Is the takeaway here, "Be prepared to be responsible for the negative externalities your business creates"?
I'd say it more like "get to know some folks at city hall because fairness is going to be seen about as often as a Kadupul flower blooming."
But Uber and AirBnB are giant companies that actively flaunt city policies. I imagine OP's friend probably doesn't have an army of lawyers and probably wasn't aware he was violating any.