AI Investment Loyalty Fades as OpenAI VCs Back Competing Anthropic

As OpenAI nears the close of a fresh $100 billion funding round and Anthropic concludes its own massive $30 billion raise, one reality is starkly apparent: the traditional notion of investor "loyalty" is fraying.

At least a dozen direct investors in OpenAI were recently named as backers in Anthropic’s $30 billion round, including prominent firms like Founders Fund, Iconiq, Insight Partners, and Sequoia Capital.

Some overlap is easier to understand when it involves hedge funds or asset managers whose primary focus remains public equities, competitors or not. This group includes names like D1, Fidelity, and TPG.

One case, however, is more striking. BlackRock-affiliated funds participated in Anthropic's raise despite having senior managing director and board member Adebayo Ogunlesi serving on OpenAI’s board.

In that context, if various BlackRock funds get an opportunity to invest in OpenAI stock, they are likely to seize it, regardless of senior leadership ties. (BlackRock manages a full spectrum of funds, including mutual funds, closed-ends, and ETFs). The complex history between OpenAI and Microsoft, and why Microsoft hedges its bets, is well-known. The same logic applies to Nvidia.

But venture capital funds have historically operated by a different playbook.

VCs market themselves as "founder-friendly" partners, pledging to actively help their portfolio companies succeed, especially against key rivals. If you own stakes in both OpenAI and Anthropic, where does your loyalty ultimately lie, beyond your own limited partners?

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Furthermore, startups are private entities. They routinely share confidential business updates with their direct investors—information not disclosed to the public, unlike public companies. Often, VCs also secure board seats, incurring an additional layer of fiduciary duty to their portfolio companies.

This situation is particularly intriguing given Sam Altman's background. As a former president of Y Combinator, he understands the VC world intimately. In 2024, reports indicated he provided his investors with a list of OpenAI rivals he preferred they not fund, including companies launched by former OpenAI personnel like Anthropic, xAI, and Safe Superintelligence.

Altman later disputed that he threatened to bar investors from future rounds if they backed these rivals. However, according to documents from the Elon Musk vs. OpenAI lawsuit reported by Business Insider, he acknowledged warning that making "non-passive investments" in those companies would result in losing access to OpenAI's confidential information.

The AI sector is shattering conventions due to the unprecedented scale of capital required. The largest AI labs are raising record sums to fuel extraordinary growth and immense data center demands. When the fundraising rounds are this large and the potential returns so significant, who can realistically decline participation?

That said, not all venture investors have crossed this line. Andreessen Horowitz, for example, backs OpenAI but not (yet) Anthropic. Menlo Ventures backs Anthropic but not (yet) OpenAI.

In our research, which we admit is not exhaustive, we identified a dozen investors with direct stakes in only one of the two companies, not both.

Other examples include Bessemer Venture Partners, General Catalyst, and Greenoaks. (Note: We initially asked Claude to compile the list of dual investors. It produced nearly as many errors as correct entries, a reminder that even impressive technology can sometimes be less reliable than an intern's work.)

Nevertheless, as we have reported, the fact that this long-standing principle has been disregarded by some of Silicon Valley's most respected firms, like Sequoia, is significant. One investor we contacted simply shrugged, noting that as long as the firm doesn't hold a board seat, most no longer perceive any harm.

Ultimately, conflict-of-interest policies should become a standard point of inquiry for founders before signing any term sheet, regardless of the investor's prestige.