I sort of believe this literally. He's always lived a life of luxury, so I gather he has little if any idea how most of America lives. But ever since he pivoted his business to simply selling his name and playing the role of a successful businessman on a reality TV show, I really don't think he considers any other form of reality. He lives in a world that is presented to him on the television, and he presents himself either on television or in detached, impersonal forums such as rallies.
We already discussed how his style and taste is more or less stuck in the 1980s, and his grasp of American business and culture—if it can be said to exist at all—reflects what was generally true in the 1980s. Since he lies as habitually as he breathes, it's hard to know what he actually knows or believes.