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The Briefing
The poor souls responsible for technology buying decisions at companies must be overwhelmed these days.͏ ‌     ­͏ ‌     ­͏ ‌     ­͏ ‌     ­͏ ‌     ­͏ ‌     ­͏ ‌     ­͏ ‌     ­͏ ‌     ­͏ ‌     ­͏ ‌     ­͏ ‌     ­͏ ‌     ­͏ ‌     ­͏ ‌     ­͏ ‌     ­͏ ‌     ­͏ ‌     ­͏ ‌     ­͏ ‌     ­͏ ‌     ­͏ ‌     ­͏ ‌     ­͏ ‌     ­͏ ‌     ­͏ ‌     ­͏ ‌     ­͏ ‌     ­͏ ‌     ­͏ ‌     ­͏ ‌     ­͏ ‌     ­͏ ‌     ­͏ ‌     ­͏ ‌     ­͏ ‌     ­͏ ‌     ­͏ ‌     ­͏ ‌     ­͏ ‌     ­͏ ‌     ­͏ ‌     ­͏ ‌     ­͏ ‌     ­͏ ‌     ­͏ ‌     ­͏ ‌     ­͏ ‌     ­͏ ‌     ­͏ ‌     ­
Jun 2, 2026

The Briefing

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Thanks for reading The Briefing, our nightly column where we break down the day’s news. If you like what you see, I encourage you to subscribe to our reporting here.


Greetings!

The poor souls responsible for technology buying decisions at companies must be overwhelmed these days. Not only does seemingly every other tech firm want to send consultants—invariably calling themselves forward-deployed engineers as though they’re on maneuver in the desert—to help companies learn how to use their AI services, but the array of AI product choices seems to grow daily. 

On Tuesday, for instance, OpenAI held an event in New York to pitch new AI tools for businesses, including some designed for specific sectors, such as equity trading and investment banking. Also on Tuesday, Microsoft announced at its own event in San Francisco new hardware specifically designed for AI, including a desktop computer and AI models for businesses. While Microsoft is an old hat at serving businesses, OpenAI’s event was a reminder of how important the enterprise AI market is for younger AI firms (and it’s a market that OpenAI’s rival Anthropic is perceived to dominate). 

OpenAI Chief Revenue Officer Denise Dresser and other OpenAI staffers spoke before an audience that—judging from the video livestream—appeared to be composed mostly of older men wearing suits, quite the contrast to the hoodie-wearing crowd you typically see at these OpenAI events. Dresser sucked up to the New Yorkers in the room, observing that New York was a city in which “some of the most legendary companies” have gotten their startup. She also got BNY CEO Robin Vince up on the stage to discuss AI. (For our recent profile of Dresser, see here.)

It’s hard to say how much luck OpenAI will have selling these new tools to businesses, given the sheer competition it faces from Anthropic (which rolled out some of its own sector-specific tools a little while ago), Google, Microsoft and many enterprise software firms and AI startups. Still, OpenAI says enterprise-related revenue accounts for 40% of its top line now, which perhaps is more than people might realize given how much attention its consumer-focused chatbot gets. 

On that point, OpenAI is following in Google’s steps and blurring the lines between its different apps. The company is promoting its Codex coding app as a tool that lots of people, not just developers, can use to “automate routine work” and other tasks. On Tuesday it also reiterated its plans to combine Codex with ChatGPT—for the backstory on that move, see here. On today’s livestream, CEO Sam Altman mentioned that he’d heard from customers they weren’t always sure which to use. 

Altman also emphasized OpenAI’s intention to keep pushing down the cost of using its AI products. As we’ve written, the cost of AI has become a sore point for many businesses, something Altman may win brownie points by acknowledging. Anthropic, you’re on notice!

After weeks of off-and-on discussions, President Donald Trump on Tuesday suddenly signed an executive order designed to allay concerns over the cybersecurity threats posed by AI models. 

But he did so in private, quite the contrast to the public ceremony—to be attended by tech CEOs—planned for last month before its last-minute cancellation.

The hush-hush ending to the saga over the executive order reflects a fraught process that saw factions within the White House arguing over a new approach to regulation.

The final order does not depart meaningfully from the draft order whose details were widely leaked over the past month, including in our report in May. The language makes it clear that compliance with the order is voluntary. It even specifies that nothing in the order “shall be construed to authorize the creation of a government licensing” system—just in case anyone thought that’s what was going on. 

Still, the biggest fear for tech companies (along with former AI and crypto czar David Sacks, who convinced Trump to bail on the earlier version) concerned language that would ask AI developers to provide the government with access to frontier models “up to 90 days” before releasing them. The new version changes this language to 30 days. 

Otherwise, the order is dedicated to bulking up the government’s cyberdefense systems, including forming an “AI cybersecurity” clearinghouse between government agencies and AI companies to scan for software vulnerabilities. For now, all eyes will be on a new ticking clock: The administration has given itself 60 days to develop a framework for identifying which frontier models will be (albeit voluntarily) subject to the order, as well as figuring out which “trusted partners” aside from the government will have earlier access to models. 

The final accord was the result of a White House meeting on Monday between Trump, Treasury Secretary Scott Bessent, and National Cyber Director Sean Cairncross, among others, who were pushing to get the order across the finish line and dialed in Sacks to reach a final agreement, according to people familiar with the matter. As ever-evolving AI models pose new threats at a speed faster than government, however, this uneasy White House coalition will have a bumpy road ahead.—Leo Schwartz

• SpaceX is negotiating to pay the banks working on its potentially record-breaking IPO a smaller than normal slice of the proceeds, Bloomberg reported on Tuesday.

• SK Hynix plans to double its memory chip capacity within five years as AI demand keeps straining global supply, Bloomberg reported. The expansion can ease one of the biggest hardware constraints facing AI data centers.

• Shopify said Tuesday that it would expand its share buyback authorization by $3 billion to a total authorization of $5 billion, becoming the latest software firm to unveil expanded share repurchase plans as AI fears have battered stock prices.

• Anthropic is quadrupling the number of companies allowed to use its Claude Mythos model for cybersecurity testing under its Project Glasswing initiative.

Check out today’s episode of TITV in which we speak with CrowdStrike’s former chief product officer about why Anthropic’s Mythos model doesn’t scare him.

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