Yesterday I reviewed the three best Internet acquisitions of last year. Today, an easier list to compile: the worst Internet acquisitions of 2007. Some of these acquisitions were too expensive, some were not a good strategic fit, and some were just plain dumb.

eBay acquires StumbleUpon for $45M. This is a case of two great companies that just aren’t matched well. StumbleUpon allows users to discover new web sites based on their interests - a very simple, well executed idea. StumbleUpon has an active, loyal user base and, as many sites have found, it can generate a ton of referral traffic. But what is eBay going to do with this? EBay’s statement of the time suggested they would use StumbleUpon to expose eBay’s users to new, random auctions they might be interested in. Yeah, and everyone will use Skype to call an auction seller to complete a transaction. Not gonna happen.

American Greetings buys WebShots for $45M. CNET bought WebShots awhile ago, couldn’t make it work, and wisely sold it to American Greetings. Flickr is far and away the leader in photo sharing and WebShots is a distant second or third. The problem with photo sharing sites is they are notoriously hard to monetize. If CNET with their huge online ad sales force couldn’t monetize WebShots, American Greetings stands no chance. This is just good money chasing after bad.

Cisco acquires Five Across for an undisclosed sum. Five Across is the parent company of the popular, but third-tier social networking site Tribe.net. Cisco supposedly acquired Five Across so that their corporate clients can build their own social networks. I don’t see it happening. At least Cisco didn’t pay much for this.

Disclosure: I own CNET stock, had a company bought by CNET, and have worked at the company as an executive.  I neglected to post this disclosure when I first wrote this article and should have done so.

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