Entrepreneurship, Paul Revere Style

After graduating from Duke in 1993, he got a job writing news for CNN in Atlanta. But, he said, he "wanted to get in front of things." He left Atlanta after a year and headed for Chile.

He talked his way into a job at Chile's largest television network. He also talked his way into riding on a Chilean battleship. (I am not making this up.) When he got off the ship, he pitched the idea of a coffeehouse to leaders across Santiago -- and raised $40,000 ($5,000 from his parents, one of whom is journalist/pundit/presidential adviser David Gergen). He converted a Victorian mansion into an 80-seat restaurant and art gallery.

That was around 1994-95.

The coffeehouse eventually was cash-positive, but after his partners took their shares, it was sold in 1997 at a small loss.

He learned an important lesson from the investment: Have ironclad legal documents that detail who owns how much. He also learned he was a good salesman.

"It's what I am best at. Getting people excited about new ideas," he said.

Gergen his friend Burck Smith when they were interviewing with the Department of Education, and they began batting around business ideas.

"We started tossing stuff back and forth and really decided there was one idea that lent itself to the Internet: How do you provide real-time, high-quality academic support to university students 24 hours a day, seven days a week?"

In other words, online tutoring.

They spent six months putting a business plan together. Gergen said he knew they had to have a rock-solid business plan before they could make their pitch to investors.

It also helped to have connections.

They raised $100,000 from their families and friends and $900,000 from investors, including the father of Gergen's best friend at Duke, who had made a fortune in cable television.