Matthew Entringer didn't grow up around homelessness. Then one bitter December in 2021, three or four people were bundled up in the lobby of his downtown Kansas City apartment just trying to stay out of the cold, and he couldn't unsee it. He started carrying care kits in his backpack, fell in with a Saturday outreach at Scraps KC, and by 2023 he'd filed the 501c3 paperwork for Street Support KC. The conversation starts there and ends up on dopamine, shame, and how a small business can use AI without losing the human part.