I don't think it's being an asshole; the flip side of getting used to hearing 'no' is getting used to saying 'no'. People like the security guard he asked for $

I don't think it's being an asshole; the flip side of getting used to hearing 'no' is getting used to saying 'no'. People like the security guard he asked for $100 are probably pretty used to it. Maybe not so much the guy whose house he played soccer at, but he had a 'home field' advantage, in that he was safely in his house. In general it seems like he approached people when they were in a comfortable place, so he was at a disadvantage. As someone who worked retail for a number of years, unless the store was packed with people I wouldn't have flat-out refused him a weird request, I probably just would've escalated it. Touring warehouses is unlikely, though, because of health and safety restrictions. But the doughnuts one is perfectly reasonable even without asking a manager. You probably ask people for things every day that make them uncomfortable. Getting used to that sort of repulsed reaction is probably harder than dealing with the actual 'no', so I think it's an important part of the project.