At Fifteen

I joined the American Hat Makers sales team at fifteen years old, before I was old enough to drive. My solution to the logistics problem was to hire my brother. He had a license while I had hats to sell.

He took half the money. I was the one doing the shows, selling the hats, managing the inventory, talking to customers. He drove, and at fifty percent the split did not reflect what either of us was actually contributing, so I let him go.

At sixteen I was loading four to five hundred hats into a van and driving cross-country to set up booths at festivals by myself. It was 1990, so there was no cell phone and no GPS, just a map and the shows on the calendar. I would drive however far it took, set up the table, sell what I could, and start the drive back.

That experience felt like logistics at the time, not a lesson. But looking back, the brother situation taught me something about deals that I have had to relearn more than once over fifty years of running this business: the structure matters before anything else does. When I hired him, I did not define what the job was worth or what fair looked like, because I assumed we would both just know, and we did not.

I have made versions of that mistake with agencies, vendors, partners, and employees since, and the pattern is always the same. Someone comes in without a clear definition of what success looks like, and six months later you are sitting across from them with completely different ideas about what just happened. You have to define the deal before any work starts, not just what it pays, but what done actually looks like, and what you both do when it is not going well.

My brother did not hold a grudge, and we have talked about it since. He probably thought I was being unreasonable at fifteen, and maybe he was right about that. But the hire was a business decision, and firing him was a business decision, and at fifteen years old that was the clearest one I had made yet.