WWDC 2025 + iOS 19, Apple’s Siri Shakeup, OpenAI Raising $40B, and THAT Signal Group Chat

Apple is shifting its exec team to hopefully fix Siri and Apple Intelligence failings, OpenAI's major funding news and new image generator, iOS 19 to bring visionOS-like redesign to iPhone, Meta’s tell-all book, and a brief history of our websites.

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Links from the show

• Behind the Mac: Editing Severance | Apple - YouTube
• Mac - Lumon Terminal Pro - Apple
• Apple’s Worldwide Developers Conference returns the week of June 9 - Apple
• Apple Vision Pro Chief Mike Rockwell Named Siri Head; Giannandrea Keeps AI Role - Bloomberg
• Lossless audio and ultra-low latency audio come to AirPods Max - Apple
• iOS 18.4 Release Candidate comes bundled with over 50 new changes and features [Video] - 9to5Mac
• OpenAI Image Generation with 4o
• OpenAI Close to Finalizing $40 Billion SoftBank-Led Funding - Bloomberg
• Meta scrambled to silence a tell-all book. Now it’s a bestseller. - The Washington Post
• Here Are the Attack Plans That Trump’s Advisers Shared on Signal - The Atlantic
• Signal, WhatsApp, and iMessage: Which Messaging App Is Most Secure?
• Introducing iOS 19 | Exclusive First Look - YouTube
• Gurman: Jon Prosser's iOS 19 Mockups 'Aren't Representative' of Redesign - MacRumors
• 8K video recording on the iPhone 17 backed by leaker - 9to5Mac
• Apple (AAPL) Explores Turning Watches Into Wearable AI Devices with Cameras - Bloomberg
• Why 23andMe failed to innovate in drugs and health care despite a DNA trove - The Washington Post
• Welcome to iWeb
• The Best Website Builder for Mac - RapidWeaver Classic
• Jason's Website
• Stephen's Website

• (00:00) - Intro
• (02:51) - Severance BTS Video
• (06:52) - WWDC 2025
• (07:45) - Siri Team Shakeup
• (13:56) - AirPods Max Update
• (17:12) - iOS 18.4 Features
• (20:03) - ChatGPT 4o Images
• (22:06) - OpenAI's $40B Funding
• (24:58) - Meta Tell-All Book
• (30:10) - Don't Use Signal For War Planning
• (41:32) - iOS 19 Design Rumors
• (48:17) - Thunderbolt Round
• (51:25) - Our Personal Site History