OpenAI Eyed Cursor Before $3B Windsurf Deal
OpenAI’s Strategic Shift in AI Coding Acquisitions
As OpenAI made headlines with its $3 billion acquisition talks for AI coding platform Windsurf, industry observers questioned why the ChatGPT maker didn’t pursue Anysphere (creator of Cursor) instead. New reports reveal OpenAI did consider acquiring the Cursor developer before shifting focus to Windsurf.
Failed Acquisition Talks with Cursor
According to CNBC, OpenAI approached Anysphere twice – first in 2024 and again in early 2025 – about potential acquisition. These discussions ultimately collapsed, leading OpenAI to pursue Windsurf instead. Notably, OpenAI Startup Fund had already invested in Anysphere during its 2023 seed round.
Valuation Differences Tell the Story
The financial landscape explains much about OpenAI’s decision-making:
- Cursor’s valuation: Reportedly seeking funding at $10 billion (Bloomberg)
- Windsurf’s valuation: $3 billion acquisition target
- Revenue comparison: Cursor generates $200M ARR vs. Windsurf’s $40M ARR
Why OpenAI Wants AI Coding Market Share
This acquisition push highlights OpenAI’s urgency to dominate the AI-powered coding assistant space. While the company recently launched its open-source Codex CLI tool, the Windsurf deal suggests OpenAI prefers buying market share over organic growth.
The failed Cursor negotiations and subsequent Windsurf talks reveal the competitive dynamics in AI development tools. As coding assistants become increasingly valuable, major players like OpenAI are willing to spend billions to secure their position in this critical sector.