The Massachusetts technology sector is inseparable from the region's educational infrastructure. Beyond formal degree programs, the ecosystem relied on a culture of continuous technical training, mentorship, and hands-on experimentation. Diverse learning environments prepared our tech pioneers to navigate rapidly changing industries. They reflect on their formative experiences within academic departments, secondary school computer clubs, and self-directed garage workshops. These clips examine how specific educators, rigorous curricula, and early access to scarce technical tools cultivated the precise problem-solving methodologies required to build new industries.