OpenAI and Anthropic Enter High-Stakes IPO Race Powered by Massive Enterprise and Financial Vertical Revenues

In late May 2026, the competitive race between the world's leading AI labs, OpenAI and Anthropic, has transitioned into a high-stakes IPO horse race. Both companies are preparing to go public as they demonstrate explosive revenue growth, driven primarily by enterprise adoption and deep vertical integrations in financial services.

The IPO Timeline and Prediction Market Shifts

• OpenAI IPO Filing: On May 20, 2026, reports emerged that OpenAI is preparing to confidentially file a draft of its IPO prospectus as soon as Friday, May 22, 2026. The company is working with bankers at Goldman Sachs and Morgan Stanley, aiming for a public debut as early as September 2026. This sudden acceleration has been driven by CEO Sam Altman, reportedly pushing for a faster debut than CFO Sarah Friar.
• Anthropic IPO Timeline: Anthropic is also actively preparing for a 2026 IPO, with Bloomberg previously reporting that the company is weighing a public debut as soon as October 2026.
• Prediction Market Reaction: Following the news of OpenAI's imminent filing, traders on prediction platforms Kalshi and Polymarket dramatically shifted their outlooks. On Kalshi, OpenAI's probability of going public before Anthropic surged to 83% (up from just 32% earlier in the week).

Explosive Revenue Growth and Enterprise Parity

Both companies are disclosing mind-boggling financial metrics as they prepare their prospectuses:

• OpenAI Financials: OpenAI generated approximately $5.7 billion in revenue in Q1 2026, maintaining a narrow lead over Anthropic.
  • Enterprise Traction: Enterprise revenue now accounts for more than 40% of OpenAI's total revenue and is on track to reach 50% parity with consumer revenue by the end of 2026.
• Anthropic Financials: Anthropic is on track to generate $10.9 billion in revenue in Q2 2026, more than doubling its $4.8 billion in Q1 2026 revenue and surpassing its total sales for all of 2025 ($10 billion).
  • Profitability: If Anthropic hits its Q2 target, it will post its first profitable quarter.
  • Valuation Talks: Anthropic is currently in talks with investors to raise a primary funding round at a $900 billion valuation, which would top OpenAI's latest private valuation of more than $850 billion.
  • Compute Infrastructure Commitments: To support its massive enterprise and developer demand, Anthropic recently struck a deal with Elon Musk's SpaceX to utilize the entire compute capacity of the Colossus 1 data center in Memphis, Tennessee. According to SpaceX's IPO prospectus, Anthropic will pay SpaceX $1.25 billion per month through May 2029.