Category Pirates

Category Pirates 🏴‍☠️

5.0 (1)
Entrepreneurship
Updated Biweekly

The authority on category design, category creation & creator capitalism. Sharing how legendary entrepreneurs, executives, marketers, and creators design business breakthroughs. By Christopher Lochhead, Eddie Yoon, & Bri Clark www.categorypirates.news

3d ago

"Lowest Consumer Sentiment" Is Good News?

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 Journal Three 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 Pirates Eddie Yoon Christopher 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

38 min
May 29

How Jennifer Hall Thornton, An Agentic Mom, Agentified Her Own Kids

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 Yoon Christopher Lochhead P.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

1h 8m
May 27

Category Queen vs. Category Queen: Is OpenAI About to Get Dethroned?

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 Journal A 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 Pirates Eddie Yoon Christopher Lochhead P.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

39 min
May 22

The Great Re-Rating: Is the SaaSpocalypse Real?

This is a free preview of a paid episode. To hear more, visit www.categorypirates.news Last 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-curve Performance 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 Design Re-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 overstated The 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 Benioff The 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 software The 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 E

35 min
May 15

Why Turning Down Stanford Was The Best Career Move Linda Deeken Ever Made

“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 here Arrrrrr, Category Pirates 🏴‍☠️ Eddie Yoon Christopher Lochhead P.S. The fastest way to figure out which capital you’re under-betting on. Linda did this work over twenty years, mostly alone, by writing in the margins and pressure-testing her own thinking against clients who became friends. You don’t have to. Become a Founding Subscriber, and you’ll get access to The Pirate Eddie Bot and the new Pirate Christopher Bot. They will challenge your premise, sharpen your POV, and stop you from doing what most people do when they say they’re betting on themselves, which is just betting harder on the capital they already have plenty of. → Become a Founding Subscriber to get access here. 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

1h 9m
May 13

Happy first birthday, Pirate Eddie Bot.

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 Yoon Christopher 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

59 min
May 1

How To Mother Like A Creator Capitalist With 5 Moms Walking The Talk

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 LinkedIn Follow Pirate Alexis Skigen Rago on LinkedIn Follow Pirate Melissa Andrews on LinkedIn Follow Pirate Jennifer Hall Thornton on LinkedIn Follow Pirate Mary Kathryn Johnson on LinkedIn Arrrrrr, Category Pirates 🏴‍☠️ Eddie Yoon Christopher Lochhead P.S. — Mother’s Day is coming up. If you want to gift the mom in your life something genuinely valuable, or if you are the mom and you’re looking to start creating value of your own, the best place to start is with the Pirate Eddie Bot. It’s the fastest way we know to put the four capitals to work in your life, your career, and your relationships, without waiting for permission from anyone. → Become a Founding Subscriber to get access to the Pirate Eddie Bot here. 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

1h 4m
Apr 22

Career Quakes Part 2 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 Nearly 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 Yoon Christopher Lochhead PS: 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.

6 min

The authority on category design, category creation & creator capitalism. Sharing how legendary entrepreneurs, executives, marketers, and creators design business breakthroughs. By Christopher Lochhead, Eddie Yoon, & Bri Clark www.categorypirates.news

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Category Pirates 🏴‍☠️
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