Better to offer a fair price from the start, IMO. That isn't $5, nor is it $100.
Take your publicity and stuff it, buddy! We already got enough of that! Now we need to feed our kids! :-) Our game was long and now we'll play it shorter, thank you!
This is true regardless of whether your main career goals are running a business, working for funded startups, or just getting a stable job at BigCo, by the way.
Writing a book is playing the long game. Pricing is simply strategy. To me, it just looks like he's choosing his strategy for how to play the long game, but either way it's the same thing.