Confessions of a Millionaire
By: Paul Lajoie
Language: en-us
Categories: Business, Entrepreneurship
Confessions of a Millionaire reveals the real stories, hard lessons, and smart decisions behind building wealth through buying and owning businesses. Hosted by Paul Lajoie, the show offers an honest look at what actually works -and what can quietly cost you everything.
Episodes
Most People Would’ve Quit — Caleb Dupuis Didn’t
Dec 15, 2025In 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 an...
Duration: 00:30:17