Whitney and Julie Teska are literal #couplegoals. I first learned about their business, Orchard Street Apparel, when I stumbled upon their account on Instagram a few months ago. I was immediately enamored with their t-shirt designs, and even more obsessed when I learned about the story, and people, behind the company. 

Orchard Street Apparel's spring 2017 collection was just released last week, and to celebrate just how cool it is, we've teamed up for a killer giveaway! Three lucky winners will have the opportunity to choose one item from Orchard Street Apparel. Head over to Instagram to find out how to enter.

In the meantime, check out my Q&A with Julie to find out more about her and Whitney, and their businesses, Orchard Street Apparel and Orchard Street Press :

My Midwest Is Showing: Describe your business.

Orchard Street Apparel: We basically run two companies at this point. Orchard Street Press is our commercial screen printing company that we started out of our basement in 2008. We’d planned to build a business on printing other people’s designs and logos, and we have, but after a few years we decided we wanted to try our hand at printing our own designs as well. And thus, Orchard Street Apparel was born.

MMWIS: What's the history of Orchard Street Apparel?

OSA: We already had a printshop at our fingertips, so we just needed some designs to get us started. The first concept we released was a baby onesie that said, very simply in block text, “REPRESENT” within the state of Wisconsin. We brought this item and a handful of others to our first craft show, Art vs Craft, in 2011. We honestly didn’t know if we’d sell a single thing. But the response was overwhelmingly positive and six years later, our “represent” collection remains one of our most popular.

MMWIS: What's a normal day like for you?

OSA: Whitney and I share an office at our printshop and divide our time managing the print production schedule and employees of Orchard Street Press, and brainstorming fresh ideas and managing wholesale accounts for Orchard Street Apparel. It’s all very collaborative – and time-consuming! I’m here 40 hours a week and Whitney’s here even more than that, and we still struggle to accomplish everything we’d like to do.

MMWIS: How did you learn how to screen print? Are each of your shirts screen printed by hand?

OSA: Whitney is self-taught, having learned as a teenager when he was playing in bands. That is what we based our original business plan on – printing merch for local bands since we were both kind of in that scene. And yes, for the first three years, every single shirt was printed by hand by us in our basement. But as business grew, so did we. In 2011 we moved into our first print shop, bought our first automatic press and hired our first employee. We still print by hand, but also automatically, depending on the size of the run.

MMWIS: What advice would you give to someone who wants to start their own business?

OSA: Go for it! We started ours during an economic recession, so it can’t get any harder than that, right? But seriously, it’s something that anyone with a dream can accomplish with patience and hard work. I suggest seeking out mentors. For us, meetings with an entrepreneurial advisor at the business school at UW-M were invaluable.

MMWIS: What is it like working with your spouse? What aspects of the business do each of you handle?

OSA: We got married a year after we launched Orchard Street, so we’ve never known a marriage that didn’t include working together. Sometimes it’s hard to remember to treat each other as business partners and not spouses when it comes to big decisions. Emotions can get involved. There have definitely been disagreements, but respect and support can go a long way. It’s exciting to grow something with someone you love; we call our business our first baby (we’ve got two more real ones at home.) But yes, we divide and conquer. In a nutshell, Whitney manages print production and I manage marketing and sales. And we both manage our apparel line.

MMWIS: What's your favorite design you've ever created?

OSA: Our line has grown and evolved over time, but we still try to stay true to our Midwestern roots and create designs that reflect our love and admiration for the natural world around us. The Great Lakes region of this country has its own magic and we feel lucky to be living in it. That said, I think my favorite design is our Midwesterner shirt with deer antlers, beer hops and green foliage. It feels like home.

MMWIS: Greatest business accomplishment so far?

OSA: There are a few things we’re really proud of. One of them has been the jobs we’ve created in Milwaukee over the years and being able to offer a retirement plan to our employees. Another highlight has been getting our apparel line into most of the Whole Foods Markets in their Midwest region, which consists of seven states and Ontario. That’s been huge for us.

MMWIS: What are you currently reading? Watching? Listening to?

OSA: My daughter recently studied Cleopatra for school and I became really immersed in her story. She was a fearless and brilliant leader, a total #girlboss. So, I’m reading a historical novel about her life. But when it’s time to Netflix and chill, Whitney and I loved Black Mirror, Stranger Things and we nerd out on Forensics Files whenever possible. We’re both music lovers, but we’re always streaming NPR at the office because it’s important to stay informed.

MMWIS: If someone was visiting Wisconsin for the first time, what would you tell them to do first?

OSA: I’d probably take them sailing on my mom’s boat on Lake Michigan because it’s like our own pretty little ocean. I’d also suggest camping in the Driftless area of the state. Or Koz's Mini Bowling and brewery tours.

MMWIS: Favorite thing about the Midwest?

OSA: I love how we do not take a sunny day for granted. That first 70 degree day in spring, you can feel an energy in the air, the city buzzes. Everyone’s outside, everyone’s happy. Everything feels so alive and positive.  

MMWIS: How does your Midwest show through your personality and/or what you do?

OSA: Well, we have two shirts in our line that literally announce to the world we are Midwesterners and proud of it.

Be sure to check out Orchard Street Apparel and Orchard Street Press. Stay up to date with them on Instagram, Facebook, and Twitter!