On Hiring

The hardest hire I ever made was someone smarter than me who I couldn't actually afford yet, and I knew it when I made the call, and I still waited longer than I should have.

For years I promoted whoever had been around the longest. Longevity felt like loyalty and loyalty felt like the thing to reward, right? The problem is longevity wasn't really built on performance in a lot of cases, it was built on the fact that I never cleaned house. I kept the same people in roles they'd outgrown because I was busy and comfortable and, honestly, not great at starting that conversation. You compound that over a decade and you end up with a team that reflects where the business was, not where it's going.

COVID forced it before I would have gotten there on my own. When wholesale collapsed overnight and we had to reinvent the whole distribution model, the gaps showed up immediately. I needed people who could think ahead of me on paid acquisition, on retention, on the ecommerce side. I didn't have them, and I couldn't promote someone into that capability just because they'd been around long enough.

So I started hiring for tomorrow, which means you're hiring for a problem you don't fully have yet at a salary that genuinely hurts right now. I just brought in a CMO for American Hat Makers, and a director of growth, and I've got four SEO partners and a handful of agencies on top of that. It's a lot of overhead for a company at our stage, and I believe in every single one of those decisions because I made the other kind for too long. You either hire ahead of the problem or you promote the wrong person into it and hope, and the hope doesn't usually work out.

Nobody is actually good at hiring, which means you better get good at firing, and firing someone who should have been let go earlier is just the correction you owe them. I carried people in roles too long because I didn't want to have the conversation, and in retrospect I was not doing them any favors either, because they were in over their heads and they knew it and I knew it and we all just kept the fiction going. I'll pull my own covers on that.

The equity question gets complicated when you're growing. Everybody wants equity now, and I understand the logic because that's where the market went, but I look at what my father Gary built over fifty years at American Hat Makers and it makes me pause, right? Fifty years of getting up every day and building something real, and people want a piece of it on day one of employment. I'm not saying no always, but I'm saying the conversation is more complicated than a line item on an offer letter.

What actually retains good people, anyways, is ownership of their work, which is different from equity on paper. We have a policy where any team member can make a $500 call without asking me. If a customer has a problem and someone on the team can solve it for $500 or less, just solve it. That gives people real authority, and a team that actually has authority cares in a way that a policy manual never gets you to, and I think that's worth more than a stock option to the right person. If it isn't, they might not be the right person.

I'm still learning to hire and I don't think I've cracked it. What I can say is I understand now that the team is the company, right, not the product or the website or the ad budget. You walk into a facility and you can feel in about thirty seconds whether the people there want to be there, and your customers can feel it through a screen. If I had figured that out ten years earlier we'd be in a different place, and I try not to think about that too much.