Anthropic and OpenAI are racing to IPO before the window slams shut

THE LAST TIME two technology companies of this magnitude raced each other to the public markets, the year was 1999 and the companies were selling pet food and groceries online. The stakes are considerably higher now. Anthropic, the maker of Claude, has begun discussing an initial public offering as early as October, with bankers expecting the company to raise upward of $60 billion — a figure that would make it the second-largest IPO in history, trailing only SpaceX's anticipated $75 billion listing. Its archrival OpenAI, last valued at $730 billion, is maneuvering to beat Anthropic to the exchange, with Sam Altman reportedly telling associates he would prefer ChatGPT's parent to list first.

The financials underpinning both companies have shifted dramatically in recent months. Anthropic's annualized revenue more than doubled during the first two months of 2026, reaching $19 billion on the strength of its automated coding tools and enterprise developer platform. OpenAI, meanwhile, topped $25 billion in annualized sales last month, driven primarily by ChatGPT subscriptions and its expanding consumer footprint. Anthropic was last valued at $350 billion in a financing round completed just weeks ago; it has retained Wilson Sonsini as legal counsel for the offering, a concrete step that suggests the IPO discussion has moved well beyond the hypothetical. OpenAI, for its part, has held informal conversations with Goldman Sachs and Morgan Stanley, though with $120 billion in fresh capital nearly closed, it faces no immediate financial pressure to list.

Public offering, private ambitions

But the race to go public is not merely a contest of vanity metrics or founder egos — it is a referendum on which business model the public markets believe will define the AI era. Bankers and IPO advisers largely expect Anthropic to list first, and the reasoning is instructive: institutional investors, they reckon, favor Anthropic's enterprise-and-developer focus over OpenAI's consumer-heavy revenue mix. A company selling picks and shovels to the industry tends to inspire more confidence on a roadshow than one whose largest product is a $20-per-month chatbot subscription, however ubiquitous that chatbot may be. Anthropic has also projected a shorter path to positive free cash flow — 2028, versus OpenAI's 2030 — and a considerably smaller cumulative cash burn to get there: roughly $22 billion compared to OpenAI's projected $200 billion-plus.