Around his Intercollegiate sailing schedule for St. Mary's, Scott occasionally attended a Windsurfing competition but remained a sailor first through his college years.

Upon graduating college, Windsurfing (commonly referred to as Boardsailing at the time) was simultaneously named as a new Olympic sport.

In the Fall of 1981, Scott attended the Windglider World's in Palamos, Spain and finished 4th out of over 100 competitors marking the beginning of an Olympic campaign as a US Boardsailing team member under Coach Major Hall.

It was a hurdle that Scott cleared but was pushed extremely hard by his US challengers (held at the eventual Olympic competition site in Long Beach, CA).

Afterwards, Scott worked closely in a variety of ways with Mistral Windsurfing, did advertising campaign's for Chanel and others as well as becoming a consultant coach for upcoming Olympic aspirants.

The 1992 US Trials (Ft. Pierce, FL) proved to be a highly competitive event that Mike Gebhardt would eventually win.

In Annapolis, he lived on the Naval Academy grounds in the Captain quarters from age 2-10 prior to his father retiring from the Navy after 26 years of service.