Writing
Thoughts on building software that lasts, AI that actually helps, and lessons from 30 years of production code.
2025
20-Year Systems, Part 1: Design Constraints That Age Well
The design constraints that prevented rewrites and kept a healthcare-scale platform running for two decades.
The Platform That Processed $100M (And Why You've Never Heard of It)
The reality of B2B infrastructure that moves real money - invisible, unglamorous, and quietly essential.
Your AI Project Is Stuck in Pilot Hell Because You Hired a Developer, Not an Architect
Why most AI initiatives never make it to production - and what architecture has to do with escaping pilot hell.
What $20M in Replacement Cost Actually Means (And Why It Matters)
Breaking down what a $20M replacement estimate actually represents - and why 'just rewrite it' is almost always a multi-million dollar sentence.
The Architecture Decisions That Prevented $20M in Rebuilds
The seven key architecture decisions that kept Conductor running for 20 years without a ground-up rewrite.