Wow, OUCH! I do feel sorry for the guy, at least a little. I'm sure he thought he had it figured all out. Was making money for himself, and his investors. Then BOOM his life is forever changed, and will never be the same. Fuuuuuu.
Yeah that was the feeling that I got too. He genuinely thought he had a "safe" investment method that generates a steady income for his investors and it was working out. He wasn't conning people money or defrauding people or anything. And naked option premium does seem to be investors the best of both worlds at times, both "safe" and profitable until it's not. And when it's not, if you are not hedged and/or you did not cut loss early, then you are royally screwed which is what happened.
I used to do naked shorts as well. I am glad I stopped long time ago after I suffered some losses and realized that it's not as "safe" as I thought it was. Judging the abundance of promotional material about the safety and profitability of option selling, this guy is not the only who is losing his clients' money and won't be the last.