The Mack Weldon team is full of talented people with diverse interests. Everyone is passionate about men’s underwear, but we also have interests outside the office. This series explores those interests, talents, and passions that go beyond Mack Weldon.
Matt Leary joined Mack Weldon in 2014 as a member of our customer experience team. If you’ve ever sent us an email, you’ve probably talked to Matt. You may also recognize his name from our First to Know emails which he sends to our most loyal customers when we launch a new product or from his starring role in our “Customer E-mails with Matt” video series. What you may not know about Matt is that in addition to being passionate about men’s underwear, Matt’s real passion is stand-up comedy. We sat down to ask Matt about working at Mack Weldon and moonlighting as a stand-up comic.
MW: Your real passion is comedy. Most people working in the performing arts have “side gigs” to make money while perusing their art. The cliché is being a waiter or bartender. You choose customer service. What attracted you to customer service?
Matt: I didn’t seek out customer service per se. It kind of just landed in my lap when I was desperate for a job after college. It was a classic temp job turned full time job type of thing. Initially, I hated it. But I later learned that I didn’t really hate customer service, I just hated the company I was working for at the time. Having worked at a couple different spots since then, I’ve realized that it’s a great 9-to-5 to have while pursuing comedy at night – good hours, steady paycheck, not immensely stressful. Plus, when you work for a company with fairly level-headed, pleasant customers, and the product you sell isn’t pure garbage, customer service can be pretty fun and rewarding.
MW: How’d you find Mack Weldon and what did you like about the company?
Matt: I was laid off from my previous job, along with about 300 other people, and the job hunt was looking pretty grim for a while. I was numbing my brain one day, scrolling through Facebook, and a Mack Weldon ad popped up. The ad screamed “startup” which was the type of company I was looking for, so I checked out the website and shot them an email. You never know what’s going to work when you’re looking for a job. After interviewing with Mack Weldon, I was sold pretty quickly – everyone had a perfect balance of laid back and driven, and the products were great. Lucky for me, they liked what I was putting out there as well.
MW: Getting back to comedy, how’d you originally get into comedy?
Matt: I’ve been obsessed with comedy since I was around 13, but I never looked at it as a thing I could actually do. I was strictly a fan. I didn’t consider myself particularly funny, and I also had an absurd amount of stage fright growing up. I was the kid crying behind the xylophone at the elementary school Christmas concert. In college, I started to realize I could make people laugh, but I still had that hardcore stage fright. It wasn’t until I went to work for David Letterman after college that I started to think maybe I could do this.
MW: You worked at The Late Show? What was that like?
Matt: I was fresh out of college and I had no clue what I was doing or what I wanted to do with my life. I claimed I wanted to work in TV production, but I didn’t really know what that meant, despite having spent four years learning about what that meant. I worked as a page for The Late Show for one year. My job was silly and annoying, and I definitely took it for granted, but it was the most important job I’ve ever had. I say that because, literally every friend I have in NYC can be somehow linked to that show. It was also the job that convinced me I wanted to be a comedy writer. Unfortunately, I hated writing. I took a few sketch writing classes here and there, but I didn’t really do anything to push myself to be a writer.
MW: So how did you go from thinking you wanted to be a comedy writer to doing stand-up?
Matt: It wasn’t until I was about age 25 that I got over the whole stage fright thing. Around that time, I got real drunk one night and signed up for a $400 improv class. I woke up the next morning in horror, realizing I couldn’t get my money back. It was the best thing I’ve ever done. Improv didn’t really work out for me, but it helped me get over my stage fright phobia. A couple years after that, I started hitting open mics in the city, and now, I’m a struggling comic pursuing an impossible dream. It’s a beautiful story really.
MW: How many times a week or month are you performing stand-up? Do you have a regular spot or do you bounce around the city?
Matt: I try to go up around three or four times a week, which is nothing compared to other comedians. There are work horses who get up on stage 12 times a week at a minimum. My personality doesn’t really lend itself to that kind of grind, especially since I like to be lucid when I’m here at Mack Weldon. I also have a weekly podcast and I’m in a band, so the nights fill pretty quickly. When I do go up, it’s usually in the East Village or Brooklyn. There’s a major DIY mind set when it comes to New York comedy, so shows and open mics can be anywhere from a bar to a library to an alleyway in Queens (not joking).
MW: Performing that many times a week means you must have a ton of material. Are you repeating a lot of the same jokes or are you constantly coming up with new stuff?
Matt: If it’s a show where I was actually booked, I’ll go out with my best ten minutes. That might consist of jokes I’ve been doing for two years or two months. I might try to squeeze something new in, but it’s really my best stuff. If I’m at an open mic though, where the crowd is all comedians, most of whom I know, I’m always trying out new stuff. That’s really the point of an open mic. I might start with an old joke to ground myself, but the next four minutes after that is going to be new. Open mics are there for you to work on your craft. It might take you three or four times going up to get a joke just right. It also could take three months, because you get a bad response, so you leave the joke behind. Then a few months later, you come back to it, and the joke hits, and you realize everyone in the room three months ago was just an asshole. There’s really no formula to this stuff.
MW: In writing, people often say you start emulating people before you find your own voice and style. Is the same true in comedy? Who are your influences?
Matt: As a comedian, there’s certainly people you really like, but you actually try not to emulate them on stage because everyone in the audience will know you’re trying to emulate them. You definitely try to be inspired by them though. I grew up loving sketch comedy like Mr. Show with Bob Odenkirk and David Cross. As far as stand-up comedians, it’s usually the obvious ones because they’re the best. Guys like Patton Oswald or John Mulaney. The more you get involved in the New York comedy scene though, the more you start to admire the up and comers. I could throw out their names, but no one would have ever heard of them. Give it a year or two though and you will.
MW: Stand-up has to be one of the toughest forms of comedy. You get immediate feedback from the live audience, both positive and negative. Any horrible or crazy experiences?
Matt: I’ve been pretty lucky that I haven’t had any terrible heckling situations. A Norwegian women kept raising her hand one time while I was performing, and when I would call on her she would tell me that my “words were too good” and she couldn’t understand the joke. Definitely the politest heckler I’ve ever seen.
MW: Do you find comedy and customer service complement each other at all? Does one make you better at the other?
Matt: I think they help each other out. I definitely have some jokes about working customer service for an underwear company. Just saying “I’m 30 years old and I work customer service for an underwear company” will usually get a laugh. I also think being a comedian has helped me out when it comes to interacting with customers. Throwing in some funny quips when I’m writing an email is a great way to prove to the customer that they aren’t speaking to a robot or some drooling 19-year-old from Nowhere America. Also, having a sense of humor definitely helps me keep my sanity when dealing with some of the more trying customers. But there are very few of those though . . . practically none . . . our customers are great . . .
MW: So you’ve been doing stand-up for a number of years now. What’s the ultimate dream or goal as far as comedy is concerned?
Matt: It really depends on the person. There are certainly comedians who will say their dream is to have a one-hour special or a sitcom and the whole world will know their name. My goals are much simpler. I’m fully aware that this path is a total nightmare. My goal is to get a little better at my craft each week and have the people around me acknowledge that I’m getting better. I’m just trying to climb the ladder without really knowing where it’s leading.
MW: You’ve become the face of our “Customer E-mails with Matt” video series. What’s the best/strangest/craziest interaction you’ve had with a Mack Weldon customer?
Matt: I plead the 5th. All our customers are great . . . keep buying our stuff.
MW: Fair enough. Last question, boxers or briefs?
Matt: I’m a boxer brief guy. I also wear our pima t-shirts pretty regularly. I’ve done plenty of stand-up in Mack Weldon t-shirts. I even wore our sweats on stage once, though I’m not sure that was the best idea in retrospect.