When reports surfaced earlier this week indicating OpenAI was negotiating a $3 billion acquisition of Windsurf, a leading AI-powered coding assistant startup, one immediate question arose among industry analysts: why not buy Anysphere, creator of the hugely successful Cursor, instead?
Indeed, OpenAI’s Startup Fund had already been backing Anysphere since its initial seed funding round in late 2023. Recent reports have confirmed that OpenAI did, in fact, explore acquiring Anysphere at least twice—first in 2024 and again earlier this year—but was not able to secure an agreement. Following these discussions, Anysphere has reportedly shifted gears towards a fundraising round that could value the company at roughly $10 billion.
OpenAI’s pivot towards Windsurf indicates a firm resolve to bolster its capabilities in AI code generation. By comparison, Windsurf is reportedly generating approximately $40 million annually in recurring revenue, whereas Cursor’s revenue reportedly surpasses $200 million annually, positioning Anysphere considerably ahead in terms of market traction and product monetization.
Earlier this week, OpenAI also unveiled “Codex CLI,” an open-source tool designed to help developers generate and edit code directly within terminal environments. Despite these efforts to expand organically, OpenAI’s acquisition talks with Windsurf suggest the company would prefer immediate strategic gains rather than waiting for its in-house tools to capture market share.
This development emphasizes the increasing strategic importance of capturing market leadership in AI-powered coding assistants as tech companies fiercely compete to gain dominance in this rapidly-expanding sector.
