Raised in the world-renowned wine-growing region of the Red Mountain AVA in Washington State, Gregory was exposed to wine at a young age. It was not until the age of nineteen when he took that life experience to the next level and joined the wine cellar team at Bern's Steak House that he started to really develop his passion. Two weeks after turning twenty-one Gregory took and passed his introductory level sommelier test. Shortly thereafter he accepted a harvest internship position in Washington State at Kestrel Vintners; this three-month long internship helped to solidify his growing knowledge and passion in wine.
After four years enlisted in the Army, Gregory found himself living in Louisville, KY. Eager to get back into the hospitality industry, he took a job working as the event manager at 610 Magnolia. This gave him the opportunity to reacquaint himself with wine and he would work as sommelier in the restaurant. Just nine months after getting out of the Army, he took and passed the Certified Sommelier test through the Court of Master Sommeliers. Gregory was then offered a position working under Master Sommelier Scott Harper at the Bristol Bar and Grille in Jeffersonville, Indiana. Working as the bar manager, he had the chance to be mentored by one of only 211 Master Sommeliers in the world. While living in Louisville, Gregory received a degree in Beverage Management from Sullivan University. In addition to being a Certified Sommelier, Gregory is also a Certified Specialist of Wine and Certified Specialist of Spirits through the Society of Wine Educators.