1.) Uber was praised as role model and people tried to mimic them. That has impact on behavior or other companies and founders in tech community. Crooks being praised and rewarded means more crooks in the future.
People who think this is bad thing, wants (and have absolute right) to put attention on previously praised crooks so that opposite message (it is bad behavior and you might get punished) gets attention too.
2.) If you brag about your success and break-the-rules-strategy, people like you less and get more angry with you. Once you get caught, they get happy, talk about it and wants to see you punished more then as if you did not bragged. That is how humans work.
I agree, that rewarded bad behavior could lead others to follow. But, we have much bigger issues going on, such as the banking industry and all the mess that it has caused all the while getting rewarded for it.
Bragging isn't the problem, if what they're doing is illegal, then it should be handled accordingly. They might be thinking that they are thinking out of the box, and you might have to break some laws, but those laws are actually blocking progress. So, not necessarily a bad thing depending on the law being broken.
How does bragging make a difference? A crime is a crime regardless of bragging or not.
I think your second paragraph makes a lot more sense.