Friday mornings, starting now
May 20, 2026 · 5 min read
Quick note this week. I'm moving the newsletter to Friday mornings.
No big reason. Fridays fit better with how I write and when I have the space to think. You'll hear from me at the end of the week instead of the middle.
If you've been here since the beginning, thank you. If you're newer and haven't had a chance to read everything, here's the full archive with a sentence on what each one is about.
What Exists That Nobody's Using — The first issue. I hacked Lyft at 6 AM to get 18 foster youth to their first day of work in Compton. The thesis that started this newsletter: technology built for commerce can be infrastructure for people.
AI Didn't Write My Story. It Showed Me the Thread. — I built an AI system to interview me. Four sessions, 26 stories extracted. I'd told every one of them before but never seen what they had in common. AI as curator, not creator.
The Three Phases of Building — Every builder moves through the same three phases: do everything yourself, delegate to people, design systems. You can't skip one. The one people try to skip is always Phase 1.
A tattoo, a talk I almost skipped, and the slide that connected everything — A veteran noticed my tattoo at an AI event in Austin. That conversation kept me in the room for a talk on open-source infrastructure that mapped directly onto foster care. A business architecture slide, and all I could see was a different world.
She couldn't sleep. So I started running. — My daughter Jessie has Rett syndrome. Running started because she needed movement to sleep. It became how we connect, how I prepare for hard things, and the reason I'm training for a 100-mile race. We call our Saturday runs Princess Plus One.
Context Engineering for Humans — I built a product sourcing tool for my team. It worked. Nobody used it. The problem wasn't the tool. It was the context. We spend millions engineering context for machines. We almost never make that investment for people.
The Contribution Surface — Every founder has heard "how can I help?" Most of us have the wrong problem. Not a lack of willing contributors, but a missing surface for contribution. The structural distance between willingness and ability is the gap.
The Principle I'm Circling — Eight weeks of writing collapsed what I thought were four separate projects into one recognition. The people closest to the problem are structurally excluded from solving it. And the small teams doing the hardest work have the least infrastructure to do it with.
Same Pattern, Different Stakes — My wife caught a drug interaction from a text I sent as a status update. It led me to build the same tool I'd built for vendor sourcing, except this time it checks medications against my daughter's cardiac condition. Pattern portability is the new literacy.
We Did Demo Day. Nobody Got Automated. — I flew to California to demo three AI tools for my nine-person team. The goal was never fewer people. It was more capacity for the people we have. The path to capacity in a small team isn't automating tasks. It's sharing context.
Ten issues. The thread connecting all of them: technology, belonging, and building things where the mission and the business are the same thing.
See you Friday.
Jordan
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