (cost, size, weight, and power), and the U.S. Department of Defense becomes the largest non-dilutive funding source most CEOs have never seriously considered. Roughly $40B a year flows through the SBIR program. The Congressionally Directed Medical Research Program puts another $1.27B into play in fiscal year 26 alone.

Eric’s category is dual use technology, the discipline of translating civilian life science innovation into military operational settings. His business is the operating system that helps a small group of CEOs do it well.

Eric’s Academy Wins

• Sharpened the Superconsumer to the CEO of a Series A med tech, biotech, or pharma company who has raised $2M to $20M and is ready to commercialize, and who can be coached toward a dual use product roadmap their existing investors hadn’t considered

• Productized 14 years of proprietary expertise into Navigator, a no-to-low-code platform that walks five clients at a time through funding roadmaps, industry partnerships, and the labyrinth of DOD acquisition, with an AI agent layer (Curly Bot, Eric Bot, dual use triage bot) coming online in 2027

• Built a parallel audience and trained 50 military medical veterans (docs, nurses, pharmacists, dentists, special op medics) to work with industry, of which 25 have already started or augmented their own companies, an extension of MilMed Connect that scales the model rather than the founder

“Our goal is to create an operating system for CEOs around dual use technology.”

The Dual Use Method

Eric’s superpower is that he sits inside two cultures most people only ever see one of, the military medical community and the high-growth life science venture community. He speaks both languages fluently. The military trusts him because he served. The CEOs trust him because he has captured over $300M in non-dilutive DOD and federal funding for med tech, biopharma, digital health, and medical countermeasure companies.

His three-move sequence: Find the CEO who actually wants this, because dual use only works if the CEO is committed, not just curious. The conversion rate is roughly one in ten serious conversations. Identify the C-SWaP version of the product, because the military doesn’t want your civilian product. They want the smaller, lighter, lower-power, edge-compute, AI-assisted version of it that a medic can use 72 hours into prolonged casualty care. Stack the four capitals, financial (non-dilutive funding), relational (DOD networks), reputational (military validation), and intellectual (14 years of pattern recognition), into a single roadmap the CEO couldn’t build alone.

You can learn more about Eric and MilMed Connect here.

Meet Richard Poolman

Richard’s Category: Category Decisions That Meet GTM Execution, for AI-Native and Enterprise Software in Europe

Richard is the rarest kind of grad, the one who walked into the Academy with a 25-year track record of building European GTM engines from zero at companies like ServiceNow, Snowflake, Tanium, and Quantexa, and walked out asking himself a different question than the one he’d been asking for two and a half decades.

The question Richard used to ask: where can we improve pipeline, messaging, sales execution, and team structure?

The question he asks now: are we solving the right problem in the right category?

If the answer is no, better messaging won’t fix it. More pipeline won’t fix it. Hiring more sales won’t fix it. He’s seen it more times than he can count, strong companies stuck not because they lack execution but because the market sees them through the wrong lens. Execution cannot fix a broken frame. He is now the guy who fixes the frame before scale makes it expensive.

Richard’s Academy Wins

• Reframed his entire operating premise from optimizing GTM execution to diagnosing category fit before execution

• Took the lessons of Category Design into his existing work with leadership teams in AI-native and enterprise software companies, sharpening conversations about which category to own and which framing to abandon

• Identified his next chapter as working with founders and GTM leaders who know something is off but can’t yet see it clearly

“Don’t start with solutions. Don’t start with GTM. Start with the problem you want the market to see. Once that’s clear, everything downstream becomes easier.”

The Category-Before-Execution Method

Richard’s superpower is recognizing the moment a company’s positioning has stopped working. A positioning that worked at Series A becomes drag at Series C. A market narrative generates attention but not budget. Teams optimize execution inside the wrong game. Most operators don’t see it because they’re inside it. Richard sees it because he’s been inside it five times before.

His three-move sequence: Diagnose the category, not the company, because the company is usually not the problem. Decide the framing to abandon before deciding the framing to claim, because most companies are carrying old positioning like dead weight. Translate category into revenue design, because category clarity that doesn’t show up in pricing, packaging, and pipeline is just a deck.

“AI increases speed. It does not replace judgment about where to point the company.”

You can learn more about Richard and his work here.

Meet Judith Schroder

Judith’s Category: The Contract Velocity Framework for Material Impact Contracts

Judith is a lawyer in Europe with 25 years of experience working on contracts for company owners, from small enterprise to large. She came into the Academy doing what most lawyers do, billing in six-minute increments. She left building something completely different.

Her category is the contract velocity framework for material impact contracts. Not legal advice. Not contract drafting. AI can do those. What AI cannot do, and what Judith has spent 25 years getting good at, is the de-escalation work that happens when a multi-million dollar contract starts to break down. When the parties are angry. When the wrong move forward is a “pissed off letter” and the right move forward is a strategic conversation that nobody else is brave enough to have.

That work has a name now. Contract velocity. And Judith owns it.

Judith’s Academy Wins

• Coined “the contract velocity framework” and “material impact contracts” as the language for the category she now owns

• Reframed her pricing from hourly billing to a Good-Better-Best structure that charges a fixed fee tied to outcomes on contracts measured in millions of euros

• Identified de-escalation as her actual superpower, not contract drafting, and started leading with it

“I’m not the best drafter, but I don’t need to be the best drafter, because everyone has AI already. It’s strategy in conflicts. That’s where I make the difference.”

The Contract Velocity Method

Judith’s superpower is what most lawyers refuse to do, treat the contract as a relationship rather than a document. Most contract disputes get worse because both sides escalate to win. Judith de-escalates so both sides can finish.

Her three-move sequence: Diagnose the breakdown drivers, because there are always three reasons a contract is collapsing and most clients can only see one. Apply the velocity framework, because contracts have a lifecycle and if they don’t get done in a certain window they don’t get done. Force a fund-or-walk decision in a week, because the worst outcome is a contract that drifts for six months and ends up worse than walking away.

“I felt like a social worker 90% of the time. Now I charge for it.”

You can learn more about Judith and her work here.

Meet Karthi Ratnam

Karthi’s Category: Impact Category Design and the Productivity-to-Capacity Reframe

If you ever want a master class on what it looks like to take Category Design and rebuild it from first principles for your own work, spend an hour with Karthi Ratnam. The Cohort 3.0 standout, the godmother of impact category design, the person who has spent six years adding impact to the Magic Triangle and getting away with it because she’s right.

Karthi’s lens on Category Design is this: most companies are stuck in a false binary between profit and purpose. You can do well or you can do good. Pick a lane. She refuses the lane. She has spent her career proving that the right unit economics, applied to the right category, with the right point of view, lets you do both. And she has a phrase for the people who don’t believe her.

“You don’t have to be poor to be a good person.”

She also has a phrase for the people stuck inside the productivity treadmill, which is most of the GTM world. The reframe is simple. Sales isn’t failing because reps don’t write emails faster. CROs don’t start the year with productivity planning. They start with capacity planning. So why is every AI company selling productivity?

Productivity to capacity. That’s the FROTO Karthi unlocked.

Karthi’s Academy Wins

• Reframed her own Lightning Strike work for an enablement-focused AI company from “we make reps more productive” to “we unlock revenue capacity without adding headcount”

• Built a new identity for the buyer of that work, the revenue activator, which moved enablement leaders out of the support function correlation map and put them directly on the cause map for revenue

• Coined her own variant of category design, impact category design, which adds societal impact as a fourth side to the Magic Triangle and refuses the profit-or-purpose binary

“I never trade my time for value. I don’t go looking for jobs. People come to me. People who matter know me. People who don’t know me probably shouldn’t know me.”

The Impact Category Design Method

Karthi’s superpower is making smart people uncomfortable in a way they thank her for later. She thinks marketers should read scripture, because scripture is the only POV that has scaled across every civilization, geography, and culture that humans have ever built. And she thinks marketers should learn from nature, because nature is the only system that has shipped more category-defining innovations than any human ever has.

Her three-move sequence: Reject the premise of your own category, even after you’ve built it, because if you can’t reject the premise of Play Bigger after reading it, you’re not actually a category designer. Anchor in aspirational value at scale, because the question isn’t whether your customers want what you make. The question is who they get to become if they have it. Build the recursion loop with AI, because the operators who win the next decade are the ones treating AI as a thought partner that scales judgment, not a tool that scales output.

You can learn more about Karthi and her work here.

Meet Chris Stanley

Chris’s Category: The Renewable Auto Estimating Workforce

Chris spent ten years building IA Path, a training program helping new adjusters and estimators break into the auto insurance and collision industry. The whole time, he kept asking the wrong question. The question he kept running into wasn’t “how do we train more people.” It was bigger.

Why is the industry pipeline broken?

The Academy helped him name what he was actually building. The category isn’t adjuster training. The category is the Renewable Auto Estimating Workforce.

Chris’s villain is the Fossil Workforce, a generation of adjusters, appraisers, and estimators who built the insurance and collision industry from scratch. They weren’t trained. They were shaped. Time in the seat. Pressure from carriers, shops, and claimants. Years of feedback that was sometimes a mentor and sometimes just a bad estimate getting kicked back. That’s how the entire knowledge base of the industry was built. Informally. Inconsistently. Invisibly.

And right now, one in four of them retires by 2027.

The industry doesn’t have a talent crisis. It has a design failure. Chris is the one designing the fix.

Chris’s Academy Wins

• Reframed his work from “adjuster training” to the Renewable Auto Estimating Workforce, which moves the conversation from labor supply to industry redesign

• Coined the Fossil Workforce as the villain, naming the cohort that’s quietly aged out of the industry without anyone replacing the knowledge they carry

• Built the Contribution Standard as the measurement layer for the new category, “not what you know, what you can contribute from day one”

“The fossil workforce was built by time and pressure. The renewable workforce is built by design.”

The Contribution Standard Method

Chris’s superpower is recognizing that the entire training conversation in his industry is built on the wrong unit of measurement. Most industries grade new entrants on what they know. Chris grades them on what they can contribute. The distinction sounds small. The implications are massive. It changes who can enter this career, how fast they can do it, and what happens to the industry when the fossil workforce finally walks out the door.

His three-move sequence: Name the workforce design failure, because nobody else in the industry is calling it that. Build the new workforce by design, not by accident, because the previous generation was built by pressure and the next one cannot be. Measure by contribution, because contribution is the only signal that scales when knowledge can no longer be transferred informally.

You can learn more about Chris and IA Path here.

Meet Henrik Hjelte

Henrik’s Category: Community Fashion (From Choice to Voice)

Henrik came into the Academy as the CEO of a blockchain company planning a Lightning Strike for an AI idea. Then his board kicked him out. So he did what most ex-CEOs don’t do. He bought an asset off his old company, walked away from software, and pointed himself at one of the largest, oldest, and most top-down industries on Earth. Fashion.

The asset is Black Denny, a leather and denim brand founded in 2011 by Johan Lindeberg, the man behind Diesel’s most controversial ad campaigns of the 90s. Beyoncé wore the jackets. The brand had values rooted in borderless community and creativity beyond borders. And it was sitting there, undervalued, waiting for someone to do something different with it.

Henrik’s category: Community Fashion. The reframe is simple and contrarian. For the entire history of fashion, the conversation has gone one direction. Designer creates. Customer buys. Take it or leave it. The customer’s only real power is to walk away. Henrik’s POV is that customers should have a voice, not just a choice. Buy a Black Denny jacket. Scan the NFC chip with your phone. You now have a vote on what the company does next, where the surplus goes, and what the next drop looks like. Not co-ownership. Co-direction. Like a country, where citizens don’t own the company but they get to elect the people who run it.

He calls it “from choice to voice.” And it’s also a built-in answer to mission drift, because the community has structural power that prevents a future buyer from quietly destroying the values the brand was built on.

Henrik’s Academy Wins

• Coined “from choice to voice” as the POV that reframes the customer’s relationship with a fashion brand from passive purchase to active participation

• Landed on Community Fashion as the category, with Christopher’s framing: “For the entirety of fashion, fashion’s a one-way conversation from designer to client. We’re saying community, where customer gets voice with designer, and customers get voice with each other”

• Built mission drift prevention directly into the legal and governance structure of the brand, so the community has the power to keep the values from being sold off when someone with a checkbook shows up

“Customers are our biggest asset. So why are we treating them like an anonymous wallet instead of a citizen?”

The Community Fashion Method

Henrik’s superpower is treating a fashion brand the way most people treat a country: as something its participants build together, not something a single designer dictates from the top. The first NFC scan is the first vote. Every drop after that is the result of the last vote.

His three-move sequence: Sell the jacket first, because nobody’s buying a governance model. They’re buying clothes that look good and feel right. The voice comes later. Activate the community through the chip, because the NFC scan is the conversion event from buyer to citizen, and that’s where the real category begins. Build mission drift protection into the structure, because the entire promise of community fashion falls apart the moment a future board can override the community.

You can learn more about Henrik and his work here.

If You’re Reading This, Wondering Whether the Academy Is For You

Every one of these grads walked into Cohort 3.0 with a business or a career that was working. They had clients. They had revenue. They had reputations in their industries. None of them needed the Academy to keep doing what they were already doing.

What they needed was a different question.

• Sylvia needed someone to tell her that her job is flooring integrity, not flooring expertise, and that the building owner is her Superconsumer, not the GC.

• Eric needed the language to describe what he had been building for fourteen years inside the dual-use opportunity.

• Richard needed permission to stop optimizing GTM execution and start diagnosing category fit.

• Judith needed to stop apologizing for being a social worker 90 percent of the time and start charging for it.

• Karthi needed the architecture to make her own version of category design make sense to people outside her head.

• Chris needed to stop calling it adjuster training and start calling it the Renewable Auto Estimating Workforce.

• Stacey needed to focus the problem down to the people willing to pay $1,000 a month to use AI less.

• Henrik needed to stop pitching governance and start pitching jackets, and to let “from choice to voice” do the heavy lifting underneath.

If you’ve been doing your work well for a long time and you can feel that the language hasn’t caught up to what you’re actually doing, the Academy is for you. If you’ve built a real category in your industry but you’ve never heard anyone else describe it the way you do in your head, the Academy is for you. If you have a business that works and you suspect it could work an order of magnitude better with the right framing, the Academy is for you.

If you’re looking for tactics, we’re not the right people.

If you’re looking for permission to stop doing what everyone else in your industry is doing and start owning a category that’s actually yours, hop aboard.

Arrrrrrr,

Category Pirates

Eddie Yoon

Christopher Lochhead

P.S. Want to do this work yourself?

Cohort 4.0 started Monday. Cohort 5.0 is a long time to wait while every grad above pulls further ahead of where you currently are.

The good news is, you don’t have to wait.

The Pirate Eddie Bot is trained on every mini-book, every framework, every jam, every piece of category design IC we’ve ever published. Ask it about your villain. Ask it to tear apart your tagline. Ask it to help you find the FROTO in your offer. Ask it the questions Sylvia asked, the questions Eric asked, the questions Richard asked, the questions Judith asked, the questions Chris asked, the questions Stacey asked, the questions Henrik asked. It will do for you what it did for them.

The Pirate Eddie Bot lives behind the Founding subscriber door. Become a Founding subscriber here and start jamming today.

If you’d rather do the work in a cohort, you’ll have to wait for cohort 5.0 to open.

Dear Friend, Subscriber, and Category Pirate,

We did something different this episode.

Pirate Eddie wasn’t here. Pirate Christopher wasn’t here. Pirate Bri sat down with five of the most formidable Creator Capitalist moms in our pirate ship and let them run the conversation.

Pirate Alexis Skigen Rago. Built her business eight years ago after Corporate America made her ask permission to volunteer in her own kid’s classroom. Mom of two boys, ages 14 and 18.

Pirate Melissa Andrews. Building and scaling across continents while her 19-year-old (autistic, brilliant) and her 17-year-old (off at boarding school by choice) keep her honest. 4 a.m. starts and 1 a.m. calls to five continents.

Pirate Jennifer Hall Thornton. Ran the everything-but-sales side of a digital company while raising two kids 13 months apart, an elderly mother nearby, and a husband on a plane. Now relaunching with the four capitals as her map.

Pirate Mary Kathryn Johnson. Started her first business in 2003 with an 18-month-old and a 4-year-old, a Bob the Builder keyboard cover, and a Windows 98 machine. First in her family to go to college. Mom of two grown sons, 24 and 27.

Pirate Lydia Flocchini. Lawyer turned legal-tech category designer. Mom of two (one graduating college, one graduating high school in the same season).

Five women. Three Academy cohorts. One conversation that should be required listening for every mom (and every man married to one) in our orbit.

Here’s the thesis they landed on, and we couldn’t have said it better ourselves:

The most undervalued asset on the planet is the work moms have been doing for free.

The volunteer hours. The household OS. The school logistics. The relationship capital built on the sidelines of a soccer game. The reputation capital compounding inside a PTA that’s secretly a Fortune 500 in disguise.

Society has spent a hundred years telling moms that work doesn’t count. Five Creator Capitalists in this episode just called bullshit on that, on the record.

Mothering and Creator Capitalism run on the same playbook.

If you’ve read Creator Capitalist, you already know the four capitals. What you haven’t seen is what happens when five moms apply that lens to the work they were never paid for, the kids they’re raising into a world that hasn’t been invented yet, and the businesses they’ve built (or are about to).

Each of them has a different on-ramp into the same conversation.

• One is using AI as a translation layer between her neurotypical brain and her neurodivergent kid’s.

• Another is watching her son weaponize Claude inside an upper-division engineering class he isn’t technically qualified to take.

• A third is helping her daughter category design a Shopify store before she’s even old enough to vote.

We’re not going to spoil the answers here. They’re better when you hear them tell it.

What we will tell you is this:

A category nobody’s named yet came up in the middle of the conversation. A new framework for how to think about the people you build with. A moment where one of our Pirates basically pitched an entire business live on tape without realizing it.

And by the end, the five of them had quietly written a starter kit for any woman watching from the sidelines who’s been told her work doesn’t count.

A 3-step starter kit for any mom watching from the sidelines.

If you only walk away from this episode with one thing, walk away with this:

1. Make up a company name. Even if you never use it. Then write your last 10 years of “non-paid” work as if you were the CEO of that company. The volunteer board seat. The household operations. The school logistics. The unpaid emotional and logistical labor. You’ll be staring at a resume that would get hired in any sane economy.

2. Build a personal board of directors. Three to seven people. Not your spouse. Not your best friend. People who will give you the unvarnished truth, point you at opportunities, and amplify the value you can’t yet see in yourself.

3. Pick a structure. A framework that helps you think instead of letting you spin. Creator Capitalist is one option (we’re biased). The Academy is another. Pick the one that forces you to do the work and stick with it long enough for it to click.

The why behind each step is in the conversation, and it’s a lot more interesting hearing five women who’ve actually run the play talk it through than reading us summarize it.

Here’s how to navigate this conversation:

• 02:30 – The empty nest math: What boarding school, college roommates, and “I dream of being an empty nester” actually reveal about the seasons of a Creator Capitalist’s life.

• 08:30 – Digital natives vs. analog natives: Why the way our kids build relationships looks nothing like ours did, and why that’s a feature, not a bug.

• 12:30 – Hire your kid: The case for bringing your kids inside the business early, what role to give them, and the moment Mary Kathryn realized her teenager could outproduce most adults.

• 18:30 – The IBM dad and the entrepreneur mom: Why the kids of Creator Capitalists are absorbing a completely different operating system than the one we grew up with.

• 24:30 – The oxygen mask: Why moms are running on fumes by 40, who’s actually paying for it, and the line in the sand the women in this conversation are finally drawing.

• 33:30 – AI as the mom translation layer: Two stories about neurodivergent kids and the AI use case nobody is writing about yet. Worth the price of admission alone.

• 42:00 – The data drop: What’s happening to women’s access to capital right now, why it’s going the wrong direction, and what these five are doing about it.

• 45:30 – The new business hiding in plain sight: Pirate Jennifer names a category live on the recording. We won’t spoil it. You’ll know it when you hear it.

• 50:30 – The value of your value: The line of the episode, courtesy of Pirate Mary Kathryn. If you only press play for one moment, make it this one.

• 1:00:00 – Walking the starter kit: Five Creator Capitalists working through why each move matters, what they wish they’d known earlier, and the one piece of the kit each of them resisted the longest.

To connect with our Creator Capitalist Moms:

• Follow Pirate Lydia Flocchini on LinkedIn

• Follow Pirate Alexis Skigen Rago on LinkedIn

• Follow Pirate Melissa Andrews on LinkedIn

• Follow Pirate Jennifer Hall Thornton on LinkedIn

• Follow Pirate Mary Kathryn Johnson on LinkedIn

Arrrrrr,

Category Pirates 🏴‍☠️

Eddie Yoon

Christopher Lochhead

P.S. — Mother’s Day is coming up.

If you want to gift the mom in your life something genuinely valuable, or if you are the mom and you’re looking to start creating value of your own, the best place to start is with the Pirate Eddie Bot.

It’s the fastest way we know to put the four capitals to work in your life, your career, and your relationships, without waiting for permission from anyone.

→ Become a Founding Subscriber to get access to the Pirate Eddie Bot here.

Arrrrr! 🏴‍☠️ Welcome to a Wednesday Founder Post of Category Pirates. Each week, we share radically different ideas to help you design new and different categories. Founding subscribers can access the entire archive of 200+ mini-books, The Pirate Eddie Bot, copies of our Big Books, and audiobooks. If you’re not a paid subscriber, hop aboard!

Subscribe now

Dear Friend, Subscriber, and Category Pirate,

A new wave of pirates just walked the plank into category design legend.

Cohort 3.0 of the Academy graduated on April 1st, 2026, and to call this group “impressive” would be the kind of lazy, comparison-game language we’d kick out of a workshop. These pirates spent five months getting uncomfortable on purpose. They reframed their businesses. They raised their prices. They walked away from clients who weren’t ready. They built brands, books, board strategies, diagnostic tools, and entire new advisory practices. And along the way, they jammed with each other in a way that turned a cohort into a crew.

A quick note before we get to the spotlights:

This post is Part 1 of 2. We have more graduates than we can fit into a single sub-stack post without burying everyone, so we’re splitting it up. Part 2 will follow with profiles of the rest of the crew. If you’re a Cohort 3.0 grad and you don’t see yourself here yet, you’re up next.

We’ve also said this before, and it bears repeating: the Academy isn’t a course where you watch some videos and get a certificate. It’s a five-month commitment to thinking about your thinking, getting feedback you didn’t ask for, and choosing painfully different over painfully the same. Every pirate below made that choice.

Without further ado, here are some of the Category Design Academy 3.0 graduates:

Meet Mike Harker

Mike’s Category: Category-First Brand and Product Studios for Agencies That Refuse to Be Commodities

Mike runs ThoughtLab, a digital agency he’s been building for 26 years. He came into Cohort 3.0 with a hunch and left with a hammer.

The hunch: most agencies (and most of their clients) are pretty and dumb. They show beautiful renderings, they talk like everyone else, and if you covered the logos on their proposals, you couldn’t tell them apart. The hammer: a complete rebrand of ThoughtLab from “brand-first digital agency” to “category-first brand + product studio,” with vertical sub-brands (like Archipod for the architecture, engineering, and construction industry) for niches that warrant their own positioning.

Mike’s reframe came in two parts. First, he stopped describing himself as a digital agency and started describing himself as a category-first brand plus product studio. Second, he started telling clients the truth that nobody else was telling them, that being forgettable is the real consequence of being a commodity.

Mike’s Academy Wins

• Made the top 2 of 3 finalists on a $1.3 million RFP for Lutheran Hour Ministries, competing against two faith-based agencies as the non-faith-based outsider

• Reframed a 26-year-old digital agency into a category-first brand and product studio, with sub-brands for specific niches

• Repositioned proposals so that, in his words, “they literally can’t compare us”

“It’s the first time in my entire history of 26 years I’ve felt that clear that they can’t compare us. And I’m having fun doing it.”

The Painfully Different Method

Mike’s category superpower is telling clients what their friends and competitors won’t. His point of view, refined over months of jamming with the crew, lands on a simple choice: painfully the same, or painfully different. Pick one.

He frames it through three moves. Niche down hard, because there is a real difference between competing against millions of digital agencies and competing against two. Lead with category, not brand, because branding without a point of view is just a nicer paint job on a commodity. Make yourself uncomparable, because the goal isn’t to win the bake-off, it’s to refuse to enter one.

You can learn more about Mike and his work here.

Meet Markham Rollins

Markham’s Category: Retirement Drift, the Problem Nobody Admits They Have

Markham came into Cohort 3.0 with something most graduates don’t have, a YouTube channel with over 1.5 million views and a real audience already calling his category by name in his comments. What he didn’t have was the full architecture, the book, the lightning strike, the integrated offer.

He left with a plan to build it.

Markham and his partner Jody run Retirement Transformed, a multi-format business helping people in their 50s, 60s, and 70s solve the problem nobody wants to admit they have. They’re bored. They’re lonely. They’re lost. They have all the money. They did everything they were told to do. And now they’re staring at 30 more years of life with no script for what to do with them.

That problem has a name. Retirement Drift. Markham Framed, Named, and Claimed it. And his audience is already uses it back to him in the comments of his YouTube videos.

Markham’s Academy Wins

• Validated his pricing reframe from $895 to $1,495 for the eight-week masterclass after running it through the Academy’s pricing pressure-test

• Confirmed the architecture for a full integrated offer: the book, the course, the community, the AI bot, all under the Retirement Drift banner

• Started planning a 2026 lightning strike for a Retirement Drift book, modeled on the Category Pirates Creator Capitalist launch

“We’re solving a problem that people don’t really know they have, and they definitely don’t want to admit they have it. They don’t want to say they’re bored. They don’t want to say that they’re lost. They don’t want to say they’re lonely. But it’s a serious problem.”

The Drift Method

Markham’s approach is to refuse the comfortable euphemisms that the retirement industry has trained everyone to use. Nobody wants to say “I’m drifting.” Nobody wants to say “I made it and I’m miserable now.” Markham makes the conversation safe by giving the problem a name that’s accurate but not shameful.

His three-move sequence: Name the drift, because the unnamed version is the dangerous one. Build the routine, because 28 out of 35 of his masterclass alumni said the morning routine was the single biggest unlock. Expand the seven pillars, because retirement isn’t a financial event, it’s seven different transitions happening at once (physical wellness, mental wellness, relationships, vision, passion, purpose, and one more depending on the person).

You can learn more about Markham, Jody, and Retirement Transformed here.

Meet John Wilson

John’s Category: Scale Signals for Companies Drowning in Insights

John came into the Academy with one of the cleanest reframes of the entire cohort. He spent decades watching companies pay six and seven figures for “consumer insights” that didn’t actually predict anything. The deck would land on the CEO’s desk. Everyone would nod. Nothing would change. The insights were directionally true and directionally useless.

John’s POV is that companies aren’t suffering from a lack of insights. They’re suffering from too many. Every PowerPoint, every dashboard, every customer interview produces a new “insight” and the executive team has no way to tell which ones predict scale and which ones predict nothing.

So John reframed the entire category. Stop calling them insights. Start calling them scale signals.

A scale signal is an insight that predicts. An insight that doesn’t predict is just an opinion with a confidence interval. By renaming the category, John gives executives a sharper way to triage what’s on their desk. Most of what they’re looking at isn’t a scale signal. And the few signals that actually are signals deserve disproportionate attention.

John’s Academy Wins

• Coined and locked in “scale signals” as his category language, replacing “consumer insights” and “market research” with a sharper, more accountable frame

• Pressure-tested the language with multiple clients during the cohort and watched it land every single time

• Started building IC around how to spot a scale signal versus a directional insight you can safely ignore

“Insights are everywhere. Scale signals are rare. The whole industry is calling everything an insight, and that’s the problem.”

The Scale Signal Method

John’s superpower is filtering noise from signal in companies that are addicted to noise. Most consumer insights teams are funded to produce insights, which means they produce them whether the insights are predictive or not. John’s frame forces a different question, can this insight predict scale, or is it just true?

His three-move sequence:

1. Define the scale event the company is trying to cause.

2. Inventory every “insight” against that scale event.

3. Remove the insights that don’t predict and double the budget on the ones that do.

Most of what gets killed is the stuff the company has been celebrating. Most of what gets doubled is something the team had been ignoring.

You can learn more about John and his work here.

Meet Nick Kringas

Nick’s Category: AI Business Development for Lawyers

Nick has lived through more pivots than most people have had jobs. His parents owned a restaurant that closed when the GM plant shut down. He helped them open another one. He left to start an SEO agency. He moved that agency from offline-to-online clients, then from defense to plaintiff law, and now he’s pivoting again, from SEO to AI.

The pattern is the pattern. Nick is the pivot guy. So when he came into the Academy, the question wasn’t whether he had a category. It was which one to claim.

He claimed two.

The first is “are you AI invisible?”, which is his current company’s category. SEO is dying. AI is replacing search. Law firms still need leads, and the firms that figure out AI-driven business development first will dominate. Nick is teaching them how. The frame is sharp because it sidesteps the entire SEO conversation by declaring SEO over and replacing it with a new acronym lawyers can latch onto.

The second is The Pivot Problem, which is the bigger category he’s been living for 20 years without naming. Founders facing contraction, transitions, dying markets, dead categories. They know they need to pivot. They don’t know how. Nick does, because he’s done it five times.

Nick’s Academy Wins

• Coined “are you AI invisible?” as the replacement category for SEO in legal marketing, and started using it in client conversations immediately

• Identified “The Pivot Problem” as the through-line of his entire career, opening up a much bigger advisory category beyond his current legal work

• Reframed his agency’s positioning from “SEO for lawyers” to “AI is the co-founder of your business,” which moves the conversation from defense to offense

“Most people just kind of sit there for too long and it gets worse and worse. The minute you know it’s time to pivot, it’s already too late.”

The Pivot Method

Nick’s frame is that there are good pivots and there are panic pivots, and the difference is timing. Good pivots happen when you start to question your commitment to the category, which is the earliest signal. Panic pivots happen when you have three months of cash left, which is far too late.

His three-move sequence: Diagnose the category, not the company. Most founders blame their company when the real problem is the category they’re stuck in. Replace the language before you replace the offer. SEO becomes AIBD. Search becomes prompt. Insights become scale signals. Move while you still have runway. The pivot done from strength looks nothing like the pivot done from desperation.

You can learn more about Nick and his work here.

Meet Eddie Geller

Eddie’s Category: Profit Leak Diagnostics for High-Performing Teams

Eddie Geller runs SKOR, and when he came into the Academy, he was selling what he called a “team assessment platform.” Eddie called it a lame pitch himself. The Academy made him kill it.

What Eddie discovered through six months of jams was that nobody buys a team assessment. CEOs buy outcomes. So Eddie reframed his entire offer around a much sharper villain: profit leaks in your teams. Not engagement. Not culture. Not soft stuff. Hard money, leaking out of the bottom line because of team dysfunction that nobody can see.

He launched the Profit Leak Calculator at getskor.com, a free 10-question diagnostic that takes a CEO three minutes and shows them, in dollars, what their team dysfunction is costing them every year. The category positioning is built on Eddie’s seven muscles of high-performing teams framework, and the visceral reaction has been undeniable. People take the diagnostic. They get the score. And they reorder how they think about their teams.

Eddie’s Academy Wins

• Reframed his value prop from “team assessment” to “profit leaks in your teams,” with a tagline, visual identity, and conference strategy all built around the new positioning

• Launched the Profit Leak Calculator at getskor.com, a free diagnostic that converts CEO interest into qualified pipeline

• Built and refined the “seven muscles of high-performing teams” framework as the spine of his methodology

• Booked two conferences in six weeks to evangelize the new category

“Everything’s about profit leaks. Our visual is about the leak. Our positioning is about the profit leak. Our tagline is profit leak.”

The Hidden Profit Method

Eddie’s superpower is showing CEOs the money sitting on the floor that they can’t see. Most engagement surveys produce a fifty-page deck nobody reads. Eddie produces a number. A real, actual dollar figure. And the dollar figure is always bigger than the CEO expected.

His three-move sequence: Quantify the dysfunction (because CEOs will believe a number before they believe a feeling). Connect behavior to bottom line (so the conversation moves from HR’s office to the CFO’s office). Diagnose by muscle, not by mood (because his seven-muscle framework gives the team a map for what to fix first).

You can take Eddie’s Profit Leak Calculator at getskor.com and learn more about his work here.

Meet Mary Kathryn Johnson

Mary’s Category: Uncompetitionable for Women Reinventing Themselves at 40+

Mary came into the Academy with puzzle pieces scattered across decades. A podcast. A coined word. A career that had already defied the rules. What she didn’t have was a frame that pulled them together.

She left with one. Uncompetitionable.

Her category is for women between 40 and 60-plus who are reinventing, reentering, or finally realizing they don’t need permission to stop fitting into anyone else’s framework. Mary calls this group out by name and refuses to soften it. She’s the CEO Mischief Maker. Her audience is people who are done shrinking.

Mary’s Academy Wins

• Coined and locked in the category language (”uncompetitionable,” “unmissable”) that she’d been using sporadically for years and finally made the spine of her work

• Drafted a manifesto and started a Substack to flood the zone with content for women reinventing themselves

• Started writing a book with the manifesto as its foundation

“I don’t really give a what anybody else thinks. We’re done. We’re embracing who we are. We don’t need permission.”

The Mischief Maker Method

Mary’s approach is to refuse the comparison game on behalf of her audience. Frame, name, and claim. That’s the Academy’s three-move drill, and Mary applies it to women whose own resumes were written by someone else’s playbook. She helps them rewrite those resumes in their own voice.

She also brings a Christopher-and-Eddie split to her own thinking, which is an interesting tell. The creative side is loud, irreverent, refuses to play small. The systematic side is quiet, organized, knows what outcome it’s chasing. Mary built her offer to honor both. That’s why it works.

“Frame, name, and claim something effectively. Words matter.”

You can learn more about Mary and her work here.

Meet Jill Consor Beck

Jill’s Category: AI-Era Time and Team Design for Executives

Jill spent Cohort 3.0 doing two things at once. Caring for her mom. And quietly rebuilding the way she charges, pitches, and positions herself.

When you ask Jill about her wins, she’ll tell you they weren’t grand. We disagree. The mind shift she described, where she stopped pricing her work by time and started pricing it by outcome, is the single hardest reframe most freelancers and consultants ever make. Most never do it. Jill did.

Her category is now sharpening into something much bigger than time management. It’s executive coaching at the moment AI is forcing every leader to rethink how their team should actually work together. If you’re an executive telling your team to “use AI more” while also forcing them to live in Slack, Jill’s the one who tells you, in language you’ll nod along to, that you’re undermining yourself.

Jill’s Academy Wins

• Reframed her pricing model from time-based to outcome-based, and started saying no to clients who wouldn’t pay for the value she was creating

• Coined the “Savvy Toss” with Pirate Christopher’s help in a jam, used it on sales calls, and turned it into a Substack post

• Pitched her AI-and-teamwork POV to executives at RSA Conference and got real traction

“I learned to charge more. And if they don’t want to pay, well, then it.”

The Collective Time Method

Jill’s superpower is naming the trap that knowledge workers and their bosses are walking into. AI is making existing knowledge and existing execution closer to free every day. Most executives are responding by doubling down on the wrong thing, asking their teams to do more of what AI now does, and burning them out in the process.

Jill’s POV: Don’t optimize for your time. Optimize for collective time. The executives who only save their own time at the expense of their teams will lose their teams. The ones who design systems that save everyone’s time, including the team’s, will be the ones still standing in five years.

You can learn more about Jill and her work here.

Meet Donald Hawthorne

Don’s Category: Naming the Drift Before It Becomes Disaster

Don walked into the Academy with decades of turnaround experience and walked out with something rarer than experience. He had a category.

The villain Don is hunting is Executive Omertà, his own term, an internal corporate code of silence that lets executives feel something is wrong at 3am and decide by 9am to not bring it up. It masquerades as professionalism. It costs companies billions. And Don is one of the few advisors who has lived through enough turnarounds to recognize it before it metastasizes.

His POV is sharp: there are people who lie with lies. There are people who lie with the truth. And there are people who lie with silence. The third group is the most expensive. And it’s the one nobody is willing to call out, until Don walks in.

Don’s Academy Wins

• Coined and refined “Executive Omertà” and “lying with silence” as the category language for the problem he solves

• Took category design into his real-world board work, including a parish school board that’s now reorganizing its strategic direction around the principle of being different, not better

• Pressure-tested his point of view with multiple investor and CEO supers, refining the language each time

“It masks itself as professionalism, being a team player. The reality is, you should just talk about what’s really going on.”

The See What You Can’t Smell Method

Don’s superpower is what he calls being nose blind to your own stinky bets. Most executives can’t smell their own farts, to use the same metaphor Don used in our jam. The Strategy Mirror is his diagnostic to expose the bets that stink before they cost a company nine figures.

His three-move sequence: Diagnose the drift early. Most consultants get called in once the company is on bridge financing, which is too late. Bring the team into the room and force the silent conversation. The one nobody wanted to have in front of the CEO. Force a fund-or-kill decision in 90 days, because letting bad bets drift is the most expensive thing a board can do.

You can learn more about Don and his work here.

Meet Ankit “Kit” Chandra

Kit’s Category: Category Design for Early-Stage Operators (and the Salesperson’s POV on Building Markets)

Kit’s path through Cohort 3.0 is the one that proves the Academy works for people who aren’t trying to be solo consultants forever. He came in as a sales guy with an advisory side hustle. He’s leaving as someone about to step into a senior operating role at a venture firm building agentic AI companies.

In between, he made some money.

Kit went from zero to $45,000 in advisory revenue in four to five months, mostly by teaching category design principles to early-stage founders. He got in front of a VC firm. He started using category design framing to differentiate himself in job interviews, where most sales candidates show up sounding the same.

His next chapter is taking everything he learned about Superconsumers, non-obvious problem framing, and category design and applying it across a portfolio of agentic AI companies competing in a space where everyone is calling themselves “AI native” and nobody is saying anything different.

Kit’s Academy Wins

• Built a category design advisory practice from scratch, generating $45,000 in 4-5 months

• Got in front of a venture firm doing both fund and operate work, and is moving into a senior GTM role

• Started using category design as a hiring differentiator, asking hiring managers questions about Superconsumers and category that no other sales candidates ask

“Category design owns me at this point.”

The Salesperson’s POV Method

Kit’s wedge is that he’s coming at executive operating from a salesperson’s lens, which is rarer than people think. Most CEOs come from sales, but most category design advisors come from marketing or strategy. Kit bridges the gap.

His three lenses for analyzing a market: What’s the problem design that’s commonly accepted? Who are the Superconsumers and what is their most extreme problem? Where’s the weird data that nobody’s looking at? When he applies that to a category like agentic AI for revenue cycle management, he refuses to let his clients say “AI agents” like everyone else. He pushes them to niche down to a specific use case where they can dominate, then expand from there.

You can learn more about Kit and his work here.

As our third cohort of Category Design Academy graduates moves on to owning their categories…

We want to thank these daring Pirates and everyone who embarked on this journey with us.

To everyone in Cohort 3.0, including the pirates whose profiles will land in Part 2: thank you. You showed up week after week, asked the questions you didn’t want to ask in front of your peers, and let us push you to places that probably felt scary in the moment.

What we want for each of you, the same thing we wanted for the 2024 graduates, is for you to keep going. Category design isn’t a phase. It’s a practice. The Academy is the on-ramp to the rest of your life, not the destination.

Cohort 4.0 kicks off May 4th. Applications are closed and the cohort is capped. If you wanted in and missed it, keep reading.

To everyone else reading this who has ever wondered what category design can do for you and your work, these graduates are the answer.

Stay tuned for Part 2.

Arrrrrrr,

Category Pirates

Eddie Yoon

Christopher Lochhead

P.S. Want to do this work yourself?

Cohort 4.0 is closed and starts Monday. But every grad above will tell you the same thing. The real work doesn’t happen in the workshop. It happens between the workshops. At your desk. At midnight. When the doubt creeps in and you have to pressure-test your own POV without anyone there to catch you.

The Pirate Eddie Bot is your in-between.

Trained on every mini-book, every framework, every jam, every piece of category design IC we’ve ever published. Ask it about your villain. Ask it to tear apart your tagline. Ask it to help you find the FROTO in your offer. Ask it the questions Don asked, the questions Mike asked, the questions Eddie Geller asked. It will do for you what it did for them.

The Pirate Eddie Bot lives behind the Founding subscriber door. Become a Founding subscriber here and start jamming today.

If you’d rather do the work in a cohort, the waitlist for Academy 5.0 is open. Add your name here and we’ll be in touch when applications open.

Arrrrr! 🏴‍☠️ Welcome to a 🔒 subscriber-only edition 🔒 of Category Pirates. Each week, we share radically different ideas to help you design new and different categories. For more: Audiobooks | Category design podcast | Books | Sign up for a Founding subscription to ask the Pirate Eddie Bot your category design questions.

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Dear Friend, Subscriber, and Category Pirate,

Dr. Dre is a billionaire.

And most people have never seen him live.

This is the man who gave us “Still D.R.E.,” “Nuthin’ but a ‘G’ Thang,” “Forgot About Dre,” and “The Next Episode.” He was one-fifth of N.W.A. The Chronic sold nearly 6 million copies. 2001 sold almost 8 million. He could have focused on his consumers, ridden the performer track for the rest of his career, toured arenas, and collected checks.

He chose to build a B2B business after his B2C career as a performer.

Dre discovered Eminem from a demo tape that had been rejected by every label in the country. He pulled 50 Cent out of Queens. He signed a skinny kid from Compton named Kendrick Lamar when no one knew who he was.

He didn’t just produce their albums. He designed their futures. He built artist development, sonic identity, marketing, distribution, and a machine that took unknowns and turned them into (mega music) categories of one.

But he didn’t stop there.

He built a B2B2C business called Beats.

Most think of Beats as (just) headphones. But Beats was a streaming service. Beats Music launched in 2014 with a thesis that Spotify thought was insane: human curators over algorithms.

While Spotify built a machine that talked directly to consumers. Dre and Jimmy Iovine put tastemakers and music editors in the middle. Tastemakers who understood artists AND listeners. The people with the judgment, experience, and taste to connect the right music to the right ears. In ways no algorithm could replicate.

(Just like DJs back in the day.)

They trusted and empowered the intermediary. Let human taste do the marketing.

Apple paid $3 billion. Not for 250,000 subscribers. Not for headphones. For the B2B2C platform, which became core to Apple Music. (Which now has over 100 million subscribers.)

Dre could perform. Dre could find talent. But Dre’s real genius? His ability to design and dominate a new category of music ecosystem. That became a powerful flywheel.

Dre is the category designer of B2B2C of hip hop.

(And one of the category designers of the genre.)

Now consider Snoop Dogg.

Snoop is a genius. A cultural icon. His coverage of the Olympics or National Geographic is the stuff of legends. He has a cooking show with Martha Stewart, a wine label, and a weed brand.

Pirate Christopher would love to hang with Pirate Snoop.

Here’s what most people forget: Snoop tried to be Dre.

He launched his own label. Signed artists. Tried to build a machine that discovers and develops talent. It didn’t work.

None of his signings became stars. Not one. Because performing and architecting are fundamentally different muscles. Snoop’s gift is being Snoop. And that’s a spectacular gift. It’s just not the gift that builds systems.

Dre made Snoop. Without Dre producing Doggystyle, there is no Snoop Dogg. The B2B2C created the B2C. The B2C could never create another B2B2C.

(If you’re a board member who just hired a celebrity CEO to run a platform company, go ahead and read that last paragraph again. We’ll wait.)

Now let’s go to Abbey Road.

George Martin is the most important name in rock and roll that (most) people don’t know. He’s called the “Fifth Beatle” because he arranged the strings on Eleanor Rigby, figured out how to record Strawberry Fields Forever backward, and turned four lads from Liverpool into the most sonically innovative band in history.

George Martin was a technical genius.

The greatest studio engineer who ever lived. He took what the Beatles brought him and made it sound like nothing anyone had ever heard. He made great records. He didn’t build the machine that made the Beatles the Beatles.

George was one of the OG B2B CEOs of rock and roll. He was essential, excellent, and invisible to the end consumer.

Snoop, George Martin, and Dre are all incredible talents. All legends. All rich.

But Snoop couldn’t be Dre. Neither could George Martin.

But Dre could be Snoop and George Martin.

Said differently…

• A B2C or B2B CEO likely can’t run a B2B2C business model

• A B2B2C CEO is more likely to succeed in any of the above.

Context is King.

The category of CEO matters.

The category of business model matters.

The combination of context, category of CEO, and category of business model matters most of all.

Back to Business: Pirate Clint as a B2B2C CEO

Pirate Clint Carnell is the Dr. Dre of Medical Aesthetics.

He is the rare success both as an executive and an entrepreneur.

He was one of the youngest VPs at Bausch & Lomb at the age of 30. At the same time, he simultaneously started, scaled, and sold a renal care business. He’s been a CEO and founder more than a half dozen times.

When the Wall Street Journal showcased the new category of medical aesthetics, it listed 10 brands.

1. Botox

2. Fraxel

3. Dysport

4. ADVATx

5. Sofwave

6. Ultherapy

7. Thermage

8. Morpheus8

9. Hydrafacial

10. Clear + Brilliant

40% of the brands bolded above were built by Pirate Clint. From scratch.

Category designing dominant brands is one of his superpowers.

The vast majority of CEOs inherit the brands they run.

And the risk is similar to a trust fund kid. Will they build or waste what they inherited?

Pirate Clint uniquely builds or brings…

• POVs that are easy to remember and repeat, yet pierce through the noise.

• Categories that feel expensive, but are on marketing budgets at ~6% of sales.

• The creativity of marketing with the clarity required by sales.

Did he have great marketing teams and partners along the way? Yes.

But Pirate Clint’s success is in large part because he’s a B2B2C CEO.

That’s the category of CEO he is.

Fraxel, Clear + Brilliant, Thermage, and Hydrafacial were all bought by physicians, spas, or other retail businesses (B2B), but that ultimately served end consumers (B2C).

He also had experience in B2B (Bausch & Lomb surgical) and B2C (OrangeTwist), so he had those clubs in his bag.

But like many great B2B2C CEOs, he knew which playbook to use when.

B2B2C Brands Are The Most Valuable

Some of our B2B or B2C CEO friends might get butt-hurt at this assertion.

So sit down and take a swig of rum.

Interbrand publishes a list of the top global brands.

The analysis is both rigorous and subjective at the same time. It is not perfect, but an imperfect metric that is consistently executed can still be very useful on a relative and directional basis.

We re-swizzled the data and grouped the top 25 brands into B2B2C, B2B, and B2C categories.

• Among the top 10 most valuable global brands, B2B2C brands are 90%.

• Among the top 25 most valuable global brands, B2B2C brands are 60%.

• B2B2C brands in the top 25 are worth $1.3 trillion dollars

• B2C brands in the top 25 are worth $0.6 trillion dollars

• B2B brands in the top 25 are worth $0.3 trillion dollars

Four Reasons Why B2B2C CEOs are Legendary

Are B2B2C CEOs inherently superior to B2B or B2C CEOs?

Not necessarily, but…

• You can more easily put a B2B2C CEO into a B2B or B2C company

• But putting a B2B or B2C CEO into a B2B2C CEO is often a mistake

Especially if they don’t realize the business is a B2B2C business model.

We haven’t done a super-ding-dong academic study robust enough to assert this.

But here’s what we know. From decades in the arena.

B2B CEOs put marketing at the kiddie table.

They worship at the altar of their product and tech. They’d rather spend an incremental dollar on R&D than on marketing. They know they can make the dial ‘go to eleven’ and tell the world that their carbondigulator is 17% faster, cheaper, and better.

Marketing gets told to market the features, throw parties, make leads, and give sales pretty decks to do their jobs.

Nobody gets excited about enterprise demand gen at the CMO Forum. It’s important work, but when was the last time a B2B campaign made you feel something? “Wow, that SAP marketing is legendary”, said no one. In enterprise B2B Marketing is (mostly) a non-strategic service bureau.

That is why we wrote the Big Product Lie.

B2C CEOs let the marketing inmates run the asylum.

They worship at the altar of their brand. CMOs rule the roost and happily spend money on building “brand awareness”. There are plenty of agencies and academics who tell B2C CMOs what they want to hear about brand awareness, so there is plenty of money in the trough for the pigs to feed.

(Brand awareness is an almost useless metric. The good people at SAP pay $3.35 million annually to sponsor the San Jose Shark Tank. Most people who go there have zero idea what they do, will never buy their software, and think the company’s name is about tree sap.)

Marketing departments that operate like in-house entertainment studios. They love bragging about the awards their creative has won, like their own version of the Oscars. (Real CMOs think dominating categories and driving revenue matter).

Most live for the opportunity to give celebrities millions of dollars so they can post selfies with their favorite Kardashian on their own social media. We’ve seen employees in fear that they didn’t put a like on their CEO’s Instagram or LinkedIn post fast enough. Marketing is a major line item on the P&L.

That is why we wrote the Big Brand Lie.

There are four reasons why B2B2C CEOs avoid these traps.

One: B2B2C CEOs must be more curious.

The category and business model are more complex.

Having customers and end consumers means there are many more stakeholders to understand and serve. If a B2B2C CEO is not curious about both customers and end consumers, they will lack the empathy to understand their problems. And they won’t have a clear and compelling POV to bring to the table.

Curiosity leads to empathy. Empathy leads to trust. Trust leads to success.

Two: B2B2C CEOs must share the marketing spotlight and resources.

Back in the day, when Anheuser-Busch was Pirate Eddie’s client, he asked if he could ask a dumb question: “Do we really need to buy 10 Super Bowl ad spots? Do the Clydesdale commercials really work?”

Former head of sales and CMO Keith Levy told him that more than half the spots were to motivate the 800 independent wholesale distributors. They weren’t owned or controlled by Anheuser.

They could distribute any brand of beer they wanted. They could choose to mail in a great in-store display or do a legendary job. The Super Bowl spots made the distributors proud and part of the team. The distributors were older and still had great affection for the Clydesdales, even if the younger consumer didn’t.

The ads, brands, and innovations were all a sign that Anheuser-Busch was committed to the category and to them. It was a sign that Anheuser-Busch would never stop thinking about how to make them successful. And in response, the distributors did all they could to make Anheuser successful, too.

That’s not about brand awareness. That’s demonstrating category commitment.

B2B2C CEOs are acutely aware that marketing is multi-purpose, for partner customers (B2B), end consumers (B2C) and employees. Unlike B2B CEOs, they spend money on marketing because they know it matters. And unlike B2C CEOs, they don’t let marketing go hog wild and blow up the P&L.

Three: B2B2C CEOs must have POVs that are both simple and substantial.

B2B customers lure CEOs to make things more complicated and technical, because they love to nerd out on features. B2C end consumers need things to be simple, otherwise they don’t know what choice to make. B2B2C CEOs are forced to simplify the marketing so that it is compelling enough to the customer, but concise enough to repeat to the end consumer.

Amazon Prime simplifies the choice for the end consumer, making Amazon marketplace the best place for resellers.

Google made search so easy and effective for consumers, and made the search ROI decision easy-peasy for advertisers. (Make no mistake. Google is an ad business.)

Four: B2B2C CEOs must deliver double the outcomes for partner customers and end users.

In most B2B businesses, when a customer buys, the end user doesn’t have much say. When a company buys Workday, even if the end user hates Workday, they aren’t likely to quit the company just because they use Workday.

Great B2C businesses do deliver outcomes for their end users, but not always for anyone else. Does Best Buy make a ton of money selling iPhones? Not really, but they need them to keep up with their competitors.

Remember when AT&T had iPhone exclusivity from June 2007 to early 2011? AT&T paid Apple approximately $425 per iPhone, then sold it to consumers for $199. By 2009, the Wall Street Journal reported AT&T had spent $1.3 billion just on iPhone discounts. AT&T Mobility’s operating margin dropped 50 basis points, and operating costs rose 3.8%.

Remember the magic triangle? This is how B2B2C CEOs deploy the Magic Triangle vs. their counterparts.

The Rise and Fall of Hydrafacial

First things first.

We’re going to tell you a story using all public data. We kept it to the facts, because we know we are biased. We love Pirate Clint. He’s been a long-time client and friend of Pirate Eddie. We know him personally and his track record.

We admit all of it.

And here are just the facts.

And they are undisputed.

In December 2016, a private equity firm hired Clint Carnell to be CEO of a medical aesthetics company called Edge Systems.

At the time, Edge Systems was doing about $48 million in annual revenue with $16 million in adjusted EBITDA. The company sold hydradermabrasion delivery systems to aestheticians, dermatologists, and med spas.

Pirate Clint knew the customer mix was weird.

He also saw the same pattern that was true from every hotshot plastic surgeon, famous dermatologist, and the everyday day spa.

The esthetician.

The esthetician delivered the treatment.

The esthetician was more trusted than the doctor.

The esthetician was herself the superconsumer…and she was overlooked.

Most B2B CEOs ignore the esthetician to focus on the doctor. Most B2C CEOs would walk past the esthetician to talk to the consumer.

Clint niched down on the esthetician. Made her feel seen. Educated her through continuing education programs. Gave her platforms and put her on stage at Estipalooza in Las Vegas.

He made her the center of the B2B2C strategy.

Clint rebranded the company as The HydraFacial Company in May 2017.

Here’s what happened next. This is from the 2020 Investor Deck.

Over 4 years, Pirate Clint grew…

• Revenue at a 52% CAGR from $48MM to $167MM.

• EBITDA at 38% CAGR from $16MM to $41MM.

• Installed base (B2B) 28% from 6,594 to 13,872.

• EBITDA margin ranges from 25% to 33%

What’s even more amazing was that in 2020(during COVID), revenue dropped to $119MM in revenue and 6% EBITDA. Clint stayed on as CEO. Half his management team left.

Revenue rebounded to $260MM in 2021 and EBITDA to 13%.

Q4 2021 revenue of $78 million put the company on a $312 million annual run-rate.

In December 2020, HydraFacial announced a SPAC merger with Vesper Healthcare Acquisition Corp. Enterprise value of $1.14 billion. Share price: $10. The company began trading on Nasdaq under the ticker SKIN.

The stock hit $29.49 on November 2, 2021. That’s 175% appreciation from the SPAC price in under a year.

On November 9, 2021, HydraFacial announced Clint Carnell’s departure as CEO and from the Board of Directors. The stock was at $28.64 the day before the announcement.

That is a story for another time. Here’s what happened after.

Post Pirate Clint, revenue did go up.

But in Clint’s last quarter, ARR was already $321 million dollars.

The second CEO largely inherited the strong tailwind and B2B2C momentum. The next three CEOs all inherited the massive $900 million dollar cash balance war chest Clint raised in the PIPE (Private Investment in Public Equity) and secondary debt.

Today, the cash balance is $232 million dollars for a business that is in decline, and 97% of market capitalization has evaporated.

How did that happen?

CEO #2 came from Coty, a B2C beauty conglomerate.

He came straight from running Kylie Cosmetics and KKW Beauty at Coty. Coty paid $600 million for 51% of Kylie Cosmetics (valuing it at $1.2 billion) and $200 million for 20% of Kim Kardashian’s KKW Beauty.

The math didn’t check out.

By March 2025, Coty dumped its Kardashian stake entirely, and Forbes had already blown up the Kylie revenue numbers, tanking Coty stock 13%.

CEO #2 elevated celebrities at the expense of the esthetician.

He launched the JLo Beauty Booster partnership within months of arriving (May 2022). This was the classic celebrity-licensing playbook: borrow someone else’s fame, slap it on a product, and hope the halo effect does the work.

This can work in the short term. BUT If the celebrity is not tied to a new category design, this move fails. Every time. Logan Paul’s energy drink Prime, had a huge launch. Big success. Now profits are down 92%.

This is the opposite of what Clint built.

Clint’s entire thesis was that the estheticians were the core of the business. And the marketing engine. Clint was creating demand through a committed community. CEO #2 was renting temporary attention with a celebrity.

In CEO #2’s first year, selling and marketing expenses spiked to 44% of revenue, up from 37% under Clint. That’s what a B2C influencer strategy looks like on a P&L. The company was burning cash on celebrity partnerships, brand campaigns, and consumer-facing marketing that bypassed their providers entirely.

Then the floor fell out.

In March 2022, HydraFacial launched Syndeo, a new digitally connected delivery system. It had frequent treatment interruptions and quality issues.

Estheticians lost enthusiasm. Churn increased. New system sales cratered. In 2023, the company took a $20 million inventory write-down. Gross margins collapsed to 39%.

Nearly half of what they’d been four years earlier.

A B2B CEO would have likely caught the quality issue before launch.

Under Clint, G&A was 16% with one VP of marketing. Post Clint, G&A ballooned to 33% with four VPs of marketing, per LinkedIn.

In June 2023, the stock was dropped from the Russell 3000 index. By September, it was trading at $1.90. In November 2023, CEO #2 resigned.

CEO #3 arrived in March 2024 with another B2C background. Co-founder of Bluemercury, a direct-to-consumer beauty brand acquired by Macy’s.

FY2024: Revenue fell to $334 million. Gross margins recovered somewhat to 55%. But here’s the number that should haunt every B2B2C executive reading this: G&A hit 38% of revenue. S&M was 35%.

General and administrative expenses exceeded selling and marketing expenses. The bureaucracy overtook the marketing. EBITDA margin: 3.7%.

In September 2025, CEO #3 departed.

CEO #4 arrived in October 2025. This time, the board went the other direction: a B2B background from Abbott, a medical device company.

The income statement for FY2025 shows the continued trajectory: S&M dropped further to 31% of revenue, and G&A climbed again to 39%. The gap between bureaucracy and marketing widened to 8 percentage points. In dollar terms, the company spent $117.9 million on G&A and $93.6 million on S&M. Twenty-four million dollars more on overhead than on reaching customers.

Gross margins recovered to 65%, and EBITDA improved to 15%, but revenue kept declining to $300.8 million. The 2026 guidance: $285 to $305 million.

But the stamp of the B2B CEO was most deeply felt when the company just rebranded.

Bye bye consumer. Bye bye esthetician. The stock went down 8%

The stock trades under $0.90 as of April 23, 2026. Market cap: just over $100 million.

Combined S&M and G&A went from 53% of revenue under Clint to 73% under CEO #2. Twenty points of margin destruction. And it never came back.

Even as the strategy was abandoned and gross margins recovered, the overhead stayed. That is the permanent scar tissue of a B2C pivot in a B2B2C business. You can change the strategy. You cannot unwind the cost structure.

This is an even worse visualization from an investor’s POV.

A Customer’s Reaction to CEO Carousel

Pirate Alexis is the owner and landlord of Best Ever Skin in Clarendon Hills, Illinois.

When Pirate Eddie first met here in 2023, she had one facial device and a quarter of a million dollars in revenue.

Three years later, she has three facial devices and triple the revenue. Plus four treatment rooms and five team members. She bought the building she works in. All of this was bootstrapped by herself.

She’s the very definition of the American Dream.

The sad part for Hydrafacial is that they only have one of her three facial systems. Why does the Category King only have one-third of the market share of a customer that has had massive success?

They forgot to dance with the one who brought them.

If HydraFacial had done its job, if they had remained the provider-first B2B2C company that helped aestheticians like Alexis build their businesses, she should have had three HydraFacial devices in four treatment rooms. Instead, competitors filled the gap.

This is what abandoning your Supers looks like at the provider level. Alexis is not an edge case. She is the median outcome. Multiply her story by thousands of aestheticians making the same calculation, and you begin to understand where HydraFacial’s revenue went. Not to a competitor’s superior product. To a competitor’s superior relationship.

7 Steps to Become a Legendary B2B2C CEO

Good news, Pirates! We’re going to share how a B2B or B2C CEO can build a B2B2C strategy.

One: Admit you have a knowledge gap

Read more

Arrrrr! 🏴‍☠️ Welcome to a 🔒 founders-only edition 🔒 of Category Pirates. Each week, we share radically different ideas to help you design new and different categories. Founding subscribers can access the entire archive of 200+ mini-books and audiobooks. If you’re not a paid subscriber, hop aboard!

Subscribe now

Dear Friend, Subscriber, and Category Pirate,

So. About that job of yours.

The one you got hired for. The one you got promoted for. The one that, somewhere between the last offsite and the next one, quietly became a job nobody’s actually paying for anymore.

You probably felt it before you could name it. A Monday morning where the thing you’re best at feels weirdly less valuable than it used to. A meeting where someone under 30 mentions an AI Agent and everyone nods like they understood. A LinkedIn post from a peer announcing they’ve “transitioned into a new chapter” (translation: got laid off and is now a fractional something).

This is a category shift.

CFOs are watching their role morph from scorekeeper to category architect. Marketers are watching the cost center they’ve defended for decades get reframed as the highest-leverage profit engine in the company. Knowledge workers are watching the premium on “knowing things” collapse while they’re still mid-sentence explaining what they know. And careers, the supposedly linear thing your parents told you to build, are turning into a series of ruptures that either break people or remake them.

The old way was to work harder at the job you were given.

The new way is to redesign the job itself.

These 7 audiobooks are a field guide for the second move.

Listen in order or pick your rupture

You can go straight through the list, or jump to the audiobook that matches the function getting rewritten underneath you right now. Either works. What doesn’t work is pretending the rewrite isn’t happening.

Careers used to be ladders. They aren’t anymore.

This audiobook reframes the modern career as a series of Career Quakes. The layoff that reroutes you. The market shift that invalidates your specialty. The quiet realization that the role you trained for isn’t coming back. Most people treat these as failures. Creator Capitalists. treat them as the raw material for becoming irreplaceable.

You’ll learn why the people who come out stronger aren’t the ones who avoided the quake, they’re the ones who used it to design a new category of work only they can occupy.

If the ground has moved under you in the last 18 months, start here.

Peter Drucker named the knowledge worker in 1959. AI is un-naming them in 2026.

This audiobook doesn’t mourn the knowledge worker. It buries them and hands you the blueprint for what comes next. The 6-step shift moves you from selling hours, to selling outcomes, to selling outcomes AI can’t replicate: judgment, taste, POV, and category authority.

The uncomfortable part is that “being really good at your job” is no longer a moat. The freeing part is that you don’t need permission to build a new one.

If you bill for time, this audiobook will make you deeply uncomfortable. That’s the point.

The CFO role is getting split in half.

On one side: the Agentic CFOs who use AI Agents to run reporting, close the books, and monitor cash in minutes instead of weeks, freeing them to design the future of the business. On the other side: the CFOs still doing the work the agents now do, wondering why their influence is shrinking.

This audiobook introduces the Friedman Matrix and shows how the best CFOs are moving from scorekeeper to category designer. They’re in the arena shaping the P&L, not reporting on it.

If you’re a CFO, a founder working with one, or anyone who thinks finance is a back-office function, this one rewires the org chart in your head.

Tesla spends roughly zero dollars on traditional advertising.

And yet every Hertz rental counter that hands out a Model 3 is a multi-million-dollar marketing asset Tesla didn’t pay for. That’s not a coincidence. That’s category design.

Part 1 of this series opens with the Tesla case study and uses it to introduce a radical idea: marketing, done right, isn’t a cost. It’s a profit-positive engine that uses adjacent categories (like rental cars) to build demand for the primary one (like buying a Tesla).

If the word “marketing” makes your CFO flinch, this audiobook is the antidote.

Here’s the ugly truth most CMOs already know but can’t say out loud.

The reason marketing gets cut first in a downturn is because marketing teams agreed, at some point, to be measured as a cost. Once you accept cost-center framing, you’ve already lost the budget fight. Every quarter. Forever.

Part 2 makes the case for why that framing has to die, names the executives who keep it alive (usually accidentally), and lays out what marketing looks like when it’s structured as the growth engine instead of the expense line.

This is the audiobook to send to your CFO before the next budget cycle.

Parts 1 and 2 diagnose the problem. Part 3 is the prescription.

Five concrete steps for marketers who want to stop defending their budget and start owning the P&L. It covers how to restructure your team around profit contribution, how to price your output like an asset instead of a line item, and how to use Category Design to build marketing programs that generate revenue on their own.

If you’re a CMO trying to survive the next earnings call, or a founder trying to figure out whether your marketing leader is playing offense or defense, start with Parts 1 and 2, then run through Part 3 with your team.

Every audiobook above names a role getting rewritten.

Lightning Strike Legends shows you what happens when two people decide to rewrite theirs at the same time.

This audiobook is the behind-the-scenes story of a single Lightning Strike that produced a 4x ROI in three weeks. It’s tactical, specific, and refreshingly unromantic about how category momentum actually gets built. No vague “go viral” advice. Real choreography: what was launched, when, by whom, and why it worked.

It’s also the audiobook to listen to last, because it answers the question all six previous audiobooks raise. Which is: if the job is getting rewritten, what do I actually do on Monday?

Lightning Strike Legends is one answer. Not the only answer. But it’s proof the answer exists.

The job you were hired to do is not the job the market is now paying for.

That’s the throughline running through all seven of these audiobooks, which is why we dropped them in the same batch instead of spacing them over six months. The rewrite is happening now. The Category Designers who see it first get to design the new role. Everyone else gets assigned to one.

So. Press play. Take the walk. Let the headphones do what meetings can’t.

And when you hear the audiobook that names the thing you’ve been feeling but couldn’t quite say out loud, don’t be surprised. That’s sort of the whole point.

Arrrrrrr,

Category Pirates

Eddie Yoon

Christopher Lochhead

P.S. - Audiobooks show you the rupture. The Academy is where you learn to design what comes after it.

If any of these audiobooks land, there’s a real next step sitting right in front of you.

Category Design Academy Cohort 4.0 applications close this Sunday, April 27. The cohort starts May 4.

The Academy is where pirates go to stop reacting to category shifts and start designing them. It’s where the CFO in your head becomes the Agentic CFO. Where the marketer in your org chart becomes the profit center. Where the knowledge worker clocking hours becomes the category authority who gets paid for outcomes.

Listening is the diagnosis. The Academy is the prescription.

👉 Apply before Sunday here.

Arrrrr! 🏴‍☠️ Welcome to a 🔒 founders-only edition 🔒 of Category Pirates. Each week, we share radically different ideas to help you design new and different categories. Founding subscribers can access the entire archive of 200+ mini-books and audiobooks. If you’re not a paid subscriber, hop aboard!

Subscribe now

Read more

Arrrrr! 🏴‍☠️ Welcome to a 🔒 founders-only edition 🔒 of Category Pirates. Each week, we share radically different ideas to help you design new and different categories. Founding subscribers can access the entire archive of 200+ mini-books and audiobooks. If you’re not a paid subscriber, hop aboard!

Subscribe now

Read more

Arrrrr! 🏴‍☠️ Welcome to a 🔒 founders-only edition 🔒 of Category Pirates. Each week, we share radically different ideas to help you design new and different categories. Founding subscribers can access the entire archive of 200+ mini-books and audiobooks. If you’re not a paid subscriber, hop aboard!

Subscribe now

Read more

Arrrrr! 🏴‍☠️ Welcome to a 🔒 founders-only edition 🔒 of Category Pirates. Each week, we share radically different ideas to help you design new and different categories. Founding subscribers can access the entire archive of 200+ mini-books and audiobooks. If you’re not a paid subscriber, hop aboard!

Subscribe now

Read more

Arrrrr! 🏴‍☠️ Welcome to a 🔒 founders-only edition 🔒 of Category Pirates. Each week, we share radically different ideas to help you design new and different categories. Founding subscribers can access the entire archive of 200+ mini-books and audiobooks. If you’re not a paid subscriber, hop aboard!

Subscribe now

Read more

Arrrrr! 🏴‍☠️ Welcome to a 🔒 founders-only edition 🔒 of Category Pirates. Each week, we share radically different ideas to help you design new and different categories. Founding subscribers can access the entire archive of 200+ mini-books and audiobooks. If you’re not a paid subscriber, hop aboard!

Subscribe now

Read more

Arrrrr! 🏴‍☠️ Welcome to a 🔒 founders-only edition 🔒 of Category Pirates. Each week, we share radically different ideas to help you design new and different categories. Founding subscribers can access the entire archive of 200+ mini-books and audiobooks. If you’re not a paid subscriber, hop aboard!

Subscribe now

Read more

Arrrrr! 🏴‍☠️ Welcome to a 🔒 founders-only edition 🔒 of Category Pirates. Each week, we share radically different ideas to help you design new and different categories. Founding subscribers can access the entire archive of 200+ mini-books and audiobooks. If you’re not a paid subscriber, hop aboard!

Subscribe now

Read more

Subscribe now

Dear Friend, Subscriber, and Category Pirate,

Dr. Eric Hanson knows how to get the Pentagon to write a check. He has done it, to the tune of more than $300 million, for other people’s companies.

Seventeen years as an Air Force physician and senior flight surgeon. 750 hours in 36 aircraft. Dual board certified in aerospace and preventative medicine. Call sign “Genes”. (Which tracks, because he also has an MPH in epidemiology with a genetics concentration from Johns Hopkins on top of his MD.)

He ran a 15 million dollar DARPA-funded bioterrorism surveillance project in Washington, D.C., right after the anthrax attacks. He became the Air Force chair of the Congressionally Directed Medical Research Program, a 1.27 billion dollar program in fiscal year 26. He’s founded five companies. Published five books, 25 articles, and holds nine patents.

And somewhere in there he decided he wasn’t done serving.

So he started MilMed Connect, a Techstars portfolio company, to do one thing most founders don’t even know is possible:

Help life science CEOs raise money from the U.S. government without giving up a single point of equity.

Over 300 million dollars of it, to date.

The Pentagon deploys more than $40 billion a year in research funding. The Congressionally Directed Medical Research Program alone is $1.27 billion. That’s a bigger annual deployment than most VC funds have under management. And it doesn’t cost you equity.

The Department of Defense doesn’t want your cap table. It wants dual-use technology, products that work in both civilian and military settings. Smaller. Lighter. Cheaper. Lower-power. AI-assisted.

The military calls it C-SWaP: Cost, Size, Weight, and Power.

One of Eric’s clients, a biotech CEO working on host-targeted antivirals, raised $50M in private capital and $60M in non-dilutive DoD funding. One started at $11M and bumped to $24M, then $36M, then $50M without having to recompete. The Navy awarded one of Eric’s dental AI contracts in exactly 90 days from pencil-to-paper.

Try getting a VC to move that fast.

The military is the greatest Superconsumer on Earth.

If you’ve read our work, you know what a superconsumer is: the highest-intensity user in a category, the one whose demands pull the entire product forward.

Superconsumers force innovation. They don’t settle for average. They pay a premium for the extreme version.

The U.S. military might be the ultimate one.

It needs devices that function in the Arctic and the Sahara. It needs batteries that last in theater. It needs medical countermeasures for chemical, biological, radiological, and nuclear threats. It needs prolonged casualty care solutions for war fighters who, as Eric explains in harrowing detail, sometimes have to wait 72 hours or more near the point of injury before they can be evacuated.

And when the military finds a solution that works, it writes a check.

What Eric has done is category design a business around the translation layer. He’s built a firm, a Techstars accelerator arm, and a software product called Navigator, effectively an operating system for dual-use CEOs. He’s trained 50 military medical veterans to work with industry. 25 have started their own companies. He’s got a Curly Bot, a Dr. Eric Bot, and a dual-use triage bot in development.

He named the problem. He framed the problem. He’s claiming the problem.

That’s what a Creator Capitalist looks like in uniform.

The four capitals, fully loaded.

One of the things we love about Eric’s story is that he is running the full Creator Capitalist playbook, whether he planned it that way or not.

Financial capital. Non-dilutive government funding, deployed to founders who would otherwise be stuck on the VC treadmill.

Reputation capital. 17 years in the Air Force, an affiliate professorship at OHSU, a seat as a Uniformed Services University military medical ambassador. The kind of credibility that opens doors inside the Pentagon that nobody else can even knock on.

Relationship capital. A network of 50 trained military medical vets, each with their own networks. DoD program officers he’s worked with for over a decade. CEOs he’s placed inside the most exclusive buying room in the world.

Intellectual capital. The Navigator product. The dual-use triage framework. The C-SWaP lens applied to civilian tech. The books, the patents, the IP.

The reason we wanted Eric on the show isn’t because every listener is going to start raising non-dilutive DoD funding tomorrow.

It’s because Eric is a walking proof point that the Creator Capitalist playbook works in the most bureaucratic, credentialed, gate-kept industry on Earth.

If it works inside the Pentagon, it works in legal tech. It works in real estate. It works in consumer health. It works in whatever industry you’ve been told is “too traditional” or “too regulated” or “too old school” to do something new in.

The playbook doesn’t care about your industry. It cares whether you’re willing to name, frame, and claim a category before anyone else does.

Here’s how to navigate this conversation:

• 02:14 – Jack Ryan meets Michael Crichton: Why Eric’s resume reads like a thriller and how the Uniformed Services University path got him through med school without a dime of debt.

• 04:59 – Medical countermeasures, explained: What “dual-use” actually means when the threats are chemical, biological, radiological, and nuclear and why COVID blew the doors off Eric’s 5-client model overnight.

• 09:45 – The cap table that isn’t: How a founder raised $50M private and $60M non-dilutive and what the government wants in return that isn’t equity.

• 13:59 – C-SWaP and the super consumer: Eddie’s hearing-aid story and why the military is the most demanding product development partner a founder could ever ask for.

• 18:30 – The 1-in-10 CEO: 1,500 companies evaluated, 300 worked with directly and the one trait that predicts who actually gets funded.

• 23:00 – $40 billion a year: The DoD funding landscape, the Small Business Innovation Research program, and how it stacks up against NIH, Andreessen Horowitz, and every VC fund you’ve heard of.

• 26:27 – DoD vs. VC, side by side: A 90-day Navy contract, million-dollar awards, and what happens when a government program officer is more founder-friendly than your Series A board member.

• 35:45 – Navigator: The operating system Eric is building for dual-use CEOs and the Curly Bot naming moment you’ll have to hear to believe.

• 40:04 – Ukraine as the accidental R&D lab: Why prolonged casualty care changed everything about military medicine and why nothing has been the same since.

• 46:30 – For the 18-year-old considering med school: The advice Eric would give his own kid, including a year in Korea, six months in Hungary, and a week on a paddle wheeler in Brazil studying parasites.

• 49:34 – What the Academy actually did for him: Eric on his Category Design journey from Substack subscriber to Cohort 3.0 graduate to reading the Creator Capitalist book with both of his sons.

To connect with Dr. Eric:

• Follow Dr. Eric on LinkedIn

• Email: eric@milmedconnect.com

Arrrrrr,

Category Pirates 🏴‍☠️

Eddie Yoon

Christopher Lochhead

P.S. — Eric didn’t become a category of one by accident.

He took 17 years of military medical expertise, named the translation gap nobody else was solving for dual-use CEOs, and built an entire category around it. Bots, software, a Techstars accelerator, a trained army of veteran entrepreneurs.

He’s also a Category Design Academy Cohort 3.0 graduate. Which means the frameworks he’s using to scale Navigator and train the next generation of military medical Creator Capitalists are the same ones we teach inside the Academy.

Academy 4.0 applications close in 10 days. The next cohort starts in May.

If Eric’s story resonates, if you’re sitting on a superpower the rest of the world hasn’t named yet, that’s exactly the work the Academy is designed to do.

→ [Learn more about the Academy here.]

→ [Apply here.]

Arrrrr! 🏴‍☠️ Welcome to the Pirate Street Journal, a free weekly read on category design, markets, and what it means to think different. For more: Audiobooks | Creator Capitalist podcast | Books | Sign up for a Founding subscription to ask the Pirate Eddie Bot your category design questions.

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Dear Friend, Subscriber, and Category Pirate,

When the market breaks, category designers get to work

Pirate Eddie was on Schwab Network last Friday.

The data he walked through wasn’t encouraging.

Disposable personal income down 1% in February. Personal consumption expenditures up 5%. GDP at 0.5% last quarter, down from 4.4% the quarter before. Michigan consumer sentiment is sitting at 47.6%, down 11%.

Consumers are spending more than they have and feeling worse while they do it.

Is that bad news for you?

Only if you’re playing the old game.

Smart money is already moving.

While most companies are playing defense, smart money is making directional bets on what comes next.

Costco is building gas-only stations for the first time in company history. A 40-pump station is already open in Mission Viejo. A 240-pump station is planned for Honolulu in 2027. That is a CapEx commitment that says: we believe high gas prices and inflation are the new operating environment.

Anheuser-Busch just bought 85% of Beatbox Beverages for half a billion dollars.

Why? Because while wine is down 7.7%, spirits are down 4%, and beer is down 4%, Beatbox did $340 million in retail last year at 50% year-over-year growth. Sweet and spicy cheladas. Off-premise occasions. Music culture identity. A container designed for how younger consumers actually want to drink.

Beatbox didn’t beat the beer category. It created a new category.

And Anheuser recognized what was happening before it was obvious.

Down markets don’t shrink categories. They sort them.

When consumer spending contracts, it doesn’t contract equally. Nice-to-have dollars shrink. But they don’t disappear. They get redirected.

Consumers stop spending on things they’ve already done. Things they’re bored of. Things that feel like more of the same.

They choose different.

And that is not a headwind for a category designer.

When people stop spending automatically and start choosing deliberately, the question becomes: what are they choosing between? Who named the problem they didn’t know they had? Who framed the decision before anyone else thought to?

That’s your job.

The companies bleeding right now optimized for execution inside someone else’s map. The ones gaining ground built their own.

Beatbox didn’t ask how to win in beer. Costco didn’t ask how to compete on gas price. They asked: what category could we design that doesn’t exist yet where we will win?

That is exactly the question this market is demanding right now.

There is no better time to build a new category

A down market feels like bad news. But for category designers, contraction is signal. It tells you precisely where the old map stopped working and where the new one needs to be drawn.

When consumers choose different, they need new language to describe what they’re choosing. They need someone to name the problem. They need a category that didn’t exist before.

Category designers don’t just do well when markets contract. They stop being at the mercy of market cycles altogether.

When you own a category, you’re not competing inside someone else’s shrinking market. You set the price. You define the problem. You decide what winning looks like.

The economy shifts around you, not beneath you.

That’s how your life’s work compounds.

If that framing resonates, there are two ways to go deeper.

1. The Category Design Academy’s next cohort begins May 4. Applications close April 27. This is where people who’ve been most right about something for the longest time finally get the language, the frameworks, and the structure to build around it. Apply here.

2. If you want a thinking partner that will push back on your category thesis and help you name the problem no one else is naming, The Pirate Eddie Bot is built for that. It’s the only AI trained on category design and Creator Capitalist, and it comes with a Founding membership. Become a Founding Subscriber here.

Arrrrrrr,

Category Pirates 🏴‍☠️

Eddie Yoon

Christopher Lochhead

P.S. — Your superconsumers are also sorting their categories. Including yours.

The question is whether you’re building the category they’re choosing next.

New markets don’t just need new products. They need new language. The companies that win in a down market are always the ones who named what was happening before anyone else had words for it. Beatbox didn’t just make a different drink. They named a different occasion. Costco isn’t just selling gas. They’re naming a new kind of membership value.

And it starts with language.

The Academy is where that language gets built. Not handed to you, but excavated from what you already know, sharpened by a room of people working on real things, and stress-tested until it holds.

The books give you the model. The Academy gives you the room to build with it.

If you’re ready to name the category this market is creating space for, applications close April 27. [Apply here →]

Not ready for the Academy? The Pirate Eddie Bot is the only AI trained on Category Design and Creator Capitalism, and it’s included with a Founding membership. [Start here →]

Arrrrr! 🏴‍☠️ Welcome to a 🔒 subscriber-only edition 🔒 of Category Pirates. Each week, we share radically different ideas to help you design new and different categories. For more: Audiobooks | Category design podcast | Books | Sign up for a Founding subscription to ask the Pirate Eddie Bot your category design questions.

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Dear Friend, Subscriber, and Category Pirate,

In Career Quakes Part 1, we wrote about 21 distinct global, organizational, and personal quakes and 7 core truths about quakes. We shared Pirate Shelly’s story as an example of how to build a personal AI intelligence officer to navigate the quakes in your lives.

Never let a crisis go to waste.

In this mini-book, let’s go deep into the practical and tactical about how to turn a Career Quake into Quake Capital. Turmoil into treasure.

The Treasure is in the Turmoil

Pirate Christopher went through a ton of turmoil as a teenager.

His band was signed when he was 14. 3 years later, he thought his band was on fire.

Then the quakes started.

Drummers quitting. Bass players quitting. Getting screwed by bar owners.

And the band was running out of money.

One quake led to another.

As the band was going bust, Pirate Christopher was getting thrown out of school. No one realized he was dyslexic. They told him he was dumb.

His mother’s voice on his shoulder, “You don’t get to grow up to be a bum.”

She was a 5’3” single mum. Pirate Christopher towered over at the age of 12. There were only two things to get her message across.

Guilt and love.

So she used a lot of both.

Those feelings drove Pirate Christopher. His entire life comes down to aiming to not experience the horror of disappointing his mother, father, and his grandfather.

He chose to strive to become the man they told him he could be.

Pirate Christopher’s mother taught him.

When somebody says, “I’m really disappointed in you,” what they’re saying is, I love you, and the potential I see for you is so much greater than the way you’re conducting your life right now. The delta between who you are and who you could be is crushing me.

We are only disappointed to the degree to which we see potential unrealized.

This is true for entrepreneurs, category designers, and creator capitalists of all types.

When we see the potential for a different future and the gap between what exists and what’s possible, it drives us to act.

It drives us nuts. And when a young person we care about doesn’t exploit their opportunities, it breaks our hearts.

Pirate Christopher isn’t the only person to find treasure in the turmoil. Fueled by love and guilt.

What Drives Career Breakthroughs?

We recently completed the “Creator Capitalist Mt. Rushmore Analysis”.

It’s a deep dive into what drives people to make a career change, which drives meaningful economic outcomes across hundreds of careers.

We mapped the demand landscape across two dimensions: the type of situation that triggered the value creation and the type of outcome that was achieved.

What we found was startling.

Most people think career breakthroughs happen when everything goes right.

They don’t.

Two cells in the entire demand matrix accounted for 78% of all economic value created.

Not 78% spread across a dozen categories. Two cells. Out of dozens of possible intersections.

Lifequakes × Turnarounds = 47% of all value:

Crisis meets pivot, meets enterprise value creation. Nearly half of all economic value came from people and/or organizations that experienced a lifequake, used it to execute a turnaround, and built something transformative on the other side.

A disproportionate amount of celebration goes towards the entrepreneur going up in the world. Many acts of entrepreneurship are really acts of desperation. A way out, not a way up.

What forces the person is a quake. They realize, “My life is going to suck if things don’t get different.”

Or said a different way:

The risk of staying the same is greater than the change.

Reframe × Strategy/M&A = 31% of all value.

Bringing a new lens to an old problem opens up a world of possibilities for new strategies or M&A.

A reframe means someone looked at a familiar asset, market, or situation and saw something completely different from what everyone else did. That new lens is almost always built from one of the Four Capitals: financial, intellectual, relationship, or reputation.

The examples below show what happens when that shift in perspective gets applied to a major strategic move.

Financial Capital: Warren Buffett buys an infinite treasure chest for M&A

Buffett didn’t buy insurance companies; he bought a machine that paid him to borrow money forever for free.

Everyone else saw insurance as a premium-and-claims business. Buffett saw the float: the cash sitting between when premiums are collected and when claims are paid out. He got to invest it interest-free for decades. He bought National Indemnity in 1967 for $8.6 million, and nobody understood why. Then he bought GEICO. Then General Re.

“This collect-now, pay-later model leaves us holding large sums we call float. Meanwhile, we get to invest this float for Berkshire’s benefit. We enjoy the use of free money and, better yet, get paid for holding it.” Warren Buffett

The float grew from $16 million in 1967 to $164 billion by 2022. An 8,000-fold increase. He used it to buy BNSF Railway, See’s Candies, and dozens of others. No outside capital.

For many companies, their WACC (weighted average cost of capital) is anywhere from 5% to 15%. Capital carries a cost that companies must pay.

Buffett’s wacky source of capital gave him a negative WACC to take unlimited whacks at buying and investing in everything from AmEx to Apple.

Intellectual Capital: Roche acquires Genentech

Every other pharma company that bought a biotech did the same thing. They did the deal, absorbed the team, installed their processes, and watched the innovation die.

Roche bought a 56% stake early and left Genentech completely alone. Didn’t touch the culture. Didn’t touch the scientists. Let it run independently for years. Then paid $47 billion for the rest in 2009.

What came out of that engine: Herceptin, Avastin, Rituxan. Three of the best-selling cancer drugs in history.

You can’t acquire innovation by controlling it. Roche bought the goose and kept it safe.

Relationship Capital: InBev acquires Anheuser-Busch

InBev wasn’t just buying brands like Bud Light. They were buying a century of relationships with American beer distributors.

The U.S. beer distribution system is a legally protected three-tier network. Those distributor relationships are built over generations, governed by state franchise laws that make them nearly impossible to terminate. No new entrant can replicate them. No amount of money builds them from scratch. InBev knew this. They paid $52 billion in 2008 not for the brands, but for the pipes.

Within two years, they cut $2.25 billion in costs. AB InBev today controls roughly 25% of global beer volume.

The distributor network is the business. The brands were a bonus.

Reputation Capital: Microsoft acquires GitHub

One developer’s reaction to the day the deal was announced said it all: “Microsoft buying GitHub feels like Exxon Mobil buying Greenpeace.”

That reaction was the whole point. For two decades, Microsoft was the villain of the developer world. They were closed source and anti-Linux. Ballmer had literally called Linux a cancer. GitHub had 28 million developers, and the one thing Microsoft couldn’t build or fake: trust. Nadella paid $7.5 billion and said the quiet part out loud: “We’ll have to earn the trust, there’s no question of that.”

“Overnight, Microsoft now has a relationship with almost every developer in the world,” John Connors, Microsoft CFO

GitHub had $300 million in revenue at acquisition. By 2024, it had hit $2 billion. Nadella on a 2024 earnings call: “GitHub Copilot is already a larger business than all of GitHub was when we acquired it.”

Copilot didn’t exist when Microsoft bought GitHub. It was built on the reputation capital they acquired, and then earned the right to use.

They weren’t buying a code repository. They were restoring their reputation.

Almost a third of all value came from people who saw the world differently and used that new perspective to execute a major strategic move.

Read that again. The single biggest driver of economic value creation is lifequakes combined with turnarounds. They’re called pivots.

Not smooth growth. Not incremental innovation. Not optimization. Crisis. Disruption. The thing everyone runs from.

This isn’t philosophy. It’s math. And the math says: the red ring is where nearly half of the value is created.

Every instinct tells you to avoid the quake.

The data says use it.

Because the people in this data didn’t just recover from their quakes. They came out the other side with a POV nobody else had, because nobody else lived through what they did.

That’s the raw material for a new category.

The 4 Piratey P’s

When a career quake hits, you need a playbook. A powerful lens. Not a 47-step strategic plan. Not a meditation app.

A simple, honest, actionable framework that respects the reality of what you’re going through while giving you something (concrete) to do about it.

We call it the 4 P’s:

• Puke

• Plant

• Prioritize

• Progress

Pirate Eddie and his family have deep firsthand experience.

In June 2017, Pirate Eddie left his old firm to go solo and started off with a bang.

He gave a keynote speech at a conference in Anaheim alongside Arnold Schwarzenegger, Giada De Laurentis, and Earvin Magic Johnson.

His consulting income doubled, while working a fraction of the hours he used to. He was writing freely at HBR.

The organizational Ring was all green. In a way he had never felt before. His career was driving with incredible momentum, and Pirate Eddie was enjoying the wind in his hair. He had dreamed about this moment for years.

Then a personal quake t-bones his family.

One of his kids went through a major mental health crisis in junior high. She was struggling with depression and anxiety. Eventually, they had to hospitalize her for her safety.

When Pirate Eddie’s wife took their daughter into the hospital in the middle of the night, she had to call a friend to stay with the other kids.

Because Pirate Eddie was traveling for work.

Pirate Eddie had the most agency and freedom he ever had in his work.

But he wasn’t there when his family most needed him.

Today, his daughter is in a much healthier place. She’s put in a ton of work with counselors. She has great coping skills.

She’s emotionally healthier and more mature than most adults.

When Pirate Eddie loses his temper, she will calmly call him out with courage and care. Pirate Eddie and his wife are proud of the progress she has made. She is using her scars to serve and help other people.

But Pirate Eddie is still counting the cost of how he reacted to the personal quake.

He created a ton of freedom in his work, but work was so addictively fun that he didn’t always make the right choices in the moment.

He focused on his career and lost sight of his wife’s. Pirate Eddie’s wife was making a comeback in her nursing career when all of this went down. She yet again had to sacrifice her career.

Pirate Eddie was too blind, busy, and not empathetic enough to appreciate her sacrifice.

It took years and thousands of dollars of marriage counseling to hash all of this out.

The counseling was necessary because there were feelings Pirate Eddie was reluctant to puke out. Because he was ashamed that he wasn’t there when his family needed him. He was ashamed that he cared so much about how this impacted his work. He was ashamed that he couldn’t see the sacrifices his wife was making.

If you don’t puke out your feelings, you can’t process them.

P1: Puke

Get it out of your system.

When a quake hits, the first thing you need to do is puke.

Don’t ignore it. Don’t clean it up. Don’t look on the bright side of puke.

Look at the puke in all its disgusting, smelly and revolting mess for what it is.

Puke is pure data.

Just got laid off? You’re furious, terrified, humiliated, relieved, excited? Good. Feel that. Say it out loud. Write it down. Call someone you trust and vent until you’re empty. Journal like your life depends on it, because it might.

Every career decision you make while you’re full of fear, rage, excitement, or despair will be a bad one.

The goal of the puke phase is to drain the emotional poison so you can think clearly.

The mistake most people make isn’t feeling their feelings. It’s skipping this step entirely—pretending they’re fine, jumping straight into “what’s next,” and making reactive decisions from unprocessed panic.

Or they get stuck in the puke and never move on.

Puke.

Get it out.

And stop puking.

If you’ve read A Pirate’s Guide to AI, you already know what comes next: puke it into the AI.

By the way, the Pirate Eddie bot is a pretty good listener. And it doesn’t fall asleep early like the real Pirate Eddie.

P2: Plant

Use it like fertilizer.

Read more