It's normally when people throw money at strippers and after they've dont their show, they collect the money, which in this case would be stattered like leaves... and how do you collect leaves? With a rake. So think of the leaves being money.
Ex. 1) After she finished her show, her boss told her to rake it up.
12 step recovery jargon referring to someone new who talks about how great life is, now that they'resober. Usually meaning that the person is out of touch with reality.
The new guy seems pretty happy for a dude who has no job, no money and no family. He must be on a pink cloud.