The AI Double Giants IPO Race—Anthropic Files First, Why Is OpenAI Stuck in a Dilemma?

On June 1, 2026, Anthropic secretly submitted an S-1 draft registration statement to the SEC. The earliest target IPO timing is October 2026. However, OpenAI—once seen as the biggest favorite and “the first AI IPO”—is now finding itself in a delicate bind at this moment. It has been working with bankers to prepare its listing documents, but the IPO timing may be pushed back to 2027.

Anthropic’s swift move: filing immediately after Series H funding

Anthropic’s IPO layout is nothing short of precise. Just days before filing its IPO documents, it had just completed a $65 billion Series H funding round, with a post-investment valuation of up to $965 billion—leapfrogging OpenAI’s $852 billion valuation in one move. This “file right after funding” cadence has been interpreted by the market as a clear signal: Anthropic wants this to be its final round of private fundraising, and will then go straight to the public markets.

Revenue figures are equally astonishing. As of the end of May 2026, Anthropic’s annualized revenue reached $47 billion, while the figure was only $9 billion at the end of 2025. Claude Code (its agentic programming tool) has become the fastest-growing product in the company’s history. Within 6 months of listing, its annualized revenue surpassed $1 billion, and by February 2026 it had already reached an annualized revenue level of more than $2.5 billion. Anthropic also expects to achieve positive cash flow between 2027 and 2028.

OpenAI’s valuation dilemma and internal confusion

In contrast, OpenAI’s path to an IPO looks bumpy. As early as October 2025, Reuters reported that it planned to file for an IPO in the second half of 2026, with a formal listing in 2027 and a target valuation of up to $1 trillion. But since then, there has been no substantive progress for a long time. Academic research suggests that IPOs often see “industry clustering,” and companies that go public later in the cycle often perform worse than early entrants. Even more worrying is the cautionary tale from Lyft and Uber in 2019—Lyft, which was smaller in scale, listed first but its stock performance failed to meet expectations, directly affecting Uber’s IPO performance two months later, forcing Uber to cut its target valuation.

In addition, the founder of Issuer Network pointed out: “The oxygen in the room is limited. SpaceX will absorb a large amount of capital, and the second company to go public will be in a more favorable position than the third.” If OpenAI goes public after SpaceX and Anthropic, it will face dual pressures: capital dilution and investor aesthetic fatigue.

My take: At present, Anthropic has taken the early lead in the IPO race, with an estimated 69% chance of going public. OpenAI is still as high as 72%, but the likelihood of an IPO in 2026 is decreasing. The key is which company can first prove to the market the sustainability and profitability of its AI business model.

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