While on the subway heading back to Brooklyn - I had gone to see Iron Man at Union Square, it was great - I was thinking about Microsoft. I was trying to imagine what exactly Microsoft could do that 1) doesn’t have an entrenched player, and 2) they might be able to be successful at. Search the Google way, in my opinion, does not satisfy either requirement, even if they bought Yahoo. So what else?

I considered Tim O’Reilly’s suggestion of investing in pieces of an “Internet Operating System”, which could be the answer although they’d have to fight Amazon, Google, Cisco and others for the bragging rights. Requirement (1) no, (2) yes.

I considered gaming, hardware, healthcare, social networking, and others…. but Microsoft is always involved there with mixed success. Is there anything left?

I’ve got a crazy suggestion. And yes, your own personal blog is the perfect place for crazy suggestions. So here it is - Microsoft should work to be the #1 destination site for vertical searching of the “organic web” (I just made that phrase up). The organic web would be defined as information that is continually changing. One example is airline ticket prices. Another is real estate, and another is classifieds. Microsoft should go out and develop / acquire any company who currently has the following properties: (1) The relevant data changes continuously, (2) The site is a leading player in their vertical, and (3) search is the main user activity on the site. Examples I can think of are Farecast (they bought this one), Craigslist (good luck there), and Redfin. With insider access to the data, Microsoft could provide superior search experiences to Google. Microsoft could then create a search portal that would be the first place everyone would go to search for data in these areas. Google’s crawlers can only go so fast - if Microsoft could provide a “real-time” search engine customized to a particular vertical, they could differentiate themselves in a very powerful way.

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