The obvious big ones are Uber and Airbnb, but then we get into things like amazon and sales tax.
And then there are companies like Aero , who construct elaborate legal fictions (having a million different antennas does not change much if your service is functionally equivalent to any VOD service by cable companies).
A legal fiction is a legal story that doesn't actually match the literal facts.
There argument is a legal fiction in that it doesn't match the service actually being advertised and offered. The implementation doesn't matter, because the end result is rebroadcasting material to members of the public.
Sometimes regulations are there because of an experiment we already tried, and no amount of iPhone app magic will change human nature on certain points.
When the new company is small, everyone love it. Once it get big and more powerful, government will like to have more control over it and get/use/blackmail some of the power. It is power struggle.