Chance Kelch

Former Amazon, StockX, and Stripe exec.

Now building reliable AI systems—and writing about what works and what doesn't.

The Scorpion, the Frog, and the AI That Wants Your Tests to Pass

TL;DR: 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

TL;DR: 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.

TL;DR: 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

TL;DR: 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

TL;DR: 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

TL;DR: 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

TL;DR: 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.

Context Management at 1M Tokens

TL;DR: The half-life of superintelligence is about 30 minutes. Claude can be mid-refactor, then start undoing its own work. I hit context limits constantly running multiple instances. Built a TEMP file system with cursor automation that preserves state when the AI forgets.

My 12-Person Leadership Team Lives in a Markdown File

TL;DR: 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.