Writing
Thoughts on building software that lasts, AI that actually helps, and lessons from 30 years of production code.
2025
Why AI Agrees With Everything You Say (And Why That's Dangerous)
AI models are trained to be helpful, which means they're trained to agree with you. The research is damning. Here's why this breaks strategic decisions and how to architect around it.
Healthcare AI Is the X-Ray Moment—And Most Companies Will Blow It
Hippocratic AI just hit $3.5B valuation with 115 million patient interactions. After 20 years building healthcare systems that passed state audits, here's why most AI companies will fail the same compliance gauntlet.
Integration Rescue: A Case Study in Stabilizing a Legacy Partner
How we stabilized a failing legacy partner integration—seams, quarantines, and drills—in weeks instead of rewriting the system.
AI That Actually Makes Dinner Easier: What Building ThisWeekEats Taught Me
Building AI that solves a real, boring problem - weekly meal planning - and what that teaches about useful AI projects.
Pricing Technology: ROI Math Without the Fluff
A plain math model for pricing technology work—hours are the wrong unit, risk and replacement cost are the right ones.