When 90 venture capital firms decided not to choose between OpenAI and Anthropic — but to invest in both — it wasn’t indecision. It was an entirely new investment philosophy. “It’s like you wouldn’t pick between Pepsi and Coke,” one VC partner said, voicing the industry’s open secret.
An Unprecedented Number
On June 5, 2026, WIRED published an analysis based on PitchBook data that revealed a startling fact: approximately 90 venture capital firms and other money managers have invested in both OpenAI and Anthropic over the past few years.
To put this in perspective, OpenAI shares about 42 percent of its overall investors with Anthropic. Conversely, roughly a third of Anthropic’s investors are also OpenAI backers. The overlap list reads like a who’s who of venture capital: Sequoia Capital, Greylock, Founders Fund, Redpoint Ventures, Emerson Collective, and Asound Ventures.
Just last week, Anthropic announced a new funding round naming 31 investors — at least 13 of whom already have stakes in OpenAI, according to PitchBook data and WIRED reporting. The number of common investors may actually be an undercount, because collecting information about private investments is notoriously difficult. WIRED identified at least a couple of investors present on Anthropic’s roster but missing from OpenAI’s entry in the PitchBook data, including Amazon.
For two fierce competitors that began their fundraising within a couple of years of each other and are now going head-to-head in the AI capability race, this degree of investor overlap is “unusual, or even unprecedented” — a judgment shared by three experts on the venture capital industry interviewed by WIRED.
AI Pulse View: This isn’t just a curious overlap statistic. A 42 percent shared investor rate sends a clear signal: the smartest capital has stopped believing the AI race is a winner-take-all game. They don’t know who will win, so they’ve decided not to choose.
A Structural Shift in VC Logic
Kyle Stanford, director of venture capital research at PitchBook, told WIRED something worth unpacking:
“The ownership structure you are seeing right now is a real insight into how sophisticated investors are viewing this market, and the answer seems to be that few are convinced this will be a winner-take-all market, or if it is, who the dominant player will be.”
“Rather than looking at these companies as overlapping technologies, what these large investors are doing is protecting their ability to create returns.”
This cuts to the core of what’s happening. Traditional VC logic is: find the company most likely to win in an emerging sector, place a big bet, and wait for the return. But the AI industry is breaking that model.
First, AI market uncertainty exceeds anything seen before. No investor can say with confidence whether the eventual winner will be OpenAI, Anthropic, Google, Meta, or someone else. Model capability iterations are moving too fast, commercialization paths are too varied, and regulatory directions remain unclear. In this environment, “select all” becomes the most rational strategy.
Second, AI companies are raising unprecedented sums. Both OpenAI and Anthropic have raised tens of billions of dollars, with valuations exceeding $852 billion and $900 billion respectively. This means that even a small equity stake could transform a VC fund’s returns. The cost of missing out on either company is simply too high.
Third, the AI competitive landscape is shifting from monopolar to multipolar. While OpenAI and Anthropic get the most attention, Google, Meta, Amazon, and Microsoft are all competing in their own ways. Investors holding positions in both OpenAI and Anthropic are essentially going long on the entire AI sector, not betting on a single company.
AI Pulse View: “Not picking a side” is itself a choice. The VC industry is voting with real money: the AI sector’s ultimate winner has not yet emerged — or perhaps there simply won’t be a single one. This “bet on the entire field” strategy is an admission that the competitive intensity and uncertainty of the AI industry have exceeded traditional VC models’ predictive capacity.
Anthropic’s Latest Round and Industry Frenzy
Just a week before WIRED’s analysis, Anthropic completed a funding round of at least $30 billion at a post-money valuation exceeding $900 billion — which, if closed as expected, would make Anthropic the most valuable company in the AI industry, surpassing OpenAI’s $852 billion March valuation.
The 31-investor list from that round is itself a microcosm of the industry. At least 13 of those investors already had positions in OpenAI. In other words, when Anthropic came knocking for funding, OpenAI’s shareholders were practically lining up to get in.
Even more telling is a change in the San Francisco real estate market. WIRED’s Uncanny Valley podcast reported a detail that borders on surreal: some property leases in San Francisco are now accepting Anthropic stock as payment — “worth more than cash.” When an unlisted company’s equity starts being used as hard currency in real-world transactions, what does that mean?
It means AI industry capital has overflowed normal investment channels, creating a self-sustaining ecosystem. In this system, the boundaries between valuations, equity, options, and cash flow are blurring.
AI Pulse View: When an unlisted company’s stock can pay rent, we’ve entered an entirely new financial narrative. It recalls certain scenes before the 2000 dot-com bubble — except AI companies are generating real, enormous revenue. Anthropic’s annual recurring revenue has crossed $44 billion. This isn’t a bubble; it’s a new valuation paradigm.
Investor Silence, Industry Noise
WIRED reached out to both OpenAI and Anthropic for comment on the investor overlap phenomenon. Neither company responded. Multiple VC firms that invested in both also declined or did not respond to WIRED’s interview requests. Only a few agreed to speak, and only on the condition of anonymity to avoid jeopardizing industry relationships.
This silence is itself a signal. At the noisiest moment in the AI industry, the capital side has chosen the quietest posture.
One anonymous investor told WIRED: “This is an extremely sensitive competitive environment. Every investor is carefully maintaining relationships with multiple companies. Speaking publicly about your investment thesis could be interpreted as taking sides.”
AI Pulse View: The silence from VC firms reflects an AI industry that has entered a “don’t want to offend anyone” phase. Investors need to maintain good relationships with OpenAI, Anthropic, Google, Meta, and others simultaneously, because nobody knows who will dominate the next round. This “multilateral diplomacy” investment strategy is itself a sign that the industry has not yet settled.
The Bigger Picture: AI Capital Is Rewriting the Rules
Ninety VC firms investing in both OpenAI and Anthropic — this number isn’t just an investment pattern. It’s a snapshot of how the AI industry is reshaping the entire capital market.
When AI company valuations approach a trillion dollars, when unlisted company equity is used to pay rent, when the smartest investors choose “bet on the field” instead of “pick a winner” — we are witnessing the birth of a new financial narrative.
The core of this narrative is not technology. It’s capital’s response to technological uncertainty. The AI industry’s capability iterations are too fast, commercialization paths too varied, competitive landscape too multipolar for the traditional “pick a winner” investment strategy to remain viable.
AI Pulse View: Ninety VCs investing in both OpenAI and Anthropic is essentially saying: “We don’t know who will win, but we’re certain this sector will.” This is an entirely new investment philosophy — don’t make a choice, because choosing means excluding possibility. In the AI industry, possibility is more valuable than certainty.
For ordinary founders and developers, this signal matters too: the AI race is far from over, a multipolar structure is forming, and new players still have a shot. Capital is pricing in this uncertainty — and that is precisely the soil in which innovation grows.