As OpenAI nears the completion of a new $100 billion funding round and Anthropic concludes its own massive $30 billion raise, it's evident that traditional investor "loyalty" is becoming increasingly rare. Earlier this month, at least a dozen direct investors in OpenAI were also named as backers in Anthropic's $30 billion round, including prominent firms like Founders Fund, Iconiq, Insight Partners, and Sequoia Capital.

Certain dual investments are more understandable when they come from hedge funds or asset managers, whose primary focus often remains public stock investments, regardless of corporate rivalries. Examples in this category include D1, Fidelity, and TPG. However, one case stood out as particularly surprising: affiliated funds of BlackRock participated in Anthropic's raise despite the fact that BlackRock's senior managing director and board member, Adebayo Ogunlesi, also sits on OpenAI's board of directors. In such contexts, if various BlackRock funds have an opportunity to acquire OpenAI stock, they are likely to pursue it, irrespective of senior leadership's personal affiliations. BlackRock manages a wide array of funds, including mutual funds, closed-end funds, and ETFs.

The complex dynamics between OpenAI and Microsoft are well-documented, explaining why Microsoft might diversify its investments, a strategy similarly adopted by Nvidia. Historically, venture capital funds have operated under a different ethos. VCs often promote themselves as "founder-friendly" and "helpful," implying that once they invest in a startup, they commit to supporting its success, especially against key competitors. When an investor holds stakes in both OpenAI and Anthropic, where does their loyalty truly lie, beyond their obligation to their own investors?

Startups, as private companies, typically share confidential business information with their direct investors—details not disclosed to the public as they would be with publicly traded firms. In many instances, VCs also secure board seats, which introduces an additional layer of fiduciary responsibility to their portfolio companies. This situation becomes even more intriguing given that Sam Altman, OpenAI's CEO, hails from a venture capital background as a former president of Y Combinator and is well-versed in industry norms.

In 2024, Altman reportedly provided his investors with a list of OpenAI's rivals he preferred they not support, which largely included companies founded by former OpenAI employees, such as Anthropic, xAI, and Safe Superintelligence. Altman later clarified that he did not threaten to exclude investors from future rounds if they backed these rivals. However, according to documents from the lawsuit between Elon Musk and OpenAI, Altman acknowledged informing investors that if they made "non-passive investments" in these companies, they would no longer have access to OpenAI's confidential business information.

The AI sector is reshaping investment conventions due to the unprecedented scale of funding required, driven by extraordinary growth and immense data center demands. When such vast capital is needed and the potential returns are enormous, few investors can afford to decline participation. Nevertheless, not all venture investors have embraced this dual-investment approach. For example, Andreessen Horowitz supports OpenAI but not Anthropic, while Menlo Ventures backs Anthropic but not OpenAI.

In fact, research indicates a dozen investors appear to have direct investments in only one of these companies, not both. Others in this category include Bessemer Venture Partners, General Catalyst, and Greenoaks. It's worth noting that compiling a precise list of dual investors proved challenging, highlighting that even advanced technology can sometimes produce less reliable results than manual verification.

Ultimately, the fact that this long-standing principle of investor exclusivity has been set aside by highly respected firms like Sequoia is significant. One investor, when questioned, simply shrugged and noted that as long as the firm doesn't hold a board seat, many no longer perceive any harm in such arrangements. Moving forward, conflict-of-interest policies should become a critical point of discussion for founders before signing any term sheet, regardless of the investor's reputation.