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 ever met have ever heard of.
Just a weird story over all.
This should be no more surprising than running across a CEO that doesn't get on with computers (if he actually commanded), or an electrician or car mechanic that doesn't get on with computers (if he was an enlisted crew member).
There are lots of jobs on Navy ships that have absolutely nothing to do with computers, and some of the things you might assume are run by computers are controlled with very old (and coincidentally reliable and/or fixable with common tools) technology like switches, relays, reach rods, and magamps. (Or at least this was the case on many ships that were in use during the Gulf war.)
Quite cultured and knowledgeable people can go off the rails a bit.
It's like this came out of Chicken Soup for the Soul.
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.
Also, being homeless and jobless (I have no experience with the earlier, and I don't recommend it) is great to improve ones intellect, because, the person has no stake in anything, and can come to unbiased conclusions on subject matters. Also he/she can dive in and learn anything, just out of curiosity.