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.