How I Started A T-Shirt Company

Jan 27, 2022 | Programming

This is the story of how I started a t-shirt company with my wife. The company lasted eight years under us and in 2017 we decided to sell the company. This is the story of how we made it all happen.

On a lark my wife and I started a t-shirt company based on the famous Chicago tamale guy back in 2009. Over the course of eight years we grew the company into a modest business generating just above $600,000 in yearly revenue. Our t-shirt company went through a few major iterations and pivots before we hit our stride. Eventually we decided selling t-shirts wasn’t our thing and we sold the company to people who were better at this sort of thing than we were.

As part of my writing to become a better writer exercise, this is the story of how we created a t-shirt company from the ground up. Half of the story is about our journey, the other will detail how to create a t-shirt company for anyone looking on where to start.

The Beginning

I’m a software developer through and through. It’s what I’ve been doing since I was 14 and there hasn’t been a time in my life since 14 that I haven’t been doing coding in some way or another. Starting a t-shirt company was not something I knew very much about. Neither my wife or I has any background in retail, clothing, graphic design or anything that is beneficial to starting a t-shirt company.

The idea for our t-shirt company started while we were living in Chicago. Over the course of going out in Chicago you get to know the tamale guys, or The Tamale Guy – a wonderful man who sells tamales at different bars in the city throughout the night. There are a few different tamale guys doing the rounds, but everyone knows the real tamale guy is Claudio with the red cooler.

After a while we became regular tamale guy customers and maybe even close acquaintances. One night, my friend thought it would be fun to make a Tamale Guy t-shirt. There’s no magic behind the idea, it was one of those ‘this would make a great t-shirt’ type of ideas. But knowing how popular the tamale guys are in Chicago, we ran with the idea. We didn’t know the first thing about making a t-shirt, but it sounded like a fun idea and figured other people in Chicago would want a Tamale Guy t-shirt as well. Over beers and tamales we came up with a business plan on a bar napkin to design, print and sell 50 tamale guy t-shirts online.

Our t-shirt selling plan looked a little something like this:

  1. Start a new side hustle selling t-shirts online. Keep our day jobs and do this as a kind of hobby project.
  2. Create a LLC to operate the business. We used LegalZoom but you can save some money if you want to do it yourself. Check with your state on the specifics of creating a LLC.
  3. Hire a designer to create your design. We hired a local Chicago designer to create a design with a little red cooler with happy, smiling tamales peaking out from under the lid.
  4. Get in touch with a local print shop to print the t-shirts. You can use an online marketplace to print your shirts, but its better to have a local option you can get to know and do print checks in person.
  5. Figure how you’re going to do your shipping. ShipStation integrates well with Shopify and a thermal label printer. After a little bit of set up, you can print shipping labels from all your orders with a simple click of a button.
  6. Set up an online marketplace to sell your shirts. Today I’d recommend using Shopify, but we used an existing WordPress site that I already owned – Because of the existing domain we decided to name our t-shirt company Scared Panda.
  7. Tell everyone we know about our new t-shirt company. We sent emails, tweets, texts and posted online anywhere we could.

Believe it or not, we sold out of that run of 50 t-shirts in the first couple of weeks. We had definitely found something that people liked. It turns out, people liked the idea of a graphic t-shirt that celebrated their town in a subtle/kind of cool way. At the time, 2009ish, I only knew of a few “city pride” t-shirt companies. The big ones to me were CLE Clothing in Cleveland and Dirty Coast in New Orleans. What was happening at the time was a push for locals to create insider t-shirts about their city. We jumped on the idea and started to create more Chicago themed t-shirts. Utilizing the power of blogs we were able to get our t-shirts in front of our target market. Things were going pretty great and we were excited to see how far we could take this side hustle.

New York

Just when we were really taking off with our Chicago t-shirt company I got a job offer in New York. I’d always wanted to live in New York but I also didn’t want to leave Chicago. What to do!? We decided to move to New York – how could you not? Even though I was born and raised in Minnesota, Chicago had become – and in a lot of ways still is – home. Deciding to move from Chicago to New York was one of the hardest decisions of my life. Anyway, we found an apartment in the East Village and moved in March of 2011.

I could write paragraphs and paragraphs about living in New York. But that’s for another blog post. This post is about starting a t-shirt company. In New York we had the opposite reaction to our t-shirts as we did in Chicago. We tried to pivot into the New York t-shirt market by making NYC specific tees but they never really took off. Nobody in New York seemed to care about tees about New York. Or at least they didn’t care about ours.

I think the main reason we failed at this t-shirt venture in NYC was that we didn’t have a strong connection to the city. To make a good t-shirt, or good product, you have to have a passion and a good understanding of the subject. We didn’t have that in New York and it showed through our t-shirts. After hustling at markets in Brooklyn and Manhattan we started to think that maybe we didn’t want to spend all our free time slinging t-shirts. After all, we were living in one of the greatest cities in the world. We should probably use our time off from our real jobs to enjoy the city.

Then one day our good friend from Chicago was visiting and said “Why don’t you make t-shirts about Minnesota? You could make one that just says ‘Minnesota Burrito’ but make it a hot dish”. I remember this day as clear as yesterday. We were having a beer at the Spring Lounge and suddenly we had an entire new way to go with our t-shirt company. We were from Minnesota and knew the deep passion Minnesotans have for their state. Have you ever met someone from Minnesota who didn’t love Minnesota? Minnesotans love Minnesota.

We designed a couple of Minnesota-centric t-shirt designs, had them printed and started selling them online. These were ones that really spoke to us as Minnesotans and we knew that they would resonate with the locals as well. We contacted local Minnesota bloggers and other people that could reach our market. I remember coming out of the dentist in Midtown one afternoon and seeing just about all of our Minnesota t-shirts had solid out after an email blast from Mpls/St. Paul Magazine. This was the sign that we were on to something and we began making plans to move home and open a Minnesota t-shirt company.


It took a few years but we eventually figured out the type of t-shirt company we were going to run. After the talk in New York, my wife and I decided to move home to Minneapolis. Neither of us wanted to leave New York – the plan was to either stay in NYC or move back to Chicago at some point. Neither of us – well me, mostly – ever expected to move back to Minnesota. But at the time I was burned out of in the software industry and wanted to take a break. Moving home to Minnesota to start a t-shirt company sounded like the break I needed.

After the success of our initial run of Minnesota t-shirts we had seen what we were seeing in Chicago – t-shirts that resonate with people and are hyper local were popular. It wasn’t that we were making cool designs, it was that people felt a connection to our product. This is the key to any business, when people feel that connection to your product they are more likely to buy whatever it is you are selling.

For us it was uncovering that deep love of Minnesota that Minnesotans have. And we did that with different sayings, slogans and images that made people feel connected to our designs. Anyone can put the outline of the state of Minnesota on a t-shirt. But what made us successful was that if you were not from Minnesota you might not totally understand what the t-shirt was about. This was like an inside joke for our customers. Something people could wear around the country and get asked about.

After setting up shop in Minnesota we grew faster and faster. Eventually quitting our full time office jobs to work on the t-shirt company. I was always doing consulting on the side, but for a two years my day-in and day-out job was slinging t-shirts.

The End

In 2016 after two years of full time t-shirt hustling we were getting tired of the day to day work. Part of the excitement for us to start a t-shirt company was the hustle to see if we could pull it off. After a while we and after that “oh, wow. this thing actually works” feeling wore off it became just another job. We both missed the structure and regular paychecks from our old working lives – we also had a little baby on the way. So, we hired a business broker and put our little t-shirt company up for sale. The day after the business sale I started my first day as a full time Technology consultant and have not looked back since.

If you made it this far, I hope you enjoyed this little story. Well, looking back this post is more of a brain dump than a “how to start a t-shirt company” story. If anyone reading this has an itch to create their own t-shirt company or wants to ask a few questions – drop me a line at or use the contact form.


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