In this rare, no-holds-barred conversation, Adi Soozin sits down with one of South Florida’s most respected and multi-faceted minds in real estate — William Roger Cummings. With five decades of experience, degrees in business, law, and tax, a tenure at Century 21’s University of Learning, and affiliations ranging from Palm Beach Atlantic University to Mensa, this episode is a masterclass in real estate, self-actualization, and building a legacy.
From buying his first property at 21 to mentoring future generations of investors, William reveals the principles that have guided his success: win-win deals, the irreplaceable power of reputation, and the discipline of aligning career with passion. Whether you're an aspiring investor, seasoned developer, or just someone who wants to live a fuller, more intentional life — this episode is packed with timeless strategies, witty wisdom, and deep insight.
You’ll hear stories from his early days in Maine to the booming rise of “Wall Street South” in Florida, the real reason he never launched a fund despite the network to do it, and how elite mental performance, lifelong learning, and fitness have shaped his every move.
Highlights Include:
Why your first multifamily deal can change your life
Secrets to building a real estate dream team
How to thrive across decades of market cycles
The truth about academic degrees and real-world wealth
Finding fulfillment through alignment, not achievement
Plus: his thoughts on AI, IQ, and the art of thinking differently
Connect with William Roger Cummings on LinkedIn and tune in for a powerful reminder: success isn’t just what you build — it’s how you live.