Navigating the transition from school to work in technology fields presents significant challenges, exacerbated by the rapid pace of technological change and the widening skills gap, a situation further intensified by the COVID-19 pandemic. Major League Hacking (MLH), under the leadership of CEO Mike Swift, aims to bridge this gap by providing developers with real-world experience through initiatives like virtual hackathons and the MLH Fellowship. These programs offer aspiring technologists opportunities to engage in hands-on projects, thereby enhancing their skills beyond the classroom and making them more attractive to potential employers. Hackathons allow developers to apply their theoretical knowledge in practical settings, while the MLH Fellowship pairs them with real-world projects and mentors, fostering an environment for substantial open-source contributions. This collaborative effort not only benefits developers by expanding their portfolios and professional networks but also helps employers identify talent capable of solving real-world problems, ultimately reshaping the way the next generation of technologists is trained and integrated into the workforce.