I really didn't know much about him before 2016. The only point I remember him before that was seeing him on TV in high school. My liberal self back then thought he was the ideal of a successful businessman, mostly because of his gold-plated billionaire aesthetic. Many at the time thought the same and I'm sure that's what convinced some substantial portion of the electorate to choose him in 2016.

In pop culture at the time, my image of him from 2010-2015 was shaped by a show on TV Land called How'd You Get So Rich?. The premise of the show was the host Joan Rivers would interview some rich person, where they'd give some bullshit story on how they got all their money. I don't remember the Trump episode clearly but, that and the ambient background influence The Apprentice had at the time were the pop culture references that put Trump in my head as some rich person archetype.

Edit: Also, remembering that Joan Rivers show has got the theme song stuck in my head again. It's amazing what sounds I fixate on and carry with me for the rest of my life.