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Broadcast.com - $5.7 billion

In 1999, Broadcast.com was acquired by Yahoo for $5.7 billion in stock. That's why, Cuban said, "if you have the technology working in your favour, if you're the path of least resistance and if you have consumption, then you just have to go for it. Those are the pieces that create a moat that are really hard to replicate."

Jet.com - $3.3 billion

Walmart bought jet.com for $3.3 billion. Walmart isn't filled with silly, desperate or impulsive leaders. They are a company forever in transition and forever looking for new ways to grow. What Walmart did was buy a cachet and steal it. It paid $3.3 billion in cash (and made Jet's founders very, very happy). Here's the thing, the Walmart label comes with some ... baggage. It has its benefit too. But the world that Amazon.com operates in, the Walmart marquee doesn't have the same pull.

Cars.com - $2.5 billion

Cars.com was valued at $872 million (we get that number from reading the SEC filing, courtesy of the parent company, Gannett Co., Inc.).

Business.com - $345 Million

The $7.5 million spent on purchasing business.com in 1999 lands it on the list of the largest domain name sales in history. But at the time, no one could have imagined that this domain would be worth 47 times more in a period of just 8 years.

LasVegas.com - $90 Million

This domain was purchased in 2005 by VEGAS.com, LLC which wanted to pair up the two domains to ensure that both search terms directed online traffic to the travel agency from Las Vegas. The massive $90 million sale ensures that this will always be remembered as one of the most expensive website purchases.

CarInsurance.com - $49.7 Million

QuinStreet, a vertical marketing and online media company from California, made headlines at the end of the last decade with some of the most expensive domain name purchases ever. In the period of just 13 months the company had acquired three huge domain names in the world of insurance, culminating in the purchase of CarInsurance.com on November 8, 2010.

Insurance.com - $35.6 Million

QuinStreet's other purchases hold third and fourth spot on the list of top domain name sales. The second in the trinity of insurance domain names that QuinStreet bought was acquired for $35.6 million in August 2010, along with all the media and the technology assets that Insurance.com already possessed. Similar to CarInsurance.com, this online platform was regarded as valuable because it was a popular destination for comparing insurance rates on cars, health, life, home and renters insurance.

VacationRentals.com - $35 Million

Tourism has never been as popular as it is in the modern age of the internet, with countless ways to promote, explore and find the best possible deals to satisfy your travelling needs. Perhaps not surprisingly, one of the all-time top five most expensive domain names for sale had to do with vacation rentals.

PrivateJet.com - $30.1 Million

This is the only domain on the list that is geared almost completely towards the richest of the rich, offering luxury jet charter rentals for global business flights. It seems only fitting then that its purchase in 2012 is considered the highest pure sale of a domain name in history!

Voice.com - $30 Million

Voice.com is the most recent domain name sale on the list following what seemed like almost half a decade without earth-shattering acquisitions. It was sold to Block.one, easily topping the list of the most expensive domain names in 2019. What makes it even more of a special entry is the fact that the creator of EOS cryptocurrency bought the domain through a cash transaction facilitated by GoDaddy.

Internet.com - $18 Million

We already mentioned how QuinStreet went on a buying frenzy in 2009 with their purchases of the largest insurance-based domains that are firmly in the top five of all time. But that's not the whole story. The company also bought one of the best domain names, Internet.com, for $18 million in cash. A number of other top domain names were part of the deal, including InternetNews.com, ServerWatch.com, Webopedia.com, Developer.com and others.

360.com - $17 Million

This is the only number-based URL on our domain name value list and one of the rare domains of its kind that managed to bring in the big bucks. The sale was made in 2015, when Zhou Hongyi, CEO of Qihoo, decided to create a new brand that would unify and encompass all of his products and services. The bold move cost $17 million.

Insure.com - $16 Million

Who better to end with than QuinStreet - the company that dominates our domain price list with 4 out of 10 top sales of all time in a span of just 13 months. Insure.com was their first purchase of 2009. The sale drove up future domain values after the damaging first year of the Great Recession.

Tesla.com - $11 Million

In 2018, Elon Musk, co-founder and CEO of Tesla, revealed the purchase price of the domain name Tesla.com, which the company had acquired two years prior. He paid $11 million to buy the domain from its previous owner. Tesla had been using the domain TeslaMotors.com before the purchase of Tesla.com.

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