🎙️ #51 What Happens After a $4 Billion Exit - Walter de Oude’s Next Chapter

From insurance disruption and billion-dollar exits to rethinking how money should feel, Walter de Oude has spent two decades building companies that challenge the way we think about value, trust, and happiness. In Episode 51 of The Generalists, Walter sits down with Michael and Raz to unpack the journey from actuary to entrepreneur — from founding Singlife, Singapore’s first homegrown digital insurer that scaled to over $4 billion AUM, to launching Chocolate Finance, a new kind of fintech designed to make money feel good. He shares how the experience of building — and later leaving — a billion-dollar company reshaped his view of work, purpose, and leadership. Walter explains why meaning and happiness, not résumés or capital, are the true measures of success — and why every founder should wake up and ask one thing: Do I love my life? 📖 What You’ll Learn in This Episode • Why “Do I love my life?” is the ultimate founder metric • How Walter built Singlife to fix an industry that “sucked” • Why Chocolate Finance was designed as a happy place for money • How purpose and impact outweigh skills or credentials • The mindset shift from corporate operator to infinite-game founder • Lessons on balance, family, and designing a fulfilling life 👥 Hosts • Michael Smith Jr.: https://www.linkedin.com/in/smittysgp/ • Raz Kotler: https://www.linkedin.com/in/razko282/ 👤 Guest • Walter de Oude - Founder of Singlife & Chocolate Financehttps://www.linkedin.com/in/walterdeoude/ 🔔 If you’ve ever questioned what success really means — and how to build a life you actually love — this video is for you. 👉 Subscribe Now: https://www.youtube.com/@TheGeneralistsPodcast 🔗 Resources & Links Mentioned 🚀 Companies & Platforms • Chocolate Finance – https://chocolatefinance.com • Singlife – https://singlife.com 📚 Books & Ideas • The Infinite Game - Simon Sinek https://www.amazon.com/Infinite-Game-Simon-Sinek/dp/073521350X • Adrift: America in 100 Charts - Scott Galloway https://www.amazon.com/Adrift-America-100-Charts/dp/0593540401 🧠 Concepts & Frameworks • The Infinite Game Mindset - Simon Sinek https://simonsinek.com • Trust in Fintech - Accenture Study https://www.accenture.com/sg-en/insights/financial-services/fintech-trust • Founder Resilience - Harvard Business Review https://hbr.org