There’s the Wai­alua that we think we know, the one where a rollicking Friday night starts with a round of headlight hide-and-seek and ends with beers on the hood watching the townies spin cluelessly around the Hale­iwa-Wai­alua rotary, the Wai­alua where ATMs number about as many as traffic lights and both can be counted on one hand.

Then there’s the Wai­alua — tough, humble plantation town — that turns out folks like 34-year-old entrepreneur Todd Naca­puy.

"There’s that small-town mentality here that makes you want more than what’s in front of you," says Naca­puy, whose father, a former plantation worker, now operates his own papaya farm.

Nacapuy originally wanted to be a doctor, but he discovered an interest and an aptitude for business while attending Seattle University. He was participating in a management program at Boeing when a friend called with a crazy proposition.

"He said, ‘Hey, I got $20 million in seed money. Want to come work with me?’ Naca­puy recalls. "I didn’t even know what that was, but I said, ‘Sure.’"

Cobweb, one of the first e-commerce businesses, would prove wildly successful, growing from a modest operation (Naca­puy was employee No. 4) to a powerful company with some 900 employees. Naca­puy and his partners rode the wave for six years before selling the company.

 Back at home, Naca­puy worked as a media consultant before landing a position with Microsoft.

"There are people who have been with the company for 15 years or more," he says. "They’re already millionaires several times over, so what motivates them is different. To work next to highly skilled, highly motivated people like that, and to be able to live in Hawaii, is a dream come true."

For Nacapuy, however, the realization of his own dreams obligates him to help others achieve their goals.

He’s partnered with restaurateur Hiro­shi Kimura to launch Royal Hawaiian Cookies, a gourmet shortbread cookie line, and is helping Kimura’s Yaki­niku Hiro­shi restaurant expand its base to local foodies. He’s also provided business-incubator support for the nonprofit North­shore.com, a community business site.

It’s a small-town thing, perhaps. For Naca­puy it makes perfect sense.

And so he volunteers as a coach with Egan Ino­uye’s boot camp physical training program because he believes in what Ino­uye preaches (losing 50 pounds didn’t hurt). And he cherishes the memory of caddying for local golfer Kristina Merkle, a longtime friend, when she teed off in her first LPGA event.

"You can’t reach the top without help, and being able to repay some of that by helping others is what really makes me happy," he says.

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Reach Michael Tsai at mtsai@staradvertiser.com.