Fifty Years

When COVID hit in 2020, wholesale shut down overnight. Retail was gone too. We had to figure out direct-to-consumer e-commerce or we were finished. I sat with that for a while, trying to work out what we actually knew about selling direct. Then I thought about the craft fairs. My dad ran them for decades. We set up, we sold face to face, we took the money home. Direct to consumer was how this company started, just in person rather than online.

I am Chairman of American Hat Makers. My father, Gary Watrous, founded the company more than 50 years ago. We have made over a million hats, and that history is what I kept coming back to in 2020, when I was trying to figure out whether we knew how to sell direct online. We did. We had been doing it since before the internet existed. What we knew was how to reach the person who wanted the hat. The channel was different, not the skill.

After COVID we committed to the next 50 years being online-first. That decision has cost money and taken longer than I expected. We are still building it. The knowledge we are applying came from 50 years of selling direct, just in a different channel. That part is not new, but the scale of the investment is.

About 30 percent of our customers come back. The average order is around $100. That repeat rate was not built with campaigns. It was built because the hat held up, the customer came back, and that happened enough times over enough years that it became the foundation of the business.

The hardest thing I have done in this phase is hire someone smarter than me for a job the company cannot fully afford yet. I just hired a CMO and a director of growth. We have four SEO partners and multiple agencies. You hire for tomorrow and you stomach the pain short term. It is a bet on the business getting where you think it is going, and you make it before you have the evidence.

I am the last one to get paid, which is how it works when you are building something. I am up at 3:30 or 4 in the morning. I run real estate on the side because the business needs the runway. I have a two-year-old, and by the time the day ends I am drained, and the question of how to be present for him when there is nothing left is one I do not have a clean answer to.

People sometimes call American Hat Makers an overnight success. I think about those first years, and my dad, and the craft fairs, and what it actually took to get here. The overnight success just took 50 years. That is the thing I come back to when the current pace feels like too much, and also when it starts to feel like we are finally getting somewhere.

I am running a 50-year-old startup. The pressure is real and I know I am fortunate to feel it. I still do not know how to be in two places at once, and I do not know yet whether the bet on tomorrow pays off. Those are the real questions right now.