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Many homeless people are like this. They choose to live this way because they don't have to deal with the responsibilities of life.
I can not believe that people decide to live that way, but you can be right though.

Perhaps the rewards coming of development were not as quick as doing a dirty job for X hours to get Y dollars?

In my city, we have tons of homeless shelters and help for anyone that needs it. Yet, many choose not to live in these shelters and live on the streets because they don't want to follow the rules of the shelters...which aren't really that strict.
People don't decide to remain homeless based on a rational cost/benefit analysis. It seems to be more of a case of such people being trapped within their psychological limits. This is what happened to Leo, the homeless man in question. From the article:

"When Business Insider caught up with Leo months after the successful launch of his self-made and self-coded app, Leo was still homeless. It seemed he didn't want access to the money that was available to him, which was being held in McConlogue's account. It was too overwhelming."

Maybe being homeless isn't something you just bounce back from when there's money. Poverty is violence.
And this opinion comes from? Personal experience? Research? Are you a social worker or anthropologist?
I'm sorry, but I'm going to have to down vote you. Since personal opinions that people don't agree with seem to be down voted, I'm going to jump on the bandwagon.
How did I disagree? I was asking for more information and assuming the best.
If you genuinely believe that, you are among the most stupid, callous people on the Internet, which is saying something.
Poverty is crippling, not just in the lack of money, but in the severe amount of time that it takes just to get the basics of food, shelter, and safety. Reminds me of Mazlow's pyramid. There's no time for coding if you're hustling all day to get a bed or a meal. And there's even less time to leapfrog from coding to business.
Completely agree. When you are completely down is more difficult to keep the wheel moving than when it has some inertia.
You can't eat fame or pay rent with fame.
You're right. they should figure it out and change the plan dsasdasfasfafahhhhhhhhhrrhagasdjadkbadbsaksbdkabsdkjabsdkajbsdkajbdsjkabsdkabjsdkjbasdjadjaksdbkajsdbkajsdbkjabsdkjabsdkjbasdkbasjd