Most People Would’ve Quit — Caleb Dupuis Didn’t

In this episode of Confessions of a Millionaire, host Paul Lajoie sits down with Caleb Dupree, a Texas-based investor and entrepreneur, to unpack the real, behind-the-scenes journey of building wealth through real estate and business ownership.

Caleb shares how he started with a single $53,000 rental property while working a full-time banking job and gradually scaled to owning 35+ single-family homes, a 20-unit apartment complex, and eventually a marina—an acquisition that pushed him from passive real estate into a true operating business. He openly discusses the fear, mistakes, and lessons learned along the way, including underestimating capital expenditures and operational complexity.

The conversation highlights key themes: taking action without perfect information, leveraging relationships and creative financing, the importance of spousal support, and why bigger deals can sometimes be easier than smaller ones. Caleb also explains his decision to leave his W-2 job, the mindset required to make that leap, and how his personal network and mastermind group accelerated his growth.

This episode is an honest look at how wealth is built after hours, through grit, calculated risk, strong relationships, and a willingness to learn by doing—rather than waiting for everything to feel comfortable.