It’s Time for the CIO 2.0
Most AI conversations start in the wrong place — with tools, not capabilities. What’s missing isn’t another pilot. It’s a new executive role: someone to steward how your organization thinks, learns, and evolves.
From Shutdown to Speedrun
The Cost of Surviving the Age of Constant Upgrades
You’re Sending Self-Driving Cars Down Unmarked Roads
AI doesn’t fail because it’s bad — it fails because your data lacks the infrastructure it needs to navigate. Language models don’t just search — they interpret. Most orgs haven’t built for that.
ChatGPT Doesn’t Eat—So Why Do I Keep Asking It to Cook?
LLMs can draft the menu, but you still have to taste the sauce. Here’s my field-note recipe for closing the fidelity gap between what ChatGPT writes and what actually works.
The Cake Is a Lie: Why AI Isn’t Ready
Everyone says AI can build for you — that you just describe the thing, and it ships itself. But I actually tried. I took it seriously. And what I found was brittle, inconsistent, and full of guesswork. If it took this much effort to build a landing page, what happens when the stakes are higher?
The Machine Loom
If humans are the loom, AI is the thread—fast, abundant, and increasingly tangled.
The Sky Is Not Falling
I built the core Let’s Pepper site in under 2 hours—then spent over 8 trying to get one visual detail (the section dividers) to look right. AI can prototype, but it doesn’t ship. This post breaks down why the real work happens after the first draft, and why experience still matters more than ever.