I think this is rewriting history just a bit.

My recollection is that, when Uber first entered the marketplace in various locations, it was largely a gray area as to whether their business was legal.

Since then regulations have changed, been clarified, or been litigated in courts to clarify their legal meaning... and Uber then proceeded to ignore those laws and do whatever the hell they wanted to.

But my view is that that culture, of simply ignoring laws it saw as inconvenient, came a bit later, after they started to become successful and viewed themselves as essentially above the law.