From the ground up: The Story Behind the Company

Growing up in a small town, Dean Gregory Jr. didn’t have much. Raised by a father who worked in residential construction, working his life away to provide for his family, he spent his childhood surrounded by the right values, a hard work ethic,—and dirt. “the words -I believe in you even when you don’t believe in yourself- will always ring through my ears”. Though his father did alright for himself, he never had anything handed to him. “That made me the person I am today”.

“What I blame my father for…” was the gift of a strong back, a pair of calloused hands, and a drive to build something better—not just for himself, but for everyone around him.

At 16, Dean Jr. started his landscaping company. With a $5,000 first car, a walk behind mower, and a cheap tractor-supply trailer, he spent every day after school, weekends, & nights working to grow his business to help support his future dreams. By 17, Dean was taking care of over 40 Lawn clients per week while in high school. “It afforded me my first truck, a nicer trailer, and better equipment.” He learned the value of hard work, how to mix concrete by eye, how to build/maintain landscapes, and how to stack blocks until the walls stood straight.

By 18, Dean was utilizing compact construction equipment to take on bigger projects. “I remember jumping into a machine and I thought to myself, man I could do this for a living!”. That year, Dean applied to be an Operator & got into the International Union Of Operating Engineers - IUOE LOCAL 478. Years were spent learning the trade of heavy highway construction, working underneath large contractors throughout Connecticut. Dean gained experience in all aspects of heavy civil construction including site plan reading/development and spent years operating heavy equipment. These jobs included building parking lots, bridge construction, ponds, footings, foundations, trenches, pipework, sub-grading, fine grading, electrical conduit installation, earthmoving, mass excavation, utility installation, solar fields, environmental, site contaminant remediation, retaining walls, drainage, landscape structure construction, water management, landscape design, general site remediation, vegetation removal, and leveling & compaction.

There was no trust fund—just trust earned, project by project. From patching driveways to building multi-tiered retaining walls, he built a reputation for showing up early, finishing strong, and doing things right the first time. He listened more than he talked, soaking up every bit of knowledge the older guys passed on along the way.

Today, Gregory Construction stands as proof that your background doesn’t define you—your work ethic does. What started with a shovel in the dirt lot has grown into a company known for craftsmanship, integrity, and resilience. The mission is still the same: build solid, honest work that lasts.