Enterprise JUN 28, 2026

Enterprise 'tokenmaxxing' hangover hits OpenAI and Anthropic on eve of dual IPO

CFOs are capping AI budgets and routing to cheaper open-weight models as both labs race to list at near-trillion-dollar valuations.

BY GRETA REINHART · ENTERPRISE SAAS

Lindy, a roughly 25-person AI startup, recently moved 100% of its traffic off Anthropic’s Claude models to the open-weight DeepSeek and now projects savings in the millions within months. “We did it, and you could see that cost curve go down, like, crash to the ground,” CEO Flo Crivello told CNBC. That sentence, multiplied across thousands of enterprise budgets, is the shadow hanging over the most anticipated dual IPO in tech.

Anthropic filed a confidential S-1 on June 1; OpenAI followed one week later on June 8. Bloomberg reports OpenAI is weighing a listing as late as 2027, effectively conceding that Anthropic will get to the bell first, possibly as soon as October. The valuations going in are extraordinary: Anthropic’s last private round marked it at $965 billion, and OpenAI was carried at $852 billion in late March.

The numbers underneath are growing fast, but unevenly. Anthropic disclosed a $47 billion annualized run rate in May, against $10 billion in 2025 revenue. OpenAI was pacing near a $25 billion run rate earlier this year on $13.1 billion in 2025 revenue. Per its filing, OpenAI projects burning $85 billion in 2028 even after doubling sales. Anthropic is paying SpaceX $1.25 billion monthly for Colossus 1 compute, with the contract running through May 2029.

Gil Luria, an analyst at D.A. Davidson, frames the timing bluntly. “Current growth rates for Anthropic and OpenAI are the fastest they will ever be, which is mostly a matter of basic math.” He adds: “That is a good reason to go public now, as is the concern that some of their largest enterprise customers may start limiting their out-of-control token spend.”

That spend is already being audited. OpenAI rolled out enterprise analytics and credit-spend controls earlier in June. Microsoft, which has put more than $13 billion into OpenAI and as much as $5 billion into Anthropic, launched its own suite of low-cost models the same month. Satya Nadella has warned of “a world where every company across every sector is ceding value to a few models.” Glean CEO Arvind Jain still estimates roughly 95% of enterprise AI usage runs on frontier models. The IPO window is the gap between that 95% and the cost curve Crivello just watched crash to the ground.

Sources

About the author

Greta Reinhart

ENTERPRISE SAAS

Greta Reinhart tracks the enterprise software stack from San Francisco — data platforms, AI bundling, seat pricing, and channel checks across the largest SaaS vendors. She files on go-to-market shifts, packaging changes, and quarterly enterprise reads.