Gates was raised on the family's farm, but did not care for farm life. At an early age, he entered into his first business proposition: to husk a neighbor's corn. His next business venture was to clear some land of timber for another neighbor. Gates earned US$1,000 for this job, selling the timber as firewood to homes and to the railroad. Gates then took the money from this labor and bought a half interest in a threshing machine. As this type of equipment was very new at the time, few farms owned one, so Gates and his partner hired themselves out to work with it at various local farms. After one season, Gates tired of this type of work and he sold his interest in the threshing machine to his partner and another friend. Gates then set himself up as a local grain broker, doing business from the family's home. This business venture was a failure; in an effort to escape farm work, he took to spending time at the railroad depot where he had previously sold firewood. The railroad men remembered him and now asked him to join their poker games. Gates found he had an aptitude for the game and for anticipating the cards men held and how they would play them. With the grain brokerage now forgotten, he was able to make up the losses at the card table.