Originally from Biscay, he was the son of Pedro de Villandrando and Agnes de Corral. He became count of Ribaldo and Valladolid. Around 1410 he arrived in France and was admitted into the company of Amaury de Séverac. He rose to become captain of the routiers, veritable mercenaries in the pay of the seneschal or various other powerful lords and even bishops. When his protector Amaury died in 1427, he entered the service of Charles VII of France. In 1428 he was joined by Juan Salazar, who became his lieutenant. In his early career he is known to have pillaged Treignac, Meymac, and Tulle.