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Just of the top of my head I could say Paypal (when they started out) and AirBnb operate in legal grey areas.

AirBnB operates in a grey area? That's certainly putting it nicely. How dark can grey be before it is black? :)

Paypal still isnt a licensed money transmitter in Indiana. https://www.paypal-media.com/state_licenses.cfm

And, Indiana also requires licensure for money transmission. IC 28-8-4-20 (a) A person may not engage in the business of money transmission without a license required by this chapter.

Therefore, Paypal is illegal in Indiana. But the only reason why I think they haven't been 'busted' is because nobody has complained yet to the appropriate Indiana authorities.

edit: I've been heavily criticised by OstiaAntica for this comment for being "anti-hacker". But I'm simply stating facts, and an opinion as why I think why. http://news.ycombinator.com/item?id=3088836

More likely, Indiana doesn't have any legal jurisdiction over Paypal. Just because something is a law in one place doesn't mean it's a law in another place, even if you have customers that are covered by the law.

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