Eric Gustafson, 51 (“Going on 20,” he says), is the owner of Fun Seekers, a summer and winter instructional outfit that merges his passions for surfing and boarding. In the winter, Gus splits 120 days on snow between guiding day tours in the Wasatch with Utah Mountain Adventures and instructing snowkiting. In the summer, he heads to Wellfleet, Massachusetts—on the wrist of Cape Cod’s geographic arm—where he and a staff of seven instruct windsurfing, kiteboarding, surfing and stand-up paddle boarding. Gus says that splitting his seasons between snow and water allows him to keep things fresh: “At the end of each season, I get the itch to move on.”

Gus atop Days Fork. [Photo] Tyler Cohen