Jay opened The Bird Machine print shop in his apartment complex's basement in 1999. Before that, he worked at Screwball Press and learned the ins and outs of screenprinting from Steve Walters. Initially, after starting his own business, Mr. Ryan's original customers were merely his band, the bands of friends, and venues where the groups performed. As the business grew larger, it eventually took up residency at a commercial space in the Chicago neighborhood of Ravenswood. Now, The Bird Machine Print Shop has a permanent home in Skokie, Illinois. Jay is well-known for his computer-free design and hand-drawn text processes.