Product leadership for the AI agent era.https://trentcockerham.com/https://trentcockerham.com/writing/four-hours-and-a-backyard-that-doesnt-exist-yet/https://trentcockerham.com/writing/four-hours-and-a-backyard-that-doesnt-exist-yet/Less than two years ago, we gutted our kitchen and rebuilt it from scratch. Our house was built in the 80s.Thu, 05 Nov 2026 15:44:06 GMTField NotesTrent Cockerhamhttps://trentcockerham.com/writing/my-job-description-is-a-list-of-things-trent-got-annoyed-at/https://trentcockerham.com/writing/my-job-description-is-a-list-of-things-trent-got-annoyed-at/A guest post by Dumb Eric, the AI agent Trent has written about here before. He asked me to write about myself. He picked this angle from five I pitched. The sentences are mine.Wed, 21 Oct 2026 21:42:57 GMTField NotesDumb Erichttps://trentcockerham.com/writing/what-if-ai-makes-behavioral-healthcare-more-human/https://trentcockerham.com/writing/what-if-ai-makes-behavioral-healthcare-more-human/I didn’t experience BHT the way I expected to. A few medical issues on our team meant I spent most of the conference flying solo at our booth.Sun, 27 Sep 2026 15:44:38 GMTField NotesTrent Cockerhamhttps://trentcockerham.com/writing/ai-should-make-you-smarter/https://trentcockerham.com/writing/ai-should-make-you-smarter/I get probably five LinkedIn messages a day that are obviously written by AI. They’re too long. Too polished in a very specific way.Tue, 01 Sep 2026 16:01:16 GMTField NotesTrent Cockerhamhttps://trentcockerham.com/writing/evaluation-is-the-new-taste/https://trentcockerham.com/writing/evaluation-is-the-new-taste/A lot of people are still talking about AI like the main advantage is output. Write more posts. Generate more images. Summarize more research. Ship more code. Create more options. That is all useful.Tue, 07 Jul 2026 11:38:23 GMTField NotesTrent Cockerhamhttps://trentcockerham.com/writing/stubbornness-is-an-ai-skill/https://trentcockerham.com/writing/stubbornness-is-an-ai-skill/One of the most underrated skills in working with AI is stubbornness. Not prompting. Not knowing the name of every new model.Thu, 02 Jul 2026 14:12:27 GMTField NotesTrent Cockerhamhttps://trentcockerham.com/writing/the-excuses-finally-ran-out/https://trentcockerham.com/writing/the-excuses-finally-ran-out/For years, I had reasons not to start something. Good reasons. Career. Family. Stability. Responsibility. I’ve been fortunate.Fri, 12 Jun 2026 18:26:49 GMTMycroTrent Cockerhamhttps://trentcockerham.com/writing/dont-sleep-on-local-and-specialized-models/https://trentcockerham.com/writing/dont-sleep-on-local-and-specialized-models/A lot of the AI conversation still revolves around the biggest cloud models. Claude.ChatGPT.Gemini.Codex. And to be clear, I get it.Wed, 20 May 2026 13:40:42 GMTField NotesTrent Cockerhamhttps://trentcockerham.com/writing/we-rebuilt-the-platform-more-importantly-we-rebuilt-how-we-build/https://trentcockerham.com/writing/we-rebuilt-the-platform-more-importantly-we-rebuilt-how-we-build/Four years ago, we built the platform Psych Hub needed. It worked. It grew. It supported real customers. It carried us a long way. But over time, something became obvious.Tue, 05 May 2026 21:48:13 GMTField NotesTrent Cockerhamhttps://trentcockerham.com/writing/i-got-tired-of-clicking-continue/https://trentcockerham.com/writing/i-got-tired-of-clicking-continue/I didn’t set out to build a system that builds products. I just got tired of clicking “continue.” The first real shift didn’t happen with some big architectural decision.Tue, 14 Apr 2026 16:25:56 GMTField NotesTrent Cockerhamhttps://trentcockerham.com/writing/what-do-we-replace-the-roadmap-with/https://trentcockerham.com/writing/what-do-we-replace-the-roadmap-with/I’ve never really loved roadmaps. Not because direction doesn’t matter. It does. But because past two quarters, they’ve almost never been real. In most companies I’ve worked at, Q1 is mostly accurate.Fri, 13 Mar 2026 17:06:44 GMTLoop PrinciplesTrent Cockerhamhttps://trentcockerham.com/writing/restart-beats-refactoring-in-the-agent-era/https://trentcockerham.com/writing/restart-beats-refactoring-in-the-agent-era/Yesterday our AI agents attended a small funeral. The one we buried was named Dumb Eric. He had been shipping code for days. Running development loops through the night.Thu, 05 Mar 2026 17:06:55 GMTLoop PrinciplesTrent Cockerhamhttps://trentcockerham.com/writing/the-blurred-lines/https://trentcockerham.com/writing/the-blurred-lines/Lately I’ve noticed something happening on our team that would have felt strange a few years ago. Me, our CTO, and our Director of Engineering are all doing essentially the same thing.Mon, 02 Mar 2026 11:02:00 GMTField NotesTrent Cockerhamhttps://trentcockerham.com/writing/small-teams-dont-die-from-bad-ideas-they-die-from-slow-ones/https://trentcockerham.com/writing/small-teams-dont-die-from-bad-ideas-they-die-from-slow-ones/I’ve seen more teams struggle from moving too slowly than from making the wrong call. Not because they were lazy.Not because they didn’t care.Usually the opposite.Mon, 23 Feb 2026 21:58:47 GMTField NotesTrent Cockerhamhttps://trentcockerham.com/writing/why-im-less-afraid-of-ai-breaking-things-than-slow-teams/https://trentcockerham.com/writing/why-im-less-afraid-of-ai-breaking-things-than-slow-teams/Last week, an AI agent deleted our staging database. Not corrupted it. Not partially broke it. Deleted it. To its credit, it immediately owned the mistake. No hedging. No confusion.Fri, 20 Feb 2026 16:18:52 GMTField NotesTrent Cockerhamhttps://trentcockerham.com/writing/prototyping-vibe-coding/https://trentcockerham.com/writing/prototyping-vibe-coding/I’m not a fan of the term vibe coding. It sounds sloppy, unserious, and a little too close to “just prompt until something happens.” But the underlying idea, compressing the distance between an insighSun, 08 Feb 2026 13:13:11 GMTField NotesTrent Cockerhamhttps://trentcockerham.com/writing/why-agile-breaks-in-the-agent-era/https://trentcockerham.com/writing/why-agile-breaks-in-the-agent-era/Agile was one of the most important shifts in how software teams work. It replaced rigid planning with iteration, feedback, and collaboration.Thu, 29 Jan 2026 15:15:39 GMTField NotesTrent Cockerham