Jared was born into the off-airport world of aviation. At the age of 18, his father, Jim Cummings, started an air-taxi service out of Delta Junction that continues to operate to this day. While Jared was growing up, there weren't many maintained runways in that area, so under the watchful eye of his father he learned to land in riverbeds, the tundra, or any patch of dirt wider than a sidewalk. To date he has completed nearly 5500 hours of flying in the state of Alaska. When he is not flying routes for Era Alaska he is operating his own small off-airport operation in Kotzebue known as Golden Eagle Outfitters.