As a 10 year old he hitchhiked 10 miles to caddy at the Petoskey Bay View Golf Club, a hundred year old club on the shores of Northern Lake Michigan. After graduating from college, with a business degree he turned professional and became a Golf Director at one of Michigan's finest resorts. He then played professionally during the Southern winter months.

While travelling to play on the Australian-New Zealand Tour, the South -American Tour and events in the South and West of the United States, Stewart would look for old golf items of interest in his spare time. These items were displayed in his golf shop at the Adios Golf Club in South Florida where he was head professional for ten years. His extensive and growing golf library led to his publication of his first best selling book, "A Tribute to Golf."

During this stretch of his life he was invited to become a part of the founding of the first golf facility in the USSR. While there, he met his wife Ilana, a native of Russia, who was flying for Pan Am at the time. After the birth of their son Bryan, the Stewarts moved to Pinehurst, North Carolina, “The Home of American Golf” where they set up shop in the historical Harvard Hotel Building with all of the items he had collected over a 30-year career in golf.