Jamie Chambers is a 29-year-old small business owner and bartender in Chicago, IL. When she found herself unemployed in 2020, she got creative, starting her own alternative apparel company. We spoke with her about becoming an entrepreneur and her interest in tattoos.

I grew up right outside of Chicago and started taking the “L” when I was about 13 years old. My parents were very free-range; they trusted us to do what we wanted to. We would take the blue line to Logan’s Square or downtown, and I’d go to punk rock shows in Chicago with my older brother.

When they were actually happening, definitely! My hobbies were going to see live music and to new restaurants and cocktail bars. Getting dressed up was my favorite thing to do, and now I’ve been donating so many things because there’s nowhere to wear it!

Back in March, I had just gotten a new job, and it was amazing. It was like my five-year plan: I wanted to move up to corporate and manage a whole restaurant downtown. Two months in, everything got shut down. I got a new job in September, worked for two months, and got shut down again.

So this summer, I’m like, okay, I have this following on Instagram that the average person doesn’t have. I have 40,000 followers. I have a niche platform of alternative tattooed girl who wears a lot of makeup. I’m into fashion. And I think I could run a business. I have the know-how, I can navigate my way around basic business things, and I understand numbers and communication.

I figured I can probably figure out how to make clothes that I would like to wear that don’t exist out in the world yet. It started off with me just wanting to do a couple of T-shirts, but I’m an all-or-nothing kind of person. That’s how Cold Hell became a thing.

Winter in Chicago is a cold, cold hell. I wanted a name that was edgy, but also represented where the clothes are coming from.

I do. I love drawing and my brother Neal is a tattoo artist. He’s the General Manager of Tatu Tattoo in Wicker Park, which is a really well-known shop. My dad is a cartographer and was a cartoonist. The drawing gene has always been in our family.

My brother’s been helping me a lot with how to draw and draft and get it onto a computer and then somehow turn that into a design that you can transfer to a t-shirt. So it’s my designs, but Neal is always helping in the background, and so is my boyfriend Sean, who is also an artist. I’m constantly asking them, how does this look? Would you wear that? How can I change this?

Anybody that works with the general public will get that sentiment. As a bartender, it’s our job to make people feel comfortable and listened to, but at a certain point, it can suck the life out of you. I believe in boundaries, and mental health is really important. It’s kind of a tongue in cheek way of saying I have boundaries, do not cross them, and here’s my nice little shirt that says it so I don’t have to.

A lot of hairstylists and exotic dancers are buying these shirts. I actually have a lot of therapists buying the shirt because of the irony, which is really funny.

What’s next for you and for the company?

I want to go back to school and get my degree, believe it or not, in psychology. Like I said, mental health is a huge part of my life and something I practice daily.

I can see myself bartending while finishing my degree, but the business is my long-term goal. I’ve been working on collaborations with different artists. I’m designing new things every day and finding ways to make my products better, more accessible. I’m coming out with phone cases soon and I’m doing weird things like shower curtains. Why not? If someone wants to buy a shower curtain with whatever on it, go for it. I have it.

 I remember drawing tattoos on myself when I was 13 years old in Spanish class and getting in a lot of trouble. I was this little punk rock kid. My idols were like Brody Dalle of the Distillers. She’s covered in tattoos and she’s so hot.

Then Neal became a tattoo apprentice in Chicago and gave me my first tattoo when I was 17. He did Sailor Jerry roses on my ankle. I felt like everyone was looking at me, and of course, no one is looking at my ankle, but I just felt so badass. That set it off. Neal got to build his portfolio really quickly because I would just come in and get whatever tattooed.

Most of them. I get them for free, and I don’t think I would have as many if I had to pay for them. I also trust him ultimately. He did my chest piece a couple of years ago, and I could tell he was being very meticulous and super gentle because it’s his little sister. He took it seriously and it came out exactly how I wanted.

My style is comfortable and minimalistic and that’s what I wanted on my chest. It was also around the time that I realized that I’m not going to be working for the government or anywhere that wouldn’t be okay with me having a chest piece. It was kind of a commitment to myself like, you know what you want, so just go for it. Get something beautiful and feminine that looks like jewelry.

It was the most painful tattoo I’ve ever endured. It’s not technically finished because we never shaded the flower in the center, but I’ve been happy with where we stopped it.

It’s funny, I have a lot of tattoos, but I hate getting tattooed.

I usually eat a big cheeseburger beforehand because the blood rushes to your stomach to digest your food. It’s just like taking a Xanax without taking drugs. Then I just kind of zone out and go into a separate place in my head.

My chest piece is my favorite. I also have a black cat by Vince LeBlanc at Animal Farm Tattoo. It’s my cat Rajah, and he’s holding a little valentine for the rats. I’ve always owned a cat and usually, it’s a black cat. They’re the cats that get left by the side of the road and put up for adoption most often because they’re associated with bad luck. This is kind of my anti-bad luck charm.

The tattoo is just really beautiful and bright and colorful. It’s on my forearm so it’s in a good spot. Aesthetically I love it, love where it is.

You’ve kind of talked about this, but traditionally, tattoos weren’t seen as “professional”. What’s been your experience as a new business owner with tattoos?

I also work at an oddities shop called Sideshow Gallery, which is owned by two super metal, tattooed, badass women in their 40s. I was already working there when I started my company, and so I had them as role models.

When I do business with people I’m assertive without being aggressive, and I’m always prepared. I want to be taken seriously. I want to have answers to questions and to have good questions to ask. It all comes back to just fake it until you make it, be respectful, and it usually it works out.

Eventually, I’m going to have to communicate with manufacturers overseas. That’s when I think it’s going to be a little more interesting for a young alternative woman wanting to create these things with people who may not understand that.

My first question back is usually “What do you plan on doing?” But I’ve realized that doesn’t matter.

I usually cover up my tattoos when I interview. I just like to have people know who I am first and foremost. I want to show them how smart I am or what I’m capable of. My advice is to be as qualified as possible for the job, and the tattoos will be a second thought.

Always. That was my mom’s quote too. She was a colonel in the army. She was one of the first women ever to train with men in the army. I definitely had a unique upbringing in that regard. It’s always been like, I will make a space for myself here.

That’s something women sometimes forget  – you have a right to this space, so make it your space.

And if people aren’t letting you, then just keep bulldozing through, because that’s what the guys do. You can do it too!