Michael Chasen was happy running the education-software company Blackboard as a start-up, as a venture-capital darling, as a successful public company, and as a private company (again). He waxes enthusiastic about every stage of CEO-hood, even the notoriously pressure-cooker life post-IPO. "People say it's a lot of extra everything—from paperwork to expense to hassle," says Chasen. "But I didn't find that to be the case."

Everything seems to have cut Blackboard's way, almost from the day Chasen co-founded it with Matthew Pittinsky, a colleague at KPMG Consulting. Having raised around $50 million by the time Blackboard hit the Inc. 500, Chasen swiftly raised another $50 million from investors who liked his at-the-time retro insistence on actual revenue. "We sailed through the blowup, because our business model was, Let's sell software and get clients to buy more," says Chasen. In 2004, he took the company public, with a valuation of $400 million.

"The company has reached $600 million in revenue, 5,000 employees, and 20,000 institutional customers."

Recently, Chasen spied on the horizon the rise of open-source educational software, a long-term development he wasn't sure the impatient public markets would wait out. So, last year, he orchestrated the sale of the company to Providence Equity Partners for $1.64 billion. That deal allowed Blackboard to acquire open-source companies in the United States and Australia, and gave it control of Edline, a provider of K-12 technology that Providence owned and Chasen wanted. "There are appropriate times to be public and appropriate times to be private," Chasen says. "In a private company, you can make moves that are a little more out of the box."

As Blackboard has reached $600 million in revenue, 5,000 employees, and more than 20,000 institutional customers, the board and executive team have occasionally discussed whether Chasen remains the best leader for the job. "We decided that with the track record I had, it made sense for me to continue," says Chasen. "And I think that decision has proved out."