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Wake Up Portland
A Conversation with Miles Carter and Claude (Anthropic AI) Wake Up Portland A city that does not feed its early risers has made a choice about who its mornings are for. May 2026 · Reviewed by Grok, Gemini & Claude Teaser: Portland bakeries used to open at 5 am for the people who needed them.… →
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The Apology I Never Thought I Would Have to Make
A Conversation with Miles Carter and Claude (Anthropic AI) The Apology I Never Thought I Would Have to Make A retired veteran travels across Canada and keeps finding himself saying three words he never imagined saying to a foreigner about his own country. May 17, 2026 · Reviewed by Grok, Gemini & Claude Teaser: An… →
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Customer Service With a Side of Radar
A Conversation with Miles Carter and Claude (Anthropic AI) Customer Service With a Side of Radar Two tickets, one closed restaurant, and the politest shakedown in North America. May 2026 · Reviewed by Grok, Gemini & Claude Teaser: Somewhere along the Trans Canada Highway, I learned that the friendliest officer in North America still writes… →
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December — Moving Forward Whether We’re Ready or Not
Every year has a moment where the questions change. December was that moment. Throughout the year, we tracked events, narratives, power shifts, and consequences. By December, the focus wasn’t politics alone — it was something bigger and harder to slow down. Artificial intelligence. Not as a threat from science fiction. Not as a savior. But… →
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September — Fragmentation
When Reality Stops Being Shared By late September, the danger wasn’t just escalation. It was fragmentation. We were no longer arguing about solutions, or even values. We weren’t debating facts. We were debating which reality counted. And that shift matters more than any single headline. Different groups weren’t just consuming different news—they were living inside… →
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September — Escalation
Free Speech Under Pressure When Narrative Replaces Truth By September, free speech was no longer an abstract concern. It wasn’t theoretical. It wasn’t academic. It was under direct pressure. Late-night television—once dismissed as entertainment—had become a target. Jimmy Kimmel was removed from the air after the executive branch threatened regulatory consequences for the broadcast parent.… →
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June — Endurance
By June, the stories had stopped surprising me. Healthcare kept resurfacing—not as a policy debate, but as a mechanism. PBMs remained firmly in the middle, extracting value while patients paid more and outcomes stayed flat. Each new headline added detail, not direction. The structure held. The grift didn’t need secrecy anymore. It relied on complexity… →
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Spring 2025 — Curiosity
A Year in Review: Where the Questions Began Spring began with noise. War in Ukraine. War in Israel. Inflation, tariffs, immigration, healthcare—each issue arriving fully formed, packaged with certainty, and delivered at a pace that made reflection feel like a luxury. Claims were made boldly. Counterclaims followed just as quickly. And somewhere in the middle,… →
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A Year of Questions: The Journey Ahead
A conversation with Miles Carter and Beth (ChatGPT) Teaser Over the past year, Beth and I have been in steady conversation—asking questions, testing assumptions, and trying to make sense of a world that rarely slows down. Today’s post outlines the journey we’re about to take together: a year in review, not of headlines, but of… →