Rich, of Portsmouth, Rhode Island, says his father started the Settler program when he was in high school. Over the years, the family fleet included a C&C 33, a New York 36, and a Peterson 42, all called Settler. The boat's name is a nod to the family's heritage. "My dad always said our family was related to the original founders of the town of Southold on Long Island, one of the first English settlements in New York in 1640. So we thought the name was appropriate, particularly because settlers are typically the first ones there, so for a race boat, it makes sense."