Honolulu Realty

“First-time buyers are my favorite. I love showing them how to do deals. Invariably they call me back in a couple years.”

Having graduated from a top prep school in Hawaii, Benn has a strong circle of contacts for his upper-end listings and investment properties. His first commercial transaction, a Japanese-owned golf course, came through a prep-school contact. About one-third of his volume now is commercial but if several hotel projects work out, that could zoom to 90 percent.

Target marketer: He uses his knowledge of the Taxpayer Relief Act of 1997 to teach homeowners the benefits of tax-free capital gains on the sale of their home. “We have a lot of military personnel in my area,” he says. “The savvy ones buy homes with their housing allowance.” When they ship out—as long as they’ve been in the home two years—they can make some money.

Thinking big: Benn’s experience with the golf course listing gave him a new plan—to get into real estate development within the decade. He’s also putting together investment groups to pick up foreclosures, which are increasing, he says. “Maybe I’ll be the Donald Trump of Hawaii!”