The post-WWDC super nerd convo
Flighty's Ryan Jones joins the podcast to break down Apple's Siri reboot. Plus some weekend links.
Few developers are better positioned to judge Apple’s AI reset than Ryan Jones. He’s an Apple Design Award winner who has spent seven years building Flighty into one of the most successful indie app businesses. (And one of my favorite iPhone apps, period.)
Jones and I were both at Apple Park on Monday for WWDC, and his read on the keynote is that it was a cleanup lap. He thinks the new Siri plays to advantages nobody else has, starting with the on-device index of your iMessages, photos, and voicemails that Google, Meta, and everyone else will never get access to. He points to Joanna Stern’s demo, in which Siri surfaced an old voicemail from her uncle as a contextual suggestion, as the kind of moment no other assistant can pull off.
Apple is also still way behind the state-of-the-art AI assistants. The new Siri, for example, has no persistent memory between sessions, and the on-device indexing took days to complete on Jones’s iPhone running the iOS 27 beta.
Jones explained the unique way Apple is letting Siri understand content on a device’s screen. Siri’s context system is built on roughly 100 predefined “entity” types that apps can “donate” data to. He contrasts that rigid, deterministic model with MCP, where you hand over content and let the model figure out what it is. It’s also part of why Flighty runs Gemini server-side instead of Apple Intelligence: when a parse fails, his team can see why and retrain on the edge case, while Apple’s stack is a black box.
We also got into the other big shift in Apple’s AI strategy: its souring relationship with OpenAI. Apple is leaning harder into Google as its model partner while weaponizing its privacy stance against OpenAI, and the arc looks a lot like what happened with Facebook. Deep integration first, mortal enemies a few years later. Around 2019, Apple used privacy to kneecap Facebook, and the exact same playbook appears to be running against OpenAI now.
Jones also revealed what’s next for Flighty: an AI-built connection guide, landing in beta at the end of June, that gives you granular walking directions between gates based on your terminals, seat number, and passport. The infinite matrix of airports, nationalities, and destinations made it impossible to build before, but as he put it, it’s “right up AI’s alley.”
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Weekend links
The New York Times: “About 20 New Billionaires Could Be Minted by 3 Mega-I.P.O.s”
Wired reports: “‘Tell Him He’s a Piece of Shit’: Meta’s New AI Unit Is a Total Mess”
Vanity Fair: “Aaron Sorkin’s First Interview About His Social Network Follow-Up”
Reuters: “Anthropic v. OpenAI: Behind the bitter battle for the future of AI”
CNBC: “Prometheus is the bulk of my time, says Co-CEO Jeff Bezos”
Jasmine Sun’s latest banger: “It’s a scary time to be twenty-two.”
“I looked at 1,680 Anthropic resumes. Here’s who they actually hire.”
Andy Masley: “Why I think panic about local impacts of data centers is just a panic”
Matt Stoller asks: “What Would It Look Like If the AI Bubble Popped?”
Catch me on Prof G Markets
Thanks to Ed Elson for having me on this week to unpack WWDC and the tepid investor reaction.
ICYMI
Sources is a newsletter by Alex Heath about the AI race, featuring scoops, unique analysis, and exclusive interviews. Every week, Sources is read by thousands of decision makers in tech, finance, policy, and media.