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-preneurship
02:06 The Journey from Corporate to Entrepreneurship
05:57 Finding the Right Partners
11:07 Lessons from Disney Leadership
18:04 Current Ventures and AI Exploration
23:17 AI Adoption in Fortune 500 Companies
24:32 Transforming Industries with AI
27:34 The Real Estate Industry’s Complexity
30:02 The Role of Real Estate Agents
35:10 Integrating Faith and Technology
40:25 Experiencing the Bible in Virtual Reality

Roger Phipps headshot

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.