Q. What was your first big watch purchase?
A. When I was doing music radio back in Baltimore in the late ’80s and early ’90s, the watch that drove me was a standard Rolex Presidential, because I was into status at the time. That was my first real signing bonus.
What did that purchase mean to you, given that you were struggling with drugs and alcohol at the time?
The Rolex didn’t make me happy, so it had to be a car. And I bought a Mercedes, and that didn’t make me happy. I lost my job in Baltimore, and I remember how I felt when that Mercedes was pulled away. It was bone-crushing to me.
At that point, I was starting to realize, “You’re kind of a monster here.” I was really grossed out by myself. When I finally sobered up, I wanted to get rid of this watch so bad, and my ex-wife wouldn’t let me do it. She said, “No, you’ve got to save it, it’s worth money.”
I was trying to shed myself of the garishness of my past. And the material wealth. Which is bullcrap. You can be charitable and have nice things. You don’t have to be a monk.
So when did you actually start to collect?
After I moved to New York [in 2009], I started to get pretty serious, quickly. When I say serious, I mean pretty sick.
What draws you to a Patek?
I love the simplicity. I love the size of the face. It’s not overdone. It’s just solid.
You also have some great vintage pieces. Is there something about the appeal of old-school watches that overlaps with your politics — a back-to-basics approach?
I think so. I think it hearkens back to some of my political values. There’s something to hard work. You know, I’m starting to collect Omegas, the old Omegas, and there’s something about the old faces, the calling back to a simpler time.
And yet, at the same time, I also have the Nixie watch. In some ways that hearkens back to the old days, but I’m really into Silicon Valley as well. I’m really kind of this guy who is broken in two.
Speaking of being broken in two, you seemed like a changed man during last year’s election. Why?
The election changed me profoundly. One of the things I like about watches is the integrity of watches. I have this Journe that I absolutely love, because of the weight of it. It just feels like it has integrity.
One thing I learned is, not a lot of people have integrity. What they said they cared about, they didn’t care about. They were arguing for their team. The big mistake I made was that I associated that with people on the left. I got holier-than-thou, thinking, “You people will switch on a dime, we’d never do that.” Then everybody switched on a dime. I was stunned.
You’ve talked about how you regret your own divisive rhetoric over the years. Why?
This has to stop. We’re just driving the stake into the heart of the republic, and it’s getting worse and worse and worse. All that it takes to break this cycle is for enough people to say: “Wait a minute, I just want to admit my part, and I want to stop. I’m going to try to really listen to people on the other side.” We may still disagree. But we’re not going hate each other.
Do you worry that your fans might resent that you have so many nice watches?
Luckily, no. You know, I’m a capitalist, so my audience doesn’t begrudge me making money.