Venture spends 14 months following the dream of entrepreneur Dean Simon of Port-Au-Port, Newfoundland. Simon wants to set up a ski hill in the western part of the province, but it's a constant uphill battle. He is constantly on the move trying to raise money in a depressed economy. He lives in a trailer on the site and takes food donations from his parents and friends to get by. It's clear Simon will go to any lengths to realize his goal, but despite all his personal and financial sacrifices, will he get the breaks he needs to make this happen?