Lenny was born in the continent of Issylra near the southern edge of the Vesper Timberland to Trissys & Fenric Cobbletop. He is one of only a few members of his village that survived the forest fire that claimed his family. Afterward Lenny took to traveling. He soon discovered that he had a keen ability to sense planar disturbances in nature and would seek them out. Most of the time they were destructive creatures that did not belong and he would have to chase it back or kill it but sometimes he would make some new friends. One of which was Nebbik the Harengon wizard who invited him to stay with him in the Faywild for a while.

While there he learned to master the art of the boomerang and at one point even helped Nebbik fend off an attack from a faire raiding party. Eventually Lenny wanted to return to his home plane and as a parting gift gave him two enchanted boomerangs and a journal encouraging him to keep a record of his adventures.