On May 29, 2026, a breaking news spread rapidly in the AI investment circle: Anthropic completed a $65 billion Series H financing, achieving a post-investment valuation of $965 billion, with the annual recurring revenue "reaching $47 billion, exceeding OpenAI's $25 billion." Anthropic surpassed OpenAI in terms of ARR.

This surge did not happen suddenly in May 2026. When tracing back to the starting point in 2021, Anthropic's valuation was $550 million, while OpenAI's ARR had already surpassed $1 billion during the same period. Within five years, a small team that left OpenAI completed a full curve of following, catching up, and then surpassing the metrics.

Starting at $550 million, but not in the spotlight

In 2021, Dario Amodei led a group of former OpenAI researchers to leave and establish Anthropic. According to public reports, the company raised appr

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