Derek Sivers is definitely better off than most of us, but what he's describing is something any engaged parent could do. That's not a "silver spoon". Hell, my family was lower-middle-income (into solid middle-income with both parents working, then down again, these things can cycle) and they would quiz us on things like that. Though not with Anki. It's just good parental engagement.
I'm not taking a side, but I don't think that's a fair comparison. My family was lower income than this. My parents were at work so that we could have shelter, food, and not go into crippling medical debt for even basic care. There wasn't time for this kind of interaction.