Thanks everyone for the comments! This piece came from an experience I had in college one summer. I made friends with a couple of guys that held signs on the corner by my work, after stopping to get them a meal one day, named Jimmy and John. They were really awesome people and I would regularly stop on my way home and sit on the curb in my shirt and tie, and have a coke or a sandwich with them.
A day I'll never forget came when I had to go back to college and knew they were going to be moving on. Someone had mistakenly given them a bag full of backpacks instead of clothes earlier that day, so John gave me new backpack, which I still use to this day 14 years later. The thing that stuck with me the most was how happy these guys were to be able to give me something as a gift.