While graduating from Fanshawe College with a diploma in Business Marketing, Jay was recruited by Disney World as an ambassador for Canada at The Epcot Centre. After a year in Florida, he returned to Ontario and got his real estate license in 1996.

After working for years with home builders, developers, and investors he co-founded Stronghold Real Estate Inc. in 2008. During his tenure at Stronghold Jay also founded an energy reduction company to help multi-residential landlords across Ontario reduce their hydro consumption. Ultimately over 60,000 apartment suites and their respective common areas were retrofitted with new lighting. This delivered massive rebates to their customers such as Drewlo Holdings, CLV Group, Skyline Apartment REIT, Ferguslea Properties, Terracorp Management, Boardwalk, Paramount Properties, and others. Jay decided to sell the company to a national company in 2014.