Roberto and Jon are back for another relaxed unscripted conversation, beginning with Jon’s ongoing battle with Nissan and the frustrations of modern customer service before moving onto some much happier news.

Roberto shares the early success of his new Arsenal Women: Trailblazers podcast, which is rapidly approaching 500 downloads in its first month and already attracting listeners from across Europe, North America, South America, Africa, the Middle East, Asia and Australia. The pair also explain some of the behind-the-scenes changes coming to Tailoring Talk Magazine as they work towards a more consistent and recognisable format for the show.

The conversation then turns into a deep dive on Apple’s latest public beta. Roberto shares his first impressions of the new Siri, Apple Intelligence, on-device AI, image generation, natural language search, and why this feels like the first version of Siri that genuinely gets out of your way instead of creating more friction. Jon and Roberto also discuss whether Apple’s AI could replace ChatGPT for everyday users, what still separates dedicated AI models from Apple’s approach, and why the improvements feel more evolutionary than revolutionary.

Elsewhere they discuss David Pogue’s new book Apple: The First 50 Years, Steve Jobs, Apple’s remarkable business story, the colourful iMac G3 era, and why understanding Apple’s history is valuable whether you’re interested in technology or simply fascinated by great companies.

The second half of the episode wanders through James Bond, tailoring, watches, gaming, Half-Life 2, Robocop, Telltale Games, Billy Eilish’s new concert film, Apple Vision Pro, Netflix recommendations, and Roberto’s ambitious new series exploring the costume and wardrobe of every official James Bond film, before finishing with an increasingly ridiculous discussion about making their own ultra-low-budget Bond film starring Roberto, Jon and Alex.

It’s another classic Tailoring Talk conversation covering technology, AI, Apple, gaming, business, James Bond, menswear, filmmaking, books and the creative projects currently keeping Roberto and Jon busy.

00:00 - Jon’s Nissan saga and the importance of good customer serviccandidse

03:00 - Arsenal Women: Trailblazers reaches nearly 500 downloads

07:20 - Living with Apple’s new Siri and iOS 27 public beta

14:20 - Can Apple’s AI replace ChatGPT for everyday users?

25:30 - Apple: The First 50 Years and the business lessons from Apple’s history

34:00 - James Bond, tailoring and Roberto’s new Bond wardrobe series

42:40 - Gaming, Billy Eilish, Apple Vision Pro and making our own Bond film

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