Ryan Seare, 47, was the first of his neighborhood friends to invest in a Hawaii vacation home.
He convinced four other families to join him at a property in Kauai where shares start at $445,000.
For his precedent-setting investment, Seare chose Timbers Kauai, an intimate community of 47 homes tucked away on Kauai's southeast shore near a lighthouse, a marina, and a Costco.
Between the Seare, Phillips, and Smith families, there are 13 kids ranging in age from 2 to 17.
"Sometimes when you're on vacation, you don't want to see people you know, because that's part of vacationing.