OpenAI, which trails Anthropic in filing listing documents and has generated less excitement among pundits, faces several structural challenges.
These include thin margins, ongoing losses and a revenue-sharing agreement that gives Microsoft a fifth of its revenue, market watchers say.
OpenAI announced this week that it has filed its paperwork with the US Securities and Exchange Commission, saying it expected the news to leak “so we’re just announcing it”.
OpenAI says it hadn’t decided on timing yet. “It may be a while because there are things we want to do that are likely easier as a private company. But it’s a complicated set of trade-offs and this gives us the option to go public sooner if that ends up being best,” the company adds.
When and at what price
Investment research firm Zacks.com puts the ChatGPT maker’s worth at around $1 trillion, based on analyst comments. While the company hasn’t announced potential timing, this could be sometime in late 2026 or early 2027, it says, based on media reports.
Anthropic, also set to be valued at $1 trillion, is expected to list in October, according to media, with most analysts seeing it as a fundamentally better bet than OpenAI.
“The biggest debate centres on whether OpenAI will move aggressively toward a 2026 IPO, or delay until 2027 to strengthen its financial position,” says Zacks.com.
It notes that Reuters has quoted OpenAI CFO Sarah Friar as saying its financial runway needed to be stabilised before pursuing an IPO, especially given the company’s large compute obligations and infrastructure commitments.
AI research company Klover.ai says OpenAI is approaching the markets following a historic funding round that secured $122 billion in committed capital at a post-money valuation of $852 billion at the end of March.
“OpenAI’s valuation has climbed at an extraordinary pace since ChatGPT became a global phenomenon,” says Zacks.com.
The company went from about $29 billion in 2023, to roughly $300 billion by early 2025. In 2026, successive funding rounds lifted its valuation from $730 billion to $852 billion, making it one of the world’s most valuable private companies.
Numbers don’t lie
OpenAI is currently generating an average of $2 billion in revenue per month, which represents an annual recurring revenue of around $25 billion, says Klover.ai. However, its adjusted gross margin deteriorated from an already tight 40% in 2024 to a “concerning” 33% in 2025, says Klover.ai, which notes this falls “far short of an internal corporate target of 46% for that year”.
At the same time, says Klover.ai, internal figures point to a $14 billion loss on $13 billion in revenue for 2026, with cumulative operational losses through to 2028 heading towards $44 billion. More pessimistic forecasts place its losses at between $25 billion and $26 billion, the company says.
Reuters reports have cited sources stating that OpenAI doesn’t expect to be profitable until 2030.
Financial services company The Motley Fool notes that a $1 trillion stock market valuation would mean investors are valuing the company at roughly 40 times its expected annual revenue, reflecting expectations of substantial future growth.
“A business that actively burns more than a dollar for every single dollar of revenue it generates is, by definition, heavily speculative,” says Klover.ai.
The company also has billions in data centre commitments, with The Motley Fool saying reports indicate these extend to $600 billion by 2030.
Free users cost money
Klover.ai estimates that ChatGPT consumer and business subscriptions generated about $2.9 billion of OpenAI’s $3.7 billion revenue in 2024, accounting for roughly 73% of the total. With more than 800 million weekly active users, ChatGPT has built one of the largest consumer monetisation funnels in software history.
However, Klover.ai warns that the subscription model carries structural risks, as heavy users can generate computing costs that exceed the $20 to $200 monthly fees they pay.
OpenAI supports a huge number of free and lightly monetised ChatGPT users, which matters because monetisation quality can be more important than raw user numbers, explains CMC Markets.
As of early 2026, 92% of Fortune 500 companies had adopted ChatGPT in some capacity, says Klover.ai. Enterprise retention stands at 88%, while team tier retention is at 68%.
The Microsoft millstone
A deal with Microsoft means the software giant receives a flat 20% top-line revenue share of OpenAI’s earnings generated from ChatGPT, which Klover.ai says “acts as an immediate, heavy tax on OpenAI’s top line”. It adds that Microsoft is legally entitled to 75% of OpenAI’s profits until its estimated $13 billion initial investment is fully recovered.
“Once that threshold is breached, Microsoft retains a massive 49% profit share up to a predetermined cap of $92 billion to $100 billion,” says Klover.ai.
This partnership also binds OpenAI exclusively to Microsoft Azure for its compute and inference infrastructure needs, preventing OpenAI from negotiating multi-cloud arbitrage or pitting Amazon Web Services against Google Cloud to drive down its greatest variable cost, says Klover.ai.
OpenAI’s “$852 billion valuation is not a reflection of current cash flows, near-term profitability, or traditional SaaS metrics. It is a massive speculative premium placed on the belief that OpenAI will either achieve artificial general intelligence, or establish an insurmountable, monopolistic ecosystem lock-in before capital markets tire of funding its compute deficits,” says Klover.ai.
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