It is very hard to compare 'risky' (you said that already); I know a fair bit of people who risked their health because of their startup; strokes & heartattacks because of not sleeping and continues, years long high levels of stress. When I see people in a wheelchair at 26, sleeping on the street doesn't sound too bad.

Also I am curious; I read often about the US (I presume you are from there, apologies if not) that people say what you say 'have to live on the streets if it didn't work out'; don't you have friends and family? Friends and/or family would take us in or provide a house until we get out of the hole; don't you have people like that? I read a lot in the news (but news is not very accurate these days) that for instance 60% of Americans couldn't get $1000 in an emergency; I wonder if this is some group where everyone is completely broke or if it's just sensational press.