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/subscribeThis mini-book is read to you by AI Pirate Eddie.(If reading is more your style—or you want to see all sources and GIFs—you can read the written version here.)Most Americans have no idea how rare the country they live in actually is.Pirate Christopher’s Scottish grandfather crossed an ocean for a job at a rubber factory. Pirate Eddie’s father walked away from a law career in Korea to clean floors and drive a limo in Hawaii. Two families, two wars, two bets on the same country. Neither of us would be Pirates without it.Here’s the data most people walk past. Since 2007, Gallup has asked people in 150+ countries where they’d move if they could pick anywhere. The USA wins every time, by a mile. Not because Americans are superior. Because America is built differently.Every other country on Earth is a club. America is a catapult.That single idea is the spine of our new mini-book, now an audiobook. It’s a birthday letter to the USA, and it’s 25 predictions for the next 25 years, all built on weird data instead of wishful thinking.Optimism is easy to mock and hard to earn. We tried to earn it.Here’s what you’ll get inside:[00:02:18] – America Isn’t a Club, It’s a Catapult: The wealthiest man in Japan was bullied and denied credit for being ethnically Korean, in the only country he ever held citizenship in. You’ll hear why belonging by belief instead of blood is America’s rarest export.[00:05:27] – The Three Questions That Make a Country: How do you belong, where does power live, what does participation cost. Run every nation on Earth through those three questions and exactly one comes out the other side.[00:09:08] – Why Efficiency Never Kills Demand: In 1865, every smart economist bet that more efficient steam engines would burn less coal. They were spectacularly wrong. The Jevons Paradox is the most powerful argument against the scarcity premise ever written, and it’s why AI won’t shrink the pie, it’ll blow it wide open.[00:16:17] – The Moon Becomes America’s Number One Tax State: California throws off $265 billion a year in taxes. Do the category math on a fully industrialized moon, and the number that comes back is bigger. This is not Star Trek. Some of these resource contracts are already signed, and China isn’t the Category King of what comes next.[00:33:57] – Disease Is a Bug, and We Can Now Fix the Code: Your DNA is four letters running three billion lines of source code. CRISPR is a find-and-replace function for the human body, and we’re standing in the LASIK moment, back when a procedure went from millions of dollars to a Tuesday afternoon errand.If you’ve been told the future is something to brace for instead of something to build, this mini-book will change which direction you’re facing.That’s what it means to be a different category of country.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.

Here’s what we covered in this episode:1. State Farm is fighting to keep the customers it should fire.Progressive just took the personal auto crown State Farm held since World War II. It sells more than half its policies direct. No agent.State Farm’s answer: fly 19,000 agents to Vegas, throw a Pink concert, then tear up their contracts. Sign a worse deal by 2027 or take a buyout. Gross income could drop 40%.Did the CEO read the data right? No.He saw customers leaving and built a playbook for the wrong one.The switcher. Shops every renewal, picks the lowest number, gone the second someone is cheaper. State Farm has paid to chase that customer for decades. So has everyone else.The superconsumer. Never shops at renewal. Loves coverage, wants more, compounds lifetime value.The supers are already in the data, hiding behind non-obvious signals: too much life insurance, a thing for gummy vitamins, three or four refrigerators, a household that was ready when COVID hit. The super of one is the super of nine. The generator buyer is the insurance buyer.Mistake one: chase switchers instead of finding the supers already in the data.Mistake two: dismantle the agent network instead of backing the proactive agents over the reactive ones.Cut the switchers and the company shrinks while profit climbs.2. P&G is selling the technology when it should be selling the problem.P&G owns 60% of US detergent. Tide alone is close to 40. They spent a decade building Tide Evo, a dry three-inch tile. Since March it has taken 0.6% of the category.A consultant on the record cannot name the problem it solves at twice the price of a pod. Why?Because P&G is selling the tile, not the problem.Market the product and the customer thinks you want their money. Market the problem and they think you want to help.The problem is real and unspoken: Evo takes the water out. Easier to carry. Does not burst like a pod. Works in cold water, so you skip the heat and the cost.The superconsumer is the older, fixed-income customer who cannot wrestle the jug anymore. P&G is hiding from her because they think a niche shrinks the mass market. It does the opposite. Niching down expands word of mouth, which expands the market.Removing water is a category move a century old:* Nestlé, 1867. Dehydrated milk to reach babies fresh supply could not. It built a food empire.* Keurig. Sold coffee as a concentrate waiting for the water you add.* Starbucks Via. Reinvented instant coffee so completely it refused to call it that.* SodaStream. Ships the syrup and lets you pour the rest.Every decade, someone strips the water out of a wet product and unlocks a category.Pull the water and you pull it from manufacturing, packaging, the truck, and the shelf. At scale the tile should hit a 70% gross margin, well above liquid Tide near 50 and pods around 60. The retailer moves the same revenue in less shelf space.Name what you built and you own no-water detergent, plus every aisle where removing water applies next. P&G has not framed, named, or claimed any of it.3. America has a supply problem. Singapore had a category problem.America is short 1 to 5 million homes. The whole debate is supply: smaller lots, granny flats, less red tape. Starter homes used to be a third of everything built. Today they are 10%.Singapore refused the premise and built a different category. Public housing engineered for longevity and connection. Vertical villages that stack senior apartments, a medical center, and a preschool in one building. Elder care next to four-year-olds on purpose.The data is the strange part.* Life expectancy is up about 20 years since 1960.* Centenarians doubled in a decade.* Singapore is now the sixth blue zone on Earth, and the first one a government built from scratch.The residents with the most assets are the elderly, and they use the most healthcare, so they quietly cover the fixed cost of the building everyone else lives in. Co-living solves loneliness at both ends of the barbell, the young who have not started families and the old who outlived their friends.The Wall Street Journal covered the shortage and missed that the answer already shipped, with 20 extra years of life attached.3 conversations to have about the news with the Pirate Eddie Bot and Pirate Christopher BotWe just told you what is happening to three categories.The bots help you figure out what it means for yours. Reading the news is the easy part. Turning it into something actionable is the hard part, and it is exactly what The Pirate Eddie Bot and Pirate Christopher Bot are built for. They jam with you 24/7, they come with the founding tier, and they never get tired of your follow-up questions.Take this to them this week:* Find your supers through the non-obvious signals. Tell the bots what you sell and have them spec who quietly buys too much of it, the way the generator buyer keeps three refrigerators. The super of one is the super of nine. State Farm is chasing switchers and ignoring the supers in its own data.* Sell the problem, not the technology. Tell the bots what you built and have them name the problem it solves, then frame it, name it, and claim it. P&G took the water out of detergent and only talked about the tile.* Turn your shortage into a category. Tell the bots a problem everyone in your space calls a supply problem and have them rebuild it as a category problem. Singapore turned a housing shortage into 20 extra years of life.Not a founding member yet? You can join here.What’s coming up on Pirate Street JournalWe’re making a few changes to Pirate Street Journal next month.Every Tuesday, we drop a Pirate Street Journal episode at 7 a.m. PST / 10 A.M. EST. Three topics, thirty minutes, a couple of bongos.The first two Deep Dive Reports (DDRs) have already earned their keep:* Volume 1 (May 22, 2026): we said AI hardware was about to re-rate. Micron is up 61% and just posted the best quarter in its history.* Volume 2 (June 10, 2026): we said more than one thing can be true about the SpaceX IPO, strong for the long run and volatile near term. It IPO’d at $135, ran to $202, and sits at $153 as of June 25, 2026.The reports are built to pay off not just the day they drop, but over the next few quarters, even the next year or two. So we are making two changes.One, the reports get their own lane. Episodes drop Tuesdays. Mini-books and DDRs come out every other Friday.Two, who gets what changes. There are now two kinds of reports:* Deep Dive Reports (DDRs). The long, twice-a-month Friday reports. Founding Members get the full report. Everyone else gets a preview in their inbox and can read the rest by upgrading.* Breaking News reports. When there is breaking news on a category transformation, every paying subscriber gets the full report, Monthly and Founding alike.Starting with the next DDR, the complete version is a Founding Member benefit.Two ways to climb aboard now:Monthly: $20/month. You’ve done dumber things with $20. You get the Tuesday episodes, every DDR preview, and every Breaking News report in full.Founding: $375/year. About a dollar a day for every future DDR start to finish the day it drops, plus:* The Pirate Eddie Bot and the Pirate Christopher Bot, your 24/7 AI jamming partners* Every mini-book we have ever written (300+)* Our entire audiobook library (30+)* All seven of our full-size booksWant the whole thing every time? Become a Founding Member.Recorded Friday, June 26th. Every number above is as of that morning.Piratey disclaimer: This is NOT financial advice. None of us have a Series 63, Series 7, Series 6, CPAs, CFAs, IUDs, IEDs, and hopefully not IBS (this makes DUDE Wipes sad).Stay tuned for next week’s episode.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/subscribe

SpaceX went public on a Friday.By Tuesday, it was worth $2.5 trillion, bigger than Amazon.Four days in, it spent $60 billion on a four-year-old startup.That startup was worth half as much in November.Wall Street called the price insane.The price is the least interesting thing about it.Here’s what we covered in this episode:1. Wall Street says Musk overpaid for Cursor. We think it was a bargain.SpaceX hit $2.5 trillion by Tuesday and passed Amazon into the top five in America. Then it bought Cursor, the AI coding startup, for $60 billion in stock. Cursor was worth about $29 billion in November, so Musk paid double in a few months. Four MIT students built it in 2022, the CEO is 25, and a team in the low hundreds already throws off billions in revenue against Claude Code and Codex.There are two kinds of acquisitions.One buys a rival in a flat category and strips out the duplicate cost. That is what most people picture.This is the other kind. You buy the king of a category about to explode.Cursor’s founder said he built a new type of software, a category for building AI software with AI. The press fixated on the price and missed the sentence.Microsoft bought DOS. Google bought YouTube. Facebook bought Instagram. Each one looked overpriced for the same reason.2. Trillion-dollar companies can't get power approved. A million households fixed it with a balconyTwo weeks ago we said the power layer of the AI stack is nearly empty, with about $156 billion of US data center projects blocked or delayed. In Germany, more than a million households installed plug-in solar. You hang panels on a balcony, plug into a wall outlet, and run in under an hour. Each one is capped around 800 watts.Utah went first last year. Several states have legalized it since, and more than 30 are now considering it.A starter kit runs a few hundred dollars and pays for itself in a few years where power hits 30 to 40 cents a kilowatt-hour.Rooftop solar stayed a luxury because of permits and cost. Strip those away and a new category shows up: distributed, consumer-owned power at Costco prices.3. Chick-fil-A makes four times what KFC does per store, and it's closed on Sundays.KFC is 74 years old, 34,000 restaurants, over 150 countries, and just announced the biggest overhaul in its history. New sauces, a boba drinks line called KWENCH, interiors built like an Apple store crossed with a Vegas sphere, new logo. Same week, Yum sold Pizza Hut for $2.7 billion to bet harder on chicken.KFC has more US locations than Chick-fil-A, over 3,600 stores, under $2 million a year each. Chick-fil-A does about $7.5 million per store. Four times the money, with one fewer day a week, because it closes on Sundays.KFC’s problem was never store count. It’s the category design inside each box.Boba and screens redecorate the magic triangle without refreshing it.Chick-fil-A’s edge is the ownership model: private, anti-franchise, a $10,000 buy-in, an acceptance rate under 1%, two drive-thru lanes, a menu tight enough to keep the line moving.KFC already ceded Southern fried to Popeyes and the mega category to Chick-fil-A at home. Its real weapon is a global footprint and the one food that travels everywhere. Bring the best foreign menus back and win on what makes it different.3 conversations to have about the news with the Pirate Eddie Bot and Pirate Christopher BotWe just told you what is happening to three categories. The bots help you figure out what it means for yours. Reading the news is the easy part. Turning it into something actionable is the most important piece, and it is exactly what The Pirate Eddie Bot and Pirate Christopher Bot are built for. They jam with you 24/7, they come with the founding tier, and they never get tired of your follow-up questions.Take this to them this week:* Sort your next big bet into consolidation or acceleration. Ask the bots which moves in your space buy a category king and which only buy cost savings. Musk just paid $60 billion to own the top of a stack he didn’t build.* Find the abundance play in your category. Tell the bots what you sell and have them spec a version that gets cheaper and better the more people use it, the way a million balconies beat one. Then ask where the network effect kicks in and how this is relevant to you.* Stress-test your own glow-up. Tell the bots what you are about to change and have them split it into surface redecoration and real category design. KFC is spending its biggest budget ever on boba while Chick-fil-A makes four times per store.Not a founding member yet? You can join here.What’s coming up on Pirate Street JournalEvery week, we drop the podcast. Three topics, thirty minutes, one cowbell.Once a month, we publish a written deep dive, the kind of category analysis you cannot get anywhere else. That one is for paying subscribers only, monthly and founding.Two ways to climb aboard now:Monthly subscriber: $20/month. You’ve done dumber things with $20.Founding subscriber: $375/year. For about a dollar a day, you get every mini-book we’ve ever written (300+), every audiobook (30+), digital copies of all seven of our Big Books, and unlimited access to The Pirate Eddie Bot and Pirate Christopher Bot, your 24/7 AI jamming partners for category building.Subscribe today and start jamming with the bots.Recorded Friday, June 12. Every number above is as of that morning.Piratey disclaimer: This is NOT financial advice. None of us have a Series 63, Series 7, Series 6, CPAs, CFAs, IUDs, IEDs, and hopefully not IBS (this makes DUDE Wipes sad).Stay tuned for next week’s episode.Hey Ho, Let’s Go!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/subscribe

Gartner grew its revenue again last year.Investors wiped out more than $30 billion of its value anyway.The stock fell from $551 to $155 in about twelve months.Still profitable. Still growing. Still the name every CIO knows.Wall Street just stopped believing it has a future worth paying for.The business is fine. The future got repriced.Here’s what we covered in this episode:1. Gartner grew revenue again last year. Wall Street wiped out $30 billion anyway.For 40 years, Gartner was the company you paid to tell you what tech to buy. It peaked at $551 a share in November 2024. This week it trades around $155, a 70% collapse, with market cap down from roughly $42 billion to about $10 billion.The revenue still grows. That is not the point. For a growth company, value is investors’ read on the category's going-forward potential, and Wall Street has decided that Gartner does not have one. The moment you can ask an AI which CRM to buy and get a real answer for free, a six-figure research subscription starts to look like a fax machine.Roger Martin pegs true strategy at about 3% of what the big consulting firms sell. The other 97% is best practices, benchmarking, gap analysis. Monkey see, monkey do. That is exactly what AI commoditizes first. The value moved to whoever can create net-new knowledge instead of repackaging the old kind.2. Thirty vendors paid in, consumers paid $250 at the door, and the marketing event turned a profit.An aesthetics company called Orange Twist ran a Lightning Strike in Newport Beach called TwistX. A mid-six-figure event at the Hyatt that turned a profit. Vendors covered about a third (30 brands paying to get in front of buyers), consumers covered about a third ($250 a head at the door), and on-the-spot treatment bookings covered the rest. Paid media for the whole thing ran maybe four figures.A Lightning Strike concentrates a year of marketing budget into one moment instead of spreading it thin across twelve. Pulled off right, it pays for itself, which flips marketing from cost center to profit center. Almost nobody does it.It also shows where consumer money goes when everything digital gets cheaper by the week: AI, agency, and the body you live in. Two GLP-1 drugs now do about $55 billion a year at 80% margins, matching the combined revenue of the top four AI companies at half the margin. The one thing a model cannot hand you is what you see in the mirror.3. Teen unemployment is actually lower than it was in 1979. The Wall Street Journal calls it a crisis.The Wall Street Journal ran a crisis headline: summer hiring for teens is the weakest since the government started counting in 1948. Then look at the data. Teen participation peaked near 58% in 1979, and the share holding a job has fallen from 49% to 31%. But teen unemployment is 14% today, down from 16% in 1979. The kids who want work are finding it faster than their parents did. New York City’s summer program drew 200,000 applicants for 100,000 slots and had to run a lottery.The decline is almost entirely teenagers opting out. The edge a wealthy kid used to buy with an unpaid internship now costs $20 a month for anyone with a laptop. The gate the Journal is mourning just blew open.Run the math the way Pirate Christopher did. A young person who banks $100,000 and parks it in the S&P 500 at a 10% historical average is worth about $1.7 million in 30 years. Wealthy people own things that work for them. That lesson is finally cheap enough for everyone.What’s coming up on Pirate Street JournalEvery week, we drop the podcast. Three topics, thirty minutes, one cowbell.Once a month, we publish a written deep dive, the kind of category analysis you cannot get anywhere else. That one is for paying subscribers only, monthly and founding.Two ways to climb aboard now:Monthly subscriber: $20/month. You’ve done dumber things with $20.Founding subscriber: $375/year. For about a dollar a day, you get every mini-book we’ve ever written (300+), every audiobook (30+), digital copies of all seven of our Big Books, and unlimited access to The Pirate Eddie Bot and Pirate Christopher Bot, your 24/7 AI jamming partners for category building.Subscribe today and start jamming with the bots.Recorded Friday, June 12. Every number above is as of that morning.Piratey disclaimer: This is NOT financial advice. None of us have a Series 63, Series 7, Series 6, CPAs, CFAs, IUDs, IEDs, and hopefully not IBS (this makes DUDE Wipes sad).Stay tuned for next week’s episode.Hey Ho, Let’s Go!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/subscribe

We loved celebrating all the moms in our lives a few weeks ago over Mother’s Day, and now it’s time to celebrate the dads.Before we get into the episode, we have something fun to share.The Parent Bundle and a Father’s Day offerThis week we’re launching the Parent Bundle, and if you sign up as a new Founding Subscriber between now and Father’s Day, you’ll get the full bundle included at no extra charge.Here’s what’s inside:* The Joy Book: written by Pirate Eddie’s daughter Audrey (when she was in 6th grade), this physical book is available individually for $25 (more on this below)* How To Build Your First (Crazy Profitable) Business As A Teenager Vol. 1: 18 radical ideas for Native Digital entrepreneurs. The original. Available individually for $12.99 on Amazon here.* How To Build Your First (Crazy Profitable) Business As A Teenager Vol. 2: the AI sequel: 18 more ideas built for the era of AI co-founders and $30K summers. Available individually for $12.99 on Amazon here.Know a dad who needs this? Share this post (and next week’s mini-book: Fatherhood 3.0) with him. Know a teen who should read the AI book? The Vol. 1 and Vol. 2 links are right there. And if you just want the whole stack for yourself, the $40 full physical bundle has you covered.New Founding Subscribers who sign up before midnight PST on June 21 get the full physical bundle free.If you’re already a Founding Subscriber, watch your inbox for a digital version of the Joy.If you’re ready to hop aboard, you’ll get the Parent bundle on the house and immediate access to the Pirate Eddie and Christopher Bots (your 24/7 category design jam partners), access to our full audiobook library (35+), and the entire Category Pirate library (including all 7 of our big books and 300+ mini-books).→ [Become a Founding Subscriber and get the Parent Bundle included here.]Now. To the episode.Fatherhood 1.0 left the building. Fatherhood 2.0 showed up. Fatherhood 3.0 might be the most important design challenge yet.A generation ago, fathers worked.That was the job. Leave it to Beaver dads were providers, not participants. Fatherhood 1.0 was simple, if you squinted past how hollow it actually was.Then the data shifted. Today’s fathers spend 90 minutes a day on childcare in the United States, up from 20 minutes in 1985. In Canada, the number tripled. Globally, across Germany, Norway, Japan, Australia, the arc is the same: fathers are more present than any prior generation.So why does it still feel like a false choice? Why does “legendary career” still seem to compete with “legendary father”?In this episode, Pirates Eddie, Christopher, and Bri dig into what that tension actually is, and where it comes from. And the answer is more interesting than “you need better balance.”The problem with Fatherhood 2.0 isn’t the quantity of time. It’s what children see when they have it.The most powerful gift a father can give has nothing to do with attendancePirate Christopher’s late therapist, David Willingham, put his finger on something that the modern parenting conversation has mostly missed.For generations, children watched their fathers work. Farmers, shop owners, craftsmen, small business owners: the work happened at home or nearby, and children saw their fathers being excellent at something. As the economy shifted and fathers disappeared into offices, children inherited a different version of fatherhood: a man who came home tired.Present, maybe. But not at his most powerful.The Creator Capitalist unlock here runs parallel to what we explored with Motherhood 3.0: when you separate your time from your income, you don’t just get agency over your schedule. You get to show your kids what it looks like when you’re actually doing the thing you were built to do.Not a watered-down, weekend version of yourself. The whole thing.Pirate Eddie walked through the math of his own career, making partner in consulting while his kids were young, traveling constantly, trying to be present on the weekends while his wife, Pirate Kristen, carried the weight at home. He’s candid about what the tradeoffs cost. But Pirate Christopher reframes the ledger: Eddie’s kids didn’t just miss time with their father. They watched their father build something legendary. And those two things aren’t in opposition.The false choice of Fatherhood 2.0 is: you can have a great career OR you can be a great dad. Pirates reject that premise entirely.The Joy Book: what Pirate Eddie’s daughter actually thinksSpeaking of what kids absorb.Audrey Yoon wrote a book about growing up with Eddie as her father. The title is deliberately not spoiled here. What we’ll say is this: her early memories include a 6 a.m. birthday breakfast before a 9 a.m. flight. Pirate Eddie tells the story with some sheepishness in the episode. Audrey tells it as one of her favorites.Kids see differently than we think they do.Here’s a sneak peek at what’s inside (read to you by Pirate Eddie and animated by his oldest daughter, Miya):The Joy Book is available now in the Shopify store, individually for $25, and bundled in the Parent Bundle for $40. It was written by Audrey, and it is the most honest accounting of Fatherhood 2.0 you will find.Here’s how to navigate this conversation:* 0:00 – Tom Peters and the Creator Capitalist origin story: Pirate Eddie and Christopher open with Roger Martin’s X post and land on Tom Peters as one of the original creator capitalists, which sets up everything that follows about what it means to make your own place rather than fit into someone else’s.* 7:33 – The four capitals and the fatherhood problem: Pirate Christopher pivots to the core thesis: trading time for money is what breaks both fatherhood and financial capital.* 14:00 – The data that got Pirate Eddie thinking: Pirate Bri shares the charts. Fathers globally are tripling their childcare time. The numbers are real and they set up the hard question: why isn’t it working the way we thought it would?* 18:27 – Pirate Eddie’s honest accounting of his own career as a father: Partner while the kids were little, global travel, Kristen carrying the weight. He doesn’t spin it. He walks through what he would do differently, and what he wouldn’t.* 24:00 – The therapist’s point about watching your father work: Pirate Christopher shares Willingham’s thesis: multiple generations ago, kids witnessed their fathers being excellent. Then offices happened. This is where the episode shifts from data to category design.* 29:00 – Rejecting the false choice: Pirate Christopher lands the argument. Legendary career OR legendary father is a premise to reject, not a trade to manage. The Creator Capitalist path is what breaks the chain.* 45:00 – Parenting never ends, and that’s the most terrifying insight: Pirate Eddie on what it looks like when the problems level up from “don’t touch the stove” to “what do you do when your kid marries the wrong person.”* 47:07 – Pirate Christopher’s six-and-a-half years: Tushar’s murder, Michael’s death, COVID, the DA, 2,407 days to four life sentences. What children see when they watch the adults they love stand back up.* 57:19 – Pirate Bri’s reader’s digest: The daughter’s perspective, her dad’s absence, and the question she’s watching her generation not quite answer yet: what does Fatherhood 4.0 look like when kids who had all the presence grow up?Fatherhood 3.0 is the design problem worth solvingFatherhood 1.0 was presence-optional. Fatherhood 2.0 added presence and kept the career, and then wondered why the tradeoffs were still brutal.Fatherhood 3.0 asks a different question: what if you could stop choosing?Next week we’re releasing the Fatherhood 3.0 mini-book. If you haven’t already, go read the Motherhood 3.0 mini-book first. The theses are designed to be read together.And if this episode hit differently, Audrey’s book is the version of this story told from inside the house.Go get the Parent Bundle. Come back next week. And in the meantime, do something legendary in front of your kids.Arrrrrrr,Category PiratesEddie YoonChristopher LochheadP.S. The Parent Bundle is live, and new Founding Subscribers get it free through Father’s Day.The Joy Book ($25 individually), AI Teen Books Vol. 1 and 2, are all bundled together for $40. New Founding Subscribers who sign up between now and Father’s Day get the bundle included at no extra cost. Existing Founding Subscribers get digital versions on the house.The Pirate Eddie Bot and Christopher Bot also come with your Founding subscription, so you can start working through your own category design any time.→ [Become a Founding Subscriber and get the Parent Bundle 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 free preview of a paid episode. To hear more, visit www.categorypirates.newsOn June 12, SpaceX is going public at $135 per share and a $1.75 trillion valuation.4% of total shares are being offered. Of those, 30% have been allocated for retail investors to buy directly at the $135 IPO price. The standard retail allocation in a mega-cap IPO is 5 to 10% of shares, with the overwhelming majority reserved for large institutional buyers like pension funds and mutual fund managers.SpaceX is tripling that, which is unusual.At a $75 billion raise, that is roughly $22.5 billion in shares flowing directly to retail. More than many entire IPOs.One of SpaceX’s lead underwriters told Reuters they had never seen anything like the expected retail demand.Both Anthropic and OpenAI have also filed to go public sometime this fall.It is a mad rush to raise capital to fund the AI infrastructure buildout. Valuations defy gravity and become a moving target as ARRs change every month and cash-burning businesses like xAI flip to cash-flowing with the stroke of a single deal.IPOs Are Dangerous, Right?Truist analyst Keith Lerner pulled the data on 30 major IPOs from the last 15 years.The names you have heard of. Facebook. Uber. Palantir. Snowflake. CrowdStrike. Even the biggest winners experienced massive take-downs in their first year.The median Year 1 max drawdown across all 30 IPOs was 54%. The average was 55%. Robinhood dropped 90% from its peak. Rivian dropped 88%. Lyft dropped 79%. Uber dropped 68%.That is just the drawdown. Jay Ritter at the University of Florida has tracked every U.S. IPO since 1980. Over three years, the average IPO underperforms the market by 23.4%.It is a feeding frenzy for the sharpest sharks on Wall Street. IPOs get bid up by retail enthusiasm, then shorted on the way down. The average Joe and Jane gets whacked.So if you are sitting at home watching the SpaceX IPO ads roll across your screen, the safest move is to: remember the data.Except.It turns out most of America will eventually invest in SpaceX (and likely Anthropic and OpenAI) whether they realize it or not.62% of Americans own stock as of 2024. The vast majority of that ownership is indirect, sitting inside 401(k)s, IRAs, S&P 500 index funds, and total market funds. The S&P 500 alone is tracked by tens of trillions of dollars in passive money.To get into the S&P 500, a company is supposed to make money. The sum of its four quarters of earnings has to be positive on a GAAP basis, and so does its most recent quarter. That rule is decades old. It is the reason Tesla sat outside of the index until the end of 2020, years after it had become one of the most valuable companies on earth.That rule is about to be broken on purpose for some of the indices.The other major indexes have already moved. Nasdaq’s Fast Entry rule, effective May 1, 2026, cut the Nasdaq-100 waiting window from roughly three months to 15 trading days. CRSP, the index behind Vanguard’s funds, introduced an alternative path that could place SpaceX in the Russell 1000 within five trading days of the IPO.The S&P 500 refused to change the rules.So is this bad?Not necessarily. There will be many Category Kings of the AI era. SpaceX is currently one of them. So who will be the Category Kings of AI? And how does the AI game board look through the category lens?Let’s look at who the Category Kings were across the value stack in the PC era, the Dot-com era, and the Social/Mobile era. The pattern tells us what to look for now.Remember, we’re not financial advisors, and this is not personal financial advice.We’re presenting you with data through the category lens to give you a different POV on how categories rise and fall. And in this case, how the mega tech stack categories evolve over time.The Pirates 6 Layer Rum CakeJensen Huang sells the AI economy as a five-layer cake. Energy at the bottom. Chips next. Cloud infrastructure above that. Models on top of cloud. Applications at the very top. Stack them. Slice them. Invest in them.It is a useful frame.It is also incomplete.The Pirates expanded the cake to six layers and simplified the language. Power instead of Energy. Internal Hardware instead of Chips. Infrastructure stays. Operating System instead of Models, because the OS is what every era’s category designer has always called the layer that makes everything else work. We added a layer Jensen left out. End-User Hardware. The device the customer touches. The PC, the phone, the device, the App Store toll booth. Applications stays at the top.Six layers. Power, Internal Hardware, Infrastructure, Operating System, End-User Hardware, Applications.The reason Jensen’s cake matters less than the Pirates Cake is that Jensen’s cake describes one era. The Pirates Cake describes every era. PC. Dot-com. Social/Mobile. AI. Same six layers, different category leaders.Before digging in, three rules guide the analysis.Rule 1. Pay close attention to multi-era category kings.Microsoft won the PC era. Microsoft won the Dot-com era. Microsoft is in the top three of the AI era opening act, four decades after going public. A $10,000 investment in Microsoft at its 1986 IPO, held through every crash and every doubt, was worth approximately $80 million by December 31, 2025.Roughly 8,000x.A 26% compound annual return for forty years.A $10,000 investment in Apple at its 1980 IPO was worth approximately $25 million by the same date.Roughly 2,500x.A 19% compound annual return for forty-five years.A $10,000 investment in Apple the day the iPhone launched in June 2007 was worth approximately $570,000 by December 31, 2025. Roughly 57x in eighteen years.What’s our point? There will be multiple Category Kings. You can still do great, even if you miss it early.Multi-era winners compound through platform shifts, recessions, market crashes, leadership changes, and competitor onslaughts.Rule 2. Hardware wins first. Then software.Every era opens with a hardware-led leader. IBM in PC. Intel in Dot-com. Microsoft in Social/Mobile, which is the exception that proves the rule because Microsoft was the prior era’s vertical integrator extending its run.Now Nvidia in AI.The opening years of every era belong to whoever ships the picks and shovels. Always. The closing years belong to whoever owns the operating system and the layers closest to the customer.Rule 3. Multi-era winners own the most valuable areas of the stack.Not the most layers. The most valuable ones. Operating Systems are always one of them. End-User Hardware or Distribution into the customer is usually another. Applications on top are the third. The App Store alone takes 30% of every transaction every developer makes on the platform forever. That is the most valuable layer in the matrix, and Apple owns it outright. The closer to the customer, the higher the multiple. Internal Hardware is bigger in revenue. End-User Hardware and Apps are bigger in compounding value.Now walk the matrix.The Era MatrixCompanies as rows. Layers as columns. Each filled dot is a real owned business in that layer. The two market cap columns show the average across the first three years of an era and the last three years. Teal marks the first-window leader. Pink marks the last-window winner. They are never the same company.PC era · 1985 to 1999The first-window leader was IBM at 79.9% share of named-player market cap. IBM owned three layers. Internal Hardware in mainframes and servers. Infrastructure in enterprise services. End-User Hardware in the original IBM PC and the ThinkPad. IBM won the opening for one reason. The IBM PC defined the category. Every other PC was an IBM clone. The hardware that ran the era belonged to IBM.The last-window winner was Microsoft at 41.9% share. Microsoft owned three layers. Operating System in Windows. Distribution through OEM bundling deals that put Windows on every PC sold. Applications in Office. Microsoft did not make hardware. Microsoft made the thing every piece of hardware needed to be useful. By 1999, Windows ran on 95% of PCs sold. Office had no real competition. Microsoft was, briefly, the most valuable company in the world.IBM dropped to 17.6% by the close. The hardware category gets the party started, and Operating Systems take the stage later.Dot-com era · 1995 to 2002The first-window leader was Intel at 25.1% share. One layer. Internal Hardware. Every server, every workstation, every desktop running the web ran on Intel chips. The web was a hardware buildout before it was anything else. Cisco rode the same wave at 11.4%. IBM held on at 16.8%.The last-window winner was Microsoft at 24.7% share. Same Microsoft. Same three layers. Same Operating System. Same Distribution. Same Applications.This is the most important data point in the matrix. Microsoft is the only multi-era, multi-category winner in modern technology history. Won PC. Won Dot-com. Did it by holding the Operating System layer through the platform transition. Windows ran the local PC. Internet Explorer bundled into Windows became the way most people got to the web. Office moved from the desktop to the web. Same playbook. New surface. Same compounding.Intel finished Dot-com at 20.1%. Cisco at 16.8%. Both are still huge. Both are about to fall away in the next era. The hardware leader of one era is rarely the hardware leader of the next.Social/Mobile era · 2004 to 2020The first-window Category King was Microsoft at 47.0% share. The same Microsoft. Two consecutive era wins and into the category lead of the third era’s opening act. This is what Rule 1 looks like on a chart.The last-window winner was Apple at 25.3% share. Apple owned four layers. Internal Hardware in Apple Silicon. Operating System in iOS. End-User Hardware in the iPhone and the App Store. Applications in Music, Maps, Messages, Camera, Photos. The most complete vertical integration in technology history.Apple owned the most valuable layers of the stack. Operating System. End-User Hardware. Apps. The three layers closest to the customer.Intel collapsed from 21.9% opening share to 3.9% closing share. The hardware leader of the prior era lost an entire era’s worth of share. Cisco never recovered from Dot-com. Microsoft, the vertical integrator, did. Same pattern as the IBM-to-Microsoft handoff. Hardware leaders fade when the layers they do not own start to compound.Nvidia opened Social/Mobile at 1.1% and closed at 3.2%.Few people saw what they were going to do next.AI era · 2024 to 2026Nvidia is the first-window Category King at 22.3% share. One bingo point in Internal Hardware. Same role Intel played in Dot-com. Same role IBM played in PC.Behind Nvidia: Apple at 20.3% with four layers. Microsoft at 19.6% with three layers. Alphabet at 12.9% with five layers. The vertical integrators are already in position. The last-window Category King has not declared itself yet. The matrix says it will not be Nvidia, if they don’t add more points on the Bingo card. The matrix says it will be one of the companies with the most valuable and/or the most points on the Bingo Card. Ideally, it will own the Operating System plus the layers closest to the customer.The question is which one.Head to Head in the AI EraWe have a few hypotheses about what might happen next.Hypothesis 1. Low-regulation states can be the Category King in US power.China is adding the equivalent of the entire US grid every few years.In 2025, China added 543 gigawatts of new capacity across all technologies. That single year of additions is 12% more than all the power plants combined in India. China’s total power generation capacity is now 3.75 terawatts. The US sits at 1.3 terawatts. Roughly three times the US. China is investing more than $500 billion per year in energy buildout. The US grid grew by a fraction of that.Regarding Power, the US federal government is being slow and stupid.Poorer, but prescient states can leapfrog their legacy.The regulation, the permitting, the environmental review cycles, the local NIMBY opposition. None of it is calibrated for an AI era that needs power yesterday. Microsoft had to revive Three Mile Island because building a new nuclear plant from scratch is essentially illegal.So xAI built Colossus 1 in Memphis, Tennessee. You would think they would be in the pole position for Colossus 2.Tennessee regulators slow-walked the gas turbine permits.Mississippi said yes.Mississippi’s governor announced xAI’s $20 billion investment as the largest single investment in Mississippi history. Tennessee just took Starbucks and In-N-Out headquarters.The states willing to build will win the AI era.California’s regulatory structure makes it effectively impossible to build the hyperscale facilities (500 MW+) that are now the standard for AI infrastructure.Developers in California top out around 50 MW. In Virginia and Texas, projects routinely run ten times that size.Every transmission line, backup generator, and power connection triggers CEQA environmental review, adding 18–36 months to any project timeline.The result: Silicon Valley has 489 MW of total data center capacity. Northern Virginia has 4,039 MW. That’s an 8x gap. And Virginia added over 1 GW of new capacity in 2025 alone. California added roughly 20 MW.Texas is booming with abundant land and no state income tax.Google committed $40 billion to Texas data center infrastructure through 2027. Microsoft is scrambling to secure natural gas-backed sites in Texas and West Virginia. No comparable investment is flowing into California.You can see smaller, speedier governments winning in Asia.Korea is the only country in the world other than the US with more than one trillion-dollar market cap company. Samsung Electronics crossed $1 trillion in May 2026. SK Hynix crossed three weeks later.Both built on the DRAM and HBM memory categories that feed the AI hardware buildout. Two trillion-dollar companies in a country of 51 million people, mostly because they own a critical category in the AI value stack.Bloomberg Economics forecasts Samsung and SK Hynix combined performance bonuses alone will grow from 4 trillion won in 2026 to 30 trillion won by 2028. South Korea’s finance minister is publicly debating how to use the tax windfall, with talk of creating a sovereign wealth fund to absorb it.Korea Herald is reporting Samsung and SK Hynix combined tax revenue over the next three years is projected to roughly equal half of South Korea’s national government debt.Two companies.Three years.Half the country’s debt.And Korea’s debt-to-GDP ratio is already only 49%, less than half the US level. The AI tax windfall is hitting a country that did not need it. That is what owning a single category in the AI value stack can do for an entire economy.Europe and high-regulation US states lose.California cannot build a 170-foot bridge in under three years. California is not going to build power plants and data centers in the AI era. Europe has not had a meaningful new technology company at scale in two decades.Both will be left behind.Western Europe, sadly, is becoming a place locked in the past, where tourists from the future visit.Hypothesis 2. Today, Alphabet and Muskonomy appear poised to win.Both are going for full bingo.Both own or are acquiring more layers than the rest of the field. Alphabet has the cash flow to solve the layers they do not yet own. Musk has the ability to raise immense amounts of capital just on the cult of his personality.Hypothesis 3. Expect weird M&A and JVs.The enemy of my enemy is my friend.Microsoft and OpenAI was the masterstroke of the era’s opening years. And now reportedly fraying. Musk had public beef with Anthropic, but his beef with OpenAI was bigger, so he cut a $1.25 billion per month deal with Anthropic for Colossus capacity.Google just cut a deal to pay xAI over $900 million per month for compute. This seems odd given they are both going for Bingo, but then again Google owns a healthy chunk of SpaceX.Solo players will shrivel.Standing alone with one or two layers is not a path to winning. In the mega categories. It is a path to being acquired, merged, or marginalized.With these hypotheses in mind, here is what must be true for each player to be the AI era Category King.NvidiaNvidia has one spot on the bingo card. ProudlyInternal Hardware. But their timing is awesome right now.Here’s what must be true for Nvidia to win.Nvidia must hope that the Internal Hardware phase is the longest of any era we’ve seen. This is the bet they are making, which is investing within the Internal Hardware part of the stack. Nvidia’s taken their monster cash flows and invested $2 billion into Lumentum, which is Optics and Components. They invested $3 billion into Corning for fiber optic cables. They invested $2 billion into Synopsys, a leading electronic design automation firm. And a $2 billion investment into Coreweave, to help build out clouds. If Internal Hardware’s reign lasts a long time, Nvidia will be fine.While they aren’t personally moving into other areas of the bingo card, Nvidia has committed $53 billion in about 170 deals across the value stack.* Power: $2.1 billion into Iris Energy* Operating Systems: $100 billion commitment to OpenAI, $10 billion into Anthropic and $2 billion into xAI* End User hardware: They participated in a $1 billion Series C into Wayve, a UK autonomous vehicle company. They also invested in a $675 million dollar round into Figure AI robotics.* End User applications: $50 million into Recursion Pharmaceuticals, $50 million into Kore.ai, a conversational AI for enterprise, participated in a $141 million Series B for Hippocratic.ai, a medical-grade LLM.Equity stakes are great, but they are not businesses they own.Nvidia’s bet is that hardware demand stays insatiable for years. The playbook from here is the Apple playbook of the 2010s. Stock buybacks. Dividends. Returning cash to shareholders. Growing the stock through financial engineering rather than category expansion.Nvidia is going to be enormous. And unlikely to be the era mega-category winner.OpenAIOpenAI has two spots on the bingo card.Operating System in GPT. Applications in ChatGPT and enterprise products.Here’s what must be true for OpenAI to win.The rumored chip program would add Internal Hardware. Stargate would add Infrastructure. ChatGPT has consumer mindshare but does not own end-user hardware. Jony Ive left Apple to join OpenAI, and he’s building a consumer AI device. The Apple deal would add Distribution into End-User Hardware.That’s a lot to do, while trying to out-innovate Anthropic.And the rumored trust issues with Sam Altman make partnerships tricky. If the capital markets tighten, OpenAI does not have Alphabet’s cash flow to buy their way in.AnthropicLike OpenAI, Anthropic has two spots on the bingo card.Operating System in Claude. Applications in Claude.ai, Claude Code, and enterprise products. Unlike OpenAI, Anthropic had a rumored profitable quarter and ARR that seems to grow each month.Here’s what must be true for Anthropic to win.Anthropic has a lot of the bingo card to fill, with cash flow that is promising but not yet present. This means partnerships are the default.The Colossus deal with Musk gives Anthropic Infrastructure access without owning it. The enterprise embedding strategy through Claude Code, Claude in Excel, and Claude in Chrome is a credible path to being inside every workflow rather than owning a consumer surface.The math of building Power, Internal Hardware, Infrastructure, End User Hardware and Applications organically is brutal. The math of joining one of the bingo contenders is easier.MetaMeta has three spots on the bingo card.Infrastructure in their own data centers. End-User Hardware in Ray-Ban Meta and Quest. Applications in Facebook, Instagram, and WhatsApp.Here’s what must be true for Meta to win.Meta must solve for power, but as important, Meta would need to build or buy a real Operating System. Llama is a model, not an OS layer the way iOS or Gemini is. Meta would need Internal Hardware beyond MTIA.This is where all the cash they burned on AR/VR would have come in handy. These are a lot of spots on the bingo card to invest or buy their way into.Facebook needs a friend. A deep partnership with someone who has the layers Meta does not have. Standing alone, Meta does not have a credible path to bingo.MicrosoftMicrosoft has three spots on the bingo card.Infrastructure in Azure. Operating System in Windows and Copilot, as well as their partnership with OpenAI. Applications in M365 and Copilot apps.Here’s what must be true for Microsoft.Microsoft has to solve for Power and Internal Hardware. Power is the same constraint everyone faces, but Microsoft has the cash flow and the data center footprint to move first. Internal Hardware is the harder one.Microsoft has never been good at end-user hardware. Windows Mobile failed. Zune failed. Surface is a rounding error. And Microsoft lost over one billion on their retail stores.Can they win in Internal Hardware?The realistic path is acquisition. AMD has been rumored for a decade. Or can Microsoft time it right when hardware’s importance fades?This will be the biggest bet of Nadella’s career.AppleApple already has four spots on the bingo card.Internal Hardware in Apple Silicon. Operating System in iOS, macOS, and Apple Intelligence. End-User Hardware in every device the customer touches. Applications in the Services bundle and Apple Intelligence features.Here’s what must be true for Apple.Apple has to solve for Power, Infrastructure, and AI user experience. Power and infrastructure are heavy capex businesses Apple has historically avoided, so Apple buys power on the grid. Apple leases compute from AWS and Azure.Apple has to own the inputs they currently rent.The biggest risk to Apple is in AI experience; Apple sucks. Think about the difference between Siri and ChatGPT or Claude. It’s a joke.And experience is what Apple has historically been awesome at.On Monday, June 8, they finally announced Siri AI as part of the iOS 27 September software update.Their saving grace might be their hard stance on privacy, which is a credit to Tim Cook. His missional stance on privacy has built massive trust with consumers. If and when AI models can shrink enough to use less power and work on end-user hardware, Apple might be able to dodge their missing spots on the bingo card.AlphabetAlphabet has five spots on the bingo card.Internal Hardware in TPUs. Infrastructure in GCP. Operating System in Gemini and Android. End-User Hardware in Pixel and Nest. Applications in Gmail, Workspace, YouTube, Maps, Search.Here’s what must be true for Alphabet to win.Alphabet has to solve for Power, like the others. They also have to prove Internal Hardware is more than just a blip. Gemini has to integrate deeply into Gmail, Workspace, Search, Maps, and Android faster than AI cannibalizes the ad business that funds everything else.But they have what it takes. They have the cash flow to solve Power. They have the user base for the layers closest to the customer. They have the data to train the best models.The risk is internal. Alphabet’s organizational physics make speed hard.MuskonomyMusk theoretically has all six spots on the bingo card.Power in Tesla Energy via solar panels, batteries, and mega-pack batteries. Internal Hardware via AI4 and AI5 chips for Teslas and eventually Optimus. It is doubling down in Internal Hardware via its upcoming Terrafab investment as they build their own chips. Infrastructure in Colossus. Operating System in Grok and FSD. End-User Hardware in Tesla cars, Optimus, Starlink satellites, and Starlink terminals. Applications in FSD, Optimus, and the Macrohard concept.The only entity in tech history covering all six layers.Here’s what must be true for Musk to win.The clock is ticking as Musk has to execute M&A under a favorable White House. Tesla and SpaceX are strongly rumored to merge. Musk wanting to put all of his companies together is a major driver of the SpaceX IPO. The three companies have to stay coordinated under one strategic umbrella, even though they have different cap tables and different boards.While Tesla is a $100 billion revenue company and SpaceX has been cash flow positive for a decade, none of it is throwing off the free cash flow of an Alphabet or Nvidia.And Musk has to survive himself. This is a massive keyman risk, given his penchant to say what he thinks regardless of controversy.The Ultimate Game of ThronesThe AI era is the ultimate mega category game of thrones. Eight players. Six layers. Five principles from history and one open layer at the bottom of the stack. One throne.Here is what to do about it.The Career DecisionEveryone is fighting for layers two through six. Almost no one in the United States is fighting for Power. That is where the wide-open category space is. Whoever builds the company that figures out how to deliver gigawatts of clean, fast, permittable power for AI data centers becomes the category kingmaker for every other player in the matrix.This applies to careers across the stack. Take the job at the company that has a credible plan to solve Power, whether that company is a state economic development office in Tennessee or Mississippi or Texas, a nuclear startup, a distributed energy network, a grid operator, or one of the bingo contenders investing in their own generation.The talent shortage in Power is enormous.The category potential is enormous.The competition is thin.Run away from anything that has one layer and a great story. Intel was the best-performing tech stock of 1995. Nvidia is the best-performing tech stock of 2024 and 2025. One of those statements aged badly. The other one is sitting on a pattern that says it will too.And remember. All of this analysis could be wrong. We’re providing the category lens to a discussion about the potential for who will be the biggest winners, in a business media landscape that is ignorant of how market categories work.The Creator Capitalist MoveLearning how to invest (money, time, and intellectual capital) wisely in this Game of Thrones can extend your financial capital. And open the aperture of your thinking about the future.Solving problems across the value stack is worth its weight in gold.Look at the gaps in the matrix.Power is wide open.Infrastructure outside the hyperscalers is contested.Operating Systems belong to a handful of giants, but the categories that ride on top of those operating systems are wide open. The Creator Capitalist white space is in the categories Wall Street has not named yet.Build a category that requires AI but is not defined by it. Do not build an AI app. Build a category that an AI application is one expression of. Whoever languages a new category that lives in the matrix gaps gets to be the next Microsoft. The compounding from getting that right is bigger than anything else you will do with your career or your capital.The Speculative Capital QuestionIf you are thoughtful about picking the next Category King, you can live like a king.If you are already invested in the S&P 500, you are already invested in AI Category Kings. The matrix proves the point. Apple, Microsoft, Alphabet, Meta, Nvidia, and the rest of the top names sit inside the S&P 500. They are most of the index. The S&P 500 is the most boring and reliable way to participate in the AI era. Buy. Hold. Forty years from now your $10,000 looks like Microsoft money. Probably not Microsoft money. But it looks like a winning lottery ticket someone left on your desk.Don’t forget.The S&P 500 has a median return of 13.1% over the last 50 years.If you want a little more juice, QQQ works. The Nasdaq 100 overweights the technology names that win eras. Same companies. Higher concentration. Same buy-and-hold thesis.19% is the median return of the QQQ since its 1999 launch.If you have speculative capital, use your category design brain to figure out the top three companies that will get to bingo. Look at the matrix. Find the companies with five or six layers, or a credible path to five or six layers. Make your call on which one will own Operating Systems plus the layers closest to the customer. Make your call on which weird M&A or JV moves first. Make your call on which solo player gets acquired and at what price. Make your call on whether Muskonomy stays coordinated under one strategic umbrella long enough to claim bingo.The Category Kings will be the players who fill out the most valuable rows.We’ll be back with another episode next week.Hey Ho, Let’s Go!Arrrrrrr,Category PiratesEddie YoonChristopher LochheadP.S. Do you like our Deep Dive Reports? Why or why not? Please let us know on LinkedIn and Substack notes.P.P.S. Do you like the name Deep Dive Reports? Should we call it PSJ DDR? Dance Dance Revolution?

The University of Michigan consumer sentiment index just came in at 44.8.The lowest reading in the history of the survey.April was already the worst on record. We beat it, then beat it again a month later.Near-zero unemployment. Record-high stock market. GDP growing. Entrepreneurship at an all-time high.And the consumer says this is the worst they can remember.Something doesn’t add up.Here’s what we covered in this episode:1. “Record low” is good news.The consumer isn’t behaving like the survey says.Nobody’s broke and curling up in a ball.They’re getting smart. Waiting longer to buy a car. Buying less packaged food. Trading stuff for experiences.Because the real issue is not the consumer ‘income statement’. The real issue is the consumer ‘balance sheet’ is bloated and designed for a nuclear family that is declining.* Single family homes that are too expensive and too much space for single people.* Big cars sold for families that aren’t being formed.* Groceries to cook in a DoorDash world.The old linear life script is dissolving. Get married, get the house, get the promotion, collect your Scooby Snacks of purpose along the way. When that script breaks, people go find meaning on their own terms.2. The synthetic customer, and the race to beige.Bain published “Synthetic Customers Earn Their Stripes.” AI-generated buyers, backtested against a real conjoint study, replicated about 90% of the outcomes. Which features drive choice. Which products to launch. Even early price sensitivity. Target and US Bank are already testing on synthetic audiences before anything ships.The technology is a huge unlock.Sadly most companies will use it the wrong way.Everybody builds one. Everybody aims it at the fat part of the bell curve. They optimize the average customer into the ground and call it insight.Synthetic customers trained on average consumers makes us all dumber. We have an opposite POV…check it out.3. The triple wasn’t good enough.The QQQ is up around 600% over ten years, roughly 21% a year. The S&P did 13 to 14%. To get rich, you just had to sit still.Gen Z isn’t sitting still. A third have played prediction markets, a third hold crypto, and a quarter of their portfolios sit in non-traditional assets. The punchline: roughly 69% of Polymarket accounts have lost money since 2022.The FOMO flipped. A triple every year for a decade, and a whole generation said, not good enough, I want the fences.Why swing that hard? 9/11, then 2008, then COVID, each one before they could legally drink. When every safety net detonates that early, “wait 40 years” sounds naive.What’s coming up on Pirate Street JournalThree weeks a month, we drop the video. Three topics, thirty minutes, one cowbell.Once a month, we publish a written deep dive, the kind of category analysis you cannot get anywhere else. That one is for paying subscribers only, monthly and founding.Next week, we’ll be publishing a deep dive.Two ways to climb aboard now:Monthly subscriber: $20/month. You’ve done dumber things with $20.Founding subscriber: $375/year. For about a dollar a day, you get every mini-book we’ve ever written (300+), every audiobook (30+), digital copies of all seven of our Big Books, and unlimited access to The Pirate Eddie Bot and Pirate Christopher Bot, your 24/7 AI jamming partners for category building.Subscribe today, get the next deep dive the day it drops, and start jamming with the bots.Recorded Friday, May 29. Every number above is as of that morning.Piratey disclaimer: This is NOT financial advice. None of us have a Series 63, Series 7, Series 6, CPAs, CFAs, IUDs, IEDs, and hopefully not IBS (this makes DUDE Wipes sad).Stay tuned for next week’s episode.Hey Ho, Let’s Go!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/subscribe

Jennifer Hall Thornton has a PhD and a law degree. Her kids’ friends call her Dr. Doctor.She ran the everything-but-sales side of a digital company while raising two kids thirteen months apart, with an elderly mother nearby and a husband who lived on a plane. She was in the first Academy cohort, before anyone could tell her the timing was right. She told them the timing was right.She is also an Agentic Mom.Jennifer built a set of Claude skills that logs into her kids’ college Canvas, checks for anything new, downloads it, summarizes it, emails them, and then builds practice quizzes from the material. She built it for herself first. Then she shared it with her 18 and 19-year-olds.The agentic mom is agentifying her children.A mother who learned to delegate the donkey work of her own life to AI agents, looked at her kids drowning in logins and busywork, and decided they did not need to be good at the stuff she had to be good at to survive school.Pirate Jennifer did not raise her kids to be the best version of her. She is consulting them into the best version of them.Most parents try to clone themselves. They want the kid to do the thing they did, or the thing they wish they had done.Pirate Jennifer did the opposite, and she did it before Creator Capitalist gave her the words.She made her kids write thank-you notes. Three a year, starting in third grade, one for each year of school by graduation. Both kids wrote far more than required.Her son’s handwriting is unreadable, and his fourth-grade teacher still messages him two years out of high school because he wrote her a note. Her daughter emailed a high school neuroscience teacher as a college freshman because something he taught her showed up on a biology midterm her professor never covered. He wrote back inside the hour.That is relationship capital, built by a nine-year-old and ten-year-old, compounding for a decade.The dinner table was a debate where you had to keep up no matter your age. That is intellectual capital. Showing up late, turning in sloppy work, going to office hours because you are actually curious, all of it builds reputation capital.She taught the four capitals before her kids could spell them.Then Creator Capitalist came out, and Jennifer read it and thought, well, duh. She had been running the flywheel the whole time. She finally had the languaging for it.She told us that Creator Capitalist starts thirty years earlier than we thought.We wrote Creator Capitalist for adults. Mid-career or later, people who have already built some of the four capitals and are looking for what is next.Jennifer read it and started talking about how the frameworks were for her teenagers. In her velvet-hammer way, she told the donkeys to look again.Creator Capitalist is for kids, too.She is right. The four capitals are a flywheel, the same compounding engine that Christopher teaches young people about money. Except it starts spinning at 19 instead of 50.Tell a 19-year-old they have no intellectual capital, and they will believe you.Pirate Jennifer calls BS.Intellectual capital is not the diploma. It is how you approach a problem, and what your friends come to you for.Her son is a poli-sci major who taught himself to run every machine in the engineering lab, became the TA for a course only engineering students are allowed to teach, and got paid for it. He applied to twelve colleges and got into twelve, with no sports and no titles, because he was different and had a story to tell.That is a Creator Capitalist, two years out of high school.Her daughter Emily is studying biochemistry at UT Austin. She loads every note and slide into a Claude project and has Claude teach her, write quizzes, grade them, then build new quizzes targeting only what she is getting wrong.Before her last exam she asked Claude for the hardest questions it could write. When the professor found one Claude missed, she fed it back and told Claude it blew it.She is co-creating her education with AI, then taking it back into the traditional system and winning. Her friends say it is too complicated.They are going to regret it.Here’s how to navigate this conversation:* 06:01 – Parenting in the age of AI: Pirate Christopher opens by asking what it is actually like to raise an 18 and 19-year-old right now, and why Jennifer is a far better parent to young adults than she was to little kids.* 11:09 – The book whack: How Jennifer told Category Pirates that Creator Capitalist, the book they wrote for mid-career adults, is really a curriculum for teenagers, and why they did not see it coming.* 11:44 – The thank-you note machine: Three notes a year starting in third grade, the fourth-grade teacher who still writes back, and relationship capital built by a nine-year-old.* 14:34 – The poli-sci grease monkey: The son who got into all twelve colleges he applied to with no sports and no titles, then became the engineering lab TA he was technically not allowed to be.* 22:55 – The flywheel at 19: Why the four capitals are the same compounding engine Christopher teaches kids about money, except they start spinning thirty years earlier.* 33:07 – “I call BS”: Jennifer dismantles the myth that young people have no intellectual capital, and explains what intellectual capital actually is.* 34:44 – The agentic mom agentifies her kids: The Claude skill that logs into Canvas, summarizes new material, and builds quizzes, and the moment Jennifer realized she should hand it to her children.* 39:26 – AI in the classroom: Why banning AI is the wrong move, what counts as cheating versus co-creating, and the World Book Encyclopedia parallel.* 42:01 – Teaching Claude to teach you: Emily’s biochemistry workflow, the hardest-quiz challenge, and the Feynman technique applied to an AI.* 46:33 – Build a bot, sell it to your friends: Eddie on why a college kid should build an O-chem TA bot, charge classmates fifty bucks, and learn the material better in the process.* 53:15 – The Dickens exercise: If 18-year-old Jennifer were starting today, loving to learn and unafraid to fail, what would she build.* 01:04:19 – Start with relationship capital: Why young people should start the flywheel with the capital they already have, and how to find the intellectual capital you do not know you own.We were not wrong about Creator Capitalist. Jennifer just showed us it starts earlier than we thought.The framework does not care how old you are. It cares whether you get the flywheel spinning before everyone else does.Jennifer did it intuitively, over fifteen years, without the words. She raised two Creator Capitalists, then spent this conversation reverse-engineering how she pulled it off.Imagine what that compounding looks like for a kid who has the framework AND the next twenty years ahead of them, instead of behind them.Whether you are the parent or the kid, the work starts the same way.Get the agents running. Get the flywheel spinning. Stop doing the donkey work a machine can do, and spend the time you save building the four capitals nobody can take from you.Arrrrrr,Category Pirates 🏴‍☠️Eddie YoonChristopher LochheadP.S. The fastest way to start agentifying your own life (or your kid’s).Pirate Jennifer built her agents alone, a step or two ahead of everyone around her. You do not have to.Become a Founding Subscriber and you get access to The Pirate Eddie Bot and the new Pirate Christopher Bot, the fastest way we know to put the four capitals to work in your life, your career, and your kids’ education, without waiting for permission from a school that still thinks AI is cheating.→ [Become a Founding Subscriber to get access 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

Anthropic is paying SpaceX $1.25 billion a month for compute.Every month through May of 2029.Roughly $45 billion total.That single contract is bigger than SpaceX’s entire annual revenue today.Software is paying hardware. Hardware is paying energy. Energy is paying space.Is it three card monte?Or is the pie getting massively bigger?This should be on every business news front page this week. Instead, the headlines are about Sam Altman’s house getting attacked, Eric Schmidt getting booed off a stage, and OpenAI quietly leaking that it might file for an IPO too.Here’s what we covered in this episode:1. AI gets an F in marketing.360,000 Americans are in Facebook groups organized against data centers. AI is polling less popular than ICE, less popular than Trump, less popular than politicians.The technology being protested is curing diseases and driving much of US GDP growth.So why are so many angry at AI?Pirate Eddie has a theory, and it does not involve AI at all.Marriage rates. Birth rates. Teenage drinking. Labor force participation among young men.All down.Life stages and zest for life as we know was crumbling before AI.2. SpaceX is going public. The TAM is the size of the American economy.The S-1 is pitching a $28.5 trillion total addressable market.U.S. GDP is $32 trillion. SpaceX is asking public markets to fund a business roughly the size of the entire American economy, run by a CEO whose vesting schedule requires interplanetary colonization.Imagine being on the dock before the Nina, Pinta and Santa Maria set sail and you were offered a chance to invest in the new world.What was the ROI on America?What if you had a chance to invest in Space?But the history of IPOs is that retail investors get hurt.The history of Elon Musk is that betting against him is also expensive.The Pirates how category designers think about an IPO this size without losing your mind or your savings.3. The category queen vs. the category queen.The fastest-growing company in the history of business is not OpenAI.It is Anthropic.Anthropic was founded by people who left OpenAI. They are now in talks at $900 billion. Higher valuation. Higher growth. First profitable quarter ever at $11 billion in revenue.Andrej Karpathy, founding member of OpenAI and the man who coined vibe coding, just joined Anthropic. Ross Nordeen of xAI joined Anthropic earlier this month. The defectors are recruiting the defectors.Category Design 101 says the queen takes 76% of the economics. Everyone else shares 13%. So which one is the queen?Pirate Christopher has a frame on the video that recasts the entire question. He thinks this is not OpenAI versus Anthropic at all.This is the (new) Pirate Street Journal.Every Wednesday, we pick three headlines worth paying attention to and break down the category underneath.Three Wednesdays a month, the video is free (for now). Once a month, we drop a written deep dive for paid subscribers, the kind of category analysis you cannot get anywhere else.Two ways to climb aboard:* Monthly subscriber: $20/month. You’ve done dumber things with $20.* Founding subscriber: $375/year. For about a dollar a day, you get every mini-book we’ve ever written (300+), every audiobook (30+), digital copies of all seven of our Big Books, and unlimited access to The Pirate Eddie Bot and Pirate Christopher Bot, your 24/7 AI jamming partners for category building.To never miss a deep dive, become a subscriber today.What’s coming up on Pirate Street JournalA few of the threads from this week’s episode are running headlong into a much bigger story, which is the IPO season that is about to define the next decade of public markets.On June 10th, two days before SpaceX is estimated to start trading, we are publishing the next PSJ written deep dive. We will be working through how a category designer thinks about investing in an IPO of this scale, what the category math says about SpaceX, OpenAI, and Anthropic going public in the same window, and we don’t know what the headlines will do between now and then, so there will be more.Piratey disclaimer: This is NOT financial advice. None of us have Series 63, Series 7, Series 6 7, CPAs, CFAs, IUDs, IEDs, and hopefully not IBS (this makes DUDE Wipes sad).Stay tuned for next week’s episode!Hey Ho, Let’s Go!Arrrrrrr,Category PiratesEddie YoonChristopher LochheadP.S. - Founding subscribers get every mini-book we have ever written (300+), every audiobook (30+), digital copies of all seven Big Books, and unlimited access to The Pirate Eddie Bot and Pirate Christopher Bot, your 24/7 AI jamming partners for category building for about a dollar a day. You have done dumber things with a dollar a day.👉 Become a founding subscriber. 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 free preview of a paid episode. To hear more, visit www.categorypirates.newsLast week, we recorded the very first episode of the Pirate Street Journal.The Pirate Street Journal is for leaders with a different mind.A different take on business news.Through the category lens.Our mini-books are timeless. PSJs are timely.Our mini-books are long stories longer. PSJs have 30-minute seat belts.Our mini-books are thinker’s high. PSJs try to help you think before you act.But, but, but, but…Piratey disclaimer: This is NOT financial advice. None of us have Series 63, Series 7, Series 6 7, CPAs, CFAs, IUDs, IEDs, and hopefully not IBS (this makes DUDE Wipes sad).Think of this like professional wrestling. It’s entertainment.Don’t be so smart, you’re stupid and suplex your safety net savings.Hey Ho, Let’s Go!PSJ is the new weekly thing. The video’s free. The deep-dive written analysis is paywalled. Watching makes you informed. Reading makes you different.Two ways to climb aboard:* Monthly subscriber: $20/month. You’ve done dumber things with $20.* Founding subscriber: $375/year. For about a dollar a day, you get every mini-book we’ve ever written (300+), every audiobook (30+), digital copies of all seven of our Big Books, and unlimited access to The Pirate Eddie Bot and Pirate Christopher Bot, your 24/7 AI jamming partners for category building.To read this week’s deep dive, become a subscriber today.1. Why is Salesforce down? Why is Micron up?The Mag 7 reported earnings, and they were great overall.But here’s some weird data.Salesforce (one of the Category Kings of SaaS) lost about a third of its market capitalization in the last 12 months, despite strong revenue and operating income. Forward P/E down 28% in twelve months. Benioff just announced a $50 billion stock buyback, one of the largest in corporate history.Micron (memory for AI) saw over a 6x increase in its stock price in the last 12 months, also with incredible revenue and operating income. Forward P/E sat at roughly 3x a year ago. Today it is over 7x. The stock more than tripled in that window, but earnings grew faster than the multiple did.In the columns, we have the Mag 7, plus SpaceX, which is soon to go public, as well as Micron and Salesforce.The rows are what matter.* Top row, Potential investors. Forward P/E above roughly 27, which is about +5 above the S&P 500 average PE multiple.* Middle row, market-average band. Forward P/E is roughly 17 to 27. The S&P 500 lives here at around 22.* Bottom row, Performance investors. Forward P/E below roughly 17, which is about -5 below the S&P 500 average PE multiple.The actual PEs are merely a placeholder, as there’s nothing magic about plus or minus 5 from the S&P 500 average.We want to discuss the fact that there are two types of investors.Performance investors. They invest in companies because of their current and near-term performance. Their performance is predictable, reliable, and steady. Sometimes slow, but never surprising. These are usually Category Kings today.These companies are valued at lower multiples, whether it is price to earnings, enterprise value to EBITDA, or price to sales.And there are Potential investors.They invest in companies regardless of their performance now or in the near term, but in their long-term future potential. Usually, these are companies that can become future Category Kings that no one else really sees.These companies are valued at much higher multiples, usually because earnings or sales are emerging and expected to accelerate.When Potential investors start buying a stock, they lift the forward PE multiple as they are willing to pay a premium for potential. They think the category size of prize is growing and has huge upside.They think the category is on the good side of the S-curve. All boats rise with the tide.When Potential investors sell a stock to Performance investors, it depresses the forward PE multiple because they aren’t willing to pay a premium for potential. They think the category size of prize is static and has limited upside.2. Are you on the good or bad side of the s-curvePerformance vs. Potential investors are fundamentally debating one fundamental question.Is the category and company on the good or bad side of the S-curve?You don’t have to be right on the precise number and date. It’s not like picking black 17 on the roulette table.It’s just picking black or white. Using data and Category Design. And thinking about thinking.You don’t have to predict timing. You don’t have to predict a number. You should, but don’t have to, do fancy analysis.Left or right of the S-curve is the question.If you are right, and everyone agrees with you, it can be a profitable bet.If you are right, and everyone disagrees with you, you can create generational wealth.But you have to be comfortable with the loneliness, name-calling and mockery that comes with rejecting the premise.When Pirate Eddie wrote in HBR that Netflix’s 80% stock drop in 2011 was Wall Street being dumb, Wall Street called him dumb. When Pirate Eddie shared on CNBC about Tesla’s superconsumer being a new superconsumer who valued both functional and fun cars, Wall Street called him dumb again.When Pirate Eddie wrote in HBR that General Mills should sell its cereal business, he made a lot of former clients/friends at General Mills angry. But the data at the time was undeniable. 12 years of category decline. And unless you believed carbs and sugar were ever coming back into vogue, General Mills’ cereal business would never be more valuable than it is today. And they should sell it.General Mills’ stock is down 38%, while Kellanova (old Kelloggs with cereal spun out) is up +4% since being acquired by Mars. General Mills’ PE ratio is 8x, and Kellanova’s PE is 23x.Sometimes being right doesn’t feel great at first.But the cost of being legendary is the willingness to be different.3. Re-rating is a result of Category DesignRe-rating is when Wall Street decides a company’s multiple should be higher or lower.Revenue, gross margins, and cash flow don’t change. The value of those economics does.Everything we value, we’ve been taught to value.Re-ratings are simply a redefinition of the Category.Did you know Domino’s Pizza was the 2nd best performing stock from 2010 through the end of 2019?Why? It transformed from a pizza delivery company to a tech company that happens to deliver pizzas. They invested heavily in their ‘pizza tracker’, apps, and frictionless mobile apps.It’s Category Design 101.And if you invested $1,000 into Domino’s at the beginning of 2010, you’d have $40,000 in 10 years.The best part is that re-ratings can happen slowly. You could have jumped on the Domino’s train any of the first 9 years of its run and done well.Wall Street is often blind to Category Design.Category Design is your unfair advantage.4. The SaaSpocalypse is overstatedThe financial press has decided this is the death of software. Salesforce down $135 billion. ServiceNow down $100 billion. Workday down $50 billion. Hundreds of billions of dollars in enterprise software market cap gone in a year.It is the wrong frame. Software is not dying.On May 15, Marc Benioff sat down with the All-In Podcast and said,“… the software market’s rerated. It happens every now and then. There are cycles. You know, I’ve been doing Salesforce for 27 years, enterprise software for 40. And the market’s rerated.”— Marc BenioffThe earnings are fine, but the multiples got cut.Salesforce guided to do $46 billion in revenue and $16 billion in cash flow this year. Performance is not the problem.Potential is.The market used to price these companies as Potential plays. Software is eating the world, every business needs a CRM SaaS, the seat count never stops growing. That story matured. The category got knowable. The TAM became visible. So the market quietly moved these names down a row. From Potential. To Neutral. Some all the way to Performance.Benioff is responding to this exactly the way a category designer should. He is doing three things in parallel. Buying back stock at compressed multiples because he believes the business is worth more than the market pays for it. Acquiring companies (Informatica), while, in his words, “everything’s a little cheaper.” And, most importantly, repositioning Salesforce out of the SaaS category entirely. AgentForce. Slack as the context engine. Humans, agents, and headless platforms interoperating.If that repositioning works, Salesforce gets re-rated up again under a new category label. Same business. Different multiple. Different shareholders. That is the move.4. AI hardware is more valuable than AI softwareThe content in this section is 100% created by AJ on X @alojoh.He’s a former Goldman Sachs investment banker, who built his own pirate ship that is a combination of investment research and trading advice with a rare alignment of incentives with his subscribers.The goal of equity research is to drive trading revenue for investment banking, not necessarily at the benefit of the reader of the research. There is a strong motivation to put out positive news and analysis for investment banking clients and even stronger reluctance to say anything negative about those same clients. It is not 100% trustworthy.The incentives for most traders/investors is to grow their own returns, even at the expense of subscribers/readers. They may tell you to buy a stock, but only after they bought it, and at times, they sell as they tell you to buy. Or their incentive is to grow their assets under management and charge you 2% of assets and 20% of carry for as long as possible.AJ is the odd combination of a top-tier investment researcher who uses it to trade for his own account. His basic subscription on X is only $7/month, but his hardcore channel is $500/month, which Pirate Eddie subscribes to and has already generated more than a 20x ROI on the cost of the annual hardcore subscription. Sign up if you like buried treasure.AJ is a pirate who routinely rejects the premise. This section is a synthesis of his insights and work and is shared with his permission.One of the most provocative quotes from AJ is, “Hardware is the endgame” for AI.For decades, software economics have always trumped hardware economics.In the age of AI, it’s no longer always true.Eighteen months ago, the DRAM memory industry was effectively left for dead. Post-COVID demand had snapped back. Customers had massively over-ordered during the shortages. The industry was working through an enormous inventory overhang. Prices collapsed. The major players took huge losses. Standard semiconductor cycle. Standard low-multiple memory business.Then the AI buildout happened underneath them. In two or three months, the entire setup will be inverted. Utilization went from roughly 20% to over 100%. Hyperscalers moved into “whatever it takes” pricing mode on memory. Long-term supply agreements got locked in across the three major players (Micron, Samsung, SK Hynix) who together produce roughly 95% of global DRAM.Memory used to be a commodity. Now it is AI infrastructure.The cleanest way to show you why is to put Micron next to the most darling AI software stock on the public markets right now. Palantir.* Revenue growth (year over year). Micron +196%. Palantir +85%.* Operating margin. Micron 67.6% (GAAP). Palantir 60% adjusted, 46% GAAP. Yes, you read that right. The memory chip company has a higher operating margin than the AI software company.* Rule of 40 (revenue growth percent plus operating margin percent). This is an awesome rule of thumb. If you want to know if a business is healthy or not, just take their revenue growth percent and add it up with their operating margin percent. If both are greater than 40%, you have a great business. Per Palantir’s own Q1 2026 investor deck, Micron sits at 265%. Palantir sits at 145%. Palantir is literally publishing slides that show Micron crushing them on the metric they brag about.* Forward P/E. Micron roughly 7x. Palantir roughly 95x. Palantir trades at a multiple thirteen times higher than Micron, while growing slower, earning lower margins, and scoring lower on its own framework of choice.This AI hardware company has the better business by every operating measure. The software company has the better multiple by every valuation measure. That is what a re-rating up looks like when it is not yet complete on one side and what a Potential premium looks like when it might be ahead of itself on the other.This does not mean Palantir is doomed. It means the gap between the two multiples is going to close.5. The Mag-7 will be the Mag-10. Abundance will followWe are not telling you software is over.Anthropic and OpenAI will do extraordinarily well. Pirate Christopher made the call on the pod. These are the largest, fastest-growing companies ever created, sitting in private markets at scale that exceeds most of the Mag-7. They are the leadership of the next decade of AI software. When they go public, the math changes for everyone.But the SaaSpocalypse is more about the rise of AI hardware and hardware in general. This is why Micron is exploding. And why SpaceX is about to launch the largest IPO in history.The Mag-7 framing is already obsolete. Three names belong in the group that are not in it yet, and the math suggests all three of them get added inside the next twelve months.* OpenAI. Created the fastest-growing category in startup history. Reported to be exploring an IPO window.* Anthropic. Became the fastest-growing company in history. Already operating at a scale that exceeds most public Mag-7 members on the metric that matters most, category formation speed.* SpaceX. IPOing in June. Already cash-flow positive thanks to the Colossus lease deal with Anthropic, and reportedly being talked about at $1.75 to $2 trillion.And it does not stop at ten.Stripe could be next. The private IPOs of the last decade are starting to unwind. Every name that has been trapped in private markets at Potential multiples is about to become available to public investors who have been starved for Potential exposure.One more thing the matrix hints at.There is still no energy company in the Mag-anything bucket. Tesla is sometimes pitched as the answer because of its solar and battery business. The actual AI energy story is coming.There is a real chance we are entering one of the largest equity bull markets in modern history, and most professionals are still positioned for a recession that did not happen.Global GDP in 1926 was about $3 trillion. Today it is roughly $126 trillion. That is a ~50x expansion of human-created value in 100 years.The mechanism was not “stocks went up.” The mechanism was that humans kept designing new categories that created value from nothing. Refrigeration. Electrification. The semiconductor. The internet. Each of those was, in its moment, an abundance boom. Each one looked like a bubble in the middle innings. Each one was actually a re-rating of the entire economy onto a new S-curve.If AI is the next one, the abundance argument runs like this:* The S&P 500 goes up because the Mag-10 carries it. The top names are already a huge share of index weight. When they re-rate up, the index does too, almost mechanically. This is already happening.* The Nasdaq goes up more, because both the AI hardware layer and the AI software layer live inside it. Hardware re-rates up. Software re-sorts. The up names are bigger than the down names. Net positive.* Productivity finally shows up in the data. If even 30% of the AI productivity case is real, US GDP growth surprises to the upside for years. That is the macro backdrop bulls have been waiting for since the 1990s.* The Potential investor pool expands as more capital chases the abundance narrative. More Potential capital, chasing the same names, pushes multiples higher. The re-rating accelerates.If we are right about the abundance boom, the index investor does well. The Performance investor does fine. The Potential investor does great.But the category designer wins differently. The category designer wins by spotting re-ratings, in both directions, before the analyst class can model them.All of this boils down to two questions.* Is the category on the good or bad side of the s-curve?* Is the risk of staying the same greater than the risk of changing?If you can answer those questions honestly about your business, your career, your portfolio, your category, you could create a massive outcome and avoid sailing into rocky waters.Arrrrrrr,Category PiratesEddie YoonChristopher Lochhead

“Bet on yourself sooner” is the most popular piece of career advice on the internet.It’s also the most useless.Nobody who says it tells you what to bet on. So most people hear it and do the obvious thing. They bet harder on the most visible capital they already have. They chase a bigger title. A bigger paycheck. A bigger brand name on the resume. They mistake “betting on yourself” for “doubling down on what other people already validate.”Then they wonder why nothing compounds.Linda Deeken did the opposite for twenty years.And it’s the reason she can run her own thing now with more leverage than most of the partners who once outranked her. Five kids. Two sets of twins. A daughter with Down syndrome who also beat cancer. A husband with his own career. A solo consulting practice (Deeken Strategies) that out-earns most W-2 partners. A returning client roster that calls her because she “makes them better.”She built all of that by quietly betting on the two capitals nobody could see.Reputation and financial capital are visible.That’s why most people chase them. You can see the diploma. You can count the comp. You can ride them into the next room and let the room react.Relationship capital and intellectual capital compound silently. There is no certificate for the fifteenth time a client said “you make me better.” Nobody throws you a parade for refining your point of view in the margins of someone else’s slide deck. The work is real, the leverage is real, and the compounding is real. None of it is legible to the people watching.Linda spent twenty years building the two capitals nobody could see her building. By the time she launched Deeken Strategies, the math was lopsided in her favor. The reputation and the financial returns came roaring in because the other two had been compounding the whole time.That is the actual lesson. Bet on the right capital sooner.Four moves that looked like sidesteps and were actually compounding.Linda turned down Stanford for UW Madison at 17. Her father was older, her mother had her at 43, and her family needed her closer. She traded the diploma everyone in her future networking room would have recognized for time with people who would not be around forever. Relationship capital up. Reputation capital sacrificed.She left Mercer for The Cambridge Group. Mercer had the bigger brand. Cambridge had the female partners, the better operating model, and the path that would actually let her become both a serious consultant and a mother. Reputation down. Relationship and intellectual capital up.She went to Miller for a year, had her first set of twins, then came back to Cambridge as a CMO, not a partner. Title down. Writing muscle up. The CMO role forced her to develop her own point of view instead of executing other people’s frameworks. That’s the season most consultants never get. It’s also the season that built the intellectual capital she now monetizes on her own.She launched Deeken Strategies before she had the permission slip she wanted. By her own admission, that was the bet she wishes she had made sooner. She could only make it because the first three bets had already loaded the dice.Her superpower is the outcome other people get when they work with her.The way Category Pirates defines a superpower is different from how most people do it. Most people would say a superpower is what you’re good at. We say a superpower is the outcome you produce for others that you are best known for.Linda’s clients describe her in three words: smart, humble, oriented to your outcomes.That combination is rare on its own. It’s rarer still in someone running a household of seven. And it’s the languaging she earned by writing, by refining her POV through the CMO season, and by treating every client engagement like a long-term relationship instead of a short-term transaction.She runs her household the same way she runs her client work. She has a SWOT analysis for each of her five kids. Strengths, weaknesses, opportunities, threats. She is not parenting her kids to become the best version of her. She is consulting them into the best version of them.This is what integration actually looks like. The work feeds the parenting, the parenting feeds the work, and both halves get sharper because the same operating system is running underneath both.Here’s how to navigate this conversation:* 05:17 – Turning down Stanford at 17: The first time Linda chose relationship capital over reputation capital, and why she never built her identity around the diploma she didn’t get.* 12:23 – Chemical engineering as a consulting prep school: Why studying the hardest thing makes the easier things easier, and why “learning the lingo” is the first move in building intellectual capital.* 18:55 – Leaving Mercer for Cambridge: Trading the bigger brand for the operating model that would actually let her become both a serious consultant and a mother.* 25:12 – The Miller detour: One year in corporate, a set of twins, a move to Milwaukee, and what she learned about herself in a job she didn’t love.* 26:35 – The CMO role she designed: How Linda built a returning role at Cambridge that gave her flexibility AND forced her to develop a POV instead of executing other people’s frameworks.* 29:08 – “Put me in coach”: The moment the CMO role stopped being enough and Linda launched Deeken Strategies.* 45:53 – Smart, humble, oriented to your outcomes: The three-part combination that became Linda’s superpower and the languaging her clients use to refer her.* 49:38 – Children as consulting projects: The SWOT-per-kid framework, why she rejects the “I want my kid to do what I never did” trap, and what Sarah is teaching the whole family.* 1:04:19 – Own your own future, fearlessly: Linda’s closing convict to every woman watching from the sidelines.What Linda is doing is not a one-off.It’s a pattern.The same pattern Creator Capitalist documents end-to-end. Bet on relationship and intellectual capital first. Develop your point of view. Find the work that builds your four capitals at the same time. And then, when you can’t bear NOT to bet on yourself any longer, bet.She did it intuitively, over twenty years, without the framework. Imagine what that compounding looks like when you have the framework AND the twenty years ahead of you instead of behind you.Connect with Linda:* Follow her on LinkedIn hereArrrrrr,Category Pirates 🏴‍☠️Eddie YoonChristopher LochheadP.S. The fastest way to figure out which capital you’re under-betting on.Linda did this work over twenty years, mostly alone, by writing in the margins and pressure-testing her own thinking against clients who became friends. You don’t have to.Become a Founding Subscriber, and you’ll get access to The Pirate Eddie Bot and the new Pirate Christopher Bot. They will challenge your premise, sharpen your POV, and stop you from doing what most people do when they say they’re betting on themselves, which is just betting harder on the capital they already have plenty of.→ Become a Founding Subscriber to get access here. 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 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