Trump has spent 50 years in a business where he MUST have rapport with working class people.
Who is going to tell him about looming issues with his properties before they become BIG problems? The people who see everything: the maids, the janitors, the workmen, the people working the front desks. It's from THESE people that he gets a feel for how things are going, before the issues become big enough to show up on the balance sheet.
Thus, he learned how to chat with workers, something that elite politicians don't generally do.
I’ll reiterate my earlier thought that was borne out by several trump employee speakers providing direct testimony
Trump had more experience hiring VP’s than all the rest of the candidates put together