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Jenna would have never done half as well without Jay there driving and building the empire.



Not clear. Jenna became !!Jenna!! because of someone in Wicked's PR department who managed to insert Jenna into the conscious of mainstream media as a "safe" porn star to reference or interview. Once Jenna started getting attention in the mainstream media that drove sales of her porn stuff and CJ since Jenna is the only porn name most civilians know.

I don't Jay had anything to do with any of this: he happened to pick Jenna instead of Alyssa West to suitcase pimp and got lucky.

As for how well he handled investments for them, we'd have to look closely at the amounts he invested and when, and see just how good the overall returns are. In real estate especially it's possible to get lucky by random chance here and there. On the other hand most suitcase pimps would have blown it all away, so in that sense he's at least above average for his ilk.
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"If they can't picture me with a knife, forcing them to strip in an alley, I don't want any part of it. It's humiliating." - windsock