DealBook: How Anthropic got so big
Also, a scoop on an audio merger now on ice.
DealBook
May 29, 2026

Good morning. Andrew here. Anthropic is now more valuable than OpenAI, something Silicon Valley wouldn’t have expected a year ago. We go behind the numbers — and outline the risks the new leader in A.I. faces.

Also: Lauren Hirsch has a scoop on deal talks between iHeartMedia and SiriusXM, which were put on pause. And Dell’s stock is flying, raising new questions about President Trump’s investments in the computer giant. (Was this newsletter forwarded to you? Sign up here.)

An urban building draped in large panels that say, “Claude. Keep thinking.”
Anthropic, which created the Claude A.I. model, has surged in popularity with users, pushing its valuation to $900 billion. Jason Henry for The New York Times

The numbers behind Anthropic’s rise

A year ago, the biggest and buzziest artificial intelligence start-up around was undoubtedly OpenAI. That’s no longer the case.

Anthropic has taken that crown with its $65 billion fund-raising round. How the company went from also-ran to 900-pound gorilla is a reflection of the current state of the A.I. race, and it raises questions about what comes next.

Where things stand: Anthropic is valued at $900 billion, while OpenAI was last valued at $730 billion, not including the $122 billion it had just raised.

Behind Anthropic’s ascent: The company’s Claude models were consistently highly regarded. But by November, Anthropic’s Claude Code programming tool had become exponentially better at automating software development, driving a surge in adoption.

Its models have continued to improve rapidly — and its Mythos model has proved so adept at uncovering cybersecurity vulnerabilities that it has spooked governments and companies around the world.

Here are three data points that help explain Anthropic’s leapfrogging OpenAI in valuation:

Anthropic’s revenue run rate — an extrapolation of projected annual revenue, based on a month’s financial performance — has jumped from $4 billion last July to $9 billion at the end of last year to $30 billion last month to $47 billion now. By contrast, OpenAI implied in March that its revenue run rate was about $24 billion; and The Information reported this week, citing unnamed sources, that the figure had risen just north of $30 billion. (Of note: OpenAI has disputed Anthropic’s revenue calculations in the past.)

Anthropic’s market share on OpenRouter, a platform that allows customers to dynamically switch between A.I. models, has outpaced OpenAI’s for many of the past 18 months. (Note: Tokens are the basic units of A.I. use.)

A line chart shows a comparison between Anthropic and OpenAI as they vie for a share of the A.I. token market.

Anthropic has just outpaced OpenAI in business adoption, too, per Ramp, a provider of business billing and expense services:

A line chart shows a comparison between Anthropic and OpenAI as they vie for a share of corporate A.I. subscriptions.

But Anthropic’s lead could easily evaporate:

The stakes are huge. Anthropic and OpenAI are racing toward potentially trillion-dollar I.P.O.s this year, giving them the ability to raise billions from public-market investors after seemingly maxing out the private markets.

Both companies are worried that there’s a finite amount of investor money for those offerings — and each wants to be the one that people bet on.

HERE’S WHAT’S HAPPENING

A mushroom cloud from the explosion of a New Glenn rocket on the left of the frame.
A screen grab of a video posted by an X user shows the explosion of a Blue Origin rocket on Thursday night.  @JConcilus on X, via Agence France-Presse

A Blue Origin rocket explodes on its launchpad. A New Glenn rocket from Jeff Bezos’ space company, which had been set to carry satellites for Amazon’s internet service, exploded during a test of its engines on the launchpad. Repairs of the damage caused by the explosion of the rocket, named after the astronaut John Glenn, will probably take months and affect NASA’s plans to land people on the moon in 2028.

Oil traders cheer apparent progress on a peace deal. Brent crude, the international benchmark for oil, dropped to around $91 a barrel, on pace for its biggest monthly decline since 2020, as U.S. officials said they were moving closer to an agreement with Iran. Details for the reported framework, including the future of the Strait of Hormuz, are still being hammered out.

Mayor Zohran Mamdani announces New York City’s version of DOGE. City Hall will form a Commission of Government Efficiency, or COGE, to find ways to use public funds more effectively, Mamdani wrote on social media. The project was endorsed by Jeff Bezos, who suggested that some of the cost savings could be used to eliminate taxes on the bottom half of the city’s earners.

Scoop: SiriusXM and iHeartMedia put deal talks on ice

Early-stage talks over a potential sale of iHeartMedia to SiriusXM, which would create an audio giant, have stalled after the two sides were unable to come to terms, two people with knowledge of the discussions told Lauren Hirsch.

The sources, who were not authorized to speak about the negotiations, said that the talks could always be revived. But a big question now is what each company’s stand-alone strategy looks like as digital giants like Spotify continue to disrupt the audio industry.

There’s a long history between the two companies. Liberty SiriusXM Group, once an affiliate of John Malone’s media empire, used to hold significant stakes in both companies. Liberty SiriusXM eventually sold its stake in iHeartMedia (primarily a broadcast radio company) and split off its ownership of SiriusXM (primarily a satellite radio company) into a separate entity.

Word of a potential deal, which was meant to help offset the deterioration of traditional radio businesses, first emerged last month.

Both companies are focused on podcasts as a point of growth:

  • IHeartMedia’s podcast business, which includes “Las Culturistas” and “Stuff You Should Know,” collected $147 million in revenue in the first quarter, up 27 percent year on year. It has also pushed further into video podcasts, including through a partnership with Netflix. Its overall revenue came in at $884 million for the quarter, a 9.6 percent jump.
  • Sirius has signed deals for programs including “Call Her Daddy,” Alex Cooper’s hit show, and “SmartLess.” It has also focused on exclusive content, including by renewing Howard Stern’s contract for another three years.
President Trump shaking Michael Dell's hand in the White House.
Michael Dell, the founder of Dell Technologies, and President Trump at the White House last year. The company’s stock market run has bolstered the fortunes of both men. Doug Mills/The New York Times

Dell’s surge puts scrutiny on Trump

The computer company Dell Technologies has been on some run — and that’s especially good news for its founder, Michael Dell, and one of his biggest supporters, President Trump.

That raises questions about Trump’s relationship with the company, which just won a big government contract, even as the White House argues that his personal purchases of Dell stock are on the up and up.

The latest: Dell just reported blowout earnings. Its shares are up a staggering 40 percent in premarket trading this morning as investors cheer its artificial-intelligence-fueled growth forecast.

Dell told analysts yesterday that it would sell $60 billion worth of computer servers this year to hyperscalers and other companies that are investing heavily in the A.I. boom.

Dell is one of the biggest gainers on the S&P 500 this year. The surge has pushed Michael Dell’s net worth near $200 billion, according to Bloomberg.

A line chart shows the share performance for Dell since Inauguration Day last year.

But that’s not what’s raising eyebrows.

Trump has profited, too. Recent filings show that the president bought between $1 million and $5 million in Dell stock in February, and smaller amounts since.

That’s made Dell’s stock market performance another proxy for how much Trump has personally gained from his many business deals while in office. It’s also alarmed watchdogs who see the mingling of politics and business — including yesterday’s announcement that the government will pay Dell $9.7 billion to equip the Defense Department, U.S. Coast Guard and the intelligence community with Microsoft software and services.

The Pentagon contract put the potential conflict-of-interest problem back in the spotlight. “It looks terrible is the short answer,” Greg Williams, director of the Center for Defense Information, part of the Project on Government Oversight, told CNBC.

The Trump family has argued that the president has no say in his stock trades, and that they are executed by brokerage firms.

Trump and Dell’s fortunes have become intertwined lately. Michael and Susan Dell are at the center of Trump accounts, having pledged $6.25 billion to help capitalize the new investment accounts that are a key feature of Trump’s giant 2025 spending law. Dell courted Trump early in the president’s second term, and Trump has become a big fan.

Trump hasn’t just bought Dell stock. “Go out and buy a Dell computer,” he told his followers at an event in Georgia in February.

Scott Bessent holds up a printout of an article with an image of money.
Treasury Secretary Scott Bessent holding an article about a $250 bill featuring a portrait of President Trump.  Evan Vucci/Reuters

Photo of the day: Trump money

Treasury Secretary Scott Bessent confirmed yesterday that his department was preparing a mock-up of a $250 bill featuring President Trump’s portrait. Issuing one would require congressional approval, as a federal law from 1866 stipulates that only a “deceased individual” may appear on U.S. currency.

Another potential issue: Law enforcement and economists worry that large-denomination bills are favored by organized crime.

A chat bubble that reads, "How do you use AI? What are your best use cases?" The bubble underneath indicates a pending response.

Talking A.I. with the C.E.O. of LabCorp

Every week, we’re asking a leader how he or she uses artificial intelligence. This week, Adam H. Schechter, who leads the medical testing and health care company LabCorp, told Sarah Kessler that he had built an A.I. agent to scope out World Cup games. The interview has been condensed and edited for clarity.

How do you personally use A.I.?

There are two places where I could see World Cup games, and I want to know where the better games are, based on who wins the first round. How do I know when the tickets are hitting a floor price? I have an A.I. agent that is doing all the work for me.

How has A.I. changed your business?

We just launched an app where you can look at your test results in a very easy-to-understand format. You can ask any question through an A.I. chat.

We also have a tool to help with lab-test search. If you’re a physician with a patient who has a disease that’s a bit more rare, trying to figure out which of 6,500 tests would be most appropriate can be difficult. Now you can just have a natural conversation with it.

What opportunities do you see in the longer term?

Historically, you’ve had pathologists in every lab, and they’ll have to prepare and look at the slides. If the stain that they use on the slide isn’t correct, they’ve got to get another piece of tissue.

In the future, with A.I., you’ll be able to apply the stain digitally so you’re not using the tissue. And if that stain’s wrong, you’ll be able to wipe it off digitally and not need another piece of tissue. It will be completely transforming.

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THE SPEED READ

Deals

  • SpaceX is said to have trimmed the valuation target for its I.P.O. to at least $1.8 trillion, from more than $2 billion. (Bloomberg)
  • Tilman Fertitta, a billionaire and the U.S. ambassador to Italy, has agreed to buy the casino operator