I'm not sure I'd regard making 100's of thousands of dollars complete failure. Now, it's obvious that he made money in ways that aren't overly useful to society, and promoted products that were less than stellar in spammy ways, but just having the goal of "Making Money Online" I'd consider that money to be pretty dang successful. The fact that he blew it all after the fact just makes him bad with money. It doesn't me…
The purpose of commerce is to help us create value for one another. But there is a bunch of activity that uses the same tools that is essentially parasitic. The reason his income streams kept blowing up was that people eventually decided that they were better off without him involved.
He could have spent 10 years building products that were creating value. He could have spent 10 years learning the tools and techniques necessary to make the sorts of thing where customers can't get enough. Instead, he spent a decade as a leech on the ankle of the economy, getting scratched off and reattaching himself.
I could have gone the same way. In high school I had a job doing telephone fundraising. It turned out to be basically a scam, with ~12% of the money collected even going to the non-profit, and therefore even less being spent on actual beneficial work. There was a lot that was appealing in the work: smart, funny people; great challenges; getting paid in cash. But eventually I came to realize how morally bankrupt it was. I got lucky in that it was much easier to see how what I was doing was worthless.
So now he's basically starting over. And good for him, I say. I think this post is incredibly brave, and I wish him the best of luck in making something so useful that customers are clamoring to hand over their money.