Incidentally: blogging is still a terrible way to make money for the vast majority of bloggers. The really successful ones generally use it as a friendcatcher for related business. It isn't even the most efficient friendcatcher, either.
I can affirm we eat up the stuff he promotes. Dark Sky, Pixelmator, Fantasical. I heard them all first on DF and bought each (and more). He's usually spot on in the things he promotes to (I don't think he accepts sponsors for products he doesn't think are great).
Paying for ads on his site I believe are totally worth it.
Wait, he has paid membership too? Membership in what? His blog?
I am not sure if every week is really booked though and if its really for the price listed, so i would take that with a grain of salt. No doubt hes making a ton of money though.