The Hire

A few years ago I hired a CMO, a director of growth, and brought in four separate SEO partners at the same time. It felt like driving with one eye on the road and one eye on the bank account.

The problem with talent is that good people do not wait for you to be ready. They are not going to hold a slot while you get your margins right or finish the quarter. By the time the budget is comfortable, they are somewhere else, and you are still running every function yourself because you waited.

My father built this company over fifty years, and there were stretches where he was down to one or two employees and did not know if there was a next year. I think about that a lot when I am trying to justify a hire that does not yet make financial sense. He held the whole thing himself for years before he could afford help. He did not wait for the right moment. He hired when he had to and figured out the money after.

The specific version of this that I got wrong early was thinking I needed to hire for where the business was, not where it was going. So I hired at a level I could justify today and then watched that person hit a ceiling in six months because the job grew faster than they did. You do that a few times and you learn: the right hire is almost always the one you cannot quite justify yet on paper, which is an uncomfortable place to operate from but usually the right call.

There is also the equity conversation. I have had candidates tell me, straight-faced, that they want a piece of the company. We have been making hats since 1972, sold over a million of them, and earned 16,000 five-star reviews without handing out equity once. I understand the ask. I just think equity is the wrong lever in a fifty-year manufacturing business, and what actually retains good people is whether they want to come back on Monday.

What I know now is that the discomfort of a slightly expensive hire is almost always cheaper than the cost of the wrong one. A bad hire at a senior level costs you six to twelve months of momentum, depending on how long you take to admit it. I have paid that tuition more than once.

I am the last one to get paid. I am up at four in the morning. My job is to carry the gap between what the business earns today and what the people I need cost, and the faster I make peace with that, the better my hiring decisions get.

I do not have a clean answer for the exact timing. I just know that waiting until it feels comfortable is usually waiting too long, and the hire you could not quite afford is almost always the one you needed six months earlier.