Existential philosophy provides a framework to understand the motivations and strategic decisions of startup founders in navigating uncertainty and limited resources. This study explores the interplay between existential reflection and the 'Arema Spirit,' a cultural ethos in Malang, Indonesia, in shaping financial bootstrapping strategies. Using a qualitative phenomenological approach, data was collected from 30 creative startup founders through in-depth interviews, participatory observations, and qualitative questionnaires. The analysis emphasizes how founders integrate philosophical reflection with local cultural values to balance autonomy, ethical responsibility, and resource efficiency. The findings reveal that existential reflection fosters strategic independence and resilience while the 'Arema Spirit' inspires ethical and community-oriented decisions. This dynamic is encapsulated in the Bootstrapping Existential Reflection Cycle, an iterative framework connecting existential values, bootstrapping practices, and practical innovation. The study highlights the role of cultural identity in entrepreneurial strategy, bridging philosophy, and practice in navigating startup challenges.
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