Welcome to the Pirate Street Journal, the category news the business press misses.
Each week, we pick three headlines and break down the category underneath. Live every Thursday. See the news through a different lens. Keep reading in the Deep Dive Reports.
Dear Friend, Subscriber, and Category Pirate,
We have not one, but two Pirate Street Journal releases for you this week.
This week we went a little off road. Anthropicâs S1 was too big for one topic, so we spent the whole 30 minutes on it: the good, the bad, and the ugly. Then we recorded a special segment on the first AI election.
Walk into any meeting this week, and youâll hear Anthropicâs $104 billion loss parroted as insight, then someone else saying they canât wait to buy the IPO.
If you feel like the invisible expert in the room, this weekâs drop is built to make you the visible expert in that room: a full S1 episode (the good, the bad, and the ugly) plus a special on the first AI election.
đ´ââ ď¸ Category Pirates is on a mission to unleash 100,000 category designers into the world. To do that, weâve been building our YouTube channel, so as the donkeys say, donât forget to like and subscribe so we can reach more invisible experts destined to become Category Designers.
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Hereâs what we covered in this weekâs Pirate Street Journal:
1. The good: Anthropic just lost $104 billion. Why is its bank account still growing?
Anthropic filed to go public, and the headline number looks terrible.
The filing shows a loss of about $104 billion. About $94 billion of that is a non-cash charge on convertible notes that rose in value as the company did. Itâs mostly on paper.
Hereâs what the S1 actually shows:
Itâs growing like crazy. About $23 billion in revenue in the first nine months of this year. Same time last year: about $2.5 billion.
It has a giant pile of cash. Investors put in about $140 billion. About $132 billion is still in the bank.
It already makes cash. About $6.6 billion of operating cash flow over nine months.
Reading the $104 billion loss and stopping there is what being category blind looks like.
Remember Nvidia and Google in their fifth years? Pirate Christopher pulled the numbers. Nvidia did $29.1 million. Google did $439.5 million. Anthropic did $4.59 billion.
The category move: size the prize, then measure share of growth. Anthropicâs biggest customers spend about 0.1% of their revenue on tokens. IT budgets tend to run 4% to 5%. Thatâs a lot of room left. Anthropicâs market share went from about 40% last year to 55% this year. Our research team found OpenAI and Anthropic took 43% of venture funding this year.
So what does this mean for you?
Donât judge a fast-growing company by one scary line. Ask how big the prize is and who is taking the most of the growth.
Our mini-book, Sizing The Category Prize, shows you how to run the math on your own category (which will help you make smart investment decisions).
Hereâs the one thing to understand to be the visible expert in your next meeting:
The loss is mostly paper. The growth is real cash. In its fifth year, Anthropic made about 10 times what Google did.
2. The bad: Anthropicâs own IPO filing says what it builds might endanger humanity
The S1 lists the benefits of AI and then lists the risks: bioweapons, cyber attacks, AI going rogue, privacy, and economic disruption.
This is the first time a company has told IPO buyers its own technology could hurt humanity. Our research team found the closest example: SpaceXâs filing from the spring, which said life on one planet carries existential risk, then reframed it as SpaceX saving humanity.
So why would a company scare its own buyers?
The benefits are hard to picture. The filing says AI will speed up biology and medicine, grow the economy, spread its benefits to the world, and raise government quality.
The risks are easy to picture. The risks are easier to understand than the benefits.
Doom has been the brand. Anthropic has marketed fear from day one, and we think itâs to get regulatory capture.
Reading the risk section as news is what being category blind looks like.
Remember Oppenheimer? Every breakthrough in science (including electricity) has had the Oppenheimer effect. It is amazing, and it is scary.
So what does this mean for you?
If your pitch leads with risk, people will remember the risk. Say the benefit in words a customer could repeat at dinner.
Our Deep Dive Report, 7 ways Pirate Eddie made $10K in ten minutes, shows the personal CFO idea in real life. Pirate Eddie is now up to about $6,000 in savings, including a duplicate DocuSign account he didnât know he had.
Hereâs the one thing to understand to be the visible expert in your next meeting:
Anthropicâs numbers look great. Its words donât. Change the languaging, and the public may follow.
3. The ugly: a knifeâs edge business, and why the category might be infinite
We do not envy Anthropicâs CFO.
If Anthropic slows spending, revenue slows and the valuation drops. If it speeds up, it needs compute and power it doesnât control. The S1âs biggest fear is access to data centers, compute, and power.
Hereâs the knifeâs edge:
Spending. Pull back, and growth slows.
Power. Push forward, and you need electricity nobody has yet.
Contracts. Get the spot market versus long-term deals wrong, and the P&L flips upside down fast.
Advice for year-one IPO buyers: this will be the worst of the worst roller coasters. Donât be so smart youâre stupid.
Watching only the stock chart is what being category blind looks like.
So what does this mean for you?
Before you worry about the stock, use the category. Take one problem youâve been stuck on and give it to AI with all the facts you have.
Hereâs the one thing to understand to be the visible expert in your next meeting:
The stock will be a roller coaster. The category is intelligence, and demand for it might be infinite.
Special segment: The first AI-assisted election.
Pirate Eddie built a voting framework with Claude, and AI ran out of answers on judges and the forest preserve. Pirate Christopher ran Californiaâs props through three AIs, and Gemini wouldnât talk politics at all. And Pirate Bri, the digital native, didnât use AI to vote. Watch for the nonpartisan voting agent idea and why it takes work to get an AI to tell you the truth.
Before you go, weâd love to ask a quick favor.
Most pirates donât know PSJ is on YouTube yet. If this helped you show up sharper this week, subscribe to the channel, like both videos, and send them to one person who wants to be the smartest person in the room every Friday.
And if youâre listening to the podcast, a 5-star rating means the world to us. Itâs how we get closer to unleashing 100,000 category designers into the world. Arrrr! đ´ââ ď¸
Now see your own category
Every week, PSJ trains your eye on other peopleâs categories. The harder part is seeing your own.
Becoming a Founding member gives you all the resources to stop being the invisible expert in the room and become the visible expert. You can jam 24/7 with the Pirate Eddie and Pirate Christopher Bot, read all 7 of our big books, join the founding community, and join our live monthly jam sessions where you can ask any category design question.
Come aboard the pirate ship and stop being category blind here.
Recorded Wednesday, November 4, 2026. 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).
Arrrrrrr,
Category Pirates đ´ââ ď¸