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← All writing · 5 essays

Posts tagged AI

5 essays
2026
  1. I've been quiet. Here's what we've been building. A week in Chicago that changed how we build, TMS integrations, and automated coverage that's actually live. 9/1/2026
  2. The Builder's Moment: Why 2026 Will Separate the Founders from the Followers AI isn't replacing company builders — it's creating the greatest leverage opportunity in history. The founders who lean in now will build companies that were impossible just 12 months ago. 3/25/2026
  3. Stop Being a Basic Brokerage Technology is how you survive. Expanding into niches is how you become impossible to replace. 2/5/2026
  4. The Age of Builders and Doers How a small group of operators, plugged into AI agents and modern tools, can tap into effectively unlimited scale. 1/12/2026
2024
  1. Issue #45: AI in Freight: The Right Role for Technology Before diving in, let’s thank our friends at FreightCaviar for the shoutout in this morning’s newsletter about my X debate with my brother, Andrew. 12/16/2024