When it was all over, my feeling was that The Hardline may have lost that argument.
It wasn't that Jake seemed too young and callow; it was that The Hardline seemed too old and out of touch. (On this single topic, that is. The C-Nation is aware that Your Plainsman strongly favors The Hard Ones in general.) Oddly enough, the oldest soul present seemed to be Corby.
The Stones are in my wheelhouse, and they're far from my favorite group. Some wonderful songwriting, but to young ears the recordings are a cliche. White guy trying to sound black and look andro. Druggy, gutbucket guitar. Music has indeed moved on, for better or worse. I like the Stones just fine, but it actually surprises me how popular some of the Sixties/Seventies acts remain to the current music-buying generation. That attests to the strength of the music, but it's unsurprising that a guy in his twenties finds it entirely passe.
Consider: When was the last time the generation raised on the Beatles, Zep, and Stones put on a Little Richard or Chuck Berry record? Those records sound tinny, the instrumentation is thin and undistinguished. It's great, historical, spectacular music, but it's now been done to death and not much fun to listen to other than as a curiosity.
So by all means, try to educate Jake on the greatness of the Stones (and I acknowledge their greatness). But if he's not convinced, it's not his problem.
