📖 6 min read
Two of the world’s most powerful AI companies filed for IPOs within a single week of each other. Anthropic went first on June 1, 2026. OpenAI followed on June 8. Both filings are confidential S-1s – the regulatory step that precedes a public listing on Wall Street. Nothing like this has ever happened in AI before, and the race has a twist: Anthropic, the smaller and quieter rival, is currently valued higher than OpenAI.
The Numbers That Make This Real
Anthropic filed at a valuation of $965 billion, buoyed by a recent $65 billion Series H funding round. OpenAI filed at roughly $852 billion – about $113 billion less than its rival. OpenAI’s annualized revenue run rate sits above $25 billion as of early 2026, having scaled from $2 billion in 2023 to $6 billion in 2024 to $20+ billion in 2025. That is a 10x revenue expansion in two years.
| Metric | OpenAI | Anthropic |
|---|---|---|
| IPO filing date | June 8, 2026 | June 1, 2026 |
| Current valuation | ~$852 billion | ~$965 billion |
| Annual revenue (run rate) | $25B+ | Not publicly disclosed |
| Projected cash burn (2026) | ~$27 billion | Not publicly disclosed |
| Weekly active users | 900 million (ChatGPT) | Not publicly disclosed |
| Key corporate backer | Microsoft (~27% stake) | Amazon + Alphabet |
OpenAI said its listing “may be a while” and the timing is undecided. The company was reported to be targeting a September 2026 IPO by some investors, but the formal statement hedged heavily – framing the filing as preserving “the option to go public sooner if that ends up being best.” That kind of language is unusual for an S-1 announcement.
Why Anthropic Filed First – And Why That Matters
This rivalry traces back to 2020, when Dario Amodei, Daniela Amodei, and a group of other researchers left OpenAI to found Anthropic. The split was bitter. Former colleagues, now direct competitors, are now racing to Wall Street.
📧 Want more like this? Get our free The 2026 AI Playbook: 50 Ways AI is Making People Rich — Free for a limited time - going behind a paywall soon
Anthropic’s decision to file first on June 1 appears deliberate. In the AI IPO race, narrative momentum matters. Being first to file signals financial readiness, competitive confidence, and investor demand. The $65 billion Series H – backed in part by Apollo and Blackstone financing a $35 billion expansion of AI computing capacity using Broadcom chips – pushed Anthropic’s valuation above OpenAI’s for the first time in the companies’ histories.
OpenAI responded within seven days. The compressed timeline between the two filings is nearly unprecedented for companies of this size. Both companies are now navigating the same market window, competing for the same pool of institutional investors, and trying to price their shares before the other sets the comparable benchmark.
Join 2,400+ readers getting weekly AI insights
Free strategies, tool reviews, and money-making playbooks - straight to your inbox.
No spam. Unsubscribe anytime.
The $27 Billion Problem OpenAI Has to Answer
Revenue growth is extraordinary. Profitability is not there yet. OpenAI’s projected cash burn for 2026 is roughly $27 billion – mostly compute costs, research headcount, and infrastructure. At a $25 billion revenue run rate with $27 billion in annual spending, the unit economics are still negative. OpenAI’s 2025 restructuring – converting its for-profit arm into a Public Benefit Corporation controlled by the nonprofit OpenAI Foundation – was a prerequisite for an IPO, but it also created a governance structure investors will need to understand and accept.
Microsoft remains OpenAI’s largest outside investor with a roughly 27% stake in the for-profit unit. That relationship is both an asset (massive distribution, Azure integration) and a complexity (what happens to the Microsoft partnership post-IPO when public shareholders have their own demands?).
Anthropic has its own version of this problem. Amazon and Alphabet both hold significant stakes, and Anthropic’s “AI Safety” brand positioning – including a June 2026 blog post calling for a global AI pause over control risks – creates its own tension. It is hard to ask investors to value you near $1 trillion while simultaneously arguing the technology you are building might be dangerous enough to pause.
The Broader 2026 Mega-IPO Pipeline
OpenAI and Anthropic are not operating in isolation. SpaceX has also filed for an IPO at a reported $1.75 trillion valuation, which would rank as the largest IPO in history if completed. The combined market cap of the three companies – all filing in the same calendar year – exceeds $3.5 trillion. That is an enormous ask from public markets that are still digesting a broader tech selloff and debate over whether AI infrastructure spending is creating durable value or a late-cycle bubble.
Perplexity, the AI search startup, is taking a different approach entirely. CEO Aravind Srinivas confirmed the company is sticking to a 2028 IPO target. As of March 2026, Perplexity’s ARR was $450 million, targeting $656 million by year-end. Small numbers relative to OpenAI, but Perplexity has chosen to let the giants test the market first.
What Retail Investors Can Actually Do Right Now
Both companies are still private. You cannot buy OpenAI or Anthropic shares today. But both have large public-market proxies:
- Microsoft (MSFT) – holds roughly 27% of OpenAI’s for-profit unit. Every dollar of OpenAI revenue growth flows partly through Microsoft’s Azure cloud business.
- Amazon (AMZN) – major Anthropic investor, provides AWS infrastructure for Claude deployments.
- Alphabet (GOOGL) – also a major Anthropic investor, while simultaneously competing with both companies through Gemini.
When the IPOs do happen, both filings will go public roughly 15 days before each company’s roadshow. That is when the actual financials become visible and the pricing process begins. Until then, the confidential S-1 status means we are working with disclosed metrics and third-party estimates.
The Honest Question: Is Any of This Worth the Valuations?
$852 billion for OpenAI implies a price-to-revenue multiple of roughly 34x on $25 billion in ARR. Anthropic at $965 billion has not disclosed revenue, but estimates put it well below OpenAI’s – making its multiple potentially even higher. For context, Salesforce trades at around 8-10x revenue. Nvidia, the most prized company in the AI stack, trades at roughly 25x revenue – and Nvidia is profitable.
OpenAI burning $27 billion a year means it needs to either reach profitability fast or keep raising capital. An IPO solves the capital problem temporarily, but public market investors have less patience for losses than private venture firms. The first earnings call after a public listing will be a very different conversation than a Series H pitch deck.
The bull case is that AI is a platform shift on the scale of the internet, and the companies controlling the frontier models will capture durable, compounding value. The bear case is that models are commoditizing fast, open-source alternatives are closing the gap, and compute costs will never fully fall below revenue growth.
Both cases are live. Neither is obviously wrong.
BetOnAI Verdict
The Anthropic-then-OpenAI double IPO filing in June 2026 is the most significant event in AI finance since ChatGPT launched. The race itself is real, the revenue numbers are real, and the competitive tension is real. But at near-trillion-dollar valuations with negative unit economics, the public market test is going to be brutal in ways that private funding rounds are not.
If you want AI exposure today: Microsoft, Amazon, and Alphabet are the accessible proxies. They are not pure plays, but they have real revenue, real profits, and real AI integration. When the IPO roadshows actually begin, watch the pricing closely – the gap between the confidential-filing valuation and the IPO price will tell you a lot about how hungry or skeptical institutional investors actually are.
The AI IPO race is now officially on. Who wins depends less on who has the better model and more on who convinces Wall Street the losses are temporary.
Sources
- TechCrunch – Following Anthropic, OpenAI files confidentially for IPO (June 8, 2026)
- CNBC – OpenAI confidentially files for IPO, prepping Wall Street for mega AI debut
- Reuters – Anthropic v. OpenAI: Behind the bitter battle for the future of AI (June 11, 2026)
- Tech Insider – OpenAI IPO: $850B Valuation, $25B Revenue (2026)
- CNBC – Perplexity plans IPO in 2028 regardless of what happens to Anthropic or OpenAI
Enjoyed this? There's more where that came from.
Get the AI Playbook - 50 ways AI is making people money in 2026.
Free for a limited time.
Join 2,400+ subscribers. No spam ever.