Josh Abramson and Ricky Van Veen

Previous Lives:
College students

Big Break:
Created a website to trade jokes while attending different colleges

Bottom line:
The site now boasts more than 8 million unique visitors a month
 
In 1999, these two Baltimore area high school friends created a goofy Web site to stay in touch when they went to separate colleges. They started out posting funny pictures of themselves doing gags and stunts, what Abramson has called "stupid college stuff." 

Soon, they began forwarding links to their friends, who then passed them along to other students. Before long, college kids were sending Collegehumor.com their own photos and videos, attracting first thousands of visitors to the site every week -- then tens of thousands, then hundreds of thousands. By 2005, the site was getting up to 8 million unique visitors every month and generating millions in ad and merchandise sales.   
 
By that point, Abramson, Van Veen, and two other 20-something friends had moved to New York and were sharing a 4,200-square-foot loft in Manhattan. More recently, Abramson, now 26, bought his own $1.975 million condo.  

At a recent business conference in New York, Van Veen conceded that much of the site's success came from simply being in the right place at the right time. "When we started in 1999, we were one of the only games in town," he told organizers. They've since been forced to adapt to ramped up competition, he added.