Boom: The 15 Biggest Internet Buyouts In History

Twitter, Groupon, Zynga, Facebook: It seems each day brings a new valuation in the tens of billions of dollars for the next big Internet startup. 10 years after dot-com robber barons like Mark Cuban made a killing off of code, the richest, most powerful people in the world are once again rocking t-shirts, flip-flops, and bed-hair.

With venture capitalists habitually flocking to a rash of new hotbeds of online innovation (SXSWi, Y-Combinator, Disrupt, etc.) with bags of cash at the ready, have we found ourselves in a new Internet bubble? Time will tell. Just yesterday Instagram, one of the most popular new social networks, was acquired by Facebook for $1 billion. The purchase raised the eyebrows of tech insiders and casual users alike. But really, that was nothing. Hot Internet properties have sold for way more. Follow us in a countdown of the Internet's biggest paydays to see how we got here—and what today's Big Thing might look like tomorrow.

Sale Price: $1 billion
Year: 2010

You probably wouldn't know ATG, or Art Technology Group, by name, but more than likely you've seen their work: the eCommerce software firm built the online stores of giants like BestBuy and Tommy Hilfiger. In 2010, the veteran systems giant Oracle handed over $1 billion in order to bring ATG and its customers into the fold.

Sale Price: $1.1 billion
Year:1999

Synonymous with driving directions at the turn of the millennium, AOL put down a pretty penny to own MapQuest in 1999. Too bad they couldn't see Google Maps just around the corner.

Sale Price: $1.2 billion
Year: 2008

Microsoft scooped up FAST, a Norwegian-based company known for its specialized search products, in order to bolster its SharePoint software and the still-gestating Bing. In 2009, it was discovered by Norwegian police that FAST had conducted shady accounting tactics in 2006 and 2007 and CEO John Lervik resigned from Microsoft in disgrace.

Sale Price: $1.2 billion
Year: 2009

Zappos.com made its name offering an old product (discount shoes) to an new market (online shoppers). By 2009, it was the largest online shoe retailer in the world, and had expanded to offer all kinds of clothing and accessories. That year, Amazon announced that it had acquired its younger competitor for $1.2 billion in an all-stock deal.

Sale Price: $1.5 billion
Year: 2002

One of the first great web applications of the new decade, auction giant eBay snapped up PayPal at a premium because of its secure and user-friendly online payment system. Early employees of PayPal would later go on to work on a number of promising new startups, including YouTube and Facebook.

Sale Price: $1.63 billion
Year: 2003

In 2003, Yahoo! shelled out $1.63 billion for Overture Services inc., owners of third-string search engines AltaVista and AllTheWeb. The bid was to help Yahoo! Search in its doomed fight with Google. By 2009, it was Yahoo! that was being consolidated, as it was announced that Microsoft's Bing would be running its search operations.

Sale Price: $1.65 billion
Year: 2006

Google turned heads in 2006 by making a year-old user-generated video hosting site its largest acquisition to-date. Detractors questioned whether YouTube, already facing legal battles from both movie and music studios, was worth the cash. Google doesn't release YouTube's finances, but today the birthplace of a million memes is the third most popular site on the Internet, after Facebook and Google itself.

Sale Price: $2.6 billion
Year: 2005

eBay was ahead of the game when it acquired Skype in 2005 for a surprising $2.6 billion. By 2009, the VoIP and video calling service was making appearances on Oprah and Who Wants to be a Millionaire. That same year, eBay sold a majority stake in the company to a an investment consortium at a profit. In 2011, Skype was sold again to Microsoft for a whopping $8.5 billion.

Sale Price: $3.1 billion
Year: 2008

Google can afford to do nearly everything it does because of one business model: advertising. The company's AdWords and AdSense products bring in the vast majority of its revenues. In 2008, the Googleplex ponied up $3.1 billion to further its dominance of the online ad realm with the acquisition of DoubleClick—an ad-serving firm with a powerful client list. The price was reportedly driven upward by a bidding war with Microsoft.

Sale Price: $3.2 billion
Year:2007

Specializing in online collaboration software for the enterprise market, WebEx received a juicy buyout from Cisco Systems in 2007. At a whopping $3.2 billion, the sale represented a bit of re-focusing for Cisco, known primarily for its offline products.

Sale Price: $3.6 billion
Year: 1999

A GIF-laden online community that emulated real-world neighborhoods, GeoCities was the third most visited website in the world in 1999, averaging 19 million unique visitors per month. When Yahoo! came knocking, the Los Angeles-based company collected a $3.6 billion pay check. But GeoCities' limited functionality and high server costs meant that it bled users and cash as time passed and "Web 2.0" began to flourish. By the end of 2009, Yahoo shut down the service in America completely.

Sale Price: $4.2 billion
Year: 1998

In the '90s, AOL was perceived in a way not unlike Google is today: synonymous with the Internet itself. The dial-up provider and internet services giant made a massive bid to acquire the alternative browser Netscape in order to liberate itself from the tyranny of Microsoft's Internet Explorer. Netscape was never able to detract significantly from IE's market share, however, and as the browser field became more crowded, the once iconic application was shuttered. A number of Netscape engineers went on to create Mozilla Firefox.

Sale Price: $5.7 billion
Year: 2001

In the biggest payday of the first internet bubble, Broadcast.com's sale to Yahoo for $5.7 billion helped make Dallas entrepreneur and co-founder Mark Cuban a household name. Unfortunately for Yahoo!, Broadcast's primary function of aggregating internet radio broadcasts didn't enable any of the competitive advantages or sustainable business models that had been projected on to it. Today, you'd be hard-pressed to find any traces of the website's existence.

Sale Price: $6 billion
Year: 2007

Making a bid to play in the lucrative sandbox of Internet ad servicing, Microsoft payed more than it ever had for a company in order to acquire the digital marketing network aQuantive in 2007. With a $6 billion price tag, the move remains the priciest of its kind. aQuantive and all of its services were later re-branded and incorporated as a part of "Microsoft Advertising."

Sale Price: $10.3 billion
Year: 2004

In a near hostile takeover that took a year and a half to pull off, the venerable systems tycoons at Oracle wrested control of the immensely popular web-based human resources software outfit, PeopleSoft. All told, the endeavor cost a cool $10.3 billion. Larry Ellison, Oracle's resident yacht aficionado and CEO, likely didn't lose too much sleep over it, though: the hefty sum is just a little more than a third of his own personal net worth.