Sasha Cayward, MSc., transforms venture capital by addressing the systemic psychological neglect of founders who receive massive funding without emotional support infrastructure. Coming from a background in competitive tennis, psychology, neuroscience, and religion at LSE, she transitioned through founding her own company via Techstars before recognizing that founders lack adequate psychological support despite carrying enormous pressure and responsibility. Sasha identifies the "tech bro culture" as a manifestation of toxic masculinity inherited from Wall Street models (Wolf of Wall Street, Gordon Gekko) that rewards aggressive, emotionally unintelligent behavior while prioritizing technical skills over people skills, creating a chicken-and-egg scenario where the VC system breeds founders who fit this destructive mold to achieve 10x returns. She argues it's unethical to give founders substantial funding (£800K-£5M) without psychological support, comparing it to lottery winners where 85-90% go broke within five years due to identity displacement, relationship changes, and overwhelming responsibility they've never experienced. Using the Big Five personality framework (neuroticism, openness, conscientiousness, agreeableness, extraversion), Sasha advocates for psychometric testing during due diligence to assess founder psychology alongside company metrics, recognizing that founders need controlled "craziness" with high neuroticism balanced by other healthy traits. She positions entrepreneurship as the ultimate spiritual journey that surfaces all psychological shadows, traumas, and fears (rejection, visibility, inadequacy), requiring founders to develop self-worth and nervous system regulation while building support systems through coaches, therapists, and peer communities. Sasha draws parallels to professional athletes like Carlos Alcaraz who transformed from emotional volatility to psychological stability through coaching, emphasizing that founder psychology represents a transition from individual sport (pre-revenue) to team sport (scaling) that requires both founder and VC psychological development to create genuinely symbiotic relationships based on mutual accountability rather than traditional power dynamics.