I guess it started last week when I picked up the Messin Around Town hats.
I had just come back from a family trip where I spent every morning on the pickleball courts with the boys in my wife's family. I started playing about a year ago, and if you know me, you know that once I like something I go all in and make it part of my routine. If it's good for me, it stays. If it's not (cigarettes, gambling, the usual), I eventually let it go. Some took longer than others. lol
Every morning on that trip I was up early with no time to do my hair. So it was a hat, two espressos (one to wake up, one for the court) and out the door. The only hat I brought was a Yankees fitted, and it wasn't working. It gets uncomfortable the minute I start sweating, it stains, and honestly it's not my look anymore. Italian guy, Yankees hat, white tee. I'm not interested in carrying that stereotype. So after day one I called my embroidery guy and ordered a lightweight hat. Then I ordered fifty and put the logo on them, because that's what I do with almost everything.
Since then I've been thinking about what I actually want Messin Around Town to be. The name is catchy. People I barely know will look at me and say, “Hey, I know you. Messin Around Town, right?” It works for real estate, a newsletter, a hashtag. But I want it to be more than that. I thought about using it as a team name, but it never sounded like one, and I already have Trade Residential, which I love.
I picked up the hats on the way out to the Hamptons. Tina and I went alone. With young kids, we needed a few days of adult time after the family trip. We stayed with good friends, so there was no pressure to be anything particularly “Hamptons.” We laughed, danced a little and told old stories.
On the last day of the trip I came up with a blog name for my friend: Dry Harbor to Sag Harbor. Dry Harbor was the street we hung around on as kids. Back at the house, I fed the best parts of the weekend into ChatGPT and told it to write like an elite Hamptons blogger. It was excellent in a completely ridiculous way, like a woman who'd gone from hard beginnings to the most graceful Sag Harbor life imaginable. We all laughed. But that night, falling asleep, I felt a little envious of the idea. I wanted a place to put down my own days and thoughts for a future version of myself. Sort of a diary, but in a manly way.
So here we are. The only thing I didn't want was for it to sound machine-written. The plan: one AI helps me organize the raw thoughts, I write the post myself, and another pass cleans up the rough edges so it doesn't read like pure rambling.