[michaelchisari]

I wonder if, even if Libya were a stable country with no reason to cause worry, if it would still be a bad idea to invest $10 million into such a simple product.

Unless there's a long term plan, I don't see where the monetization of this service can come from. I always thought after the last dot-com bust, we'd be sensitive and conservative in respect to questions of profitability and revenue, but this investment in bit.ly gave me a bit of a sense of deja-vu, and it wasn't a good feeling.

[michaelbuckbee]

I think a common misconception is thinking that bit.ly is in the business of shortening URLs when in reality they're in the analytics business of tracking when, where and how often people use and share links.

As to monetization, they already have a $1000/month enterprise level plan that gives you tons of analytics and that runs lots of the custom branded URL shorteners (4sq.com, yhoo.it, pep.si, cs.pn).

If I were a bit.ly investor my number one concern would be Google linking up their goog.gl shortener with Google Analytics. Doing so would punch a huge hole in Bitly's value proposition.