Anthropic Is Now Beating OpenAI at Its Own Game

The Courtroom Win That Changes Nothing

OpenAI walked out of an Oakland courtroom on May 19 with a clean legal verdict. A jury took just two hours to find that Elon Musk's lawsuit against the company had been filed too late, and the judge agreed in a matter of minutes. Musk's ambitious ask, that OpenAI revert to nonprofit status and return $134 billion to that entity while removing Sam Altman and Greg Brockman, went nowhere.

On paper, this is a significant win. In practice, it may be the least of OpenAI's problems right now.

As Neeta argues in this episode, the more consequential question is not what happened in the courtroom but what happens on the way to an IPO. And on that front, the picture is considerably messier.

The Trial Did What Musk May Have Intended

Whether or not Musk expected to win, the lawsuit generated something valuable for a competitor: noise. Testimony from Sam Altman, former CTO Mira Murati, and others surfaced real questions about the accuracy of statements made by OpenAI's leadership and the original intent behind the nonprofit's founding. Greg Brockman's conduct drew particular scrutiny.

The collateral damage is measurable. The House Oversight Committee has now opened an inquiry into Sam Altman's approximately $2 billion in stakes across companies with ties to OpenAI. Congressional scrutiny is precisely what a company does not want when it is trying to file for a public offering and convince institutional investors to take a long position.

Add to that reporting from The Wall Street Journal that OpenAI has missed investor targets on both revenue and user growth, and the company's own CFO saying as recently as mid-2025 that the company was not ready for an IPO, and the legal victory starts to feel like a sideshow.

Anthropic Is No Longer the Underdog

Here is the genuinely surprising development at the center of this episode: Anthropic has overtaken OpenAI.

Not in funding history. Not in brand recognition. But in the metrics that actually matter to public market investors. According to data from Ramp cited in The Wall Street Journal, more than 34% of U.S. businesses are now using Anthropic's products, compared to 32.3% for OpenAI. Valuation charts from PitchBook and the Financial Times show Anthropic pulling ahead for the first time. And reporting suggests Anthropic's revenue is stronger, with a broader enterprise customer base, which is widely regarded as the more durable business model.

Anthropic is reportedly targeting an October IPO and seeking to raise another $30 billion, which would put its valuation close to $900 billion. That is a striking figure for a company that did not exist before COVID.

OpenAI, meanwhile, was founded in 2015 and has a significant head start in public consciousness. Yet the momentum indicators are now pointing in a different direction.

A $3 Trillion Question

Step back and the scale of what 2026 is setting up becomes almost difficult to process. OpenAI, Anthropic, and SpaceX, if all three reach public markets, would collectively represent roughly $3 trillion in valuations. That would make this one of the most consequential IPO years in market history.

Cerebras, the chip company trying to compete with Nvidia, went public last week and popped 70% on day one before falling 10% the next day. That kind of volatility is a useful preview of what retail investors may face with much larger and more complex AI companies.

SpaceX is reportedly eyeing a June 12 debut at a valuation between $1.25 and $1.75 trillion, with governance structures that give its CEO effectively unchecked control. Nasdaq rule changes mean all three AI giants could enter major indices far sooner than has historically been standard, which means index fund holders may find themselves owning these stocks whether or not they have done their own due diligence.

What Comes Next

The OpenAI trial is over. The IPO race is not. OpenAI still has a path to a 2026 offering, but the window is narrowing and the list of unresolved issues is long. Anthropic, for its part, has turned a structural advantage in enterprise revenue into a genuine valuation lead, and October is not far away.

For investors, the framing that matters is not who wins the AI race in some abstract sense. It is whether these valuations will hold in public markets where quarterly earnings, governance standards, and competitive dynamics all apply. The private market enthusiasm for AI has been extraordinary. The public market test is about to begin.