Jay graduated from Temple University with a degree in art. He also studied at the Barnes Foundation in Merion, Pennsylvania, then taught in the art department there. He appeared in the documentary film The Art of the Steal, which examines the figures and forces behind the relocation, disfigurement, and commercialization of the art collection at the Barnes Foundation.
Raymond is editor of Pressing News, a publication of the Pressing Iron and Trivet Collectors of America. His first book, Streamlined Irons, was published in 2008.
His work life has also encompassed the jobs of heating mechanic and contractor, building inspector, handyman, and maître d’ of a vegan restaurant. He and his partner, Catherine Suttle, live in Frenchtown, New Jersey.