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photography by cody guilfoyle

Consider the greeting card: sweet, sent with love, and cherished—quite often for years to come. When it comes to the cards designed by Ashley Molesso and Chessie Needham for their stationery brand, Ash + Chess, there’s even more love in the mix. The couple founded their company after just a year and a half of dating and continually find new ways to help other people say “I love you.”

Their work is vivid and playful—as if “Lisa Frank and Rifle Paper Co. had millennial lesbian daughters,” Molesso jokes. With rainbows to go around, plenty of feminist mottoes, and a healthy splash of neon pink in virtually everything they offer, Molesso and Needham creates cards, prints, accessories, and even wallpaper with a perspective just as bold as they are. Below, they share their secrets to running a business with your significant other.

How did you meet?

Ashley Molesso: We met on a dating app called Her in the summer of 2015. I was actually skeptical about meeting up with him because, up until that point, I literally had the worst dates ever from the Internet.

Chessie Needham: We went on a first date that we later found out we were both hesitant about. I had another date lined up that night, and Ash almost canceled on me. Luckily, we went! We just ended up grabbing a drink and then walking around and sitting in McCarren Park for hours. We didn’t want the date to end. It just took off from there.

Molesso: Oh, and he taught me which parts of grass you can eat. So we ate grass in the park. Looking back on this, it sounds really gross, but it was so weird that I was like: He is pretty much the one.

How did you start working together?

photography by cody guilfoyle

Needham: Ash took me to walk the Stationery Show in 2016 and kept talking about this dream she had to own a stationery company. I couldn’t really wrap my head around it, but I encouraged her anyway. Then somehow we decided that we’d work on it together, and she taught me to hone my art skills. We started off with just six cards, printed 50, and spent $2 per card (way too much for a card when they wholesale at $2.50 and retail for $5). I was really confused at how we’d ever make money or build a company around it.

Molesso: It just kind of happened. He was really interested in my art background—interested enough to actually want to learn from me. So at first, I taught him how to draw a cowboy hat and then we moved quickly to making designs in Illustrator. And then, not even a year into the relationship, I took him to the Stationery Show to show him what life could be like if I started a company. It seemed like a really fun and exciting way to make art affordable on our end and affordable for consumers and be able to get cute and powerful messages out to the world.

How would each of you describe what the other person does?

photography by cody guilfoyle

photography by cody guilfoyle

Needham: I would say Ash is the beauty behind the company and I’m the brains—just kidding! Ash is really the art director and the main one. She only works one day a week part-time, and I work full-time at a high school, so she has a lot more time for Ash + Chess right now than I do. That will change soon though. We both plan on working full-time by next fall. Ash can churn out five cards in the time that I can design one, so she designs more than I do.

Molesso: When Chess isn’t worrying about his 9-to-5 job as a special education high school teacher, he’s coming up with the best concepts for more of our text-based greeting cards. “Pretty Much My Fave” is one of our top sellers and one of the first cards he designed. He is extremely smart, so he brings a lot of “word stuff” to the table, while I am the most visual and creative one. Also, Chess is really good at being professional and dealing with customer service. He’s a really fast worker and can create invoices quicker than I can. He’s good at business, and I’m just here for the rainbows.

What is your brand aesthetic and how does it differ from your own sense of style?

photography by cody guilfoyle

Needham: I’ll let Ash describe our brand aesthetic because she really loves comparisons. Ash’s designs are unique, but I don’t know exactly how to describe it. They don’t look like anybody else’s to me. Ash dresses like she works at Ash + Chess. She does.

Molesso: Our brand aesthetic is as if Lisa Frank and Rifle Paper Co. had millennial lesbian daughters. Lisa in the sense that our color palette is very retro and nostalgia invoking, with bold velvet poster vibes and neon colors. Rifle in the sense that we feel like we’ve hit a niche spot of design that no one has touched on before. Chessie’s aesthetic is more ’60s, ’70s vibes, focusing on texts and fonts in a cleaner design style, while mine is a more hand-drawn, illustrated look. Chess’s physical aesthetic is “tough lesbian,” so it really cracks me up when he wears pink at our shows.

Are there any rules you follow to separate work and your romantic relationship?

Needham: We started the company pretty early in our relationship, so it’s kind of always been there. I think it helps that we are also best friends, so we just love to spend time together. We usually set aside time for just us, but we also both really love Ash + Chess, so it doesn’t really feel like work when we’re doing it. The only rule I have is that Ash can’t talk to me about Ash + Chess when I’m getting ready for my other job in the morning, but she breaks it a lot.

Molesso: To put a timeline on this, we’ve been together for three and a half years and have had the company for almost two years. So we’ve been business partners for most of our relationship. It feels really natural that it’s already incorporated into our relationship—it feels like our baby. We both put so much work and love into it that we are literally creating something, and every day it brings us closer together. I do admit that sometimes I don’t know when to not talk about work and I only realize it when Chess tells me to stop because he’s just dealt with high school kids for 10 hours. So we still have some work to do on boundaries (I do), but we’re not getting a divorce anytime soon.

How do you push past creative roadblocks?

Needham: Usually just time—sometimes we’ll go a month without designing anything new and then it just hits us and we design six cards in one day. Also, looking at other favorite artists is really helpful. There are so many artists we admire, and checking out their Instagram is always inspirational to me.

Molesso: This is probably not the best advice for people in this situation, but I usually wait it out. It’s so hard to force something and it’s usually not your best work when you’re under pressure. So even if it might be last minute or nearing a deadline, sometimes you really just have to wait. Sometimes, when I’m in a creative rut, I take to Pinterest and go to Instagram and check out what all of my favorite artists are doing to get some ideas flowing. It’s always inspiring to see how other people are progressing their design style, and it inspires me to try new things and go outside my comfort zone.

What should couples know before they start a business together?

photography by cody guilfoyle

photography by cody guilfoyle

Needham: Make sure you really like each other and want to spend all your time together.

Molesso: Air out all your dirty laundry because committing to starting a business together is like getting married. Trust is really important, and when you’re putting your own money and your time and livelihood on the table, you should know for sure that this is what you want and that you feel comfortable doing it with the other person. Lucky for us, we got most of our fights out in the first year, and now that we’ve been together for a while, we have built up this type of relationship where if were disagree on something, we know that we will get past it.

What’s your favorite thing about working with each other? What’s the most annoying thing about working with each other?

Needham: My favorite thing is that we get to be together and it’s a unique bond. We get to share successes and excitement in a different way. Nothing is very annoying, so I guess the most important thing is that Ash will talk shop at inopportune times—like when I’m literally walking out the door to go to work.

Molesso: My favorite thing about working together is that if I tell Chess he did something wrong, I don’t feel bad about it. Because I know he’ll still love me. Also, if he ever gets annoyed with me, it doesn’t really hurt my feelings as much as it would if it were someone else, like a friend or regular business partner. I don’t mind criticism from Chess because I know he has the best intentions when giving feedback. The most annoying thing is that I wish Chess worked on it full-time with me.

This story originally ran in February 2019 as part of Partners in Design, a series that celebrates creative couples who work together. 

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