Category Pirates

This is a public episode. If you'd like to discuss this with other subscribers or get access to bonus episodes, visit www.categorypirates.news/subscribe The world keeps betting against America. For 250 years, that's been the losing bet. Louis the Fourteenth ruled France for fifty-four years from a palace with seven hundred rooms and zero bathrooms. He commanded armies. He also lived in constant fe...

Here’s what we covered in this episode: 1. Microsoft is selling the business agenda, not the software. Microsoft launched a new company: Microsoft Frontier. $2.5 billion, 6,000 engineers, sent inside other companies to make their AI work. That is consulting. The highest-margin software business ever built just walked into one of the lowest-margin businesses in tech, on purpose. The stock is down a...

This is a public episode. If you'd like to discuss this with other subscribers or get access to bonus episodes, visit www.categorypirates.news/subscribe This mini-book is read to you by AI Pirate Eddie. (If reading is more your style—or you want to see all sources and GIFs— you can read the written version here. ) Most Americans have no idea how rare the country they live in actually is. Pirate Ch...

Here’s what we covered in this episode: 1. State Farm is fighting to keep the customers it should fire. Progressive just took the personal auto crown State Farm held since World War II. It sells more than half its policies direct. No agent. State Farm’s answer: fly 19,000 agents to Vegas, throw a Pink concert, then tear up their contracts. Sign a worse deal by 2027 or take a buyout. Gross income c...

SpaceX went public on a Friday. By Tuesday, it was worth $2.5 trillion, bigger than Amazon. Four days in, it spent $60 billion on a four-year-old startup. That startup was worth half as much in November. Wall Street called the price insane. The price is the least interesting thing about it. Here’s what we covered in this episode: 1. Wall Street says Musk overpaid for Cursor. We think it was a barg...

Gartner grew its revenue again last year. Investors wiped out more than $30 billion of its value anyway. The stock fell from $551 to $155 in about twelve months. Still profitable. Still growing. Still the name every CIO knows. Wall Street just stopped believing it has a future worth paying for. The business is fine. The future got repriced. Here’s what we covered in this episode: 1. Gartner grew r...

We loved celebrating all the moms in our lives a few weeks ago over Mother’s Day, and now it’s time to celebrate the dads. Before we get into the episode, we have something fun to share. The Parent Bundle and a Father’s Day offer This week we’re launching the Parent Bundle , and if you sign up as a new Founding Subscriber between now and Father’s Day, you’ll get the full bundle included at no extr...

This is a free preview of a paid episode. To hear more, visit www.categorypirates.news On June 12, SpaceX is going public at $135 per share and a $1.75 trillion valuation. 4% of total shares are being offered. Of those, 30% have been allocated for retail investors to buy directly at the $135 IPO price. The standard retail allocation in a mega-cap IPO is 5 to 10% of shares, with the overwhelming ma...

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...

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...

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....

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...

“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...

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 p...

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, a...

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. Th...

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 beco...

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 play...

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 t...

Welcome to Creator Capitalist Conversations, a series spotlighting Category Designers who have rejected traditional career paths and built lives around what makes them different. Our new book, Creator Capitalist , is available now. Get your copy here . Dear Friend, Subscriber, and Category Pirate, Most people think there are two kinds of people in the world. There are the creatives. The artists, t...

Shelly Rood is Jane Bond. Captain Shelly is a 16-year Army intelligence officer who spent her career doing one thing: reading situations most people couldn’t see, synthesizing what it meant, and briefing decision-makers on what to do about it. She was exceptionally good at it. She was also in the wrong place at the wrong time with the wrong people. Just like Charlie Chaplin’s Little Tramp. Not the...

This is a 🏴‍☠️ Founding Members–Only 🏴‍☠️ post. Founding Members get access to the Pirate Eddie Bot to ask category design questions, weekly actionable insights, the full library with 30+ audiobooks, 250+ mini-books, and more. See the Founders Deck here . Dear Friend, Subscriber, and Category Pirate, Last week, the same day Creator Capitalist launched, Pirate Christopher gave a keynote in San Di...

Lydia Flocchini is a lawyer who decided the law wasn’t enough. Nick Kringas is a restaurateur, SEO pioneer, and serial category designer. Together, they walked into a legal tech conference with a $24,000 budget, a two-week runway, and a question that stopped attorneys cold: Are you AI invisible? They left with a signed client with $90,000 in revenue, 15 warm prospects, and a pipeline trajectory to...

New research is showing what we’ve suspected for a while: on average, AI is making people stupider over time. Not because AI is bad. Because most people use it badly. They show up with radical obvious—” write me a blog post about the 10 smart things to do in marketing for 2026 ”—and get radical obvious back. They skim it, copy-paste it, and move on. Their core premise never gets challenged. Their...

Jeff Klimkowski didn’t plan on his career ending up in the toilet (pun intended.) He was a Deutsche Bank investment banker. The kind of kid who made his sister drive him to school so he could read the Wall Street Journal in the passenger seat. He had the job. The trajectory. The spreadsheet-perfect life plan. Then his childhood friends had too many burritos and a dumb idea. Flushable wipes for men...