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(WSJ) — Omar Wasow knew that the transition from Internet executive to graduate student at the age of 35 would be a dramatic one, and so in a symbolic break from his old life, he lopped off the two feet of dreadlocks he had been growing since he was a teenager.

That was 2005, when Mr. Wasow was the executive director of BlackPlanet.com, a social networking site that he founded seven years earlier and turned into the most popular African-American Web site at the time. Previously, he had developed Web sites for the New Yorker and Consumer Reports magazines.

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