Giving a homless man $100

September 30, 2026

This morning I awoke and walked to the bus stop. Arriving late, around 9:30. A man was sitting on the bench, and as I paced and spoke on the phone, I witnessed him move his bag from the bench seat to the ground. This small gesture told me that he realized that I did not have a place to sit, and his bag was taking up space.

I finished my conversation on the phone and spoke with him– at this point he was sloped over, looking at the ground, I brought up the ants, which seem to love this stop, and crawl between the concrete. He said that he thinks the ants are in the roots – we start to talk.

He is 37 years old, from Florida, and explained that he made a series of bad investments in his social circles, and has ended up on the street. He lived in Clearwater, sold vintage clothes, skated, and was even married. Now, he has no place to go, and is living his life.

As we spoke it was obvious he was intelligent, and interesting. He has a sense of humor in there, and he was honest and cohesive. The bus pulled up to the stop, and he boarded.

He didn’t pay his fare, and the driver began shouting at him, I told the driver I’d pay his fare, and the bus ride started. On the way to the back of the bus, I spotted the man, and I asked him to follow me. He did, and we sat at the back of the bus together.

I ask the man: “what do you need in order to get your life together? Do you want to work?” The man explained that he wanted to work, but is missing some of the fundamentals, he has no place to stay, wash his clothes, etc.

He said a hotel room for 2 weeks would be around $800. The man also had no phone.

I thought about this – and as he continued to talk, I listened. I happened to have the proceeds of a recent Craigslist deal, and decided to give it to the man. He reached into his pocket and pulled out a piece of cardboard that was folded – it read “anything helps”. He took down my phone number, email, and website.

He said he would text me when he gets a phone. I’ll update this if he does.

I wish him the best, and I hope he reads this