Apple's HUGE Siri AI Fumble w/ John Gruber

Geared Up

Tech legend John Gruber joins Andru Edwards and Jon Rettinger to unravel the story behind Apple Intelligence and its delayed features in this episode of Geared Up. From early WWDC promises to today's reality, they dissect how Apple got comfortable showcasing features it didn't hav eready, and what that says about their internal culture, marketing strategy, and the future of Siri.

Something is Rotten in the State of Cupertino: https://daringfireball.net/2025/03/something_is_rotten_in_the_state_of_cupertino

Gruber shares rare behind-the-scenes insights, including his personal evolution in covering Apple and the moment he realized the company had broken a decades-long precedent. The trio also explores the rocky launch of Vision Pro, Apple's approach to foldables, and why Apple Maps is a cautionary tale for Apple Intelligence.

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Chapters

1. John Gruber of Daring Fireball (00:00:00)

2. Something is Rotten in the State of Cupertino (00:05:28)

3. Did Apple Know Personal Context Wasn’t Ready? (00:10:21)

4. Did Pre-Recorded Keynotes Add to Siri Delay? (00:12:59)

5. Where Did Apple Intelligence Go Wrong? (00:22:21)

6. The Pressure on Apple to Deliver in AI (00:27:23)

7. Apple Advertising AI Features Too Early (00:31:24)

8. Realizing the Apple Didn’t Have a Working Demo (00:38:10)

9. Does This Change How We Cover Apple? (00:43:55)

10. Is the Apple Intelligence Brand Damaged? (00:47:36)

11. How is Apple Vision Pro Doing for the Company? (00:52:01)

12. The Upcoming Foldable iPhone (01:00:00)

13. Mark Gurman’s Apple Scoops & Reporting (01:09:26)