OpenAI was hoping its new GPT-5.5 model, released last week to strong benchmark scores, would shift the narrative.

The problems are mounting up faster than the company can answer them.

The ChatGPT maker missed its internal target of one billion weekly active users by year-end.

It also missed its annual ChatGPT revenue target after Google‘s (NASDAQ:GOOGL) Gemini ate into market share, and missed multiple monthly revenue targets this year as Anthropic gained ground in coding and enterprise.

CFO Sarah Friar has reportedly told colleagues she is worried OpenAI may not be able to pay for future computing contracts if revenue does not accelerate.

The company is on the hook for roughly $600 billion in compute commitments and expects to burn through its recent $122 billion funding round, the largest in Silicon Valley history, within three years.

Friar has also pushed back on CEO Sam Altman’s preferred year-end IPO timeline, saying OpenAI is not yet ready for the financial reporting demands of a public company.

Anthropic Stays Ahead On Polymarket

Despite GPT-5.5 getting good reviews, Polymarket still gives OpenAI only a 9% chance it has the best AI model by the end of June.

Anthropic is at 50%, ahead of Google at 36% on almost $5 million in volume.

A separate Polymarket contract gives OpenAI just a 32% chance of completing an IPO by year-end, down from a peak of over 50% in February.

The Musk Trial Begins

Jury selection began yesterday in Oakland federal court in Elon Musk‘s lawsuit.

Musk seeks damages exceeding $180 billion, the removal of Altman and President Greg Brockman, and the unwinding of OpenAI’s for-profit restructuring.

Any one of those outcomes would likely complicate the IPO path. Anticipated testimony includes Altman, Ilya Sutskever and Microsoft (NASDAQ:MSFT) CEO Satya Nadella.

The case turns on a breach of charitable trust claim, the argument that Musk’s roughly $40 million in original funding was intended for an open-source nonprofit.

Judge Yvonne Gonzalez Rogers cited Brockman’s own diary in allowing the case to proceed, including the line that the restructuring was “the only chance we have to get out from Elon.”

Legal experts think Musk is likely to lose, but Kalshi now disagrees.

The contract on whether Musk wins was over 55% in January and bottomed near 33% in March. With proceedings now underway, it has rallied to 57%, on $408,761 in total volume.

OpenAI launched the AI mania that has carried tech valuations for three years. The next few months will determine whether it remains the company defining the era or a footnote in someone else’s.

Image: Shutterstock