Not sure if he'd thought it through that far, but it seems like a pretty good and calculated risk that's paying off. The fact that he is as open as he is (though hopefully he knows better than to report numbers that appear worse to the IRS), I think makes his customers want him to succeed that much more.

Broadly, it's a tool that enables others to build their own sites but also their own businesses (and I think entrepreneurs like supporting each other as it helps prove that the rewards do indeed exist). It lets users share, in a sense, in the success to be associated with a product they've used while also being inspired.

Of course, there can be a thin line between sharing and bragging/offending his user base, but I think he treads it quite well.