dylan gilligan upstate merch shirt show screen printing

Today we share an interview with a master interviewer himself, Dylan Gilligan, owner of Upstate Merch and founder of the Shirt Show Podcast. Dylan’s origins in the screen-printing industry are a bit different than the typical garage printer. Dylan was in a band and had a button company, he sold his buttons to friends and other bands. He then added T-Shirt merch and stickers to his business, a path that would eventually lead to a permanent place in the printing industry.

Dylan has been in the industry since 2006. He truly lives and breathes screen printing. From running a screen-printing shop to hosting a screen-printing podcast Dylan is incredibly passionate about our industry. Read our interview with Dylan to gain a wealth of knowledge in all things screen printing and entrepreneurship.

Interview Starts:

1. When you first started printing, what was your biggest struggle while learning the trade?

Dylan: I have never actually been a full-time printer. I started out doing sales. In 2006 or so I started a 1" button company. I was in a band at the time and was selling a ton of buttons to my friends' bands and that grew very quickly. I began to outsource Stickers and T-shirts as well. I was selling T-shirts so well that the company I outsourced to offered to buy my button company and move me to Atlanta, GA to become head of sales. I took the offer and worked there for almost 2 years. While I was there, I learned a lot about the actual manufacturing part. I really didn’t love living in Georgia and wanted to move back home to Upstate New York. When I knew I was going back home, the idea of Upstate Merch started. As soon as I got back, I hit the ground running. Upstate Merch started in 2009 in a one-car garage with a 6-color manual and a small Economax dryer.


upstate merch button sales

Dylan's Button Business Days


2. What is your favorite part about owning a screen-printing business?

Dylan: The craft. I love taking someone's idea for a design from concept to a full-on printed shirt. Creating a design, then doing the artwork separations. Determining the best way to print it. Halftones, drop-outs, what inks to use, if you put in additives or not, what squeegees to use, pressure, how many passes, etc... It’s an art form. 

 Screen Printing is an artform

Upstate Merch employee perfecting the art form


3. Scaling a business is difficult. What were your biggest obstacles while trying to grow your business? How did you overcome these obstacles?

Dylan: I think the biggest obstacle for any business is Employees. I was super fortunate to get to work with some of my best friends. They are my rock, my ride or die, but other than them is the challenge. Finding people who are as passionate about print as you are nearly impossible. You can find people who are fun to be around, hardworking, etc. but the truth is that these people are here to work and get paid. They get sick, have home issues, and have bad days. To be a good boss you need to realize that the people working for you are not just there to get a job done like robots. They have feelings, needs, and wants. You need to not only make systems and processes to make your business function, but you need to take care of your people. Listen to what they have to say and implement those things if possible. Feed them. Snacks are the key to long workdays. Let them listen to music to pump them up. Make sure you have a safe and clean environment for them to work in. It’s important.


Upstate merch screen printing business halloween

Upstate Merch crew dresses up for Halloween


4. How did you market yourself when you first opened the shop? How do you market yourself now?

Dylan: When I first started is when Myspace started. So, my entire existence was on social media. I was hitting up all the bands that would listen. Offering customer service first and band merch second. Find out what they really need and what the issues they have are. Then find a way to get them merch that works best for them. We kind of have the same approach now but on a much larger scale. 

Upstate Merch Print Shop

5. Can you tell us about a big mistake or large lesson learned in either screen printing or owning a business?

Dylan: The biggest mistake I have made in business was starting out as a partnership. I know it works for some people, but for me, it did not. I am a very driven person and I expect results. When I come up with a plan or idea, I intend to follow it through. 

6. Have you been able to maintain a work/life balance? If yes, how? If not, where do you feel you are struggling?

Dylan: Haha. This is a tough one for me. I feel like I do have a good work/life balance, but that’s only because work is my life. This industry is my passion. It’s what I want to do in my free time. If I’m not at the shop, I’m on my computer or phone at home doing research or something to do with screen printing. Obviously, I spend a lot of time doing stuff with my kids, but my phone is always there in my pocket. It’s an addiction and I’m in it deep haha. It’s all good though. I enjoy it.


7. If you were given $10,000 dollars to grow your business, what would you do first?

Dylan: Not to sound rude, but that 10K would go super-fast. If I got a free $10,000 to just invest in something, I would probably add it to my employees 401Ks. Or I would improve something in the shop for them. 


8. Any books or podcasts you would recommend to others just starting in the screen-printing business? Or just general business advice

Dylan: Obviously the Shirt Show podcast... You have to promote yourself. We get together each week and talk to either a shop owner, printer, artist etc. We dive into topics that relate to all printers. We are super open and truthful about all aspects. I think the best thing for a printer new or experienced is to hear that you are not alone in the struggles. We all have to go through it, and it never ends. As far as books, Profit First is a big one for me. I don’t use the actual Profit First Method, but it really kicked me into gear to be better with money. Some others that I love are Authentic: The Vans story, Greenlights by Matthew McConaughey, and Never Split The Difference by Chris Voss.

dylan upstate merch shirt show podcast


9. What is your favorite part of running a business? What is your least favorite part?

Dylan: The Freedom. I get to do whatever I want, whenever I want. My least favorite part by far is HR. Firing someone or dealing with fighting or personal issues I can’t fix.


10. Is there any part of your business that you feel you have mastered? Even if it’s not something you particularly enjoy doing

Dylan: I wouldn’t say Mastered for anything, but my favorite part is talking to customers. Especially the ones who are really excited to work with us. Going through the whole process and helping them get exactly what they were looking for. I enjoy the chase. Having a band or company you really admire want to work with the company you built. 


11. If you were mentoring someone starting a screen-printing business, where would you tell them to start? Dylan: What should they focus on to become successful?

Figure out who you want to print for and why. You need to have a focus. If you are just getting into printing and you are targeting anything and everything it will be super difficult. Yes, you will get customers, but they won’t be loyal, and you will never know where they are coming from and why. If you don’t know why then you will have a ton of ups and downs. The hardest thing to do is scraping by in the slow months with your employees staring at you wondering what they will do today. If you have a focus and a niche, you can immediately sit down and sell to those customers. You can talk to them with complete confidence because it is a market you know well.


12. What is your shop management style? Do you run a tight schedule and stick to a pre-organized plan, or do you see where the day will take you?

Dylan: We are super organized. My management style is for me to figure out the original processes, then hand them off to someone who can manage that area and put their own spin on it. You need key people who take ownership of that position. Once you trust in them to get the job done, they will get very prideful of that position and see that it is done. With all those people in place, the shop runs as it should.

upstate merch screen printed t shirts

Fresh and finished prints from Upstate Merch


13. Anything else you would like to share with fellow screen printers or people curious to learn?

Dylan: The only thing I can say is MAKE SURE YOU LOVE WHAT YOU DO. Treat screen printing like a skilled trade. It is a craft. Be passionate about it and make sure your focus is putting out QUALITY WORK. If you are getting into this for a quick buck and you want to cut corners, don’t talk to me. You ruin it for the rest of us. Thanks!

Interview ends

Thank you, Dylan, for letting us pick your brain. We know this information will help many printers out there looking for the right motivation and place to start.

Dylan’s drive and hustle is clear to see even at the beginning of his screen-printing journey. He is a self-made entrepreneur and enjoys the chase, something many find hard in operating a business. While he has already accomplished much, we know only great things are in store for someone with this type of work ethic. If you want to hear more from Dylan tune into his podcast the Shirt Show, as he dives into all things screen printing and entrepreneurship, you won’t be disappointed.


Podcast: Shirt Show

Instagram: @upstatemerch

Website: https://upstatemerch.com/


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