Experts are often viewed as individuals with a vast storehouse of knowledge beyond the normal participants in a domain. In reality, the expert may have just enough additional knowledge beyond those they interface with to propel their team to success. This research explores the accumulation of knowledge and prior skill set necessary to successfully participate in a business simulation emulating the cash-to-cash cycle of a manufacturing/distribution company. Students participate in simulated organizations where the skill level of novice is designated by freshmen/sophomores/juniors with little to no business education. Experts are designated as seniors/graduate students with business educations that include aspects of the entire cash-to-cash cycle of an organization. Comparisons across simulation games indicate that minor background differences in specific participant ability can make significant differences in simulation standings.