To be "with the group" or to "be cool" as determined by your peers. The "trolley" would be something one would want to be on.
One may also want to make it a point of saying that someone is not on the trolley, instead of just saying that they should get on it. This implies that the person is so uncool that they cannot even try and be cool.
Another popular use is pointing out that a particular member of your friends circle is on the trolley in an attempt to rub it in the face of the person who isn't.
This phrase is usually used in a ribbing manner towards friends.
(After making a faux pas, doing something the group would consider uncool, etc) Come on Jason, get on the trolley.
similar to "got off my kool aid," but with way more Italian jealousy. When an absolutely gorgeous redhead is involved, an Italian guy would say "get off my red trolley!"
A Shackteau is a humble, weather-beaten, structurally questionable shelter located in a spectacular or highly coveted place—Wales, Jackson Hole, Sun Valley, Crested Butte, coastal Maine, the Alps—where the building itself may be worth almost nothing, but the dirt, view, access, and mythology make it absurdly valuable.
In use:
Shackteâu - We thought it was an abandoned shed until the realtor called it a rare alpine Shackteâu with unobstructed views and listed it for $2million.