Within the span of a single week in June 2026, the two biggest names in artificial intelligence both took the first formal step toward Wall Street. For investors, the question is no longer whether to pay attention. It is which of the two will be the more interesting IPO to own. Here is how Anthropic and OpenAI compare on the things that actually drive returns: valuation, growth, profitability, business model, and structure.
The race to list
Anthropic moved first, filing a confidential draft registration with the SEC around June 1, 2026 and targeting a listing as soon as October 2026 on the Nasdaq, with Goldman Sachs and JPMorgan leading. OpenAI followed within days, filing confidentially and eyeing a window that runs from late 2026 into 2027. Whoever prices first is likely to capture the largest share of early investor enthusiasm in what Goldman Sachs has called a multi-billion-dollar AI IPO wave. Right now, that first mover looks like Anthropic.
Valuation: who is worth more
For the first time, Anthropic is the more valuable of the two in private markets. Its latest round lifted it to about $965 billion, edging past OpenAI, which was valued near $852 billion in March 2026. At IPO, OpenAI is reported to be targeting somewhere between roughly $730 billion and $1 trillion, while Anthropic could cross the trillion-dollar line on debut if markets cooperate. Either way, both would list at extreme multiples on current revenue, so you are paying for years of future growth rather than today's numbers.
Growth and profitability
This is the sharpest contrast between them.
- Anthropic has grown explosively, with its annualized revenue run-rate climbing several-fold within months on the back of enterprise demand, the Claude models, and Claude Code in software development. It is also reported to be approaching operating profitability far sooner than its rival.
- OpenAI is larger in absolute terms, with an annualized run-rate heading toward roughly $20 billion, but its losses are mounting and it does not expect to turn a profit until around 2030. Recent reports also suggested it missed some internal revenue and user targets.
In short, Anthropic offers faster growth and a clearer path to profit, while OpenAI offers greater scale today alongside heavier losses.
Different businesses, different risks
The two are not simply faster and slower versions of the same company. They monetize differently, which changes the risk you take on.
OpenAI is the consumer giant. ChatGPT has more than 900 million weekly active users and over 50 million paying subscribers, an unmatched brand and distribution moat. The flip side is the cost of serving an enormous free user base, very heavy capital spending, and a complex relationship with Microsoft, which owns roughly 27% and holds long-term rights to OpenAI's models and products.
Anthropic is the enterprise specialist. Its revenue skews toward higher-margin, stickier business and developer customers, with particular strength in coding and security, and it counts Google and Amazon among its strategic backers. The trade-offs are a smaller consumer footprint and a mission-driven posture, including public limits on how its AI can be used, that can constrain certain revenue.
Structure and governance
Governance is unusually important here, and it favors neither cleanly.
OpenAI completed a restructuring in late 2025 into OpenAI Group PBC, a public benefit corporation controlled by the nonprofit OpenAI Foundation, which retains around a quarter of the company. That restructuring removed an old cap on investor returns and cleared the legal path to a listing after a lawsuit from Elon Musk was dismissed. But nonprofit control, plus the Microsoft stake, leaves public shareholders further from the steering wheel than in a typical company.
Anthropic is also a public benefit corporation, with a more conventional cap table but the same mission-bound DNA. For an investor, both mean you are buying into companies that have formally committed to goals beyond maximizing shareholder profit.
So which is the more interesting IPO?
It comes down to what you weight. If you prioritize revenue growth, a nearer path to profitability, and a cleaner enterprise model, the case points toward Anthropic. If you prioritize sheer scale, consumer brand power, and the broadest optionality in AI, the case points toward OpenAI. Both are speculative bets at close to a trillion dollars, and in practice the one that lists first at a sensible price may simply offer the better entry. There is also no rule that says you must choose only one.
How to get exposure today
Neither company is public yet, so the only way to take a position right now is through pre-IPO markets, which track each company's implied valuation rather than offering direct equity. Each carries its own liquidity and risk profile.
OpenAI:
Anthropic:
When they list
Once either company is trading, you will be able to buy the listed shares, and try for a retail allocation, through a broker:
Bottom line
Anthropic and OpenAI are the two defining AI listings of this cycle, and they offer genuinely different bets. Anthropic is the faster-growing, enterprise-led name with a nearer line to profit and, for now, the higher valuation and the earlier listing date. OpenAI is the larger, consumer-dominant platform with a deeper brand but heavier losses and a more tangled ownership structure. Watch which one prices first and at what multiple, decide which profile fits your conviction and time horizon, size any position to survive the volatility that follows hot AI debuts, and remember you can already take a position on either through pre-IPO markets before the bell rings.
Not investment advice.