When Chris Jester and his wife returned to the U.S. after traveling around the world for a year, the duo knew it was time to embark on a new adventure: entrepreneurship. SailTime, a franchise that allows customers to share boat ownership, proved to be the perfect entrepreneurial vehicle for Jester. Ten years later, his business has allowed him to save up enough money to repeat the trip – this time with two kids in tow. Here’s what he’s learned over the last decade.