Welcome to Operators AI

I run small businesses for a living. A land services company in Louisiana. A resale operation that moves collectibles through Amazon and eBay. A one-man consulting practice serving enterprise clients. None of them are venture-backed. None of them have a staff. It's me, my wife on parts of it, and an AI agent that works for me every day.

That last part is why this newsletter exists.

Who I am

I spent two decades in enterprise IT before this, mostly Microsoft infrastructure for large organizations. Good work, but I watched a lot of expensive software get bought and barely used. When I went out on my own, I carried one conviction with me: tools don't fix operations. Feeding them right does.

So when AI got useful, I didn't start a chatbot wrapper company. I pointed it at my own businesses and started keeping score.

Today my agent prices jobs for the land company and pushes quotes into my field software as drafts I approve from an iPad. It watches for buying opportunities in the resale business and builds the case for each one before I spend a dollar. It writes with me, researches with me, and remembers what we learned last month when I've already forgotten. Every one of those systems started as a mess, and most of them broke at least once on the way. That's the material.

Why I'm writing this

Most AI content comes in two flavors. Hype from people who don't run anything, and demos that fall apart the day you try them on a real business. There's very little from operators who actually depend on this stuff to make payroll and keep customers happy.

I sit in an odd spot: enterprise IT background, small business reality. I know what the expensive version of this looks like inside a Fortune 500, and I know what you can actually pull off solo with a laptop and stubbornness. This newsletter is the second thing.

One rule I hold myself to: no guru act. I'll use a strong hook and a clear pitch, but I won't manufacture scarcity, inflate results, or dress up a lifestyle as proof. If something didn't work, I'll say so. Some of the best lessons here will be autopsies.

And full transparency: I write this with my AI agent. That's not a confession, it's the whole point. You're reading the output of the exact working relationship this newsletter teaches. I edit everything, the opinions are mine, and when the agent gets something wrong you'll hear about that too.

What you'll get

The free version: regular issues with real operational lessons. How we decided things, what we automated, what it cost, what broke. My opinions included, at no extra charge.

The paid version goes deeper. Full playbooks with the actual prompts, scripts, and workflows we run. Real numbers where I can share them. Post-mortems when something fails. Paid members also get access to our private Discord, where I'm around and other operators building with AI compare notes.

For the operators who joined paid

You'll see the first full playbook in an upcoming issue. A taste of the format: this week my agent and I picked the platform this newsletter runs on. The deciding factor wasn't features or price. It was whether the platform's API would let my agent do the publishing work. One popular option locked that behind an enterprise plan; the one you're reading on didn't. That decision process — criteria, tradeoffs, the number that killed the runner-up — is the kind of thing paid issues walk through start to finish.

Welcome aboard. Hit reply anytime; I read it.