> why would I risk my money, time and hard work on someone with a recorded record of making poor choices when there are hoards of others who haven't broken the law?
This assumes that your scrappy bootcamp grad hasn't broken the law. In fact the more likely scenario is that they have broken the law multiple times, they just were never caught and charged for it. Unless we are suddenly going to believe that young adults and teenagers don't have an affinity for recreational marijuana or underage drinking or doing any of the various stupid things young people do.
Your mentality applies to yourself as well: why would any investor or employee risk their money, time, and hard work on someone with no proven track record, when they could throw it at the hoards of other CEOs who have demonstrated the ability to profit? You wouldn't want someone to look over you just because you never got the chance to demonstrate your potential; it would be equally unfair to look over someone else who served their time and is now looking for opportunities to demonstrate themselves.
> (yes, once you commit a felony, even after serving time you are still a felon)
Then what is the point of imprisoning felons? Why don't we just kill them all? If there is no way to recover from being a felon, why let them live or let them out?
Sounds harsh, of course. The answer should be that once you have gone to prison and gotten out, your crime is behind you, and unless you are actively committing crimes again you should be judged equally with someone with no record.