Anthropic has achieved a remarkable financial milestone, with its annualized revenue soaring to nearly $45 billion, marking a fivefold increase in the first five months of 2026. This growth surpasses OpenAI's revenue by approximately 35%, as OpenAI's annualized revenue remains between $30–33 billion. Anthropic's rapid ascent from $9 billion at the end of last year has surprised the industry, especially as it prepares for an IPO showdown with OpenAI. Anthropic's profitability is also noteworthy, with an expected operating profit of $559 million in the second quarter and a 5% profit margin, driven by strong enterprise demand for its high-margin services. In contrast, OpenAI faces significant financial challenges, with an operating profit margin of -122% in the first quarter, resulting in a net loss of at least $7 billion per quarter. The differing business models of the two companies highlight their financial positions, with Anthropic focusing on enterprise tools and OpenAI grappling with high server costs and revenue-sharing agreements with Microsoft.