OpenAI Just Pushed Its IPO to 2027. Here’s What That Decision Actually Reveals.

OpenAI filed a confidential S-1 with the SEC on May 22, 2026 — one week after rival Anthropic did the same. For most of the summer, the AI world assumed the two companies would race each other to market in a historic twin listing. Then, last week, Bloomberg reported that OpenAI’s leadership has concluded they will likely go public after Anthropic, with a debut now targeted for 2027.

Ceding the first-mover advantage is a significant decision. The reasoning behind it says as much about OpenAI’s current situation as anything the company has said publicly all year.

Why OpenAI Is Waiting

OpenAI’s CFO Sarah Friar has been notably candid about the company’s IPO readiness — or the lack of it. Friar told investors earlier this year that the company “isn’t ready to be a public company,” and that there are “things we want to do that are likely easier as a private company.” That framing, coming from the person responsible for taking the company public, is unusual and telling.

The core issue is financial complexity. OpenAI’s revenue picture is genuinely difficult to present clearly to public market investors. The company generated $13.1 billion in revenue in 2025 and has accelerated to approximately a $24 billion annualised run-rate as of April 2026 — but it remains significantly cash-flow negative due to the cost of training frontier models and operating ChatGPT at scale for over 900 million weekly users.

More importantly, OpenAI’s capital structure is extraordinarily tangled. After its October 2025 conversion to a Public Benefit Corporation, the ownership breaks down as follows: the non-profit OpenAI Foundation holds 26% plus a warrant; Microsoft holds roughly 27%; current and former employees and investors hold the remaining 47%. Elon Musk, an early co-founder, has active litigation seeking to challenge aspects of the for-profit conversion. The SEC comment process for a company with this ownership structure, ongoing litigation from a prominent former insider, and a novel corporate form is considerably more complex than a standard tech IPO.

The Tech Stock Volatility Factor

Beyond the structural issues, recent volatility in the broader tech market has influenced OpenAI’s timing calculations. Friar has cited this explicitly — noting that market conditions in September made a 2026 listing less attractive than it appeared in May.

This is a reasonable concern. A company pricing at a $1 trillion valuation needs stable, receptive markets for institutional investors to absorb the offering. The AI sector specifically has seen significant multiple compression in some listed names this autumn as investors reassess whether the pace of enterprise AI adoption justifies the valuations assigned during the mid-year frenzy. OpenAI would rather wait for a window where the market is unambiguously enthusiastic than push through in conditions that produce a disappointing first-day pop and a declining post-IPO trajectory.

OpenAI’s revenue run-rate is roughly $24 billion annualised as of April 2026. Anthropic’s Q2 revenue alone was $11.5 billion — suggesting that on a forward-revenue basis, Anthropic may be the larger of the two by the time either company actually lists publicly.

Letting Anthropic Go First: A Strategic Choice, Not a Concession

The conventional framing of this decision is that OpenAI is “losing the race” to Anthropic. That’s not quite right. Letting a rival list first has genuine strategic advantages in an environment where both companies are priced at unprecedented multiples with limited public financial disclosure.

Anthropic’s IPO will serve as a real-time market experiment: what multiple does the public market actually assign to a frontier AI lab with extraordinary revenue growth but high capital intensity and uncertain long-term profitability? The answer to that question — visible in real time through Anthropic’s roadshow, pricing, and first weeks of trading — gives OpenAI’s bankers a far better data point for calibrating OpenAI’s own valuation than anything in their models today.

If Anthropic prices at $2 trillion and trades well above that in its first weeks, OpenAI’s case for a $1 trillion or higher valuation is significantly strengthened. If Anthropic prices and immediately declines — if the market decides that 60x forward revenue is too much to pay for a loss-making AI lab — OpenAI will be grateful it waited.

What OpenAI Is Doing With the Extra Time

The delay gives OpenAI time to do three things that are harder as a public company. First, continue restructuring its corporate governance — the Foundation-controlled PBC structure is novel and still being tested legally. Second, work through the Musk litigation, which could create material disclosure complications in a public S-1 if still active. Third, demonstrate a clearer path to profitability — Friar has said OpenAI aims to show positive operating cash flow before listing.

That last point is where GPT-6 Astra matters. The model launched last month with significantly better performance-per-dollar than its predecessors — and enterprise contracts priced at Astra’s capability level should carry substantially better margins than contracts priced on GPT-4 or GPT-5 economics. If Astra’s launch translates into improved unit economics over the next two quarters, OpenAI’s financial story for a 2027 IPO is considerably cleaner than anything it could tell today.

The Bottom Line for Investors

Anyone watching the AI IPO wave as an investor now has a sequenced set of events to track. Anthropic goes first — roadshow beginning mid-October, listing targeted before US Thanksgiving. OpenAI follows in 2027, with timing dependent on market conditions, litigation resolution, and financial progress. SpaceX already listed in June at $1.75 trillion and is trading above its listing price.

The sum of these three companies’ targeted valuations — roughly $4.75 trillion — exceeds the GDP of Germany. Whether public markets sustain that level of enthusiasm for frontier AI companies over the next 12 to 18 months is the central question of 2027’s investing landscape. For more context, see our earlier coverage of the OpenAI IPO filing and what it means for the AI industry and our breakdown of Anthropic’s record Q2 revenue.

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