The Wall Street Journal covers companies. Pirate Street Journal cover categories.

Each week, we pick three headlines worth paying attention to and break down the category underneath. Live every Tuesday at 7 am PST / 10 am EST. See the news through a different lens.

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Dear Friend, Subscriber, and Category Pirate,

Here’s what we covered in this episode:

1. Zuck published 6,500 words on free AI. Meta is spending $600 billion by 2028 to deliver it.

Monday morning, Mark Zuckerberg published 6,500 words called “The Future is for Everyone”.

Open weights are back. A new model called Muse Glimmer Now. A billion dollar fund for the towns around Meta’s data centers. Model safety criteria handed to the board, because in his words he shouldn’t be the sole decision maker on how superintelligence gets deployed. And a fully private mode for personal agents that even Meta cannot see into.

Sitting underneath all of it: $145 billion of capital spending this year. $600 billion by 2028. A stock investors dumped in July when he couldn’t explain how any of it makes money.

As a category manifesto, it’s a good one. He frames the problem, then paints a new and different future.

He did this exact thing once before. He renamed the company Meta and category designed a market called the metaverse. It cost well over a billion dollars, and it never arrived, because he could never articulate what the customer got out of it.

The vision isn’t the problem. The author is.

The seminal question in AI is not how powerful your model is. It’s whether we trust you.

2. LinkedIn says 41% of its long posts are written by AI. Its detectors flag humans at 60%.

LinkedIn now has a button that says “seems like AI slop.”

Pangram Labs looked at nearly 57,000 items from April to June. 41% of long-form posts and 30% of all public comments were entirely AI-generated. On X, it was 29%. On Reddit, 13%. A second firm, originality.ai, looked at 5,000 public LinkedIn posts in July and found that 81% used AI more than a moderate amount.

LinkedIn disputes the numbers and won’t give its own. It says it removes more than 200,000 AI spam comments a day and catches 94% of generic posts before they spread.

The detectors disagree with each other, and writers who used zero AI have come back scored at 60%.

The future of creating everything is vibe creating. Everybody knows vibe coding. This is the same thing for decks, books, maths, and work generally. And LinkedIn is busy scarlet lettering it.

AI is a tool, yet nobody demanded a warning label for any of the last four tools:

• The spreadsheet. Nobody called it synthetic math.

• PowerPoint. Nobody sat down and said, today we’re watching Jimmy’s synthetic presentation.

• Spell check. Nobody voided your document over it.

• The calculator and the slide rule. Still legal.

There is a real problem in here, and it isn’t the writing.

Deepfakes are real. A fake video of a world leader or a CEO is the front end of a fraud. Guardrails there, absolutely. Scarlet letters on a person who used AI to fix their commas, no.

LinkedIn already shipped the button that solves this. It says unfollow. If it’s slop, we don’t care whether it came from a machine or from a sloppy brain.

3. Wine shipments fell 11% on the ground. United is pouring 9.5 million glasses in the air.

On the ground, people are drinking less, eating less, and losing their attention span. At altitude, every number runs the other way.

Wine. California wineries shipped 203 million cases last year, down 11%, with growers ripping out prized vines they can’t sell. In the air, United is on track to pour 9.5 million glasses in Polaris this year and has put $35 million into its wine program in two years. American went through 3.5 million bottles of Italian sparkling in twelve months. One airline placement moves 4,000 to 6,000 cases a quarter. Getting on a restaurant list moves 1,000.

Weight. Jefferies says if average passenger weight drops 10% on GLP-1s, planes get 2% lighter, fuel burn falls 1.5%, and EPS rises 2.8% at Delta, 3.5% at United, 4.2% at Southwest, and 11.7% at American. Fuel is 19% of operating expense, $39 billion a year.

Wi-Fi. More than 1,100 aircraft have Starlink installed, 7,500 equipped or under contract across 46 airlines, at $200,000 a plane. SpaceX says at least one airline is watching passengers book a connection over a nonstop on purpose, just to be on a Starlink aircraft.

Drones. DoorDash just cleared FAA certification and is building American-made delivery drones, into a sky that already has small planes in it.

The press filed four unrelated oddities.

When we look at it through the category lens, they’re all related and showcase where consumer spending is headed.

3 conversations to have about the news with the Pirate Eddie Bot and Pirate Christopher Bot

Every move above works on your business too. The Pirate Eddie Bot and the Pirate Christopher Bot help you run these plays on YOUR category, they come with the founding tier, and they jam 24/7.

Take this to them this week:

• Audit your give to get. Tell the bots exactly what you take from a customer and exactly what they get back, then ask which side of that ledger a stranger would trust. Zuck’s ledger is 6,500 words on one side and an ad model on the other.

• Separate your problem and POV from your plan and polish. Hand the bots your last three pieces of work and have them mark which layer AI actually touched. Polish is fine. Outsourcing the POV is how you become the 41%.

• Find the superconsumer you’re pricing as a seat class. Ask the bots who inside your best segment would gladly pay for one specific thing you currently give away, and what you should ask for in return.

The through-line: every company in this episode already has something worth trading for. The ones that won this week asked for it out loud instead of taking it quietly.

Not a founding member yet? You can join here.

New episodes drop every Tuesday: three topics, thirty minutes, a couple of bongos.

Our Deep Dive Reports go deep on one company or one shift, with the category read and the call attached. Founding Members get each one start to finish the day it drops, and everyone else gets the preview. Read the Deep Dive Reports here.

Arrrrrrr,

Category Pirates 🏴‍☠️

Eddie Yoon

Christopher Lochhead

P.S. - Every story this week came down to the same move: find the problem before you go shopping for a solution.

The Category Design Academy is where you do that at the category level. You name the problem only you can name, then design the category around it, so you stop competing on terms somebody else set.

The next cohort starts in October and will sell out. Apply now to save your seat.

👉 Learn more about the Category Design Academy here.

Welcome to the Pirate Street Journal. The Wall Street Journal covers companies. We cover categories.

Every Tuesday, we pick three headlines worth paying attention to and break down the category underneath. Every other Friday, we go deeper with a Deep Dive Report, calling where the category goes next. Become a Founding Member to get every Deep Dive Report, mini-book, audiobook, and access to the Pirate Eddie and Christopher bots.

Piratey disclaimer: This is NOT financial advice. None of us have Series 63, Series 6 7, CPAs, CFAs, IUDs, IEDs, and hopefully not IBS. Think of this like professional wrestling. It’s entertainment.Don’t be so smart you’re stupid and suplex your safety net savings.

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Dear Friend, Subscriber, and Category Pirate,

Pirate Eddie made his mom cry.

He was trying to help his parents with their finances, as he had for decades. But he was being so smart, he was stupid. He put being right ahead of their relationship.

Three years ago, Pirate Eddie gave some financial advice to his mom about what to invest in and what not to invest in. She ignored it and put huge chunks of her money into annuities (more about this later).

Pirate Eddie didn’t follow up, and he recently checked in.

He found his mother was bamboozled into annuities that locked up her money for seven years, earning five percent per year. The S&P 500 returned 26% in 2023, 25% in 2024, and 18% in 2025, and 13% year-to-date in 2026. Had she invested their money into the Vanguard S&P 500 index 3 years ago, she would have doubled their money.

Pirate Eddie got overly animated by the math, and he took it too far for his mom.

He hurt her feelings. He dismissed his mom’s need for safety and security. He was fixated on the opportunity cost versus being curious about what his mom and dad dreamed about. And he didn’t see the opportunist, a First Hawaiian Bank ‘financial advisor’, coming.

Annuities are the Keyser Söze of senior citizen financial products.

They are excellent examples of Category Design and languaging. And annuities are some of the biggest legal scams that take advantage of scared senior citizens.

Americans bought $123.9 billion of annuities last quarter, the largest quarter LIMRA has ever recorded, in the fourth straight record year.

With your help and AI we will stop that streak. AI defangs the dense complexity of annuities. Some of you will use this playbook to help your parents. Here’s how to do it differently than Pirate Eddie did.

In this PSJ Deep Dive, we’re going to give a bunch of practical and tactical moves and give you a bunch of scooby snacks.

• Examples of why annuities are dangerous.

• Moves to invest in your parents’ relationship first.

• Diagnostic checks to size the stickiness of the situation.

• Money moves to practically and tactically deal with the dollars.

• 1-page plan that makes this easier to execute today.

If your parents are between 65 and 85 and have savings they are proud of, somebody is likely already advising them, and you may not know that person’s name. The cost of finding out late is measured in years of compounding they cannot get back. The cost of finding out early is one awkward lunch.

The rule of 72 is how to figure out how quickly you will double your money.

Simply take the expected return on your investment and divide it into 72 and voila, you will get the number of years to double your money. At the S&P 500 average return of 10% for decades, they will double their money in ~7 years.

Do this, and you will help double your parents’ net worth within their lifetime and while they are still healthy enough to enjoy it.

Nothing is better for your parents than having more gold in their golden years.

But just beware, these are rocky relational waters ahead.

Danger Will Robinson!

Hey, Ho, Let’s Go!

This Deep Dive doesn’t cover all parent and adult child situations.

Start by working out which of these you are.

There are at least three situations where this DDR won’t apply.

Situation One: If you have very financially savvy and successful parents, this won’t apply to you.

If you know less and have way less financial capital than your parents, stand down. We know of a person who was in their 20s and said to their parents, “Our financial advisor told me to ask you how much money you’re going to leave us.”

Do not do that.

Fire your advisor if your advisor ever tells you to do anything like that. Anyone who builds you a financial plan predicated on your parents’ death is a loser who doesn’t know what they are doing. Have enough EQ to know that this is a question that could permanently taint your relationship with your parents.

Situation Two: If your relationship with your parents is fractured, then talking about money won’t help.

And will likely make it worse.

Relationship Capital must precede Financial Capital. If you are emotionally healthy and strong enough, try to understand why the relationship is fractured and how it makes you feel. Frame, name and claim those feelings. Simply naming your feelings can decrease the power of those feelings and put them into perspective.

It took Pirate Eddie decades to do some of this work with a counselor.

Situation Three: If you have parents who deeply value privacy when it comes to money, tread cautiously.

Money can be deeply personal.

It can be a point of pride or deep shame. It can be a source of identity or idolatry. For some, talking about their money is the equivalent of dancing topless next to Patrick Swayze on Saturday Night Live.

We wish you a deluge of discernment for these types of parents.

If you think time is on your side, then maybe waiting is the wise thing to do. But if there is a trigger event that is not serious, but scary enough to put your parents in a different mental space, then don’t let a good crisis go to waste.

So before you read another word, write down which one you are.

1. Not applicable, because they have this handled.

2. Wait, because the relationship or the privacy issue comes first.

3. Or keep going, because the money is real and the time is right to talk.

If you are in the third group, this is written for you.

Is your parents’ Financial Capital any of your business?

We want the best possible financial outcome for your folks.

But timing is everything.

Your parents’ money becomes much more of your business as you hit 40ish and your folks hit 65ish.

Now, if you are a child of immigrants like Pirate Eddie, you might have been helping your parents with financial capital from a very young age.

Pirate Christopher grew up working class and is the product of a working mother. He started helping his family financially in his 30s. There’s no magic age at which your parents will invite you to talk about their money with open arms and smiles. Most likely, you’re going to get it wrong.

But if you’re going to be wrong, be wrong early versus late.

Too early, and you might get snapped at with a snide comment. Being too late is way worse. The S&P 500 compounds at roughly 10% per year. Which means your money doubles every seven years.

Compounding is your best friend.

We know of someone who is 89 and has a partner who is in his 90s. They both had recent acute health issues. They are now dealing with the fact that where they live now is not going to work. And they need to downsize. They are facing the reality that one or both of them will need healthcare help. No one knows if the math will work when it comes to their money.

This is not good.

Pirate Eddie knows someone with two siblings. They loved each other and their parents. When their parents passed away, they left a vacation home to the three children. All of them have fond memories of that vacation house. All three children had very different points of view on what to do with the house.

Sell it? Keep it? Rent it?

None of the siblings talk to each other anymore.

Giant bummer.

11 Tips to Have This Talk Without Making Your Mom Cry

This is a mix of teaching about the annuities industry, relational wisdom from our battle scars, some ways to gauge how serious this is for you and your parents, and practical moves and templates to make this easier.

Tip 1: Recognize How Annuities Lie with the Truth

Annuities are the big bad guy we want you to look out for.

One of the folks on our Pirate ship used to do marketing for annuities, and this is what he said.

“You would think annuities are sold by gray haired, seasoned professionals with ties at a respectable insurance company. But it’s much closer to Stratton Oakmont like in the Wolf of Wall Street. There were young kids who couldn’t spell the word investment hammering phones. Did we know the outcome and impact on senior citizens? Not a clue. Did we know how it worked, nope. We just sold the annuities that made us the most money.”

An Annuity is one of the greatest examples of Category Design in financial services.

• They know their superconsumer: Scared senior citizens who are less money-savvy.

• They know their problem: The scariness of outliving your savings.

• They know their POV: Guaranteed returns for life.

• They designed the company: Nice sales reps.

But the Category Design was done by mercenaries, not missionaries.

They sell safety and security to seniors who are scared of outliving their savings. They deliver a consistent and guaranteed rate of return. The safety and security come with secret costs, commissions, and other catches that are designed to steal senior citizens’ life savings.

How did they do that?

Trustworthy sales reps that look like your neighbor, church member, or extended family. They give those sales reps some of the most masterful, compelling and deceptive languaging. Here are some of their greatest hits of languaging and lies.

Lie #1: Liquidity feature

• Why it sounds great: I can access my money, woohoo!

• Why this is lying with the truth: You have to pay penalties to withdraw your money. These penalties are buried and complicated.

• Why this is BS: It’s your money. Why shouldn’t you be able to access your money, just like you can in a checking, savings, mutual fund or even a stock?

Lie #2: Downside protection or 0% floor

• Why it sounds great: I can’t lose money ever, whew!

• Why this is lying with the truth: Inflation destroys your money at 2-3% per year. The cost of a nursing home increased 4.4% per year from 2004 to 2024. Annuities give you a rate that barely covers inflation.

• Why this is BS: Healthcare costs are the biggest risk for senior citizens. You must earn a return on your investment.

Lie #3: No upfront fees

• Why it sounds great: Wow, it sounds like I’m not being charged anything?

• Why this is lying with the truth: This is like Bill Clinton saying, “It depends on what your definition of is is.” Many annuities have an 8 percent commission that is paid at the very beginning. They are saying a commission isn’t a fee. And there are plenty of fees, just not upfront.

• Why this is BS: A Vanguard S&P 500 Index fund costs you $0.30 per year for every $1,000 you invest. You can buy a stock with no commission. When you factor in all the hidden charges, the average annuity costs $20 to $40 per year for every $1,000 you invest. That is one hundred times higher than the Vanguard fund. If you pull your money out early, you will pay $100 for every $1,000 you invest.

Use any of these three examples to help you and your parents see what’s really going on.

Tip 2: Don’t dismiss their fear and feelings

Your parents won’t care how much you know until they know how much you care.

Once people get into their 50s, 60s, and 70s, they meet a chorus of people in various financial categories that specialize in separating older folks from their money.

Pirate Eddie’s parents grew up in the aftermath of the Korean War.

They worked hard for decades, not earning much but saving prodigiously by delaying gratification. Of course, his mom felt deeply worried about losing what they had worked so hard to save. Security and not losing money were her number one goals.

This is true for many older people.

Don’t dismiss the emotions that come with a clock that is ticking down faster for them than it is for you. Pirate Eddie wishes he had listened to and held his mom’s feelings without judgment. On the back nine, it is only natural for people to want as much certainty and security as possible.

Tip 3: Start aspirational, not financial

After Pirate Eddie course-corrected and listened to his parents’ feelings, he started to ask what their goals and dreams were.

His mom said she didn’t want to have to depend on Pirate Eddie and his wife financially. She wanted to live comfortably for the rest of her life. She wanted to leave something behind to their grandchildren.

Once he had their goals, Pirate Eddie was in a much better place to Category Design a plan they would be excited about. Talking about money is much easier after talking about motivations.

Money is a tool to fund outcomes.

So a money conversation, without the context of what the money is for, is a backward conversation.

Tip 4: Affirm five times for every one correction

The rest of this Deep Dive is for Founding Members.

Founding Members get the full mini-book library, The Pirate Eddie Bot and the Pirate Christopher Bot, the audiobook library, and every deep dive we publish.

Already on Monthly? You still have the mini-books. Our most recent mini-book, Charitable Investing, is here.

Upgrade to Founding

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Arrrrr! 🏴‍☠️ Welcome to a 🔒 founders-only edition 🔒 of Category Pirates. Each week, we share radically different ideas to help you design new and different categories. Founding subscribers can access the entire archive of 200+ mini-books and audiobooks. If you’re not a paid subscriber, hop aboard!

Subscribe now

Read more

Arrrrr! 🏴‍☠️ Welcome to a 🔒 founders-only edition 🔒 of Category Pirates. Each week, we share radically different ideas to help you design new and different categories. Founding subscribers can access the entire archive of 200+ mini-books and audiobooks. If you’re not a paid subscriber, hop aboard!

Subscribe now

Read more

Arrrrr! 🏴‍☠️ Welcome to a 🔒 founders-only edition 🔒 of Category Pirates. Each week, we share radically different ideas to help you design new and different categories. Founding subscribers can access the entire archive of 200+ mini-books and audiobooks. If you’re not a paid subscriber, hop aboard!

Subscribe now

Read more

The Wall Street Journal covers companies. Pirate Street Journal cover categories.

Each week, we pick three headlines worth paying attention to and break down the category underneath. Live every Tuesday at 7 am PST / 10 am EST. See the news through a different lens.

Subscribe now

Dear Friend, Subscriber, and Category Pirate,

Here’s what we covered in this episode:

1. Why did the best turnaround in casual dining come from betting on basic tech?

Chili’s parent company is up more than 500% since June of 2022.

Twenty quarters in a row of sales growth. Last quarter sales rose another 4%, on top of a 31% jump the year before.

Almost none of it came from AI.

Here is what their tech boss, Chris Caldwell, bought instead:

• Wi-Fi. Two years of work to fix it in 1,200 restaurants.

• 23,000 iPads. The old tablets couldn’t hold a charge through one shift.

• 9,000 kitchen touch screens and 1,200 laptops for managers.

• Six AI projects. His team pitched him a few dozen. He kept six, and says he expects to cut more than he approves.

The robot waiters went back.

Chili’s did the thing almost nobody does.

They started with the problem, not the tech.

A restaurant has two problems.

1. The small one: the staff can’t hear each other. Anyone who has watched The Bear knows how fast that goes wrong.

2. The big one is turns and tickets. How many times a day does that table get used, and how much does each guest spend.

A robot waiter doesn’t move either number.

A button on the table that calls your server does. Paying up front, like at a ramen shop in Tokyo, does. Plastic food in the window so people know what to order does.

So what does this mean for you?

The Census Bureau says only 17 to 20% of American businesses used AI between December and May. At companies with 250+ people, it’s 37%. At companies under 20 people, it’s under 20%. That number didn’t move for five months.

If you own a small business, you’ve been told that gap means you’re behind.

It means the opposite.

Big companies have the money. You have the thing they lost: you still know what problem your business exists to solve. The S&P 500 minus the seven giant tech companies spends about twice as much buying back its own stock as it does on new ideas. A buyback is a company saying, out loud, that it ran out of things to try.

Use AI as your co-founder. Point it at your real problem in the next 12 to 18 months and you can pass companies a thousand times your size.

2. What happens when the customer becomes the power company?

Base Power is three years old and just raised $1 billion. Investors say it’s worth $13 billion.

It has put more than 23,000 batteries in people’s yards across Texas and Chicago. About 100 more every day.

That adds up to 550 megawatt hours, as much storage as a big power plant project. It’s just spread across thousands of backyards instead of sitting in one place.

Your power company has always been a monopoly. One choice, take it or leave it, run by the government or by a company the government controls.

Base flips it. They own the battery in your yard. They sell you electricity. Then, when everyone’s air conditioning kicks on, and power gets expensive, they sell the power in all those batteries back to the grid.

Here’s why that matters to you. You stop being the person who gets a bill. You become the person with something to sell.

In West Texas, El Paso Electric is now paying homeowners $250 a battery, testing whether it can stop building expensive new plants entirely.

People are already moving. Home electricity costs are up 42% across the country in five years. Up 94% in Washington DC. Up 74% in Maryland. Americans put in a record 1.3 gigawatt hours of home batteries in the first three months of this year alone.

Two things follow, and they annoy opposite ends of the political spectrum.

This is the greenest thing a homeowner can do, because the hours when everyone needs power are exactly the hours utilities burn their dirtiest fuel.

It’s also the Jevons paradox: when something gets cheaper, people use much more of it. Go ahead and run the hot tub.

Underneath all of it is one question. Is power scarce, or is it abundant?

Believe it’s scarce and you ration it, fight your neighbors, and protest data centers.

Believe it’s abundant and you notice there’s a giant nuclear reactor in the sky that has never once sent anybody a bill.

3. How did college kids gets get big career outcomes before graduating?

Twenty college students at Indiana University run a real investment fund called Sample Gates Management.

Not a class project. This was real money from real strangers.

• $12 million raised from outside investors. None of it from the school.

• $7.8 million from 74 investors last year. One person wrote a check for $700,000.

• 400 deals looked at a year, 12 bought. Ten experienced executives sit on their committee and turn down about a third of what the students bring.

• 65% profit in about 16 months on the first one they sold, a warehouse outside Indianapolis.

Not one of them gets paid.

Now the other number. The New York Fed says 41.5% of recent college graduates are working jobs that never required a degree.

There are two kinds of education, and only one of them is the real one.

The first is class. Read it, memorize it, hand it back on a test.

The second is apprenticeship. I do it while you watch, and we talk about it. Then you do it while I watch, and we talk about it. Then you can do it alone.

• For a surgeon, that’s residency.

• For a trader, that’s the desk.

• For these students, it’s a real deal with real money that can really lose.

So here’s the question to ask, whether it’s for you or for a kid whose tuition you’re paying: how fast do you get to actually do the work?

A future surgeon can wait ten years, because there’s a big paycheck at the end. If you can’t see when you’d ever get to do the real thing, that’s your problem right there.

But the real winner of this WSJ article is the author. Look at who wrote the article. Lily Bell Polling is a senior at Yale and a reporting intern. A young person learning to report, writing about young people learning to invest.

3 conversations to have about the news with the Pirate Eddie Bot and Pirate Christopher Bot

Every move above works on your business too. The Pirate Eddie Bot and the Pirate Christopher Bot help you run these plays on YOUR category, they come with the founding tier, and they jam 24/7.

Take this to them this week:

• Find your small problem and your big problem. Give the bots your five biggest headaches and have them sort out which ones are plumbing and which one is the real problem underneath. Chili’s plumbing was Wi-Fi. Its real problem was turns and tickets. What are yours?

• Find where your customer has no choice. Ask the bots which part of your industry works like a monopoly, then design the version where your customer gets to sell something back. That’s what Base Power did to the grid.

• Time your apprenticeship. Have the bots map how long it takes a new person at your company to actually do the work. If the answer is years, you have a design problem.

The through-line: everybody reported the technology, and the problem was sitting underneath it the whole time. The robot, the utility, the diploma. Each one was a solution looking for a problem, and the winners this week went the other way.

Not a founding member yet? You can join here.

What’s coming up on Pirate Street Journal

Next Tuesday, three topics we are already arguing about:

• Zuck’s accidental AI manifesto. He wrote a long post about privacy and open source. The behavior he’s describing is what Apple and Google already do, which makes it an argument for owning those two and not Meta.

• LinkedIn wants you to use less AI. 41% of long posts and 30% of comments there get flagged as fully AI-written. Pirate Eddie got flagged at 40% on something he wrote himself, about renting fins in Hawaii. This is the rare one where the three of us don’t agree.

• Three weird facts about the future of flying. Wine is losing drinkers on the ground and winning at 35,000 feet. Consultants are booking layovers on purpose to get planes with Starlink. And DoorDash is putting delivery drones into a sky that already has small planes in it.

New episodes drop every Tuesday: three topics, thirty minutes, a couple of bongos.

Our Deep Dive Reports go deep on one company or one shift, with the category read and the call attached. Founding Members get each one start to finish the day it drops, and everyone else gets the preview. Read the Deep Dive Reports here.

Most of what we make never shows up in a post like this one.

$20 a month gets you the Tuesday episodes, every mini-book, every DDR preview, and every Breaking News report in full.

$375 a year, about a dollar a day, gets you all of that plus the vault. Every Deep Dive Report start to finish the day it drops. The Pirate Eddie Bot and the Pirate Christopher Bot, which will jam with you at 3am about your category. All 300+ mini-books we have ever written, 30+ audiobooks, and all seven big books.

Come aboard here.

Arrrrrrr,

Category Pirates 🏴‍☠️

Eddie Yoon

Christopher Lochhead

P.S. - Every story this week came down to the same move: find the problem before you go shopping for a solution.

The Category Design Academy is where you do that at the category level. You name the problem only you can name, then design the category around it, so you stop competing on terms somebody else set.

The next cohort starts in October and will sell out. Apply now to save your seat.

👉 Learn more about the Category Design Academy here.

Arrrrr! 🏴‍☠️ Welcome to a 🔒 subscriber-only edition 🔒 of Category Pirates. Each week, we share radically different ideas to help you design new and different categories. For more: Audiobooks | Category design podcast | Books | Sign up for a Founding subscription to ask the Pirate Eddie and Christopher Bot your category design questions.

Subscribe now

Dear Friend, Subscriber, and Category Pirate,

This mini-book is for three types of people.

1. If there’s an American baby in your life, there is a $1,000 bill right in front to pick up.

2. If you want to get started in generosity, keep reading for ten simple ways to start.

3. If generosity is already who you are, read this to make your giving compound.

This is a shorter mini-book, pirate.

To make it faster for you to get to the Buried Treasure.

🔊 Want to listen to this mini-book instead? Head to the audiobook.

Listen to the audiobook

The Case for Generosity

Generosity feels great.

Right?

Some of you are nodding your head, as this is a core belief of your identity and what you practice regularly. You’ve seen your generosity have a positive impact and bless many people. And you want to keep giving.

But some of you are shaking your head as you feel the pressure to provide for yourself and your family with limited resources. You’d love to give more, but it makes sense to deal with debt and build up your safe and smart investments first.

And sadly. Some of you still bear scars of generosity gone bad. Maybe a well-intentioned gift backfired. Maybe a gift came with strings attached. Or maybe over the last few years you discovered that some international NGOs (Doctors Without Borders, we’re talking to you) you’ve supported for years is more ‘suss’ than previously thought (as the kids say).

Generosity is legendary, in the right context, for the right people at the right time.

What if we told you it wasn’t about generous or selfish people?

• What if current charity doesn’t work because of a fundamental category flaw?

• What if charity avoided waste, unintended consequences, and corruption?

• What if Category Design could fix it?

Imagine a world where generosity felt less risky and exponentially more good. Where everyone experiences the blessing of giving and receiving.

We call it Charitable Investing. It is exponentially more exciting, enduring, efficient, and radically different than Charitable Giving.

Hey Ho, Let’s Go.

What You Get When You Give

Giving feels good.

Everybody knows that. What most people do not know is how much of it science has actually measured. The reward is real and it shows up in the brain, your mood and even your bloodstream.

Your Brain Likes Giving

Put someone in an fMRI scanner and move their money to a food bank, and the brain’s reward circuitry lights up.

Not the part of the brain that handles duty. Not the part that handles obligation. The reward system.

The same circuitry that responds to food and to money coming in. And when the person chooses to give rather than being made to, the response gets stronger.

Your brain experiences giving as a gain.

Researchers have run this experiment many times over. Hand people money. Tell one group to spend it on themselves. Tell the other to spend it on someone else. Ask everyone at the end of the day how they feel.

The people who spent it on someone else came out happier.

The effect is modest, but it keeps holding up. Spending on other people does more for you than spending on yourself. Think about how much of the economy is built on the opposite assumption.

Your Blood Pressure Likes Giving

In 2016, researchers took seventy-three older adults who had been diagnosed with high blood pressure. They randomly assigned them to spend money on other people or on themselves.

The group giving to others finished with lower systolic and diastolic blood pressure than the group spending on themselves.

The researchers put the size of that effect in the same range as blood pressure medication or exercise.

Your Body Likes Giving

The University of Michigan went into the Wisconsin Longitudinal Study found that regular volunteers had a significantly lower mortality rate than non-volunteers.

However, this longevity boost occurred only for those who volunteered out of genuine compassion for others. Those volunteering for self-serving reasons saw no survival advantage. Ultimately, the body’s protective, stress-buffering biological response is triggered by true empathy.

What Must Be True to Feel the Benefit of Giving

The research is clear that the reward arrives under three conditions.

Choose it. Voluntary giving produces a stronger response than obligated giving. Write the check because you want to, not because someone put you on a list. (This is why you feel angry paying taxes and feel great helping your niece buy her first car.)

Connect to it. The reward is bigger when there is a human being on the other end of it. Give to people, not to abstractions.

See it land. In one study, participants who gave to a cause that showed them exactly what their money bought got happier the more they gave. Participants who gave to a large, general fund got no measurable lift at all.

If you cannot see what your money did, your brain cannot pay you for it.

We were taught that giving is something you do for other people, and that the personal cost is what makes it noble.

The evidence says otherwise.

Giving is one of the highest return uses of a dollar you will ever find. It moves your mood. It moves your blood pressure. It moves your years.

The generous were never sacrificing.

They were compounding.

The Fundamental Flaws of Charitable Giving

Americans gave approximately $617 billion in 2025 to US charities.

This is more than the GDP of most countries. In high-tax nations across Europe and Asia, the government is the sole provider of social welfare, and citizens outsource their compassion to the state.

The US did something different. By combining an aggressive tax-deductible framework with deep-seated traditions of giving, we created a brand new category: Incentivized Private Philanthropy.

Sadly, both systems to move money to those who need it are deeply flawed.

The government’s bucket leaks like crazy.

The Justice Department’s 2025 National Health Care Fraud Takedown charged 324 defendants with $14.6 billion in intended losses, the largest such action in its history. The 2026 takedown charged 455 more.

CMS estimates $3.5 billion in hospice and home care fraud in Los Angeles County. In Minnesota, claims to a Medicaid autism program grew from $600,000 in 2018 to more than $400 million by 2025.

They are programs we fund specifically to care for the elderly, the sick, and the disabled.

Private philanthropy sucks money in, but doesn’t dole out much.

Donor advised funds held $326 billion in assets in 2024 and took in nearly $90 billion more that year.

The donor claims the tax deduction the moment the money goes in. There is no legal requirement that it ever comes out. Average payout runs around 24% a year, which sounds fine until you notice that a meaningful share of accounts distribute nothing at all while the sponsor collects fees on the balance.

Private foundations at least have a rule.

They must pay out 5% of assets annually. The Institute for Policy Studies found that among the 144 US private foundations with endowments over $1 billion, the median payout rate was 5.1%. Private foundations are hoarding charity so they can grow.

Then there are the middlemen.

The Tampa Bay Times and the Center for Investigative Reporting spent a year auditing professional fundraisers and found the worst charities in America were paying solicitors more than 90 cents of every dollar raised. Kids Wish Network collected roughly $128 million over a decade and sent about $110 million of it to fundraisers. Around 2.5% reached a child.

This is why 18.3% of Americans say they have high trust in the charitable sector.

Read that twice. We gave a record $617 billion to a system we openly do not believe in.

None of these were bad donors. Every one of them was bad Category Design.

Kind of makes you feel like this.

The Church is a Paradox of Giving

The church is both the worst and best example of charity and giving.

The Catholic church sits on the world’s most idle real estate and also built the world’s most enduring way of helping and healing billions. It’s the same church with the same balance sheet, but two radically different outcomes.

Did you know the Catholic Church owns more land than the size of Texas?

The Catholic Church owns about 277,000 square miles of land. The estimated value of the land is $350 billion dollars.

Much of the $350 billion dollars of real estate is largely used one day out of a week.

We’re not saying this is all a waste. We are saying let’s confront the structural design flaws that create waste. And apply Category Design to re-invent a new form of charity that is more powerful and productive.

Does it seem like fantasy land that the Catholic church could do this? Nope. We just need to go back to the future.

The Catholic church helped create the category of modern hospital as we know it.

In about 370 AD, the Catholic church created St. Basil the Great’s hospital complex near Caesarea. It was so vast that contemporaries called it a “new city.” It had isolation units for lepers, housing for the poor and elderly, and systematic care on a scale never seen before.

St. Benedict said, “the care of the sick is to be placed above and before every other duty, as if indeed Christ were being directly served by waiting on them.”

Today the Catholic Church manages 5,377 hospitals, 13,895 outpatient clinics/dispensaries, and a total of 103,951 health, charity, and assistance institutions worldwide (including homes for the elderly and disabled, orphanages, and nurseries).

It is estimated that the Catholic church represents 26% of the world’s healthcare facilities. In the US, one in seven patients are seen in a Catholic hospital.

If hospitals were purely a charity, they would not have enough money to endure. If hospitals were purely a business, the mission of saving lives would miss the mark. Hospitals aren’t perfect, but imagine a world without any hospitals or modern healthcare.

Charity plus capitalism is what has helped the category called Hospitals endure for centuries.

A New Law Changed the Category of Giving

In July 2025, Congress passed the One Big Beautiful Bill Act. Buried inside it were two changes that almost nobody has connected.

The first change made donating money worth less.

Starting in 2026, if you itemize your taxes, the first half-percent of your income no longer counts as a deduction. Make $400,000 and your first $2,000 of donations gets you nothing back. Separately, the highest earners now get capped at a 35% benefit instead of 37%, so a $10,000 gift that used to save $3,700 in taxes now saves $3,500.

Small numbers. Clear direction. Washington just made the old category slightly less rewarding.

The second change created something that didn’t exist before: a tax-advantaged investment account for every American child, that anyone can contribute to.

One law. It made Charitable Giving a little worse and made Charitable Investing possible. We don’t think anyone planned it that way. We think it’s the most useful accident in the history of American philanthropy.

Charitable Investing is Legendary

There are two obvious ways to help people who need it.

Give them a fish. Or teach them to fish.

The first way doesn’t last past the first fish. The second way still requires giving time and requires mastery to keep getting fish.

The third non-obvious way is to give someone stock in a fishing company, that compounds over time and grows. While you sleep. So you can buy the fish you want for yourself and others, possibly into perpetuity.

That is Charitable Investing.

A genuinely new category that came to life on July 4th 2026.

530A accounts. Originally conceived as Invest America accounts by Brad Gerstner of Altimeter Capital.

Every American child born between 2025 and 2028 receives a $1,000 government seed contribution invested in a broad market index fund. Families can add up to $5,000 a year. The money is structured like an IRA for a minor, so the child takes control at 18 under retirement account rules.

And for the first time in American history any person can make a direct tax advantaged gift into a capital account for any American child.

Direct. Person to person. Into an ownership account that compounds for 18 years.

Pirate Christopher and his wife are shifting 50% of their giving to direct charitable investing.

The Five Conditions Where Charitable Investing Works.

Charitable Investing looks most promising where these five conditions are present.

Read more

The Wall Street Journal covers companies. Pirate Street Journal cover categories.

Each week, we pick three headlines worth paying attention to and break down the category underneath. Live every Tuesday at 7 am PST / 10 am EST. See the news through a different lens.

Subscribe now

Dear Friend, Subscriber, and Category Pirate,

Here’s what we covered in this episode:

1. Is Google’s negative $6 billion free cash flow is good news?

Revenue of $119.8 billion, up 24%. Cloud up 82% with a $514 billion backlog, up from $460 billion in a single quarter. Free cash flow of negative $6 billion, the first negative quarter in company history. The Journal ran one great chart of the cliff and called it worrying.

Same filing shows $242 billion in cash and marketable securities. Trailing twelve month revenue of $446 billion. Trailing operating cash flow of $186 billion.

One chart cannot explain a company mid-transformation, and a quarter is the wrong unit of measurement when the thing you are measuring is a category migration.

Milking versus prosecuting.

Two kinds of companies exist. The ones milking a category king position they already own, and the ones prosecuting a future opportunity while the window is open. Buybacks are the tell for the first group. A buyback is a company admitting it has run out of ideas and would rather grow the stock than the business.

Cloud added $11 billion of incremental revenue. Search added $8.3 billion. The most perfect business ever built on the internet is now the slower half of its own company, in dollars, and that is the achievement.

• Amazon. Incorporated 1994, no full year of profit until 2003, stock up roughly 300,000% since IPO.

• NVIDIA. Still founder led, still prosecuting.

• Microsoft. A CEO who acts like a founder, and the innovator’s dilemma refuted.

• IBM. Read its most recent quarter for the alternative.

The Mag Seven are guiding to somewhere between $700 and $750 billion of CapEx this year because AI shows the greatest category potential ever exhibited. The press covered the cliff and missed the migration.

2. Does the man who built a $10 billion law firm need 5,000 people, or just 20?

Kirkland & Ellis became the first law firm in history to cross $10 billion in annual revenue. David Fox, 68, wrote that playbook. He just co-founded Irving, an AI-native firm running in stealth with fewer than 10 lawyers and engineers, already advising on real deals. Kirkland has set aside $500 million for its own AI platform.

Reject the premise.

Kirkland is going to light that money on fire, because the money is being spent to make thousands of people incrementally more productive inside a structure built for people.

When the movie camera arrived, the first thing anyone did with it was point it at a stage play. Movies only happened when someone built entertainment purpose-made for the camera. Most law firms, and most of the S&P 500, are still videotaping the play.

Fox is doing the other experiment. Firm with AI at the core, people bolted on. His own question: does he need 5,000 talented people, or 20.

All the value sits with the senior partner who has the context and the battle scars, plus the AI-native 20-year-old. The middle layer of associates and managers of managers has value in the old system only, and the old system needs to feed the middle to keep the machine running.

Knowledge worker to creator capitalist. Applying existing knowledge is the job AI takes. Creating net new things with AI is the job that survives. Make AI the co-founder of your career.

And the billable hour is over. McKinsey is already 25% outcome-based. Nobody cares how long it took.

3. What if doing the right thing paid 12x?

Optus Bank, founded 1921, and M&F Bank, founded 1907, just announced a merger creating the largest African American owned financial institution in the country. Ten locations, $1.27 billion in combined assets, a deal worth more than $105 million. Five years ago, right before we wrote about it in Harvard Business Review, M&F traded under $4 a share. It closed near $48.

That is a 12x return in a bank most of Wall Street has never heard of, and the merger happened by choice rather than distress.

Charitable investing over charitable giving. Giving is a transfer. Investing aligns the incentives, which means it compounds and it repeats. Justice deposits started as corporate treasury cash parked in minority depository institutions. The next level was buying the equity.

• Netflix. 2% of global cash holdings, over $100 million.

• PayPal. $500 million.

• Block, JPMorgan, Bank of America, Wells Fargo, State Street, Moody’s. Deposits and stock.

• Costco, Dick’s Sporting Goods, Aflac. In as well.

None of them wired that money out of sympathy. They wired it because these are legendary banks run by great operators. CEO James Sills grew the balance sheet, cut non-interest expense, originated SBA loan revenue, and bought back shares.

There is a category design question underneath. A Black-owned bank is a specialization built on a highly identifiable superconsumer, and niching down on your super works when you commit to it completely. The free market, not a mandate, is what fixed this one.

We’re publishing a mini-book on Charitable Investing this Friday.

3 conversations to have about the news with the Pirate Eddie Bot and Pirate Christopher Bot

The bots come with the founding tier and jam 24/7. Their job is to take this week’s moves and run them against your category, not ours.

• Find out whether you are milking or prosecuting. Hand the bots your last three budget decisions and ask which future opportunity each one is prosecuting. If the honest answer is that you are defending a position you already hold, you are Alphabet’s critics, not Alphabet.

• Ask what you are videotaping. Describe your core delivery model and ask the bots which parts exist only because humans used to do them. Fox found his answer and it was 5,000 people versus 20.

• Convert one giving line into an investing line. Bring the bots a cause you already fund and ask them to design the version where the incentives align and the money comes back. M&F went from under $4 to $48 while doing exactly that.

The through-line: in all three stories, the people who look reckless are the ones building for the category that is arriving, and the people who look prudent are optimizing a category that is leaving.

Not a founding member yet? You can join here.

Recorded Friday, July 31. Every number above is as of that morning.

Piratey disclaimer: This is NOT financial advice. None of us have a Series 63, Series 7, Series 6, CPAs, CFAs, IUDs, IEDs, and hopefully not IBS (this makes DUDE Wipes sad).

Stay tuned for next week’s episode.

Arrrrrrr,

Category Pirates 🏴‍☠️

Eddie Yoon

Christopher Lochhead

Welcome to the Pirate Street Journal. The Wall Street Journal covers companies. We cover categories.

Every Tuesday, we pick three headlines worth paying attention to and break down the category underneath. Every other Friday, we go deeper with a Deep Dive Report, calling where the category goes next. Become a Founding Member to get every Deep Dive Report, mini-book, audiobook, and access to the Pirate Eddie and Christopher bots.

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Dear Friend, Subscriber, and Category Pirate,

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.

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!

Pirates love weird data.

Thomas Laffount of Coatue shared some cool stuff at the recent All-In-Podcast Liquidity event.

A unicorn worth a billion-dollar valuation has an 8% chance of becoming a decacorn at ten billion.

A decacorn has a 13% chance of becoming a centicorn at one hundred billion.

A centicorn has a 31% chance of becoming worth a trillion-dollar valuation.

VC David Sacks had the most valuable observation. And question. Does it suggest that the odds go even higher for a one trillion dollar company to become a ten trillion dollar company?

The data suggests Sacks’ hunch was right.

This insight contradicts the law of large numbers. The largest companies are expected to grow more slowly. The law of large numbers says your growth rate comes down as you get bigger. They even called it a “law”.

Now, there’s a new POV.

The Big Are Getting Bigger

The Mag 7-10 are too big to keep compounding, right?

Nvidia cannot run from five trillion to ten trillion, can it? Can Apple be any bigger? The math runs out, doesn’t it?

They can.

Let’s look at more weird data.

Read more

The Wall Street Journal covers companies. Pirate Street Journal cover categories.

Each week, we pick three headlines worth paying attention to and break down the category underneath. Live every Tuesday at 7 am PST / 10 am EST. See the news through a different lens.

Subscribe now

Dear Friend, Subscriber, and Category Pirate,

Here’s what we covered in this episode:

1. Can a power plant on a truck beat China?

Five years ago, China had under four gigawatts of energy storage. Today it has around 155 and is targeting 300 by 2030. The entire United States has 57. Chinese suppliers control 90% of the global market for storage battery cells.

Centralized top-down versus decentralized bottoms-up.

China wins centralized. No NIMBYism, hundred-year plans, local mayors competing to execute. America wins by letting ten thousand flowers bloom.

Where government fails, the category can’t wait.

Musk worked out that the government had become a critical part of his supply chain, so he did what Apple did and bought it. July filings showed he took APR Energy for roughly $1 billion: trailer-mounted turbines topping a gigawatt, deployable in days.

• Microsoft. Firing up Three Mile Island through Constellation.

• Meta. Launched its own free community college to train the trades it cannot hire.

• Tesla. Megapacks for cities running brownouts, Powerwalls for homeowners arbitraging cheap electrons against peak pricing.

The missing piece has a name: the megapod. Batteries plus GPUs, a data center in a box, sized between the grid-scale Megapack and the household Powerwall. Any enterprise with unused land becomes a distributed data center. Alaska pays every resident about $1,000 a year for sitting on oil. The megapod is that annuity for a farm, a church, a factory.

The Journal reported the scoreboard and missed the rule change. Power is a peak usage problem, which makes it a pricing problem you can solve from your garage.

2. Can weird data pay your rent?

Ben Affleck sold a stealth AI startup called InterPositive to Netflix for $587 million in cash. A downtown Los Angeles ice cream shop called 28 Wishes bets $20 a day on cold weather forecasts and covers 43% of its rent. Seven-person companies are doing the work of fifty, with 15% fewer managers and 15% lower costs.

There’s weird data and weakness data.

Every business sits on data nobody else has, and most of it documents where the business is weak. Ice cream sales fall about 20% every time it drops below 70 degrees. The prediction market turns that weakness into a hedge that pays the landlord.

Turn cost into revenue. This is the Amazon move. Shipping cost became Prime. Compute cost became AWS.

• InterPositive. Trains a small model on a single film’s own footage, lighting, and style. An artist equipped with AI, not an AI engineer walking into film. Netflix created binge watching and can now load the buffet faster.

• Lemonade. Everybody hates filing a claim, so it built its point of view on the thing the insurance category is worst at.

• Universities. Administrators drove tuition through the roof. Cut that layer 15% and college costs 15% less.

Read wealth inequality as taking from the rich and you get one set of solutions. Ask how to make everybody wealthy and you get Invest America.

3. Are consultants’ outcome based fees a sign that fixed salaries will no longer be the norm?

McKinsey has tied 25% of global fees to outcomes.

Bain says 30% of its business is now AI and tech-enabled, on the way to 50%. BCG expects AI work to jump from a fifth of revenue to 40% next year at a $12 billion firm. Meanwhile, the $300 to $500 consultant hour is cracking, and 150 alumni of those firms are under contract training AI to do the entry-level work.

Waiters and waitresses are wondering what took them so long?

The question is will time-based compensation (hourly, salary) without outcomes last much longer for everyone else?

Missionaries who drive outcomes are about to get paid more.

Free riders lose the hiding places.

3 conversations to have about the news with The Pirate Eddie Bot and The Pirate Christopher Bot

The bots run this week’s moves against your category, not somebody else’s. They come with the Founding tier, and they jam at 2 am.

• Find your missing middle. Tesla had grid scale and household scale and nothing in between, which is where the megapod lives. Ask the bots what sits between your biggest offer and your smallest, and who is stranded in that gap.

• Audit your weird data and your weakness data. Hand the bots the parts of your business you would rather not talk about. An ice cream shop turned “it gets cold sometimes” into 43% of its rent.

• Reprice from time to outcome. Give the bots your invoice and ask what outcome the client actually bought. If McKinsey can put a quarter of its fees at risk, you can put something at risk too.

One through-line connects all three. The incumbent optimizes the game as written. The pioneer changes what gets counted: power that moves instead of power that stays plugged in, data nobody thought was an asset, and the outcome instead of the hour.

Two ways to climb aboard now:

Monthly: $20/month. You’ve done dumber things with $20. You get the Tuesday episodes, every mini-book, every DDR preview, and every Breaking News report in full.

Subscribe now

Founding: $375/year. About a dollar a day for every future DDR start to finish the day it drops, plus:

• The Pirate Eddie Bot and The Pirate Christopher Bot, your 24/7 AI jamming partners

• All seven of our full-size books

• Every mini-book we have ever written (300+)

• Our entire audiobook library (30+)

Want the whole thing every time? Become a Founding Member.

Recorded Friday, July 24th. Every number above is as of that morning.

Piratey disclaimer: This is NOT financial advice. None of us have a Series 63, Series 7, Series 6, CPAs, CFAs, IUDs, IEDs, and hopefully not IBS (this makes DUDE Wipes sad).

Stay tuned for next week’s episode.

Arrrrrrr,

Category Pirates 🏴‍☠️

Eddie Yoon

Christopher Lochhead

Arrrrr! 🏴‍☠️ Welcome to a 🔒 subscriber-only edition 🔒 of Category Pirates. Each week, we share radically different ideas to help you design new and different categories. For more: Audiobooks | Category design podcast | Books | Sign up for a Founding subscription to ask the Pirate Eddie and Christopher Bot your category design questions.

Subscribe now

Dear Friend, Subscriber, and Category Pirate,

Someone owes Pirate Christopher a lot of money.

In his last Silicon Valley CMO role, at Mercury Interactive, he helped frame, name, and claim a new category: Business Technology Optimization.

BTO.

HP bought Mercury for roughly $4.5 billion. Then HP reorganized its entire software division around BTO. After the deal closed, the head of HP Enterprise told her executives that BTO was half the reason they bought the company.

Half.

Of $4.5 billion.

Pirate Christopher’s response: “Someone owes me a lot of money.”

You know what the marketing dashboard said about BTO?

Nothing.

There was no impression count for “we changed what the acquirer believes this company is.” There was no MQL field for “the board now sees a bigger future.” No attribution model on Earth could see the most valuable thing a CMO ever does.

Drive enduring market cap growth.

The gap between the value a great marketer creates and the credit the company can count, is the oldest injustice in the profession.

Pirate Christopher became a publicly traded tech company CMO at 28. No playbook. He figured it out, by reading, seeking out mentors and doing. He taught himself to drive the kind of outcomes that show up in enterprise value, and got asked to do the job two more times.

This is the mini-book he wishes someone had handed him back then.

Being a first-time CMO is, was, and always will be hard.

But today there is an enormous difference. Today’s CMOs get to do the job with an AI co-founder. And a squadron of agents. An unfair advantage no marketer in history has ever had.

Before you say it, we know the argument. “If everyone has access to the same AIs, it’s not a material advantage.”

Please hear this with love: you have no idea what you’re talking about.

First, most people and most companies are way behind on AI. Second, even if they catch up, who cares. Every F1 driver has a legendary car. Some win a lot more than others. It’s not just the car. The driver matters.

Capisci?

The only question is whether you use agents to become indispensable, or to generate prettier versions of the reports that get CMOs fired.

In this mini-book, we’ll jam on:

• Why CMOs get deleted from the C-suite.

• The currency switch that makes the company build around you.

• Why AI agents make category design mandatory to fight the Obvious Onslaught.

• Three legendary CMOs who drove massive market cap upside, not marketing metrics.

• The seven levers of the Demand P&L, including why every CMO needs a bot, and how to war-game products, pricing, categories, and Lightning Strikes with AI clones of your Superconsumers before you spend a dollar.

This is the best moment in history to be a CMO.

🔊 Want to listen to this mini-book instead? Head to the audiobook.

Listen to the audiobook

Grab your pirate flask.

Hey Ho, Let’s Go!

CMOs Count the Wrong Currency

Roughly a third of the Fortune 500 has no CMO at all.

Read that again.

What should be the most strategic driver of growth, with the most exciting metrics, the most AI-forward, and therefore the most powerful function in business is the one a third of America’s biggest companies decided they can live without.

It gets worse.

In 21% of larger tech companies, the head of marketing reports to the Chief Product Officer. CEOs disrespect marketing’s ability to drive the business so much, they actually believe marketing belongs inside the product team.

This is as dumb as making Sales report to Finance. But it happens.

CFOs aren’t optional. Chief Commercial/Revenue Officers aren’t optional. CHROs aren’t optional. CTOs aren’t optional.

CMOs are.

And even when CMOs get invited to the party, they don’t survive it. CMO tenure at S&P 500 companies now stands at 4.1 years, against 7.6 for the CEO. Most will be handed the budget, and the blame, and be gone before any of it compounds.

Why?

Because marketing is measured in a currency the boardroom does not spend.

Impressions. Reach. Awareness. Engagement. All real. And all like trying to spend Canadian dollars at an American cash register. Your CFO, CEO, board, and investors can’t put legacy marketing currency in the bank. You can’t pay a dividend with reach. You can’t buy back shares with engagement. You can’t reinvest awareness into R&D.

And it’s not enough to run your metrics through a currency exchange at the end of the quarter. You get hit with a massive discount and walk away with a lot less than you thought you earned.

Most marketers speak marketing bullsh*t.

Not the currency of business.

Marketing must generate investable dollars, not impressions. Marketing returns must flow frictionlessly back into the P&L, not the slide deck. Marketing must drive enterprise value.

Let’s be clear about what we’re NOT saying.

We are not talking about becoming a stock-hyping, pump-and-dump, shady shyster. We’re talking about building enduring enterprise value by delivering material outcomes, while educating investors, customers, and employees on the category potential of your market over time.

The CMO measured in KPIs is trivial.

The CMO measured in market cap is transformational.

The moment you switch currency, AI stops being a productivity tool and becomes the most valuable co-founder you’ve ever had.

Why Agents Change the Currency, Not Just the Speed

Francesco Federico, the global CMO of S&P Global, wrote an entire book called The Agentic CMO.

Legendary title!

He argues an agent is a colleague the CMO leads, not a tool the CMO uses. That marketing leadership is now the practice of organizing intelligence, human and machine, toward a single point of view.

Pirate Francesco’s right.

Wharton’s Ethan Mollick argues that management itself is the new superpower. Specifying goals, outputs, and evaluation criteria. Delegating to agents the way a legendary executive delegates to people.

Also right.

The AI search crowd says you have to show up when the machines do the answering.

Right again.

Every one of them is teaching you how to organize intelligence.

None of them can tell you where the point of view comes from.

So put on the category lens. Once you see this, you can’t unsee it.

Fact one: agents make execution close to free.

Customer interaction, content, media buying, campaign ops, lead scoring, personalization, on-going optimization, reporting. The entire execution layer of marketing is being agentified right now.

Tasks that require headcount are being handed to agents that work in parallel, around the clock, at near-zero marginal cost.

Fact two: left alone, AI will spawn the Obvious Onslaught.

LLMs are probability machines. They predict the most likely next words for the broadest possible audience. Which means the default output of the entire technology is the obvious answer.

“Drop the price.”

“Make the logo bigger.”

“Copy what’s trending.”

The AI Obvious Onslaught is like carbon dioxide. You can’t really see it or smell it. By the time you notice it, you’re nearly dead. When every CMO has a fleet of agents at the same generic inputs, every company converges on the same marketing.

Flawless. Instant. Identical.

The sea of sameness, industrialized.

Fact three: Different will become more rare than rare earth minerals.

Different by definition is non-obvious.

Different is low probability, which is why AI will never choose it.

Different is the moat. Write that down. On a post-it-note. Put that note on your laptop. Different is the moat. Do it now. We’ll wait ;-)

Deciding what’s different. Naming it. Framing the category around it. That was always the real job of marketing. Agents didn’t change the job.

They exposed it.

Think about every classic marketing excuse. The economy. The competition. The campaign. The agency. Creative took too long. We didn’t have enough budget (our favorite.)

Every one execution excuse.

But execution will become an abundant commodity. Not executing will be like saying, I don’t have enough air to breathe or water to drink.

Results ≠ No Results + An Excuse.

Results = Results.

What’s left, when the excuses are gone, is the quality of your decisions about what to build and why it’s different.

Fact four: your next buyer is an agent too.

Gartner projects that machine customers will influence $30 trillion in purchases by 2030.

AI agents researching, comparing, negotiating, and buying on behalf of humans and companies. Agents don’t feel brand affinity. Agents don’t get moved by your Super Bowl spot. Agents answer with the default.

And the default is the category king.

Category Science says the king earns 76% of the category’s economics. That was the human-buyer number. When machines do the buying, it’s likely even more than 76% goes to the Category King.

She who frames the problem becomes the solution.

Literally at the model layer.

Your digital footprint gets embedded (or not) in the LLMs. If your category, brand, and product are not legendary in the digital world. You run the risk of being AI invisible. Because the AIs train on your digital reputation, digital POV content and category leadership.

Which is why AI can’t be a feature of your marketing plan.

AI must be your co-founder.

Not a tool under the table. A note-taker. Or co-pilot. AI is a co-founder who coaches you, cheers you on, and confronts you. It pressure-tests your POV at midnight. It reads ten thousand customer reviews while you pour a coffee. It never gets political, never protects turf, and never confuses activity with outcomes.

AI should not be an adjective on your LinkedIn profile.

AI should be a proper noun on your org chart, right next to the CMO.

The Measuring Stick That Matters

“The cure is sometimes worse than the disease.”

That’s V.F. Ridgway, writing in 1956, in a paper called Dysfunctional Consequences of Performance Measurements. Fifty years later, Simon Caulkin summarized Ridgway’s warning in one line: what gets measured gets managed, even when it’s pointless to measure and manage it.

Pirate Christopher lived this.

Early in his CMO life he was at Vantive, a CRM company locked in an epic 18-month category battle with Siebel for all the marbles. Siebel focused on leading the category. Vantive’s first-time CEO responded by turning inward. He mandated a draconian Kaizen measurement system. Document everything. Measure everything. Meetings multiplied. The Monday exec staff meeting moved to 3 p.m. and reliably devolved into beatings that ran until 9.

During one of those sessions, Pirate Christopher turned to the Head of Product and asked, “What do you think we can do to beat Siebel?”

The answer:

Read more

Arrrrr! 🏴‍☠️ Welcome to a 🔒 founders-only edition 🔒 of Category Pirates. Each week, we share radically different ideas to help you design new and different categories. Founding subscribers can access the entire archive of 200+ mini-books and audiobooks. If you’re not a paid subscriber, hop aboard!

Subscribe now

Read more

The Wall Street Journal covers companies. Pirate Street Journal cover categories.

Each week, we pick three headlines worth paying attention to and break down the category underneath. Live every Tuesday at 7 am PST / 10 am EST. See the news through a different lens.

Subscribe now

Dear Friend, Subscriber, and Category Pirate,

Here’s what we covered in this episode:

1. Is New York being so smart they’re stupid?

On July 14th, New York became the first state in America to ban new hyperscale data centers. Governor Kathy Hochul signed a permit freeze of up to a full year, with calls to extend it. The stated reasons: power bills, water, grid strain.

Category kings bring more blessings than burdens, and New York only did half the math.

In 1978, four people started a memory company in the basement of a Boise dental office. That’s Micron. Today it’s the third-largest private employer in Idaho, and its newest expansion is $15 billion, the largest private investment in state history and the first new memory fab built in America in 20 years.

The choice governors keep missing is future versus past.

Shenzhen was a fishing village in the late ‘70s and is now 17 million people, proof there can be more than one Silicon Valley. The next Boise is wherever someone decides to welcome it.

2. Are Apple’s higher prices good long-term?

On June 25th, Apple raised prices across the line: the Mac Studio with M3 Ultra jumped $1,300, the M4 Max $500, even the entry MacBook $100. Tim Cook called the memory shortage a “100-year flood.” DRAM and NAND ran up about 60% last quarter, another 13 to 18% coming, and analysts say memory could double before it’s done.

Business Media reads a supply-chain story.

The category underneath is where your AI lives and who gets to watch.

On-prem is back, and the high-order bit is data ownership, not the sticker price.

For 30 years, the arrow pointed one way, into the cloud, ever since Benioff incorporated Salesforce in 1999. It’s swinging back, because when your data goes into someone else’s servers, they see what you’re doing and build the context layer on top of it. Ask Cursor, which grew into one of the fastest software companies ever on top of Claude, right until Anthropic saw the growth and shipped a competitor.

Play that out for the enterprise and the individual:

• Goldman Sachs writing an S1 does not want an AI harvesting its intellectual capital.

• Merck, P&G, Citibank. Every regulated giant lands on the same paradigm: I own my data, I own the context layer, you can’t compete with me.

• Dell. Infrastructure growing 40%, consumer laptops 5%. On-prem drives both, and hardware prices with it.

Apple is a missionary on privacy the way Netflix was on binge-watching when Pirate Eddie got flamed for cheering its 2011 price hike. More memory on the phone means more AI on the device, plus the agency to route the right model to the right task instead of being beholden to one LLM.

3. Can Costco cashiers become millionaires?

The Wall Street Journal profiled a Costco cashier: $32.90 an hour, 60 years old, 40 years in, started at Price Club making $5.85. He owns a three-bedroom house with a pool and a 401k north of a million dollars. He’s not the exception. Costco’s own CFO says many thousands of hourly workers have crossed a million in retirement, and turnover runs 7% a year against a retail average of 60%.

That math only works one way.

The category makes the career, so find the category king before it’s crowned and ride the left side of the S curve. Costco marks everything up 15% when the rest of retail runs 35 to 40%, and that radical generosity is the tell. The pattern is everywhere once you stop looking at prestige:

• US Robotics. The CEO’s secretary and janitor both hit millionaire on stock before the 3Com acquisition.

• Chobani. Gave 10% of the company to its 2,000 early employees.

• WinCo, Stewart’s Shops, waste management. Nobody’s dream résumé, stacked with millionaire employees anyway.

Then look at the other side. Xerox did almost $22 billion in revenue in 2011 and is on track for about $7 billion this year. You can be smarter and sharper than you were then and still be worse off, because Xerox operates in declining categories. The category made you a loser while you got better.

3 conversations to have about the news with the Pirate Eddie Bot and Pirate Christopher Bot

The Pirate Eddie Bot and the Pirate Christopher Bot are your 24/7 jamming partners on the Founding tier. They take the week’s moves and help you apply them to YOUR category. Three to run this week:

• Count your blessings, not just your burdens. Hand the bots your industry, your city, or your company and ask what “yes to the category king” would pull along the way New York refused and Boise didn’t. Pressure-test whether you’re planning for the next 40 years or the last four.

• Own your data and own the context layer. Ask the bots where in your business you’re handing your intellectual capital to someone who can turn around and compete with you, and what your on-prem version looks like. Cursor learned this the expensive way.

• Find the category king before it’s crowned. Feed the bots your career or your next hire and score it on the S curve: is the category rising, does it treat its supers and investors well, is AI the co-founder? That’s the difference between a Costco and a Xerox.

The through-line across all three: the category makes the company, which makes the career, and the news keeps rewarding the people who reject the premise the press prints.

Not a founding member yet? You can join here.

What’s coming up on Pirate Street Journal

Tuesday episodes: three topics, thirty minutes, a couple of bongos. Mini-books and DDRs land every other Friday. Founding Members get the full DDR start to finish; everyone else gets the preview. Breaking News reports go to all paying subscribers.

Two ways to climb aboard now:

Monthly: $20/month. You’ve done dumber things with $20. You get the Tuesday episodes, Friday mini-books, and every Breaking News report in full.

Founding: $375/year. About a dollar a day for every future DDR start to finish the day it drops, plus:

• The Pirate Eddie Bot and the Pirate Christopher Bot, your 24/7 AI jamming partners

• Every mini-book we have ever written (300+)

• Our entire audiobook library (30+)

• All seven of our full-size books

Want the whole thing every time? Become a Founding Member.

Recorded Friday, July 17th. Every number above is as of that morning.

Piratey disclaimer: This is NOT financial advice. None of us have a Series 63, Series 7, Series 6, CPAs, CFAs, IUDs, IEDs, and hopefully not IBS (this makes DUDE Wipes sad).

Stay tuned for next week’s episode.

Arrrrrrr,

Category Pirates

Eddie Yoon

Christopher Lochhead

Welcome to the Pirate Street Journal. The Wall Street Journal covers companies. We cover categories. We don’t just read the news. We call where the category is going next. Every Tuesday, we pick three headlines worth paying attention to and break down the category underneath. Every other Friday, we go deeper with a Deep Dive Report, calling where the category goes next. Become a Founding Member to get every Deep Dive Report, mini-book, audiobook, and access to the Pirate Eddie and Christopher bots.

Subscribe now

Dear Friend, Subscriber, and Category Pirate,

Everyone is debating whether the World Cup adds $17 billion to US GDP.

Before we go deep, here are a few changes to look for:

The first two volumes of the Pirate Street Journal Deep Dive Reports (DDRs) have been very timely, despite the fact this is not financial advice.

• In volume 1 on May 22, 2026, we said AI hardware was about to re-rate. Micron just posted the best quarter in its history. Micron is poised to make more money in 2026 than its entire 35 year history combined. Since then, the stock went up as high as +67% and is now +13% as of July 16, 2026).

• In volume 2 on June 10, 2026, we said more than one thing can be true about the SpaceX IPO. That SpaceX would be well positioned for the long run, and that the IPO would be volatile near term. The stock IPO'd at $135, traded above $200, and has since round-tripped all the way back, dipping below its $135 IPO price for the first time this week (as of July 16, 2026).

• In volume 2 on June 10, 2026, we said power was the one square on the AI board almost nobody owned. In July 2026, regulatory filings revealed Elon quietly acquired APR Energy for roughly $1 billion, a fleet of trailer-mounted gas turbines topping a gigawatt of capacity, deployable in days, and pointed it straight at his AI data centers.

Both were spot on, and their value was in the timeliness of the post. They are meant to be helpful not just that day, but in the near term over the next few months, quarters, or even 1-2 years.

So we’re making two changes.

First, we’re separating our Pirate Street Journal podcast episodes from our DDRs. The reports have gotten long enough to earn their own lane. Going forward, Pirate Street Journal episodes drop on Tuesdays, and the mini-books and DDRs come out every other Friday.

Second, we’re changing who gets what. Going forward, there are two kinds of reports:

• Deep Dive Reports (DDRs) are the long, twice-a-month Friday reports. Founding Members get the full report. Everyone else gets a preview in their inbox and can read the rest by upgrading.

• Breaking News reports go out when there is breaking news on a category transformation. Every paying subscriber gets these in full, Monthly and Founding alike.

Starting with the next DDR, the complete version is a Founding Member benefit.

Want the whole thing every time? Become a Founding Member, and you’ll get every future DDR start to finish the day it drops, plus:

• The Pirate Eddie Bot and the Christopher Bot

• Our entire audiobook library

• All seven of our full-size books

Subscribe now

Let’s dive in!

TL;DR (for the pirates who won’t read 4,000 words, and we know who you are)

Everyone is debating whether the World Cup adds $17 billion to US GDP.

Wrong number. The real story: America’s national brand (valued by Brand Finance at $37.3 trillion) fell 7% in a year, roughly $2.6 trillion in estimated brand value, with American friendliness ranked 156th out of 193 nations.

Read more

The Wall Street Journal covers companies. Pirate Street Journal cover categories.

Each week, we pick three headlines worth paying attention to and break down the category underneath. Live every Tuesday at 7 am PST / 10 am EST. See the news through a different lens.

Subscribe now

Dear Friend, Subscriber, and Category Pirate,

Here’s what we covered in this episode:

1. Micron and Gwen Shotwell didn’t give money away. They ended charity as a category.

Invest America accounts are live. Every kid born between 2025 and 2028 gets one, seeded with $1,000 in an S&P 500 index fund.

Then the checks started clearing.

• Gwen Shotwell, president of SpaceX. Gifting SpaceX stock into more than 2 million accounts for kids in less affluent areas, a sixth of a stake worth roughly $2 billion.

• Micron. $250 million, the biggest corporate commitment of its kind, seeding up to a million kids and matching its own employees a thousand dollars a child.

The press filed it under philanthropy. Wrong category.

Charitable giving is broken at the root. It treats the dollar as an expense, not an asset. The charity sells the stock, spends it down, GNA skims the middle, and you hand out fish instead of teaching anyone to catch one.

Charitable investing is a different category.

Nobody spends the dollar. It compounds for 18 years, and every incentive aligns: when Micron’s CEO donates $250 million of Micron stock, every child in America now wants Micron stock to go up.

And it is peer-to-peer. No NGO takes a VIG on the way through.

The Wall Street Journal covered a tax-friendly headline. It missed that a hundred-year-old category just started shrinking, and the one replacing it turns a million kids into millionaires by their early thirties.

2. Everyone is counting the World Cup’s $17 billion. The number that matters is $2.6 trillion.

FIFA projects $17 billion in US GDP and 185,000 jobs across 11 host cities. Economists fire back that it is less than one-tenth of one percent of the economy, a rounding error.

Both sides are counting the same tickets, hotels, and hot dogs over 30 days.

Brand Finance values brand America at $37.3 trillion, the most valuable nation brand on earth. Last year it fell 7 percent, about $2.6 trillion gone, the steepest drop of any of the 193 nations they track.

America is a new category of country, and the repair job is running on peer-to-peer citizen journalism. Europeans and Asians are here filming Buc-ee’s, Waffle House, and free refills, then telling the folks back home the warnings were a lie.

What’s ordinary to you is extraordinary to others.

Countries that get this play it on purpose. Korea exports kimchi, K-pop, and K-dramas, not just its technology. FIFA runs brand collaborations down to a co-branded deodorant. The Olympics are next, and America’s move is to keep raising its hand to host.

3. Black Rifle Coffee sells coffee. Its best ad of the year didn’t have any in it.

Founded in 2014 by a Green Beret, Evan Hafer, Black Rifle does around $390 million a year and went public at a $1.7 billion valuation. It got there by pulling money out of paid ads and pouring it into its own content and a quarter-million coffee club subscribers.

For America’s 250th it towed the largest American flag ever, wrapped it in sasquatch, guns, and freedom, and released a 16-minute behind-the-scenes film.

No beans, mug, or product shot.

Black Rifle’s category design is a super, not a product.

Its customer is a self-described patriot, and the super of one is the super of nine.

This is marketing the problem, not the product. Market the product and you say “I want your money.” Make something for your super and they hear “they want to help me.”

That is what missionaries do, and it travels on word of mouth. Half a dozen people texted us that video the day it dropped.

Dude Wipes does it. Sarah Blakely does it with Spanx. Old Navy has done it with a Fourth of July tee for twenty years.

3 conversations to have about the news with the Pirate Eddie Bot and Pirate Christopher Bot

Every move above is portable to you. The Pirate Eddie Bot and the Pirate Christopher Bot help you run these plays on YOUR category, they come with the founding tier, and they jam 24/7.

Take this to them this week:

• Turn your giving into investing. Ask the bots where your business hands out fish when it could teach people to fish. Micron turned a $250 million donation into a million aligned shareholders instead of a spent-down grant. Where is your dollar going to die, and where could it compound?

• Count the brand, not the receipts. Have the bots find the $2.6 trillion number hiding behind your $17 billion one, the asset you are building or bleeding while everyone argues about the 30-day cash. The World Cup is buying back a nation brand nobody put on the P&L.

• Make something for your super, not your product. Work with the bots to design your version of the coffee ad with no coffee, a gift to your super consumer that never mentions what you sell. Black Rifle skipped the bean and claimed the country.

The through-line: everyone reported the transaction, and the category was underneath. The NGO, the ad network, the anger industrial complex. Each middleman got bypassed, and the value went straight to the people who care.

Not a founding member yet? You can join here.

What’s coming up on Pirate Street Journal

New episodes drop every Tuesday: three topics, thirty minutes, a couple of bongos. Mini-books and DDRs land every other Friday. Founding Members get the full DDR start to finish, everyone else gets the preview. Breaking News reports go to all paying subscribers, monthly and founding, in full.

The first two Deep Dive Reports have already earned their keep:

• Volume 1 (May 22, 2026): we said AI hardware was about to re-rate. Micron is up 61% and just posted the best quarter in its history.

• Volume 2 (June 10, 2026): we said more than one thing can be true about the SpaceX IPO, strong for the long run and volatile near term. It IPO’d at $135, ran to $202, and sat at $153 as of June 25, 2026.

Two ways to climb aboard now:

Monthly: $20/month. You’ve done dumber things with $20. You get the Tuesday episodes, every mini-book, every DDR preview, and every Breaking News report in full.

Founding: $375/year. About a dollar a day for every future DDR start to finish the day it drops, plus:

• The Pirate Eddie Bot and the Pirate Christopher Bot, your 24/7 AI jamming partners

• Every mini-book we have ever written (300+)

• Our entire audiobook library (30+)

• All seven of our full-size books

Want the whole thing every time? Become a Founding Member.

Recorded Wednesday, July 8th. Every number above is as of that morning.

Piratey disclaimer: This is NOT financial advice. None of us have a Series 63, Series 7, Series 6, CPAs, CFAs, IUDs, IEDs, and hopefully not IBS (this makes DUDE Wipes sad).

Stay tuned for next week’s episode.

Arrrrrrr,

Category Pirates

Eddie Yoon

Christopher Lochhead

The Wall Street Journal covers companies. Pirate Street Journal cover categories.

Each week, we pick three headlines worth paying attention to and break down the category underneath. Live every Tuesday at 7 am PST / 10 am EST. See the news through a different lens.

Subscribe now

Dear Friend, Subscriber, and Category Pirate,

Tesla dropped a 216-page report this week, and we could not wait for Tuesday to break it down. Paid subscribers get the Breaking News today. It will unlock for free subscribers in a week. Don’t wait a week to listen:

Subscribe now

Here’s what we covered in this episode:

1. Privacy is Crucial For Any AI Category King

Tesla published three privacy promises in its 2025 impact report: give customers choices, stay transparent, and safeguard the data. The thing making those promises has eight exterior cameras, an interior camera, microphones, GPS, and a cellular link that has been phoning home on every car built since 2012.

This is trust plus experience as a category multiplier.

Apple spent a decade turning privacy into a moat, and it was never the feature. It was the belief that when something goes wrong, Apple takes care of you. Tesla is running the same move, except its product does not sit in a drawer. It watches the road, the cabin, and your location every mile.

Trust is the Achilles heel for OpenAI and Anthropic.

Why can Tesla even make the promise? Follow the incentive. Show us the incentive, and we will show you the outcome.

As Pirate says, “If you don’t pay for the product, you are the product.”

It’s hard to trust a company when you are the product.

That’s like asking a chicken to trust Tyson.

2. Category Kings Must Create New Metrics

Tesla reports its fleet helped customers avoid 37 million metric tons of CO2 in 2025.

Does this help their P&L?

Not immediately. But they are designing the rules of engagement in a way legacy car markers can’t compete with.

New categories require new metrics.

The category king does not inherit the old scoreboard, it invents one. “Avoided emissions” is a metric Tesla essentially created, for a scoreboard Tesla built, and then crowned itself on. Own the scoreboard and the score takes care of itself.

3. Category Kings 10x Human Flourishing

We’re stealing another idea, which is the true purpose of a company is to help humans flourish.

Tesla’s airbag can deploy up to 70 milliseconds before impact.

Why is that important?

A normal airbag fires about 50 milliseconds after you hit something. At highway speed 70 milliseconds is roughly six feet, the difference between the bag being full when your head arrives and still unfolding when it does.

• 6.2 million crashes a year in the US, 36,000 of them fatal.

• 30% involve speeding, call it 11,000 fatal.

• A 0.12-second head start cuts force by about 25%, or 2,700 fewer deaths.

But this isn’t just about saving lives.

Tesla is playing chess by building trust from their missionary stance to save lives.

Because the end game for Tesla is Robotaxi and Full Self Driving software.

And they key problem is humans don’t yet trust the robot to drive.

Every safety proof point Tesla ships closes that perception gap, and the day self-driving is provably safer than human driving, the category tips.

3 conversations to have about the news with the Pirate Eddie Bot and Pirate Christopher Bot

Every move above is portable. The Pirate Eddie Bot and the Pirate Christopher Bot help you run these plays on YOUR category, they come with the founding tier, and they jam 24/7.

• Audit your give-to-get. Hand the bots your business model and ask where your customer is paying with data instead of dollars. Tesla can promise privacy because it makes margin on the car, not on your information. Where is your incentive pointed?

• Invent the metric before you claim the crown. Ask the bots what “avoided emissions” is for your category, the number only you can report and everyone else has to react to. Old metrics do not work in new categories.

• Find the reframe blocking your growth. Ask the bots to name the trust gap standing between your product and mass adoption. For driverless it is “I don’t trust the robot.” What is yours, and what proof point closes it?

The through-line: everyone waited for Tesla to win on the product, and Tesla won on the company and the category. The magic triangle is product, company, and category, and the two most people forget are the two doing the work.

Not a founding member yet? You can join here.

What’s coming up on Pirate Street Journal

New episodes drop every Tuesday: three topics, thirty minutes, a couple of bongos. Mini-books and DDRs land every other Friday. Founding Members get the full DDR start to finish, everyone else gets the preview. Breaking News reports go to all paying subscribers, monthly and founding, in full.

Two ways to climb aboard now:

Monthly: $20/month. You’ve done dumber things with $20. You get the Tuesday episodes, every DDR preview, every mini-book, and every Breaking News report in full.

Founding: $375/year. About a dollar a day for every future DDR start to finish the day it drops, plus:

• The Pirate Eddie Bot and the Pirate Christopher Bot, your 24/7 AI jamming partners

• Every mini-book we have ever written (300+)

• Our entire audiobook library (30+)

• All seven of our full-size books

Want the whole thing every time? Become a Founding Member.

Recorded Wednesday, July 8th. 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).

We’ll be back on Tuesday at 7 am PST / 10 am EST.

Arrrrrrr,

Category Pirates

Eddie Yoon

Christopher Lochhead

Arrrrr! 🏴‍☠️ Welcome to a 🔒 founders-only edition 🔒 of Category Pirates. Each week, we share radically different ideas to help you design new and different categories. Founding subscribers can access the entire archive of 200+ mini-books and audiobooks. If you’re not a paid subscriber, hop aboard!

Subscribe now

Read more

Arrrrr! 🏴‍☠️ Welcome to a 🔒 subscriber-only edition 🔒 of Category Pirates. Each week, we share radically different ideas to help you design new and different categories. For more: Audiobooks | Category design podcast | Books | Sign up for a Founding subscription to ask the Pirate Eddie Bot your category design questions.

Subscribe now

Dear Friend, Subscriber, and Category Pirate,

This is Part 2 of the America: A Different Category of Country. If you missed Part 1, you can read it here.

Hey Ho, Let’s Go!

🔊 Want to listen to this mini-book instead? Head to the audiobook.

Listen to the Audiobook

Money

11. Stock ownership goes universal

Read more

The Wall Street Journal covers companies. Pirate Street Journal cover categories.

Each week, we pick three headlines worth paying attention to and break down the category underneath. Live every Tuesday at 7 am PST / 10 am EST. See the news through a different lens.

Subscribe now

Dear Friend, Subscriber, and Category Pirate,

Here’s what we covered in this episode:

1. Microsoft is entering a human centric business to scale AI

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 a lower-margin businesses in tech, on purpose.

The stock is down about 20% this year and has shed over a trillion from its peak.

Companies are not stuck on the technology. They are stuck on the vision and execution. They are stuck on the fear of change. They are stuck on the fear of not delivering ROI and impact.

The promise of enterprise AI is great, but no one knows what to do with it.

Enter the senior consulting partner.

The vast majority of the value of consulting firms resides in the senior partner. They spend the least amount of time on solving the clients’ problem, because they already know what the answer is. They have the war stories, scars and wins to prove it.

Senior partners with niche expertise know how to deliver ROI. They are precisely the people Microsoft needs to make AI immediately valuable. Here are a few examples of niche-use cases.

• Bankruptcy and turnaround. Ninety days to pull a business out of the fire.

• M&A due diligence. Buy this, sell that, fast. Perfect for AI.

• Cost takeout. The least strategic move and the most certain one.

If Microsoft were smart, they’d follow a precise playbook we layout to make that $2.5 billion deliver $250 billion of AI margins.

Hint. It starts with incentives and how the smartest senior partners get paid, and how they wish they could be paid.

2. SpaceX’s non-obvious acceleration M&A play.

There are two types of M&A.

The first type is consolidation M&A, where you roll up companies from the past, strip their G&A for synergies and make the past more profitable. The goal here is to buy companies on the cheap.

The second type is acceleration M&A, where you buy the future and fan their flames even higher. Crazy multiples and valuations are normal here.

So what is SpaceX doing?

It’s going after the mobile’s market worth hundreds of billions of dollars.

Last month, the Philippines became the first country to connect phones straight to the SpaceX satellites. Dense cities need cell towers, but a country of remote islands like the Philippines is where Starlink isn’t just one of the options, it’s the only one.

Wall Street’s plan for him: buy T-Mobile.

Elon wants the spectrum, not the company, the way Google bought Motorola for the patents.

But what if we told you that while the global mobile market is $200 to $400 billion-a-year category, that it wasn’t the end game?

What if we told you an even bigger category is Elon’s real play?

Hint: Go back to the future with Elon and you’ll figure it out.

3. Europe has AC agita.

175,000 Europeans die from heat every year, per the World Health Organization.

Paris hit 104 last week, the fourth such day since the 1800s.

The fix is a century old: AC.

Japan 91%, South Korea 86%, China 60%, Mexico 16%, India 5%. On this one technology, the UK is closer to India than to the developed world. Japan and South Korea were destitute 60 years ago. AC didn’t just make them comfortable, it made them productive.

The fight went ideological. The same script is now running in America over AI data centers, the buildout that could double GDP, argued about like a threat instead of a cure.

Every transformational technology hits the same emotional wall before it wins:

• Air conditioning. A century-old machine still fought in European courts.

• Full self-driving. The freedom to hand an aging parent back their independence.

• GLP-1s. Proof we were never destined to be an obese country.

The way out is word of mouth, the most powerful form of marketing there is.

Roger Martin calls it being reflective, not reflexive.

Make it personal. Your parents. Your grandparents. The friend six months pregnant heading into a European summer with a fan.

The Wall Street Journal covered the death toll and missed that the cure shipped a hundred years ago.

The fight was never about the machine.

3 conversations to have about the news with the Pirate Eddie Bot and Pirate Christopher Bot

We just told you what’s happening to three categories. The bots help you figure out what it means for yours. Reading the news is the easy part. Turning it into something actionable is the hard part, and that is exactly what The Pirate Eddie Bot and Pirate Christopher Bot are built for. They jam with you 24/7, they come with the founding tier, and they never get tired of your follow-up questions.

Take this to them this week:

• Own the business agenda, not the technology. Tell the bots what tech you’re betting on and have them find the business agenda underneath it, the vision your customer is actually stuck on. Microsoft hired 6,000 humans to sell that, not the software.

• Turn your product into a bundle. Tell the bots your one product and have them spec the category kings around it you could fold into a single thing customers can’t unbundle. Elon wants the pipe so he can own everything that runs on it.

• Stop selling the spec sheet. Tell the bots a technology your market keeps rejecting and have them reframe it from an ideological fight into a personal, emotional yes. Europe is losing 175,000 people a year to a spec-sheet argument.

Three headlines, one move. Somebody has to hold the customer’s hand through the transformation. That’s the whole game.

Not a founding member yet? You can join here.

What’s coming up on Pirate Street Journal

We’re making a few changes to Pirate Street Journal next month.

Every Tuesday, we drop a Pirate Street Journal episode at 7 a.m. PST / 10 A.M. EST. Three topics, thirty minutes, a couple of bongos.

The first two Deep Dive Reports (DDRs) have already earned their keep:

• Volume 1 (May 22, 2026): we said AI hardware was about to re-rate. Micron is up 61% and just posted the best quarter in its history.

• Volume 2 (June 10, 2026): we said more than one thing can be true about the SpaceX IPO, strong for the long run and volatile near term. It IPO’d at $135, ran to $202, and sits at $153 as of June 25, 2026.

The reports are built to pay off not just the day they drop, but over the next few quarters, even the next year or two. So we are making two changes.

One, the reports get their own lane. Episodes drop Tuesdays. Mini-books and DDRs come out every other Friday.

Two, who gets what changes. There are now two kinds of reports:

• Deep Dive Reports (DDRs). The long, twice-a-month Friday reports. Founding Members get the full report. Everyone else gets a preview in their inbox and can read the rest by upgrading.

• Breaking News reports. When there is breaking news on a category transformation, every paying subscriber gets the full report, Monthly and Founding alike.

Starting with the next DDR, the complete version is a Founding Member benefit.

Two ways to climb aboard now:

Monthly: $20/month. You’ve done dumber things with $20. You get the Tuesday episodes, every DDR preview, and every Breaking News report in full.

Founding: $375/year. About a dollar a day for every future DDR start to finish the day it drops, plus:

• The Pirate Eddie Bot and the Pirate Christopher Bot, your 24/7 AI jamming partners

• Every mini-book we have ever written (300+)

• Our entire audiobook library (30+)

• All seven of our full-size books

Want the whole thing every time? Become a Founding Member.

Recorded Friday, June 26th. Every number above is as of that morning.

Piratey disclaimer: This is NOT financial advice. None of us have a Series 63, Series 7, Series 6, CPAs, CFAs, IUDs, IEDs, and hopefully not IBS (this makes DUDE Wipes sad).

Stay tuned for next week’s episode.

Arrrrrrr,

Category Pirates

Eddie Yoon

Christopher Lochhead

Arrrrr! 🏴‍☠️ Welcome to a 🔒 subscriber-only edition 🔒 of Category Pirates. Each week, we share radically different ideas to help you design new and different categories. For more: Audiobooks | Category design podcast | Books | Sign up for a Founding subscription to ask the Pirate Eddie Bot your category design questions.

Subscribe now

Dear Friend, Subscriber, and Category Pirate,

Pirate Christopher’s Scottish grandfather served in His Majesty’s Royal Navy in World War II.

When the war ended, he married his grandmother, packed everything they had, and moved to Montreal with a two-year-old daughter and a job at a rubber factory.

He didn’t move for comfort. He moved out of desperation and possibility.

Often, two sides of the same coin.

A generation later, Pirate Christopher did the same thing. Left Canada at 28 for Silicon Valley. Ten years after failing out of school at 18 with no options, no credentials, no money, and no obvious path forward. He carved out a niche and built a small company. Sold it. To go somewhere that would empower him instead of holding him down.

There was only one place on earth where a kid with nothing could build something legendary.

Pirate Eddie’s family made the same bet from a different direction. His father was pursuing a career as a prosecutor in Korea. But his father remembered how hungry he was as a teenager during the Korean War. He left Korea behind to immigrate to Hawaii. He left his career behind to work as a janitor and limo driver to remove the limits on the education of and upside for his kids.

Two families. Two wars. Two bets on the same country.

And neither of us would be Pirates today without it.

🔊 Want to listen to this mini-book instead? Head to the audiobook.

Listen to the Audiobook

The USA is Still the #1 Place to Move to

Since 2007, Gallup has asked people in 150+ countries a simple question.

If you could move anywhere on Earth, where would you go?

Every single year, the same country wins.

It’s.

Not.

Even.

Close.

About 18% of all the world’s population, more than 170 million people, pick the United States. The runner-up, Canada, draws about half that.

In contrast, China has four times America’s population, yet draws and naturalizes almost no one. Foreign-born folks in China is 0.1% versus 15% in the US. China actually had a net loss of 3.5 million people. Any migration is happening within China, with 376 million people moving from village to city.

America’s demand is not due to its superiority.

People want to move to America because America is different.

Every other country on Earth is a club. America is a catapult.

The wealthiest person in Japan is Masayoshi Son, CEO and founder of Softbank. He was born in Japan. He speaks Japanese. He married a Japanese woman. He is a Japanese citizen with full voting rights.

He is ethnically Korean. He was bullied for being Korean, to the point of contemplating suicide. When entering the Japanese software business as a young entrepreneur, Son faced obstacles, including being denied credit specifically because he was Korean.

In nearly every country. You’re born a member, or you spend a lifetime on the outside.

America is different.

America is purpose-built for giving people driven by dreams an opportunity to go further than they could have at home. America was founded by pioneers.

Not growing up in the US makes it crystal clear to many of those who come here what is possible in America.

They can play bigger in the USA.

It’s hard to see the legendary opportunity that is America if that is all you’ve ever known. Maybe it feels like there’s a lot of fighting in America right now.

But the fight inside this country was never really left versus right.

The fight is between those trying to preserve the past and those trying to create the future. Between the makers and the takers. This has been true throughout the history of America.

The Declaration of Independence was for a future with more freedom.

“Whenever any Form of Government becomes destructive of these ends, it is the Right of the People to alter or to abolish it, and to institute a new Government…”

The Gettysburg Address was for a future with more freedom.

“from these honored dead we take increased devotion to that cause for which they gave the last full measure of devotion — that this nation, under God, shall have a new birth of freedom...”

JFK’s Moon Race was for a future with more freedom.

“We choose to go to the Moon in this decade and do the other things, not because they are easy, but because they are hard…”

MLK’s I Have a Dream was for a future with more freedom.

“I have a dream that my four little children will one day live in a nation where they will not be judged by the color of their skin but by the content of their character.”

Reagan’s Dawn of a New America was for a future with more freedom.

“While other countries cling to the stale past, here in America we breathe life into dreams. We create the future, and the world follows us into tomorrow.”

Jobs’ Stanford commencement speech was for a future with more freedom.

“Stay hungry, stay foolish. You can’t connect the dots looking forward; you can only connect them looking backwards.”

Obama’s Yes We Can speech was for a future with more freedom.

“Change will not come if we wait for some other person, or if we wait for some other time. We are the ones we’ve been waiting for. We are the change that we seek.”

Musk’s mission for SpaceX was for a future with more freedom.

“America would never have been colonized if ships weren’t reusable. We must make life multiplanetary… to extend the light of consciousness beyond Earth.”

Andreessen’s It’s Time to Build was for a future with more freedom.

“There is only one way to honor their legacy and to create the future we want for our own children and grandchildren, and that’s to build.”

And the future’s so bright, you gotta wear shades.

The Three Great Differences

Three questions make America different.

1. How do you belong?

2. Where does power live?

3. What does participation cost?

Belonging is based on belief and what you build, not blood.

Everywhere else, you belong by ancestry. In America, you belong by buying into an idea and proving yourself in the arena.

17% of countries offer unrestricted birthright citizenship. 5% have true assimilation without strong ethnic barriers.

Most Americans have no idea how rare that is. Because most Americans have only lived in America.

Russia: Dissent is deadly.

Saudi Arabia: religion determines your rights.

China: the state decides where you live, work, and move.

Much of the Middle East: Apostasy and homosexuality are illegal.

Much of Latin America: Lighter skin still buys more opportunity.

In most of the world, where you start is where you finish.

America has class distinctions. But they are far more fluid than fixed.

We know this because immigrants and their children founded 59% of America’s billion-dollar startups. Nearly 80% of US unicorns have an immigrant founder or key leader.

These are not people who arrived with advantages. Many arrived with nothing. They won because America asks two questions that no other country asks.

Do you believe the American dream can work for you?

What are you going to build?

Distributed power. The Declaration of Independence, the Bill of Rights, and the Constitution all share power vs. concentrate it. Checks and balances ensure this stays true. 5-10% of countries have legit co-equal branches of government and strong judicial review.

A relatively low price of participation. Taxation without representation was one of the original ways America was framed, named, and claimed. The US is in the bottom 20-30 percentiles for tax rates as a percent of GDP. America lets you keep more of what you make.

If you look at the Venn diagram of all three, you have one country out of the entire world.

Here’s more Category Science on how $100 of US GDP flows. The American dream can’t exist if you can’t keep enough of what you make.

We created another chart to bring this to life.

• X-axis is how you belong (blood on one end, belief on the other).

  • We use Gallup data on which countries have the most demand to immigrate to.

  • China was excluded from that data, so we used a comparable Gallup data set.

• Y-axis is the government’s cut of GDP, as explained above.

• Bubble size is GDP

• Bubble color is decentralized vs. centralized power.

What do you see? The US is the largest bubble, given its unique cocktail of the three great differences.

China is the second largest, with slightly lower taxes, centralized power, and blood-based belonging.

The Party is Just Getting Started, thanks to Pirate Jevons and his paradox

American GDP went from under $3 trillion in 1980 to more than $30.7 trillion in 2025, a 10x in a single working lifetime. And America stands alone here. In an exceptional way. Most other G7 economies grew only about 4 to 6 times.

AI is going to amplify the three things that make America different.

AI amplifies your ability to build.

Builders drive abundance.

In 1790, the United States of America was a brand-new country. Thirteen colonies. Four million people. Mostly farmers. Estimated GDP: $193 million.

Today, the US has 330 million people. GDP is $30.7 trillion.

No country has ever created more abundance, at a greater scale, for more people, in less time than the United States.

But to understand why, we have to go back in time to one of the OGs of weird data.

In 1865, British economist William Stanley Jevons noticed something weird.

Steam engines were getting more efficient, using less coal to do the same work.

The “smart” economists of the era all predicted the same thing: coal consumption would drop.

The opposite happened.

More effective engines made coal-powered production cheaper. So, more businesses adopted steam power. New value got created. Total coal consumption exploded.

Greater efficiency doesn’t reduce demand for a resource. It increases it.

Because efficiency lowers the cost of doing something. So more people can do it. Which expands what gets done. Which creates entirely new categories of value.

This is the Jevons Paradox.

And it is the most powerful argument against the scarcity premise ever written. Because it proves that value is not finite. Value expands as humans create.

Every time human beings produce an exponential breakthrough. They invent entirely new things to do.

• New categories.

• New demand.

• New value.

Think about what actually happened between 1790 and today.

Americans didn’t just get better at farming. We invented…

• The railroad. Which allowed them to distribute and sell crops further away.

• Electricity. Which allowed them to preserve their crops via refrigeration.

• The automobile. Which let consumers buy and bring crops home.

• The computer. Which allowed you to plan what crops to buy.

• The internet. Which gave you recipes to cook the crops.

• The smartphone. So you can post pics of your cooking.

The world benefited as well. All of this allows folks like Pirate Melissa to create Connected Farms to help bring farmers in Australia, New Zealand, and more out of digital darkness.

AI is next.

Before we look forward to the upside of AI, let’s look back at the internet’s abundance. Because the internet is the most recent and most measurable proof of the Jevons Paradox at society scale.

In 1995, the commercial Internet was brand new. World GDP was approximately $31 trillion. The internet economy was essentially zero.

Over the next 30 years, world GDP grew from $31 trillion to approximately $110 trillion.

Nearly $80 trillion in new value. The internet didn’t redistribute wealth. It helped create it.

McKinsey Global Institute research found the internet accounted for 21% of GDP growth in developed economies during its peak adoption years.

If measured as a sector today, the digital economy is bigger than agriculture or energy.

The World Bank now estimates the global digital economy at $16 trillion. Roughly 15% of all world economic output. And, world GDP totaled approximately $31 trillion in 1995.

Which means the internet category created new digital value worth more than half of everything the entire world produced in 1995.

(Read that twice.)

This is the Jevons Paradox playing out in real time.

The internet made communication, commerce, and information radically different. And instead of reducing demand for those things, it exploded demand. New categories were designed that hadn’t existed before. (New categories create more new categories.)

Let’s look at two scenarios.

Scenario 1: AI Matches The Internet

World GDP today: $110 trillion.

If AI creates the same proportional value as the internet (half of today’s world GDP), that is $55 trillion in new economic value. Created from nothing. Over the next 30 years.

Scenario 2: AI Is Twice The Internet

World GDP today: $110 trillion. If AI creates twice the proportional value of the internet over the next 30 years, that is $110 trillion in new economic value.

Sounds crazy?

• Goldman Sachs projects AI will raise global GDP by 7% over the next ten years.

• PwC projects AI could contribute $15.7 trillion to global GDP by 2030 alone.

• McKinsey says between $2.6 and $4.4 trillion in new value.

Every year. Compounding.

The argument we’re making is to let our winners ride.

Remember Masa?

What if Masa wasn’t allowed to let his winners ride? What if his wealth was redistributed versus reinvested?

This is the future that would have been prevented. Masa’s company Softbank, went public in 1994, when this chart started. Credit to Ryan Petersen, CEO of Flexport, for this legendary post.

We’re not saying all of this is because of Masa.

But a lot of it was because of Masa and the mission he inspired others to follow along. And while Masa is legendary, there are many more Masas in America.

Many people who believe in redistribution are decent, compassionate human beings who look at inequality and feel genuine moral discomfort.

We feel that too.

The question is not whether redistribution can help. But when and how redistribution happens.

The Pilgrims of America decided that redistributing the early US GDP of $193 million might be better off re-invested. And they were right, to the tune of $30.7 trillion.

We’re saying let ‘the when’ compound longer. Because sharing a quadrillion-dollar pie is sure to be more exciting than sharing a trillion-dollar pie.

Let’s leave the how for another mini-book.

What follows are 25 predictions for the next 25 years, across six arenas: AI, Space, Health, People, Money, and what makes America exceptional. Each one leads with why it matters to you, shows the weird data underneath it, extrapolates to a window, and ends with what must be true for it to happen.

What you’re about to read is unapologetically optimistic.

We know the world is complicated and the problems are real. But it is easy to be pessimistic. It can make you seem smart.

We believe you can be honest about the problems and optimistic about future solutions.

More than one thing can be true.

We also know predictions can be hard to get right. As Nobel Prize-winning physicist Niels Bohr put it: “Prediction is very difficult, especially if it’s about the future.” We are very confident in the trajectory and less so on timing.

But we have faith these can be accomplished in the next 25 years.

Optimism requires believing that human ingenuity, American audacity, and the compounding force of new categories can do what they have always done.

Happy birthday, America!

Space

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