Greg and Kim buy a new minivan, and plan to trade in their old car. Jimmy tells Greg trade-ins are a rip-off, and he could just as easily fix it up and sell it himself. Greg agrees to the proposal and lets him keep whatever extra money he makes on top of the trade-in price. So Jimmy fixes up the car, sells it himself, and keeps $3000. He then asks Greg what he should do with the cash since he's never had any before. Greg, stunned at Jimmy's newfound responsibility, suggests he invest it in the stock market and use the profits for his kids' education. Jimmy chooses not to follow that advice to a 'T', however, and instead plunks the money down on a used, dilapidated speedboat -- which doesn't even run. Greg throws a hissyfit over what he considers to be Jimmy's irresponsibility triumph, so much so that even Kim thinks he's being uptight. Jimmy ignores Greg, fixes up the boat and invites the adults out for its "maiden" voyage. At first, Greg refuses to have a good time, but when left alone with the boat after the others go off for lunch, he sees firsthand how much fun sailing is, and how right Jimmy was. He forgets to tie it down when he parks it, though, so Jimmy's amazing technicolor dream boat sets sail for unchartered territories all on its own.