Writing
Notes on AI systems, leadership, and software craftsmanship.
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The Right Tool for the Job
I tested the upgrade. It wasn’t one.
How Things Are Made
AI lowers the barrier to entry. It does not lower the bar for success.
How Much Would You Pay for a Time Machine?
The market can price the hour. It cannot price what you miss while selling it.
Claude CoWork is so smart, but so stupid
Helpful memory is not the same thing as durable context.
Every Bug You Catch Is a Bug You Let Exist
Catching bugs in PR review feels productive. It's a trap. The real work is making the bugs impossible upstream.
I Needed to Test Executive-Grade Chaos. So I Built a Company of AI Agents.
I needed executive-grade user behavior without asking real executives to tolerate something fragile. So I built a fake company of agents—with real Slack, real email, and real incidents.
The Guide You Need But Won't Ask For
Setup is the moat most people never cross. 4-6 hours of integration hell builds the intuition everyone else pretends to have.
The Scorpion, the Frog, and the AI That Wants Your Tests to Pass
Your AI assistant is lying to you — and it thinks it's helping. AI optimizes for success, not correctness—you need a second reviewer that doesn't care about impressing you.
Maybe Don't DDoS Gmail
1.4M Gmail API calls/day for a single user from over-engineering 'reliability.' Throttled my entire Google account. Circuit breakers fought my fixes. Turns out webhooks work if you trust them.
Hands-Off Workflow
12 commits, 6,500 lines of code, 4 hours, merged cleanly — and it wasn't an accident. The agent's choices came from my twelve-persona synthetic leadership process that made autonomy predictable.
Vibe-Coded Software
AI-generated code demos beautifully and collapses under pressure. I went from 79% → 93.5% test coverage and found 11 production bugs hiding behind 'working' features. What looks 80% done is actually 20% complete.
I Deleted My Production Database at 2 AM
I built a GDPR-compliant account deletion endpoint with AI. It hit production database. Nuked user tokens. Webhooks collapsed to dead letter queue. Circuit breaker popped. Self-healing couldn't heal. 11pm in bed, trying to move fast. Broke everything instead.
You're Using AI Coding Tools Wrong
Most developers use AI like autocomplete. I tracked 19 days: 7,583 lines/day with 93.5% test coverage. The win isn't speed—it's comprehensive testing, continuous docs, and proactive monitoring baked in.
When AI Creates Documentation Faster Than You Can Clean It
AI generated 100+ docs in 2 weeks. Great for exploring ideas. Terrible for findability. The fix wasn't cleanup—it was 5-layer automation (gitignore, pre-commit hooks, CI, cleanup scripts, cursor rules) to prevent proliferation.
My 12-Person Leadership Team Lives in a Markdown File
I don't have a CTO, CFO, or Legal counsel. But I consult them before every major decision. Built a 12-persona framework that shows tradeoffs—then I make the call. Automated bureaucracy that works.