This community service initiative aims to cultivate reflective financial behavior among student startup founders who rely on bootstrapping as their primary funding strategy. Conducted over four months, the program engaged a student-led startup operating in both private tutoring and catfish farming sectors. The initiative addressed common behavioral finance biases—such as overconfidence, sunk cost fallacy, and status quo bias—through contextualized education, reflective journaling, decision-mapping, and low-cost tools like pre-mortem analysis and behavioral checklists. The results revealed tangible improvements in financial self-awareness, decision quality, and emotional regulation. Participants began implementing structured pause points before making financial commitments, differentiated financial logic between service-based and production-based businesses, and revised pricing strategies based on both operational realities and psychological insight. The program also fostered a psychologically safe environment for discussing financial anxiety and learning from failure. This intervention demonstrates that reflective financial education can serve as an impactful and scalable early-stage support model for young entrepreneurs. Its low-barrier, behaviorally-informed approach can be replicated across educational institutions and community-based startup ecosystems, particularly those lacking formal financial mentorship structures. The outcomes suggest that empowering founders to understand their financial behavior is just as crucial as teaching them to manage financial tools.