After working for Jess and Dy-Min as their creative assistant for Not Sorry Apparel for close to 6 months now, I knew I wanted to interview them and pick their brains on their experiences in the Detroit small business world and how they navigate it being women entrepreneurs. Oh boy, did they have a lot to say and great advice for anyone who dreams of jumping ship and building a start-up.

How long after you made the crop top did you realize this was something more that you should pursue?

Dy-Min: I’ll start by saying we probably shouldn’t have pursued it because the first time we tried to get them made the person took all our money. We got lucky just to get the clothes back because we weren't printing our own stuff at the time. We weren't even a business at the time, we were doing it for fun. Why we thought that would be fun? I don’t know, but I feel like every group of friends has a saying that they think would look funny on a shirt and we actually executed it. Jess, you can tell them about Eastern Market After Dark - the first time we did it.

Jess: Yeah. A couple months after we had conceptualized the crop top and finally got them printed we sold them at our friend’s party during Eastern Market After Dark and people really loved the design.  It was the “Kill ‘Em” Kellogg bootleg design. Since it was a crop top dudes were not really into it but they wanted it on a tee. Dy-min went to a fashion conference very closely after that.

Dy-Min: I met with Karen from Detroit Sewn after the conference. They were one of the only cut-and-sew spots in Detroit at the time and were also in start-up mode. They had just gotten a building in Pontiac and were ready to start taking on business. So, I remember Jess and I had these super shitty sketches that we took up to them during our lunch break - because we were both currently working in marketing in the suburbs. And we just thought we were going for a tour and they sat us down and were like, ”Here are some quotes, you let us know what you want to do.”  And we were just like, “Oh you would make this? This is for real?”

Jess: Yeah we didn't really give ourselves time to talk ourselves out of it which I think was really important. I think we had a good feeling about it too because so many things were working out and happening naturally and we decided to just see where we could take it. But soon thereafter we ended up incorporating because really, you take things as seriously as you want to, and that was us really committing it to ourselves. It's like we can either have this be a cool side project or we can legitimize this, make it an LLC and really dive off the deep end.

How hard was it balancing this passion project and a day job and what advice would you give to other people who are in the same position and want to perhaps quit their day job?

Jess: At first Dy-Min was working full-time at Not Sorry and I was working outside and now that the roles are reversed, we have a newfound respect for what each other were doing and are presently doing. I don’t know how people who are sole proprietors and are running a business alone. It's not easy and there’s not really a work-life balance, but more of a cohesion. It's more integrating life and work in a way that’s not overwhelming. Sometimes it will be overwhelming and that’s okay! You have to just make sure you’re reflective and think back about where you started, that usually does the trick for me. Like a year ago I was sitting in an office and not truly happy like I am now. So that gets me out of my funk when I'm having a bad day.

Dy-Min: Definitely agree with Jess because even when I was doing this full-time we were in a new location and we were a new brand and there was just a lot of stuff we didn't know. So one thing I didn't know was that it would take time to start making money. I just thought  the doors are open, the money’s rolling in, we’re rich! And that’s just not how it works so even then I was doing side jobs; I was doing Lyft. So I would wake up at 5 am go Lyft, try to print in the basement, go to the store and work till whenever, go home and repeat. If it was the weekend, I would Lyft any free time I had so I could make more money. It was just not sustainable. I guess I’ll get personal because this is a personal interview. I think it’s been really good because when I have bad days like today, which was not a great day at work, I still know I have options and I remind myself of that a lot. Most of the people I work with just go to work and go home and sometimes I'm envious of that because that sounds amazing- but that's not my life right now. When I have a shit day at the office I know I won't be there forever and there’s something else brewing. 

Jess: Yeah I would say it sounds really glamorous to jump ship from your steady job and pursue your side business full-time, but I recommend trying to work both or have something financially stable as you are building up your brand or your business. Knowing when to jump ship is really important too. Last year I knew I needed to save X amount of dollars before I jumped ship and I saved up that money, maxed out my 401k and started a general index fund. I was feeding money into these so i’d have some money for when I jumped ship. I didn't want to have to worry about paying myself right away. I made sure I had enough savings for 8-10 months and my goal was that we could start paying ourselves before I ran out of that money. We got to that point and it was great. I still had some money left over in that account and just cashed it all out for the house we (editor’s note: Jess and her husband, not Jess and Dy-Min) just bought. Making sure you have a game plan for the transition is super important. Also, look into general index funds because they are very low-risk, low-cost investment funds.

Has it been easy or difficult because you guys didn’t have a long existing friendship before you started your business?

Dy-Min: I think easier, because I feel like I have great friends but sometimes when you know someone for a decade you know too much about them, like “oh I know you’ve fallen through on multiple projects…”

Jess: It's kind of how you should never live with your best friends or do business with family—that kind of stuff can get sticky fast. If you have too much of a deep relationship that can hinder creativity  and emotions can get overwhelming. We definitely had mutual respect for each other… we’d known each other for less than a year but we both have very good intuition and when you start working with someone you know pretty quickly if they’re on your level. The fact that we were both committed to meeting and bringing ideas to the table demonstrated that we could grow a business together.

As women entrepreneurs in the business setting and meeting other entrepreneurs do you think people have looked down on you or your business because your women?

Jess: I feel like men in fashion don’t get asked “Oh so like are you a traditional seamstress, did you learn how to sew, did you go to fashion school?” Like what are your credentials that make me qualified to do this like i'm not already doing this! I don’t hear guys getting asked that kind of shit ever or like, “Oh you screen print your own stuff?” I’m sure Dy-min gets asked all the time or “Wow you do all your own designs?! You guys do everything in house?” Like they're blown away when they find out we make everything you see. They also don’t believe it’s two people. But also I feel like people are like, “Oh Dy-Min’s your partner?” and I’m like why do you think that?

Dy-Min: Yeah dynamics are always so weird, depending on who you meet they're like, “Oh you work for Jessica?” and I'll let that shit slide sometimes because I want to hear more what of what people say. I'm not offended, I just listen and gather information. It’s small things like that show me you're not as smart as you think you are, so keep talking. People who think they are on a different level from you tend to talk talk talk and I get information all the time. People sometimes act like, “well she's like the screen print bitch,” and I'm like tell me more. Then later they're like I probably shouldn't have said that and I'm like yeah probably not.

Jess: I feel like I get a lot of advice from dudes that are not even in the industry. For example, this random guy came through our studio and told me that my workstation table was not sturdy enough for my new machine. And guess what? We haven’t had any issues with the machine, and its been working fine.

Dy-Min: And I was like who he is, how does he know…

Jess: Who’s this jabroni...

Dy-Min: What does he do, why is he relevant, does he embroider?  And it’s no to all the above, he was just on a fucking tour. What do you know?

Jess: I’ve also heard couples come into the store or a pop up and the girl will really like our stuff and the guy just says, “babe they just screen printed on second hand clothes.” Some people just devalue what we do and it’s obvious that the bro is just jealous he didn't think of it. 

What’s your experience been like navigating the Detroit small business community and do you think the investments in the “renovation” of Detroit and influx of development has helped small businesses? 

Dy-Min: I think it depends on who you ask. We know plenty of people who are doing great and also plenty of people who are about to get kicked out of their store’s because the rent went up after the property was sold. I think it also matters what you sell. I think there are a lot of places here where the price point doesn't even match the income of the people that live in the city. I can see both sides of it and I think that’s why Not Sorry Apparel exists because this is real sustainability that people can afford. You can go shopping and get cute with us while feeling good about it. And our goal...do we want our own location? Yes, but does it have to be downtown? No.

Jess: I think once you are beholden to a landlord that you can’t control, you're kind of playing a game. Especially in Detroit right now prices are definitely inflated and we’re probably going to have a recession soon that will bring everything down (just because Trump, tariffs, tax bill etc.) The dream is to actually own the land because that's where the real power is. You can really build something that's bigger than you, and it doesn't have to be a store. You can re-imagine your space to host workshops, beta test new designers, foster start-ups and have manufacturing space where you're actually building a team right here that’s working for you instead of getting drop-ship stuff. That’s what we see as the sustainability arm that people miss. It’s very sustainable to keep things homegrown because all that money stays in your community. If we can contribute to that by hiring locally and keeping our footprint small, that’s part of our sustainable vision for the future. To go back to your point, I think we’ve definitely benefited from the resources in Detroit that other cities don't offer. For example, I’m originally from Miami and they don't have startup resources through the city. In Detroit there are programs where you can take business classes, free workshops and more. They’re willing to teach you how to host a pop up or start a brick and mortar, different stuff like that. If you do follow through with those courses you can usually get some technical assistance which basically means they’ll pay for accounting or legal fees, a website developer, etc. We did Techtown’s Retail Bootcamp when we first started and that got us into the Cass Collective, which was our first retail experience with the brand. Currently, we have a studio in Ponyride which subsidizes manufacturing space for small businesses so they pay way below market rate. Yeah we’ve definitely benefited from it, but we also know what is not sustainable for us and what to avoid. The hot spots in downtown are sweet but is it worth the money? I don't think so. I think if your product is good and your intentions are good and you build that relationship with people, they’ll come to your store. It can't be in the boondocks but it doesn’t need to be downtown to be successful. 

How do you think you’ve impacted the “Detroit” brand so far?

Dy-Min: People feel included which I think is super important. I feel like we give visibility to people who don’t usually have it and that’s the main thing that attracts them to the brand. They’re like, “yeah I am not sorry for this” whether it’s our Detroit shirt, black shirt, queer shirt, whatever. So many brands are all about being super VIP or exclusive, and I feel like we’ve figured out a way to be exclusive and inclusive which is why people fuck with it. There are plenty of people who don’t like it and that’s the Detroit way, we love it. People here either love you or they hate you and there's no in-between but that's what you want as a brand.

Jess: I respect that, I like when people passionately don’t like it. Yeah that’s your opinion that’s totally fine but usually when you explain the meaning people are like, “oh that’s cool.”

What do you say to people who say it’s counter-intuitive to say you’re not sorry for something?

Jess: When I was moving here from Miami, all my friends and family were saying they were  so sorry I had to move to Detroit and I was like, “I’m not sorry I fucking love it here.” I had already been here and visited several times- I really liked it. I had a vision of what I wanted to do when I moved here and I’ve been able to make that all come to fruition. I still feel not sorry, moving to Detroit is still the best decision I ever made. But to go back to the culture thing, I think people get off seeing their friends in videos and pictures with brands and it just makes it feel more community-minded. It’s not like we’re using these professional high-end models, they're real people. We want it to be for everyday people, so why not use people who are gonna wear this everyday? I love when people see their friends in our pics and just gas them up in our comments like, “oh I see you doing your thing!” And that makes me really happy to see people supporting their friends and each other.