I was a panelist last week at the Weatherhead School of Management AI conference. 300 people in the room, five panelists, and I was the only one without developers behind me building anything.

Two months ago I'd never written a real prompt.

Why they included me on the panel.

The other panelists were impressive on paper. Two were AI consultants, focused on model risks and security frameworks. The other two ran companies with internal AI teams and developers building custom tools. I was the only person on stage who builds with AI every day, in my business, by myself, after the kids go to bed.

I assumed that gap was a problem. It turned out to be the whole point.

Issue #001 readers know how I started with AI out of necessity. That was two months before the panel. Once I saw what AI could actually do, I started using it for everything: emails, code I couldn't read, automations on my Mac Mini, replacing a $500-a-month software service with a script, cutting my team's monthly data entry work from over 100 hours to about 24. None of it was glamorous. Most of it didn't work the first time.

Then I got asked to speak about it.

Someone in the audience asked: "How does a small business owner or an employee actually start using this tomorrow?"

There was a pause. The other panelists gave consultant answers: frameworks, considerations, decision trees. They weren't being evasive. In their worlds, that question gets handed to a specialist. The audience didn't have one.

I gave specifics, because I'd made all the mistakes already. My response should sound familiar to you.

"Start with your most annoying task. The thing you hate doing every week. Don't pick it because it's strategic. Pick it because you'll actually stick with the project if it removes pain from your life. That's how you learn the tool."

After the panel, the dean of the business school caught me.

We talked for about ten minutes. I told him every meaningful piece of growth in my life had happened outside my comfort zone. He agreed, the question isn't whether you'll be uncomfortable. It's whether you choose the discomfort yourself or wait until something forces it on you.

Either way, the discomfort is coming. It's like exercise. It hurts at first. Then you adapt, get stronger. Eventually, the strain is something you look forward to.

My marketing manager quitting was the forced version. The panel was the chosen version.

Most people are waiting for permission.

A course, a framework, a certification, a quarterly initiative from their boss. They're treating it like a graduate degree when it's more like learning to drive: uncomfortable for two weeks, then automatic.

A few of my friends from graduate school are CPAs. I asked them recently if they're worried about AI taking their jobs. They aren't. But they are cautious about other CPAs who learn AI replacing them.

Nobody's going to teach you this stuff fast enough. The companies hiring AI-fluent professionals aren't waiting for the curriculum to catch up. So, dig in and start learning.

This week's takeaway:

Pick one task you genuinely hate doing. Something repetitive that takes 30 minutes a week. Open Claude or ChatGPT and try to automate it. Don't watch a tutorial first. Don't read about prompt engineering. Just describe what you want in plain English and iterate from there. If you break it, you're doing it right.

⚡ ONE MORE THING

Two stories from the AI gold rush this week. Allbirds, the wool sneaker company, pivoted to AI and the stock jumped 582% in a single day. They sold the shoe business for $39 million and renamed themselves NewBird AI. The market is rewarding any company that slaps "AI" on the door right now.

Meanwhile, Anguilla — a Caribbean island of 16,000 people — has been sitting on the .ai country code since 1995 and now collects roughly half its government revenue from domain registrations. They got lucky being assigned the right two letters. They got smart requiring a two-year minimum on every registration.

Better to be a real operator who can use the tools than to bet on a relabel or get lucky with a country code.

— Matt

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