Two of the biggest names in artificial intelligence, OpenAI and Anthropic, are moving toward public stock offerings — but a set of new headwinds is complicating the road ahead.

According to The Daily Upside, both companies are speeding toward IPOs even as regulators and observers ramp up scrutiny of "token payments." Tokens are the units of text that AI models process, and the pricing and accounting around them have drawn growing attention as the companies prepare to open their books to public investors.

The Financial Times, in a piece headlined "Why OpenAI and Anthropic may struggle to float," signals that taking these firms public may prove harder than the hype suggests. Floating — the term for listing shares on a public market — subjects a company to disclosure requirements and investor expectations that fast-growing, cash-hungry AI firms can find difficult to satisfy.

Adding to the caution, research firm Forrester has warned that OpenAI's IPO prospects, along with the question of a U.S. government stake in the company, cloud its outlook, according to IT Brief Asia. The mention of a potential U.S. stake points to the unusual degree of government involvement now shadowing the sector.

Together, the three reports sketch a picture of two AI leaders under pressure from multiple directions at once: eager to tap public markets for capital, yet facing questions about how they price their services, how they will meet the demands of public listing, and how government interest could reshape their futures.

Why it matters: OpenAI and Anthropic are among the most closely watched companies of the AI era, and how — and whether — they go public will help set the terms for investor confidence in the entire industry.