What are the odds that such guy would be given a chance to share a piece of himself like he did ? I really don't think the OP was naive. I think there should be more people like him.

Y Combinator gave a chance to people who would never have a chance at seed investors or Angle investors. It appeared that YC found few very valuable gems though. Surprised ? You shouldn't because seed investors and Angel investors have strong bias to what a high potential candidate or project would look like.

I assume we have a similar strong bias regarding homeless, close to consider them as hopeless. Though I believe that there are gems in this group of people as well, that need only to be given a little push and help to shine out.

And as for Y Combinator, people would consider it all normal and obvious afterward if someone does it for them too.

My impression is that it was a kind of surprise for the OP to discover that he had a bias regarding such kind of homeless guy.

BTW a bike shop looks like a good long term investment considering the energy crisis. In Greece, a business that is very flourishing in this strong crisis period is selling wool ! In Italy they raised gasoline tax so that a litter cost 2€ (because of debt)! We'll all reach that point soon or later. Beside, real lean startup founders ride bikes !