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

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

Welcome to the Pirate Street Journal. The Wall Street Journal covers companies. We 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. State Farm is fighting to keep the customers it should fire.

Progressive just took the personal auto crown State Farm held since World War II. It sells more than half its policies direct. No agent.

State Farm’s answer: fly 19,000 agents to Vegas, throw a Pink concert, then tear up their contracts. Sign a worse deal by 2027 or take a buyout. Gross income could drop 40%.

Did the CEO read the data right? No.

He saw customers leaving and built a playbook for the wrong one.

The switcher. Shops every renewal, picks the lowest number, gone the second someone is cheaper. State Farm has paid to chase that customer for decades. So has everyone else.

The superconsumer. Never shops at renewal. Loves coverage, wants more, compounds lifetime value.

The supers are already in the data, hiding behind non-obvious signals: too much life insurance, a thing for gummy vitamins, three or four refrigerators, a household that was ready when COVID hit. The super of one is the super of nine. The generator buyer is the insurance buyer.

Mistake one: chase switchers instead of finding the supers already in the data.

Mistake two: dismantle the agent network instead of backing the proactive agents over the reactive ones.

Cut the switchers and the company shrinks while profit climbs.

2. P&G is selling the technology when it should be selling the problem.

P&G owns 60% of US detergent. Tide alone is close to 40. They spent a decade building Tide Evo, a dry three-inch tile. Since March it has taken 0.6% of the category.

A consultant on the record cannot name the problem it solves at twice the price of a pod. Why?

Because P&G is selling the tile, not the problem.

Market the product and the customer thinks you want their money. Market the problem and they think you want to help.

The problem is real and unspoken: Evo takes the water out. Easier to carry. Does not burst like a pod. Works in cold water, so you skip the heat and the cost.

The superconsumer is the older, fixed-income customer who cannot wrestle the jug anymore. P&G is hiding from her because they think a niche shrinks the mass market. It does the opposite. Niching down expands word of mouth, which expands the market.

Removing water is a category move a century old:

• Nestlé, 1867. Dehydrated milk to reach babies fresh supply could not. It built a food empire.

• Keurig. Sold coffee as a concentrate waiting for the water you add.

• Starbucks Via. Reinvented instant coffee so completely it refused to call it that.

• SodaStream. Ships the syrup and lets you pour the rest.

Every decade, someone strips the water out of a wet product and unlocks a category.

Pull the water and you pull it from manufacturing, packaging, the truck, and the shelf. At scale the tile should hit a 70% gross margin, well above liquid Tide near 50 and pods around 60. The retailer moves the same revenue in less shelf space.

Name what you built and you own no-water detergent, plus every aisle where removing water applies next. P&G has not framed, named, or claimed any of it.

3. America has a supply problem. Singapore had a category problem.

America is short 1 to 5 million homes. The whole debate is supply: smaller lots, granny flats, less red tape. Starter homes used to be a third of everything built. Today they are 10%.

Singapore refused the premise and built a different category. Public housing engineered for longevity and connection. Vertical villages that stack senior apartments, a medical center, and a preschool in one building. Elder care next to four-year-olds on purpose.

The data is the strange part.

• Life expectancy is up about 20 years since 1960.

• Centenarians doubled in a decade.

• Singapore is now the sixth blue zone on Earth, and the first one a government built from scratch.

The residents with the most assets are the elderly, and they use the most healthcare, so they quietly cover the fixed cost of the building everyone else lives in. Co-living solves loneliness at both ends of the barbell, the young who have not started families and the old who outlived their friends.

The Wall Street Journal covered the shortage and missed that the answer already shipped, with 20 extra years of life attached.

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

We just told you what is happening to three categories.

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

Take this to them this week:

• Find your supers through the non-obvious signals. Tell the bots what you sell and have them spec who quietly buys too much of it, the way the generator buyer keeps three refrigerators. The super of one is the super of nine. State Farm is chasing switchers and ignoring the supers in its own data.

• Sell the problem, not the technology. Tell the bots what you built and have them name the problem it solves, then frame it, name it, and claim it. P&G took the water out of detergent and only talked about the tile.

• Turn your shortage into a category. Tell the bots a problem everyone in your space calls a supply problem and have them rebuild it as a category problem. Singapore turned a housing shortage into 20 extra years of life.

Not a founding member yet? You can join here.

What’s coming up on Pirate Street 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.

Subscribe now

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

Welcome to the Pirate Street Journal. The Wall Street Journal covers companies. We cover categories. Each week, we pick three headlines worth paying attention to and break down the category underneath. Read the news through a different lens.

Subscribe now

Dear Friend, Subscriber, and Category Pirate,

AI Memory is going from Commodity to Transformation in record time.

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.

• In volume 1 on May 22, 2026, we said AI hardware was about to re-rate. Micron is now up 61% and just posted the best quarter in its history.

• 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. Stock IPOd at $135, traded up to $202, and is back at $153 as of June 25, 2026.

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 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

Hey ho, let’s go!

Piratey disclaimer. This is NOT financial advice. None of us have a Series 7, a Series 63, a CFA, CPA or an IUD. Think of this like professional wrestling. It is entertainment and category design education. Do not be so smart you get stupid and suplex your savings.

1. Donkeys in a Blender = Business Media Today

That’s what business media sounds like right now.

AI is going to change everything. AI is overhyped. Nvidia is the most important company in history. Nvidia is the next Cisco. Markets up. Markets down. Buy. Sell. Panic. Repeat.

It’s not just exhausting.

It’s wrong.

Not wrong on the facts. Wrong on the frame.

Business media covers companies. So when a company beats earnings, they cheer. When a company misses, they panic. When a CEO announces a $50 billion stock buyback, they speculate about desperation or genius for three news cycles and move on.

What they never do, what they are constitutionally incapable of doing, is ask the only question that actually matters:

What is the category doing?

This is not a small distinction.

It is the difference between noise and signal.

It is the difference between reacting and seeing.

It is the difference between following the herd and building generational wealth while the herd calls you an idiot.

Categories make companies. Companies do not make categories.

Read that again slowly.

Because once it lands, you cannot read business news the same way ever again.

2. This is About the Memory Category, Not Just Micron.

Five weeks ago, we said AI hardware was about to re-rate.

Not a company. A category.

The donkeys screamed about the AI trade being on, then off, then on again. The Wall Street Journal went superficial (“the AI rally is officially back on”) as if anyone who understood real market categories ever thought it was off.

We weren’t looking at a company.

We were looking at a category in the middle of perhaps the fastest transformation in modern market history.

From commodity to transformation.

Memory was no longer a cyclical commodity. It is core to the AI experience, and AI is way early innings. Pirate AJ on X, the best and most different Wall Street Analyst, said it plainly, “AI Hardware is the endgame.” We stand on the big shoulders of his one-of-one analysis, and Pirate Eddie gladly pays $500/month for his POV.

Micron’s stock has more than tripled this year. It is up more than seven times in the last twelve months. 14 out of 18 trading days in June 2026, Micron has been one of the top three highest dollar volume of trading in the entire stock market.

So what happened?

Read more

Welcome to the Pirate Street Journal. The Wall Street Journal covers companies. We cover categories. Each week, we pick three headlines worth paying attention to and break down the category underneath. Read the news through a different lens. Become a paid subscriber to access the monthly deep dive.

Subscribe now

Dear Friend, Subscriber, and Category Pirate,

On June 12, SpaceX is going public at $135 per share and a $1.75 trillion valuation.

4% of total shares are being offered. Of those, 30% have been allocated for retail investors to buy directly at the $135 IPO price. The standard retail allocation in a mega-cap IPO is 5 to 10% of shares, with the overwhelming majority reserved for large institutional buyers like pension funds and mutual fund managers.

SpaceX is tripling that, which is unusual.

At a $75 billion raise, that is roughly $22.5 billion in shares flowing directly to retail. More than many entire IPOs.

One of SpaceX’s lead underwriters told Reuters they had never seen anything like the expected retail demand.

Both Anthropic and OpenAI have also filed to go public sometime this fall.

It is a mad rush to raise capital to fund the AI infrastructure buildout. Valuations defy gravity and become a moving target as ARRs change every month and cash-burning businesses like xAI flip to cash-flowing with the stroke of a single deal.

IPOs Are Dangerous, Right?

Read more

Welcome to the Pirate Street Journal. The Wall Street Journal covers companies. We cover categories. Each week, we pick three headlines worth paying attention to and break down the category underneath. Read the news through a different lens.

Subscribe now

Dear Friend, Subscriber, and Category Pirate,

Last week, we recorded the very first episode of the Pirate Street Journal.

The Pirate Street Journal is for leaders with a different mind.

A different take on business news.

Through the category lens.

Our mini-books are timeless. PSJs are timely.

Our mini-books are long stories longer. PSJs have 30-minute seat belts.

Our mini-books are thinker’s high. PSJs try to help you think before you act.

But, but, but, but…

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

Think of this like professional wrestling. It’s entertainment.

Don’t be so smart, you’re stupid and suplex your safety net savings.

Hey Ho, Let’s Go!

PSJ is the new weekly thing. The video’s free. The deep-dive written analysis is paywalled. Watching makes you informed. Reading makes you different.

Two ways to climb aboard:

• Monthly subscriber: $20/month. You’ve done dumber things with $20.

• Founding subscriber: $375/year. For about a dollar a day, you get every mini-book we’ve ever written (300+), every audiobook (30+), digital copies of all seven of our Big Books, and unlimited access to The Pirate Eddie Bot and Pirate Christopher Bot, your 24/7 AI jamming partners for category building.

To read this week’s deep dive, become a subscriber today.

1. Why is Salesforce down? Why is Micron up?

Read more

Welcome to the Pirate Street Journal. The business press covers companies. We 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. SpaceX’s $60 billion dollar bargain.

SpaceX bought Cursor, the AI coding startup, for $60 billion in stock.

Four MIT students built it in 2022, the CEO is 25, and a team in the low hundreds already throws off billions in revenue against Claude Code and Codex.

Did Musk overpay? No.

There are two kinds of acquisitions.

Consolidation: One buys a rival in a flat category and strips out the duplicate cost. That is what most people picture.

Acceleration. You buy the king of a category about to explode.

Cursor’s founder said he built a new type of software, a category for building AI software with AI. Microsoft bought DOS. Google bought YouTube. Facebook bought Instagram. Each one looked overpriced for the same reason.

2. Government f’d the grid. Consumers can fix it.

Two weeks ago we said the power layer of the AI stack is nearly empty, with about $156 billion of US data center projects blocked or delayed.

The Government is the source of gridlock when it comes to upgrading the grid.

Consumers to the rescue!

In Germany, more than a million households installed plug-in solar. You hang panels on a balcony, plug into a wall outlet, and run in under an hour. Each one is capped around 800 watts.

Utah went first last year. Several states have legalized it since, and more than 30 are now considering it.

A starter kit runs a few hundred dollars and pays for itself in a few years where power hits 30 to 40 cents a kilowatt-hour.

Rooftop solar stayed a luxury because of permits and cost. Strip those away and a new category shows up: distributed, consumer-owned power at Costco prices.

3. KFC put a bandaid on broken Category Design

KFC is 74 years old, 34,000 restaurants, over 150 countries, and just announced the biggest overhaul in its history.

New sauces, a boba drinks line called KWENCH, interiors built like an Apple store crossed with a Vegas sphere, new logo.

But this is merely a bandaid on broken Category Design.

KFC has more US locations than Chick-fil-A. But Chick-fil-A does about $7.5 million per store or four times higher with one fewer day per week.

Why?

Four things matter to Quick Serve Restaurants (QSRs)

1. Speed of service

2. Drive through

3. Beverages

4. Culture

Simple menus drive speed of service. KFC is complicating an already bloated menu.

Drive through is 70% of QSR revenue. Chick-Fil-A has masterfully re-designed the drive through with mobile orders, double drive through lanes and early outdoor order takers. KFC drive through news was crickets.

Boba and screens redecorate the magic triangle without refreshing it.

But Chick-fil-A’s culture edge is the ownership model: private, anti-franchise, a $10,000 buy-in, an acceptance rate under 1%.

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

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

Take this to them this week:

• Sort your next big bet into consolidation or acceleration. Ask the bots which moves in your space buy a category king and which only buy cost savings. Musk just paid $60 billion to own the top of a stack he didn’t build.

• Find the abundance play in your category. Tell the bots what you sell and have them spec a version that gets cheaper and better the more people use it, the way a million balconies beat one. Then ask where the network effect kicks in and how this is relevant to you.

• Stress-test your own glow-up. Tell the bots what you are about to change and have them split it into surface redecoration and real category design. KFC is spending its biggest budget ever on boba while Chick-fil-A makes four times per store.

Not a founding member yet? You can join here.

What’s coming up on Pirate Street Journal

Every week, we drop the podcast. Three topics, thirty minutes, one cowbell.

Once a month, we publish a written deep dive, the kind of category analysis you cannot get anywhere else. That one is for paying subscribers only, monthly and founding.

Two ways to climb aboard now:

Monthly subscriber: $20/month. You’ve done dumber things with $20.

Founding subscriber: $375/year. For about a dollar a day, you get every mini-book we’ve ever written (300+), every audiobook (30+), digital copies of all seven of our Big Books, and unlimited access to The Pirate Eddie Bot and Pirate Christopher Bot, your 24/7 AI jamming partners for category building.

Subscribe today and start jamming with the bots.

Recorded Friday, June 12. Every number above is as of that morning.

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

Stay tuned for next week’s episode.

Hey Ho, Let’s Go!

Arrrrrrr,

Category 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,

A few weeks ago we dropped Motherhood 3.0.

Motherhood 1.0 stayed home. Motherhood 2.0 tried to do everything at once and got penalized for it. Motherhood 3.0 uses the Four Capitals to separate income from time, so a mother can integrate her career and her family instead of compromising between them.

So the obvious question is, what about fathers?

So we did what Category Designers do. We went to the data, we went to our own scars, and we went looking for the false choice nobody was naming.

You don’t have to read Motherhood 3.0 first. But you should read it second, since we all have mothers and know mothers.

Three versions of fatherhood are on the table. Each one solved the previous one’s problem and created a new one.

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

Listen to the Audiobook

Fatherhood 1.0 was the provider. Powerful at work, mostly absent at home. He paid for the house, married his career, and his kids barely saw him.

Fatherhood 2.0 was the corrector. He looked at what 1.0 cost him and resolved to be there. He coaches the team, runs the carpool, and shows up to every recital. And he is exhausted, stretched, and quietly unsure whether any of it is working.

Fatherhood 3.0 refuses the trade. He uses the Four Capitals of the Creator Capitalist, Financial, Reputation, Relationship, and Intellectual, to break the chain between time and money. He is present and powerful at the same time. Because he designed his life on purpose instead of inheriting someone else’s blueprint.

The cost of getting this wrong is not theoretical. In 1.0, the cost is the kid. In 2.0, the cost is you. In 3.0, the cost is the courage to design a life nobody handed you.

(P.S. Courage is one of the most legendary things an adult can teach a kid. Especially in a world so lacking in it.)

Fatherhood 1.0: The Cost. The Fall Of The House Of Busch

Pirate Eddie was serving Anheuser-Busch as a consultant starting in 2006.

August Busch IV became CEO of AB in November 2006. However, the shadow of his father August Busch III, also known as The Chief, loomed large.

The Chief ran Anheuser-Busch from 1975 to 2002. Under his leadership, AB share of the US beer market grew from roughly 25 percent to 48 percent. Bud Light became the largest beer brand in the world. His team designed the wholesaler incentive plan that turned 800 independent distributors into a powerful beer salesforce that stacked pallets of Bud Light high and watched them fly. Then funneled the distribution muscle into a billion-dollar marketing budget that produced the most iconic commercials of the 80s and 90s.

The Chief was a force.

Meetings did not start when they were scheduled. They started when the Chief walked in. Senior executives showed up forty-five to sixty minutes early to every meeting because nobody wanted to be the person not in the room when the Chief arrived, often by a helicopter he was flying.

He was also a Fatherhood 1.0 dad.

The Chief divorced his first wife when his son August Busch IV was five. The Fourth was raised by his mother. The public record on the father-son relationship is brutal in its brevity: “His time with his father was mostly spent at the brewery, and their relationship was, for the most part, professional.”

The Fourth spent his whole career trying to climb out of that shadow. He ran AB’s marketing in the 1990s and won ten consecutive USA Today Super Bowl Ad Meter awards. He led domestic beer operations. He was the president of the company by 2002.

And still the Chief made him wait. The Chief broke with tradition and installed a caretaker CEO, Patrick Stokes, for the next four years, because The Fourth was not deemed ready. The unspoken price of admission to the top job, according to people inside the company at the time, included settling down. So on August 5th, 2006, at age 41, The Fourth married a 25-year-old woman from Vermont named Kathryn Thatcher.

To win back market share from rising imports like Heineken, The Fourth invited InBev into a US distribution partnership. That gave AB Stella Artois, Beck’s, and Bass. He thought he was solving a sales problem.

He was letting the fox into the henhouse.

InBev’s CEO Carlos Brito is an OG of 3G.

3G is one of the most effective LBO teams in the history of the world. It was founded by Jorge Paulo Lemann, Marcel Telles, and Carlos Sicupira. They niched down into beer, where they were the most effective. In 1989, they bought a Brazilian brewery, Brahma, for $52MM with mostly debt.

Two decades later, they bought Anheuser Busch for $52 billion dollars.

At that point, they had perfected their playbook. They ran the most ruthlessly effective LBO playbook in the world. Buy breweries with mountains of debt, apply zero-based budgeting to strip costs to the bone, load the top 200 leaders with options, and watch everyone get rich on the squeeze.

Brito got inside Anheuser-Busch on a sales partnership, saw the bloat from twenty feet away, and submitted what amounted to a hostile takeover within two years.

When the offer came, the Chief was Chairman of the Board. He had a choice. Back his son, the CEO he had spent forty years grooming

Or back the Brazilians who proved their ability to unlock billions over 20 years.

He backed Brito.

The board approved the sale in November 2008. The same month, The Fourth filed for divorce. The company his great-great-great-grandfather founded, an American icon, became a subsidiary of a Belgian-Brazilian holding company. The Fourth took a board seat on the merged entity and stepped out of public life. The years that followed were the saddest stretch of a public life this country has watched in a long time.

The Chief did not give his son too little professionally. He made The Fourth work his way up. He made The Fourth settle down.

The Chief showed his son his power more so than his presence.

The Fourth tried to wield the power in order to get his father’s presence.

And in the end, The Fourth ended up with neither the power of his father, nor his presence.

This is the cost of Fatherhood 1.0. Not absence in the simple sense of not being home. Absence of the only relationship currency the son was trying to earn. The Chief built a $52 billion company and could not give his son the one thing his son wanted. The Fourth received everything except agency, and the moment the real test came, he had no scar tissue to draw on.

A father who only knows how to be powerful will sometimes lose the only thing power was supposed to protect.

Fatherhood 2.0: The Well-Meaning Trap. Steve Martin In Parenthood

In 1989, Ron Howard made a movie called Parenthood.

Pirates Christopher and Eddie love this movie.

It’s hilarious, awkward, and truthful.

Steve Martin plays Gil Buckman, a marketing guy at a consumer-goods company who is trying very hard to be a different kind of father than his own. His father, played by Jason Robards, is a Fatherhood 1.0 man: distant, hard, mostly absent, occasionally cruel. Gil has decided he will not do that to his son.

So he does the opposite of everything his father did.

He coaches the Little League team. He shows up to the school plays. He puts on a cowboy costume at the birthday party and turns himself into a balloon-animal entertainer when the hired clown does not show. He bends his entire life around being present for his kids, especially his oldest, who is struggling with anxiety. He is doing every single thing his father did not do.

(He turned himself into a donkey.)

And he is dying inside.

There is a scene where Gil’s wife, played by Mary Steenburgen, finds him sitting on the bed mid-meltdown. He is exhausted. His career is stalling because he refuses the relocation that would advance it. His marriage is strained. He is convinced his kids are going to come out broken anyway. He gave up the part of his life that made him most himself, told his kids it was love, and slowly became unrecognizable to himself.

Steve Martin says, “My whole life is ‘have-to’.”

This is a man without any agency in his life. He’s present, but not powerful.

That is Fatherhood 2.0 in a single character.

The data on real-life fathers confirms it. Net-net, fathers spend less time at work and more time caring for kids, driving kids and housework.

Fatherhood 2.0 dads are working hard and parenting hard, and feeling like they are failing at both.

Because presence by itself was never the whole answer.

Kids used to watch their fathers work. The farmer in the field. The shopkeeper behind the counter. The tradesman at the bench. They saw their dads creating value. Doing work they were good at. Successful at. They saw their fathers being a man’s man.

Then fathers went to offices, and what kids saw came home with the lights off. The work happened somewhere they could not see, and what they got at the dinner table was a tired man with very little left.

Fatherhood 2.0 corrected the absence and lost the witnessing.

That is the cost to fathers and families.

When a man’s wife rarely sees him performing at his best, that’s not good for the marriage or the children. Gil Buckman (Steve Martin) in his bedroom is the icon of the generation. A man who showed up to everything and quietly disappeared from his own life.

What is the point of showing up, only to vanish from the room?

Men without power and agency are never right in the head. Men who fall short of their potential are devalued by themselves and the world. It causes a man to spin out.

Harsh, but true.

Men who over-rotate on being powerful at the expense of being a great father are also judged harshly by the world. They may say they don’t care, but there are massive unintended consequences that lead to regret and loneliness.

Both are problematic.

Fatherhood 3.0: The Way Out

The 3.0 father makes three moves, in this order.

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

Welcome to the Pirate Street Journal. The business press covers companies. We cover categories. Each week, we pick three headlines worth paying attention to and break down the category underneath. Read the news through a different lens.

Subscribe now

Dear Friend, Subscriber, and Category Pirate,

Gartner grew its revenue again last year.

Yet investors wiped out more than $30 billion of its value anyway.

The stock fell from $551 to $155 in about twelve months.

Still profitable. Still growing. Still the name every CIO knows.

Wall Street just stopped believing it has a future worth paying for.

The business is fine. The future got repriced.

Here’s what we covered in this episode:

1. Gartner is Going Through the Grinder

For 40 years, Gartner was the company you paid to tell you what tech to buy. It peaked at $551 a share in November 2024. This week it trades around $155, a 74% collapse, with market cap down from roughly $42 billion to about $10 billion.

Within consulting, true strategy work is about seeing the future and taking action.

Roger Martin pegs true strategy at about 3% of what the big consulting firms sell.

The vast majority of consulting is copying and pasting the past. Also known as benchmarking. Or best practices. Or gap analysis.

It is formulaic. It is paint by numbers. It’s monkey see, monkey do.

And why AI does it 10x better, faster and cheaper.

That is why Gartner’s future has less value.

2. OrangeTwist’s Lightning Strike Printed Profits

A top medical spa company called Orange Twist ran a Lightning Strike in Newport Beach called TwistX.

It was a mid-six-figure event at the Hyatt that turned a profit. Vendors covered about a third (30 brands paying to get in front of buyers), consumers covered about a third ($250 a head at the door), and on-the-spot treatment bookings covered the rest.

A Lightning Strike concentrates a year of marketing budget into one moment instead of spreading it thin across twelve. Pulled off right, it pays for itself, which flips marketing from cost center to profit center.

OrangeTwist’s TwistX was a massive hit.

And it’s only going to get bigger and better.

Learn how they did it.

3. Teen summer jobs are declining. That’s ok.

Teen workforce participation peaked near 58% in 1979, and the share holding a job has fallen from 49% to 31%.

The decline is almost entirely teenagers opting out of jobs that make a buck, but don’t prepare them for the future.

Smart teens are trading out retail jobs for AI native jobs.

Jobs that don’t pay minimum wage, but show you how to make $30,000 before you turn 18 use AI skills adults don’t have today.

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

We just told you what is happening to three categories. The bots help you figure out what it means for yours. Reading the news is the easy part. Turning it into a move you can make this week is the part most people skip, and it is exactly what The Pirate Eddie Bot and Pirate Christopher Bot are built for. They jam with you 24/7, they come with the founding tier, and they never get tired of your follow-up questions.

Take this to them this week:

• Find out what your knowledge work is actually worth. Ask the bots which parts of your job repackage existing knowledge and which parts create net-new. Gartner just lost $30 billion proving the market only pays for one of them.

• Spec a Lightning Strike for your category. Tell the bots what you sell and have them design one concentrated moment that could pay for itself, the way TwistX did. Then ask them where it would break.

• Run the teenager’s playbook on yourself. Hand the bots $30,000 and a laptop and have them build a net-new business using the Four Capitals. The 18-year-old’s edge works at any age.

Not a founding member yet? You can join here.

What’s coming up on Pirate Street Journal

Every week, we drop the podcast. Three topics, thirty minutes, one cowbell.

Once a month, we publish a written deep dive, the kind of category analysis you cannot get anywhere else. That one is for paying subscribers only, monthly and founding.

Two ways to climb aboard now:

Monthly subscriber: $20/month. You’ve done dumber things with $20.

Founding subscriber: $375/year. For about a dollar a day, you get every mini-book we’ve ever written (300+), every audiobook (30+), digital copies of all seven of our Big Books, and unlimited access to The Pirate Eddie Bot and Pirate Christopher Bot, your 24/7 AI jamming partners for category building.

Subscribe today and start jamming with the bots.

Recorded Friday, June 12. Every number above is as of that morning.

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

Stay tuned for next week’s episode.

Hey Ho, Let’s Go!

Arrrrrrr,

Category Pirates

Eddie Yoon

Christopher Lochhead

Dear Friend, Subscriber, and Category Pirate,

We loved celebrating all the moms in our lives a few weeks ago over Mother’s Day, and now it’s time to celebrate the dads.

Before we get into the episode, we have something fun to share.

The Parent Bundle and a Father’s Day offer

This week we’re launching the Parent Bundle, and if you sign up as a new Founding Subscriber between now and Father’s Day, you’ll get the full bundle included at no extra charge.

Here’s what’s inside:

• The Joy Book: written by Pirate Eddie’s daughter Audrey (when she was in 6th grade), this physical book is available individually for $25 (more on this below)

• How To Build Your First (Crazy Profitable) Business As A Teenager Vol. 1: 18 radical ideas for Native Digital entrepreneurs. The original. Available individually for $12.99 on Amazon here.

• How To Build Your First (Crazy Profitable) Business As A Teenager Vol. 2: the AI sequel: 18 more ideas built for the era of AI co-founders and $30K summers. Available individually for $12.99 on Amazon here.

Know a dad who needs this? Share this post (and next week’s mini-book: Fatherhood 3.0) with him. Know a teen who should read the AI book? The Vol. 1 and Vol. 2 links are right there. And if you just want the whole stack for yourself, the $40 full physical bundle has you covered.

New Founding Subscribers who sign up before midnight PST on June 21 get the full physical bundle free.

If you’re already a Founding Subscriber, watch your inbox for a digital version of the Joy.

If you’re ready to hop aboard, you’ll get the Parent bundle on the house and immediate access to the Pirate Eddie and Christopher Bots (your 24/7 category design jam partners), access to our full audiobook library (35+), and the entire Category Pirate library (including all 7 of our big books and 300+ mini-books).

→ [Become a Founding Subscriber and get the Parent Bundle included here.]

Now. To the episode.

Fatherhood 1.0 left the building. Fatherhood 2.0 showed up. Fatherhood 3.0 might be the most important design challenge yet.

A generation ago, fathers worked.

That was the job. Leave it to Beaver dads were providers, not participants. Fatherhood 1.0 was simple, if you squinted past how hollow it actually was.

Then the data shifted. Today’s fathers spend 90 minutes a day on childcare in the United States, up from 20 minutes in 1985. In Canada, the number tripled. Globally, across Germany, Norway, Japan, Australia, the arc is the same: fathers are more present than any prior generation.

So why does it still feel like a false choice? Why does “legendary career” still seem to compete with “legendary father”?

In this episode, Pirates Eddie, Christopher, and Bri dig into what that tension actually is, and where it comes from. And the answer is more interesting than “you need better balance.”

The problem with Fatherhood 2.0 isn’t the quantity of time. It’s what children see when they have it.

The most powerful gift a father can give has nothing to do with attendance

Pirate Christopher’s late therapist, David Willingham, put his finger on something that the modern parenting conversation has mostly missed.

For generations, children watched their fathers work. Farmers, shop owners, craftsmen, small business owners: the work happened at home or nearby, and children saw their fathers being excellent at something. As the economy shifted and fathers disappeared into offices, children inherited a different version of fatherhood: a man who came home tired.

Present, maybe. But not at his most powerful.

The Creator Capitalist unlock here runs parallel to what we explored with Motherhood 3.0: when you separate your time from your income, you don’t just get agency over your schedule. You get to show your kids what it looks like when you’re actually doing the thing you were built to do.

Not a watered-down, weekend version of yourself. The whole thing.

Pirate Eddie walked through the math of his own career, making partner in consulting while his kids were young, traveling constantly, trying to be present on the weekends while his wife, Pirate Kristen, carried the weight at home. He’s candid about what the tradeoffs cost. But Pirate Christopher reframes the ledger: Eddie’s kids didn’t just miss time with their father. They watched their father build something legendary. And those two things aren’t in opposition.

The false choice of Fatherhood 2.0 is: you can have a great career OR you can be a great dad. Pirates reject that premise entirely.

The Joy Book: what Pirate Eddie’s daughter actually thinks

Speaking of what kids absorb.

Audrey Yoon wrote a book about growing up with Eddie as her father. The title is deliberately not spoiled here. What we’ll say is this: her early memories include a 6 a.m. birthday breakfast before a 9 a.m. flight. Pirate Eddie tells the story with some sheepishness in the episode. Audrey tells it as one of her favorites.

Kids see differently than we think they do.

Here’s a sneak peek at what’s inside (read to you by Pirate Eddie and animated by his oldest daughter, Miya):

The Joy Book is available now in the Shopify store, individually for $25, and bundled in the Parent Bundle for $40. It was written by Audrey, and it is the most honest accounting of Fatherhood 2.0 you will find.

Here’s how to navigate this conversation:

• 0:00 – Tom Peters and the Creator Capitalist origin story: Pirate Eddie and Christopher open with Roger Martin’s X post and land on Tom Peters as one of the original creator capitalists, which sets up everything that follows about what it means to make your own place rather than fit into someone else’s.

• 7:33 – The four capitals and the fatherhood problem: Pirate Christopher pivots to the core thesis: trading time for money is what breaks both fatherhood and financial capital.

• 14:00 – The data that got Pirate Eddie thinking: Pirate Bri shares the charts. Fathers globally are tripling their childcare time. The numbers are real and they set up the hard question: why isn’t it working the way we thought it would?

• 18:27 – Pirate Eddie’s honest accounting of his own career as a father: Partner while the kids were little, global travel, Kristen carrying the weight. He doesn’t spin it. He walks through what he would do differently, and what he wouldn’t.

• 24:00 – The therapist’s point about watching your father work: Pirate Christopher shares Willingham’s thesis: multiple generations ago, kids witnessed their fathers being excellent. Then offices happened. This is where the episode shifts from data to category design.

• 29:00 – Rejecting the false choice: Pirate Christopher lands the argument. Legendary career OR legendary father is a premise to reject, not a trade to manage. The Creator Capitalist path is what breaks the chain.

• 45:00 – Parenting never ends, and that’s the most terrifying insight: Pirate Eddie on what it looks like when the problems level up from “don’t touch the stove” to “what do you do when your kid marries the wrong person.”

• 47:07 – Pirate Christopher’s six-and-a-half years: Tushar’s murder, Michael’s death, COVID, the DA, 2,407 days to four life sentences. What children see when they watch the adults they love stand back up.

• 57:19 – Pirate Bri’s reader’s digest: The daughter’s perspective, her dad’s absence, and the question she’s watching her generation not quite answer yet: what does Fatherhood 4.0 look like when kids who had all the presence grow up?

Fatherhood 3.0 is the design problem worth solving

Fatherhood 1.0 was presence-optional. Fatherhood 2.0 added presence and kept the career, and then wondered why the tradeoffs were still brutal.

Fatherhood 3.0 asks a different question: what if you could stop choosing?

Next week we’re releasing the Fatherhood 3.0 mini-book. If you haven’t already, go read the Motherhood 3.0 mini-book first. The theses are designed to be read together.

And if this episode hit differently, Audrey’s book is the version of this story told from inside the house.

Go get the Parent Bundle. Come back next week. And in the meantime, do something legendary in front of your kids.

Arrrrrrr,

Category Pirates

Eddie Yoon

Christopher Lochhead

P.S. The Parent Bundle is live, and new Founding Subscribers get it free through Father’s Day.

The Joy Book ($25 individually), AI Teen Books Vol. 1 and 2, are all bundled together for $40. New Founding Subscribers who sign up between now and Father’s Day get the bundle included at no extra cost. Existing Founding Subscribers get digital versions on the house.

The Pirate Eddie Bot and Christopher Bot also come with your Founding subscription, so you can start working through your own category design any time.

→ [Become a Founding Subscriber and get the Parent Bundle here.]

Welcome to the Pirate Street Journal. The business press covers companies. We cover categories. Each week, we pick three headlines worth paying attention to and break down the category underneath. Read the news through a different lens. Become a paid subscriber to access the monthly deep dive.

Subscribe now

Dear Friend, Subscriber, and Category Pirate,

On June 12, SpaceX is going public at $135 per share and a $1.75 trillion valuation.

4% of total shares are being offered. Of those, 30% have been allocated for retail investors to buy directly at the $135 IPO price. The standard retail allocation in a mega-cap IPO is 5 to 10% of shares, with the overwhelming majority reserved for large institutional buyers like pension funds and mutual fund managers.

SpaceX is tripling that, which is unusual.

At a $75 billion raise, that is roughly $22.5 billion in shares flowing directly to retail. More than many entire IPOs.

One of SpaceX’s lead underwriters told Reuters they had never seen anything like the expected retail demand.

Both Anthropic and OpenAI have also filed to go public sometime this fall.

It is a mad rush to raise capital to fund the AI infrastructure buildout. Valuations defy gravity and become a moving target as ARRs change every month and cash-burning businesses like xAI flip to cash-flowing with the stroke of a single deal.

IPOs Are Dangerous, Right?

Truist analyst Keith Lerner pulled the data on 30 major IPOs from the last 15 years.

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 🔒 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,

Before we go deep, here’s the TL/DR.

You were born at the exact right moment.

Not because things in the world are perfect. They are not.

But things are a lot better for you than you’ve been told.

Your future is a lot brighter than you’ve been led to believe.

We’re offering you a different lens. On your future. Starting this summer.

That’s if you want to build a business now. Learn something powerful now. Make money now. And set yourself up for a legendary future.

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

Listen to the Audiobook

Because for the first time in history, the tools and technology that used to cost a million dollars and require a team of adults now cost $20 a month and run on your laptop.

AI didn’t just change what’s possible. It nuked the permission structure. All you need now. A little drive. A little focus. A desire to make a difference. And a playbook (this newsletter).

You used to need a boss to give you a job. An investor to give you money. A degree to prove you were worth hiring. A decade of experience before anyone would trust you with real work.

That gate is gone.

The adults around you haven’t figured this out yet. A 17-year-old with one AI summer and one good idea can out-earn a 35-year-old with a LinkedIn profile full of certifications.

We know. Because it already happened. A 17-year-old named Luke helped build a bot that now drives a real business. Not a hobby. Not a science fair project.

A six-figure business with 99% gross margins.

That’s what this is about.

Not AI homework shortcuts. Not going viral. Not “hustling.” Those are all ways to stay broke.

This is about building something that pays you while you sleep. A voice agent, a bot, an automation or a paid newsletter. One of 18 specific, proven, real-money ideas any one of which can put $30,000 in your pocket before you graduate.

$30,000 invested at 18, compounding for 47 years, is $2.6 million at retirement. That math doesn’t care how old you are when you build it.

Three things this mini book is not:

It is not get-rich-quick. Every idea in here requires real work.

It is not cheating. Using AI as a rocket is the opposite of using AI as a cheat code. One makes you better. One makes you dependent.

It is not for someday. Someday is how your parents ended up with a job they’re lukewarm about.

One thing this book is:

Your playbook for the summer that changes the rest of your life.

Pick one idea. Get one customer. Come back for the next one.

The kids who figure this out in 2026 will be the ones everyone else works for in 2036.

Be that kid.

If the next few sections are boring to you, we won’t be offended if you say, “Ok, Boomer” and skip to the 18 AI ideas to make $30,000.

Let’s jump in.

A kid named Jensen.

Jensen was born in Taipei but moved to Thailand from the age of 5 to 9 with his parents.

Then they put him and his older brother on a plane to America to live with an uncle in Tacoma, Washington. They spoke almost no English. And had no money. The uncle did his best and found what he thought was a prestigious boarding school and enrolled them. It was a reform school in Oneida, Kentucky.

The dorms had no closet doors. Some “students” carried knives. Jensen was assigned to clean the bathrooms for a hundred teenage boys. His brother was sent to work in the school’s tobacco fields. They were called ethnic slurs and threatened.

Pirate Jensen still calls it one of the best things that ever happened to him.

His parents eventually moved to the U.S. and the family settled outside Portland, Oregon. He graduated high school at 16. He worked the night shift at Denny’s, washing dishes, then bussing tables, then waiting tables.

He went to Oregon State University.

In an engineering class of 250 students, he met a woman named Lori. He was 17. She was 19. He walked up to her and said, “Do you want to see my homework?”

They have been married for four decades.

At age 30, Jensen and two friends founded a chip company at a Denny’s in San Jose.

That company is Nvidia.

As of this writing, it is the most valuable company in the world. Jensen Huang is the most important CEO on the planet because he runs the company that builds the chips that run AI.

After flying on Air Force One with the President for a big meeting in China, he bailed on the procession and went to eat street food. He still wears the same black leather jacket his wife and daughter picked out for him, not just because it is cool but because other clothing irritated his skin.

Despite all of this and being worth $175 billion plus, he’s still Jensen from the block.

Not all leaders of AI are evil tech bros. Some dance like Uma Thurman.

Some of them are kids who washed dishes at Denny’s and cleaned toilets.

Pirate Jensen is not here to steal your future. He’s helping you build it.

An Expert Predicted AI Would End Radiology. He was wrong.

In 2016, a man named Geoffrey Hinton, who is known as the “Godfather of AI” and who later won a Nobel Prize, stood in front of a room and said this: “People should stop training as radiologists now.” He predicted that within five years, AI would be better than humans at reading medical scans and radiologists would be obsolete.

He was famous. He was credentialed. He was very confident.

Sometimes you can be so smart you’re stupid.

A decade later (2026) a radiologist in America can make as much as $693,000 per year. The American College of Radiology projects the number of radiologists will grow by up from 26% to 40% between 2023 and 2055. Mayo Clinic alone has 400+ radiologists, a 55% increase since Hinton’s prediction. Almost every radiology platform is now powered by AI.

The AI part of the prediction came true.

The “no more radiologists” part went the opposite direction.

Why?

Jensen Huang explained it on a podcast last year. Hinton confused the job with the task. Reading a scan is a task. The job of a radiologist is to diagnose disease. When AI took over the task, radiologists got faster, more accurate, and able to see more patients. Demand for radiologists went up, not down. The bottleneck cleared. The category expanded.

(The pie got a lot bigger. Not smaller)

Hinton himself later admitted he was wrong on the timing and the implications.

No matter who the expert is. Doing your own thinking about thinking, is always wise thinking.

Every time someone confidently predicts AI will destroy a job, what actually happens is the job changes, demand expands, and the people who learned to use the new tech win.

Technology moves where value gets created.

So when someone tells you AI is going to destroy your future, ask them: are you talking about the task, or the job?

AI, Like Most Technology, Leads to Abundance for All

The beauty of Category Design is it makes the overall pie bigger.

Sadly most of what we’ve been taught is that life is a zero-sum game. That’s simply not true. When humans fight over scarcity. Very bad things happen. When humans collaborate we create abundance.

Look at the actual scoreboard of human progress over the last 50 years.

In 1975, the entire world economy was about $6 trillion. Today it’s roughly $120 trillion. That growth came by creating new categories of value.In 1974, the average human could expect to live 58 years. Today they can expect to live 73.

In 1990, 1 in 11 children died before their fifth birthday. Today, it’s 1 in 27. We have cut child mortality by 60% in just 34 years.

In 1990, 36% of the world lived in extreme poverty. Today, it’s 10%. More than 1.3 billion human beings climbed out of extreme poverty in the last 35 years. That is the single largest reduction in human suffering in the history of our species.

In 1976, only 67% of adults on Earth could read. Today, 87.7% can. For women, the literacy rate went from 56.7% to 84.6% in the same period.

Smallpox killed an estimated 300 million people in the 20th century alone. It was eradicated in 1980. Polio is down 99% since 1988. Measles deaths are down more than 80% since 2000.

All of these upgrades came from new categories of technology.

And with every advance, a zero-sum doomer told you the sky was falling.

The biggest zero-sum doomer story is billionaires don’t pay taxes.

Before we plant our identity in a belief, some more thinking about thinking is wise thinking.

In December 2024, The New York Times published a story headlined “How One Of The World’s Richest Men Is Avoiding $8 Billion In Taxes.”

The article reported that Jensen and his wife Lori set up legal trusts: an irrevocable trust in 2012, four GRATs in 2016, plus a private foundation. Those trusts will save their heirs billions in estate tax when Jensen eventually dies.

There is some truth to this.

Yet.

When Jensen was asked about the proposed wealth asset tax in California and said, “I haven’t thought about it even once. We work in Silicon Valley because that’s where the talent pool is. I’m perfectly fine with it, it never crossed my mind once. We chose to live in Silicon Valley and whatever taxes they would like to apply, so be it.”

So what is the truth? Let’s look at the numbers.

Jensen pays a massive amount in income tax in California, at the highest rates in the US.

His total compensation in fiscal 2025 was just under $50 million. About $1.5M of that was base salary. $6M was a cash bonus. $38.8M was stock awards (RSUs). $3.6M other. RSUs are taxed as ordinary income at the moment they vest, just like your paycheck. Jensen lives in California. So his effective tax rate on that comp is roughly 50% once you add federal (37%), California state (13.3%), Medicare, and the additional Medicare surtax.

50% of $50 million is $25 million. In one year. In personal income tax. From CEO comp alone.

His 2024 total comp was $34 million. Same math, same rate, around $17 million in tax.

So just from his W-2 compensation, in 2024 and 2025 alone, Jensen paid approximately $42 million in personal income tax.

He paid roughly $1 billion in capital gains tax on stock sales in the last 18 months.

Between mid-2024 and late 2025, Jensen sold approximately $2.9 billion in Nvidia shares through pre-scheduled 10b5-1 trading plans. These are founder shares with essentially zero cost basis, which means almost the entire $2.9 billion is taxable as long-term capital gains. Federal long-term cap gains tax (20%) plus Net Investment Income Tax (3.8%) plus California (which taxes capital gains as ordinary income at 13.3%) puts his effective rate around 37%.

$2.9 billion × 37% is approximately $1.07 billion in capital gains tax paid by Jensen Huang in 18 months.

The Seattle Times clarifies what the New York Times story buries. “If the Huangs’ trusts sell their shares, that will generate a hefty capital gains tax bill, more than $4 billion.”

The “$8 billion saved on estate tax” headline implies zero taxes paid. The actual story is more like “the trusts will pay roughly $4 billion in capital gains tax instead of $8 billion in estate tax, a net savings of $4 billion.” That’s still a lot of money. It’s also half the headline.

Nvidia under Jensen has created roughly 27,000 employee millionaires.

A June 2025 survey of more than 3,000 Nvidia employees found that 76-78% of them are now millionaires. Roughly 50% are worth more than $25 million. One in three is worth more than $20 million.

Across Nvidia’s roughly 36,000 employees, that extrapolates to about 27,000 millionaires walking around the company right now, plus thousands more former employees who held shares and have moved on.

Jensen said it himself on the All-In podcast in July 2025: “I’ve created more billionaires on my management team than any CEO in the world. They’re doing just fine. Don’t feel sad for anybody at my layer.”

In June 2026, Jensen was in Taipei on his way to Korea. He was asked about a big standoff Samsung had with its union, before ultimately agreeing to pay worker bonuses given all the DRAM demand and growth. He said, I’m not an expert, but I think people should be paid as much as possible. Ask my employees. Literally, I do that. I pay my employees as much as I can.”

Where did all that wealth come from?

It came from Nvidia’s stock compensation. RSUs (restricted stock units) granted to employees, vested over time, and taxed as ordinary income at vest. Same as Jensen’s. Same as your future paycheck, if you build the right career.

Nvidia files these numbers with the SEC. They are public. Here’s what the 10-K says about the total fair value of RSUs and PSUs vested for Nvidia employees in the last three fiscal years:

• Fiscal 2024: $8.2 billion in employee equity vested

• Fiscal 2025: $15.1 billion vested

• Fiscal 2026: $22.2 billion vested

• Three-year total: $45.5 billion in ordinary income paid to Nvidia employees through RSU vesting

Every single dollar of that $45.5 billion was taxed as ordinary income at the moment it vested. Most of those employees live in California. So apply the same blended effective rate (federal + state + Medicare) of roughly 45% to be conservative.

$45.5 billion × 45% is approximately $20.5 billion in federal and state income tax paid by Nvidia employees in the last three fiscal years from RSU vests alone.

That doesn’t include:

• Capital gains tax on the appreciation of shares they held past vest and later sold

• Property tax on the Bay Area houses they bought

• Sales tax on every dollar they spent

• The corporate income tax Nvidia itself pays

• Payroll taxes (Social Security, Medicare, unemployment) on $30B+ in annual wages

Nvidia the company also pays a lot of taxes.

Nvidia’s own corporate income tax bill (in the 10-K, on the income statement) was $4.1 billion in fiscal 2024 and $11.1 billion in fiscal 2025. Fiscal 2026 is even higher.

Three years of Nvidia corporate income tax: approximately $25+ billion.

Let’s add the conservative numbers, just from the last 2-3 years:

• Jensen’s personal income tax on his own CEO comp: ~$42M

• Jensen’s capital gains tax on $2.9B of stock sales: ~$1.07B

• Nvidia employee income tax from $45.5B in RSU vests: ~$20.5B

• Nvidia corporate income tax: ~$25B+

Total, conservatively: roughly $46-50 billion in taxes paid to federal and state governments by Jensen, his employees, and his company in the last 2-3 years alone.

The NYT headline says $8 billion in estate taxes will be avoided when Jensen dies in some unknown future year.

The reality is that Jensen, his employees, and his company are sending the U.S. and California governments somewhere around $15-25 billion a year, every year, while he’s alive.

Said differently: the “tax dodger” headline talks about a one-time estate event decades from now. The tax engine he built today is bigger than that every year.

How This Applies To You.

Your worldview massively shapes the decisions in your life.

Make sure your worldview is real and based on facts.

Pretty please with whiskey on top.

The story that says billionaires pay no taxes is false.

The story that says AI is destroying radiology jobs is false.

The story that says you can’t build something real because the system is rigged against you is the most expensive false story of them all.

Beliefs are expensive because they are self-fulfilling prophecies.

If you choose to believe in scarcity, it will be true. If you choose to believe in abundance, it will be true.

What you believe determines your future.

Why not tap into a different lens that says there has never been a better time to be alive?

Jensen was once a 16-year-old who didn’t know what the future had in store for him.

But he took a chance and went to college early.

He took a chance to court Lori, who became his wife.

He promised her that by the age of 30, he would become a CEO.

He wasn’t born at the age of 63, as the CEO of Nvidia worth 12 figures.

He designed his future through a set of decisions he made as a teenager about your age. Decisions that were grounded in a worldview that suffering is a net positive and the future is full of abundance.

Because abundance is yummy.

Every one of those 27,000 Nvidia millionaires started as a regular person who took a job. Some of them are immigrants. Some came from regular state schools. Many did not grow up rich. They got hired, did the work, held the equity, and became category kings.

That’s available to you too.

But only if you reject the doomer story first.

The world is full of people who will tell you why it can’t be done. And even if it could be done, you could never be the person who does it. Spend no time with these people.

(Pirate Christopher took this picture in the office of a self-made, multi-billionaire, category designing entrepreneur.)

For The Aspiring Artist, Writer, Musician, Or Filmmaker

You might say, but I don’t want to go into business. I want to do something creative. And I’m scared and angry at AI.

We’ve watched AI image generation hit the art world hard.

We’ve seen AI music tools that can produce a song in 30 seconds. If you want to be an illustrator, an animator, a screenwriter, a session musician, or a graphic designer, the ground is moving under your feet and we’re not going to pretend otherwise.

The most important creators on the planet are wrestling with AI too.

They are engaging with AI on their own terms. Some of them with deep skepticism, mixed with excitement.

James Cameron is the director of Terminator 2, Titanic and Avatar. He joined the board of Stability AI in 2024. He’s spent his career warning that AI could end humanity. He still thinks AI replacing actors is “horrifying” and that human art is “sacred.”

But he wants to understand the technology from the inside. He wants to use AI to cut the cost of blockbuster VFX in half, so big films can still get made without laying off the artists who make them.

Jacob Collier is a five-time Grammy winner. He partnered with Google on an AI music tool in 2024. He calls AI a “marvelous sort of sonic soup” that he can steer in uncharted directions. He’s used it to create sounds nobody had heard before.

Björn Ulvaeus is the songwriter behind ABBA, one of the biggest pop acts of all time. He’s co-writing a musical with AI right now. He says working with AI is “like having another songwriter in the room with a huge reference frame.” He also says AI is “lousy at making a whole song” and “not good at writing lyrics.”

Grimes has officially opened her voice for AI music collaboration.

Holly Herndon built a public “AI voice twin” she calls Holly+.

Wyclef Jean used Google’s Lyria 3 to help develop his song “Back From Abu Dhabi.”

None of these artists are saying AI is great. Several of them are saying parts of it are alarming. What they’re all doing is engaging with it on their own terms instead of letting other people use it on theirs.

If you want to be a filmmaker, you can be the filmmaker who learns to direct AI like Cameron. Or you can be the filmmaker who got replaced by someone who did.

And maybe, because of you and AI, we will have 1,000 times more art than we have now.

Art that both wounds and inspires us. Music that moves us to action to make the world better. Movies that bring an abundance of beauty to soothe us when the world leaves us with open sores.

Maybe, because of you, the phrase ‘starving artist’ will become an oxymoron.

Van Gogh died penniless, but his art is worth hundreds of millions a century later. Billie Holiday died with $0.70 to her name, despite being one of the great Jazz vocalists. Orson Welles created Citizen Kane, but never directed a profitable movie in his lifetime.

What if this next generation of artists, powered by AI, shrinks the cost to create and smashes the timeline for the artist to be fully appreciated so they can see and enjoy the fruits of their labor?

The choice to believe in abundance or scarcity is yours.

And whatever you choose to believe, it will come true.

Now, let’s get to the 18 ideas.

18 Crazy Profitable AI Businesses You Can Build Before 18

A few years ago we wrote a mini-book called How To Build Your First (Crazy Profitable) Business As A Teenager.

It became one of our most popular pieces of writing ever.

The argument was simple: Native Digital teenagers had an unfair advantage over Native Analog adults, because they understood the digital world in ways their parents, teachers, and bosses did not. If a teen would stop treating their phone like a TV and start treating it like a workshop, they could build a profitable digital business by 18, sock away $30K, and let the time value of money do the rest.

That advice still works. We still believe every word of it.

And there is even more proof it works. About 42% of U.S. teens under 18 earn something online. But that bar is low. Selling one hoodie on Depop counts. But still. Selling one thing once, counts as an entrepreneurial act. About 5% are running something that looks like an actual business.

Most importantly (for the first time in 25 years of tracking) 18–24 year olds are now starting businesses at higher rates than any other age group. Babson College called it a pattern “not seen in recent GEM USA report history.”

Here’s the part that’s genuinely, historically different: every generation before this one had to wait. Wait to be old enough. Wait for capital. Wait for permission.

This generation doesn’t wait. They got an AI co-founder.

In 2022, “Native Digital” meant you knew how to use Instagram, TikTok, Shopify, and YouTube. In 2026, that’s table stakes. The new advantage is being able to vibe create with AI, train your own agents, and ship outcomes ten times faster than the adults around you who are still asking, “Wait, what’s a custom GPT again?”

Last summer Pirate Eddie’s 17 year old son Luke helped us build the Pirate Eddie Bot. By the time he was done, we had an AI version of Pirate Eddie that’s available 24/7 to thousands of Founding Subscribers.

That bot is now one of the biggest drivers of our business.

(Built by a “kid”.)

That’s the opportunity in front of every teen reading this. Not “use AI to do homework faster.” Build a business with AI as your co-founder. Stack $30,000 by the end of one summer. And graduate high school with skills your peers (and most adults) won’t have for years.

This is the sequel to the OG mini-book.

One last word of caution.

Too many young folks are using AI as shortcuts. They end up creating AI slop. And it is obvious.

Using AI to cheat makes you a donkey. You want to use AI as a rocketship.

There are your peers who use AI to fake their way through homework, assignments, and life. They paste a prompt into ChatGPT, copy the output, and turn it in. Their writing is bland. Their thinking is borrowed. They’re just generating low-value output that anyone with a free OpenAI account could generate.

As AI gets cheaper and faster (it will), they’re going to discover their “skills” have zero market value.

Great writers become greater with AI. Lazy writers become lazier with AI.

AI works like money, it doesn’t change people, but it does reveal and amplifies who they are.

You want to learn to use AI as a co-founder. Not as a cheat code. Not as a threat.

As a partner. To do legendary stuff. And create legendary things. And when you do, you’ll have what the Doomers think is impossible and what the Slop Teens think they already have: a real, durable skill that pays you $30,000 by the end of a summer.

Don’t believe us yet?

Let’s get to the math.

$30K In Your First AI Summer

In the OG mini-book, Pirate Eddie ran the numbers on $30K by 18.

If you invest $30,000 in the Vanguard S&P 500 Index Fund by age 18, assuming 10% historical returns, you’ll have a little over $2,600,000 by the time you retire at age 65.

If you invest in Category Queens like Microsoft or Apple and average 25% annual returns, you’ll have over one billion dollars by retirement.

That math hasn’t changed.

What’s changed is the timeline to get there.

In 2022, hitting $30K as a teen meant: 10 clients × $3,000 each across a year. Or 100 products at $300. Or 300 products at $100. Real, doable, but a year-long project for most teens.

In 2026, hitting $30K as a teen means: one AI summer.

Here’s the math:

• 10 weeks of summer

• $3,000 per week target

• = $30,000

That’s one Delphi bot serving 100 customers at $30/month. Or three local businesses paying you $1,000/month each for AI automation. The math gets easier every month because AI tools get more powerful every month.

$30K by 18 is the OG promise. $30K in one summer is the AI version.

Now here are the 18 ways.

We’ve organized them into three buckets:

• Save Time ideas, where the buyer is an adult who’s drowning in work

• Save Money ideas, where the buyer avoids overpaying for something they need

• Make Money ideas, where you build an asset that pays you back

Pick one. Don’t read them all and try to do them all. Pick the one that fits your existing interests, skills, or relationships. Get one customer. Then get five. Then come back for the next.

SAVE TIME

The buyer is an adult who is drowning. You’re selling them their life back.

Read more

Welcome to the Pirate Street Journal. The business press covers companies. We cover categories. Each week, we pick three headlines worth paying attention to and break down the category underneath. Read the news through a different lens.

Dear Friend, Subscriber, and Category Pirate,

The University of Michigan consumer sentiment index just came in at 44.8.

The lowest reading in the history of the survey.

April was already the worst on record. We beat it, then beat it again a month later.

Near-zero unemployment. Record-high stock market. GDP growing. Entrepreneurship at an all-time high.

And the consumer says this is the worst they can remember.

Something doesn’t add up.

Here’s what we covered in this episode:

1. “Record low” is good news.

The consumer isn’t behaving like the survey says.

Nobody’s broke and curling up in a ball.

They’re getting smart. Waiting longer to buy a car. Buying less packaged food. Trading stuff for experiences.

Because the real issue is not the consumer ‘income statement’. The real issue is the consumer ‘balance sheet’ is bloated and designed for a nuclear family that is declining.

• Single family homes that are too expensive and too much space for single people.

• Big cars sold for families that aren’t being formed.

• Groceries to cook in a DoorDash world.

The old linear life script is dissolving. Get married, get the house, get the promotion, collect your Scooby Snacks of purpose along the way. When that script breaks, people go find meaning on their own terms.

2. The synthetic customer, and the race to beige.

Bain published “Synthetic Customers Earn Their Stripes.” AI-generated buyers, backtested against a real conjoint study, replicated about 90% of the outcomes. Which features drive choice. Which products to launch. Even early price sensitivity. Target and US Bank are already testing on synthetic audiences before anything ships.

The technology is a huge unlock.

Sadly most companies will use it the wrong way.

Everybody builds one. Everybody aims it at the fat part of the bell curve. They optimize the average customer into the ground and call it insight.

Synthetic customers trained on average consumers makes us all dumber.

We have an opposite POV…check it out.

3. The triple wasn’t good enough.

The QQQ is up around 600% over ten years, roughly 21% a year. The S&P did 13 to 14%. To get rich, you just had to sit still.

Gen Z isn’t sitting still. A third have played prediction markets, a third hold crypto, and a quarter of their portfolios sit in non-traditional assets. The punchline: roughly 69% of Polymarket accounts have lost money since 2022.

The FOMO flipped. A triple every year for a decade, and a whole generation said, not good enough, I want the fences.

Why swing that hard? 9/11, then 2008, then COVID, each one before they could legally drink. When every safety net detonates that early, “wait 40 years” sounds naive.

What’s coming up on Pirate Street Journal

Three weeks a month, we drop the video. Three topics, thirty minutes, one cowbell.

Once a month, we publish a written deep dive, the kind of category analysis you cannot get anywhere else. That one is for paying subscribers only, monthly and founding.

Next week, we’ll be publishing a deep dive.

Two ways to climb aboard now:

Monthly subscriber: $20/month. You’ve done dumber things with $20.

Founding subscriber: $375/year. For about a dollar a day, you get every mini-book we’ve ever written (300+), every audiobook (30+), digital copies of all seven of our Big Books, and unlimited access to The Pirate Eddie Bot and Pirate Christopher Bot, your 24/7 AI jamming partners for category building.

Subscribe today, get the next deep dive the day it drops, and start jamming with the bots.

Subscribe now

Recorded Friday, May 29. Every number above is as of that morning.

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

Stay tuned for next week’s episode.

Hey Ho, Let’s Go!

Arrrrrrr,

Category Pirates

Eddie Yoon

Christopher Lochhead

Dear Friend, Subscriber, and Category Pirate,

Jennifer Hall Thornton has a PhD and a law degree. Her kids’ friends call her Dr. Doctor.

She ran the everything-but-sales side of a digital company while raising two kids thirteen months apart, with an elderly mother nearby and a husband who lived on a plane. She was in the first Academy cohort, before anyone could tell her the timing was right. She told them the timing was right.

She is also an Agentic Mom.

Jennifer built a set of Claude skills that logs into her kids’ college Canvas, checks for anything new, downloads it, summarizes it, emails them, and then builds practice quizzes from the material. She built it for herself first. Then she shared it with her 18 and 19-year-olds.

The agentic mom is agentifying her children.

A mother who learned to delegate the donkey work of her own life to AI agents, looked at her kids drowning in logins and busywork, and decided they did not need to be good at the stuff she had to be good at to survive school.

Pirate Jennifer did not raise her kids to be the best version of her. She is consulting them into the best version of them.

Most parents try to clone themselves. They want the kid to do the thing they did, or the thing they wish they had done.

Pirate Jennifer did the opposite, and she did it before Creator Capitalist gave her the words.

She made her kids write thank-you notes. Three a year, starting in third grade, one for each year of school by graduation. Both kids wrote far more than required.

Her son’s handwriting is unreadable, and his fourth-grade teacher still messages him two years out of high school because he wrote her a note. Her daughter emailed a high school neuroscience teacher as a college freshman because something he taught her showed up on a biology midterm her professor never covered. He wrote back inside the hour.

That is relationship capital, built by a nine-year-old and ten-year-old, compounding for a decade.

The dinner table was a debate where you had to keep up no matter your age. That is intellectual capital. Showing up late, turning in sloppy work, going to office hours because you are actually curious, all of it builds reputation capital.

She taught the four capitals before her kids could spell them.

Then Creator Capitalist came out, and Jennifer read it and thought, well, duh. She had been running the flywheel the whole time. She finally had the languaging for it.

She told us that Creator Capitalist starts thirty years earlier than we thought.

We wrote Creator Capitalist for adults. Mid-career or later, people who have already built some of the four capitals and are looking for what is next.

Jennifer read it and started talking about how the frameworks were for her teenagers. In her velvet-hammer way, she told the donkeys to look again.

Creator Capitalist is for kids, too.

She is right. The four capitals are a flywheel, the same compounding engine that Christopher teaches young people about money. Except it starts spinning at 19 instead of 50.

Tell a 19-year-old they have no intellectual capital, and they will believe you.

Pirate Jennifer calls BS.

Intellectual capital is not the diploma. It is how you approach a problem, and what your friends come to you for.

Her son is a poli-sci major who taught himself to run every machine in the engineering lab, became the TA for a course only engineering students are allowed to teach, and got paid for it. He applied to twelve colleges and got into twelve, with no sports and no titles, because he was different and had a story to tell.

That is a Creator Capitalist, two years out of high school.

Her daughter Emily is studying biochemistry at UT Austin. She loads every note and slide into a Claude project and has Claude teach her, write quizzes, grade them, then build new quizzes targeting only what she is getting wrong.

Before her last exam she asked Claude for the hardest questions it could write. When the professor found one Claude missed, she fed it back and told Claude it blew it.

She is co-creating her education with AI, then taking it back into the traditional system and winning. Her friends say it is too complicated.

They are going to regret it.

Here’s how to navigate this conversation:

• 06:01 – Parenting in the age of AI: Pirate Christopher opens by asking what it is actually like to raise an 18 and 19-year-old right now, and why Jennifer is a far better parent to young adults than she was to little kids.

• 11:09 – The book whack: How Jennifer told Category Pirates that Creator Capitalist, the book they wrote for mid-career adults, is really a curriculum for teenagers, and why they did not see it coming.

• 11:44 – The thank-you note machine: Three notes a year starting in third grade, the fourth-grade teacher who still writes back, and relationship capital built by a nine-year-old.

• 14:34 – The poli-sci grease monkey: The son who got into all twelve colleges he applied to with no sports and no titles, then became the engineering lab TA he was technically not allowed to be.

• 22:55 – The flywheel at 19: Why the four capitals are the same compounding engine Christopher teaches kids about money, except they start spinning thirty years earlier.

• 33:07 – “I call BS”: Jennifer dismantles the myth that young people have no intellectual capital, and explains what intellectual capital actually is.

• 34:44 – The agentic mom agentifies her kids: The Claude skill that logs into Canvas, summarizes new material, and builds quizzes, and the moment Jennifer realized she should hand it to her children.

• 39:26 – AI in the classroom: Why banning AI is the wrong move, what counts as cheating versus co-creating, and the World Book Encyclopedia parallel.

• 42:01 – Teaching Claude to teach you: Emily’s biochemistry workflow, the hardest-quiz challenge, and the Feynman technique applied to an AI.

• 46:33 – Build a bot, sell it to your friends: Eddie on why a college kid should build an O-chem TA bot, charge classmates fifty bucks, and learn the material better in the process.

• 53:15 – The Dickens exercise: If 18-year-old Jennifer were starting today, loving to learn and unafraid to fail, what would she build.

• 01:04:19 – Start with relationship capital: Why young people should start the flywheel with the capital they already have, and how to find the intellectual capital you do not know you own.

We were not wrong about Creator Capitalist. Jennifer just showed us it starts earlier than we thought.

The framework does not care how old you are. It cares whether you get the flywheel spinning before everyone else does.

Jennifer did it intuitively, over fifteen years, without the words. She raised two Creator Capitalists, then spent this conversation reverse-engineering how she pulled it off.

Imagine what that compounding looks like for a kid who has the framework AND the next twenty years ahead of them, instead of behind them.

Whether you are the parent or the kid, the work starts the same way.

Get the agents running. Get the flywheel spinning. Stop doing the donkey work a machine can do, and spend the time you save building the four capitals nobody can take from you.

Arrrrrr,

Category Pirates 🏴‍☠️

Eddie Yoon

Christopher Lochhead

P.S. The fastest way to start agentifying your own life (or your kid’s).

Pirate Jennifer built her agents alone, a step or two ahead of everyone around her. You do not have to.

Become a Founding Subscriber and you get access to The Pirate Eddie Bot and the new Pirate Christopher Bot, the fastest way we know to put the four capitals to work in your life, your career, and your kids’ education, without waiting for permission from a school that still thinks AI is cheating.

→ [Become a Founding Subscriber to get access here.]

Welcome to the Pirate Street Journal. The business press covers companies. We cover categories. Each week, we pick three headlines worth paying attention to and break down the category underneath. Read the news through a different lens.

Dear Friend, Subscriber, and Category Pirate,

Anthropic is paying SpaceX $1.25 billion a month for compute.

Every month through May of 2029.

Roughly $45 billion total.

That single contract is bigger than SpaceX’s entire annual revenue today.

Software is paying hardware. Hardware is paying energy. Energy is paying space.

Is it three card monte?

Or is the pie getting massively bigger?

This should be on every business news front page this week. Instead, the headlines are about Sam Altman’s house getting attacked, Eric Schmidt getting booed off a stage, and OpenAI quietly leaking that it might file for an IPO too.

Here’s what we covered in this episode:

1. AI gets an F in marketing.

360,000 Americans are in Facebook groups organized against data centers. AI is polling less popular than ICE, less popular than Trump, less popular than politicians.

The technology being protested is curing diseases and driving much of US GDP growth.

So why are so many angry at AI?

Pirate Eddie has a theory, and it does not involve AI at all.

Marriage rates. Birth rates. Teenage drinking. Labor force participation among young men.

All down.

Life stages and zest for life as we know was crumbling before AI.

2. SpaceX is going public. The TAM is the size of the American economy.

The S-1 is pitching a $28.5 trillion total addressable market.

U.S. GDP is $32 trillion. SpaceX is asking public markets to fund a business roughly the size of the entire American economy, run by a CEO whose vesting schedule requires interplanetary colonization.

Imagine being on the dock before the Nina, Pinta and Santa Maria set sail and you were offered a chance to invest in the new world.

What was the ROI on America?

What if you had a chance to invest in Space?

But the history of IPOs is that retail investors get hurt.

The history of Elon Musk is that betting against him is also expensive.

The Pirates how category designers think about an IPO this size without losing your mind or your savings.

3. The category queen vs. the category queen.

The fastest-growing company in the history of business is not OpenAI.

It is Anthropic.

Anthropic was founded by people who left OpenAI. They are now in talks at $900 billion. Higher valuation. Higher growth. First profitable quarter ever at $11 billion in revenue.

Andrej Karpathy, founding member of OpenAI and the man who coined vibe coding, just joined Anthropic. Ross Nordeen of xAI joined Anthropic earlier this month. The defectors are recruiting the defectors.

Category Design 101 says the queen takes 76% of the economics. Everyone else shares 13%. So which one is the queen?

Pirate Christopher has a frame on the video that recasts the entire question. He thinks this is not OpenAI versus Anthropic at all.

This is the (new) Pirate Street Journal.

Every Wednesday, we pick three headlines worth paying attention to and break down the category underneath.

Three Wednesdays a month, the video is free (for now). Once a month, we drop a written deep dive for paid subscribers, the kind of category analysis you cannot get anywhere else.

Two ways to climb aboard:

• Monthly subscriber: $20/month. You’ve done dumber things with $20.

• Founding subscriber: $375/year. For about a dollar a day, you get every mini-book we’ve ever written (300+), every audiobook (30+), digital copies of all seven of our Big Books, and unlimited access to The Pirate Eddie Bot and Pirate Christopher Bot, your 24/7 AI jamming partners for category building.

To never miss a deep dive, become a subscriber today.

Subscribe now

What’s coming up on Pirate Street Journal

A few of the threads from this week’s episode are running headlong into a much bigger story, which is the IPO season that is about to define the next decade of public markets.

On June 10th, two days before SpaceX is estimated to start trading, we are publishing the next PSJ written deep dive. We will be working through how a category designer thinks about investing in an IPO of this scale, what the category math says about SpaceX, OpenAI, and Anthropic going public in the same window, and we don’t know what the headlines will do between now and then, so there will be more.

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

Stay tuned for next week’s episode!

Hey Ho, Let’s Go!

Arrrrrrr,

Category Pirates

Eddie Yoon

Christopher Lochhead

P.S. - Founding subscribers get every mini-book we have ever written (300+), every audiobook (30+), digital copies of all seven Big Books, and unlimited access to The Pirate Eddie Bot and Pirate Christopher Bot, your 24/7 AI jamming partners for category building for about a dollar a day. You have done dumber things with a dollar a day.

👉 Become a founding subscriber.

Welcome to the Pirate Street Journal. The business press covers companies. We cover categories. Each week, we pick three headlines worth paying attention to and break down the category underneath. Read the news through a different lens.

Dear Friend, Subscriber, and Category Pirate,

Last week, we recorded the very first episode of the Pirate Street Journal.

The Pirate Street Journal is for leaders with a different mind.

A different take on business news.

Through the category lens.

Our mini-books are timeless. PSJs are timely.

Our mini-books are long stories longer. PSJs have 30-minute seat belts.

Our mini-books are thinker’s high. PSJs try to help you think before you act.

But, but, but, but…

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

Think of this like professional wrestling. It’s entertainment.

Don’t be so smart, you’re stupid and suplex your safety net savings.

Hey Ho, Let’s Go!

PSJ is the new weekly thing. The video’s free. The deep-dive written analysis is paywalled. Watching makes you informed. Reading makes you different.

Two ways to climb aboard:

• Monthly subscriber: $20/month. You’ve done dumber things with $20.

• Founding subscriber: $375/year. For about a dollar a day, you get every mini-book we’ve ever written (300+), every audiobook (30+), digital copies of all seven of our Big Books, and unlimited access to The Pirate Eddie Bot and Pirate Christopher Bot, your 24/7 AI jamming partners for category building.

To read this week’s deep dive, become a subscriber today.

Subscribe now

1. Why is Salesforce down? Why is Micron up?

Read more

Arrrrr! 🏴‍☠️ Welcome to a Free Post 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, The Pirate Eddie Bot and Pirate Christopher bot, copies of our 7 Big Books, and 30+ audiobooks. If you’re not a founding subscriber, hop aboard!

Subscribe now

Dear Friend, Subscriber, and Category Pirate,

Here’s a fun thought experiment.

Open your favorite AI tool right now and ask it to do your job. Write the email. Build the deck. Summarize the report. Draft the proposal. It’ll do a pretty good version of all of it. In some cases, a better one than you would have produced on a Tuesday afternoon when you were tired.

Now ask it to build you 200 people who trust you, buy from you, refer you, and show up for you when it counts.

It can’t. It never will.

We had this conversation in the Academy last week. Pirate Christopher explained how a thought leader actually builds trust, and the answer was simple enough to fit on a sticky note: Be a trustworthy person. Say what you mean. Do what you say. And then Pirate Christopher dropped this bar:

“Who you are speaks so loudly, I can’t hear what you’re saying.”

That’s the part AI cannot touch.

A model can mimic your tone. It can copy your formatting. It cannot show up for someone on a Tuesday for three years running. It cannot keep a promise. It cannot, as Gina Bianchini puts it, create people magic: the thing that happens when humans gather around a shared point of view and discover they were never alone in their thinking.

People magic is the asset AI can’t steal. Community is where you store it. Category design is how you build the gravity that pulls people into it in the first place.

And the Four Capitals from Creator Capitalist are what compound inside it.

• Intellectual capital gives you something worth gathering around.

• Reputation capital is what gets built when you keep showing up the way Pirate Christopher described.

• Relationship capital is the deep, durable trust that turns an audience into a community.

• Financial capital is what all four make possible, the freedom to fund experiences your knowledge worker self has never let you dream about.

AI can speed up the first one. It cannot manufacture the other three.

Which is exactly what we’re getting into next Wednesday with one of our favorite Creator Capitalists on the planet: Gina Bianchini, CEO of Mighty Networks, the platform whose Hosts generated over $500M in 2025.

Pirate Gina, Pirate Eddie, and Pirate Christopher are running a free live event called “The Asset AI Can’t Steal” on Wednesday, May 27 at 11 AM PT.

We’ll get into:

• Why community is the one piece of your business AI cannot compete with

• How to find your superpower and build a category around it

• How the Four Capitals from Creator Capitalist compound when you’ve got a real community attached to your work

👉 Grab your free seat here.

Arrrrrrr,

Category Pirates

Eddie Yoon

Christopher Lochhead

Subscribe now

Dear Friend, Subscriber, and Category Pirate,

“Bet on yourself sooner” is the most popular piece of career advice on the internet.

But no one tells you how.

Good news. Linda’s story lays the practical and tactical out clearly.

Most people hear it and do the obvious thing.

They bet harder on the most visible capital they already have. They chase a bigger title (Reputation Capital). A bigger paycheck (Financial Capital).

Then they wonder why nothing compounds.

Linda Deeken did the opposite for twenty years.

And it’s the reason she can run her own thing now with more leverage than most of the partners who once outranked her. Five kids. Two sets of twins. A daughter with Down syndrome who also beat cancer. A husband with his own career. A solo consulting practice (Deeken Strategies) with agency and economics most W2 partners long for. A returning client roster that calls her because she “makes them better.”

She built all of that by quietly betting on the two non-obvious capitals first.

Relationship Capital and Intellectual Capital come first.

Relationship capital and intellectual capital compound silently.

Linda spent twenty years building these two capitals first. By the time she launched Deeken Strategies, the math was lopsided in her favor. The reputation and the financial returns came roaring in because the other two had been compounding the whole time.

Four moves that looked like sidesteps and were actually compounding.

Linda turned down Stanford for UW Madison at 17. Her father was older, her mother had her at 43, and Madison just made more sense for her family. She traded the diploma everyone in her future networking room would have recognized for time with people who would not be around forever.

How many of us would make that choice?

1 out of 100? 1 out of 1,000? Maybe even less.

She left Mercer for The Cambridge Group. Mercer had the bigger brand. Cambridge was 50% female partners who were working moms, the better operating model, and the path that would actually let her become both a serious consultant and a mother. Reputation down. Relationship and intellectual capital up.

She went to Miller Brewing Company for a year, had her first set of twins, then came back to Cambridge as a CMO, not a partner. Title down. Writing muscle up. The CMO role forced her to develop her own point of view instead of executing other people’s frameworks. That’s the season most consultants never get. It’s also the season that built the intellectual capital she now monetizes on her own.

She launched Deeken Strategies before she had the permission slip she wanted. By her own admission, that was the bet she wishes she had made sooner. She could only make it because the first three bets had already loaded the dice.

Her superpower is the outcome other people get when they work with her.

The way Category Pirates defines a superpower is different from how most people do it. Most people would say a superpower is what you’re good at. We say a superpower is the outcome you produce for others that you are best known for.

Linda’s clients describe her in three words: smart, humble, focused on your outcomes.

That combination is rare on its own.

It’s rarer still in someone running a household of seven. And it’s the languaging she earned by writing, by refining her POV through the CMO season, and by treating every client engagement like a long-term relationship instead of a short-term transaction.

She runs her household the same way she runs her client work. She has a SWOT analysis for each of her five kids. Strengths, weaknesses, opportunities, threats. She is not parenting her kids to become the best version of her. She is consulting them into the best version of them.

This is what integration actually looks like. The work feeds the parenting, the parenting feeds the work, and both halves get sharper because the same operating system is running underneath both.

Here’s how to navigate this conversation:

• 05:17 – Turning down Stanford at 17: The first time Linda chose relationship capital over reputation capital, and why she never built her identity around the diploma she didn’t get.

• 12:23 – Chemical engineering as a consulting prep school: Why studying the hardest thing makes the easier things easier, and why “learning the lingo” is the first move in building intellectual capital.

• 18:55 – Leaving Mercer for Cambridge: Trading the bigger brand for the operating model that would actually let her become both a serious consultant and a mother.

• 25:12 – The Miller detour: One year in corporate, a set of twins, a move to Milwaukee, and what she learned about herself in a job she didn’t love.

• 26:35 – The CMO role she designed: How Linda built a returning role at Cambridge that gave her flexibility AND forced her to develop a POV instead of executing other people’s frameworks.

• 29:08 – “Put me in coach”: The moment the CMO role stopped being enough and Linda launched Deeken Strategies.

• 45:53 – Smart, humble, oriented to your outcomes: The three-part combination that became Linda’s superpower and the languaging her clients use to refer her.

• 49:38 – Children as consulting projects: The SWOT-per-kid framework, why she rejects the “I want my kid to do what I never did” trap, and what Sarah is teaching the whole family.

• 1:04:19 – Own your own future, fearlessly: Linda’s closing convict to every woman watching from the sidelines.

What Linda is doing is not a one-off.

It’s a pattern.

The same pattern Creator Capitalist documents end-to-end. Bet on relationship and intellectual capital first. Develop your point of view. Find the work that builds your four capitals at the same time. And then, when you can’t bear NOT to bet on yourself any longer, bet.

She did it intuitively, over twenty years, without the framework. Imagine what that compounding looks like when you have the framework AND the twenty years ahead of you instead of behind you.

Connect with Linda:

• Follow her on LinkedIn here

Arrrrrr,

Category Pirates 🏴‍☠️

Eddie Yoon

Christopher Lochhead

P.S. The fastest way to figure out which capital you’re under-betting on.

Linda did this work over twenty years, mostly alone, by writing in the margins and pressure-testing her own thinking against clients who became friends. You don’t have to.

Become a Founding Subscriber, and you’ll get access to The Pirate Eddie Bot and the new Pirate Christopher Bot. They will challenge your premise, sharpen your POV, and stop you from doing what most people do when they say they’re betting on themselves, which is just betting harder on the capital they already have plenty of.

→ Become a Founding Subscriber to get access here.