The AI industry is about to witness something unprecedented: two companies racing to become the first trillion-dollar artificial intelligence firm to go public. OpenAI may have filed its paperwork first, but the numbers tell a different story.
According to FinanceFeeds, Anthropic’s latest private valuation sits at $900 billion, ahead of OpenAI’s $852 billion mark. More importantly, Anthropic is pulling in $43 billion in annual revenue compared to OpenAI’s sub-$30 billion run rate. The gap is widening, and crypto prediction markets are taking notice.
The numbers behind the race
OpenAI confidentially filed its S-1 with the SEC on May 22, 2026, targeting a Q4 2026 listing. Goldman Sachs and Morgan Stanley are handling the deal. The company is aiming for a valuation between $852 billion and $1 trillion when it goes public.
Anthropic hasn’t filed yet, but it’s moving fast. The company raised its valuation from $380 billion in February to $900 billion by May 2026. That’s a massive jump driven by real revenue growth:
- Annual revenue hit $43 billion in April 2026, up from $9 billion at the end of 2025
- Over 1,000 enterprise customers are paying $1 million or more per year
- The company signed a $15 billion annual compute deal with SpaceX
The revenue multiple tells the story. Anthropic trades at 20.9x sales compared to OpenAI’s 28.4x multiple. For a company with higher absolute revenue, that lower multiple suggests stronger fundamentals.
What the markets are saying
Polymarket launched prediction markets for both companies in May 2026. The results are striking:
- 96% probability that Anthropic will be worth more than OpenAI at some point in 2026
- 75.5% probability that OpenAI will list first
- 89% chance OpenAI closes above $800 billion on its first day
- 77% chance OpenAI hits $1 trillion
These numbers aren’t just retail speculation. The markets have attracted serious institutional money, with over $13 million in open interest on similar SpaceX contracts.
The Nasdaq Private Market shows similar sentiment. Anthropic shares traded at $477.02 on May 5, 2026 – a 1,500% increase year-over-year. That’s institutional money voting with real dollars.
The underwriter challenge
Both companies share the same investment banks: Goldman Sachs and Morgan Stanley. Anthropic added JPMorgan to its roster. This creates an unusual problem.
If both companies go public in Q4 2026 as planned, it would be the largest sector-concentrated equity issuance in tech history. The same teams would have to absorb billions in stock from competing companies within months of each other.
Institutional allocation capacity is limited. Expect at least one syndicate to drop coverage if the timing overlap holds.
Revenue divergence drives the race
The real story is in the business fundamentals. Anthropic’s revenue jumped nearly 5x in one year, driven by enterprise customers paying serious money. OpenAI has missed internal revenue targets, according to industry reports.
This matters because public market investors care about sustainable growth. Anthropic’s customer base – over 1,000 companies spending $1 million annually – provides predictable recurring revenue. That’s what gets institutional investors excited about IPO allocations.
The SpaceX compute deal also signals something important. A company committing $15 billion annually in compute spend is preparing for the balance sheet scrutiny that comes with being public.
Regulatory hurdles and crypto markets
The SEC review process gives OpenAI a head start, but only by about 90 days. The agency has 30 days to review confidential filings, then companies get 21 days to respond. OpenAI’s May 22 filing puts a public amendment around August or September 2026.
Meanwhile, crypto markets are already trading synthetic exposure to both companies. Binance launched OpenAI perpetuals, and Hyperliquid is expected to list both companies soon. These markets trade 24/7 and often lead traditional price discovery.
One warning: SPV-backed tokens claiming to represent actual shares fell 50% last week after both companies said unauthorized share transfers are void. Stick to synthetic contracts that don’t claim ownership.
Three predictions for 2026
Based on the current timeline and market signals, here’s what’s likely to happen:
First, OpenAI will publicly file its amended S-1 between August and September 2026. The SEC comment process averages 90-120 days, putting the public filing right around Labor Day. This supports the 75% Polymarket probability of a 2026 listing.
Second, Anthropic will raise one more private round at $1 trillion-plus before filing its own S-1 in October. With $43 billion in revenue and 1,000+ enterprise customers, the private market can support another round. This lets Anthropic claim the $1 trillion mark before going public.
Third, the Polymarket prediction will prove correct – Anthropic will be valued higher than OpenAI by the end of 2026. This might happen through private market valuation before both companies are actually trading publicly.
Why this race matters
This isn’t just about two AI companies. It’s a test of different business models in the public markets. OpenAI represents the consumer-focused, viral growth approach. Anthropic represents enterprise-first, revenue-driven scaling.
The outcome will influence how other AI companies approach their own public offerings. More importantly, it will show whether public markets reward sustainable enterprise revenue over viral consumer adoption.
For investors, this race offers a rare opportunity to see two directly competing companies test the public markets simultaneously. The last comparable situation was LinkedIn versus Twitter in 2010-2011, where the boring enterprise play (LinkedIn) ultimately outperformed the flashier consumer brand.
Both companies will likely hit trillion-dollar valuations eventually. The question is which business model gets there first – and which one stays there.
