This paper explores how the strategic plays and discipline that chess cultivates translate into strategic thinking, cognitive and leadership abilities, and risk perception in the real business world. Studies cited in this paper show that people who interact with this strategic gameplay regularly generally display higher cognitive and problem-solving abilities and are more adept at dealing with high-stakes situations in the business world. This paper also looks at differences in risk-taking tendencies between different genders. This paper analyses the overlap between chess strategies and abilities that develop from regular interaction with the game, and the critical thinking, and business strategies which likely develop from the game as well, to the point where even the elite credit their success to the game.