Waydon was born into the famed and illustrious House Arkona, thank you very much. This family has been a ruling class in Korvosa for years, to hear them tell it. However, they just recently regained their wealth, and were mighty poor at for quite sometime. The House Arkona maintains their wealth by supporting the Cerulean Society's efforts, among other underground businesses, in Korvosa. Waydon was appointed to watch over the Society and make sure everything was in order and that the family continued making money. Waydon decided that the easiest way to do this, was to join the Cerulean Society, so that is what he did.
Waydon worked within the Cerulean Society for years, always making sure that the House Arkona was profiting. He was a key part in the murder of 3 men who had been caught gambling with the House Arkona's money, and never saw a problem in doing so. Waydon always made sure never to completely implicate himself in any of the Society's dealings, always staying out of the spotlight.
He was taught very few things at a young age by his father. Two of those things were: Do whatever you must do to make money, and always, always, always, aim to hurt the Magnimars and the Shoantis. Waydon never forgot these two things, even after his father passed away into the clutches of Aroden.
He specifically remembered those things when he realized a way to bring Magnimar to a war with a neighboring city and its allies. The mayorof this city was a Magnimar native, but she had randomly left Magnimar and moved to this new city. The goal was to sneak into this city, kill the mayor, then make it look as if Magnimar was responsible for her murder, and the city would mount forces to attack Magnimar for killing their beloved mayor. Magnimar would crumble and Waydon would be the genius who allowed Korvosa to become the last major Cheliaxian city in Varisia. The town he had to inflitrate was Sandpoint, and the mayor was Kendra Deverin.