A yacht packed with vacationing millionaires off the coast of St. Bart's is an unlikely laboratory for social-policy reform. So perhaps it was the Caribbean sea breeze or the free-flowing 1945 Mouton-Rothschild that got Michael Saylor, the 35-year-old CEO of the high-tech company MicroStrategy, thinking about how to amend the inequities in higher education. He shared his thoughts over sea bass and chocolate souffle. "And by the end of the evening," he recalls, "I knew I'd hit on the next big thing in education."
Back ashore last week, Saylor took his idea public, pledging $100 million to create a nonprofit "online...