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SHIRT SHOW

Author: SHIRT SHOW

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Shirt Show deep dives into all things screen printing and apparel decoration with shop hacks along the way. Hosted by Dylan Gilligan of Upstate Merch.
296 Episodes
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Learning Adam & Kato Machin's print journey was a breath of fresh air, because it is truly unique. Prepare to find out how a wardrobe stylist and a tattoo artist joined forces in Brooklyn, fell into printing in upstate New York, and operate Thunderhouse Prints in Reno, NV. Spoiler alert- It's a bumpy ride. Topics of discussion include: Back injuries, impulsive decisions, learning on the fly, asking questions and being coachable, proofing your shop for hardship, becoming your own moving company, near death experiences, live printing, ghost tours, and turkey necks.
Still recovering from ISS Long Beach, but the show must go on! If anybody is able to inspire you to shake off the jet lag and exhaustion, it's Jaime. He's simultaneously worked not only multiple jobs, but multiple CAREERS over the last nearly two decades. Now that he's finally gone ALL IN (or 'unemployed' as he likes to say) we had to get the full story of the wild journey he's been on with At That One Shop. Topics of discussion include: Finding your support group, shirt kiosks, working multiple jobs and side gigs, handling failure, going all in, growing from a manual garage setup to a shop with autos, starting all over, reevaluating your life and business, and return policy loopholes.
One does not simply print water-based in New Zealand, but Chris & Jon aren’t afraid of a challenge. With nothing but love for their craft in their hearts, these two Kiwis started as modest hometown printers, and journeyed their way to becoming heads of an international printing operation. Topics of discussion include: international shop visits, importing their inks, how water-based printing helped differentiate themselves from their competition, landing their first client, organic growth, small town living, elevated packaging, custom socks, promo products, working with international manufacturers, developing tech and fulfillment capabilities, company culture, employee benefits, business coaches, specializing staff roles, expanding into Australia, and a most unfortunate courier disaster.
Star Cadet is a creative commerce company. Its mission is to deepen the connection between creators and their communities, and its captain is Rachel Rogers. After helping her husband, Olan Rogers (OG sketch comedy YouTuber) connect with his audience outside of the comments section, Rachel’s crash course experience in the merch world has launched her into a series of endeavors that would make even the boldest of the bold shake in their little space boots. It’s been a bumpy ride, but the journey is out of this world. Topics of discussion include: gratitude journals, mental and physical health, real world education, corporate retail, freelancing, the hybrid retail experience of The Soda Parlor, working with Conan O’Brien, dissolving partnerships, getting hit by a tornado, brand building, creating meaningful connections, brand licensing deals, the realness of YouTube, the love/hate relationship with social media, Mondaes, and running your business with integrity.
We came hot out of the gate on this one, diving into discussion around finances, and the step by step processes we develop over time as shop owners. But we were sure to circle back and get the story of how Kyle went from pursuing fine art printing to landing in the shirt world, and eventually bringing Annie into the fold full time. Topics of discussion include: Starting projects during downtime, navigating large and tedious orders, pricing structures, dialing in finances, offering benefits, eco-consciousness, cease and desists, moving into a fixer-upper shop, leaving the steady career path behind, having a change of heart with DTF, a very unfortunate box cutting technique, and the unsung lengths taken to satisfy customers.
The turns have tabled, and our very own host has become our first guest of 2026. With Dewey Halpaus as our guest host, and Christina riding shotgun, bear witness as they pry uncomfortable truths, uncomfortable highs, and uncomfortable-er lows out of Dylan’s life journey. Please note, all this discomfort stems from Dylan’s visceral reluctance to talk about himself, and to be a spectator of this event is uniquely joyous. Like a demon being exorcised out of a possessed child, there is sweat, cursing, and a sense of euphoria waiting at the finish line. Topics of discussion include: Small town childhood, working odd jobs, coming up in the New York hardcore scene, finding screen printing, starting Merch Buttons, selling the button business and moving to Atlanta, learning sales, starting Upstate Merch, early business mistakes, partnerships, getting involved in the industry, how your favorite podcast came into existence, the future, listener questions, and the complete list of movies that make Dylan warm and fuzzy inside.
After purchasing a small print shop on a whim, Brooke spent the next 20 years living, breathing, and growing All American Screen Printing. After two decades, she has since sold her shop, and has stepped down to a production manager role. Brooke is here to provide insight into the nagging question that plagues shop owners around the globe- What if I just sell it? Topics of discussion include: getting consumed by your work, the dynamics of working with your spouse, first hires, misprints, life after selling your business, knowing the value of your business, implementing SOPs, and conveyor belt rides.
Dom and Ryan have both been on Shirt Show in the past, but never as a duo. We’re catching up, getting the story of how these two joined forces, how they’ve handled the rapid growth and transformation of Superior Ink, and what their sights are set on for the future. Topics of discussion include: roulette, the visionary and integrator combo, restructures and investments, leaving Denver, rebuilding your crew and culture, shifting your focus from the big picture to everyday life, imposter syndrome, shop layout and green houses, small town living, finding your purpose, helping your community, the commonalities between all shops of all sizes, tech integration, and being grateful.
John (@theglorifiedcarpenter) may work outside our industry, and podcast outside of our industry, but the similarities between the carpentry business and the printing business is insane. It’s funny how we can almost relate MORE to those who aren’t elbow deep in ink, and their perspective is just as valuable, if not even more. This 2.5 hour discussion is proof, and we think you’re gonna love it. Let us know in the comments or slide into our DMs and share your thoughts! Topics of discussion include: Scrappy attitudes, low bars of entry, skill building, hiring and firing, knowing your value, finding your community, inspiring quality work out of your team, the dangers in over-optimism, starting over, taking stock of what you have, figuring out what’s next, getting into the weeds of podcasting, and Lego side hustles.
Nick was on the same print message boards as Dylan back in the day, long before his shop Threadbird took flight. Though they hadn’t officially met before, the parallels between Nick and Dylan’s print journeys resulted in a conversation akin to old friends reminiscing on the good ol days. No matter your niche or market, life throws a lot of the same curveballs at us all, and it can be tough not to white knuckle through talks of what tomorrow may bring. This is a good one. Prepare to relate, and feel seen. Topics of discussion include: Grappling with December, early internet, accidentally becoming a band manager, getting into e-commerce, venture capitalists, wanting to do what you love, getting burnt by bands, shirt giveaways, brokering, how we plan on approaching 2026, education, market pivots, outsourcing, company score cards, and Mr. Fusion.
Zach is a mechanical engineer turned 4th generation dry cleaner. After breathing new life into the family business, Jeeves New York has expanded beyond high-end dry cleaning, and into educational TikTok stardom. They’ve since written a book titled ‘The Laundry Book: The definitive guide for caring for your clothes and linens’, and are here to bridge the gap between those who print shirts, and those who revive them. Topics of discussion include: problem solving, what dry cleaning IS, the decline of garment quality, high-end and fast fashion, wash care symbols, best laundry practices and detergents, dye migration, and Met Gala goals.
Dewey Halpaus is a fellow podcaster (Peer Pleasure) who recently started cutting his teeth in the screen printing game after falling in love with bootleg tees. This episode is full of joyful commiserations and fun stories of Dewey’s journey from rock star(Anatomy of A Ghost/Portugal. The Man), to plumber, to podcaster, to printer with Light Thriller. Topics of discussion include: The purity of the podcast format, growing up in small town Alaska, meeting U.S. Presidents, DIY music scenes, the peaks and valleys of the music industry, bootlegs and tribute tees, the importance of a van, the fear of failure, city vs country living, networking, enjoying the journey, grieving, and Safe Men.
Andrew & Chantel Boyd are the dynamic duo behind Boyd Creative. Not only do they specialize in printing tattoo designs, they operate like a tattoo studio as well. Choosing quality over quantity, every day. Topics of discussion include: Product photography, learning from different shops, career pivots, tunnels, niching down, conventions, leave behinds, burnout, mental & physical health, some solid shop hacks, and bad movie endings.
After going viral for pushing ink through a vinyl cut stencil, Jennifer’s custom t-shirt hobby became a business. With Pigskins & Pigtails, Jennifer is bridging the gap between full fledged printers to hobbyists and crafters, and sharing screen printing with the world at an extremely accessible level. Topics of discussion include: Keeping operations simple, fielding brand deals, putting yourself out there on social media, building community, business collabs, best content practices, and finding inspiration in the wild.
It's been 246 weeks since Rik was last on Shirt Show, and a lot has happened. After overcoming a near death experience earlier this year, Rik was kind enough to share his experience with us, as well as his newfound perspective as a small business owner who kept his shop running while he was down. Topics of discussion include: having your kids work at your shop, powering through a medical disability, holding sneezes, preparing for the worst, SOPs, centralized file storage, hiring setbacks, moving, Every time I Die, and questionable family movie nights.
Brought Nick back on the pod again to get a clearer picture of what using Print Profit looks like in the REAL WORLD. Not just a best case scenario sales pitch. 2025 has been such a weird year and 2026 is just around the corner, so our numbers feel more important than ever, and Nick is trying his best to take us all to profit land. Topics of discussion include: understanding your costs, setting goals, common miscalculations, industry trends, easy first steps to take to get your numbers in order, and group think.
Chris got bit by the print bug at 14 and has been printing ever since. After coming up through school, and a trial by fire stint of working production, he went out on his own and has been crushing it ever since with Tonal Range Ink. Topics of discussion include: graphic design degrees, cmyk printing, fads, going out on your own, the pros and cons of being an owner vs an employee, therapy, entrepreneur pains, networking, knowing your numbers, and underdog stories.
After having a death grip on the highly contested screen taping record for the better part of the last decade as production manager at Shirt Kong, Kyle Caldwell (CEO of Garage Dog Brewing) has shifted gears and is now running the training and support program at MADE Lab. Topics of discussion include: The Press Assistant to Production Manager journey, gatekeeping information, what makes a good production manager, what an ideal schedule looks like, production bottlenecks, hiring, testing, and gimmick bands.
Caught up with Matt & Dave from Classy Screens after a late night of printing, and immediately got into Matt’s wild story of how his young California skater self came into printing these large last minute rush orders in New York City. Topics of discussion include: sketchy couriers, working with iconic skate brands like Globe and Baker, falling into printing through the New York art scene, live printing, Santa Claus gigs, a haunted print space, balancing inbound and outbound sales, judging a pizza by it’s logo, seeing your prints in the wild, expanding your offerings, 3I/ATLAS, and sharks.
Brett Bowden and Justin Lawrence are back on the pod to catch us up on the going ons of their respective shops, as well as spread the gospel of Print Hustlers Conference 2025. Prepare for a great conversation with some great dudes. Topics of discussion include: Fulfill engine, pivoting markets, company identity, taking care of your community, business events, bringing buttons back, art disruption, creating live events, equipment upgrades, Facebook groups, and Waterworld.
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