In my professional life I've noticed that often when I explain things once people don't understand what I'm saying, so I was forced to adjust my speaking style to explaining the same thing 4-5 times in different ways in the hope the people I'm speaking to would understand at least one of them. Of course to the person who understands what I'm trying to say the first time this seems redundant and repetitive, but it does help more people understand what I'm saying who otherwise wouldn't.

Perhaps ideally I would simply learn which of the 4-5 explanations was most effective and simply tailor my speech to that, but I'm not sure that's always possible or even a constant.

I've never listened to Eric July explain something so I don't know if that's what he's doing, but it is a possible good-faith explanation for him repeating himself.