Category Pirates

Category Pirates 🏴‍☠️
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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

  1. 2 HR AGO

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

    15 MAY

    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

    1hr 9min

  3. 13 MAY

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

    1 MAY

    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

    1hr 4min

  5. 22 APR

    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

  6. 22 APR

    Career Quakes Part 1 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 Most people think careers are built through planning. They’re not. They’re built through quakes. Unexpected moments that shake everything: Your job Your identity Your relationships Your sense of what matters You 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 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.

    7 min

  7. 22 APR

    Lightning Strike Legends 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 Most 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 POV Air War: Booth + live podcast creating visibility and credibility Ground 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 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.

    5 min
  8. How To Raise $50M Without Giving Up A Single Point Of Equity With Dr. Eric Hanson

    17 APR

    How To Raise $50M Without Giving Up A Single Point Of Equity With Dr. Eric Hanson

    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: eric@milmedconnect.com Arrrrrr, Category Pirates 🏴‍☠️ Eddie Yoon Christopher Lochhead P.S. — Eric didn’t become a category of one by accident. He took 17 years of military medical expertise, named the translation gap nobody else was solving for dual-use CEOs, and built an entire category around it. Bots, software, a Techstars accelerator, a trained army of veteran entrepreneurs. He’s also a Category Design Academy Cohort 3.0 graduate. Which means the frameworks he’s using to scale Navigator and train the next generation of military medical Creator Capitalists are the same ones we teach inside the Academy. Academy 4.0 applications close in 10 days. The next cohort starts in May. If Eric’s story resonates, if you’re sitting on a superpower the rest of the world hasn’t named yet, that’s exactly the work the Academy is designed to do. → [Learn more about the Academy here.] → [Apply here.] 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

    53 min
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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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  • Episodes
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