What's interesting about the way he's written these, is that getting rejected became his goal. He started hoping for rejection. Which seems totally backwards

What's interesting about the way he's written these, is that getting rejected became his goal. He started hoping for rejection. Which seems totally backwards until you realize that he wins in every interaction - either he gets rejected, or he gets what he asked for. And I'm assuming that's the whole point of this exercise. Once you can re-frame rejection, it disarms the sting entirely.