It's not a good article, but the point he makes (at least, conditioning the consumer to expect lower and lower deals) is fair. It's just not new, or limited to grailed...or to fashion...or to anything, really. Grailed is an extension (and affirmation) of an existing culture - their users came from somewhere (SF, SZ, SUFU), and very quickly.
Thing is, fashion's more accessible than ever, but is still enough of a niche interest that everyone feels like an insider (and expects insider deals). Seems more like the article's taking issue with the idea that people who don't meet Eugene's criteria for being worthy and authentic are buying clothes he likes. Unfortunately, there's nothing new there either.