Harry is a miserable mess right now. With no place to go and no real friends who would allow him to stay over for a few days, Harry had to stay in a homeless shelter.
Surrounded by people who are down on their luck, poor, and have no prospect for the future, Harry realizes that he might get stuck here forever, just like these people.
He starts regretting his choices. He looks back at the past few months and begins to realize just how messed up he had been.
Now, as he hits rock bottom, he starts realizing how much of a bum he has been. Spending months doing nothing and living off Jenny's money, and using that money to fund something that never existed.
He also regrets ever being friends with Tom. He thought the money he was giving to Tom was being used for their start-up company, but he now realizes that Tom was just using him.
Stealing his money while showing him dreams about an unachievable future.
