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Rick Waszkiewicz began their career in 1996 as a Chef at the Neighborhood Club of Quincy, where they were responsible for managing up to five functions daily as well as preparing weekly menu specials and ice carvings. In 2001, they moved on to become a Line Cook at Top of the Hub Restaurant. In 2003, they were promoted to Executive Chef at Geoffreys in Boston. In 2004, they joined Randolph Engineering, Inc. (Randolph Eyewear) where they held various roles including Director of Inventory Control & Quality / Military & OEM Sales & Operations, Director of Sales Operations // Quality, Customer Services and Returns Manager, and Senior Manager of International Sales. In their last role, they were the Sales Manager of the Commercial Market Division, where they were responsible for establishing programs and processes to sustain fast and scale-able growth.

Rick Waszkiewicz is currently enrolled at UMass Boston, pursuing a degree in Business Administration and Management, General. Rick previously obtained an Associates Degree from Johnson & Wales University-Providence in Culinary Arts/Chef Training, which they completed in 2001.