A graduate of the California Culinary Academy, Olmstead spent the initial years of his professional career working in restaurant kitchens in Honolulu and San Francisco. In 1998, he accepted a position at the InterContinental Mark Hopkins Hotel, where he was promoted from second cook to executive sous chef to executive chef, a position he held for four years before begin appointed director of food and beverage. In that new position, which he held for three years, Olmstead was responsible for the day-to-day operations of the property's food and beverage operations, which included two restaurants, room service, and catering. During his tenure at the InterContinental Mark Hopkins, he served on a special task force as director of food and beverage for the opening of the InterContinental Los Angeles Century City, a 10-day project renowned as the quickest conversion in InterContinental history, earning him a place on the brand's 2007 "Team of the Century." In 2007, he accepted the position of director of food and beverage for the InterContinental San Francisco and regional director of food and beverage for InterContinental Hotels Group. This promotion involved leading all food service operations for the brand new 550-room property, as well as assisting with other directors of food and beverage at the brand's Holiday Inn and Crowne Plaza properties in the West and Southwest, and coordinating the corporate World Class Beverage program. In 2009, Olmstead moved across the country to serve as executive assistant manager at the InterContinental New York Barclay, a position he held for three years before taking on his new venture at the InterContinental Chicago.