Although trying to make money with gambling is a stupid idea (and we have to make sure all young people know this fact in the first place), I wouldn't call it the riskiest enterprise. When you gamble online you can lose your balance, while when trying to rob a bank you can lose your freedom or even your very life. Also, there are a lot of shady businesses in the streets which are much more dangerous than gambling. Since adolescents are tend to do something risky anyway, maybe gambling is not that bad of an option.
Well some adolescents will see things like this : Gambling = loose your money = suicide or evolving in risky and shady business to get your money back.
Thus said, even in regular job you can loose all what you have in case of robbery without having an insurance... So yeah, it is complicated