OpenAI is on the verge of finalizing a new $100 billion funding round, and Anthropic just closed its own monumental $30 billion raise. One thing is clear: the concept of investor loyalty is hanging on by a thread. At least a dozen direct investors in OpenAI were announced as backers in Anthropic’s recent raise, including Founders Fund, Iconiq, Insight Partners, and Sequoia Capital.
Some dual investments are understandable when they come from the hedge fund or asset manager world, where the focus remains largely on public stocks. These include firms like D1, Fidelity, and TPG. One case was particularly striking. Affiliated funds of BlackRock joined Anthropic’s raise even though BlackRock’s senior managing director and board member, Adebayo Ogunlesi, also sits on OpenAI’s board. In that world, if various BlackRock funds get a chance to own OpenAI stock, they are likely to take it, regardless of the personal association of a senior leader.
We all know the history of the OpenAI and Microsoft relationship and why Microsoft is hedging its bets. The same goes for Nvidia. But venture capital funds have, until now, operated differently. VCs market themselves as founder-friendly and helpful, with the idea that when a firm buys a chunk of a startup, the investor will help that startup succeed against its rivals. If you are an owner of both OpenAI and Anthropic, who does your loyalty belong to, besides your own investors?
Additionally, startups are private companies. They typically share confidential business information with their direct investors, data that isn’t publicly disclosed. In many cases, VCs also take board seats, which carries another level of fiduciary responsibility to their portfolio companies.
What makes this case more interesting is that Sam Altman comes from the venture capital world as a former president of Y Combinator. He knows the drill. In 2024, he reportedly gave his investors a list of OpenAI’s rivals that he didn’t want them to back, largely including companies launched by former OpenAI employees, such as Anthropic, xAI, and Safe Superintelligence. Altman later denied that he told investors they would be barred from future rounds if they backed these rivals. He did admit that he said if they made non-passive investments, they would no longer receive OpenAI’s confidential business information, according to documents in the lawsuit between Elon Musk and OpenAI.
AI is also breaking the mold because of the record-breaking amounts of money the largest labs are raising, fueled by unprecedented growth and massive data center needs. When the hat is being passed around, the needs are so great and the potential returns so large, who can be expected to say no?
It turns out not all venture investors have slid down this slope. Andreessen Horowitz backs OpenAI but not Anthropic. Menlo Ventures backs Anthropic but not OpenAI. In our research, we found a dozen investors that appear to have direct investments in only one of these companies, not both. Others include Bessemer Venture Partners, General Catalyst, and Greenoaks.
Still, the fact that this longstanding rule has been tossed by some of the most respected firms in Silicon Valley, like Sequoia, is notable. One investor we reached out to simply shrugged and said that as long as the firm doesn’t have a board seat, no one sees the harm in it anymore. Conflict-of-interest policies should now become another thing that founders ask about before signing a term sheet, no matter who it’s from.