This assumes that I was talking about straight up criminal behavior, which I wasn't.
I was talking more about pushing the law into the gray area. Should Uber be allowed to operate in NYC when taxis are regulated? Should AirBNB be allowed to compete with hotels? I think the founders of these services knew they could run into problems, but they chose to take the risk anyways. I think this is more of a risk oriented mind-set. People who aren't willing to take on risk may not even dare to get close to the edges.
It's only after the financial crisis that people were wondering if we should be locking a bunch of people up who were partly responsible for the mess. Did anyone go to jail? I don't know, but the list of people who did is probably pretty short. Obviously the people involved were pushing their rules as far as they could go.
Apparently even the government will do this. The NSA obviously pushed their given rules as far as they could, possibly into illegal territory, but still gray enough that it isn't obvious that we should be locking people up.
And laws change because a situation may not be obviously illegal. One day your actions may be illegal. Another day they may be fine. Again, separating those two lines is a bit of gray area. Perhaps successful people are there partly because they are more willing to push. Some may call this unfair and cheating. But that person may still walk if the issue was brought to court.
The world isn't fair. Sometimes it's the strongest and most ruthless people who win. The U.S. ended WW2 with a nuke and still has a lot of power through a superior military. Sometimes the U.S. will play by the rules, sometimes not.
I think people who are highly successful may tend to see that the rules aren't always solid. Sometimes they may be more like the edge of a rising and falling tide. Less successful people may see the rules as like prison walls. Not only do you not try to test them, you don't even get close to them.