Entrepreneurship education plays a vital role in driving innovation, economic development, and preparing future leaders to meet the challenges of a rapidly evolving environment. It equips students with the tools necessary to launch and operate successful businesses. This study examines three key areas—cultural attitudes toward entrepreneurship, financing opportunities, and educational support—to better understand how entrepreneurship education is approached in Saudi Arabia compared to the United States. Using survey data from Saudi Arabia, the research explores student and aspiring entrepreneur perspectives on their ecosystem, then reflects and contrasts these findings with academic analyses of American entrepreneurship initiatives. Supported by Monsha'sat, Saudi Arabia's General Authority for Small and Medium Enterprises, the research incorporates a personal case study of the author's journey to establish a Montessori school. Aligned with Vision 2030, Monsha'sat's initiatives provided valuable brainstorming sessions, individual mentoring, and financing guidance, highlighting the impact of institutional support on emerging entrepreneurs. The studies reveal significant differences between the two nations. While Saudi Arabia is rapidly transforming its business landscape under Vision 2030, the United States benefits from an established entrepreneurial culture and extensive funding networks, including angel investors and venture capital. By comparing these systems, the paper identifies opportunities to enhance entrepreneurship education globally, including exploring AI-driven mentoring, promoting international collaboration, and incorporating entrepreneurship into early education.