Category Pirates

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.Don’t take our word for 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.If you’ve been on the fence for a while, this is the week.Arrrrrrr,Category Pirates 🏴‍☠️Eddie YoonChristopher Lochhead This is a public episode. If you'd like to discuss this with other subscribers or get access to bonus episodes, visit www.categorypirates.news/subscribe

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 b******t 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: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.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.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 LinkedInFollow Pirate Alexis Skigen Rago on LinkedInFollow Pirate Melissa Andrews on LinkedInFollow Pirate Jennifer Hall Thornton on LinkedInFollow Pirate Mary Kathryn Johnson on LinkedInArrrrrr,Category Pirates 🏴‍☠️Eddie YoonChristopher LochheadP.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. This is a public episode. If you'd like to discuss this with other subscribers or get access to bonus episodes, visit www.categorypirates.news/subscribe

This is a public episode. If you'd like to discuss this with other subscribers or get access to bonus episodes, visit www.categorypirates.news/subscribeNearly half of all economic value is created by the people everyone else feels sorry for.We ran the numbers. Two cells on the entire demand matrix account for 78% of all economic value created across hundreds of careers. Not twelve cells. Two.The biggest one? Lifequakes crossed with turnarounds. 47%.Translation: nearly half the wealth, reputation, and category-defining work in the world comes from people in the middle of the thing everyone spends their life running from.The conventional career advice is to avoid disruption, minimize risk, and find the safest landing spot. The data says that advice is how you stay average. The quake isn’t the detour from your category. It is your category.This audiobook is the playbook. Four P’s. Six AI prompts. Three military stories that will rearrange how you think about your own turmoil.Here’s what you’ll get inside:[00:02:00] – Where Real Career Breakthroughs Actually Come From: 78% of economic value is concentrated in two cells of the demand matrix. We walk you through the math and the moment a person realizes that staying the same is riskier than changing. That’s the ignition point for every pivot that ever mattered.[00:10:00] – The 4 P’s. Not Another 47-Step Plan: Puke. Plant. Prioritize. Progress. A framework you can actually run when the ground is moving. Pirate Eddie uses his own personal quake (the one he handled badly) to show you why the first step is the one most people skip.[00:18:00] – Which of the Four Capitals Has the Greatest Upside Right Now: Every quake rebalances your Financial, Relationship, Reputation, and Intellectual Capital. The mistake is trying to rebuild all four. The move is making a deliberate bet on the one the quake just handed you for free.[00:26:00] – Why Military Veterans Are Walking Category Design Case Studies: Three stories at three stages. Dr. Eric Hanson pitched 36 times before someone said yes. Robby Cronstedt is standing at the edge of the cliff right now. Captain Shelly Rood walked through nuclear bombs. Their POV is the Superpower.[00:30:00] – AI as Your Career Intelligence Officer: Six copy-and-run prompts that turn AI from a shortcut into a Superpower. Ring Assessment. Puke Session. Endure or Escape. This isn’t prompt engineering. It’s a system for seeing the shift early and repositioning before everyone else notices the ground moved.If you’re in the middle of a career quake right now, or you can feel the tremors starting, this mini-book will change how you read the ground under your feet.That’s how you convert turmoil into treasure.Arrrrrrr,Category Pirates 🏴‍☠️Eddie YoonChristopher LochheadPS: Help like-minded pirates “think different.”If reading this opened your mind to new and different thinking, share it with a friend or click the ❤️ button on this post so more people can learn about Category Pirates.

This is a public episode. If you'd like to discuss this with other subscribers or get access to bonus episodes, visit www.categorypirates.news/subscribeMost people think careers are built through planning.They’re not. They’re built through quakes.Unexpected moments that shake everything:Your jobYour identityYour relationshipsYour sense of what mattersYou don’t avoid these moments. You become because of them.This mini-book introduces a new way to understand your career—not as a ladder, but as a system of forces shaping you in real time.If you can learn to read those forces, you don’t just survive quakes. You use them.Here’s what you’ll get inside:[00:02:00] – Lifequakes Are the Rule, Not the Exception: Research shows we experience major life disruptions every 12–18 months, with 3–5 true “lifequakes” across adulthood. These aren’t linear or predictable—they’re messy, nonlinear, and they reshape everything. [00:07:00] – The Three Rings That Actually Define Your Career: Your career sits inside three interacting forces:Global quakes (AI, economy, war, culture)Organizational quakes (bosses, roles, pay, politics)Personal quakes (health, family, purpose)Most advice focuses on one. Winners learn to read all three—at the same time.[00:12:00] – Why Global Forces Shape Your Destiny More Than You Think: You don’t control macro shifts—AI, recessions, regulation—but they control what’s possible. [00:18:00] – Organizational Quakes: The Game You Think You’re Playing: Promotions, bosses, compensation, and role clarity feel like “the career.” They’re not. They’re one ring. Over-index here, and you miss the bigger game. Under-index, and you get crushed by politics and structure you didn’t see coming.[00:24:00] – Personal Quakes: The Ring That Actually Determines Everything: Your relationships, health, family, and sense of purpose are not separate from your career—they are your career infrastructure. The right people accelerate you. The wrong ones destroy you. And most people don’t realize this until it’s too late.[00:30:00] – Seven Truths About Quakes That Change How You See Everything: You can’t stop quakes—but you can change your POV about them.[00:36:00] – From Surviving Quakes to Becoming Quake-Wise: The goal isn’t a stable career. That’s a myth. The goal is to shorten the distance between shock and strategy. To read signals faster.Arrrrrrr,Category Pirates 🏴‍☠️Eddie YoonChristopher LochheadPS: Help like-minded pirates “think different.”If reading this opened your mind to new and different thinking, share it with a friend or click the ❤️ button on this post so more people can learn about Category Pirates.

This is a public episode. If you'd like to discuss this with other subscribers or get access to bonus episodes, visit www.categorypirates.news/subscribeMost people read about strategy. Pirates execute it.This is the first edition of Lightning Strike Legends—a series where we show real Pirates running real strikes with real revenue.Lydia Flacchini and Nick Kringus didn’t follow a marketing playbook. They built creator capital first—then pointed it at a single moment.Three weeks. $24K invested. $90K signed on day two. $270K in near-term pipeline. Up to $1M in total opportunity.That’s not marketing. That’s a Lightning Strike.Here’s what you’ll get inside:[00:01:00] – Why Creator Capital Comes Before Revenue: This strike didn’t work because of tactics. It worked because Lydia and Nick had already built the four capitals—intellectual, reputation, relationship, and financial. The strike didn’t create value. It revealed and monetized value that was already there.[00:06:30] – Finding Your Bandmate Multiplies Everything: Lydia (revenue scientist) and Nick (category strategist) weren’t just collaborators—they became a band. When two people with clear superpowers align around a shared problem and POV, the output isn’t additive. It’s exponential.[00:11:30] – The Legendary POV: Are You AI Invisible?: Their breakthrough wasn’t a tactic—it was a question. “Are you AI invisible?” reframed the entire personal injury legal market. As AI replaces search, both victims and lawyers are disappearing from discovery. That’s a category problem, not a marketing problem.[00:16:30] – Category Science > Conventional Wisdom: Their research revealed something shocking: SEO authority had almost zero correlation with AI visibility (0.076). That single number punched the industry in the face—and created instant word of mouth. [00:20:00] – The Strike Stack: Info War, Air War, Ground War: The strike wasn’t random—it was structured:Info War: The 0.076 insight and AI invisibility POVAir War: Booth + live podcast creating visibility and credibilityGround War: Real conversations, real diagnostics, real closingThe stronger the intellectual capital, the less financial capital you need.[00:24:00] – Close Before You Leave: Revenue Is the Goal: Lydia set the tone: “We need five clients before we leave.” By day two, they signed a $90K client. The strike paid for itself before they even left the conference.[00:27:00] – What’s Actually Stopping You From Striking: It’s whether you’ve mapped your creator capital and have the courage to act. Most people don’t lack opportunity—they walk past it, like the economists ignoring the $100 bill on the sidewalk.Arrrrrrr,Category Pirates 🏴‍☠️Eddie YoonChristopher LochheadPS: Help like-minded pirates “think different.”If reading this opened your mind to new and different thinking, share it with a friend or click the ❤️ button on this post so more people can learn about Category Pirates.

Welcome to Creator Capitalist Conversations, a series spotlighting Category Designers who have rejected traditional career paths and built lives around what makes them different. Our new book, Creator Capitalist, is available now. Get your copy here.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: [email protected],Category Pirates 🏴‍☠️Eddie YoonChristopher LochheadP.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.] This is a public episode. If you'd like to discuss this with other subscribers or get access to bonus episodes, visit www.categorypirates.news/subscribe

Welcome to Creator Capitalist Conversations, a series spotlighting Category Designers who have rejected traditional career paths and built lives around what makes them different. Our new book, Creator Capitalist, is available now. Get your copy here.Dear Friend, Subscriber, and Category Pirate,Most people think there are two kinds of people in the world.There are the creatives. The artists, the writers, the builders, the visionaries. The ones who make things. And then there are the capitalists. The business people, the operators, the money minds. The ones who monetize things.We have been told these are two separate buckets for so long that almost nobody stops to ask whether it is actually true.It isn’t.It’s a lie that you have to choose a side. That you are either a creator or a capitalist. That the two cannot live in the same person. Most people fall into this trap without ever realizing it, and it quietly limits everything: how they price their work, how they describe themselves, how much they believe they are allowed to claim.William Shakespeare co-owned the Globe Theatre. Twelve and a half percent equity, purchased while his contemporaries were getting paid per play. He did not write in isolation hoping posterity would find his genius. He built an enterprise around his work and retired wealthy.Andy Warhol called his studio the Factory. On purpose. “Being good in business is the most fascinating kind of art,” he said. He was not being provocative. He was making a precise observation from someone who had dissolved the boundary between creativity and commerce entirely.Taylor Swift did not just perform. When her masters were sold without her consent, she re-recorded her entire back catalog and turned the act of ownership into a cultural statement that made her Taylor’s Version releases more commercially successful than the originals. She was asleep in a hotel in Buenos Aires. And her thinking was making a difference to millions of people simultaneously.Different centuries. Same model.A creator and a capitalist are not opposites sitting on either end of a spectrum. They are the same person operating at full power.Shakespeare did not stop being an artist when he bought his equity stake. Warhol’s art still created an abundance of feelings when he ran the Factory like a business. Swift did not stop being a musician when she became a mogul. The myth that they are separate was about control. Keep the creatives over here focused on creating. Keep the business people over there focused on the money. When you split people in two, they are easier to manage and easier to underpay.Creator capitalists reject that split entirely.This week Pirate Christopher sat down with Jessica Miller of the It’s Your Offer podcast to lay this all out from first principles. If you have ever felt the pull of both worlds and been told you had to choose, this is the conversation that names what you have always known.We keep our best thinking for our Substack. We do not get promotional here often. But we also know where the real value lives and we would be doing you a disservice if we did not point you toward it. We would not be breaking that rule today if we did not believe this is the most valuable thing we have put out.If you already see categories everywhere. If you are already doing this work. If you read that and thought yes, that is exactly how I see the world: then it is time to go deeper.Here is where you go from here.If you are building toward six figures and you are still finding your superpower, still learning to see your category, still figuring out what only you can offer the world: the Creator Capitalist book and course are where you start. This is the thinking that makes everything else possible.Get the Creator Capitalist →If you are already doing six figures and you are ready to stop being compared to people who do not deserve to be in the same sentence as you: the Category Design Academy is where that work gets done.This is not a course. It is not a coaching program. It is a small, hand-selected room of founders, consultants, and operators who already see the world the way you do and are ready to build with it. Three working sessions a month with Pirate Eddie and Pirate Christopher. A community that does not end when the cohort does. People who will see your category before you can fully articulate it yourself and help you name what is already there.If you are ready to stop competing and start creating. If you are ready to build something the market has never seen before. If you have been waiting for the room where people think the way you think: this is the only room where that happens.Jessica felt that pull. She did not hesitate. She enrolled in the 2026 cohort early because she knew she was ready to stop explaining herself and start owning her category. She will be in the room when it begins May 4. If you have been feeling that same pull, that you are ready to stop competing, start creating, and become a category of one: we have the room where that happens.The investment is $10,000. We hand-select who gets in. Applications close April 27.Apply to the Category Design Academy →Not sure which is right for you yet?Learn more about the Academy →Here’s how to navigate this conversation:* 00:00 — The contradiction nobody questions: Most people assume creators and capitalists are two different kinds of people. Pirate Christopher explains why that assumption is costing you everything.* 10:10 — The existing market trap: Pirate Christopher walks through why that is a losing game and what the data from every tech company started between 2000 and 2015 actually reveals.* 18:40 — Different forces a choice. Better only creates comparison: The most important word in category design is not better. It is different. Italian or sushi is a choice. * 27:00 — Different is the last moat: AI is making two things that used to define professional value close to free: existing knowledge and the ability to execute against it. * 35:00 — AI is not your assistant. It is your co-founder: Most people are using AI wrong and you can hear it in the language the vendors use.* 44:00 — The four capitals flywheel: You have been building intellectual capital, relationship capital, reputation capital, and financial capital your entire career whether you realized it or not. * 52:00 — The value of your value: A woman with a career’s worth of accomplishment read the Creator Capitalist book and realized she had been letting others teach her to devalue her own value. * 1:01:00 — The greatest time in history to be alive: Why the people most afraid of AI are having the wrong conversation and what becomes possible when you stop asking what AI will take from you and start asking what you can now create that you never could before.This is one of the most complete articulations of the creator capitalist philosophy Pirate Christopher has put on record. If you have people in your life who are wrestling with what AI means for their career or their business, this is the episode to send them.Connect with Jessica:* Follow her on LinkedIn* Listen to the It’s Your Offer podcastArrrrrr,Category Pirates 🏴‍☠️Eddie YoonChristopher LochheadP.S. — If you have been thinking about the Academy…You are already doing real work. You are already in the market. You have a point of view the market has not fully caught up to yet. And you have been in enough rooms to know that most rooms are not built for people who think the way you do.This one is.A small group. Hand-selected. Three working sessions a month with Pirate Eddie and Pirate Christopher. People who will challenge your thinking, amplify your work, and see your category before you can fully name it yourself. This is the room you have been looking for, applications close April 27.If you are still building toward six figures and the Creator Capitalist framework is new to you, the book is your next step. The Academy will be here when you are ready.Apply to the Category Design Academy → This is a public episode. If you'd like to discuss this with other subscribers or get access to bonus episodes, visit www.categorypirates.news/subscribe

Shelly Rood is Jane Bond.Captain Shelly is a 16-year Army intelligence officer who spent her career doing one thing: reading situations most people couldn’t see, synthesizing what it meant, and briefing decision-makers on what to do about it.She was exceptionally good at it.She was also in the wrong place at the wrong time with the wrong people. Just like Charlie Chaplin’s Little Tramp. Not the decorated hero walking a linear path. The lovable character who keeps ending up in the middle of someone else’s mess, getting arrested for a riot he was just standing near.Pirate Shelly was very generous she was with her pain and Career and Life Quakes. She shared how her marriage to a fellow ROTC officer that unraveled into infidelity and abuse. The insecure male superiors who punished her for outperforming them. So she pivoted. She went to seminary. She became a chaplain. She built a course on moral injury. A community of 154 female veterans with 1,600 conversations in a single year. A bot, called Digital Shelly. A Substack. A second marriage she describes as life-changing.What Shelly has done, without necessarily using this language until now, is category design her own life. She took a superpower the Army trained her for, named the problem nobody else was solving for female veterans, and built an entirely new category of support around it. A peer intelligence system, where women who’ve been through it brief the women who are currently in it. She named it. She framed it. She’s claiming it.That is what a Creator Capitalist looks like. The woman veteran narrative has always been handed to someone else to write. Shelly became a category of one and picked up the pen herself.Here’s how to navigate this conversation:05:05 – Jane Bond and the bunker in South Korea: What a tactical all-source intelligence officer actually does, and why Shelly’s version of the job was cooler than most.08:18 – The Little Tramp: Why Shelly Rood is Charlie Chaplin’s character, not the decorated straight-line hero, and why that framing is more honest and more useful.10:21 – Detroit rooftops and the freshman 15: How she ended up in ROTC, a sorority, and the rifle team all at the same time.15:16 – Institutional betrayal: The sorority incident that made her choose the uniform over the Greek letters.17:20 – Sharing of partners: Christopher asks her to repeat herself. She does.22:18 – Ten years and a son: The marriage, the infidelity, the drinking, the divorce. And what it looked like from inside a military community where that behavior was normalized.31:51 – Accused of forgery. Accused of plagiarism. Failed grenade training: The pattern of being punished for competence, and the five years of hard thinking it took to understand why.38:56 – The news director who couldn’t finish the phrase: Shelly’s television career, the insecure boss, and Eddie on what it costs to be right versus what it costs to keep your job.43:10 – Moral injury: The concept that’s only been named in the last decade, why the only path through it is understanding the why, and why Charlie Chaplin’s audience always understands what the Tramp doesn’t.47:16 – Who takes care of the women: Shelly on the woman veteran narrative, what’s wrong with how it’s currently told, and what she wants to write instead.To connect with Shelly: Follow Shelly on LinkedInListen to the Hardcore and At Ease PodcastCheck out Mission AmbitionArrrrrr,Category Pirates 🏴‍☠️Eddie YoonChristopher LochheadP.S.—Shelly is a living example of what happens when someone takes their lived experience, names the problem only they are positioned to solve, and builds a category around it.If you’re ready to do the same, the Academy 4.0 is where that work gets done. If you’ve been watching from the sidelines wondering whether the Academy is the right next move for you, Shelly’s story is probably the most honest answer we could give.→ Learn more about the Academy here.→ Apply here. This is a public episode. If you'd like to discuss this with other subscribers or get access to bonus episodes, visit www.categorypirates.news/subscribe

This is a 🏴‍☠️ Founding Members–Only 🏴‍☠️ post. Founding Members get access to the Pirate Eddie Bot to ask category design questions, weekly actionable insights, the full library with 30+ audiobooks, 250+ mini-books, and more. See the Founders Deck here.Dear Friend, Subscriber, and Category Pirate,Last week, the same day Creator Capitalist launched, Pirate Christopher gave a keynote in San Diego. He built the entire speech around what happens when knowledge and execution become free, and creation becomes the only thing that matters.He closed with something that won’t leave people’s heads:“If you connect your different to making the biggest possible difference at scale with AI, you will have a different career. If not, you’ll suffer the fate of a knowledge worker.”There’s no third option.He’s given many a monster keynote. But this was different. Multiple men and women came up to ask if they could just hug him. He clearly struck a chord. The decades old Knowledge Worker deal is doneFor 67 years, the Knowledge Worker deal was simple: acquire valuable knowledge, get paid to apply it. Knowledge is power. Execution is everything.You were raised on that deal. You were rewarded for it. Promotions, titles, salaries—all of it is designed to keep you applying existing knowledge to existing problems. The system told you that knowing and executing were valuable things. And you believed it, because the paychecks confirmed it.Creating—the thing every five-year-old does without thinking—got relegated to the margins. To the weekend. To the “when I have time” pile. The thing that used to come naturally became the thing you needed permission for.Now knowledge is free. Execution is free. And creating—having a point of view, naming a problem nobody else has named, building a framework that didn’t exist before, designing something so different that people reorganize their thinking around it—is the only thing that’s scarce.The irony is brutal: the thing the system trained out of you is the only thing the market will pay for now.A five-year-old creates naturally. A fifty-five-year-old has been trained out of it.Get a few kids together. Give them paper and crayons. Leave the room for 20 minutes.They’ll draw. They’ll invent. They’ll argue about whose drawing is better. They’ll make up stories about what they drew. They’ll collaborate, compete, and create—without anyone telling them to. Without a framework. Without permission. Without a strategy meeting first.Every five-year-old is insanely creative. They won’t shut up. They’re full of ideas. They have more curiosity in a single afternoon than most boardrooms generate in a quarter.So you’d think by the time they’re 55, with decades of experience and knowledge layered on top of that natural creativity, they’d be the most creative people alive.The opposite happens.Somewhere between five and fifty-five, we got trained to stop creating and start executing. To stop asking “what if?” and start asking “what’s the deliverable?” To stop seeing what isn’t there yet and start optimizing what already is.The system rewarded us for it. Promotions, titles, salaries, corner offices—all of it designed to keep us applying existing knowledge to existing problems inside existing structures.AI just made that entire reward system obsolete. The executing and the knowing—the things the system trained us to prioritize over creating—are now the cheapest things on the planet.The creating—the thing every five-year-old does without thinking—is now the most valuable.This is either terrifying or the greatest opportunity of your life.It depends entirely on whether you have a framework for it.If you’re still trying to outsmart AI by knowing more, or outwork AI by executing harder, you’re going to lose. You’re playing the 67-year-old game with 67-year-old rules, and the rules just changed.If instead you connect your different—your superpower, the thing people come to you for, the thing that makes the biggest difference possible—to making a difference at scale with AI, everything changes.One person can now build what used to take an entire company. The Silicon Valley conversation has moved from “when will we see the first billion-dollar one-person company?” to “when will we see the first billion-dollar ARR one-person company?”The tools are here. The moment is here. The question isn’t whether AI will replace you.The question is: what should you create?Three things to sit with before Friday.1. When was the last time you created something that didn’t exist before?Not edited. Not optimized. Not iterated on someone else’s work. Actually created—from scratch—a framework, an idea, a point of view that was yours. If you can’t remember, that’s the signal. The system trained the creating out of you. It’s still in there. But you have to go looking for it.2. What do people come to you for that you’ve never charged for?The thing colleagues ask you about in the hallway. The thing friends text you about on weekends. The thing you do so naturally that it feels like it shouldn’t count as expertise. That’s your superpower. And it’s probably the most valuable thing about you—precisely because you’ve never treated it that way.3. If you could only do one thing for the rest of your career, what would it be?Not the thing you’re good at. Not the thing on your resume. The thing that—if everything else went away and you could only keep one piece of what you do—you would choose. That’s where the creating lives. That’s what AI can’t replicate. And that’s the foundation of everything a Creator Capitalist builds on.Write your answers down. Don’t type them. Don’t ask AI. Sit with them.Friday: Career Quakes drops.AI is the biggest career quake in a generation. Maybe the biggest ever.We keep using that word—quake—because it’s precise. Not a disruption. Not a trend. Not a “shift in the landscape.” A quake. The kind that shakes all three rings of your life simultaneously: the global forces you can’t control, the organizational forces reshaping your workplace, and the personal forces that decide whether you break or build.Most career advice picks one ring and pretends the other two don’t exist. The business books obsess over global disruption. The leadership books obsess over promotions. The self-help books obsess over purpose. None of them talk about what happens when all three rings go red at the same time.On Friday, we’re releasing a new mini-book called Career Quakes. It’s about the moments that shake your career—and the framework for using them to build instead of break. Career Quakes is a paid publication. More on how to access it below.If you’re ready to become a Creator Capitalist through this quake—not just read about it—the Creator Capitalist course closes Friday.Everything in this email—the five-year-old who stopped creating, the 67-year-old Knowledge Worker deal that just expired, the question of what you should create next—the Creator Capitalist Course is the system for answering it.Your superpower. Your Four Capitals. Your offer ladder. Your pricing. Framework by framework, with AI tools built into every step. The course includes the $100 Complete Collection of the book (hardcover, ebook, audiobook) plus three guided modules.119 people went through this course last year. They uncovered $425M in quantified outcomes they didn’t know they had.The course closes Friday, March 27 at midnight. We haven’t opened it in over a year. We don’t know when we’ll open it again.This is the week to go all in on being a Creator Capitalist.Already bought the book and want to upgrade? Email [email protected] with your receipt for a discount code.Not ready for the course? Join the inner circle.If you want to start jamming on these ideas with the thinking partner that makes them personal—and get access to everything we publish, including Career Quakes on Friday—the Founding Membership is the way in.Founding members get:* The Pirate Eddie Bot—the only AI trained on Category Design and Creator Capitalism* 30+ audiobooks * Free copies of our six full-sized books (A Marketer’s Guide to Category Design, The 22 Laws of Category Design, The Category Design Toolkit, Snow Leopard, Thinker’s High, and Lightning Strike Marketing)* Invites to founder-only virtual workshops (held two to three times a year)* The Category Vault and the full 250+ mini-book libraryArrrrrr,Category Pirates 🏴‍☠️Eddie YoonChristopher LochheadP.S. — Not ready for the course or Founding? Get the book:* Paperback on Amazon — $35* Ebook — $35 (instant access)* Audiobook — $35 (instant access)* The Complete Collection — $100 (hardcover + ebook + audiobook) This is a public episode. If you'd like to discuss this with other subscribers or get access to bonus episodes, visit www.categorypirates.news/subscribe

Lydia Flocchini is a lawyer who decided the law wasn’t enough.Nick Kringas is a restaurateur, SEO pioneer, and serial category designer.Together, they walked into a legal tech conference with a $24,000 budget, a two-week runway, and a question that stopped attorneys cold: Are you AI invisible?They left with a signed client with $90,000 in revenue, 15 warm prospects, and a pipeline trajectory toward $300,000 to $1,000,000 in annual recurring revenue.That’s a lightning strike. And it's exactly what a Creator Capitalist looks like in action.If you read Lightning Strike Legends, you already know their receipts. This conversation is where you hear them tell it themselves—and where the story gets a lot more interesting.Lightning Strike Legends: One Strike, Two Creator Capitalists, Three Weeks For A 4x ROICategory Pirates 🏴‍☠️·Mar 13Read full storyThe value of a business bandmate.We borrowed these words from a LinkedIn post by Pirate LydiaMost people build careers. Very few find their business bandmate.One of the most important and rare things in business is finding someone you’re meant to build with. Not just collaborate. Not just partner. But someone who sees the world the way you do and challenges you to see it differently.I found my bandmate through the Category Design Academy. I still remember when Pirate Eddie Yoon said, “Lydia, you need to meet Nick Kringas. He’s also in legal.”What began as a few conversations quickly turned into a shared point of view.We talked about the shifts reshaping hashtag#legal -AI, private equity, generational change, and how marketing and business development are evolving in an AI-driven world. We call this the 𝗔𝗜 𝗩𝗶𝘀𝗶𝗯𝗶𝗹𝗶𝘁𝘆 𝗥𝗲𝘀𝗲𝘁.Then Nick told me he was rebranding his company and asked me to help. The timeline was tight. He knew I had led rebrands before. I said yes.From there, we got to work- building, collaborating, and sharing ideas leading up to the PILMMA's AI for PI Expo and beyond.And somewhere along the way we formed a partnership with a shared mission and purpose to help law firms navigate the market siege.I'm excited to share that Nick and I are now featured in 𝗖𝗿𝗲𝗮𝘁𝗼𝗿 𝗖𝗮𝗽𝗶𝘁𝗮𝗹𝗶𝘀𝘁, 𝗖𝗵𝗮𝗽𝘁𝗲𝗿 𝟭𝟰: 𝗙𝗶𝗻𝗱 𝗬𝗼𝘂𝗿 𝗕𝗮𝗻𝗱𝗺𝗮𝘁𝗲𝘀.“This is the story of how two solo pirates became bandmates—and why finding your bandmates might be the most important decision you make as a creator capitalist.”This isn’t just our story. It’s about orchestrating a lightning strike, one of the most valuable skills you can learn as a creator capitalist.𝗪𝗵𝗮𝘁 𝘀𝗵𝗼𝘂𝗹𝗱 𝘆𝗼𝘂 𝗹𝗼𝗼𝗸 𝗳𝗼𝗿 𝗶𝗻 𝗮 𝗯𝗮𝗻𝗱𝗺𝗮𝘁𝗲?Shared language: We think in category design. We don’t follow markets, we create them.Shared experience: First-generation. Children of immigrants. Shaped by the American Dream. That gives you resilience and a lens rooted in possibility.Deep expertise: Nearly 50 years combined in legal. Millions in outcomes. Your intellectual and reputational capital are your leverage.Challenge each other: A bandmate sharpens your thinking. We challenge ourselves all the time to think differently and reject the premise.No ego: You elevate each other. Always.Shared mission: We want to help the injured and the attorneys who serve them. Belief and conviction in your mission are everything.We’ve also been fortunate to learn from Eddie Yoon and Christopher Lochhead 🇺🇸🇮🇱🏴‍☠️,true bandmates we admire and aspire to.I’m incredibly grateful to be on this journey with Nick, and part of a community that pushes me to think bigger and grow.Your bandmate might be in our Pirate ShipLydia joined the second cohort. Nick joined the third. Eddie connected them. They started talking about the legal industry from opposite coasts—Lydia in Silicon Valley watching AI ads on every billboard, Nick in New York, talking to personal injury lawyers still measuring success in a different kind of billboard.Same industry. Same category design lens. Complimentary superpowers.What the Academy gave them individually was just as important as the introduction. Lydia said it plainly: it wasn’t just category designing her business. It was category designing her—who she wanted to be in this next chapter. Nick said that after joining the Academy, he started waking up in the middle of the night with ideas he couldn’t turn off.That’s what deep thinking does when you’re surrounded by people doing the same.Then Nick mentioned a conference. Two weeks away. Lydia said yes before she’d thought it through.What you don’t get in the mini-book is the moment Nick knew he’d found his person. He’d been going back and forth with Lydia for days—him thinking about the long game, her pulling him back to earth with pipeline math. Then she showed him a languaging framework she’d built from weeks of their conversations, texts, and Slack messages. He had a tear in his eye. He called it a masterpiece.That’s called Relationship Capital.That lead to Intellectual Capital.“Are you AI invisible?”That’s the problem they named, framed, and claimed.Law firms have spent years and fortunes on SEO. What Nick and Lydia discovered in their data: among the 80 law firms they analyzed, the ones that invested most heavily in SEO had a median AI visibility score of zero. The correlation between SEO authority and AI visibility?0.076.AI doesn’t respond to the same signals SEO does. The playbook that made you visible to Google actively makes you invisible to AI.Every personal injury attorney who woke up at night worrying about where their next case would come from just got a new reason to worry—and a new category of solution to buy.The minute the lawyers at the conference started using the words back at them—“wait, am I AI invisible?”—Nick and Lydia had already won the framing and naming game.This is what the four Creator Capitals look like when they compound. Intellectual capital—a problem nobody had named. Reputation capital—two people already known in the space. Relationship capital—a bandmate found inside the Academy. Financial capital—a $24,000 bet with a 12x return. You don’t stumble into that. You build it. (And the book walks you through it.)If their story resonates with you…It’s in the book. The lightning strike playbook. The bandmate framework. What it means to be a creator capitalist who owns what they create instead of renting out their expertise to someone else’s company.Creator Capitalist is out now. Nick and Lydia’s full story is one of the featured case studies. If reading this makes you think that could be me—that’s exactly who we wrote it for.Get the book here: creatorcapitalist.ai/Here’s how to navigate this conversation:00:00 – When the student is ready: Lydia’s Odyssey from maritime law to legal tech to the Academy—and why timing is everything.10:59 – Nick’s superpower revealed: How 30,000-foot market thinking showed up in a Greek restaurant before he ever heard the words “category design.”16:54 – The bar, the restaurant, and the borrowed $139,000: Nick’s origin story as an intuitive category designer—and why losing the bar shaped how he sees the world.24:22 – How they found each other: Two different cohorts, opposite coasts, one industry, and an introduction from Eddie.33:05 – From advisor to bandmate: How the partnership formed faster than either expected—and why the moment Nick read Lydia’s languaging framework, he had a tear in his eye.41:09 – The lightning strike: Two weeks, $24,000, a corner booth, and “Are you AI invisible?”47:05 – When they parroted the words back: The moment Nick and Lydia knew they’d won the framing and naming game.55:52 – The first client paid for the strike: The ROI math on a category-designed lightning strike.1:01:00 – The data that changes everything: 80 law firms, a 0.076 correlation, and why heavy SEO investment predicts AI invisibility.1:09:37 – “The AI you use today will be the worst AI you use”: Christopher on the compounding returns of AI as a thinking partner.1:15:07 – Finding yourself before finding your bandmate: Why the individual work in the Academy made the partnership possible—and why Lydia wouldn’t let Nick touch the flag.This is what Creator Capitalism looks like in practice.Not a side hustle. Not a consulting arrangement. A category, a co-creator, a lightning strike, and a business that didn’t exist 90 days ago generating six-figure recurring revenue.Nick and Lydia are the case study. Creator Capitalist is the playbook. The course is where you do the work.Creator Capitalist is available now—and the course closes March 27th. If you’ve been waiting for proof that this is real, you just read it.→ Get the book and join the course here.Arrrrrr,Category Pirates 🏴‍☠️Eddie YoonChristopher LochheadP.S.—Nick and Lydia didn’t stumble into this.They did the work—the Academy, the individual thinking, the willingness to plant a flag in a category nobody had named yet. Their bandmate was sitting in a different cohort. Their category was sitting in an industry everyone else had written off as change-resistant.Our current cohort is graduating soon. The next one starts in May. If you’ve been watching from the sidelines wondering whether the Academy is the right next move for you, Nick and Lydia’s story is probably the most honest answer we could give.→ Join the waitlist here.And if you’re not ready for the Academy yet—start with the book. Creator Capitalist is available now. The course closes March 27th.→ Buy the book and join the course here. This is a public episode. If you'd like to discuss this with other subscribers or get access to bonus episodes, visit www.categorypirates.news/subscribe

New research is showing what we’ve suspected for a while: on average, AI is making people stupider over time.Not because AI is bad. Because most people use it badly.They show up with radical obvious—”write me a blog post about the 10 smart things to do in marketing for 2026”—and get radical obvious back. They skim it, copy-paste it, and move on. Their core premise never gets challenged. Their thinking never improves. AI becomes a mirror that makes them look smarter without making them actually smarter.That’s the trap.AI is, by definition, a synthesis of all existing knowledge. When you ask it obvious questions, you get the average of everything that’s already been said. You get a very polished, very fast version of what everybody already knows.Creator Capitalists do the opposite.They don’t use AI to do their thinking. They use AI to help their thinking. And the difference between those two things is the entire ballgame.When you live in the obvious, AI makes you stupider. When you live in the non-obvious—and connect it to the obvious—you create legendary magic.Here’s what that looks like in practice.In this conversation, Pirate Eddie uploaded 20 Creator Capitalist profiles into Claude. Not structured data. Not a spreadsheet. Just stories—unstructured, messy, human stories about how 20 different people made the shift from Knowledge Worker to Creator Capitalist.But here’s the part most people would skip: Eddie didn’t say “find me something cool.” He showed up with a hypothesis. A point of view. A specific lens he wanted to pressure-test.That hypothesis is the difference between using AI to think for you and using AI to think with you. Without it, Claude would have produced a generic word cloud. With it, Claude produced category science—origin story buckets, career stage analysis, seniority distribution, company size breakdowns—that none of us would have created on our own.Eddie brought the judgment. Claude brought the processing power. Together, they created Intellectual Capital that neither could have produced alone.Creator Capitalist goes deep on how to use AI to scale your Intellectual Capital as a Creator Capitalist. The book launches March 17. Join the waitlist at creatorcapitalist.ai, and you'll get the Introduction and the opening of Section 1 for free, delivered to your inbox immediately. You'll also be able to order a full day early on March 16—before the public launch.And then Eddie did something else that matters. He prompted the charts—”first one, horizontal bar. Second, vertical bar. Third, I don’t like pie charts, you come up with something different”—and Claude delivered visualization formats Eddie had never seen before. He said “look at our website, grab our color scheme” and got publication-ready graphics.What would have taken a consulting team a week happened in one sitting. AI isn’t magic without thinking worth amplifying.AI doesn’t need you to be clever. It needs you to give context. And context starts with having a point of view.The conversation goes somewhere unexpected from there.Bri didn’t recognize herself in the data. Claude categorized her as “accidental discovery”—but she would have placed herself in “frustration, trauma, survival.” Both are true. It turns out Creator Capitalist journeys look different from the inside than the outside. That tension—between how you see your own story and how the data sees it—opens up something none of us anticipated.Christopher shares a moment of vulnerability that will surprise anyone who thinks confidence comes standard with success. And the Circleback Neenanana makes its official debut as a concept. (You’ll know it when you hear it. And you’ll immediately think of three people in your own life.)The data itself—what the 20 profiles actually reveal about who becomes a Creator Capitalist and why—we covered in our mini-book last week. This conversation is different. This is what it looks like when three people sit down with AI-generated category science and start jamming on what it means, where it breaks, and what it tells you about your own path.Here’s how to navigate this conversation:00:01 – The setup: the book is days away, the Founding 50 are in, and Eddie has done something with Claude that changes how we think about category science.00:44 – Word crunching, not number crunching: why analyzing unstructured stories with AI is fundamentally different from everything consulting has done before—and why it only works when you show up with a hypothesis.06:18 – The Circleback Neenanana: Christopher on the special fuel of “I’ll show you”—and why some of the best Creator Capitalists were forged in the fire of getting screwed over.08:31 – The less-celebrated paths are the majority: why frustration, hobby, and accidental discovery outweigh deliberate professional reinvention in the data—and why that should give you confidence.15:11 – “I would not have placed myself in that bucket”: Bri on why Claude categorized her differently than she would have categorized herself.23:48 – The meta-lesson: Christopher names what Eddie is demonstrating in real time. One person creating publication-quality category science with AI. “That’s the definition of leverage.”29:02 – What AI can’t do: the human work—writing the profiles, knowing the people, bringing a hypothesis—is still everything. AI organized the data. Humans created the data.32:40 – Does pedigree matter? Rafi Mohammed (PhD from Cornell) versus Coffeezilla (nobody knows his real name). Both Creator Capitalists. Christopher’s answer will not be diplomatic.AI can produce the same faster than any human ever could. The people who show up with obvious get obvious back at unprecedented speed. The people who show up with a point of view, a non-obvious lens, a hypothesis worth testing—they get leverage that didn’t exist two years ago.This conversation is proof. One hypothesis. One AI. Twenty stories. And category science that would have been impossible without both the human and the machine.Chapter 20 of Creator Capitalist is called “Vibe Creating”—and it breaks down exactly how to work with AI as a co-creator, not a content machine. The book launches March 17.The book launches March 17.Join the waitlist at creatorcapitalist.ai. Here’s what you get:The free opening of the book—immediately. The Introduction and the start of Section 1, delivered to your inbox the moment you sign up. Start reading today.Early ordering on March 16—a full day before the public launch. You’ll be reading and posting while everyone else is still finding out the book exists.A launch-week-only bonus we’re announcing soon that won’t be available after March 21. Waitlist members hear about it first.👉 Join the waitlist here.The people who show up to AI with thinking worth amplifying are about to have the most unfair advantage in the history of work. The book shows you how to be one of them.Arrrrrr,Category Pirates 🏴‍☠️Eddie YoonChristopher Lochhead This is a public episode. If you'd like to discuss this with other subscribers or get access to bonus episodes, visit www.categorypirates.news/subscribe

Jeff Klimkowski didn’t plan on his career ending up in the toilet (pun intended.)He was a Deutsche Bank investment banker. The kind of kid who made his sister drive him to school so he could read the Wall Street Journal in the passenger seat. He had the job. The trajectory. The spreadsheet-perfect life plan.Then his childhood friends had too many burritos and a dumb idea.Flushable wipes for men. They called it DUDE Wipes.Jeff left banking to become CFO, co-founder, and—for a while—the company’s personal line of credit. His i-banking bonuses funded the working capital. His cash and DUDE’s cash were the same thing.That detail matters more than anything else in this conversation.When your money and the company’s money are the same pile, you think differently about every dollar.You can’t be reckless. You can’t be timid. You have to be precise—because the category is moving faster than your spreadsheets and hesitation means someone else defines the future.After Shark Tank, Jeff and co-founder Sean Riley pitched 20 to 30 VCs. Every single one said no. The biggest rejection? “You’ll never get guys to use wipes.”So they got profitable.Q4 2016. First profitable quarter. They haven’t looked back since. No outside capital beyond Mark Cuban’s original Shark Tank check until they hit escape velocity.DUDE Wipes crossed $300M in annual retail revenue. They’re growing roughly 50% per year. And Jeff has never been more bullish in the company’s history.Jeff didn’t just become CFO. He redesigned what the role means.At DUDE Wipes, four verticals roll up to the CFO: Finance and accountingFP&ASales strategySupply chain. The problem with how the industry defines the job is that most people think it’s just the first one.Jeff sits in every major Walmart and Target line review alongside Sean. He hears from the buyer’s mouth what their long-term strategy is—so his forecasts aren’t built on salespeople’s optimism alone. He goes to co-manufacturer meetings so he can look at the whites of the buyer’s eyes before he commits working capital to inventory.This is not how most CFOs operate.Most CFOs sit in a skybox. Jeff is on the field.And here’s his financial philosophy in one sentence: “EBITDA is the most overrated metric on the face of the planet.”Zero free cash flow. That’s the goal.Not because DUDE Wipes isn’t profitable. Because every dollar of EBITDA gets reinvested—into working capital, CapEx, and marketing—until free cash flow hits zero at year’s end.Zero means Jeff is deploying capital at the exact speed the category demands.Too much free cash flow? You’re not investing enough. You lack conviction. The category will outgrow you while you sit on cash.Negative free cash flow? You’re over your skis. You’ll need to raise money, dilute equity, and lose control.Zero is the surfer sitting in the pocket of the wave.Jeff knows the max growth rate they can sustain in a given year because of this discipline. Right now: 50% per annum at zero free cash flow. When numbers get big, 50% is a big number.And it’s not set-it-and-forget-it. They’re tweaking the plan constantly—rolling 12 months on the finance side, rolling 24 months on supply chain. New data in, new adjustments out.The make-free-cash-flow button.Eddie asked Jeff: when you need to push the free cash flow number, what do you press?The first answer was boring and brilliant: cash collections from retailers.Nobody was quarterbacking receivables. Invoices were getting lost in EDI transmissions. POs weren’t registering correctly between systems. Charge-backs went uncontested. It’s the kind of work nobody glamorizes—but hiring one person to own it improved cash collection by 40%.Now they’re layering in AI agents to match invoices, flag errors, and automate the back-and-forth with retailer portals. The person quarterbacks. The agents do the grunt work.Second answer: SKU-level demand planning. DUDE Wipes knows how much they’ll sell. The problem is the mix—selling the right product at the right time to the right channel. When a new innovation outperforms expectations, there’s a 90–120 day lead time before they can adjust production. AI that ingests retailer data and optimizes assortment by channel compresses that gap.Real example: DUDE Wipes was running promotions at food retailers and only seeing 10–15% lift versus competitors. Why? They were selling out by Wednesday. Empty shelves for the rest of the week. High-growth category problems that only show up when you look at the data with precision.Meet Diesel Dan.Greg Brown, DUDE Wipes’ SVP of Ops and Technology, built an AI agent called Diesel Dan.Here’s what Diesel Dan does: when the manufacturer finishes a production run, an automated report gets sent over. Diesel Dan reads the report, books trucks across three counterparties, maximizes weight and volume per load, and notifies the operations team. Fully automated.Before Diesel Dan, inventory piled up at the manufacturer because trucks weren’t getting booked fast enough. That meant less production capacity. That meant slower growth. That meant working capital sitting in the wrong place at the wrong time.Dan fixed the bottleneck. Stockouts dropped. Freight costs stabilized. And the operations floor went from reactive to predictive.As Jeff put it: “Dan never sleeps, never guesses, and never forgets.”This episode isn’t about spreadsheets.Or accounting.Or even AI.It’s about what happens when the CFO stops being the department of no and starts designing the financial system that powers category creation.Jeff’s approach works because the conditions force it. Skin in the game. A new category that didn’t exist. And a bootstrap discipline that makes every dollar earn its spot—or get cut.That’s the Agentic CFO.Here’s how to navigate this conversation:00:00 – From Deutsche Bank to DUDE Wipes: Jeff’s origin story—the Wall Street Journal in the passenger seat, the dream job, and the childhood friends who derailed everything.01:59 – The four verticals of a real CFO: Finance & accounting, FP&A, sales strategy, and supply chain. Why most people only know about the first one.09:06 – Investing 18 months ahead of demand: Writing checks for CapEx three years out. Why Jeff sits in every Walmart and Target line review. And why he’s been wrong on the downside of every forecast.16:54 – The VC rejection that saved DUDE Wipes: 20–30 meetings after Shark Tank. Every one said no. “You’ll never get guys to use wipes.” So they got profitable instead.18:48 – “EBITDA is the most overrated metric on the face of the planet.” Jeff’s financial North Star: free cash flow equals zero. What that means, why it works, and how it sets the pace for growth.26:35 – The make-free-cash-flow button: Cash collections, AI-powered invoice matching, and a 40% improvement from one hire.31:23 – SKU-level demand planning with AI: The working capital problem nobody talks about—selling the right mix at the right time.34:50 – Selling out by Wednesday: Why DUDE Wipes’ promotions were underperforming and what they found when they looked closer.36:30 – Diesel Dan: The AI agent that books trucks, maximizes loads, and turned DUDE Wipes’ supply chain from reactive to predictive.41:53 – Jeff’s AI wish list: Sales strategy, demand planning, and why legal is about to get 70–80% automated.44:59 – Why Jeff said yes: Credibility, alignment with strategy, and the only pitch that works—”here’s how many thousands of hours this saves.”This conversation is the case study. The Agentic CFO is the system.In the mini-book, we break down Milton Friedman’s four ways to spend money, the four CFO archetypes (Arena, Dividend, Enabler, and Government), why free cash flow—not EBITDA—is the strategic metric of belief, and the five-step playbook for designing an Agentic finance system with AI agents.Jeff is the Arena CFO. Which quadrant are you in?Read The Agentic CFOTo connect with Jeff:Jeff Klimkowski on LinkedInDUDE WipesArrrrrr,Category Pirates 🏴‍☠️Eddie YoonChristopher Lochhead This is a public episode. If you'd like to discuss this with other subscribers or get access to bonus episodes, visit www.categorypirates.news/subscribe

Dear Friend, Subscriber, and Category Pirate,This episode is about the most undervalued skill in the world right now: thinking.Not “consuming content” thinking. Not “I read a thread on X” thinking. Not “my algorithm told me what to believe” thinking.Real thinking. The kind where you sit with an idea long enough that it changes you.We call this Thinker’s High.Today, we’re talking about where it came from, why we turned it into a book, and why it might be the most important thing we’ve ever made—for you and for the people in your life who need Category Design but don’t know it yet.This is the book you hand someone when they ask: “What is this Category Design thing you keep talking about?”Gift it to your coworker. Your kid heading to college. Your work spouse for Valentine’s Day. (Eight days away. You’re welcome. Get it here.)Or gift it to yourself so you can see the world through a category design lens every single day.But first—a taste of what’s inside. Three Proverbs. Three Ways To Think Differently This Week.Every proverb in Thinker’s High comes with four layers: What (the idea)So What (why it matters)Now What (what to do today) AI Prompts (to jam on the idea with your AI co-founder). Here are three from three different chapters:“He or she who frames the problem owns the solution.”(Chapter 1: Clarity—from the Position Yourself Or Be Positioned mini-book)What: The person who defines the problem sets the terms of the game. If you frame the problem, you decide what matters, what doesn’t, and what the solution must look like. Everyone else is forced to play on your field. Think about Salesforce: instead of “CRM software,” they framed the problem as “the death of installed software.” That single move made “cloud” the only credible solution—and Salesforce owned it. The same is true in careers: if you’re the one who names the enemy and makes others see it, you become the obvious choice to solve it.So What: Most people rush to pitch solutions. But in markets—and in life—the power lies in problem definition. Economically, whoever frames the problem first captures disproportionate value, because they shape how capital, talent, and customers flow. Emotionally, people rally around the person who says, “This is what’s broken, and here’s why it matters.” Culturally, movements are built not on shiny solutions but on reframed problems: climate change reframed as a climate emergency, phones reframed as life hubs, AI reframed as the new operating system. Own the problem, and you automatically own the path forward.Now What: Stop pitching your product or résumé. Start framing the problem. Write a one-sentence enemy statement: “The real problem with [old way] is [painful truth].” Then create a FROM-TO contrast that makes the old way look obsolete and your way look inevitable. Use this language in every investor pitch, job interview, and customer conversation. Make your name synonymous with the problem you’ve defined. Once you do, the solution points straight back to you.AI Prompts:Draft 5 FROM-TOs that make the old way obsolete and my solution space inevitable.Rewrite my pitch deck opener so it starts with the framed problem, not the product.Show me examples of legendary companies that reframed their market’s problem and won.Create a 7-day publishing plan that frames and names the problem I want to own.“Reject the premise.”(Chapter 2: Courage—from The Innovator’s Delusion mini-book)What: Every category is founded on invisible assumptions. Coffee must be made one pot at a time. Dolls must be beautiful with great clothes. When it comes to vacuum cleaners, the more horsepower, the better. Most fail because they never question it. Keurig, American Girl, and Roomba all rejected the premise. “Disrupt yourself.” “Act like a startup.” “Build a skunkworks team.” These are smart strategies until you realize they’re based on the wrong premise. When you play by the wrong rules, you don’t just lose—you disqualify yourself from the game you were built to win.So What: Following the default playbook leads to default results. Startups win because they reject the premise. Incumbents can stay the Category King by rejecting the premise as well. Amazon rejected the premise by niching down on e-commerce books. After they became the Category King of e-commerce, they rejected the premise of being a retailer via Amazon Marketplace, allowing competitors to sell on their platform. Janus Motorcycles is thriving at a stunning 62% growth rate in a mature market. Why? Janus has crafted a unique motorcycling experience called “rambling.” This isn’t just about hopping on a bike; it’s about embracing the journey and ditching the daily grind for a leisurely adventure on two wheels. Because they’re not competing on speed or price. They’re redefining what riding can mean—creating a new niche and attracting loyal Superconsumers who want more than just a commute.Now What: Question everything. It takes asking ‘why’ seven times like an annoying toddler until you can actually see the fundamental premise with clear eyes. Gather your leadership team and identify one dominant industry belief you want to reject. Then, reframe the conversation. The companies that win don’t adapt to the narrative. They rewrite it.AI Prompts: What assumptions are we operating under that might no longer be true?Are we solving a problem—or reacting to someone else’s framing of it?What industry dogma do we need to reject to play our own game?If we designed the rules from scratch, what would they look like?“Marketing that does not produce revenue is called arts and crafts.”(Chapter 5: Marketing—from The 3 Marketing Metrics To Rule Them All mini-book)What: Marketing isn’t decoration—it’s a weapon. If your campaigns aren’t driving pipeline, closing deals, or creating exponential word-of-mouth, then they’re not a strategy. They’re theater. The job of marketing is to generate belief that moves the market—and belief that moves the market should move revenue. Otherwise, you’re just coloring inside the lines and calling it growth.So What: Too many teams treat marketing like a cost center or a brand awareness sandbox. They chase vanity metrics, polish taglines, and publish content that makes the team proud—but not the cash register sing. The result? Bloated campaigns, budget cuts, and a credibility gap with the CEO. Marketing isn’t about activity. It’s about acceleration.Now What: Audit your marketing backlog. What projects are tied directly to revenue outcomes, and what’s just brand therapy? Rebuild your roadmap around Lightning Strikes that generate attention, word-of-mouth, and strategic pipeline. Tie every campaign to a dollar goal and a belief shift. If it doesn’t move revenue, cut it or fix it.AI Prompts: Which of our current marketing activities directly drive revenue, and which don’t?What belief do we need to create in the market to accelerate deals?How can we turn our next campaign into a Lightning Strike that generates revenue now?If we had to cut 80% of our marketing, what 20% would we keep because it pays?That’s 3 out of 52.Each one designed to stop you mid-scroll and start you mid-thought.(Already know you need this on your coffee table? You can get it here.)Thinking About Thinking Is The Most Important Kind Of ThinkingEveryone’s scrambling to learn prompts. Watching tutorials. Optimizing what they feed AI.Nobody’s asking: What am I actually thinking—and why?There’s a difference between reflexive thinking and reflective thinking. Reflexive is fast, automatic, unquestioned. It makes you feel productive while you recycle the same ideas everyone else has. Reflective is where you pause and ask: Where did that belief come from? Is it a fact, a filter, or a feeling?Most of us were taught what to think our entire lives. By school. By media. By marketing.Thinker’s High is what happens when you pierce through being told what to think and start doing the thinking yourself.It’s the dopamine hit you get when you shift from consuming ideas to generating them. Shaping them. Turning them into value that changes someone’s life.Once you experience it, you get addicted. You start asking “why” five to seven times. You start realizing the assumptions you had were never yours. You start designing new futures instead of decorating old ones.It’s a runner’s high for your mind. Except the more you do it, the more valuable you become.Why A Book Of Proverbs (Not Another Mini-Book)We’ve written over 200 mini-books. Some of our best lines—the ones we come back to in our own jams, the ones Pirates quote back to us—get buried inside 10,000-word pieces. Highlighted once. Never found again.So we asked: what if we extracted the sharpest lines across everything we’ve ever written and built a book designed to be used, not read?We started with AI. Ingested all 200+ mini-books. Extracted roughly 4,000 candidate quotes. Built a scoring system. Then we went in as humans and picked the 52 that made the final cut.10 chapters: Clarity. Courage. Treasure. Creativity. Marketing. Relationships. AI. Future. Simplicity. Legendary.Open any page. Find what you’re looking for. Start thinking.👉 Order your copy of Thinker’s High here.Here’s how to navigate this conversation:00:00 – What Is Thinker’s High? The origins of the concept and why human thinking is the most important skill in the age of AI.04:59 – Thinking About Thinking: Why most of us have been taught what to think, not how to think—and why that distinction changes everything.08:39 – The 10 Chapters: How we organized 52 proverbs across clarity, courage, treasure, creativity, marketing, relationships, AI, future, simplicity, and legendary—and how to use each one when you’re stuck.11:47 – How We Used AI To Write This Book: We cranked the dial to 11, extracted 4,000 quotes, and learned what AI can and can’t do in the book creation process. A behind-the-scenes look at the process—useful for anyone writing books with AI.14:57 – The Gift Strategy: Why this book was designed to be gifted—and why gifting is the most underused superconsumer strategy in the world.15:24 – The Richard Bach Inspiration: How Pirate Christopher’s favorite childhood book inspired the serendipity design of Thinker’s High.17:53 – Why It’s Not On Amazon: We walked away from the largest book retailer on earth. Because we practice what we preach.You won't find it on Amazon. On purpose. This is a direct relationship between us and you—no algorithm, no comparison carousel, no middleman.Grab Thinker’s High for yourself (or gift it) here. Arrrrrrr,Category Pirates 🏴‍☠️Eddie YoonChristopher LochheadP.S. - Each proverb comes with AI prompts designed to be jammed on with the Pirate Eddie Bot.The prompts work with any AI. But they work best with the Pirate Eddie Bot—who’s trained on our entire mini-book library and can take the proverb deeper, apply it to your specific business, and walk you through the full framework behind each quote.Book + Eddie = the full Thinker's High experience. If you're a Founding Subscriber, you already have the Pirate Eddie Bot. If you're not, now you know what you're missing.Join the inner circle here.P.P.S. - This is Volume 1.There will be a Volume 2. Probably a Volume 3. We’re building a collector’s set because words matter and the more mini-books we write, the more legendary quotes we extract. But this is where it starts.Get your Volume 1 copy → CategoryPirates.store This is a public episode. If you'd like to discuss this with other subscribers or get access to bonus episodes, visit www.categorypirates.news/subscribe

Good CEOs obsess over the scoreboard.Great CEOs obsesses over how the game is played.That’s the difference between managing a P&L and creating a category.In this conversation, we sit down with Clint Carnell—a CEO who’s held the title six different times across 27 years. Not because he couldn’t make one company work. But because he mastered the category pattern that makes every company work.Most people think being a CEO is about strategy, people, and financial performance.Clint knows it’s simpler than that.If your customer isn’t successful with their customer, you don’t have a sustainable business.That clarity came from watching his father run a design firm in Seattle during the 70s and 80s. Clint would play with Hot Wheels on the floor while his dad obsessed over what couples designing homes actually needed. Not what looked impressive. Not what won awards. What made them successful.His father built a referral machine by operating out of abundance in a small town where you couldn’t cheat people and survive.That became Clint’s operating system.Across wildly different industries—from software to skincare—the same pattern shows up:Lead with the customer’s customer. Most CEOs think about their customer. Clint thinks about who their customer serves. When you make your customer more successful with their customers, price becomes irrelevant.Trust compounds faster than revenue. Clint’s companies don’t just have customers. They have superconsumers who bring him into every new company they join. That’s what happens when you help someone win.The financials are the score, not the strategy. Everyone reads the P&L to see what already happened. Clint asks: “How did we play? What will we do differently next time?” Strategy predicts the score. The score doesn’t predict strategy.This isn’t theory.Clint’s made investors rich. He’s made employees rich. But most importantly, he’s made customers successful enough that they’ve built iconic businesses of their own.Traditional CEOs are terrified of AI because it threatens to expose what they don't actually understand.Clint’s excited because AI makes the job he’s always done easier.He doesn’t use AI to automate away jobs. He uses it to:Role-play with superconsumers before real meetingsTransfer decades of knowledge to new sales reps instantlyPay salespeople more because revenue per FTE goes upThe question isn’t whether AI will replace CEOs.It’s whether CEOs have been doing work worth keeping.If your strategy is “copy the competitor and optimize the P&L,” AI will do that faster than you. But if your strategy is about creating a category where your customer’s customer wins, AI becomes your unfair advantage.This is what we call the Agentic CEO—leaders who use AI to amplify judgment, not replace it. Want to go deeper? Read this mini-book:The Agentic CEO: How AI Agents Can Help A 1st Time CEO Become A Legendary CEOCategory Pirates 🏴‍☠️·Jan 2Read full storyHere’s what 27 years in the chair taught Clint:You’re not managing a company. You’re managing what’s in bounds and what’s out of bounds. What’s rewarded and what’s a no-no. That’s culture. And culture is the predictor of every financial outcome people obsess over.Good CEOs inherit culture and complain about it.Great CEOs inherit culture and design it.Clint designs companies where abundance is the strategy. Where helping customers win is the business model. Where taking price up isn’t extraction—it’s a reflection of the value you’re creating downstream.That’s why his customers stay with him across companies. That’s why his teams follow him into new categories. That’s why investors keep betting on him.Because the scoreboard always reflects how the game was played.And Clint’s been playing a different game all along.Every leader right now is making a choice: manage the scoreboard or design how the game is played. This conversation shows you what the second path actually looks like—and why it's the only one that survives AI.(And this summary barely scratches the surface of what we unpack!)Here’s how to navigate this conversation:01:09 – The Three Jobs of a CEO: Strategy, culture, and financial performance—and why most people obsess over the wrong one.04:17 – Operating Out of Abundance: How watching his father’s design firm in Seattle taught Clint that helping your customer win with their customer is the only sustainable business model.08:31 – Driven by Respect, Not Fortune: Why Clint’s motivation has always been respect first, recognition second, and financial gain third—and how that shaped his career.20:57 – Builders, Buyers, and Managers: The three types of CEOs, why none of them are bad, and how to align your talents with what the company actually needs.26:03 – Finding the Simple, Overlooked Problem: How Clint framed and claimed categories by solving problems competitors ignored—from dialysis office space to “three steps, 30 minutes, best skin in your life.”39:57 – The Meeting Cadence No One Talks About: Why rigorous Monday staff meetings, Friday huddles, and bi-weekly strategy sessions predict financial outcomes more than any P&L.49:18 – The CEO User Manual: How sharing your triggers, communication style, and blind spots accelerates trust and unlocks high performance from your team.1:13:18 – Taking Price Without Apology: The art and science of commanding premium pricing by creating value for your customer’s customer—not just your customer.1:22:39 – AI as Your Competitive Advantage: How Clint uses AI to role-play with superconsumers, analyze patterns, and transfer 30 years of knowledge to new sales reps instantly.1:27:37 – Building Your AI User Manual: Why the best results come from teaching AI about yourself the same way you’d build trust in any relationship.If you’re in the chair—or want to be...If you’re building companies, not just managing them...If you’ve ever wondered why some CEOs make everyone rich while others just survive...This conversation is your playbook. Not a template to copy. But a pattern to recognize. The scoreboard always reflects how the game was played. And 27 years in six different chairs taught Clint exactly how to design the game.Arrrrrrr,Category Pirates 🏴‍☠️Eddie YoonChristopher Lochhead This is a public episode. If you'd like to discuss this with other subscribers or get access to bonus episodes, visit www.categorypirates.news/subscribe

This is a public episode. If you'd like to discuss this with other subscribers or get access to bonus episodes, visit www.categorypirates.news/subscribeFor 30 years, books have been one of the only products in the world that haven’t increased in price.A hardcover business book in 1997? $27.A hardcover business book today? $28.Meanwhile:Gas, meals, and movie tickets have doubled.College tuition has tripled.Book publishers are making more money than ever.Where is all that value going?Not to authors. Because the traditional publishing system is rigged. And until now, no one had the courage to call the bluff and raise the price.This mini-book is both a battle cry and a blueprint.It’s for authors, thinkers, and creators ready to stop selling their brilliance for $30—and start commanding what their ideas are actually worth.Here’s what you’ll get inside:[00:01:06] – Why Book Pricing Makes Smart People Look Stupid: Books are one of the only modern products that haven’t kept up with inflation. Not because readers won’t pay more—but because authors never challenged the system. [00:08:10] – The Publishing House Always Wins—Even When You Don’t: Traditional publishers make money whether your book succeeds or not. They lean on old backlist hits, force authors to do their own marketing, and pay royalty rates that haven’t changed in decades. [00:15:23] – Business Books Are Outcome Products: A great business book isn’t entertainment—it’s leverage. It can land a new job, inspire a company pivot, or generate millions in downstream revenue. [00:22:38] – How to Reposition Your Book as a Premium Product: Pricing isn’t just a number—it’s a story. When you set a higher price, you teach people how to value your thinking. [00:29:51] – The $100 Book Is a Category—Not a Gimmick: This is the new frontier of intellectual capitalism. The smartest creators are no longer playing by the old pricing rules. This isn’t about gouging readers.It’s about finally telling the truth: your thinking is worth more than $30. Your book is an outcome—not a product.So price it like one.Arrrrrrr,Category Pirates 🏴‍☠️Eddie YoonChristopher Lochhead

This is a public episode. If you'd like to discuss this with other subscribers or get access to bonus episodes, visit www.categorypirates.news/subscribeMost companies calculate TAM like accountants. But Category Designers? They size it like visionaries.Because belief beats spreadsheets. And when you combine both? That’s how you unlock The Trillion Dollar Future.In this audiobook, you’ll learn how to:Avoid the traps that led McKinsey to underestimate mobile phones by 100xFuse math + belief to tell a credible story about exponential outcomesDeploy a fleet of 11 specialized agents to turn TAM into a living, breathing treasure mapWhether you’re designing your first pitch or preparing for a billion-dollar breakout, this playbook helps you stretch the ceiling of what your category could become—and back it up with real proof.Here’s what you’ll get inside:[00:01:06] – TAM Is Belief Disguised as Math: Most founders either underbuild their TAM (too spreadsheet-heavy) or overbuild it (too dreamy). The unlock? Supers. [00:04:42] – When Experts Are Too Smart to See the Future: In the 1980s, AT&T hired McKinsey to forecast cell phone demand by 2000. They guessed 900,000. The real number? 109 million. [00:10:00] – Find Hidden Growth in Adjacent Quests: Supers don’t just buy one thing. They buy in patterns. Your agent helps you map those adjacent categories—like Red Bull did with F1 and cliff diving.[00:13:19] – Maximize Your Existing Revenue: What if the next big unlock isn’t a new product—it’s one your supers haven’t bought yet? These agents help you spot partial buyers, missed bundles, and quest-aligned purchases to dramatically increase customer lifetime value.[00:19:03] – Would You Like Fries With That? McDonald’s turned a single line into a global revenue reflex. This chapter shows how to train an agent to find your “fries”—the high-leverage upsell that makes you more money and makes your supers happier.[00:22:04] – Lifequake Agents: Where Exponential Spend Hides in Plain Sight: Supers move faster through life-changing moments—births, deaths, moves, marriages. If you can spot the quake, you can predict the spend. [00:26:32] – The Living TAM Model That Grows with You: This simple math becomes exponential when you apply insights from the other 10 agents.Most people try to forecast the future based on the past.Category Designers build the future by listening to their supers.This is how you turn belief into math, and math into momentum.Arrrrrrr,Category Pirates 🏴‍☠️Eddie YoonChristopher Lochhead

This is a public episode. If you'd like to discuss this with other subscribers or get access to bonus episodes, visit www.categorypirates.news/subscribePeter Drucker defined the 20th-century executive but he never imagined fleets of AI agents.The Agentic Executive is a bold redefinition of modern leadership.\Not managing more people.Managing more agents.Because in the AI-first world, leverage is no longer measured in headcount.It’s measured in agent count.From scheduling and data analysis to entire strategic workflows—AI agents are atomizing, accelerating, and automating work that used to require entire middle layers of management.In this book, we show you why the old model is collapsing, how the smartest executives are adapting, and how to build the skillset that will define the next generation of leaders.Here’s what you’ll get inside:[00:01:02] – Sergey Brin’s AI Manager Moment: Google’s co-founder used Gemini to identify a high-performing engineer he never noticed in meetings. AI saw her. Promoted her. And reshaped Brin’s view of management forever.[00:02:20] – Why Drucker’s Model Was Right—And Now Incomplete: Drucker’s timeless advice—focus on contribution, strengths, and decisions—still matters. But in today’s companies, it’s been distorted into kabuki theater. [00:05:03] – The Managerial Pyramid Is Collapsing: 70% of employees would leave because of bad managers. Only 30% want to become one.[00:08:25] – AI Isn’t Taking Jobs—It’s Creating Exponential Value: PwC data shows a 56% wage premium for people with AI skills. Same role. Same title. Very different outcomes. [00:10:15] – How To Go From “I Do” to “Agents Do”: A new model of work is here.We break each step down with examples, frameworks, and tools for action.This isn’t a story about AI replacing people.It’s about amplifying those who know how to lead in a new way.Because in the future, the most legendary executives won’t be the ones with the biggest org chart. They’ll be the ones commanding fleets of agents to create massive results at scale.The Agentic Executive isn’t a role. It’s a category.Arrrrrrr,Category Pirates 🏴‍☠️Eddie YoonChristopher Lochhead

This is a public episode. If you'd like to discuss this with other subscribers or get access to bonus episodes, visit www.categorypirates.news/subscribeThe education system isn’t broken. It’s just training people for a world that no longer exists.This audiobook names a reality most parents, teachers, and institutions feel—but struggle to say out loud:We’re teaching Native Digital students with Native Analog systems.And the gap is widening.Native Analogs grew up in a world where digital tools were an add-on to real life.Native Digitals grew up in a world where digital is real life—and the physical world is secondary.That difference changes everything about how people learn, build skills, and create value.This isn’t a future problem.It’s a right-now problem.Here are a few key points:[00:00] - Native analog vs. native digital: There are two types of people - native analogs (Baby Boomers and Gen Xers) and native Digital's (Millennials and Gen Zs), with fundamentally different definitions of reality.[04:29] - Failure of traditional education: Native analog education is failing native digital students because it focuses on memorization rather than application of knowledge in a digital world.[20:50] - Atomization of education: Education is becoming atomized, with students seeking specific knowledge from category experts rather than broad education from generalists.[33:19] - Need for digital transformation: Native analog educators must completely rethink their approach, creating truly native digital learning experiences instead of just adding digital tools to analog methods.[42:38] - Tech companies in education: Major tech companies like Google, Amazon, and Apple are entering the education space, potentially competing with traditional institutions by offering career-specific certifications and learning programs.This audiobook isn’t anti-education.It’s anti-denial.Because the most dangerous move isn’t that kids are learning differently.It’s that adults keep pretending they’re not.If you’re a:Parent trying to do right by your childEducator who feels the system slippingFounder building learning, community, or creator platformsThis audiobook gives you language for what’s happening—and clarity on what to do next.The future of education is Native Digital.Arrrrrrr,Category PiratesEddie YoonChristopher Lochhead

This is a public episode. If you'd like to discuss this with other subscribers or get access to bonus episodes, visit www.categorypirates.news/subscribeChurn isn’t a retention problem. It’s a category problem.Most companies treat churn like a leak in the bucket: Lower the price.Add a discount.Send more emails.That doesn’t fix churn. It just attracts the wrong customers faster. This audiobook makes a sharper claim: if price is your retention strategy, you don’t have one.Serial Churners.They binge. They bail. They extract value without committing.And in a subscription-first world, they quietly destroy lifetime value, margins, and market cap.Churn isn’t solved by squeezing customers.It’s solved by redesigning the relationship.Here are a few key points:[00:00] - Netflix's success in attracting viewers with original programming is counterbalanced by the rise of "cereal Turners" - subscribers who frequently cancel services after binge-watching content.[08:34] - The subscription economy is growing rapidly across various industries, including streaming services, software, and even the automotive sector. This shift creates new challenges in managing customer churn.[17:59] - Companies can combat churn by implementing three strategies: tailored pricing using "good, better, best" tiers, creating non-obvious premium bundles, and building non-obvious business models that lead to radical mergers and acquisitions.[22:54] - The concept of "adjacent possible" can be used to create innovative bundles and partnerships that cater to both super consumers and cereal Turners, as demonstrated by the marketing campaign for the Barbie movie.[31:52] - Loyalty programs, like those in the airline industry, can create exponential value for companies by tapping into adjacent possibilities and creating new revenue streams beyond the core business.This isn’t about “keeping customers longer.”It’s about moving them up the intimacy curve: User → Subscriber → Member.When customers feel like members, they don’t churn. They belong.This audiobook gives you a fundamentally different way to think about growth.Not by fighting churn. But by making leaving feel irrational. Because the strongest retention strategy isn’t a discount.Arrrrrrr,Category PiratesEddie YoonChristopher Lochhead

This is a public episode. If you'd like to discuss this with other subscribers or get access to bonus episodes, visit www.categorypirates.news/subscribeGreat operators already know this in their bones: Complexity slows you down. Simplicity moves the market.When customers hesitate… When sales stall…When teams argue…When strategies drag…The problem is rarely effort. It’s friction. Simplicity isn’t dumbing things down.It’s making hard things easy to choose, easy to use, and easy to remember.This mini-book shows why simplicity is not a design preference—but a growth strategy.Here are a few key points:[00:00] - Simplicity is crucial for product success, as demonstrated by the failure of Google Glass due to its complexity.[03:30] - Simplicity speeds up company, product, and category growth by making things easier for consumers to understand and use.[09:55] - To simplify products and offerings, focus on making decisions easy for customers and reducing decision friction.[18:50] - Use simple, memorable language to describe your category, company, and offerings. Avoid jargon and use words that are easy to understand and share.[28:51] - Implement a simple decision-making framework, like the "One Way Door and Two Way Door" model, to increase business velocity and empower teams.This isn’t about doing less work.It’s about doing less that doesn’t matter.When the world is noisy—Simplicity is velocity.Arrrrrrr,Category PiratesEddie YoonChristopher Lochhead

This is a public episode. If you'd like to discuss this with other subscribers or get access to bonus episodes, visit www.categorypirates.news/subscribeRecessions don’t kill businesses. Fighting for demand does.When the economy tightens, most companies panic. They discount. They compete harder. They spend more to make less.And that’s exactly why they lose.This audiobook makes a simple but contrarian claim:Recessions are the worst time to chase demand—and the best time to create it.Customers don’t stop spending. They reorganize their priorities.Everything gets sorted into two lists:Must-havesNice-to-havesIf you land on the wrong list, no amount of marketing will save you.This mini-book shows you how to move categories, products, and services up the hierarchy of perceived value—so you’re not competing on price, discounts, or desperation.Here are a few key points:[00:00] - Recessions create two lists: must-haves and nice-to-haves. The key is to get your product/service on the must-have list by increasing perceived value.[07:20] - Create high-value non-obvious insights by auditing today's popular solutions to find emerging category opportunities and solve tomorrow's problems.[16:58] - Convert non-obvious insights into intellectual capital, then turn that into digital products, services, or businesses that can scale infinitely.[26:43] - Design new categories for your digital products/services, considering how to turn cost centers into revenue-generating opportunities.[26:43] - Market your new and different category to create net new demand by solving tomorrow's problems today, avoiding competition and thriving during recessions.This is not about waiting for the recession to end.It’s about using the recession to reposition yourself.Because when competitors are distracted by survival, that’s when category creators design the future.Now is no time to work on the incremental.Now is the time to design demand.Arrrrrrr,Category PiratesEddie YoonChristopher Lochhead

This is a public episode. If you'd like to discuss this with other subscribers or get access to bonus episodes, visit www.categorypirates.news/subscribeSchool taught you how to follow rules. This audiobook teaches you how to get paid.Most adults will tell you to:Get a “real” job.Work minimum wage.Wait your turn.Go to college.Figure it out later.That advice made sense in a world that no longer exists.This mini-book is written for Native Digitals—teenagers who already understand the Internet better than most adults ever will.And that’s not a weakness. It’s your unfair advantage.You don’t need permission to start a business anymore.You need:A laptop or phoneAn internet connectionAnd the courage to ignore outdated adviceThis audiobook doesn’t give you fake hustle porn or “get rich quick” nonsense.It gives you 18 real, practical ways teenagers are already making money—often by solving problems adults don’t even see.Here are a few key points:[00:00] - The book is aimed at helping teenagers build profitable digital businesses, encouraging them to take advantage of their native digital skills.[05:21] - Teenagers are advised to focus on digital businesses rather than analog jobs, due to higher profit margins and lower overhead costs.[15:19] - The book suggests various ways for teens to help local analog businesses adapt to the digital world, such as setting up e-commerce sites or managing social media.[24:15] The book proposes ideas for teens to monetize their skills and knowledge, like creating educational content or offering digital setup services.[41:26] - The book encourages teenagers to turn their interests and daily activities into business opportunities, such as curating content or leveraging personal data.Category PiratesThis isn’t about becoming famous.It’s about becoming independent early.Because if you can build even one small, profitable digital business as a teenager, you don’t just make money.You learn how to:Create valueNegotiate outcomesAnd design your future instead of inheriting someone else’sAnd once you learn that?You’re set for life.Arrrrrrr,Category PiratesEddie YoonChristopher Lochhead

This is a public episode. If you'd like to discuss this with other subscribers or get access to bonus episodes, visit www.categorypirates.news/subscribeA founder-level, no-spin look at how Category Pirates actually make decisions.Using data most companies would ignore, delete, or never think to collect.This isn’t a success story.It’s a below-deck audit.If you really believe in Category Design, you should be willing to run it on yourself.So we did.We surveyed our subscribers. We cross-referenced it with Substack data. We pulled Stripe data. And then we went hunting for weird signals.What we found changed how we think about:OutcomesSuperconsumersContentPricingAnd the future of Category Pirates itselfNot just what the data said—but how to think like a Category Scientist when the answers aren’t obvious.Here are a few key points:[00:00] - Category Pirates uses "category science" to analyze data about their product, company, and category to spot future growth opportunities and shape their future direction.[08:31] - Their survey revealed that 33% of subscribers are "all in" on category design, while 67% are "curious" and stay subscribed for an average of 5.2 months.[11:30] - The top 10 mini-books drive 59% of paid subscribers, indicating a need to focus on high-performing content.[18:27] - They identified five factors common to their top-performing mini-books: hyper-targeted audience, clear outcomes, robust frameworks/strategies, practical application, and effective marketing.[22:15] - Category Pirates is adjusting their content strategy to align with the five-factor framework and organize content by categories (executives, marketers, writers, entrepreneurs, etc.) to ensure subscribers get legendary outcomes.This is not a polished case study.It’s what happens when you:Ask “why?” seven timesRefuse to get defensiveAnd let your Supers tell you the truthIf you’ve ever wondered:Why some content compounds and some disappearsWhy some customers evangelize and others churnOr how to design strategy with your Superconsumers instead of guessingThis audiobook is your field guide.Because the future doesn’t belong to companies with the most data.It belongs to the ones brave enough to listen to the weird stuff.Arrrrrrr,Category PiratesEddie YoonChristopher Lochhead

This is a public episode. If you'd like to discuss this with other subscribers or get access to bonus episodes, visit www.categorypirates.news/subscribeVery few companies are actually category creators.This mini-book isn’t here to inspire you.It’s here to score you.Using real data from the fastest-growing companies in the world, the Category Design Scorecard answers one uncomfortable question:Are you building the future—or fighting for scraps in the present?Because from the outside, high-growth companies can look the same.Inside, they’re wildly different.Nearly every company falls into one of three buckets and only one of them actually wins long term.This audiobook walks you through a brutally simple diagnostic that separates companies into three types:Be the Winner – obsessed with market share and competitionBe the Best – obsessed with products, features, and being “better”Be Different – obsessed with creating a new category altogetherMost companies never make it past the first two.And the data shows why that’s a problem.The scorecard was built by analyzing real companies—10Ks, investor decks, annual reports—and grading them across five Category Design dimensions that actually predict long-term value.Here are a few key points:[00:00] - The Category Design Scorecard is introduced as a tool to evaluate companies' ability to create and dominate new market categories, assessing them in five key areas on a 0-2 scale.[03:37] - Companies are categorized into three groups based on their scores: "be the winner" (0-2), "be the best" (3-5), and "be different" (6-10), with "be different" companies showing the highest stock price growth.[06:37] - The book discusses how category neglect can lead to the downfall of even dominant companies, using Intel as an example, and emphasizes the importance of continuous category innovation and reimagination.[09:12] - "Be the best" companies focus on having the best product or technology within an existing category, but this approach may not be sustainable in the long term.[11:37] - The book explains how "be different" companies create new categories and subcategories, using the example of e-bikes to illustrate how this approach can revolutionize an entire industry.You’ll also see why incumbents almost never spot new categories early—and why that blind spot is structural, not accidental.This isn’t about marketing.It’s about relevance.Because the Scorecard doesn’t just tell you what kind of company you are today—it gives you a clear signal of whether you’ll matter ten years from now.If you’re a founder, executive, investor, or operator who wants an honest read—not a hype deck—this audiobook will change how you see companies forever.Once you see the three buckets, you’ll never confuse growth with leadership againArrrrrrr,Category PiratesEddie YoonChristopher Lochhead

This is a public episode. If you'd like to discuss this with other subscribers or get access to bonus episodes, visit www.categorypirates.news/subscribeNetflix doesn’t have a content problem. It has a category problem.Everyone thinks Netflix’s next move is obvious: More shows.More IP.More gaming.This mini-book argues something far more uncomfortable:Gaming isn’t Netflix’s future. Creators are.And whoever figures that out first will own the next decade of storytelling.This is not a cheerleading piece for Netflix.It’s a Category Lens teardown of what’s actually happening in media—and why the biggest threats to Netflix don’t look like Disney or HBO.They look like:YouTubeTikTokMrBeastAnd a generation that never grew up with “TV” at allWhat happens when Hollywood isn’t the center of storytelling anymore?Netflix won the last war by inventing binge-worthy streaming and original content.But that category is maturing.And when categories mature, the rules flip.Here are a few key points:[01:29] - Netflix announced plans to offer gaming products on its streaming platform in 2021.[14:46] - YouTube is bigger than Netflix, with over 2 billion monthly active users compared to Netflix's 214 million subscribers.[21:41] - Netflix should focus on signing digitally savvy, independent talent rather than just legacy talent.[33:26] - Netflix could become the next legendary film school, offering online certifications in filmmaking and related skills.[38:43] - The next generation of creators are digital natives, and Netflix should build an incubator for these emerging video creators to stay ahead.This mini-book isn’t about Netflix.It’s about the next giant film category.And the uncomfortable truth that whoever builds it first will make everyone else look old.Arrrrrrr,Category PiratesEddie YoonChristopher Lochhead

This is a public episode. If you'd like to discuss this with other subscribers or get access to bonus episodes, visit www.categorypirates.news/subscribeGreat ideas don’t scale by accident. They scale because they’re engineered to.Part I showed you why most books fail before they’re written.This mini-book shows you how to design one that doesn’t.If Part I is the diagnosis, Part II is the blueprint.This is where Category Design meets execution. Most books die because the author never decided what kind of problem they’re solving—or who the book is actually for.This audiobook gives you the missing framework. And once you see this lens, you can’t unsee it. Here are a few key points:[00:00] - Choosing scalable categories for business books like personal development, personal finance, insights/thinking, leadership, case studies, or relationships. Deciding on an idea-centric or author-centric approach.[08:17] - Presenting non-obvious solutions to obvious problems can increase shelf life by being surprisingly different, but these solutions may quickly become conventional wisdom. [17:56] - Titles and subtitles that educate on non-obvious problems people don't realize they have can result in longer-lasting category dominance if the solutions provided are actionable.[26:16] - Crafting titles that are clear rather than clever, signal the main benefit, and put the right descriptive words in potential readers' mouths to spark word-of-mouth marketing.[36:14] - Inventing new words or modifying existing ones in titles can name and claim new categories if the book then defines the new term's meaning and differentiates the perspective.This mini-book is the instruction manual most authors never get.Because ideas don’t win by being smart.They win by being understood, repeated, and carried forward.Arrrrrrr,Category PiratesEddie YoonChristopher Lochhead

This is a public episode. If you'd like to discuss this with other subscribers or get access to bonus episodes, visit www.categorypirates.news/subscribeArrrrr! 🏴‍☠️ 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!

If your career plan makes sense on paper, it’s probably holding you back.Legendary careers are built through side quests, curiosity, and the courage to follow signal.That’s how you end up somewhere interesting.In this episode, we turn the mic toward Bri Clark—the person who recently stepped into the role of Head of Operations for Category Pirates—to share how she thinks, how she works, and why she keeps making herself impossible to ignore.You may know Bri as the one who:Turned Shopify into a direct publishing engine for Category PiratesKicked off and is supporting this year’s Academy cohortHelped launch our Founding Subscriber tierBut this conversation isn’t about her work at Category Pirates or all the lifetimes Bri has lived—from paragliding and diving to working remotely across six continents.It’s about what happens when someone learns to see systems early—and refuses to stay in roles that underuse that ability.Bri’s career only makes sense once you stop believing in resumes and start understanding how side quests compound.From wilderness therapy for teenage boys sent to the Utah desert when nothing else worked.To building and running nonprofit fundraising programs that moved communities and doubled outcomes.And designing and operating businesses for creators whose work reaches millions.Across wildly different environments, the same pattern shows up. Bri walks into complexity, spots what’s actually broken, and fixes the system instead of polishing the surface. Not by forcing outcomes. But by designing the conditions where outcomes become inevitable.That pattern showed up early.People told Bri she was “good at design.” What they were really responding to was judgment. She could connect identity, ideas, and expression into something coherent—and shape experiences that moved people to act.That became undeniable inside a nonprofit where she quietly took on far more than her role.She applied for a promotion for work she was already doing—and didn’t get it.Instead, she was asked to train the person hired above her and keep running the work.That was the moment the premise broke. There’s no upside to staying where your leverage is obvious—but unrecognized. The system caught up shortly after, and she was fired.What Bri could contribute had outpaced what the role was designed to hold.It exposed a gap between what Bri could see and what the system was built to reward.And once you see the gap that clearly, you don’t keep pretending it isn’t there.So Bri stopped trying to fix it from the inside and went all-in on her own business.Where she rejected the next default moves:She didn’t cold email.She didn’t polish a résumé.She didn’t wait to be discovered.She told the truth in public.She published a candid teardown of one of the most well-known photographers’ websites—what wasn’t working, why it mattered, and how it could be better. He reposted it to over a million followers. Leads followed immediately.Not because she asked, but because she made her value visible.(Categories don’t get designed by people who stay quiet! 🏴‍☠️)That moment wasn’t reckless. It was precise. And it revealed a repeatable pattern.Be a SuperconsumerSay the thing everyone else avoidsDo it with care—and convictionThe response from telling the truth in public made it clear: the fastest way to stand out is to say what everyone else is avoiding.People weren’t looking for another designer to push pixels or apply a prettier template.They wanted someone who would sit with the mess, tell them what wasn’t working, and help translate who they actually were into something the world could understand. They didn’t want decoration. They wanted interpretation.They wanted someone willing to say, “This part doesn’t work. This part does. And here’s why.”That’s when Bri’s business took shape.Today, that work lives inside By Breezy—a category-driven web and brand design studio for creators who don’t need another template, but someone willing to think with them and tell the truth.Bri doesn’t get hired to make things look good. She gets hired when founders don’t know what they want—or why what they have isn’t working.That’s why her clients tend to be creators, thinkers, and operators whose work reaches millions and why the work compounds long after the site ships.That ability—to diagnose, orchestrate, and accelerate outcomes—has been the throughline of Bri’s career long before she ever heard the words Category Design or Lightning Strike.This episode isn’t about ranting for attention.It’s about rejecting the default.When Bri roasts a website—or a broken assumption—she isn’t attacking people. She’s attacking the status quo. She’s naming the invisible problem that keeps smart work from compounding.Because the real risk isn’t telling the truth—it’s pretending not to see it.That’s why she’s now helping steer the Pirate Ship.And why this conversation matters if you’re building a career, a company, or a category that doesn’t fit neatly on paper—but works in the real world.Here’s how to navigate this conversation:00:00 – From Native Analogs to AI Wheelchairs: How Category Pirates evolved its operating rhythm to move faster without losing judgment.02:29 – Paragliding, Risk, and Signal: How Bri’s appetite for risk and side quests shaped how she approaches work, decisions, and momentum.06:29 – The Push Off the Cliff: Getting fired, getting denied unemployment, and why relief—not panic—was the dominant emotion.08:01 – Training Your Replacement: The promotion she didn’t get, the six months spent onboarding the hire above her, and the moment the premise broke.10:22 – Wilderness Therapy in the Utah Desert: What working with teenage boys for 8–12 weeks taught Bri about leadership, discipline, and human systems.12:46 – The $1M Fundraising Outcome: How “being good at design” was really about orchestrating emotion, flow, and outcomes—not aesthetics.18:04 – Why Young People Feel Stuck: Bri’s POV on courage, curiosity, social capital, and why degrees without signal leave people frozen.22:01 – Backed Into a Corner: Running out of runway, hitting the end of savings, and why desperation often precedes clarity.23:17 – The Website Teardown: Roasting a legendary photographer’s website, why he loved it, and how radical honesty became a Lightning Strike.26:54 – Making Yourself Undeniable: Why resumes don’t work, why sales calls felt wrong, and how public truth-telling created inbound demand.29:25 – When Success Creates Burnout: Dozens of leads, record income, and the realization that the wrong clients can kill momentum.33:26 – The Advisor Trap: Spending $25K on “integrative coaching,” learning the cost of generic advice, and reclaiming personal agency.37:02 – Rejecting the Sales Call Premise: Why Bri refused manipulative selling, and how “no-sell selling” fit her superpower.41:05 – Radical Self-Responsibility: Owning the wins, the debt, the mistakes, and why that mindset compounds faster than blame.48:54 – Ranting as Evangelism: Why roasting isn’t cruelty, it’s missionary work—and how naming invisible problems unlocks outcomes.52:57 – Web Design as a Trojan Horse: Why the real work isn’t pixels or templates, but helping founders figure out who they are and what they want.1:00:17 – Raising the Bar While You’re Young: Why reduced expectations are the real enemy—and why 27 is the perfect age to do legendary work.1:03:26 – From Side Quests to Category Leverage: How following what you can rant about leads to POV, demand, and a career that compounds.This episode isn’t about web design. Or operations.Or even entrepreneurship.It’s about learning to trust what you see.About paying attention to the things that bother you, the systems that don’t make sense, and the moments where your contribution outgrows the role you’re in. Bri’s story shows what happens when you stop dismissing those signals—and start building around them.Not louder.Not faster.Just more honestly.To connect with Bri:Follow her on LinkedInCheck out her studio, By BreezyArrrrrrr,Category Pirates 🏴‍☠️Eddie YoonChristopher Lochhead This is a public episode. If you'd like to discuss this with other subscribers or get access to bonus episodes, visit www.categorypirates.news/subscribe

It takes a ton of courage to tell one of the largest publishing houses on earth:“No thanks.”But Paul Millerd did exactly that on a call with Penguin.He built a different path for himself when writing and publishing The Pathless Path. One with sovereignty instead of gatekeepers. Ownership instead of permission. And pricing designed for value, not for volume.This Creator Capitalist podcast is about a high-agency career reinvention.Paul rejected the premise that authors must trade their lifetime rights for a one-time check. The premise that you must shrink your ambition to fit an industry built on scarcity. The premise that “books don’t make money.”But at the start of his career, Paul followed the default prestige treadmill path.He went to grad school at MIT, then worked at McKinsey and BCG. But at 32, he was burned out. He had a moment of uncomfortable clarity when none of it felt like his path. That clarity pushed him to write, then to Substack, and eventually to a level of creative agency the default path could never offer.He stopped letting prestige define his life.As he told Pirate Eddie, his first real identity shift wasn’t quitting consulting.It was admitting (publicly) that he had something to say.He started publishing on Quora and LinkedIn. He shared essays about uncertainty, agency, fear, joy, and the hidden emotional cost of achievement. Every post was another step away from his old identity toward his new one.Paul wrote because something inside him refused to shut up.When he finally published The Pathless Path, it became a compass for thousands of people who wanted a life beyond résumés, credentials, and corporate suffering.Then came the plot twist.Penguin reached out with a six-figure offer for The Pathless Path, plus a second book.* $70,000 for The Pathless Path* $130,000 for a second bookNinety-nine out of a hundred authors would say yes to this deal.Paul said no because the deal required:* Giving up lifetime rights* Removing the book from print to redesign it* A royalty structure designed for the publisher, not for PaulHe realized traditional publishing wasn’t offering him a future. It was asking him to sacrifice the one he was already building. And the moment he pushed back and countered with a fair valuation, the room went cold.The old model couldn’t compute an author with courage.So, Paul walked.The $100 Book: Rejecting The Premise, AgainRejecting the Penguin deal was the spark that led to Paul’s $100 book Lightning Strike.Paul released a $100 premium hardcover edition—an art object and collector’s piece of the Pathless Path. He sold 250 copies in the first two weeks and has now shipped books to over 22 countries. Just like Taylor Swift reclaimed ownership of her masters, Paul reclaimed ownership of his words. And readers rewarded the courage.As Eddie told him during the jam:“FU money isn’t the freedom to walk away. FU skills are the freedom to create outcomes no one else controls.”Paul has FU skills.His $100 book is just one proof point of a major category shift.The future of books belongs to authors who understand pricing, packaging, and category design.Paul is doing what innovators always do:* Shrinking the distance between creator and reader* Designing a book as an experience, not a commodity* Monetizing with gross margins publishers can’t offer* Experimenting with bundles, merch, and extension products* Treating books the way musicians treat albums: constant creation and connectionA $100 book is just the initial momentum to begin building a different book category. This is the same wave pushing us Pirates to sell $100 books with bundled digital assets. It’s the same wave we’re seeing other independent authors ride to control their work and careers.It’s one of the first steps to becoming a Creator Capitalist.Here’s how to navigate this conversation:* 01:23 – Paul’s Pathless Pivot: From McKinsey and BCG to discovering the creative instinct that refused to be quiet.* 05:00 – Writing Before You’re “A Writer”: How publishing anonymously on Tumblr and Quora became the early writing reps that built his skills and courage.* 09:35 – The Vulnerability of Publishing on LinkedIn: Why the scariest part wasn’t the writing—it was admitting he cared.* 20:00 – Rejecting Penguin: The six-figure offer and the six-figure reasons it didn’t make sense.* 22:56 – Designing the $100 Book: Why Paul treated the edition as an art project, why it worked, and the details of how he created the book.* 37:07 – Creator Economics vs. Publisher Economics: Understanding margins, shipping, fulfillment, and why independence creates freedom.* 43:50 – The Power of Superconsumers: Why gifting behavior (buying 5, 10, even 20 copies) is the unlock for author growth.* 51:57 – Substack, Identity, and the Next Chapter: What Paul is building next and why creator-led publishing is just getting started.If You’re An Author, Pay AttentionPaul’s story marks a before/after moment for the book category.* Before: You needed publishers for credibility, distribution, and economics.* After: You need publishers for… what, exactly?As an author, you can keep your rights, financial upside, autonomy, and the connection with readers that publishers desperately wish they had. You can own your work. And you can experiment with formats, bundles, pricing, community, and autonomy.This is the new publishing strategy.It will be led by authors with courage, clarity, and a category of their own.Arrrrrrr,Category Pirates 🏴‍☠️Eddie YoonChristopher LochheadKatrina KirschP.S. — Ready to design your category-of-one career?We recommend starting with the following mini-books: This is a public episode. If you'd like to discuss this with other subscribers or get access to bonus episodes, visit www.categorypirates.news/subscribe

Ian Roberts spent his life becoming a creative.He built his career the Native Analog way, spending 25 years teaching painting workshops in Provence, France. He mastered the craft of composition and learned what makes a person come alive when they create. He’s also sold 60,000 copies of his book, Mastering Composition, a subject almost no one else had the courage to claim.Then, at an age when most people start winding down their careers, Ian pivoted.* He moved his in-person painting workshops online.* He built a thriving Mighty Networks community.* He grew a 200,000-subscriber YouTube channel.Ian never set out to become an online educator or a creator.He was trying to protect the one thing he couldn’t give up—painting.In this conversation with Ian, we explore the questions every creator eventually faces:* What happens when the thing you create becomes the business that consumes it?* How do you keep your soul intact when your creativity becomes your income?* What do you do when your next chapter demands a different version of you?Ian doesn’t sugarcoat his story. He tells the truth that only someone with decades in the trenches can tell.You’ll hear how:* Composition became his category. While the art world obsessed over brushes, color, and technique, Ian claimed the foundational problem no one else would touch: If you don’t understand composition, nothing else works. This insight turned his teaching into a category of one.* Teaching unlocked his superpowers. Decades of workshops sharpened his ability to simplify the complex, turn philosophy into practice, and speak with a calm authority. He explains the importance of teaching in his career and work.* YouTube became his ideal channel. Ian didn’t grow by chasing algorithms. He grew because he gave away everything he knew freely, generously, and without holding back. That generosity built a movement of Superconsumers.* Success created a new dilemma. He built a thriving business that pulled him away from the very thing that made him successful. Ian shares how he’s now unwinding the machine he built so he can return to the studio and find out what the next version of him wants to say.* In his 70s, he’s redesigning. Ian doesn’t believe in retirement. He believes in Dharma—the calling that owns you, the thing you can’t not do. Painting owns him. And he’s making space for the work only he can create.This episode is about art. But it’s also about identity, longevity, and the courage to pivot your life when the world thinks otherwise. It’s about how to own your category of one by following your instinct.And it’s a masterclass in how to build a career around what won’t let you go.Here’s how to navigate this conversation:* 00:45 – How a painter accidentally built a digital empire: Why Ian’s workshops in Provence, France, became the start of his online teaching business.* 04:29 – The composition category: How Ian discovered the foundational problem no one else in the art world was solving and turned it into his niche.* 10:48 – The YouTube flywheel: Why giving away everything he knew created more demand, more trust, and more freedom.* 18:15 – Creativity vs. content: Ian shares the tension every creator faces: When does “content” stop being creative and start being a cage?* 25:10 – The decades that prepared him: Why nothing in life is wasted. Every workshop, every student, and every brush stroke became Intellectual Capital.* 38:24 – The pivot at 73 years old: Ian’s honest reckoning with time, purpose, and the need to redesign the life he wants next.* 49:12 – Calling, craft & dharma: Why some work owns you forever, and why that’s a gift, not a burden.If you’re a creator…If you’re building a career around what makes you different…If you’ve ever wondered how to stay true to your craft while scaling your business…Ian’s story is a call to pay attention to the thing inside you that refuses to quiet down. It shows what happens when you follow the thread of your own curiosity long enough that it becomes the fabric of your life. Most importantly, it’s a wake-up call.Your work will evolve.Your interests will shift.But your calling will keep knocking until you answer it.Arrrrrrr,Category Pirates 🏴‍☠️Eddie YoonChristopher LochheadKatrina KirschP.S. — Ready to jam on your category idea?If you’re validating your ideas and want help Languaging your category, upgrade to the Founding Subscription. You’ll get access to Pirate Eddie Bot to pressure-test your POV, as well as the entire Category Pirates library of podcasts, audiobooks, and mini-books.👉 Upgrade here to start jamming with the Pirate Eddie Bot. This is a public episode. If you'd like to discuss this with other subscribers or get access to bonus episodes, visit www.categorypirates.news/subscribe

When a business spirals, it rarely happens because demand disappears.Often, it’s because the economics were rotten long before anyone noticed. Revenue masked it. ROAS disguised it. “Growth” rationalized it.And everyone inside the company is too siloed, rushed, or optimistic to ask the question that matters:Is this business creating or destroying value?The answer is directly connected to the contribution margin. But for most DTC companies, nobody owns that metric.* Not the CFO, who assumes marketing is handling it.* Not marketing, who assumes finance is modeling it.* Not the agencies, who only report ROAS and call it a day.* Not operations, who assume the margin issues are someone else’s fault.That unclaimed (and valuable) niche is where Thomas Parrott built his category.But a year ago, he was planning a different direction.When Thomas first entered the Category Design Academy, he thought his category was helping U.S. brands expand into Europe. He had decades of experience running DTC operations in the U.K., Europe, Australia, and the U.S. He knew international markets, had operational excellence, and could run launch playbooks.But there was a deeper pattern Thomas hadn’t named yet—something more specific than expansion, logistics, or operations.Something he’d practiced his entire career, without realizing it was his leverage.His breakthrough came halfway through the Academy, during a jam session where everything snapped into place. Thomas described the recurring problem he kept finding inside companies:Financial misalignment at scale.Eddie pushed him to say more. Christopher poked at the root cause. And then Thomas said it out loud:“They want to grow, and I help them grow profitably.”Thomas’s category wasn’t “U.S. to U.K. expansions.” It was “contribution margin architecture.” His superpower is diagnosing the financial truth that many businesses ignore and fixing it, so growth creates value instead of destroying it.Once he named it, his sales cycle transformed from 30+ weeks into 30 minutes.He simply said what he did, with clarity and confidence:“I fix contribution margin so companies can grow without blowing themselves up.”Companies leaned forward when Thomas shared his POV, because contribution margin is the number nobody owns but everyone feels.* It’s the t-shirt that gets returned seven times and loses money by the third.* It’s the operational lag that eats the margin before the product ever ships.* It’s the loyalty program that gives away entire orders without anyone noticing.Thomas has helped companies solve this problem for decades, across QVC, live shopping, Big Book Mail Order, global infomercial launches, and DTC operations on multiple continents.That history became his unfair advantage, and the patterns became his category.Contribution margin became the problem only he could frame, name, and claim.Today, Thomas works with large organizations where misalignment gets expensive fast. He’s hired to diagnose the problem, design the financial architecture, and oversee the team required to fix it (this often includes the super-ding-song consulting firms).If you want to understand DTC economics or see why so many companies “scale” their way into oblivion, this conversation will change how you think.You’ll walk away from this episode knowing:* Why ROAS (Return on Advertising Spend) misleads companies more than it helps them* How contribution margin reveals the truth about your business* Why operational excellence is a profit engine disguised as “back office”* How naming a niche problem can collapse your sales cycle from months to minutes* Why companies now hire Thomas to run the consulting firms they used to defer to* How a clear POV can transform your career, your identity, and your outcomesThis conversation is about reframing value through a category design lens. Most importantly, it will inspire you to step into the category you were always meant to lead.Here’s how to navigate the conversation:* 00:00-7:53 – From DTC Operator to Margin Growth Architect. Thomas shares how he reframed his expertise into a category that companies instantly understood. He also explains why financial misalignment hits hardest inside public companies with small, messy DTC divisions.* 09:24 – The Moment the Category Appeared. Why niching down made the problem Thomas solves bigger, more urgent, and more valuable.* 11:00 – Contribution Margin: The Unclaimed Number. How Eddie and Christopher pressure-tested Thomas’s POV until the category snapped into place.* 13:36 – The Infomercial Advantage. How decades of seeing real economics up close created Thomas’s instinct for margin architecture.* 19:23 – ROAS Is the Great Illusion. Why ROAS is a vanity metric that conceals more than it reveals, and how it quietly steers companies off a cliff. Thomas breaks down how he exposes the profit leaks nobody inside the company is tracking.* 25:46 – The T-Shirt That Changed Everything. The early lesson from Big Book Mail Order that taught Thomas how to analyze contribution margin from the ground up. And the beauty brand that didn’t realize entire batches of orders were being shipped at a loss.* 45:29 – The Epiphany That Rewrote His Career. How a single conversation, spoken with category clarity, collapsed his sales cycle overnight.* 56:11 – The View From the Top of the Value Stack. Why Thomas now oversees the global consulting firms that companies once relied on, and what that says about category power.* 01:07:33 – ROI of the Academy. How Thomas earned back the entire cost of the Academy in half a month. And why category clarity attracts opportunity and eliminates the need for “pipeline stress.”Thomas didn’t set out to be the Category King of contribution margin. He became it the moment he realized the number nobody owns is the one that matters most. He simply stepped into his superpower to solve that problem for others.You can connect with Thomas here.Arrrrrr,Category Pirates 🏴‍☠️Eddie YoonChristopher LochheadKatrina KirschP.S. - If you’ve ever struggled to explain what makes you different…Or wondered why your expertise doesn’t command the price, respect, or clarity it should, Thomas’s story is a reminder of what happens when you frame, name, and claim the problem. He became valuable by telling the truth about what drives profitable growth.That’s the power of category design and a compelling POV.If you’re ready to make the same leap, you can join the waitlist for the next Category Design Academy cohort (starting May 2026) here. This is a public episode. If you'd like to discuss this with other subscribers or get access to bonus episodes, visit www.categorypirates.news/subscribe

Walk into any boardroom today, and you’ll feel the quiet unease of leaders trying to make sense of artificial intelligence. Most companies are racing to adopt AI. But few are asking an important question: Who’s governing it?If CEOs will soon manage more AI agents than employees, governance becomes the single most important capability a company can build. Sue Barsamian helps businesses build toward that future.Sue is one of Silicon Valley’s most respected board members.She serves on the boards of Box, Five9, Gen Digital (formerly Symantec), and more. Earlier in her career, she worked with Pirate Christopher to pioneer the Lightning Strike strategy that reshaped how technology companies go to market. Today, she’s known as The Velvet Hammer—a leader who delivers extraordinary results while maintaining her humanity.Sue has spent her career helping leaders turn complexity into clarity. And an urgent challenge she’s seeing is how we choose to govern AI.Too many boards treat AI like a quarterly agenda item. It’s something to monitor, not master.But when anyone in a company can create a ChatGPT account and spin up an agent that makes decisions, connects systems, and acts autonomously, the old governance model collapses. Oversight alone won’t protect a business. What’s needed is a new category of literacy where every leader understands not only what AI can do, but how to direct it responsibly.Governance can no longer be about saying “no.” It must become the discipline of enabling “how.”Sue believes the next generation of Category Kings won’t be those who adopt AI first. They’ll be the ones who govern it best.At Box, for example, every employee is certified on AI. People are building agentic workflows, competing in hackathons, and automating everyday tasks across departments. HR won one of the internal competitions. That didn’t happen by accident. The company treats AI fluency the way it once treated financial fluency. It’s a baseline skill for every role.Beneath that initiative is a governance process modeled after software development. Every agent or workflow goes through its own lifecycle (proposed, reviewed, validated, and monitored) before it touches production data.Committees are also evolving at the board level.Sue says technology and cyber oversight are now discussed alongside audit and compensation. It reflects how strategic AI has become. It’s not a compliance exercise. It’s a system for continuous learning that lets the company innovate without losing control.Innovation that scales because it’s governed, not in spite of it.You can’t lead what you don’t understand, and AI is forcing every leader to adapt.In a future where AI will handle more of the logic, leadership will be an art that requires more judgment, empathy, and connection.It will be less about commanding tasks and more about compounding relationships.Sue is an expert at striking a balance between the two.Her teams call her The Velvet Hammer because she demands excellence, but she delivers it with empathy. The people she has mentored over decades still follow her because she knows that performance and trust are partners. Results without relationships don’t last.In this conversation, you’ll discover:How AI is redefining governance as a source of capability, and why it will decide which companies win in the agentic eraThe inside story of how Sue’s boards are redesigning oversight for a world where bots outnumber employees, and how it changes what “risk” even meansHow boards can evolve to see technology and cyber risk alongside financial riskWhy Lightning Strikes remain the organizing principle of category leaders, and how Sue helped co-create the legendary Lightning Strike strategyWhat Sue has learned about leading with trust, rhythm, and responsibilityThe companies that thrive in the agentic era won’t be defined by how much AI they deploy, but by how much human judgment they preserve. Boards will need to understand algorithms the way they once understood accounting. And every professional, regardless of title, will have to think like a technologist and act like a teacher.This conversation is a call to every leader: AI alone won’t make your company legendary. You must direct it with clarity, courage, and compassion.(And enable your team to do the same.)Arrrrrr,Category Pirates 🏴‍☠️Eddie YoonChristopher LochheadKatrina KirschP.S. – Want to unlock the entire jam session with Sue?Sign up for a Founding Membership. You’ll instantly get access to this conversation, along with 35+ Founder’s posts, the Pirate Eddie Bot (your AI category designer), and the entire Category Pirates archive. It’s the perfect way to plan your category strategy for 2026! This is a public episode. If you'd like to discuss this with other subscribers or get access to bonus episodes, visit www.categorypirates.news/subscribe

Most companies see AI as a shortcut to efficiency.Fewer meetings. Fewer people. Fewer problems.But that’s an Obvious way to use AI.As the Head Coach of Outside In Leading and former HydraFacial Chief Talent Officer Deb Rodriguez explores the Non-Obvious application of AI:“If you’re only using AI to remove work, you’re missing the point. The future is about multiplying the people who create the work that matters.”Deb has spent decades building teams and turning companies into profit centers, like scaling HydraFacial from $40M to a public company worth billions.Her secret isn’t headcount.It’s human judgment.In this conversation with Deb, we explore what it looks like to codify that judgment in a world of AI agents—and how leaders can translate wisdom into systems that reason, coach, and make calls on their behalf.The result: Wisdom that scales you.Deb reveals a bigger truth we’ve been writing about for months.AI isn’t supposed to erase the work—it’s supposed to amplify the people doing it.But as Deb points out:We’re deleting the meetings where mentorship happensAutomating the feedback loops where judgment is developedDelegating decision-making to dashboards and calling it “progress”Most dangerously, we’re strip-mining the one thing we can’t replicate:People.Every business outcome starts with people.But people don’t scale easily, until now.Deb’s 555 Framework (5 outcomes, 5 metrics, 5 expectations) codified decades of leadership intuition into something teachable.She shows us what agentifying your intuition will look like: turning your logic, language, and leadership style into an AI system that can coach, reason, and respond like you.Not replacing humans with bots.But mirroring the best parts of human experience so that wisdom compounds.We jam on how every function (sales, finance, marketing, product, HR) will soon have its own fleet of agents:Agents that think like your top performers.Agents that coach your teams in real time.Agents that reason through complexity using your playbook.What Deb is doing for HR is what every executive will soon do for their department—turn experience into an exponential asset that compounds long after they log off.That’s leadership, at scale.Here’s what you’ll discover:Why most companies waste AI on time-saving instead of value-creatingThe mindset shift from managing people to multiplying peopleHow to think about cloning your own expertise into an agentic systemWhy the next generation of executives will be measured not by the size of their teams but by the power of their agentsHow to use Deb’s 555 framework to turn HR from a compliance function into a profit centerIf you lead people, build teams, or want to scale your own judgment, this conversation will change the way you think about AI—and how it will impact HR—forever.Here’s How to Navigate This Conversation00:00 – The Hidden Cost of “Efficiency”: Most companies aren’t short on tools—they’re short on judgment. You’ll learn why deleting “busy work” often deletes the very friction that builds mastery.07:42 – The Human Flywheel Inside HydraFacial: How a scrappy skincare company scaled from $40M to a billion-dollar IPO by investing in people first—and what Deb calls “making HR a growth engine, not a police department.”12:08 – The Myth of the Perfect Org Chart: Why most org charts are designed for control, not creation and how leaders can redesign roles around energy, outcomes, and ownership instead of hierarchy.19:55 – When People Become the Product: The turning point in HydraFacial’s growth story: how elevating employee experience directly multiplied customer experience, creating what Deb calls the “inside-out revenue loop.”24:33 – How to Build a Judgment Machine: Deb shares the real difference between data-driven and judgment-driven leadership—and why the best leaders teach people how to think, not what to do.27:05 – The AI Shift: From Automating to Agentifying: Why Deb believes the leaders of tomorrow won’t just use AI to save time. They’ll use it to scale themselves. Hear her forecast on how AI will evolve from assistant to advisor.35:40 – The People Multiplier Mindset: What separates managers who use tech to remove people from those who use it to multiply them, and why “wisdom at scale” is the new business moat.39:25 – Culture as an Operating System: Why the companies that will win the Agentic decade aren’t optimizing workflows—they’re programming culture. Deb unpacks how to make values executable and measurable, like code.42:55 – The Agentic Decade Ahead: We look forward to consider what happens when every company has a “clone bench” of digital agents trained on its best thinkers and what leaders can do today to prepare.If you’ve been wondering how to get ahead of the AI hype train without getting flattened by it, start here.Because in the decade ahead, wisdom will be the exponential resource. This is a public episode. If you'd like to discuss this with other subscribers or get access to bonus episodes, visit www.categorypirates.news/subscribe

When hundreds of companies were fighting for urban telecom towers, Melissa Andrews walked the other way.Instead of battling in the obvious market, she and her husband Tom went where almost no one was looking.The farm.Together, their first act was turning rooftops into telecom platforms when everyone else just saw buildings. That overlooked idea became a thriving business.But in 2019 they asked a different question:Why don’t farmers have the same connectivity as city dwellers?The answer became Connected Farms.Instead of fighting hundreds of telcos for urban market share, Melissa carved out a category nobody was paying attention to: agricultural connectivity.Most people fight to be an “ER” company. Better. Faster. Cheaper. The ambitious ones try to be the “EST.” Fastest. Smartest. Biggest.But Melissa? She chose to be different. Which made her the only.The only LTE provider in ag. The only ones putting Starlink on tractors. The only team building private networks under almond orchards and dairy sheds.She didn’t wait for a framework.Long before she ever heard of Category Design or joined the Academy, she relied on two instincts that everyone can practice:Curiosity: Keep asking “why” until you uncover a problem nobody else is solving.Empathy: Listen closely enough to hear the pain underneath the surface request.You don’t need to marry an engineer. You don’t need to stumble into the “perfect” market. You just need to pay radical attention to what frustrates people and be curious enough to keep pulling on the thread.That’s the part you can do today. Those instincts led her to the opportunity. But instincts alone can leave you wondering:Is this real? Can I repeat it? How do I explain it to others?That’s when Melissa joined the Academy. Not to learn curiosity or empathy—she already had those. But to get the language, the frameworks, and the confidence to take what she’d discovered and scale it.“The Academy gave me the frameworks and language to explain what we were already doing differently. That clarity is what turned our instincts into strategy—and strategy into growth.” - Melissa For Melissa, the Academy wasn’t about theory. It was about practice.She jammed with peers who poked holes, asked better questions, and forced her POV to get sharper.Out of those sessions came a phrase that changed everything: Digital Darkness.Two words that made the invisible pain of farmers instantly obvious. Two words that turned blank stares into “Oh, I get it.”That’s what happens when you stop circling around an idea and use Languaging.And the impact was immediate. Before, every conversation with a farmer was a long, slow education process. After? The timeline collapsed. Instead of months of explaining, she could move people from problem → solution → customer in a fraction of the time.Her pipeline didn’t just grow—it accelerated.What Melissa learned didn’t just apply to Australia and New Zealand. Or farming. Or even telecom.The frameworks she picked up inside the Academy transcend markets. They work across categories, industries, and geographies.Because once you can name the problem in a way no one else can, you don’t just win locally. You win globally. This is a public episode. If you'd like to discuss this with other subscribers or get access to bonus episodes, visit www.categorypirates.news/subscribe

This is a public episode. If you'd like to discuss this with other subscribers or get access to bonus episodes, visit www.categorypirates.news/subscribeSuper Consumers. Super Agents. Super Advantage.If you want to win in the AI era, don’t build for the average.Build for your supers. Then train your AI to think like them.In this mini-book, we reveal the future of category creation: AI Super Consumer Agents.The idea is simple but powerful. Your best customers already know what the future looks like.Now, AI lets you bottle their instincts—and scale them across your entire company.Instead of generic chatbots and obvious LLMs giving average answers, you can train narrow, purpose-built agents that pressure test decisions, identify new growth levers, and turn customer obsession into category domination.This is not about “using AI.”It’s about creating outcome-driven AI agents trained on the weird, wonderful, wallet-out instincts of your most loyal fans.Here’s what you’ll get inside:[00:01:00] – Lose Your Super Consumers, Lose Your Category: When Harley-Davidson hired a non-biker CEO, they didn’t just break tradition—they broke trust. The backlash was proof that supers are the brand. Ignore them and you don’t just lose relevance. You lose the whole damn category.[00:05:00] – Obvious AI Will Kill You Faster Than Harley’s CEO Did: Feeding generic customer data into AI creates “plausible mediocrity at scale.” If your inputs are average, your outputs will be painfully obvious—drop the price, make the logo bigger, copy the trend. Supers don’t want any of that. They want different, and they’re happy to pay for it.[00:09:00] – Most CEOs Spend More Time on the Toilet Than With Their Supers: Harvard data shows CEOs spend just 3% of their time with customers—only 0.3% with supers. That’s 11 minutes per week. Meanwhile, founders who are super consumers (like those behind Instacart and ThirdLove) build billion-dollar companies.[00:15:00] – AI Gives You 24/7 Access to Your Best Customers—If You Train It Right: Most companies still layer insights through agencies, surveys, and sanitized data. But AI changes that. You can now scale the unfiltered voice of your supers—every tangent, metaphor, and passionate rant—and use it to pressure test strategy, price changes, product ideas, and more.[00:20:00] – Your First Agent Should Be a Wizard of Weird: Before building a chatbot or customer service agent, start with the one that matters: a wizard of weird data. This agent isn’t just smart—it’s trained to think like your highest-value customers and see what others miss. This isn’t just an AI strategy.It’s Category Design x AI x Super Consumers—a new playbook for founders, CMOs, and execs who want to build the future, not react to it.And this is just part one.In the next mini-book, we’ll show you how to go from capturing existing super insights to uncovering brand new ones with AI—then turning those insights into a full team of agents across every function in your company.Because when AI thinks like your supers,You don’t just scale your business. You scale your category advantage.Arrrrrrr,Category Pirates 🏴‍☠️Eddie YoonChristopher LochheadKatrina Kirsch

This is a public episode. If you'd like to discuss this with other subscribers or get access to bonus episodes, visit www.categorypirates.news/subscribeArrrrr! 🏴‍☠️ 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!

This is a public episode. If you'd like to discuss this with other subscribers or get access to bonus episodes, visit www.categorypirates.news/subscribeMost marketing is broken.Not because teams are dumb or products are weak, but because the playbook is stale.Peanut butter marketing (marketing spread evenly across every platform) creates noise, not momentum. That’s why Category Designers don’t do campaigns. They do Lightning Strikes.This mini-book is your guide to designing a strike that makes the market move toward you—whether you’ve got $10K or $10M to spend.Inside, you’ll learn why great marketing isn’t about being everywhere. It’s about one explosive moment that rallies your team, gets your Superconsumers talking, and punches the category in the mouth.Here’s what you’ll get inside:[00:01:09] – Why Most Marketing Fails (And What to Do Instead). Traditional marketing calendars spread effort across too many channels with no clear POV. Learn why a Lightning Strike (a single, aligned, company-wide campaign) creates gravity, belief, and word of mouth on purpose.[00:07:08] – Outcome First: The High Note of the Strike. A Lightning Strike is only as strong as its outcome. Whether you need to save your business, challenge a Category King, or crown yourself as one, this chapter explains how to define the emotional, financial, and strategic outcomes that will rally your company and move your market.[00:11:02] – The Dumbest First Question You Can Ask. It’s not “How much should we spend?” It’s “What outcome do we need to create?” You’ll learn why Honda’s expensive, ineffective rebrand failed—and why belief, not budget, is what makes a strike legendary.[00:12:00] – The 5 Lightning Strike Types That Drive Word of Mouth. From Stunt Strikes to Culture-Creating ones, this section breaks down the five types of strikes that move the needle. You’ll see real-world examples from DUDE Wipes, Tesla, Janus Motorcycles, YC, Nike, and more.[00:30:39] – How to Match the Strike to Your Outcome. Strikes are not one-size-fits-all. This final section helps you choose the right strike based on your goal—and previews what’s coming next in Part 2, where you’ll learn how to plan and price your strike (whether you’ve got $10K, $100K, or $1M to spend).When it’s done right, a Lightning Strike doesn’t just drive leads. It rewires your company and redefines what your category believes is possible. Arrrrrrr,Category Pirates 🏴‍☠️Eddie YoonChristopher LochheadKatrina Kirsch

Most people think networking is about coffee chats and business cards.Pablo Gonzalez turned it into a $40 million outcome.In 2020, he helped a real estate company build a community that became the single biggest source of their client acquisition. In one year, the channel generated $40M in revenue.But here’s the twist: Pablo didn’t know if he could do it again.It wasn’t enough to win once—he needed to know he could win again.He had a superpower—building trust, connecting people, sparking digital word of mouth—but no framework to explain it, no category to put it in, and no guarantee it wasn’t a one-time fluke.That’s when Pablo joined the first-ever Category Design Academy cohort (our first-ever student!)And what he figured out is exactly what separates people who stumble into a big win from those who can create them on demand:Clarity of POV → Until you can name the problem only you can solve, your superpower looks like luck.Social validation at scale → It’s not enough for people to know you. The real growth engine is when people start telling your story for you.Financial + mental runway → If you’re carrying the wrong “pay for the party” costs, you won’t have the space to bet on yourself.For Pablo, learning to package his instincts as Intellectual Capital and design around his true superpower—relationship capital—was the unlock.The results?He went from “the guy who knows everybody” to Pablo the Connector—the King of Relationship Capital.His income 2.5X’d. His business runs without him. And now he’s Chief Evangelist for an AI company—a role he never thought possible.For Pablo, Category Design didn’t create his first $40M play.It made sure it wouldn’t be his last.In this conversation with Pablo, you’ll walk away knowing:Why social validation is more valuable than self-promotion (and how to earn it at scale)How to spot when a win is holding you back instead of pulling you forwardWhy financial + mental runway is the overlooked lever for creating career freedomHow to lower your “pay for the party” costs to create both financial and mental runwayHow to serve the people with the keys to the doors you want to openIf you’ve ever had a win but weren’t sure how to repeat it, or felt like your “soft skills” weren’t enough to scale, Pablo shows you how to turn those instincts into a repeatable career strategy.Here’s how to navigate this conversation:00:00 – “I never thought I’d be this guy”: Pablo shares how his business began running without him and why that felt impossible just a few years earlier.02:58 – The $40M Community Play: The behind-the-scenes story of how one community experiment turned into a $40M revenue channel during the pandemic—and why that success nearly became a trap.07:52 – Why Accidental Wins Aren’t Enough: Pablo opens up about the false confidence his early success gave him, and how the fear of being a one-hit wonder pushed him to search for a repeatable framework.10:06 – From Green Building to Community Building: From sustainability consulting to nonprofit events, Pablo retraces the unlikely career pivots that revealed his true superpower—unlocking value through relationships.13:50 – Pablo the Connector: How he earned a reputation for abundance, the deeper skill underneath “knowing everyone,” and why Christopher and Eddie crowned him the King of Relationship Capital.20:44 – Digital Word of Mouth: Why Pablo calls social validation the “nuclear reactor” of growth, how he creates it at scale, and the shift from being known to being talked about.23:13 – The Academy Unlock: What changed when Pablo joined the first Category Design Academy cohort, how sharpening his POV 2.5X’d his income, and the moment he realized his success wasn’t a fluke.26:53 – Runway Is Everything: The bold decision to leave Miami for Jacksonville, how lowering “pay for the party” costs gave Pablo both financial and mental freedom, and why most people overlook this lever.34:09 – POV in Practice: Pablo breaks down the framework he uses to turn instincts into Intellectual Capital—and how you can package your own “different” into something the market values.41:59 – From Connector to Evangelist: How Pablo’s category journey opened doors he never imagined—from community builder in Miami to Chief Evangelist for an AI company competing in Silicon Valley.Pablo’s story proves that one big win isn’t enough—you need a category to make it repeatable.The question is: will you keep chasing flukes, or design a career that compounds?To connect with Pablo:Follow him on LinkedInCheck out Pablo’s business, Be The StageJoin the Category Thinkers CommunityArrrrrr,Category Pirates 🏴‍☠️Eddie YoonChristopher LochheadKatrina Kirsch This is a public episode. If you'd like to discuss this with other subscribers or get access to bonus episodes, visit www.categorypirates.news/subscribe

Marketers think their job is to get attention.So they burn millions on “brand campaigns.” They measure impressions. They brag about reach. They smear peanut butter across every channel and call it strategy.And then they wonder why nobody remembers them 48 hours later.(Like the Sydney Sweeney ad the internet already forgot)Attention isn’t the goal. A cultural movement is.And nobody knows that better than Ryan Meegan, Chief Marketing Dude at Dude Wipes.They didn’t try to be the 9,000th toilet paper brand “raising awareness.” He went to war with toilet paper itself.What started as a joke between friends became a cultural strike. Suddenly, talking about your butt on national TV wasn’t taboo—it was funny, unforgettable, and impossible to ignore.“It wasn’t just about selling more wipes—it was about making it a cultural thing people would talk about.” - RyanThat’s not impressions. That’s a movement.Customers spread it. Retailers lined up for it. Competitors couldn’t wipe it away.Category Kings don’t market to be seen. They design Lightning Strikes that move the market from A to G.Most marketers stop at A. One splashy ad. One stunt. One Super Bowl spot. And then nothing.But legendary Lightning Strikes don’t stop at attention. They move people—step by step—through a sequence that ends in a cultural movement. A world where the market bends around you.That’s what Dude Wipes does.Each strike wasn’t random. Each was part of a deliberate framework. A system for making sure the market couldn’t look away—even if it wanted to.In this conversation, Ryan breaks down exactly how that system works.Why a $10K UFC gamble became the blueprint for Dude Wipes’ rise and what it teaches about risk, culture, and timingHow to turn a one-off stunt into a strike that compounds into culture instead of disappearing in 48 hoursWhy timing matters more than budget and how Dude Wipes decides when to pull the triggerHow to design WOM into your strike from day one so it scales whether you’ve got $10K or $10MWhy going to war with toilet paper was the real genius move, and how picking the right villain makes your strike unforgettableThis isn’t about ads. It’s about architecture. Ryan reveals the A→G framework behind every legendary strike—and how to turn your brand into the story culture can’t stop telling.Here’s how to navigate this conversation:00:12 – Betting It All on a Butt Sponsorship: Ryan shares how sponsoring Tyron Woodley’s UFC fight with almost their entire budget became Dude Wipes’ “revenue-or-die” moment.07:45 – When a Joke Becomes a Category King: How three friends riffing on a funny idea turned into a brand that went to war with toilet paper and why that villain gave them cultural firepower.13:28 – Fear Is the Signal of a Strike: Why the best Lightning Strikes feel reckless in the moment, and how that fear signals you’re about to bend culture.18:57 – Haters Make the Best Marketers: Ryan explains why backlash is a feature, not a bug—and how Dude Wipes uses critics to amplify word-of-mouth.24:40 – The Day Toilet Paper Became the Villain: The pivotal moment Dude Wipes reframed toilet paper as “making the problem worse,” and how that POV turned the category upside down.28:11 – The Power of the $50K Ceiling: Why their most legendary strikes have never cost more than five figures—and how constraints fueled creativity instead of limiting it.33:09 – When to Hold, When to Shove All-In: Inside Ryan’s sixth sense for timing deals, spotting fire-sale opportunities, and knowing when to bet big on a strike.41:40 – Protect Your Crease: The NHL campaign that proved the right copy can hijack culture better than a logo.47:12 – The Mount Rushmore of Lightning Strikes: From Jake Paul knockouts to butt-wiping footballs, Ryan walks through the most iconic strikes that defined Dude Wipes’ rise.50:57 – A Billboard Blitz Against TP: The inside story of a 700-billboard blitz that declared war on TP—and why it worked as a coronation strike cementing Dude Wipes’ place in culture.If you’ve ever wondered how a scrappy brand can hijack culture, outmaneuver giants, and turn bathroom humor into a billion-dollar movement—this conversation with Ryan is your north star.Arrrrrr,Category Pirates 🏴‍☠️Eddie YoonChristopher LochheadKatrina Kirsch This is a public episode. If you'd like to discuss this with other subscribers or get access to bonus episodes, visit www.categorypirates.news/subscribe

The world is hooked on short-form dopamine.They want quick hits of attention, likes, and external validation. But short-form dopamine fizzles out like fireworks: bright for a second, gone the next.Real creators trade quick highs for slow-burning joy that compounds over decades.They build lives around slow dopamine—the deep, sustaining joy that comes from making something meaningful. They lose themselves in the work. They taste what Monroe Jones calls “the bliss of self-forgetfulness.” And in the process, they create capital that compounds for decades.Monroe knows this path better than most.He grew up in small-town Mississippi. No trust fund. No silver spoon. No industry “in.” Just an obsession with sound. And even when he was broke—in the first decade of his career—he kept creating. He slept at the studio. He experimented. He learned the craft.That decade of invisible work became the foundation for everything that came later.Because the truth is: you don’t become a Grammy-winning producer by chasing hits. You get there by creating when nobody’s knocking on your door. By stacking unseen reps until the world can’t ignore you anymore.“What you have is not the thing that’s valuable. It’s what’s inside you. And that’s not depleted.” - MonroeThat obsession carried him to Nashville and L.A.—where he started working with legends like U2, Stevie Nicks, and David Crosby.But Monroe’s story isn’t about star power.It’s about something more practical—and more replicable.The mindset and practices that let him build a category-of-one career in one of the most cutthroat industries in the world.Radical creativity endures only when it’s grounded in generosity, identity, and purpose.Monroe’s story makes one thing clear: being a Creator Capitalist isn’t about chasing hits.It’s about designing a career that feeds your soul—where the work itself becomes the reward.And when you do that, you don’t just create music. You create enduring assets: Intellectual Capital, Relationship Capital, Reputation Capital, and yes, Financial Capital.In this conversation with Monroe, you’ll walk away knowing:Why slow dopamine is the real currency of creatorsHow generosity sets you apart in any industryWhat buildings and songs both teach us about Category Design Why creativity is never scarce and how to always access itHow your uniqueness is your greatest assetMonroe’s story proves that Creator Capitalists don’t just sell products or rack up credits. They create movements, shape culture, and find joy in the work itself.If you’ve ever questioned whether your work matters, this episode will prove that what’s inside you is never depleted—and that your unique stamp is the asset the world needs.Here’s how to navigate this conversation:00:07 – A Small-Town Beginning: Monroe shares how growing up in Mississippi shaped his obsession with sound and why the lack of a clear path was actually an advantage.09:47 – Architecture, Songwriting, and Design: The surprising parallels between buildings and music, and how universal design principles fuel creativity across disciplines.14:12 – The Decade Nobody Saw: Monroe opens up about his first ten years in the business—broke, making records nobody heard, and learning by doing. Why invisible work became the foundation for everything that came later.20:31 – Slow Dopamine in Action: Why creativity equals freedom, how to access the “bliss of self-forgetfulness,” and the reason real work compounds over decades.23:58 – Forrest Gump Moments: The serendipitous encounters and mentors that nudged Monroe’s career forward—and why being ready to say “yes” mattered more than having a plan.31:25 – Inside the Studio with Legends: Monroe takes us behind the scenes with U2, Stevie Nicks, and David Crosby—and the lessons only decades of collaboration can teach.49:39 – The Dark Side of Production: Stories of ego, conflict, and bad behavior in the studio—and why Monroe chose generosity and safety as the foundation of his creative philosophy.52:44 – Everyone Is Creative: The truth about why creativity is never scarce—and how to find and trust your own unique stamp.1:00:36 – Legacy and Identity: The story of a guitar Dwayne Eddy gifted Monroe, and what it really means to leave behind enduring capital.In the end, Monroe’s story is proof that the real wealth of a creative life isn’t the credits or the trophies—it’s the joy, generosity, and uniqueness that compound into capital no one can take away.Because when you build on slow dopamine, your work doesn’t just make noise. It makes history.To connect with Monroe:Connect with him on LinkedInCheck out his websiteFollow him on InstagramArrrrrr,Category Pirates 🏴‍☠️Eddie YoonChristopher LochheadKatrina Kirsch This is a public episode. If you'd like to discuss this with other subscribers or get access to bonus episodes, visit www.categorypirates.news/subscribe

When survival’s on the line, you stop chasing “perfect.”You stop worrying about looking polished.You stop giving a damn about what anyone else thinks.In June 2023, Nick Bennett lost his marketing director job.He had a nine-month-old at home, and a choice: play the traditional game (résumés, recruiters, 2,000-applicant job postings) or be different.He chose different.Survival mode has a way of sharpening your moves. For Nick, it came down to four:Get the first client fast: say “yes” to a problem you’ve never solved and figure it out as you go.Build a micro-tribe: surround yourself with people who open doors faster than any job board.Always be jamming: turn casual conversations into revenue by solving real problems in real time.Lean into signal: double down the moment the market tells you you’re onto something.Those moves triggered a chain reaction.And the dominoes started falling: casual DMs turned into paying work, deeper listening uncovered a hidden market for his skills, his micro-tribe opened doors cold pitches never could, and he co-led a launch that brought in $30K in a single weekend.“There’s no limit. If I did this once, I can do it again and again and again.” - Nick Today, Nick runs Full Stack Solopreneur and Harness & Hone, co-hosts the 1000 Routes podcast, and is living proof that the fastest way to de-risk your career is to stop playing someone else’s game.You’ll walk away from this conversation knowing:How to turn urgency into an unfair advantageThe four moves that transform one client into compounding momentumWhy the right kind of “free work” can be your highest-leverage playHow to build a micro-tribe that becomes your inbound pipelineThe fastest way to spot and act on market signalWhy buyer confidence matters more than your actual skill setThis episode is proof that when you act with urgency, you can build momentum so fast it becomes impossible to stop.Here’s how to navigate this conversation:00:00 - From Layoff to Leap: How losing his marketing director job pushed Nick into survival mode and why he refused to play the resume-and-recruiter game.06:44 - The First Client That Changed Everything: The unexpected “yes” that rewired his thinking about what was possible and set the dominoes in motion.13:18 - Finding the Hidden Market: How listening for unspoken problems revealed a more valuable niche.17:56 - Building a Micro-Tribe: The repeatable way Nick surrounded himself with door-openers.20:55 - Always Be Jamming: Why giving away your best ideas for free can be the most profitable move you make.26:47 - Podcasting as a Growth Engine: How Nick uses conversations to meet collaborators, refine IP, and expand reach.31:53 - From Idea to $30K Weekend: The inside story of a lean, trust-driven launch that outperformed without ads.37:56 - The Year-Long Collaboration: How patience, positioning, and partnership created a big payday.40:51 - No Perfect Time to Go Solo: Why waiting for the “right moment” is the surest way to stall your momentum.43:55 - Buyer Confidence vs. Skill: The overlooked principle that can turn an $8K month into a $50K month.If you’ve been waiting for the perfect time to bet on yourself, this episode will make you realize the perfect time is now.To connect with Nick:Connect with him on LinkedInListen to 1000 RoutesCheck out Harness and HoneSee Full Stack SolopreneurArrrrrr,Category Pirates 🏴‍☠️Eddie YoonChristopher LochheadKatrina Kirsch This is a public episode. If you'd like to discuss this with other subscribers or get access to bonus episodes, visit www.categorypirates.news/subscribe

This is a public episode. If you'd like to discuss this with other subscribers or get access to bonus episodes, visit www.categorypirates.news/subscribeFunnels are dead. Flywheels are the future.But most teams who try to build one stall out before it spins.Why? Because they treat it like a solo act—when in reality, the fastest flywheels are built by duos. A Native Analog. A Native Digital. And AI as the amplifier.This mini-book is your field guide to building a Marketing Flywheel that runs on belief, not brute force—one that compounds word of mouth, deepens loyalty, and scales your Supers without burning you out.You’ll learn the three steps to spinning a flywheel that doesn’t just work, it compounds. And you’ll get the exact AI prompts, bandmate roles, and behind-the-scenes stories from the Category Pirates crew that made our own flywheel go from push to perpetual.Here’s what you’ll get inside:[00:01:45] – Why Funnels Fail and Flywheels Win: Funnels bleed belief. Flywheels build it. The real reason most modern marketing dies on arrival—and how a belief-powered flywheel changes the game.[00:08:09] – Delight Your Supers With What You Already Have: The foundation of every flywheel is belief from your best customers. We show how AI, interns, and a pile of chaotic content turned into FAQs, tools, and daily value—without creating anything new from scratch.[00:16:04] – Map the Origin Story of Your Supers: If you don’t know where your most loyal subscribers came from—or what made them commit—you’ll never scale. We unpack how Pirate Eddie spotted three types of subscribers (Curious, Question, and Quest Pirates), and how Pirate Bri used that insight to create a high-converting, AI-powered onboarding flow.[00:23:25] – Automate and Accelerate Your Supers’ Quest: We show how Audrey and Julian built a custom quote engine to extract the most shareable lines from 100+ mini-books, how Pirate Jack helped automate it, and how AI turned content chaos into a daily WOM machine.[00:30:28] – What to Look For in an AI Bandmate (And How to Be One): Flywheels don’t spin solo. You need a native analog and native digital working in sync, amplified by AI. We give you the five traits to look for in each—and why collaboration, not code, is the biggest unlock for momentum.Flywheels aren’t about pushing harder. They’re about building with the right people—and letting AI make both of you better.Arrrrrrr,Category Pirates 🏴‍☠️Eddie YoonChristopher LochheadKatrina Kirsch

This is a public episode. If you'd like to discuss this with other subscribers or get access to bonus episodes, visit www.categorypirates.news/subscribeEvery legendary category starts by naming the problem only they can see. Then they plant a flag with a manifesto.A Category Manifesto is your movement’s founding document. Not copywriting. Not a positioning statement. It’s the emotional and strategic narrative that rallies your customers, unites your team, and reframes the market.In this mini-book, you’ll learn the 8-part manifesto framework we’ve used (and watched others use) to launch million- and billion-dollar categories. You’ll also see how to co-write it with your AI co-founder—whether you’re starting from scratch or pressure-testing a draft.Here’s what you’ll get inside:[00:02:18] – Why Every Category Needs a Manifesto: You don’t win by building a better product. You win by introducing a new worldview. How brands from Qualtrics to Clari used manifestos to name the problem, invite others into the solution, and ignite a movement.[00:08:36] – The 8-Part Framework for Manifesto Magic: From naming the enemy to defining the stakes, this is the playbook for writing a manifesto people believe in.[00:18:40] – What Great Manifestos Sound Like (And Why Most Fall Flat): The difference between a forgettable brand story and a rallying cry people can’t stop repeating.[00:25:12] – How to Co-Create Your Manifesto With AI: Skip the blank page. Use AI to help brainstorm, structure, and refine a manifesto that still sounds unmistakably human.[00:32:05] – One Manifesto Can Become a Movement (If You Dare to Ship It): What happens when you actually ship it—and how one document can anchor your strategy, content, and go-to-market for years.This isn’t about slogans or headlines.It’s about writing the story that defines your category—and claiming the future before someone else does.Arrrrrrr,Category Pirates 🏴‍☠️Eddie YoonChristopher LochheadKatrina Kirsch

This is a public episode. If you'd like to discuss this with other subscribers or get access to bonus episodes, visit www.categorypirates.news/subscribeYour audience wants you on call 24/7. Your calendar says no.That’s the real growth ceiling—not a lack of ideas, not even a lack of content. It’s access to you.We broke that ceiling by building a digital co-founder trained on our POV, frameworks, and voice. We call it Eddie Bot.This isn’t about replacing yourself. It’s about scaling your identity and turning decades of intellectual capital into something people can jam with 24/7, without you being chained to Zoom calls or your inbox.In this mini-book, we’ll break down exactly how we built Eddie Bot and how you can build your own “AI You.” Whether you’re a solopreneur, consultant, educator, or executive, this is your step-by-step for transforming your best ideas into a product that grows your reach, impact, and revenue while you sleep.Here’s what you’ll get inside:[00:01:42] – Why Your Brain Is Your Business: Your brain is your biggest growth asset—and your biggest bottleneck. Discover how to make it available 24/7 without adding a single meeting to your calendar.[00:06:50] – Define Your Bot’s Jobs To Be Done: The best AI clones don’t do everything. They do one thing so well it feels irreplaceable. Here’s how to find yours.[00:10:07] – Design Its POV and Personality: A bot with your files isn’t you. Learn the secrets to making it sound, think, and respond like the real thing.[00:18:51] – Train It On Your Best Thinking: If your AI eats junk, it’ll talk junk. The method for feeding it the right ideas, in the right order, for the right outcomes.[00:24:28] – Test Like a Superconsumer: Before you unleash it, battle-test it. The prompts and stress tests that turn “almost right” into “dead-on.”[00:27:00] – Tune It Like a Great Co-Founder: Great co-founders get better over time. So should your AI. Here’s how to keep it sharp and dialed-in.[00:30:08] – Monetize It Like a Pirate: Your AI isn’t a novelty—it’s an asset. We’ll show you the move that turned Eddie Bot into a major revenue driver.[00:33:11] – When AI Is the Business: The future isn’t using AI to support your business. It’s building a business where AI is the product.If you’re sitting on years of content, thinking, or customer insights—it’s time to put them to work in a smarter way.Arrrrrrr,Category Pirates 🏴‍☠️Eddie YoonChristopher LochheadKatrina Kirsch

Joe Pine didn’t start out trying to write a bestselling book.He didn’t have a “personal brand.”Or a big audience.Or even a plan.What he had was a question he couldn’t shake—and a belief that his ideas could lead to something more.While working at IBM, he kept circling the same question:What if businesses could create value beyond products and services?When IBM sent him to MIT for a graduate degree, he didn’t just go to learn. He went to explore. To write. To test his thinking in the real world.He wasn’t chasing a promotion.He was chasing clarity on his ideas and about himself.That’s when everything started to change. Because when Joe began writing, he created a new identity. That choice—to be someone who follows curiosity instead of convention—set him on the path from corporate strategist to Creator Capitalist.Joe traded a corporate title for a category of one.You don’t need a Fortune 100 job or an elite degree to do the same.Like Joe, you just need the courage to bet on your point of view and the tools to turn it into something real.Today, Joe is the co-author of The Experience Economy—one of the most influential business books of all time. He’s helped shape billion-dollar companies. Defined entire fields of thinking. And built a business on the back of his Intellectual Capital.In this conversation with Joe, we go back to the beginning.You’ll hear how he went from a self-described nerd at IBM, to writing Mass Customization at MIT, to launching a solo business with nothing but a severance check, a book idea, and the courage to build something of his own.What started as a thesis became a book. That book became a business. That business became a category. And that category created the Experience Economy.This episode is a look inside Joe’s leap from employee to author to category of one.You’ll walk away from this conversation knowing:* Why transformation starts with a new identity (long before that title shows up on your LinkedIn)* How Joe built Strategic Horizons as a solo consulting firm and why IBM became his first big client after leaving* Why writing is a catalyst for clarity, not just a credential* How Substack helped Joe write his latest book, Transformations, and why this different approach worked* Why every transformation—personal or professional—is rooted in emotion, identity, and intentionIf you want to be known for your thinking, this episode is a treasure map for turning your ideas into a business that pays you to be you.It’s not just a story.It’s proof that transformation begins the moment you decide to become someone new.Here’s how to navigate this conversation:* 00:50 – From IBM to MIT: Joe shares how getting sent to grad school became the launching point for his first book, Mass Customization, and why he always saw writing as a path to independence.* 06:06 – Books as Credential Capital: Joe explains how getting published by Harvard Business School Press and HBR positioned him as a trusted expert—and how one professor’s intro led to a game-changing contract.* 10:40 – Leaving IBM (Before He Was “Ready”): Joe tells the story of how he turned a severance check into a solo business and why his first client was IBM, the company that let him go.* 16:45 – Building Strategic Horizons: How meeting Jim Gilmore led to a legendary partnership and their co-authored category-defining work, The Experience Economy.* 20:24 – Creator Capitalism 101: Joe explains why you don’t need to be a genius to become a Creator Capitalist—you just need to know one thing better than anyone else, and be willing to share it.* 24:55 – The Creator Capitalist’s Dilemma: Joe talks about the emotional rollercoaster of creation, the long gaps between books, and why it took Substack to reignite his publishing momentum.* 27:20 – Substack As Catalyst: Joe shares how his newsletter helped him write faster, engage more deeply with readers, and monetize Intellectual Capital while writing.* 33:00 – Transformation Is Identity Change: Joe unpacks the core idea of his new book: All meaningful change begins with identity. He explains why every business must be a guide, not a hero, in its customers’ transformation journey.* 39:40 – Will Big Companies Make The Leap: Joe breaks down why most S&P 500 companies won’t transform fast enough with AI—and why the opportunity belongs to the next wave of entrepreneurial creators.* 46:44 – Joe’s #1 recommendation for future entrepreneurs: “Identify as an entrepreneur before you become one.”If you’ve ever said “someday” to writing a book, sharing your thinking, or launching your own business, this episode will show you how to start now.Because Joe Pine didn’t wait for permission.He wrote his way into the life he wanted.And that’s what it means to be a Creator Capitalist.To connect with Joe:* Connect with Joe on LinkedIn* Check out his Substack to preview his upcoming book* Read Joe’s books: The Experience Economy and Mass CustomizationArrrrrr,Category Pirates 🏴‍☠️Eddie YoonChristopher LochheadKatrina KirschP.S. — Your thinking isn’t just valuable. It’s ownable.You don’t need a publisher or permission to share your Intellectual Capital.You need clarity—and a little help sharpening your superpower, your point of view, and your offers.That’s why we built the Creator Capitalist course.This aysnc course shows you how to create:* A clear POV that sets you apart in any industry* A diagnostic for when to quit (or stay & scale)* A map to build offers & attract SuperconsumersReady to commit to a category-of-one career? Click here to take the Creator Capitalist quiz and see if it’s time to go all in. This is a public episode. If you'd like to discuss this with other subscribers or get access to bonus episodes, visit www.categorypirates.news/subscribe

Most people wouldn’t bring up pricing strategy when meeting Don Henley backstage.Or interrupt NFL players at a party to explain “good, better, best” pricing tiers.Rafi Mohammed has done both.Because pricing isn’t just his job—it’s his mission.But he didn’t plan to become the world’s leading expert on pricing. When he got handed a severance, he made a decision most people don’t.He bet on his obsession with pricing.If you’re Rafi, you don’t just change your pricing.You design a whole category around fixing the problem.After years at global consulting firms and publishing bestsellers like The Art of Pricing and The 1% Windfall, Rafi realized most companies were stuck in a “cost plus” mindset. They saw value as effort. When it was time to grow, they defaulted to cutting costs or increasing volume—instead of fixing the most strategic lever they had:Their pricing.That realization became the unlock.And in this episode, Rafi shares how he turned it into a business that pays for strategy—not time.You’ll walk away from this episode with:Why most people radically undervalue what they sell—and how to fix itHow Rafi built a business that pays for strategy, not timeThe mindset shift required to charge for value, not effortBecause pricing isn’t just about numbers.It’s a reflection of identity, strategy, and positioning.And when you stop treating pricing as an afterthought?You start getting paid for your ideas, not just your effort. This is a public episode. If you'd like to discuss this with other subscribers or get access to bonus episodes, visit www.categorypirates.news/subscribe

Holley Miller was supposed to be in the room.Executive meetings. Strategy sessions. Growth planning.She wasn’t there to take notes—she was there to lead.But when a senior leader looked at her and said, “Hun, can you grab me a cup of coffee?”—it wasn’t just a bad moment.It was the realization that no matter how hard she worked, she’d never fully be valued in a system she didn’t design.So when a new CMO role came along, she took it. Or so she thought.She quit her job. Sent an email to accept the new offer. And the reply?“Sorry. We needed confirmation by 5pm Eastern. The offer is no longer valid.”No job. No backup plan. No clear next move.So she picked up the phone.And called the competitor.That call became the beginning of Grey Matter Marketing, a category design firm that’s been shaping the future of life sciences for 18 years.In this episode, Holley shares how she turned years of being the one behind the outcomes into a business where she owns the credit, the thinking, and the economics.You’ll walk away from this episode with:A tactical view of how to productize your brain (and stop selling time)A mindset shift around pricing, team-building, and category leverage that lets you scale without burnoutA clearer understanding of how freedom is the reward—and how to build a business that gives you more of itHolley started with what she had: the trust she’d earned, the relationships she’d built, and the clarity she brought to complex problems.That Reputational Capital became her foundation.It gave her the leverage to step into consulting with confidence—before she even knew she was building a business. And over time, that leverage became Intellectual Capital: thinking she could price, package, scale, and grow.Holley didn’t just leave climbing the corporate ladder.She designed a business where her value wasn’t just seen—it was owned.That’s what it means to be a Creator Capitalist:You don’t rent your time. You own your thinking.You don’t chase roles. You compound your reputation, relationships, and revenue.You don’t wait to be picked. You productize what already makes you valuable.Holley’s story is proof: you don’t need a perfect plan to build something legendary. You need the courage to bet on the capital you’ve already earned. This is a public episode. If you'd like to discuss this with other subscribers or get access to bonus episodes, visit www.categorypirates.news/subscribe

This is a public episode. If you'd like to discuss this with other subscribers or get access to bonus episodes, visit www.categorypirates.news/subscribeVibe Creating is a radically different way of working with AI. Not to outsource your creativity, but to amplify your humanity. This mini-book breaks down how to collaborate with AI as if it were a co-founder. Not a vending machine. Not a Google replacement. But a creative partner who thinks with you.Inside, you'll meet entrepreneurs, consultants, strategists, and developers who’ve gone from burnt out to getting breakthroughs in record time. And you’ll learn a simple but wildly powerful 3-step framework to do the same: PukePromptPartnerThis isn’t prompt engineering.This is creative co-creation with AI.

This is a public episode. If you'd like to discuss this with other subscribers or get access to bonus episodes, visit www.categorypirates.news/subscribeAI isn’t here to take your job. It’s here to scale your Superpower—if you know how to build with it.The Pirate’s Guide to AI isn’t a “how-to” manual. It’s a strategic reframe. A new lens on AI—not as a bolt-on or productivity tool, but as a Creative Co-Founder that thinks, coaches, and creates alongside you.Just like a great co-founder, AI isn’t there to follow instructions. It’s there to challenge your assumptions and turn sparks into systems.In this mini-book, we show you how the best category designers use AI across three horizons:Near-term: Solve the obvious pain points faster.Mid-term: Unblock the bottlenecks stalling growth.Long-term: Co-invent moonshots and design the future.We also share 9 hard-earned (and painful) lessons from building with AI the wrong way—so you don’t waste months of momentum (or thousands of dollars) belly-flopping through dead-end experiments.Whether you're a solopreneur, founder, operator, or marketer, this audiobook gives you the mindset and method to turn AI into your smartest hire—without giving up your edge.If you're ready to stop dabbling and start designing with AI, this is your category compass.

It’s easy to feel stuck when your career is built around a job title—instead of a decision about who you want to become.You wait to feel qualified. You wait for clients to show up. You wait for your business to grow.Iron Mike Steadman didn’t wait.He chose who he wanted to become before the world saw it: marine officer, national boxing champ, podcaster.Today, he’s the go-to category designer for Black veteran entrepreneurs.This episode is a blueprint for anyone tired of chasing opportunities—and ready to create them instead.Mike walks through how he built a business around conviction, clarity, and category design—by doing three things most people avoid:Claiming an identity before he “felt ready”Redefining success around excellence, not incomeCharging for strategy instead of giving it away for freeHe doesn’t perform. He decides.He gets paid to be clear.If you want to stop sounding like everyone else, stop selling like everyone else, and finally start building the kind of business no one can copy...This is the blueprint.This is how you build the business only you can run.In this episode, you’ll learn how to reshape your identity, reframe your value, and replace tired sales tactics with clarity that commands respect (and revenue). This is a public episode. If you'd like to discuss this with other subscribers or get access to bonus episodes, visit www.categorypirates.news/subscribe