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From the Wall Street Journal:

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, 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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His hair, good looks and penchant for Italian suits helped him stand out in the New York’s Silicon Alley from the late 1990s until he left in 2005. He appeared frequently on television as a technology pundit, most famously on the Oprah Winfrey Show when he taught the talk-show host how to use the Internet in 2000. That same year, People magazine named him the “Sexiest Internet Executive.” Mr. Wasow’s business acumen and ability to translate complex ideas to a general audience earned him quasi-celebrity status and an annual six-figure income.

So it surprised many in the technology world when he decided to resign his leadership position at Community Connect Inc., BlackPlanet’s parent company (which was later sold for $38 million in 2008), and move to Cambridge, Mass., to pursue a Ph.D. in African-American studies and government at Harvard University.

His transformation began on the drive to the airport after delivering a speech at a technology conference. “I realized that just giving speeches wasn’t enough,” Mr. Wasow says. “I wanted to write prose, not just PowerPoint. I wanted to be held accountable for my ideas, not just applauded. I wanted to develop a level of mastery over some body of knowledge rather than just be a mile-wide and an inch-deep.”

Until his mid-30s, Mr. Wasow, whose father, uncle and grandfather were all professors, had rebelled against the idea of teaching and instead aimed to be a socially conscious entrepreneur.

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