Great story though. And kudos to dropping a c-note on him. Giving a lot to them rarely is far better than $2 here and there, which will likely just go to beer or a small meal. $100 they can actually do something important with.
In terms of how much money I gave him, I decided that $100 was probably the minimum amount that could actually help him pursue the idea and as a college intern, I'm not sure I could have spared much more!
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 !
Do you really believe this? I think most, if not all, YC founders are capable of raising a seed round and making connections in the Valley with or without YC. YC just expedites this process.
I didn't mean he was naive for what he did or for wanting the guy to succeed, even thinking he could. I simply thought he was naive to believe all of the stories the guy told about his great past.
Lots of homeless people tell fantasy stories about what they once were. A huge % of it is BS, though often based in enough reality to be believable.
The bulk of the homeless population is there in large part due to mental health issues. He can very well be genuine but completely off his rocker simultaneously.
I beleive it was the late, great, Greg Giraldo who said that beer and drugs are exactly what I would spend my money on so who am I to judge.