Date sold: October 2013

A man named Rick Schwartz registered eBet.com in 1996 for $100. He held on to it for nearly 20 years — making a juicy profit off of it when the domain company Network Solutions bought it for $1.35 million.

Because Schwartz has made a number of high-profile sales — you'll run into another much later in this list — he's earned the nickname "Domain King."

"When do I sell? When the domain name is ripe," he writes on his blog. "When is it ripe? When the right buyer comes along."