While growing up in Connecticut, Skot and his parents spent their summers sailing up and down the coast of New England and all over the West Indies. It was on these long trips that Olsen developed his love for the culture and history of sea-faring people. Whale watches and scuba diving cultivated an interest for the strange things that live in the sea such as giant squid, which are the subject of many of his paintings. Small harbor towns and islands provided backdrops for many of the artist's formative years and the people he met there left an impression on him that is now visible in his current series of work.
Having lived near the Florida Everglades for the past 12 years, Skot has also developed an affinity for the Deep South. When not painting giant squid and sea captains, cypress trees and fresh water springs populated with hillbillies are the topics he most enjoys to depict. His work is collected by a diverse international population, spanning from tattoo artists and hipsters to business people and retirees, and he has had the pleasure of exhibiting with and appearing in the same collections as some of the most notable figures in modern art. His work has been featured in numerous national and international publications.