Ryan Seacrest was a pudgy preadolescent who dreaded summer because it meant he'd have to take his shirt off at the local pool in the affluent Atlanta suburb where he grew up. He had to wear orthodontic headgear, which he struggled daily to thread into the hardware on his teeth. The kids on the junior-high football team teased him about his weight ("in a ‘Hey, you want the last Little Debbie?' kind of way"). But the huskiness didn't become untenable until he developed a crush on a blond girl at his school.

"I had no courage to ask her out," Seacrest says, sitting in his sunny, modest office at E! headquarters—the only notable feature being a framed photograph of Seacrest and Dick Clark looking eerily similar—an up-since-dawn pallor obscured by makeup from the taping of an earlier news segment. "So I started throwing away my lunch—I had been eating two sandwiches. For three months, I would only eat an orange or a grapefruit, depending on the day."

Put aside for a moment that he was a chunky kid trying to get his classmates to like him—what's telling about this vignette is the methodical approach he used to obtain his objective. The blond girl ultimately did surrender, but by then, having harnessed the power of persistence, Seacrest had moved on.

Yet he has been living according to the grapefruit principle ever since. When Seacrest was 16 and working nights as an intern at STAR 94-FM in Atlanta, becoming a successful radio personality—and ultimately the head of a towering multimedia empire—became the new blond classmate.

"I remember thinking, Everything I do from this point on is a step," Seacrest says. "If I'm scrubbing the break room, I'm closer to the studio room. And if I'm in the studio room, I'm closer to the microphone. If I'm closer to the microphone . . . I really got the psychology of it—that everything is connected."

Back in his office he holds up a piece of paper covered with a grid—completely filled—representing tiny increments of his time. "It scares me, too, sometimes," Seacrest says, considering the planned-to-the-second day before him.

But it is in the service of continuing to build Seacrest, Inc., that he keeps this schedule. If he sticks to it, he can work in more meetings in the future. Meetings with blue-chip entertainment-industry advertisers: Proctor & Gamble. Coca-Cola. Wal-Mart.

"As a presenter or a talent, there's a saturation point," Seacrest says. "As a content provider, it's very different. . . . I want the advertisers on Madison Avenue. If they buy into it, then hopefully the mainstream audience buys into it."

"He's not trying to be cool," says his friend Charlie Walk, the president of Epic Records at Sony. "He's just completely focused on continuing to create an entity that covers all areas of pop culture."