He/Twitter will definitely make money off of this. My point in him being a "stupid businessman" is that he'd probably make more money if he charged $4.99 a month as opposed to four times that. Instead of relying on the fringe or elitist for revenue, he could rely on a lot more than those folks for a lot more money. For every verified user ($20) there's at least 50 more standard users that would easily pay $5 a month to get rid of ads and have that verified checkmark.
So, yeah.. He's out of touch AND doesn't give a damn.