I have seen a lot catchy headlines about Anthropic S-1 so I figured I would actually sit down and go through it. As someone who has been interested in the whole idea of an AI bubble, I wanted to see if there were going to be parallels between dotcom companies and Anthropic:
The answer was Yes and No.
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Anthropic just opened its books. Here's what's inside, and why it rhymes with 2000.
Yesterday the maker of Claude filed to go public. Strip away the hype and here's what you need to know.
THE QUICK BREAKDOWN
• It plans to list on the Nasdaq under the ticker "ANT" (kind of hilarious ticker I dont know why)
• Revenue is exploding. It went from $41 million in 2023 to $4.59 billion in 2025 and $16.29 billion in the first half of 2026 alone.
• The headline loss is scary. Anthropic recorded a net loss of $80.7 billion for the six months through June 2026, but $72.4 billion of that was an accounting charge for the rising value of its convertible notes. (Graphic 2)
• The real pressure point is compute. The company has committed to spending between $542 billion and $567 billion on future compute and infrastructure.
• Buyers get the money but not the steering wheel. A trust elects four of seven directors, and a single share held by the co founders' LLC casts a fixed 50.1% of every general vote.
WHAT ANTHROPIC ACTUALLY DID WITH AMAZON'S NOTES
Starting in 2023, Amazon gave Anthropic money in the form of convertible notes. Think of a convertible note as a loan with a twist: instead of getting paid back in cash, the lender can swap the loan for shares at a price locked in on day one.
Amazon's price was locked in very low. The prospectus shows about $6.2 billion of principal that converts into 1.84 billion shares at fixed prices of roughly $2.09 and $5.05. Since then, Anthropic's last private round priced shares near $59. So the same $6.2 billion IOU is now carried at $108.6 billion. When the company goes public, those notes turn into shares for Amazon, up to Amazon's 12% ownership cap, with the rest rolling into new notes.
Accounting rules make Anthropic record that jump in value as a loss. That's why the first half of 2026 shows such a huge number: $72.4 billion of the loss came from the notes becoming far more valuable than when they were issued. No cash left the building. Amazon simply got a slice of the company that is now worth about 17 times what it paid. (Graphic 1)
Here's the part that matters. Amazon isn't just an investor. It's also one of Anthropic's biggest suppliers, with a $110 billion compute deal running from May 2026 to April 2036. And it's a sales channel too, since about 48% of first half 2026 revenue came through the AWS, Google Cloud and Azure marketplaces.
Google got a similar sweetener. In March and April 2026, alongside their compute agreements, Google and Amazon agreed to buy preferred shares at $259.14, while the next round priced at $589.01 just weeks later. Anthropic booked a net $9.4 billion loss on the gap.
WHY THAT RHYMES WITH 2000
In the dotcom days, startups regularly handed their big partners a piece of the company instead of, or on top of, cash. When drkoop signed its $89 million deal with AOL, AOL also received fully vested and performance based warrants to buy drkoop shares. Later, drkoop's cash payments were converted into stock, giving AOL a 10% stake. The partner selling the service also owned a chunk of the customer.
The telecom giants ran the same idea from the other direction. Lucent, Nortel and Cisco lent money to young carriers so those carriers could buy Lucent, Nortel and Cisco equipment. The supplier funded the customer, and the customer's spending came right back as the supplier's sales.
Anthropic's setup has both flavors at once. Its biggest suppliers own a growing piece of it through cheap notes and discounted shares, and those same suppliers collect the compute bills and sell its product. That's the loop: money and ownership flowing out to a partner, and spending flowing back to that same partner.
THE HONEST DIFFERENCE
Amazon put in real cash, and Anthropic's revenue comes from real customers. Most dotcoms handed out stock because they didn't have cash, and Homestore went further and faked its sales. Nothing in this filing shows that. The risk here isn't fake numbers. It's that Anthropic's investors, landlords and cash registers are the same few companies, and in 2000 that kind of tangle held up right until one link broke.
HOW THE DOTCOM CROWD DID IT
AOL and drkoop. The health site went public in 1999 and almost immediately signed a deal to pay AOL $89 million over four years, with AOL also getting warrants to buy drkoop shares. When the cash ran dry, the payments were converted into stock, giving AOL a 10% ownership stake. The ending: bankruptcy in December 2001, with its assets sold for just $186,000.
AOL and Homestore. This one was a loop. Homestore paid inflated sums to vendors, the vendors used that money to buy ads from media companies, and the media companies then bought ads from Homestore. Regulators summed it up simply: Homestore recycled its own money to generate revenues. Ad revenue was overstated by $46 million, or 64 percent, for the first three quarters of 2001. AOL didn't walk away clean either: the SEC later brought civil charges against four former AOL executives over $1.26 billion in restated earnings.
Lucent, Nortel and Cisco. The equipment makers lent money to shaky startups so the startups could buy their gear. Alcatel, Cisco, Nortel and Lucent committed about $1.5 billion, $2.5 billion, $2.1 billion and $7 billion respectively. When the carriers started dropping, Winstar's bankruptcy exposed that vendors had routinely financed deals for the shakiest startup carriers. The loan and the "sale" died together. (Graphic 3)
THE 2026 VERSION
Look at who sits on every side of Anthropic's table.
• Amazon is the lender. Amazon is also a supplier, with a $110 billion compute deal running from May 2026 to April 2036.
• The cloud giants are also the store. About 48% of first half 2026 revenue was sold through the AWS, Google Cloud and Azure marketplaces.
Then there's scale. Lucent's vendor loans were about a quarter of a year's revenue. Anthropic's compute promises are about eight years of current revenue. (Graphic 4) Those are different kinds of promises, but the direction should make you pause. And the company itself warns that customers can often reduce usage or terminate with limited or no notice, while the compute bills keep coming.
Independent finance reporter Jack Gamble of Nobody Special has been hammering the hardware side of this. His take: the hardware, not AI itself, is the bubble, and the debt market is starting to flinch, with CoreWeave's bonds trading around 80 cents on the dollar.
WHERE THE COMPARISON BREAKS
Fair is fair. drkoop had almost no revenue. Homestore faked its sales. Nothing in this filing shows fake revenue. Anthropic says it has more than 11,900 customers above $100,000 in trailing revenue, it posted its first operating profit, $974 million, in the second quarter, and it held $131.7 billion of cash and short term investments at June 30. Even a skeptical review notes the accounting and direct customer contracts are evidence against the claim that investor money simply returns as revenue, though the filing leaves the question open.
BOTTOM LINE
This isn't drkoop. The business is real. But the money map looks a lot like 2000: the same giants are the investor, the landlord and the cash register. In 2000 that loop held until one link snapped. If you're buying this IPO, you're betting nothing snaps.
Not financial advice. Read the filing yourself.