I didn't get how that would work but I'm curious as to whether it would.
If he's legit, he might just be hoping that a good outline might convince some prospective clients that the writer knows what he's doing, because students often have a lot of trouble even with the outline stage. For a more experienced writer, a typical undergrad essay can be outlined in a few minutes, which might make that a worthwhile investment if gets him a few new clients, especially if he's starting out in this business and doesn't yet have a client base.