Being enterprising has always been a virtue in the US, but historically, there have been limits to how far you would go to make a buck, and people that pushed past those limits would be scorned by the majority. So at the very least, people tried to pretend that they were honest and did "good business" even when they were shysters.

I'd argue it's different today. Social media in particular has convinced a whole generation of people that if you don't have a garage full of supercars by the age of 23, you're a loser, and that there's almost no activity too shameful to engage in publicly in pursuit of wealth.

That's exactly the problem. Any ideal/virtue can be violated as long as they are getting that bag.