In this episode of Shirt Show, host Dylan Gilligan shares his own story for the first time, with Guest Host Dewey and Shirt Show Producer Christina stepping in to ask the questions. The conversation explores Dylan's path from early business missteps to founding Upstate Merch and eventually creating Shirt Show. It’s a practical, behind-the-scenes look at lessons learned, mistakes made, and how persistence paid off.
STARTING FROM SCRATCH
One of the most pivotal moments in Dylan’s story came when his only vehicle was repossessed. Despite running a growing business, gaps in the backend like insurance, financial tracking, and compliance all seemed to catch up with him.
This moment pushed Dylan to shift gears and focus on running the business properly. That meant understanding taxes, workman’s comp, and sustainable operations.
“I knew how to get an order, print, and ship. But I didn't know the business side at all.”
This is an all-too-common scenario for screen printers.
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PARTNERSHIP AND LEADERSHIP
Dylan talks about the process of ending a business partnership that was no longer working. The change opened up new possibilities and gave him space to reimagine how Upstate Merch could operate. With clearer roles and more accountability, the business was able to grow.
“It was like running with a weighted vest and then taking it off,” he says of the experience.
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TEAM EFFORT AT UPSTATE
Dylan is quick to point out that Upstate’s success isn’t a solo effort. Longtime team members Bill, Chris, and Brian have helped shape the shop’s culture and drive performance.
“Upstate is the culmination of all of us,” he says. “I might be the owner, but they're just as invested.”
WHY SHIRT SHOW EXISTS
Shirt Show started as a fun idea, part podcast and part print community outlet. Dylan describes it as his version of Wayne’s World for the print industry. Over time, it’s become a resource for printers to learn, connect, and grow through shared stories.
From interviews to Discord chats to in-person meetups, Shirt Show aims to make screen printing more approachable and collaborative.
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WHAT'S AHEAD
The goal moving forward? Keep things simple. Dylan wants to continue building meaningful experiences, whether through content, education, or events. He doesn’t have a five-year plan, just a commitment to keep showing up.
KEY TAKEAWAYS
- Failure doesn’t mean you're done. It can be the turning point.
- Growth requires systems, not just hustle.
- Partnership dynamics can impact performance. Evaluate what’s working and what isn’t.
- Invest in your team. Shared ownership creates long-term stability.
- Focus on service and connection. That’s what builds community.