Terry started his real estate career in 1987 working on a part-time basis with Rose Realty-Better Homes And Gardens. He rapidly became the top sales and listing agent and opened, along with his partner, their own office in 1989, TW Shortt And Associates, REALTORS.

In 1992, they purchased two Better Homes and Gardens franchise licenses and launched a brokerage firm called TW Shortt and Associates-Better Homes and Gardens. The firm rapidly grew to fifty agents as well a separate property management division.

His professional real estate career has included leadership roles in virtually every position within the local REALTOR association, culminating as Association President in 1996 of the Heart Of Kentucky Association OF REALTORS.