The Trillion‑Dollar Question: Can AI IPOs Live Up To The Hype?

OpenAI and Anthropic are racing to public markets with combined private valuations approaching $2 trillion. The numbers are real. Whether public investors will pay for them is another matter.

Key Metrics

• Anthropic valuation: $965B (Series H close, June 2026)
• OpenAI valuation: $852B (Last funding round, March 2026)
• Combined IPO raise estimate: $200B+ (vs. $45B entire US IPO market in 2025)

The Setup

On June 1st, Anthropic filed confidentially for an IPO. OpenAI is expected to follow within days or weeks, targeting a listing as early as September. Both companies arrive at public markets after historically lucrative stints as private companies - and with numbers that, a few years ago, would have been unthinkable for pre-profit AI labs.

Anthropic's annualised revenue reportedly crossed $44 billion in May 2026, and the company is on track to post its first-ever operating profit - approximately $559 million - in Q2 2026. OpenAI, meanwhile, crossed $20 billion in annualised revenue by end-2025, with ChatGPT now serving 900 million weekly active users. The revenue case is no longer speculative.

"Three IPOs together could demand north of $200 billion from public markets. The entire US IPO market raised just $45 billion in all of 2025."

Revenue Trajectory

Company	ARR (Annual Recurring Revenue)	Quarterly Revenue	ARR (Previous Year)
Anthropic	~$44B (May 2026)	$4.8B (Q1 2026)	-
OpenAI	~$25B (Feb 2026)	-	~$2B (2023)

The Bull Case: The Demand Unlock Thesis

Institutional investors have spent years accessing AI through proxies - Nvidia for chips, Microsoft for its OpenAI stake, Alphabet for Anthropic. The moment pure-play labs are publicly available, that pent-up demand unlocks. With an estimated $8 trillion sitting in US money market funds, absorbing even a $60B Anthropic raise represents a rounding error.

The Bear Case: The Valuation Gravity Problem

Of the five largest IPOs in modern history, only Visa significantly outperformed markets. Saudi Aramco listed near $1.7 trillion in 2019 and still trades below issue price. Facebook fell 38% in its first six months. Frontier valuations carry frontier risk - and $965B for a company posting its first operating profit is frontier by any measure.

Key Risks To Watch

Compute cost is the elephant in the room. Anthropic's gross margins were negative 94% in 2024 - a number that has since improved dramatically, but the unit economics of running frontier AI models remain brutal. Free users, who make up the bulk of usage, are a structural drain. The enterprise pivot - where over 1,000 businesses already spend more than $1 million annually - is the margin story investors need to believe.

OpenAI faces a more complex path. The company only recently completed its conversion from a nonprofit with a for-profit subsidiary into OpenAI Group PBC - a structural shift that was necessary for a public listing but opens governance questions investors will interrogate. The CFO has publicly cautioned the company isn't ready to go public; a missed revenue target reported by the Wall Street Journal adds friction. The Elon Musk lawsuit remains unresolved.

The question isn't whether these companies are valuable. It's whether the public market - which prices on earnings, multiples, and comparables - can meet the private market where it has been operating.

The Broader Market Test

This IPO cycle has no modern parallel in terms of scale. Goldman Sachs projected 2026 IPO proceeds could reach $160 billion - and that was before the current wave fully materialised. SpaceX's listing alone, targeting $75 billion, represents more than the entire 2025 US IPO market. OpenAI and Anthropic following in Q4 would make this the largest year for capital formation since the dot-com era. That comparison isn't chosen lightly: a weak debut from any of the three would stress-test the entire valuation framework for pre-profit, AI-adjacent companies globally.

The optimists argue this cycle is structurally different. AI infrastructure spending is backed by long-term hyperscaler commitments - AWS, Google Cloud, and Microsoft Azure have collectively committed billions to Anthropic and OpenAI. Revenue is real, enterprise adoption is accelerating, and the 80% of Anthropic's revenue coming from enterprise customers gives the business a durability that 2000-era internet companies lacked. The bears note that durability and trillion-dollar valuations are different propositions.

What happens when the roadshows begin will tell us something fundamental: not just about these two companies, but about how public markets have internalised - or haven't - the AI moment we've been living through.

Sources: Bloomberg, CNBC, Wall Street Journal, Reuters, SEC filings. Valuation figures reflect most recent known funding rounds and are subject to final IPO terms. Revenue figures are annualised run rates as reported; unaudited until S-1 filings are public.