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Kai Ryssdal: Microsoft is betting big on its new search engine — Bing it’s called. The company’s $100 million advertising campaign debuts tonight. It is their latest and most expensive attempt to unseat Google as the king of search. And if they succeed even modestly, Microsoft might have one of its other big rivals to thank for the inspiration. Marketplace’s Sam Eaton reports now on what the software giant has learned from being “uncool.”

SAM EATON: Ever since Google became synonymous with search the company has been untouchable. Now Microsoft hopes to change that with a new product called Bing and a splashy ad campaign that casts Google as cumbersome and dated.

BING AD: We don’t need queries and keywords if they bring back questions and confusion. From this moment on search overload is officially over.

Technology analyst Rob Enderle says Microsoft is attempting to do to Google what Apple so successfully did to Microsoft with its “I’m a Mac, I’m a PC” campaign. Portray it as inferior.

ROB ENDERLE: Microsoft has to first make people dissatisfied with Google search before they can get them to move and the first phase of this advertising campaign is to a large extent designed to do that.

The question is whether that’ll be enough to make people switch. Microsoft’s last redesign, “Live Search” flopped. Enderle says Bing could be different. That’s because it produces more detailed and useful information than Google in the initial search.

ENDERLE: Bing does seem to provide the promise, or at least fulfill the promise that it makes, even in this early phase and the end result is, coupled with good marketing, they may in fact actually take an impressive amount of share.

That is, until Google fires back with an upgrade and multimillion dollar marketing campaign of its own.

In Los Angeles, I’m Sam Eaton for Marketplace.