Although researchers have shown interest in videogaming since the early 2000s, the hyper-competitive world of "esports" has received less attention. However, multi-million dollar gaming tournaments--such as the 2019 "Fortnite" World Cup--now make headlines and spark national discussion. Similarly, colleges and universities have begun offering athletic scholarships to students who excel at games like "League of Legends" and "Overwatch." Consequently, this present study aims to shine a light on the values, beliefs, and practices of gaming's most "hardcore" players and communities. To better understand how these competitors improve their in-game skills, the author adopted a "connective ethnographic" approach and immersed himself in the day-to-day activities of a collegiate esports club. This process involved attending club meetings, interviewing members, and participating alongside players as they competed with and against one another in the game of "Overwatch." As the investigation unfolded, the study narrowed its focus to explore how club members leveraged technology--like the livestreaming platform of "Twitch" and social network of "Discord"--to engage in collaborative observation, analysis, and self-critique. By drawing and iterating upon Gee's "affinity spaces" and Rogoff's theories of "learning by observing and pitching in," this study suggests that competitive gamers naturally create and seek out their own learning ecologies. More specifically, these gamers come together to form "observational and analytical gaming ecologies" (OAGEs) wherein members find the cultural tools necessary to experience and re-experience gameplay from multiple perspectives. By harnessing virtual worlds and emerging technologies in compelling new ways, these gamers are thus reimagining how people learn from their peers and from their own failures. [The dissertation citations contained here are published with the permission of ProQuest LLC. Further reproduction is prohibited without permission. Copies of dissertations may be obtained by Telephone (800) 1-800-521-0600. Web page: http://www.proquest.com.bibliotheek.ehb.be/en-US/products/dissertations/individuals.shtml.]