[4] In 1955, Rudolph left Florida for New York City, and Rupp opened a private architectural practice at 224 South Orange Avenue, downtown Sarasota.
During the next several years, Rupp worked closely with his architectural peers in Sarasota; Ralph Twitchell, Jack West, Gene Leedy, Tim Seibert, Victor Lundy, and Bert Brosmith.
In 1959, Clarence Scott commissioned Rupp and Farrell to design a commercial building that would serve as a showroom for the Barkus Furniture Company.
Acknowledging this important architectural achievement, the building was restored, renamed McCulloch Pavilion, and added to the U.S. National Register of Historic Places in 2017.
[17][18][19] In 1962, Rupp was featured in a special edition of Life Magazine, in an article entitled, The Takeover Generation – The 100 Most Outstanding Young Men and Women in the United States.
[20] In 1965, Rupp moved his architectural practice to Naples, Florida, where he worked on several projects; including three apartment complexes, an animal clinic, a restaurant, and his own residence.