This rather confused me. Even more so because some of the details seem to being live edited. A cycle courier for legal documents that gets to read the documents. He crewed on a sub (initially im sure it said commanded) yet doesn't get on with computers yet even though he is homeless he knows about the square product, and also having never worked in design knows about Dieter Rams, someone with almost no designers I've…
The most successful homeless guys that were reasonably cognizant had a story. (Interesting note: the few female homeless people I encountered all had apparent mental problems.) Sometimes it was a story about their amazing life that took a turn for the worse through no fault of their own, sometimes it was about some tragedy that had recently befallen them or a family member, sometimes it was an "emergency" they needed help with, sometimes it was just a quick tale to build rapport...
This sounds a bit harsh but they are all con men. That's how you survive on the streets. I would not be surprised if literally every tale that I heard was completely fabricated.
That's not to say they are all liars or you shouldn't help the homeless, but the smart ones adapt to their situation quite well.