Out-of-school time (OST) makerspaces are spaces for youth to engage in exploratory practices and deepen STEM interests in personally meaningful ways. Many youth—especially teens—additionally benefit from supportive relationships (e.g., caring adult mentors, peer mentors) in these spaces to help them uncover their interests and translate them into long-term trajectories of maker practice. Using a connected learning lens, this paper focuses on supportive adult relationships at a high school OST program (Sunrise of Philadelphia), and the ways in which practices around interest identification and development within its makerspace entrepreneurship program meaningfully impacted learning trajectories for youth by connecting them to new STEM opportunities, knowledge, and experiences. Through an illustrative case study, we present a portrait-of-practice that shows how OST educators facilitated brokering to connect youth to resources, mentoring, materials, and new communities that transcended their specific program. This manuscript contributes to known practices for translating youth interests in makerspaces, including incorporating youth voice and choice and making cultural connections to entrepreneurship opportunities. This case contributes to an understudied area of entrepreneurship education programs and activities that are needed in educational (K-12) makerspaces.