Then you generally couple regulatory arbitrage with money spent on lawyers and lobbying to monitor the existing loopholes, in order to make sure they don't disappear.
What Uber/Lyft are doing is more equivalent to poker: a combination of betting (a large enough war chest to pay lawyers and fines) and bluffing (using marketing campaigns to garner public interest and shame/scare the establishment).
When the stakes get too high (e.g. ride sharing laws in Austin, TX), they fold.
Not one of the the groups you mentioned makes a habit of breaking the law. They look for opportunities to get around the excessive weight of our insanely litigious and complicated regulatory environment.
There is absolutely nothing wrong with this. They are helping humanity escape the productivity sink of pointless regulations, set insanely far along the diminishing returns curve.
Think about how many billions of dollars of productive output are wasted every year so some idiot pencil-pushers can make sure the correct stickers are present on building materials.
This guy didn't want others to play by one set of rules while he played by another (advantageous) set.