Pipp comes from a long line of travelling minstrels (his parents are themselves both half-elves). From an early age, he received intensive training from his parents and their troupe in singing, lute, and the flute. It was in this last instrument that Pipp truly excelled, and from the age of 6, he was featured alongside the rest of his family as they performed in village greens across the countryside.
As part of a travelling lifestyle, Pipp learned a little bit of everything: swordplay, magic, history, the customs of nobility, a smattering of languages, and so on. His charmed youth manifests itself in his rosy outlook and incessantly cheerful demeanor. Full of ideals about love, bravery, and the triumph of good, Pipp often displays a certain willful blindness to any ugliness in the world.
Pipp eventually set out on his own, looking for new stories to tell and songs to sing. Adventuring parties seem to put up with him for some reason.