I was in a similar situation to his when I was younger, OP, with ruined credit, stupid irresponsible debt, bone idle far too much/often, skint, no direction at all...
Now I'm a successful professional with a happy family, perfect credit, zero debt (actual positive equity!), stable relationship, great job I'm good at and enjoy, house nearly paid off, admirable insurance...
It took me many years of hard work and really focusing, but I got to where I am on my own.
At least for ME, I needed that failure, that shitty part of my life that I'd dug myself into. I learned from my mistakes, and even though I didn't know where I was trying to go most of the time, I had a lifestyle to run from and a few tangible goals to work toward.
Maybe the "bootstraps" method isn't what's best for the way your DB learns, but it's not a bad life experience, at least. It's character building!
I do wish him luck. It's hard to drag yourself out a hole when you can't see the top and may not even know you're in it.