I would hope, though, that your friend isn't quite so in denial about how significant the massive boost that starting capital gave him was, and doesn't describe it as "small", or hold it in contempt. I'm fairly sure that my parents have between them only just passed the $1 million (at present rates, and after tax) for their combined lifetimes (most of which has, of course, disappeared).
Whatever you make of it (and, as I have tried to make clear, it isn't the gift itself I object to but Trump's description of it), it seems difficult to associate someone with that much money to start with as in touch with the difficulties of the common man whom he apparently appeals to so. "I am your voice," says Trump. Really?!