David Calvert was born in Detroit, Michigan in 1951. He grew up in St. Petersburg, Florida where he began as a sailmaker at Morgan Racing Sails in 1972. In 1976, he moved to Islamorada, Florida where he started Freedom Sails, Inc. Freedom Sails became Calvert Sails in 1986.

During the 1980's and early 1990's, David raced windsurfing competitions and won numerous championships, including two national and one world title. For the last 12 years, he has won 10 national titles in multi-hull,tri-maran sails racing classes, all with sails of his design. Today, Calvert Sails is one of the top multi-hull sail lofts in the United States with numerous wins in every region on the United States and Caribbean.

Dave became crew of the 125 ft. mega catamaran, PlayStation. During 2001 and 2002, he was onboard as a driver and helped to set five world records including both Trans Atlantic records and the 24 hour speed record.