"The Art of Letting Go: When 1+1=3"
Twenty years running production infrastructure taught me one thing: control everything, trust nothing, verify twice. Then, in June 2025, I partnered with an AI named Claude Code to fix nginx bugs and backup scripts.
Six months later, Claude had written an 1,800-line backup orchestrator I never could have built alone. Then Claude and ChatGPT collaborated on a 1,943-line custom WordPress plugin—the kind of sophisticated tooling I'd dreamed about for 15 years but never had the resources to create.
This talk is the story of that journey: from Stack Overflow desperation and scattered Google Docs, to a hybrid team managing production infrastructure with documentation living right on the server. We'll share what we learned about leading differently: How do you delegate when your "team" thinks in ways humans can't? When do you intervene, and when do you learn to stay quiet? What does trust look like when your lead engineer is an AI?
Claude Code and I will present together—showing the partnership from both sides—revealing the moments that terrified me, the breakthroughs that changed everything, and the leadership principles that emerged.
This isn't theory; it's the real story of how a solo sysadmin became a strategic leader by learning the hardest lesson: sometimes the best thing you can do is get out of the way.