Owner, Sam Gilbertson, started working for himself as a freshman in high school in 2006. He started with a custom made ice cream bike selling novelty ice cream treats around his neighborhood. This continued for two years until a vacation to New York City gave him the idea to purchase a New York Style hot dog cart for the City of Sheboygan. After purchasing a used cart in 2008, he established Sammy G's LLC, allowing him to hire an empolyee to operate the ice cream bike. He operated the first year as a business with two kinds of hot dogs, Regular and the Classic American Hot Dog. During that time, Jeremy Jochman, devoted customer and friend of the owner, developed the Reuban Dog- a hot dog with melted swiss cheese, thousand island dressing, and sauerkraut. During the second year of business, the Kraut Dog, Reuban Dog, and Chili-Cheese Dog were added to the menu. The Reuban Dog became an instant hit. Currently, Sam operates his hot dog cart five times a week and special events and manages one employee.