Conversations with Tyler 2025 Retrospective

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On this special year-in-review episode, Tyler and producer Jeff Holmes look back on the past year on CWT and more, including covering the most popular and underrated episodes, why single-subject deep dives made for some of the best conversations this year, the biggest AI surprises and how LLMs changed the show's production function, what happened with the Magnus Carlsen episode, listener questions on everything from hotel selection to AI x-risk discourse, Tyler's serene acknowledgment that uncontrollable laughter is something he has neither experienced nor desires, reviewing his pop culture picks from 2015, and a dispatch from Muscat, Oman.

Read a full transcript enhanced with helpful links, or watch the full video on the new dedicated Conversations with Tyler channel.

Recorded November 5th and December 15th, 2025.

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Timestamps

00:00:00 - Favorite episodes of the year

00:12:08 - AI's impact on the show

00:15:05 - The lost Magnus episode

00:17:13 - Tyler's #1 hotel amenity

00:18:40 - Tyler's growing influence and thoughts on tariffs

00:21:15 - AI x-risk discourse

00:26:22 – Copying Tyler's interview style

00:28:50 - Tyler's lack of joy

00:32:55 - How well ChatGPT answers as Tyler

00:35:15 - Tyler's 2015 movie picks

00:40:44 - Tyler's 2015 book picks

00:45:00 - Tyler's 2015 music picks

00:48:16 - Most popular episodes and thoughts on Oman

Photo Credit: Kevin Trimmer