I have to admit that this advertisement by Microsoft, poking fun at Google and Gmail – with an advert for its Office 365 service – is pretty funny.

In it, they take shots at Google’s habit of scanning your email messages and extracting keywords and tokens in order to better target advertisements that cross your screen.  So, if I were to email people about the broker I use, say, TD Ameritrade, and talk about the run up in the Nasdaq we’ve had since the start of the year, then Gmail would serve me ads about investment seminars and trading products and maybe even advertisements for cheaper brokers.

On the one hand, I like targeted advertisements that are relevant to me.  There are certain things I care about:

  • Thai food
  • Magic books
  • Software that would make stock trading easier so I don’t have to write it all myself using tons of copy/pasting in Excel

But do I want Gmail reading my email, looking for keywords?  Do I care about targeted advertising that much?

Which do I value more?  Keeping my email private or having relevant products brought to me for my perusal?  Which do you value more?