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 (youtu.be/7PfAkGErxS0) 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