Pilot was born in a small village, Shorobe, on the edge of the Okavango Delta in Botswana. He spent his early life in the bush and on a remote cattle post attending Shorobe Primary School. Shopping trips with his parents would entail travel to Maun by Mokoro (a traditional mug canoe). Isaac could not attend high school, as his father passed away, however living in the Okavango Delta enabled him to learn about birds and the wildlife in the area.
He was employed by Wilderness safaris in Botswana, where he worked from October 1986 till the end of 2005 as a Safari assistant for the proprietor of the company in the then Overland Department. In 1991 he qualified as a professional safari guide and assisted overland safaris taking guests through most of northern Botswana, Zambia and Zimbabwe. He then learned the operations and logistics of the company by managing stock and food orders, to the cooking details in camp, scheduling etc. Through the year, the department changed to Guided Safaris and then finally to Explorations. Pilot was confident with the change and guided many different safaris on schedules. Through his guiding Isaac had the opportunity to travel through Namibia, South Africa and Zimbabwe at a Regional level and travelled to Churchill Manitoba, Toronto and Miami on an International level. Throughout his travels, Isaac made many friends from all over the world, one of which included Steve Morello, field director of Natural Habitat Adventures (based in Colorado, USA). Steve was so impressed with Isaac that he invited him to join a Polar bear watch in Churchill, Manitoba. On the west coast of the Hudson Bay, Churchill becomes a stopover for thousands of migrating bears in the Canadian autumn. This amongst other trips, has given Isaac an edge and a greater understanding of international cultures. He attended and passed various professional guiding, walking, field & weaponary skills training courses, including the advanced guides training course, in Botswana, South Africa and Zimbabwe.