A list of the most expensive web domains ever sold

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Early in the days of .com, individuals smart enough to realize the internet would be big business jump on the opportunity to buy domain names at a cheap price. Their target — URLs for some of the biggest companies in the world.

There were more than a few tales in the early days of the world wide web of small time hustlers holding .coms ransom. Big businesses paid big bucks to own a URL with their own company name wedged between those backslashes and dots.

Companies are still shelling out huge amounts of money to own desirable .com addresses. Here is a brief list of some of the most expensive .com purchases of all time.

Sex.com for $13 million

The story of Sex.com is about as shady as the people interested in making money off the website. The URL was purchased by Gary Kremen, the founder of dating website Match.com, in 1994. The website was part of a lengthy legal battle.

Here’s the story:

“Later in 1995, Network Solutions transferred the domain to Stephen M. Cohen, who had been trying to gain control of the domain for some time by misrepresentation, using phone calls, e-mails and forged letters. He eventually persuaded an employee of Network Solutions to change the ownership details by submitting a fake fax. After gaining control of the domain, Cohen produced an advertising-heavy site that received up to 25 million hits a day. From payments for click-throughs and other advertising, Cohen was reportedly making $50,000 to $500,000 per month. Kremen undertook steps to recover the domain, while Cohen claimed he obtained the domain legally from Online Classifieds (OCI). A five-year legal battle ensued.”

Kremen finally took back control of the domain name and won the court case to the tune of $65 million dollars. The website has since bounced around owners and was finally sold to Clover Holdings LTD for $13 million.

FB.com for $8.5 million

Originally owned by the American Farm Bureau Federation, FB.com was a sought after URL after Facebook introduced its retooled messaging system. Zuckerberg and company gave the American Farm Bureau Federation $8.5 million for the .com.

Fund.com for $9.9 million

The first dot com on the list that isn’t active, Fund.com was purchased in 2008 for almost $10 million. It’s sat dormant ever since. At one point, the website assisted users with financial information on investment fund options and gave expert opinion on building portfolios. It has since become a parked website.

PrivateJet.com for $30 million

Nations Luxury Transportation acquired the domain in 2012 from a leading intellectual property holding company for $30.18 million in cash and stock.

VacationRentals.com for $35 million

Here’s an example of businesses spend money just to spite a competitor. Purchased by a company called HomeAway, the company primarily bought VacationRentals.com to keep it away from a competitor, Expedia. The game of “keep away” cost $35 million.

Business.com for $350 million (kind of)

Originally a business search engine and web directory purchased in 1999, Business.com was purchased by Jake Winebaum, a previous chairman of the Walt Disney Internet Group, and Sky Dayton, the founder of Earthlink for $7.5 million. In 2007, Winebaum and Dayton sold the entire business, which included Business.com, to RH Donnelly for $350 million. Donnelly is the publisher of the Yellow Pages. The actual cost of the website URL is unknown.