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12 Good And Bad Deals That Have Cost Yahoo $10 Billion

Yahoo today is worth nearly $30 billion.

But over the 19 years since its founding, Yahoo has spent billions of dollars buying companies ranging from internet radio to technology that summarizes text. Just a small portion of these deals — the 12 listed below — adds up to more than $10 billion, or about a third of Yahoo’s market cap.

That’s not to say, however, that they account for $10 billion of value — or any value at all. In fact, many of the companies Yahoo acquired, including some of the priciest ones, don’t even exist today. An ominous point worth keeping in mind in light of its $1.1 billion deal for Tumblr.

Here are the price tags for a few of Yahoo’s biggest acquisitions, pulled from a collection of its SEC filings:

1. Starting from the top, Yahoo spent more than $5 billion on

Rob Kim / Getty Images

Led by now-owner of the Dallas Mavericks Mark Cuban, internet radio company sold to Yahoo at the height of the dotcom bubble in 1999. (Deal value based on Yahoo stock price at time of acquisition).

2. Yahoo bought a stake in Chinese e-commerce business Alibaba for $1 billion that has paid off nicely.

China Daily / Reuters

Yahoo sold a part of its stake back to Alibaba last year for $7.6 billion to fund some of its recent acquisition spree. The remaining portion has turned out to be a tantalizing prospect for Yahoo shareholders, estimated to be worth between $7.5 billion and $12 billion.

3. Yahoo bought Interclick, an advertising platform, for $259 million.

This was a pretty sizable acquisition that came at an odd time in the company’s life. Yahoo bought Interclick shortly after former Chief Executive Carol Bartz left the company, closing the deal in November 2011.

4. Yahoo acquired BlueLithium, an advertising network, for $255 million.

This was around the same time Yahoo bought Zimbra, one of the first acquisitions of the Jerry Yang’s tenure as Chief Executive of Yahoo.

5. Yahoo also picked up Geocities for about $3 billion…

Kevork Djansezian / Getty Images

Remember when Yahoo was vying for dominance of the portal empire? Geocities was a big part of that play. Unfortunately, portals have faded in popularity in favor of home feeds like Facebook. (Deal value based on Yahoo stock price at time of acquisition).

6. Yahoo also bought Right Media — another online ad exchange — for $524 million in 2007.

Yahoo has spent a lot of money on advertising services and networks.

7. In March, Yahoo spent $30 million on a 17-year-old’s startup that summarizes text.

Suzanne Plunkett / Reuters

Nick D’Aloisio, the 17-year-old founder of a startup that summarized large blocks of text into smaller, more digestible chunks, sold his company to Yahoo in a deal that left some industry observers perplexed. Yahoo implemented the technology into its news app.

8. Yahoo bought online video provider Maven Networks for $143 million.

Also part of the Jerry Yang-era acquisitions. It ended up shutting down in June 2009.

9. Yahoo paid $303 million for Zimbra, but it doesn’t own it any more.

Stefanie Keenan / Getty Images

Bought shortly after Terry Semel (on the right) resigned as CEO of Yahoo, the company turned around and sold it to VMWare in 2010.

10. Yahoo also bought MakToob, an online portal in the Middle East, for $164 million.

This actually still exists, as a variation of the Yahoo homepage.

11. Yahoo also spent about $432 million, on eGroups, which went on to become Yahoo Groups.

This also still exists today – though with the emergence of Facebook and other social networks it’s unclear if how widely this service is still used. (Deal value based on Yahoo stock price at time of acquisition).

12. On Monday, Yahoo spent $1.1 billion on Tumblr.

Frank Franklin II / AP

Yahoo bought David Karp’s light-blogging service for more than $1 billion. New Chief Executive Marissa Mayer, the company’s 7th CEO since its founding, insists Yahoo will be pretty hands off during day-to-day operations.

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