In my experience, business ppl are the ones who like to break the rules more than others. I would argue most people here are employed engineers, and they mostly love following rules.

Yes but they ask lawyers how exactly they can break the rules and not get caught

I disagree, a key social purpose of complex legal rules is regulatory capture that allows powerful people to stay powerful. Smart powerful people don’t have to break the rules, they follow them in practice but not in spirit, whereas people without access to lawyers and legal sophistication break rules unknowingly, even when following them in spirit.

I'm talking in the practical kind of way: speeding, parking where you're not supposed to, "better to ask forgiveness than permission" kind of things, creative bookkeeping (I'm from Belgium :D), ... .

No idea what kind of high profile business owners you know, but in my circle in Belgium, most are small business owners. In my experience, employees like to follow rules, business owners like to push their boundaries.

I do know some high powered industry leaders in the USA. At that level you don’t break the rules, you make them… specifically to exclude you competitors while leaving carefully crafted loopholes for yourself.

I agree that what you are talking about applies to scrappy startup types, the same people that eventually stop breaking the rules once they have enough power not to need to.

Yes why should people fear authority? It’s not like there is a history of corruption and brutality in the police department or five policemen beating a man to death in Memphis within the last week.

I feel like the undertone of hacker news has always been hacking in ways that are productive (and therefore possibly applicable to making money). Woz does interesting stuff and this is such an example, but it's not really "productive"