Upon leaving Marine Corps active duty in 1987, Sargeant joined Delta Air Lines as a line pilot, however soon left Delta to take the helm at Sargeant Marine Inc. a small shipping company his father, Harry Sargeant Sr., himself a retired Naval Officer, had founded in 1983.
In 1992 Sargeant began acquiring asphalt tankers in earnest, and within four years he had grown the young company to a fleet of six asphalt tankers, one ocean tug, three ocean barges and several hundred bulk containers.