The Hobbyist #11: An Interview with Driveway Paradise Founder Matthew Carpenter
Sport jorts, muscle tees, and ball caps...oh my!
Graphic design courtesy of Thomas Euyang
Driveway Paradise, which blends 80s and 90s sports aesthetics with modern silhouettes and an updated color palette, seems like it’s everywhere. I don’t know how I made my way to the brand, and I’m not the only one. To hear the brand’s founder Matthew Carpenter tell it, many of the company’s devotees have a similar relationship to it as I do. Some friend of a friend that is hipper than you posts something on IG and in that photo they’re wearing something extremely cool from Driveway Paradise. For me it was the vintage polo. I forgot who was rocking it but I quickly jacked their swag and wore it better.
From there, I purchased the classic muscle sleeveless tee, which is excellent for showing off the pasty noodles connected to my shoulders; the place where most peoples’ biceps are.
The point being, once you’re in the Driveway Paradise ecosystem, you don’t leave. Right now, I’ve got The Masters early round coverage on the TV (how do we not have anything outside of featured holes and featured groups right now???) and am rocking a tee from the brand that is probably the softest thing I own. As soon as it showed up at my door, my wife rolled her eyes and said, “You’re never gonna take this thing off.” She wasn’t annoyed that I would wear it religiously; she was pissed she would never have the opportunity to steal it. Little did she know that the sport jorts were also in the package.
I caught up with Mr. Carpenter to figure out how a high school quarterback becomes a D1 safety becomes an assistant in the entertainment industry becomes a producer for YouTube creators becomes a fashion mogul. My dude is one of the best guys around and someone I’m rooting for, always and forever.
Buy Driveway Paradise apparel here. You won’t regret it. Also: remember to tell a friend to subscribe. This thing is growing fast and I’m truly honored.
How long have you been in LA for?
Matt Carpenter: I’m going on 10 years. I moved out here directly out of college.
Tell the readers about your college experience.
MC: I went to Northwestern and played football for the first year and a half or so. I didn’t know this going in, but the journalism and radio/television/film programs lead to a big migration of people to LA after college. People go to Los Angeles to work in entertainment. That was my first gig out here 10 years ago.
You played defensive back in college, yeah?
MC: I was a safety, but I identify as a quarterback. I'm six foot two, which is not tall for a quarterback. I just wasn't tall enough. I would go into these camps and combines in high school. I remember going to SMU and they were really interested in me as an athlete, but they were like, ‘you're not going to play quarterback here.’ Our four quarterbacks are 6’5” and above. I went to a small high school in Dayton, Ohio and I played QB. Our senior year, they were just like, ‘We don't have enough players. You got to go play safety and play both ways.’ I was more of a running than a throwing quarterback. I ran the speed option essentially, and I was doing 25 to 30 carries a game and then playing defense on the other side of the ball. It was actually a blessing because I put the defensive side of the ball on tape and that was how I started to get offers.
You were on the team for about a year?
MC: Yeah, I left my sophomore year.
What did you think you wanted to do if it wasn't football?
MC: I had the opportunity to take some internships in entertainment during back to back summers. One was at Sony in the creative execs department, and then one was at Paramount in the creative advertising department. Being on both lots and living in LA for the summer was so cool, grinding out the resume process so that when I graduated they could see that I had actual jobs. It's very similar to the consulting or finance route. You go and get these internships and then there’s this funnel. My first year out of school I worked at a talent agency. It was ICM at the time, but it's CAA now. I knew I wanted to explore film, TV, brand and content, and the media side of things. I just didn't have those opportunities in Chicago.
What did you do for your first job?
MC: I was in the mail room. It's antiquated, but it’s a helpful way to learn who the agents are. You're kind of corporate flirting with a lot of these folks, and then when an assistant job opens up, you get an interview.
What do the next five years look like for you? Were you mostly in the agency?
MC: I was in the agency world and then from there I jumped to a company called Studio 71. I wanted to go more into the production side of things. I saw the writing on the wall in the global branding department at ICM, and the digital space was getting hot. It was only getting bigger and you can't really fight technology.
I wanted to work with creators and people on YouTube and explore that world. I had an amazing boss over there, and I went from assistant to associate producer to producer. We started our studio out in Burbank, and we were basically building YouTube channels for traditional talent. We shot, wrote, edited—pretty much everything. I first tried to do this job inside the company, but it was the time where there were a lot of running companies and athleisure companies popping up, starting to scratch the itch on YouTube and cut their teeth a bit. I wanted to go pitch these people and build their YouTube channels.
My boss at the time was like, ‘Yeah, that sounds great, but I can't do anything for you. You'll have to handle this on your own.’ I started taking meetings and I ended up meeting with really cool people and really cool founders. Every single one of them was like, ‘Yes, let's get a meeting set and talk about how you guys can build our YouTube channels.’ Ultimately, I was coming back to our company and we just didn't have what it took to fund those projects. It felt like a good time for me to go. I became a freelancer, directing branded shorts and spots, connecting creators with brands and that kind of stuff. That's what led me to Driveway Paradise.
How does the idea for the brand emerge?
MC: It was the first time in my adult life where I wasn't at a desk from eight to eight. In the entertainment world, you’re at your desk answering the phone because the phone equals business. You just don't miss calls. It’s the rule. For the first time ever, I could go play tennis at 4:00 PM. I could go make a basketball run at five, I could go to the gym at 11. I started to see a lot of my friends wearing stuff advertised from big brands. Stuff marketed as stronger, faster, sweat wicking, more performance, more stretch, all these things.
At the end of the day, you're like, ‘Am I really trying to shave off seconds from my mile time? Do I need the most performance t-shirt or pair of shorts to go play three sets of tennis with my friend who I'm going to drink beers with after?’ I played with elite athletes and the coolest dudes on the team were wearing cotton t-shirts that they cut off themselves. Dudes heading to the NFL were wearing cropped tees and cutoff sweat shorts. I just felt like there was a disconnect between the streetwear world and the performance world. Our goal is to marry them.
I’d say you’re achieving that goal.
MC: We're trying. You see Saquon Barkley and OBJ and all these really cool elite athletes. What are they wearing in the off season when they're running routes? They're wearing big baggy cotton. Why do other people have to wear the most performative, stretch-fitting, bodybuilding type attire? I don't get it.
When did you feel like this went from a pie in the sky dream to something that’s actually happening?
MC: We started so slow and we're still slowly growing, but we're now trying to go get some real capital, hopefully, and pour some gas on the fire here and scale it. When we started with word of mouth stuff, organic growth was awesome. It was very fun seeing my friends support the brand, which I'm very grateful for. Obviously, you have your immediate family and friends, and then I would see their friends who I kind of knew buy it, which was fun. Then we would see their cousins or their brothers or their friends buy it. It started to become three or four degrees of separation out from the original person, and that was from $0 on marketing. The pick up tee was our staple, and that's what brings people back—marrying the world of streetwear and performance while using innovative plant-based fabrics.
We started with algae and cotton spandex, and that was cool. Then it was, ‘How do we make this even a little bit better?’ We found mint. All of our pick up tees are made out of mint, so it's sustainable. They're naturally antimicrobial, so they never smell. A Nike shirt will smell after 40 or 50 washes because those are the topical finishes that are on there, but our stuff is naturally baked in, so it'll never smell. It started with that shirt and then we raised a tiny bit of family and friends money. From there, I started to spend much more time on it.
Were you just keeping yourself afloat with savings when you had started?
MC: It was that with the initial pre-seed round that we raised. We were recycling every bit of cash that we were making back into the business.
What are some comparisons for your brand?
MC: The way that Bandit Running has taken over that space is awesome. They've done such an amazing job. I'm such a fan of theirs, the way that they're in the running community and their formula. We're trying to build a similar community, but with pickup sports. That coincides with my personal life. love playing pickup sports with friends during the week.
Is that…your hobby?
MC: I play pickup basketball week nights and on the weekends. Golf, tennis, and basketball are my three. I started to play a lot of padel, too. It’s probably the most fun racket sport that I've ever played. My fiancée and I like to go do all the LA shit, man. We go to wine bars, we go on hikes. I'm a big reader, so I'm trying to read as much as I can. I think hobbies are really important.
I don't know about you, but I think that people who don't have hobbies are innately running the social media gambit over and over and over again. They just never get off. When we play pickup basketball, I don't pick up my phone for two hours. I'm just playing basketball. At Driveway Paradise, we really want to really help kids who are coming up in the world who are tired of social media. We want to help get them to in-person encounters with friends, playing sports with friends. You can go and get on Instagram or Snapchat or TikTok or whatever platform and do your thing, but there also is a time that you can go and hit tennis balls or hit golf balls and chat and not have to DM each other.
Who's the Driveway Paradise fashion icon?
MC: Andre Agassi.
Fuck yeah. Have you read his autobiography?
MC: It’s one of my favorite books ever. We just made the sport jorts. I don't know if you saw those or not, but they’re my magnum opus. We worked so hard on designing those. We made them exclusively because I'm obsessed with all of his outfits from the 90s. We took that silhouette and style from the 90s and early two 2000s, and then we just made it a tiny bit more modern and performative to keep its shape. They actually sold really well. I was very pleasantly surprised by them, because I did not think people would be down to buy them. I thought they would just be for me. Our head of design Alex and I always say: “We make 'em because we want to wear 'em and hope that people buy them.”
Who else do you like in the tennis world?
MC: You see Naomi Osaka wearing a Nike Cotton T-shirt in warmups, and that's sick. Tiafoe was wearing Nike jerseys during warmups. There aren't any rules that you can't wear that stuff on court.
Are you a player too?
MC: I played all the sports growing up: football, basketball, baseball. I come from a family of athletes. My brother played baseball at Michigan State. My mom played tennis at Arizona State. My dad swam at Illinois. My sister was very smart to play volleyball in high school and then just go be a student in college. We just played all the sports growing up. When I was tired of basketball and baseball and I just wanted to focus on football, my mom was like, ‘Maybe you go play tennis to get your footwork better and get faster.’ It was great. She beat my ass all the time on the court. She still beats me pretty regularly because she's just an absolute backboard. I'm obviously not as good as I used to be, but I love getting out there. It's such a meditative sport as well.
Tennis is up next for me, I think.
MC: Dude, it's a great workout. I mean, golf is so fun. It’s the hardest sport I've ever played, without a doubt. But you're not sweating buckets when you're playing golf unless it's 105 degrees in the summertime.
I think we need a Driveway Paradise x The Hobbyist day of activities sometime in the future.
MC: What better way to chop it up than playing sports with your friends? It’s the best.