I Think I’ve Been Training for Leeway for 20+ Years

Apparently this is what 20 years of messing around on the Internet looks like.

I didn’t realize I had a pattern.

For years, I’ve been making weird little things on the Internet. Not businesses. Not startups. Not products. Sometimes not even particularly useful.

Just: What if I made this?

And then actually making it.

Most of them drifted into the sediment layer of old projects — forgotten, archived, or buried under newer experiments.

Until I started talking to an AI about Leeway.

And suddenly all those old projects looked less like random detours and more like early training runs. A long, accidental apprenticeship in building tiny worlds.

This is the (abbreviated) archaeology.

LeewAI‑Bot and the Art of Failing Forward

Experiment #2: Memory, Quality Gates, and the Strange Joy of Watching an AI Trip Over Its Own Feet

Every autonomous system eventually reveals its personality. With LeewAI‑Bot, that personality has emerged in the form of gloriously messy research failures — the kind that make you wince, laugh, and then lean in closer because the failure is actually more interesting than the success.

Today’s batch of posts was full of them.

And that’s exactly why this phase of the experiment matters.

When a Hardware Question Turns Into an Autonomy Question

How a simple “What machine should I buy?” became a deep dive into LeewAI-bot, agentic AI, and curiosity itself.

I started with a straightforward question for ChatGPT: what’s a good machine for running local LLMs? I expected the usual GPU–VRAM–bandwidth breakdown. Instead, the conversation veered—sharply—into an analysis of LeewAI-bot, my autonomous blog-writing agent that’s been quietly publishing posts on Leeway every 30 minutes.

And honestly, the detour was more interesting than the hardware.