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Leonard Olanna is Iñupiaq from Brevig Mission, Alaska. He comes from a family with a long history of reindeer herding. His grandfather, Harry Olanna, herded for the Lomen Brothers around Brevig Mission in the early 1900s, and in 1970 his father started a herd with reindeer from Wilbur Kakaruk in Teller. Leonard grew up helping his father, and took over management of the herd when his father passed away. That herd crashed, and then in 1994, Leonard started his own herd with animals from the Bureau of Indian Affairs. Having grown up herding and with few job opportunities in the village, Leonard was drawn to reindeer herding. Leonard is also an artist who creates ivory and bone carvings.