The race to Wall Street between the two biggest AI labs is becoming a race against the clock — and Anthropic is sprinting while OpenAI walks.
According to reporting from the Motley Fool and Reuters, Anthropic could begin marketing its initial public offering as early as the week of November 9, with trading potentially starting before Thanksgiving. The targeted valuation approaches $2 trillion, which would make it the largest IPO in history, clearing the bar set by SpaceX's June 2026 listing at roughly $1.78 trillion.
OpenAI, meanwhile, is firmly in the other lane. CEO Sam Altman has ruled out a 2026 IPO, saying the company will prioritize AI safety and will not list until 2027 at the earliest. Instead of going public, OpenAI is pursuing private funding — Bloomberg reported in late September that the company is discussing a $30 billion-plus bridge round at around a $1.4 trillion valuation.
The numbers behind Anthropic's filing explain the urgency. Reuters' account of the company's draft prospectus shows 2025 revenue of about $4.6 billion against an operating loss of roughly $8 billion — and a headline net loss near $42 billion, most of it a non-cash accounting charge tied to financing instruments that could convert into shares. The operating picture is improving fast: market commentary has cited second-quarter 2026 revenue above $11.5 billion, though those figures have not been confirmed in a public filing.
The real story is on the liability side. Anthropic has disclosed roughly $518 billion in multiyear cloud and infrastructure commitments — including $111 billion with Google, $110 billion with Amazon, and $31 billion with Microsoft. A hoped-for $100 billion IPO raise would cover barely 19 percent of that total, and about 80 percent of the obligations are noncancelable. Broadcom may separately lend Anthropic up to $42 billion for data-center infrastructure, but even that covers only a fraction of the bill.
There is concentration risk, too. Nearly a quarter of Anthropic's 2025 revenue reportedly came from just two large customers — publicly unidentified, and with no guaranteed renewals.
OpenAI's balance sheet tells a different story. The company closed a $122 billion round at an $852 billion valuation in March, and its annualized revenue run rate is approaching $70 billion. But its cash needs are staggering: the Financial Times has cited an internal presentation projecting cumulative negative free cash flow of $278 billion from 2026 through 2030.
Taken together, the two paths look like a study in contrasts: Anthropic opening its books to public investors to fund a compute bill it cannot shrink, OpenAI staying private while it burns through private capital. The gap between their listings could exceed a year — if OpenAI stays private past next November. For anyone watching AI's economics, the next few weeks will be the most instructive in the industry's history.