2025.11: Alexa Gets an AI Makeover

Here were a few of our favorites from Stratechery Plus this week.

(Photo by Justin Sullivan/Getty Images)
  1. What Amazon and Apple Might Be Getting Wrong with Alexa and Siri. Last week, Amazon announced that the next version of Alexa will be reinvented and supercharged thanks to — stop me if you’ve heard this 500 other times in the past year — generative AI. Ben and I discussed this news on Monday’s Sharp Tech, and jokes aside, it seems like a worthwhile effort to build a presence in an AI hardware landscape that is still very much in inning zero. On the other hand, I thought Ben’s subsequent analysis of the downsides of this approach was incisive, not only as a window into the technical challenges facing companies like Amazon and Apple as they try to supercharge their assistants with AI, but also the pitfalls of big company culture, where having the resources to theoretically do everything is often what prevents companies from taking more targeted, incremental approaches that have a better chance at leading to enduring success. — Andrew Sharp

  2. Rest in Peace, Skype. I appreciated Ben’s Update about Microsoft’s announcement that they were EOL-ing Skype, particularly his personal connection to the service. My first — and only — exposure to Skype was when I first started working with Ben, because that was how we communicated. It wasn’t long until we switched to Zoom — it just worked better — which is why I understand why Microsoft is finally moving on. Still, sometimes it’s worth taking a step back and appreciating just how valuable a product I totally forgot about was at a specific moment in time. — Daman Rangoola

  3. Tariffs, TSMC, and more. If you’re feeling a little confused about what exactly President Trump hopes to achieve with tariffs, then good news! You are not alone, as General Secretary Xi Jinping and the Chinese Communist Party appear to be searching for the same answers. Bill and I discussed the latest round of tariffs on Sharp China this week, including the uncertainty that pervades U.S.-China dynamics as PRC delegates try to make inroads into the current administration, hoping to determine what Trump wants and what the PRC might be able to offer. — AS

Stratechery Articles and Updates

Dithering with Ben Thompson and Daring Fireball’s John Gruber

Asianometry with Jon Yu

Sharp China with Andrew Sharp and Sinocism’s Bill Bishop

Greatest of All Talk with Andrew Sharp and WaPo’s Ben Golliver

Sharp Tech with Andrew Sharp and Ben Thompson

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