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The Briefing
OpenAI on Monday had good news and bad news for the media corps that avidly follows its every twist and turn. ͏ ‌     ­͏ ‌     ­͏ ‌     ­͏ ‌     ­͏ ‌     ­͏ ‌     ­͏ ‌     ­͏ ‌     ­͏ ‌     ­͏ ‌     ­͏ ‌     ­͏ ‌     ­͏ ‌     ­͏ ‌     ­͏ ‌     ­͏ ‌     ­͏ ‌     ­͏ ‌     ­͏ ‌     ­͏ ‌     ­͏ ‌     ­͏ ‌     ­͏ ‌     ­͏ ‌     ­͏ ‌     ­͏ ‌     ­͏ ‌     ­͏ ‌     ­͏ ‌     ­͏ ‌     ­͏ ‌     ­͏ ‌     ­͏ ‌     ­͏ ‌     ­͏ ‌     ­͏ ‌     ­͏ ‌     ­͏ ‌     ­͏ ‌     ­͏ ‌     ­͏ ‌     ­͏ ‌     ­͏ ‌     ­͏ ‌     ­͏ ‌     ­͏ ‌     ­͏ ‌     ­͏ ‌     ­͏ ‌     ­͏ ‌     ­
Jun 8, 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!

OpenAI on Monday had good news and bad news for the media corps that avidly follows its every twist and turn. The good news is that it filed confidentially to go public, a week after Anthropic did the same thing. (Yippee!) The bad news: OpenAI said it has “not decided on timing yet” and “it may be a while because there are things we want to do that are likely easier as a private company.” Moreover, it announced the confidential filing only because “we expect it to leak.” 

In other words, don’t get your hopes up. We might see a fall contest between the two AI firms. Then again, maybe we won’t. 

Meanwhile, on a separate news front entirely, no one is ever going to accuse Apple of getting ahead of its users on AI. The company showed off its long-awaited AI overhaul of Apple’s Siri digital assistant on Monday, as its Worldwide Developers Conference kicked off, and it was a little underwhelming. 

To be sure, the new Siri is better than it was before—but let’s face it, the bar was low. More importantly, the “new” AI features Apple showed off were essentially catching up to what’s available elsewhere, from Google and the like.

For instance, Mike Rockwell, who oversees Siri engineering, showed off how he could ask Siri for the date of an upcoming concert and for information on getting tickets. He asked Siri to set a reminder so he could sign up for a ticket lottery. Other tech companies might have shown off a feature that ensured Siri signed up for the tickets on its own. Then again, given that agentic shopping features—where an app does something on behalf of a consumer—are still evolving, Apple may be right not to overpromise (after all, overpromising on AI has burned it in the past).

Apple’s software chief Craig Federighi, who emceed the keynote, went out of his way to take a shot at other tech companies’ aggressive approach to AI. “Some appear to be racing forward, seemingly pursuing AI for the sake of AI, without clear regard for the people—all of us—that it’s ultimately meant to serve,” he said (who could he be talking about?). That’s not Apple’s way, he added. Federighi, as we reported here, was long a skeptic of AI. While he has supposedly found religion regarding the technology, his continuing caution is somewhat refreshing. 

Aside from the unproven nature of many new AI services, there’s plenty of evidence that ordinary people are wary about its benefits and risks. Other big tech firms, such as Google and Amazon, have moved carefully to overhaul their core services for AI, presumably not wanting to upset their hundreds of millions of users with too-rapid shifts. Still, for all of Apple’s caution, it’s following a familiar playbook—ensuring that those customers who do want AI will have to spend money to get it.

The new Siri AI features will require the iPhone 15 Pro or later, so that shuts out anyone with a phone more than three years old. More egregiously, buried in the footnotes of one of Apple’s press releases was the revelation that the iPhone 17 Pro or iPhone Air or later will be needed for “Apple’s most powerful on-device model and the features it enables, like expressive voices and more advanced dictation.” (Hat tip to 9to5Mac for pointing that out.) Some AI features also will have “daily usage limits” that will require iCloud subscriptions to get past.

You might think Apple is banking on these features to drive an upgrade cycle. But given how tentatively it is dipping its toes into the AI waters, it’s doubtful the company expects  AI to do anything for it in the near term. 

Apple had so many people grabbing a piece of the WWDC keynote presentation that those from the company’s 166,000-strong workforce who weren’t included could feel disappointed—except for the fact that the most important person at Apple also did not make an appearance.

Yes, a noticeable absentee from the presenter lineup was incoming CEO John Ternus. The reason is perhaps obvious: He takes the role on Sept. 1 and presumably didn’t want to upstage retiring CEO Tim Cook. Ternus will be in the office in time to host the annual iPhone unveiling typically held in early September.

There is money to be made from those digital cast-offs. That’s the message from the IPO filing of Italian conglomerate Bending Spoons, which became public on Monday. Bending Spoons, as you might recall, has made a habit of buying up aging tech businesses, including AOL, Eventbrite and Vimeo.

It turns out some of these companies were quite profitable. Take AOL, which had operating profit last year of $333.6 million on $633.4 million in revenue. Several years of ownership by private equity firm Apollo seems to have done wonders for the pioneering internet access firm. Bending Spoons paid $1.45 billion for AOL, which seems a reasonable deal given the business’s profitability. (Notably, AOL’s revenues grew slightly in 2025, as Bending Spoons’ IPO filing showed.)

Bending Spoons itself is also profitable, although as the acquisitions of AOL and Eventbrite were only completed this year, we’ll have to wait a while to see how its finances shake out. (For the first quarter, revenue more than doubled and the company reported a profit.) The company isn’t likely to get on anyone’s list of growth stocks, but for value investors, it might appeal!

• Nvidia and SK Hynix have signed a multiyear deal to work together on advanced memory chips, as AI demand strains global memory supply. The agreement covers chip design and manufacturing, and it includes memory for Nvidia’s Vera Rubin platform, its next major AI system.

Check out today’s episode of TITV in which we unpack the attention on recursive self-improvement in AI.

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