Apple, Siri, and the booted blogger: A Conversation with John Gruber

Just how big a deal is John Gruber, the blogger whose Daring Fireball site is a must-read for anyone who cares about Apple?
Here's one way to measure Gruber's big-dealness: Every year for the last decade, following Apple's annual Worldwide Developers Conference, top Apple executives have appeared onstage with Gruber for an extended interview.
But not this year.
The most likely reason: In March, Gruber wrote a scathing essay about Apple's inability to deliver an AI upgrade for its Siri voice assistant — something it had been promoting and advertising for months.
In Gruber's telling, this wasn't just a missed shipping deadline, but a sign that something was deeply amiss with Apple's leadership. If it doesn't get fixed, he wrote, "the ride is over."
Apple still hasn't delivered its new Siri — though it insists it is still in the works. And that absence became one of the biggest narratives coming out of the developers' conference it hosted in June.
A much smaller story — but fascinating for media and tech nerds like me — was Apple giving Gruber the brush-off. What does that say, if anything, about Apple's mindset right now?
"I feel them deciding not to do my show this year is a total win for me and was a huge loss for them," Gruber says.
I talked to Gruber about all of that, as well as Apple's rocky relationship with at least some developers about the way it runs its App Store, in the newest episode of my Channels podcast.
You can read edited excerpts from our conversation below:
Apple is in trouble because they're behind in AI. Do you buy that ?
John Gruber: I think there's a chance that they could be, given the almost breathtaking speed with which AI is moving. I think there's a chance that technology leads to new classes of devices that aren't phones and laptops —that we just carry something with us and just talk to a thing or something.
But even at this speed, we are years away from replacing the devices we know with some sort of new form of devices.
And OpenAI is now working with former Apple design guru Jony Ive to develop some kind of new wonder product — but the messaging from them so far is, " This won't replace your phone. You'll still have a phone."
I think it's a very interesting way of framing it — that it won't replace your phone, in the same way that your phone didn't replace your laptop.
It's so easy to get caught up when a new thing comes up. The phone is obviously the biggest thing that's happened until AI. And the phone was just a huge sea change. Everybody has a phone. It's made Apple the richest company in the world. But Apple still also makes gobs of money selling laptops. I'm recording this show with you right now on a laptop. I don't know how I would do my job without a laptop.
The Apple play seems to be: We make phones that billions of people use. Maybe they will have some AI features. But the main idea is: If you want to use ChatGPT or anything else, you'll use our phone to use them.
I think last year's developers conference, where they spent 40 out of a hundred minutes talking about Apple Intelligence — I think that's where Apple itself got caught up in the hype of, "Hey we need to present ourselves as though we are at the forefront of this whole thing," as opposed to, "No, the main thing Apple does is make these devices and these platforms," and just show that these existing platforms are the best ways to use AI from whomever.
Apple's done that over the years many times.
But the most impressive thing Apple showed off a year ago was a smarter Siri — one that could sift through your emails and texts and tell you when your Mom's flight was arriving. But that never materialized, even though they were running ads for it. And then in March, you wrote a blog post about that called Something is Rotten in the State of Cupertino.
You like Apple, you like Apple products. But by the end of the piece, you're saying this isn't just that they've missed a shipping deadline — this is cultural rot.
Is this a real problem? Or is it just them announcing early, and if they'd waited a year, and delivered on the timeframe they predicted, this would be fine?
I think it's a sign of a real problem in the whole Siri area.
The basic premise of the company is that if they hire the best engineers and designers who care about the product — whose No. 1 reason for wanting to work there is that they want to make great art — then ultimately they must make better products than their competition.
Siri has been this glaring exception. By the middle of the 2010s, Siri just sort of frustrated people. And a lot of things have gotten worse over the years. There are commands that you could give to Siri that used to work that stopped working.
Then once the LLM explosion happened, all of a sudden there's this other thing [that can have] a real conversation. Then you go back to Siri and it's ridiculous.
It really feels like more than a decade behind. It's long been a mystery within the company. Because everybody who works there knows that the bar is excellence — or to put it in Steve Jobs's term, insanely great.
And then you look and the Siri team is over there spinning their wheels for 10 years with a subpar product. And it's not this obscure piece of technology that almost no one uses — it's got a dedicated button on the phone.
So you write this blistering piece — and it's especially blistering coming from you. What was the reaction from Apple after you wrote that? Did they reach out?
They reached out. But my communications over it were mostly private. They were not happy, and they don't think it was fair.
You normally interview Apple SVP Craig Federighi or some other high-level Apple executive after their developer conference, every year at a live show. They were not onstage with you this year. Nilay Patel from The Verge and Joanna Stern from The Wall Street Journal were on with you instead.
Do you imagine that's it for you and Apple — that they're not gonna come on your shows anymore?
I've been told point-blank that it's just a decision for this year, and doesn't mean anything about the future. And I had off-the-record briefings with Apple executives. So I don't think so.
If you are permanently cut off from their top talent and you can't have those on-the-record conversations, does that change your work?
Not really. I've always set things up that way. I've always been incredibly uncomfortable and wary of access, and needing it.
I've always set things up so that I don't need them, and if they cut me off completely, I'll be fine.
And maybe better? That's the thing about this — I'm not trying to lack humility here — but I feel them deciding not to do my show this year is a total win for me and was a huge loss for them.
Why is it a win for you?
It asserts my independence.
The fact that I had a show and it was well-attended — the overwhelming feedback for the show is, "Hey, I like this better than the last couple of years' shows with the Apple executives …"
If I had gotten the usual interview with top Apple executives, I had questions I would've asked that it doesn't seem like anybody else asked.
But overall — I think it asserts my independence. And I think more than making me look good, I think it makes them look bad.
My show has never, ever been mainstream. It's appealing to a niche audience. And if Apple sees the need to communicate and have a chance to speak more as humans, as opposed to machines filled with talking points, then my show is a sort of unique venue for that.
My argument was: Given everything that's going on, including between me and Apple, the fact that Apple had to delay that, everything going on right now for Apple … I was like: "I don't think, for your sake, this is the year to skip my show."
But they did.

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