Chris Sharpless first followed in his father’s footsteps by joining the family mushroom business before becoming a manager of a live music venue, where he met his wife. The couple then moved to Barbados, where Sharpless becoming involved in the hospitality sector in the Caribbean. Whilst living in the parish of St. Thomas in the mid-1970s the couple opened the first McDonald’s restaurant on the island. From there he went on to open the first multi-complex condo hotel company in the territory, with it soon becoming the largest hotel company in the area. Sharpless served as the President of both the Caribbean Hotel and Tourism Association, and the USVI Hotel Association. As a keen sportsman he also developed a national championship SCCA GT2 race car team, and represented the United States Virgin Islands in the two-man bobsleigh at the 1988 Calgary Olympics.