Gregory worked his way up from a scaffold boy, to a labourer on production and drilling crews, to eventually becoming a producer of oil dipping equipment. Since many wells in Lambton County did not produce enough crude to place three pole derricks or jerker lines on the well, Gregory invented a machine that could be lowered into the well and pull accumulated crude out of the well and to the surface – this machine was called an oil dipper. He built his own dipping machines and earned $1.00 to $1.50 each day dipping oil out of wells. Even on this moderate wage, Gregory could afford to build himself a house on the 12^th Line of Enniskillen.