On June 1, Anthropic filed a confidential S‑1, a move that comes just weeks after the company closed a $65 billion Series H round that pushed its valuation to $965 billion. The filing follows an impressive jump in annualized revenue—from a modest $4 billion in mid‑2024 to $47 billion in May 2026—an 11‑fold increase in just 14 months. Anthropic’s leadership has already signaled that the company expects its first profitable quarter in 2026.

OpenAI, by contrast, is valued at roughly $852 billion and reports an annualized revenue run‑rate of about $30 billion. Internal projections, however, paint a starkly different picture: the firm is slated to record a $14 billion loss in 2026, with cumulative losses of $44 billion through 2028, and profitability not anticipated until 2029.

The divergence is most evident in the enterprise coding arena. Claude Code, Anthropic’s terminal‑based coding assistant, now commands 54 % of the market, eclipsing OpenAI’s Codex at 21 %. Coding accounts for 51 % of all enterprise AI spending, and Claude Code alone has crossed $2.5 billion in annualized revenue. Because enterprise software carries high switching costs, teams that embed Claude Code into their development pipelines are unlikely to move to a competitor unless a compelling reason emerges—creating a large, sticky customer base for Anthropic.

OpenAI’s strength lies elsewhere. Brand recognition and a strategic partnership with Microsoft give the company a distribution channel that reaches virtually every enterprise via Azure and Microsoft 365. Its consumer product, ChatGPT, boasts a user base far larger than Claude’s. Yet the introduction of ads into the free ChatGPT tier in 2024 signals that monetizing the consumer market is proving more difficult than early growth suggested.

For investors, the two firms’ trajectories illustrate a clear divide. Anthropic’s rapid revenue expansion and a near‑term profit outlook make it an attractive prospect for those focused on enterprise AI. OpenAI’s broader consumer reach and Microsoft partnership offer a different set of risks and rewards, but the projected multi‑year losses and a longer path to profitability temper enthusiasm.

Unresolved challenges remain on both sides. Anthropic is embroiled in a dispute with the U.S. Department of Defense over the use of its models for military and surveillance purposes—a conflict that could affect its customer base. OpenAI faces multiple lawsuits alleging copyright infringement and has undergone internal restructuring that may shape its future direction.

Both companies are slated to seek public markets this fall, and the timing of their IPOs will likely influence investor sentiment. In short, Anthropic’s recent funding, dominance in enterprise coding, and near‑term profitability outlook position it as a compelling IPO candidate, while OpenAI’s larger brand and distribution network are counterbalanced by significant projected losses and a longer path to profitability.