I have made similar mistakes in my life path as he has (I am a white guy you know), but where folks like himself pound the financial pavement and chest, I took the time to get therapy, and work through the toxic culture of masculinity far before it hit the mainstream as it is now (circa 2015).
I am glad I did so because I have become a better husband, and better friend to the people I spend time and energy on.
You are absolutely right it is sad and pathetic. Folks seem to forget the time and energy you spend around people and interacting with them is like water on a stone.
What most people don't get is you want challenging waters and clean waters, not the acidic waters that articles and folks like himself pro-port IRL.
There are so many ways I could help him navigate his personal issues since I have fought and won those battles he is fighting, but at the end of the day the ROI from him ... not worth it.