Because of his previous experiences in shipping and fuel supply, Hill was able to enter both the coal and steamboat businesses. In 1870, he and his partners started the Red River Transportation Company, which offered steam boat transportation between St. Paul and Winnipeg. By 1879 he had a local monopoly by merging (with Norman Kittson). In 1867, Hill entered the coal Business, and by 1879 it had expanded five times over, giving Hill a local monopoly in the anthracite coal Business. During this same period, Hill also entered into banking and quickly managed to become member of several major banks' boards of Directors. He also bought out bankrupt businesses, built them up again, and then resold them—often gaining a substantial profit. Hill noted that the secret to his success was "work, hard work, intelligent work, and then more work."