The Side Hustle That Grows Legs

I had a call this week that I can't stop thinking about.

Super sharp guy. Decades in tech. Great day job. And his ask was so clear it was refreshing: "I want a digital side hustle I can run at night, by myself... and I haven't made my first dollar online yet."

I hear some version of this every single week. And here's where almost everybody in that spot goes wrong.

The technical people default to building a TOOL. Some whiz-bang AI thing for plumbers or pool guys. And I get it, building is the fun part. But there's a trap hiding in there, and I've watched so many people fall straight into it.

It goes like this: "I built this thing, I sold it to a couple of plumbers, and now I can't find any more customers. I'm stuck."

Because selling business tools isn't a building problem. It's a knocking-on-doors problem. Unless you've got millions in funding or something that goes viral, you're out there earning trust one awkward conversation at a time. Which is the exact opposite of the quiet, do-it-from-home side hustle you signed up for.

So here's what I told him instead: start a local newsletter.

I am genuinely so bullish on local newsletters right now. Here's why.

1. The infrastructure is cheap and FAST. Within a week you have a product, a logo, a real thing you can show your spouse and your friends. That immediate feedback loop matters way more than people think.

2. The money starts with sponsorships and ads. Local businesses want to reach local people, and you're the bridge.

3. And this is the big one... it grows legs. Once you have the attention of a community, doors open that you couldn't even see from the starting line. Business owners reply to your emails. Some of them need help with way more than a newsletter ad. You can write the newsletter, hand those leads to someone who loves the consulting side, and split it. You stay in your lane, they handle the part you don't want, everybody wins.

4. Whatever you've already done in your career is borrowed authority. Your day job, your background, your reps... that's instant credibility you don't have to manufacture. People hear it and go "okay, this person knows their stuff." Use that.

The pattern underneath all of this: don't build the tool first. Build the audience first.

The audience is the asset. The tool, the course, the consulting offer... those are just different ways to serve people who are already paying attention to you. Skip the audience and even a great product turns into a door-knocking job.

And look, the money doesn't come in giant buckets at first. It doesn't. But you're also not spending six months in a cave building something nobody asked for.

Start the thing you can ship this week. Then let it grow legs.

Stay in the fight, Kevin