Sydney (Cocky but likeable, charming, smug)
Terence was raised with a silver spoon up his bottom. However he always loved the tales his mother read to him as a child about scoundrels that came up from the streets and that would do anything necessary to make it big in the world. So much in fact that he ran away from his home of wealth and set himself up in a darker neighborhood using money stolen from his parents, changed his name to Syd and began spreading tails about his past which saw him living a hard life on the streets and doing anything necessary to get to where he now stands.
He found he had a knack when it came to spinning a yarn and his new location combined with his lack of resources gave him no shortage of opportunities to practice breaking and entering, sneaking, and fighting. The innkeeper where he rented a room noticed his capabilities and employed him for security and entertainment in the form of telling jokes and tales, which soon morphed into song and dance.
After being cast out for sleeping with the innkeepers wife he traveled aimlessly before finding he fit in well with a company of Bards whose paths he crossed. The rest is history… or lies, same thing really.