Biologically, risk taking when things are going well is a bad characteristic. Risk taking when things are going badly is probably a good characteristic. So I think you over value risk taking without any other considerations.
Or at least, without breaking the law any more than anyone else does: http://www.volokh.com/posts/1248668478.shtml
(I don't find Kozinski and Tseytlin's original in a brief search, though it should be out there. Very much worth reading, and helpful to consider that federal law isn't the only possible risk.)
That is in fact what happens in poor and minority districts everywhere. It can happen elsewhere, and does and has in despotic regimes and times.
Tons of tech businesses are built on the back of open disregard for intellectual property and tech access laws. It just takes the wrong combination of events to get hauled in for that. Look at Aaron Swartz, whose conviction proceeded purely based on Carmen Ortiz's desire to get a cybercrime prosecution on her resume.
The truth is that a good deal of the work that HN users are likely to get involved in could be considered criminal because of unfair laws like the CFAA, DMCA, and the Copyright Act, all of which prescribe criminal penalties.
There are other laws that stalk startups and businessmen, ranging from tax law to esoteric industry regulations. If a businessman makes the wrong person mad, he could easily end up locked in jail. Martin Shkreli is another good example of this -- a few days after he made the news and pissed everyone off, the SEC filed an indictment. They did that because it's easy to accuse anyone who's done anything slightly out of the ordinary of crimes. This really has almost nothing to do with the person's moral fortitude or the harm they've caused in the world, except insofar as you believe that people in authority are unwilling to target innocent people (true pretty often, but not often enough).
Funny you put it that way... I made this account to tell about the time I tried to protect my girlfriend from the mental health system. The hospital wouldn't let her go, so I went to the superior court and got a hearing. The commissioner looked into the matter and ruled that my girlfriend's detention by the hospital was not legal, and ordered the hospital to let her go.
I should have called the police to accompany me to retrieve my girlfriend from the hospital's illegal custody. I got attacked by one of the security guards, who I'd later learn knew exactly what to say to the responding police officer because he was a retired cop himself. I got arrested, and my girlfriend was sent to be professionally misdiagnosed and mistreated by the system.
That was last September. I'm going back to the courts next week to ask for another hearing. I have looked at the laws regarding compulsory mental health, and have found several that are not being complied with or respected.
But... Someone I respect told me soon after I was arrested that... "missionaries get eaten by cannibals." The system perpetuates itself.
I basically follow the law, on par with other folks that follow the law. I've never had a ticket even, though I've gotten pulled over. In the states, I worked in a pharmacy. They do background checks per federal regulation. Etc. I've generally found it would be bad to get in trouble for stuff, even when I disagree with the laws and/or punishments.
I also have blue hair (the color changes from time to time). That means that unless I'm established in an area, I'm a target. I'm in my late 30's and get followed around for theft in stores and have been most my life. Even if I'm dressed professionally. I've stopped in McDonalds where cops have stopped and gotten followed out of town. Some employers would have fired me for my hair or never given me a chance. I'm likely to get searched at airports (and have, once for bombs because of artists pastels). Luckily I'm living in a different country now, and though there is a bias, it doesn't hold me back nearly as much there.
What boring white folks really means is: People that look and act like the average white folks for the area, and are into the average things (or at least what can be observed). People that fit in place and aren't on the fringes.