With AI, investor loyalty is (almost) dead: at least a dozen OpenAI VCs now also back Anthropic 

With OpenAI on the verge of finalizing a new $100 billion round, and Anthropic just closing its own monster $30 billion raise, one thing is clear: the concept of investor “loyalty” is only hanging on by a thread. 

At least a dozen direct investors in OpenAI were announced as backers in Anthropic’s $30 billion raise earlier this month, including Founders Fund, Iconiq, Insight Partners, and Sequoia Capital. 

Some dual investments are understandable if they come from the hedge fund or asset manager worlds, where their focus is still largely investing in public stocks (competitors or not). These include D1, Fidelity, and TPG.  

One of these was a bit shocking. Affiliated funds of BlackRock joined in Anthropic’s $30 billion raise even though BlackRock’s senior managing director and board member Adebayo Ogunlesi is also on OpenAI’s board of directors. 

In that world, it’s true that if various BlackRock funds get a chance to own OpenAI stock, they are likely to take it, never mind the personal association of a member of their senior leadership. (BlackRock runs every type of fund, including mutuals, closed-ends, and ETFs).  And we all know the history of OpenAI and Microsoft’s relationship and why Microsoft is hedging its bets. Ditto for Nvidia. 

But venture capital funds have — until now — operated differently.

VCs market themselves as “founder friendly” and “helpful,” the idea being that when a VC firm buys a chunk of a startup’s company, the investor will help that startup be successful, particularly against its major 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 information with their direct investors on their business status — data that isn’t disclosed publicly the way it is with public companies. In many cases, the VCs also take board seats, which carries another level of fiduciary responsibility to their portfolio companies. 

What makes this particular case even more interesting is that Sam Altman comes from the world of venture capital, 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. It largely included companies launched by folks who left OpenAI, including Anthropic, xAI, and Safe Superintelligence. 

Altman later denied that he told OpenAI investors they would be barred from future rounds if they backed his list of perceived rivals. Altman 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, Business Insider reported. 

AI is also breaking the mold because of the record-breaking amounts of money that the largest AI labs are raising as they experience never-before-seen growth (and never-before-seen data center needs). At some point, when the hat is being passed around, the needs are so great and the possibilities of returns are so large, who can be expected to say no? 

It turns out that not all venture investors have yet slid down the slippery slope. Andreessen Horowitz backs OpenAI but not (yet) Anthropic. Menlo Ventures backs Anthropic but not (yet) OpenAI, for instance.

In fact, in our admittedly not exhaustive research, we found a dozen investors that appear to only have direct investments in one of these companies, not both. 

Others include Bessemer Venture Partners, General Catalyst, and Greenoaks. (Note: we originally asked Claude to give us the list of dual investors. It got almost as many entries wrong as it got right, so all this for a very cool tech whose work sometimes remains less trustworthy than an intern’s.)

Still, as we previously reported, the fact that this longstanding rule has been tossed by some of the most respected firms  in the 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.  

Still, conflict-of-interest policies should now become another thing that founders ask about before signing that term sheet, no matter who it’s from.