Episode 48: From Fintech to Faith Tech – The Mind of a Modern Multipreneur

From FinTech to FaithTech: Inside the Mind of a Modern Multi-preneur “Disney taught me how to develop teams.” That line from Roger Phipps stayed with me long after this conversation ended. In this episode of the Rebellious Times Podcast, I sat down with Roger Phipps — a serial entrepreneur operating across FinTech, PropTech, AI, construction technology, communication strategy, and immersive faith-based virtual reality experiences. This wasn’t a typical startup conversation. Instead, we explored the mindset behind multi-preneurship, the realities of scaling companies, leadership lessons from Disney, and how AI is reshaping industries faster than most businesses realize. What Is Multi-preneurship? Roger describes multi-preneurship as managing multiple businesses simultaneously. However, he explains it with a more memorable analogy: Entrepreneurship is jumping off one cliff and building your parachute on the way down. Multi-preneurship is jumping off multiple cliffs at the same time. That mindset has defined much of Roger’s career. The Pivot from Corporate Leadership to Entrepreneurship Before becoming an entrepreneur, Roger spent years in leadership roles at Fortune 100 and Fortune 500 companies. At one point, he believed he had reached the destination: Executive leadership Financial success The dream home Corporate achievement Then life changed. A major personal transition forced Roger to reevaluate what he wanted from work and life. That became the inflection point that pushed him into entrepreneurship. What followed was a rapid rise inside a FinTech startup focused on solving problems inside the credit union industry. Episode Chapters 00:00 Introduction to Multi-preneurship02:06 The Journey from Corporate to Entrepreneurship05:57 Finding the Right Partners11:07 Lessons from Disney Leadership18:04 Current Ventures and AI Exploration23:17 AI Adoption in Fortune 500 Companies24:32 Transforming Industries with AI27:34 The Real Estate Industry’s Complexity30:02 The Role of Real Estate Agents35:10 Integrating Faith and Technology40:25 Experiencing the Bible in Virtual Reality Building a FinTech Business by Solving Industry Pain Points Roger explains that the credit union space had been underserved technologically for years. Instead of building generic tools, the company focused specifically on the unique operational needs of credit unions: Digital marketing Software Hardware Cybersecurity Digital branches The key insight was simple: Understand the industry deeply enough to solve problems others ignore. That focus helped the business scale rapidly. Disney Leadership Lessons One of my favorite sections of the episode was Roger’s discussion about leadership training at Disney. Unlike many corporations, Disney focused on holistic leadership development: Mental well-being Physical health Communication Emotional intelligence Team development Roger explained how Disney actively invested in helping leaders become better humans first — not just better managers. That philosophy heavily influenced how he later built and managed entrepreneurial teams. Why Most Businesses Still Struggle with AI The AI section of this conversation was especially interesting. Roger argues that only a small percentage of Fortune 500 companies are using AI effectively today. The reason? Most businesses struggle to diagnose their own inefficiencies. Instead of simply adding AI features to existing systems, Roger believes businesses should rethink workflows entirely from the ground up. One major theme throughout the episode: AI should enhance human capacity — not simply replace people. Real Estate Technology Is Still Broken Roger also discussed how industries like: Real estate insurance construction healthcare have fallen behind technologically. One of the projects he is working on uses AI-powered video and audio analysis to automate property inspections and asset management workflows. Instead of replacing workers, the goal is to eliminate repetitive manual tasks and increase operational capacity. That distinction matters. Faith Meets Technology Toward the end of the conversation, Roger shared one of his most fascinating projects: A virtual reality Bible experience. The idea is to allow users to immerse themselves visually inside biblical environments while reading scripture. Using VR technology, users can: Explore historical environments Experience biblical scenes visually Participate in remote Bible studies Better understand historical context The project combines: Faith archaeology education immersive technology in a surprisingly thoughtful way. Final Thoughts This episode was one of the most wide-ranging conversations I’ve had on the podcast so far. We covered: entrepreneurship AI leadership team culture real estate faith virtual reality communication strategy and what it really means to build multiple businesses at once. Roger’s story is a reminder that entrepreneurship is rarely linear. Roger Phipps links: www.vpohomes.com www.prezaid.com www.projectaidra.net www.myvrbible.com LinkedIn