This chapter examines how founders’ personal beliefs and values fundamentally shape fundraising decisions and venture success. It argues that while business goals define what entrepreneurs aim to achieve, their core values—the “why”—are equally critical in determining both strategic direction and investor compatibility. The chapter identifies four common areas where founder and investor values frequently clash: growth versus social impact, lifestyle versus hypergrowth, autonomy versus board oversight, and ethics versus pragmatism. Drawing on legitimation theory and founder testimonials, it demonstrates how misalignment between personal convictions and investor expectations can undermine both venture credibility and founder satisfaction. The chapter provides practical guidance for articulating core beliefs through a personal manifesto, conducting two-way due diligence with potential investors, and using the RaiiSE Canvas to document non-negotiable values—ultimately positioning values alignment as both a strategic compass and a competitive advantage in the fundraising process.