5. Business.com, $7.5 Million
Buyer: Jake Winebaum and Sky Daton
Eight years before R.H. Donnelley purchased the entire company outright for $345 million to compete with SuperPages and YellowPages, Business.com was owned by two friends who purchased the domain name to create a B2B site. Many laughed at the purchase, especially after the Internet bubble popped, but the two got the last laugh when they sold for 46 times what they originally paid.