Carter Glatt, a sixteen-year-old junior at the Horace Mann School, is lanky, with black hair and long eyelashes. He loves to play sports, especially football and tennis. He speaks in a slightly stiff, respectful manner that suggests that he’s used to conversing with adults. He carries a BlackBerry with a crack down the front. Last summer, he started a business, but he wouldn’t be able to run it if his mother didn’t drive him around.

Glatt’s family owns a weekend house in Southampton (his father is a hedge-fund manager), and one recent Saturday he was sprawled in the back seat of his mother’s Mercedes S.U.V., narrating a tour of the neighborhood for a visitor. “Is Bernie Madoff’s house on there?” he asked himself. “Yup, I think it’s 216 Montauk Highway.” A copy of the Hampton Star Map—Glatt’s creation, which he sells for seven dollars and ninety-five cents—was spread out in front of him.

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