(FORTUNE Small Business) – I'll be wearing a bow tie," Chris Whittle had said as we were making plans to meet for a drink. That struck me as a tad disingenuous. With his trademark neckwear, floppy Hugh Grant haircut, and glamorous accessories--rich, beautiful Italian wife, apartment in Manhattan's legendary Dakota building, former Yale president as business partner--Whittle has been in the public eye for nearly two decades. He had to know I'd pick him out of the crowd at the Four Seasons in Boston.

Celebrity, of course, cuts both ways. It was part of the magic while Whittle and his college buddy, Phillip Moffitt, were rescuing Esquire in the early '80s. And it was integral to the launch of the sequel, Whittle Communications, which attracted huge investments from Philips Electronics and Time Inc. (now part of AOL Time Warner, FSB's parent). By the mid-'90s, however, Whittle's media empire was in a shambles. He was pilloried famously in a New Yorker profile headlined "Grand Illusion." "I basically ran my media company right into the wall," Whittle says between sips of his screwdriver. "I had to glue myself back together.'' And sell the Dakota apartment.

Lost during the breakup was Channel One, now owned by Primedia. Channel One was controversial--free televisions and VCRs for any high school willing to make students watch a daily satellite news show with commercials. The educational establishment went ballistic. But what few people realize is that Channel One always was, and still is, fabulously profitable. (It was also ahead of its time--a pre-Internet version of the eyeballs-for-advertising-spiced-with-free-stuff business plan, except that Whittle made it work.)

Whittle survived the early '90s with just one asset intact: Edison Schools, his wildly ambitious scheme to reform public education in America by privatizing it. "The most important idea I've ever had," he says. "I view everything else as training camp." Whittle's Edison decade has been a struggle, marked by "near-death experiences," repeated holy-war-style confrontations with angry unions and school boards, and an on-again, off-again relationship with Edison's irreplaceable chairman, former Yale president Benno Schmidt. ("We've been together nine years, longer than the Beatles," Whittle says. "It's fine now.") Today Edison educates 57,000 students in 113 schools, ranks as the 60th largest (of 15,000) school system in the U.S., and can brag about rising test scores. But it has yet to turn a profit, and the stock, on this day in mid-March, is 40% off its high. "It has been"--he pauses--"a long, hard decade, but one I wouldn't trade in."

Really? Even when all around him people with no more skill, imagination, or ability to raise capital were building stupefying fortunes on the Internet? "There is nothing about this that is fast," Whittle says. "It's an important idea, it needs to happen, and it will not happen without a 20- or 30-year commitment. I mean, there are days I think about retiring. But not days I go, 'I wish I were doing something else.' "