As the president and founder of JWS Enterprises, Jerrold “Jerry” Shipman has been involved in real estate deals across Cape Cod, Massachusetts, and Westchester, New York. Through the firm, Jerrold Shipman also purchased Manhattan's Eastside Billiards and Bar, which was initially established in 1990.

Before founding the company, he was involved with the Armed Forces Benefit Association, where he was a territory manager. In the position for three years, he was responsible for operations across Nevada and Southern California. Jerry Shipman regularly gave presentations to service members on military bases.

He received several accolades during this time, such as being named in the top five of the company’s sales force. In 2003, he was rewarded with a trip to Aruba for his performance. He is involved in charitable efforts outside of work, and is a passionate defender of the environment. An avid animal lover, Jerrold Shipman has rescued several dogs.

He has also been involved in community efforts, such as coaching basketball and hockey, among other sports.