OpenAI’s Strategic Moves: From Cursor to Windsurf in the AI Coding Assistant Race

OpenAI initially approached Anysphere, the maker of Cursor, for acquisition before shifting focus to Windsurf, highlighting the competitive landscape of AI coding assistants.

In a revealing turn of events, OpenAI’s journey to dominate the AI coding assistant market took a notable detour. Before entering talks to acquire Windsurf for a staggering $3 billion, OpenAI had its sights set on Anysphere, the creator behind the rapidly growing Cursor. Despite being an early investor in Anysphere since its seed round in late 2023, OpenAI’s acquisition attempts in 2024 and earlier this year fell through. Anysphere is now eyeing a capital raise at a $10 billion valuation, as per Bloomberg.

This pivot to Windsurf, which boasts $40 million in annualized recurring revenue (ARR), underscores OpenAI’s urgency to cement its position in the code generation sector. Comparatively, Cursor’s ARR stands at an impressive $200 million. While OpenAI recently unveiled its Codex CLI “agent,” the pursuit of Windsurf suggests a strategic preference for established market players over organic growth. The AI coding assistant arena is heating up, and OpenAI’s moves are a clear indicator of the high stakes involved.