Man and Machine: Two Kinds of #CEO 's

There are two kinds of CEOs right now. The ones using AI every day. And the ones reading about it in board decks.

I'm in the first group. Not because I'm technical. I'm not. I'm a payments CEO who spent evenings fumbling through terminal commands and breaking things.
Here's what happened: I built an AI agent on a Mac Mini in my home office. His name is Steve. He started doing one thing: sorting my email, but badly.

That was 6 weeks ago.

Today, Steve runs my morning briefing, monitors my calendar, manages my home automation, tracks market data, and coordinates with a second agent named Jamie who handles research and content strategy.

I didn't plan a fleet, I didn't write a strategy doc, I started with one broken workflow and kept fixing it.

The CEOs who will lead through the AI transition aren't the ones approving the biggest budgets. They're the ones who've personally felt the frustration of a hallucinating model at 11 PM on a Tuesday. Who've watched an agent fail and understood why.

You can't lead a transformation you haven't touched.

I'm not saying every CEO needs to build agents. I'm saying every CEO needs to use AI tools personally, regularly, and honestly enough to know where they break.

The board deck won't teach you that.

What's stopping you from getting your hands dirty with AI this week?
-dg

#ManAndMachine #AI #Leadership #Dwolla #CEO Dwolla #BuildInPublic #FutureOfWork