When VCs Bet on Both Horses in the AI Race

$100 Billion Changes Everything

At least 12 investors backed both OpenAI's upcoming $100 billion round and Anthropic's recent $30 billion raise. We're talking about Sequoia Capital, Founders Fund, Insight Partners – Silicon Valley's most respected names betting on direct competitors.

This isn't hedge fund behavior where you'd naturally own competing public stocks. These are venture capital firms that have built their reputations on being "founder friendly" and "helpful." So when you own chunks of both OpenAI and Anthropic, who exactly are you helping?

The BlackRock Paradox

The most striking example? BlackRock funds joined Anthropic's raise even though BlackRock's senior managing director Adebayo Ogunlesi sits on OpenAI's board. That's not just dual investing – that's a potential conflict at the highest level.

Sure, BlackRock runs every type of fund imaginable. Their MO has always been "if there's an investment opportunity, we take it." But startups aren't public companies. They share confidential business data with their investors. Board members have fiduciary duties.

Sam Altman's Warning Shot

Sam Altman knows the VC game – he ran Y Combinator. In 2024, he reportedly gave investors a "don't invest" list including Anthropic, xAI, and Safe Superintelligence. Companies founded by OpenAI alumni, naturally.

Altman later denied threatening to bar investors from future rounds. But court documents revealed he did say investors making "non-passive investments" in rivals would lose access to OpenAI's confidential information. That's a clear line in the sand.

The Holdouts Still Exist

Not everyone's playing both sides. Andreessen Horowitz backs OpenAI but not Anthropic. Menlo Ventures chose Anthropic over OpenAI. Bessemer Venture Partners, General Catalyst, and Greenoaks also picked a lane.

One investor we reached out to simply shrugged: "As long as there's no board seat, no one sees the harm anymore." But that casual attitude represents a seismic shift in Valley culture.

When Money Talks Louder Than Loyalty

The numbers are unprecedented. We're talking about $130 billion combined between these two rounds alone. When the potential returns are this massive and the capital needs this extreme, traditional VC loyalty starts looking like a luxury few can afford.

But there's a deeper question here: In an era where AI labs need billions just to stay competitive, is exclusive backing even realistic? Or are we witnessing the birth of a new investment paradigm where hedging isn't betrayal – it's survival?