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.