OpenAI VCs Double‑Down on Anthropic, Signaling Investor Loyalty Is Nearly Gone.

The dual‑investment pattern underscores how capital is now flowing more toward the AI sector as a whole than toward any single champion. According to TechCrunch, at least twelve firms that have already committed capital to OpenAI are also listed as backers of Anthropic’s $30 billion raise, including Founders Fund, Iconiq, Insight Partners and Sequoia Capital. The overlap extends beyond pure‑play venture houses; asset managers such as Fidelity, D1 and TPG have also taken seats in both rounds, reflecting a broader “public‑stock‑style” approach to private AI deals (TechCrunch). Even BlackRock, whose senior managing director Adebayo Ogunlesi sits on OpenAI’s board, saw affiliated funds join Anthropic’s financing, a move TechCrunch describes as “shocking” given the personal connection.

The phenomenon is not merely a matter of diversified portfolios. Venture capitalists traditionally market themselves as “founder‑friendly” partners who protect a startup’s competitive moat, especially when rivals are vying for the same market share. TechCrunch points out that VCs now face a fiduciary dilemma: owning stakes in both OpenAI and Anthropic forces them to balance loyalty to one portfolio company against the broader duty to their limited partners. The conflict is amplified by the fact that many of these investors also sit on the boards of the companies they fund, granting them access to confidential operational data that is not publicly disclosed (TechCrunch). In the OpenAI‑Anthropic case, that data could include product roadmaps, pricing strategies and go‑to‑market plans, raising questions about how investors will manage potential conflicts of interest.

Sam Altman’s own history adds a layer of intrigue. Business Insider, citing documents from the Musk‑OpenAI lawsuit, reports that Altman circulated a list of “rivals”—including Anthropic, xAI and Safe Superintelligence—to OpenAI investors in 2024, warning that non‑passive investments in those firms could trigger a loss of confidential information. Altman later denied that he would bar investors from future OpenAI rounds, but he did acknowledge that “non‑passive investments” would curtail the flow of private data (Business Insider). The fact that many of the same VCs have now placed money in Anthropic suggests that either Altman’s warning was ineffective or that investors are willing to accept reduced access in exchange for exposure to the broader AI upside.

The strategic calculus for the investors appears to be driven by the sheer scale of the markets at stake. Reuters notes that Anthropic’s $30 billion raise pushed its valuation to $380 billion, while OpenAI is reportedly on the cusp of a $100 billion round that would cement its position as the sector’s most valuable private company. With both firms courting enterprise customers, cloud partners and developers, the capital influx is less about picking a single winner and more about ensuring a seat at the table of any future AI infrastructure that dominates the next generation of applications. The overlapping investor base therefore acts as a hedge against the risk that one of the two companies could falter while the other surges ahead.

Industry observers see this as a sign that “loyalty” in Silicon Valley has eroded in favor of portfolio‑wide exposure. Wired’s recent feature on the topic argues that founders once expected investors to act as staunch allies, but today “anyone can be lured away for the right price,” a sentiment echoed by the TechCrunch analysis of the current AI funding climate. As the AI arms race intensifies, the line between strategic partnership and opportunistic diversification blurs, leaving VCs to navigate a landscape where their fiduciary responsibilities may conflict with the very notion of exclusive backing.