In 1990 Stroud became a guide for Black Feather Wilderness Adventures leading canoe excursions into the Northern Ontario wilds. It was also during this time while on a survival course he met his future wife, photographer Sue Jamison. They married in 1994 and together left for a year-long honeymoon in the remote Wabakimi area of Ontario which was to become the basis of the documentary "Snowshoes and Solitude". Afterwards, the couple moved to Yellowknife in the Northwest Territories where Stroud was employed as an outdoor instructor to special needs individuals of aboriginal descent. Stroud and Jamison then settled in Huntsville, Ontario where they had two children and started both the outdoor instructional outfit Wilderness Voice and the media company Wilderness Spirit Productions.