Anthropic IPO: 1997 Amazon Or 1999 Amazon?
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On May 15, 1997, a money-losing online bookstore went public at $18 a share. Amazon raised $54 million. The whole company was valued at about $430 million. Today it’s worth about $2.6 trillion, roughly 6,000 times more.
Anthropic’s IPO is the first since then that feels the same way: a new kind of business, growing faster than anyone can model, that people either call the future or a bubble. So let’s line them up.
| Amazon at IPO (1997) | Anthropic at IPO (2026) | |
|---|---|---|
| Revenue, last year | $15.7M (1996) | $4.59B (2025) |
| Revenue growth | +838% (1997) | +1,300% (first half 2026) |
| Profit | Lost $5.8M (1996) | First operating profit, Q2 2026 |
| Value at IPO | about $0.43B | $1.5T–$2T (press estimates) |
| Value ÷ trailing revenue | about 27x | about 76x–101x |
Same speed. 3,500 to 4,700 times the starting price.
Anthropic is growing as fast as Amazon did, from a revenue base about 300 times bigger. That is astonishing. But Amazon’s buyers didn’t get 3,000x because Amazon grew fast. They got it because they bought it small.
See more lines: what happened next at Amazon
| Year | Amazon revenue | What the stock did |
|---|---|---|
| 1997 | $148M | IPO at $18 in May |
| 1999 | $1.64B | Peaked in December, worth about $37B |
| 2000 | $2.76B | Fell all year |
| 2001 | $3.12B | Bottomed in September, 94% below the peak |
| 2009 | $24.5B | Finally back above the 1999 peak |
Amazon value at IPO: $18 × about 23.9M shares outstanding after the offering (1997 prospectus). 27x = $430M ÷ $15.7M. Anthropic: trailing revenue $19.7B (H2 2025 + H1 2026); 76x–101x = $1.5T–$2T ÷ $19.7B. 3,500x–4,700x = $1.5T–$2T ÷ $0.43B.
The Business Is 1997
On the business, the match is close, and Anthropic wins it. Amazon in 1997 sold books at a loss and asked investors to trust that scale would pay later. Anthropic sells to businesses that pay for what they use: more than 1,900 customers spend over $1 million a year, and it turned an operating profit in the second quarter. Amazon didn’t post a full-year profit until 2003.
And it’s early. In 1997, about one in five Americans used the internet. Most companies today are still testing AI, not running on it. If you think AI is to office work what the internet was to shopping, this is 1997.
The Price Is 1999
Now the price. At its IPO, Amazon cost about 27 times its trailing revenue. Even at the very top in December 1999, the market paid about 22 times Amazon’s revenue that year. The most expensive giant of the bubble, Cisco, peaked in March 2000 at about 29 times its revenue.
Anthropic at $1.5 to $2 trillion would cost 76 to 101 times its trailing revenue. Give it full credit for its latest quarter, $46 billion a year, and it’s still 32 to 43 times. That’s more than Cisco at the top of the bubble.
The fair defense: Cisco grew about 55% a year then. Anthropic grew 14-fold. A multiple that looks crazy for one can be cheap for the other, if the growth lasts. That’s the whole bet.
What 1999 Did To The Winners
Here’s the part of the Amazon story that rarely gets told. The business never stopped growing. Revenue rose from $1.6 billion in 1999 to $3.1 billion in 2001. The stock fell 94% anyway. It took until about 2009 to get back to its 1999 high.
Someone who bought at the IPO and held still made a fortune. Someone who bought in late 1999, into the excitement, waited a decade just to break even. Same company. Same great business. The only difference was the price they paid.
That’s the hard part of owning the future: even the right company can cut your money by 90% before it pays off. In the 2021–22 sell-off, Meta fell 77% and Nvidia 66%. For families with $1 million or more to invest, how you split money between growth and steadier holdings decides whether you can sit through a drop like that. A Trefis partner firm can help you set that split.
A 1997 business at a 1999 price. Anthropic is as early and as fast as Amazon was in 1997, and a better business. But its price is already above what the market paid for the giants at the 2000 top. History says buyers at prices like that can be right about the company and still lose for years.
None of this says Anthropic will fall 94%. It says the Amazon story is a story about price. For the Google version of the same question, see Anthropic IPO vs Google IPO. And for every big IPO since, what buyers paid and what they got, see The Big IPO Scorecard.
Buying The IPO Or Waiting?
Amazon’s best buyers weren’t the ones who bought first. They were the ones who could hold through a 94% drop. If you have $1 million or more and are weighing the Anthropic IPO against what you already own, see how much rides on one bet in a free 15-minute call with a Trefis partner firm.
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