What happens when you close a 25-year arc of success — and realize the next chapter demands something entirely different? In this episode of The Emotional Business Show, Olga Skipper talks with Oleg Bibergan, founding partner at S16, a venture fund and community investing in transformative startups. With a background spanning Goldman Sachs, technology, and venture capital, Oleg has built a reputation for clarity and conviction. But behind the professional milestones lies a deeper story of transition, self-discovery, and redefining what success truly means. Together, they explore: How Oleg reflects on the “arc” of his career and life so far, and what it means to enter a new chapter at 40 The role of scaffolding — meditation, journaling, stubborn persistence, and community — in staying centered Why equanimity and emotional intelligence are critical traits for investors and founders alike His shift from data-heavy investing to founder-focused, velocity-driven decision-making The belief that provision = love, and his search for integration between material success and playful creativity How “golden shadows” and curated role models can shape the next evolution of leadership and growth This is a rare look at the inner life of a venture capitalist: how emotional insight, personal rituals, and conscious community building shape not just investments, but identity and impact. 🎧 Tune in to discover what it means to navigate high-stakes decisions without losing connection to yourself, your values, or the people around you. https://www.s16vc.com/