Gregory's construction skills were developed early in life by his Jamaican immigrant father. Greg's dad's mottos were "I can fix it" and "Why hire someone when you can use your offspring as free laborers?" Greg worked as a stand-up comedian for many years doing remolding job on the side to support his stand-up career. Four years ago he bought a 120-year-old five-story brownstone in Manhattan. After realizing the general contractor he hired had a "little drug problem," he cut down on his stand-up road career, and devoted his time to restoring his home. In addition to his work on In a Fix he continues to work as a comedian in clubs all over New York, as well as cruise ships.