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All opinions expressed by the guests are their own. 9×90™ and its affiliates do not endorse or guarantee any specific outcomes discussed in this episode. This podcast is for informational and entertainment purposes only and does not constitute financial, legal, or investment advice. Listeners should conduct their own due diligence and consult with professional advisors before making any investment or business decisions. Nothing discussed in this episode constitutes an offer to sell, or a solicitation of an offer to buy, any securities. Any such offer or solicitation will be made only through official offering documents and to qualified, accredited investors, in accordance with applicable securities laws. The views expressed by guests are their own and do not necessarily reflect those of the host or 9×90™.

About this guest

For those of you who do not know William Roger Cummings,

1. Real Estate Veteran with 50+ Years of Market Mastery – William Roger Cummings launched his real estate career at just 21 years old and has spent over five decades navigating and thriving through multiple market cycles—offering a rare blend of endurance, foresight, and wisdom few in the industry can match.
2. Multidisciplinary Strategist with JD, MBA, and Accounting Expertise – Holding advanced degrees in business, accounting, and law, Roger brings an unmatched analytical edge to every negotiation, contract, and investment decision—arming his clients and students with a legal and financial framework for long-term success.
3. National Educator & Mentor Behind Century 21’s Agent Development – As the former Director of Century 21 University of Learning, Roger led training across South Florida for over a decade, shaping thousands of agents and elevating the professional standard of real estate education throughout the region.

About this episode

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.

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Show Notes Generated by Gemini

These show notes were generated by AI

• Introduction to William Roger Cummings Adi Soozin introduced William Roger Cummings, highlighting their extensive five-decade career in Palm Beach real estate, academic background including degrees in business, an MBA, and a JD, and previous role as an adjunct professor at Palm Beach Atlantic University. Adi Soozin praised William Roger Cummings’ deep expertise and ability to adapt to market cycles. William Roger Cummings expressed their excitement to be on the podcast.
• Early Real Estate Ventures and Advice William Roger Cummings purchased their first property at 21 with guidance from their father, who was a real estate investor. William Roger Cummings emphasized that investing in real estate early is beneficial. They advised students to resist selling income-producing properties and to keep raising rents to cover expenses.
• Impact of Academic Background Adi Soozin inquired about how William Roger Cummings’ degrees in business, accounting, and law have shaped their real estate approach. William Roger Cummings explained that they bought their first property during law school and later pursued a master’s in tax law. They underscored the importance of having a good team of professionals, comparing it to a soccer team needing a captain.
• The Start in Real Estate and the Power of Multiplexes Adi Soozin shared a similar experience of a cousin starting their portfolio by living in one unit of a multi-family property and renovating others. William Roger Cummings agreed, noting the financial advantages of living in a property with up to four units, as tenants can help pay the bills. Adi Soozin emphasized that this is a significant advantage in the US that is often underutilized.
• Importance of Professional Teams and Leadership William Roger Cummings stressed the significance of using the correct professionals and assembling a team for growth. Adi Soozin concurred, stating that the best teams are built with the best people and warned against trying to handle everything alone. William Roger Cummings added the importance of having a good team captain, who might not always be oneself. Adi Soozin likened their managing partner to a coach who knows how to build an all-star team.
• Role at Century 21 University of Learning Adi Soozin acknowledged William Roger Cummings’ decade-long tenure as a director at the Century 21 University of Learning. William Roger Cummings explained that they oversaw training across several counties in South Florida, preparing students for licensing exams in mortgage and real estate brokerage. They also conducted satellite classroom tours statewide for mandatory continuing education, allowing them to interact with many agents and understand different market cultures.
• Transition from Maine to South Florida Adi Soozin noted William Roger Cummings’ reach across the East Coast and inquired about their primary operating locations. William Roger Cummings stated that while they appreciated their heritage in Maine, they recognized the stronger future prospects in South Florida from a young age. A business trip to Miami Beach at 15 solidified their decision, leading them to apply only to the University of Miami.
• Personal Anecdotes and Preferences Adi Soozin and William Roger Cummings shared humorous anecdotes about adjusting to different climates and cultural norms, including experiences with cold weather and Italian shoe etiquette. The conversation shifted to William Roger Cummings’ signature hat, which they confessed was primarily due to hair loss rather than a deliberate fashion statement. They also noted the importance of hats in sunny Florida for skin protection, referencing the loss of Jimmy Buffett to skin cancer.
• Community Engagement and Networking Adi Soozin asked how William Roger Cummings’ involvement in organizations like Kiwanis International and American Mensa has complemented their professional life. William Roger Cummings explained that allowing people to get to know them better fosters trust and relationships that can lead to business. Adi Soozin shared their philosophy of needing to enjoy spending time with investors outside of business. William Roger Cummings emphasized the importance of aligning values and not forcing business relationships with everyone.
• Involvement with Palm Beach Atlantic University William Roger Cummings discussed their closer involvement with Palm Beach Atlantic University and their admiration for Dean Brian Strow of the Rinker School of Business. They highlighted the school’s AACSB accreditation, faith-based values, and focus on American free enterprise. Adi Soozin, an alumna, praised the safe campus environment, career-focused students, and emphasis on health. William Roger Cummings also mentioned the strong leadership of President Deborah Schwin and the university’s excellent pre-pharmaceutical program.
• Growth in South Florida Real Estate and Educational Initiatives William Roger Cummings emphasized the significant real estate development in South Florida, now known as the “Wall Street South” region, citing projects like the Waldorf Astoria in Miami. Adi Soozin agreed, noting the influx of tech and venture capital, suggesting the region is becoming the next New York City. William Roger Cummings mentioned high-profile individuals like Ken Griffin investing heavily in the area. They are working to enhance the curriculum at PBA to better align students’ degrees with career paths in real estate, advising them to balance career advancement with personal life and passive real estate investments.
• Philosophy of Win-Win Opportunities Adi Soozin discussed William Roger Cummings’ philosophy of seeking win-win opportunities in transactions, a practice also followed by their family. William Roger Cummings elaborated that their extensive familiarity with South Florida allows them to provide informed suggestions to clients, matching them with suitable properties and sellers for mutually beneficial outcomes. They also shared their approach to dealing with unreasonable offers or asking prices by seeking logical justifications to facilitate smoother negotiations.
• Importance of Reputation and Long-Term Relationships Adi Soozin and William Roger Cummings underscored the importance of maintaining a good reputation in the real estate industry. Adi Soozin noted how quickly a negative reputation can spread, effectively locking individuals out of future deals. William Roger Cummings highlighted their ability to move freely throughout South Florida without fear of negative encounters due to past dealings.
• Adapting to Market Shifts and Advice for New Agents Adi Soozin asked how William Roger Cummings has adapted to the various shifts in the real estate market over his long career and what advice they have for new agents. William Roger Cummings pointed out that building a sales career in real estate takes time and requires leveraging one’s network. They advised new agents to be prepared for a potentially lengthy period before consistent commission income and suggested it’s okay to maintain another job while transitioning.
• Reasons for Not Starting a Real Estate Fund Adi Soozin inquired why William Roger Cummings, with their extensive network and experience, has never started a real estate fund. William Roger Cummings explained that operating a fund is a significant amount of work, akin to another full-time job. They prefer to focus on their current work and recommend others who operate REITs to their investors, believing in concentrating on what they enjoy and do best.
• The Concept of Self-Actualization Adi Soozin noted William Roger Cummings’ repeated emphasis on self-actualization and questioned why it isn’t prioritized more often. William Roger Cummings believes that stress, stemming from trying to be someone one is not or appealing to incompatible people, underlies many issues in health, relationships, and employment. They shared their own experience leaving a law firm to pursue a more fulfilling career in real estate.
• Insights on Learning from People and Philosophy Adi Soozin shifted the topic to philosophy books that William Roger Cummings reads. William Roger Cummings responded that they learn more from “people books,” admiring individuals for doing what they love well. They shared an example of their respect for a librarian who enriches the community through their work.
• Influence of Fitness and Wellness Adi Soozin acknowledged William Roger Cummings’ interest in fitness and wellness and asked how these pursuits influence their professional life. William Roger Cummings stated that good health habits enable them to be active and enjoy life, aligning with their personal motto of “never stop”. They recounted evolving away from unhealthy habits in their younger years, recognizing their long-term detrimental effects. William Roger Cummings shared an anecdote about a recent physical exam where their excellent respiratory health was noted, attributing it to not smoking. They also discussed their past participation in marathons as a testament to the benefits of a healthy lifestyle.
• Contact Information and Professional Affiliations Adi Soozin asked for the best way for people to contact William Roger Cummings for mentorship or investment opportunities. William Roger Cummings recommended connecting and sending a direct message on LinkedIn due to their frequent travel and preference for giving undivided attention during meetings. Adi Soozin then inquired about the two pins William Roger Cummings was wearing. They explained that one pin represents Palm Beach Atlantic University, which they wear with pride alongside the president, and the other is for the Mensa organization.
• Involvement with Mensa Adi Soozin asked about William Roger Cummings’ involvement with Mensa. William Roger Cummings shared that they were formerly the “Lok Sec” (local secretary) of the Palm Beach County chapter. They explained Mensa’s criteria for membership (scoring in the top 2% of any internationally recognized IQ test) and their experience leading the local chapter, which included a diverse group of intelligent individuals. William Roger Cummings mentioned John Hillis, the city of West Palm Beach librarian, as an inspirational figure from their time as Lok. They also recounted their approach to Mensa gatherings, including social events like disco nights.
• Academic Experiences and Perspectives on Learning Adi Soozin shared their own experience with IQ tests for business school admission. William Roger Cummings reflected on their own academic journey, noting that despite not being a top student in high school due to frequent moves, they were able to succeed in higher education and obtain multiple degrees out of personal interest. Adi Soozin and William Roger Cummings exchanged anecdotes about their differing experiences with academic writing, with Adi Soozin preferring tests over papers and William Roger Cummings recounting a challenging experience writing their master’s thesis but ultimately learning and succeeding. Adi Soozin shared their unexpected career turn into writing a successful marketing book, despite their earlier aversion to extensive writing. They discussed how their “tertiary effects” thinking, potentially influenced by a Mensa-like mindset, required them to break down complex ideas into step-by-step explanations for their book. William Roger Cummings noted that this detailed approach benefited readers with different thinking styles. They discussed the difference between linear and non-linear thinking.
• Final Thoughts on Personal Fulfillment Adi Soozin concluded the interview by asking if William Roger Cummings had any final thoughts to share . William Roger Cummings emphasized the importance of considering what brings personal fulfillment, what one enjoys, and how to enrich one’s own life and the lives of others in a natural way, encouraging listeners to find their identity . Adi Soozin thanked William Roger Cummings and the audience for tuning in .

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Transcript

This transcription was generated by Gemini & edited by ChatGPT

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Adi Soozin:
Ladies and gentlemen, welcome to another episode of 9X90™. Today, we are joined by a very special guest — a true icon in the Palm Beach real estate arena.
He purchased his first property at just 21 years old and has spent the last five decades mastering the industry. His longevity and adaptability through multiple market cycles speak to not just experience, but deep expertise.
Roger holds a business degree, an MBA, and a JD — making him, in my opinion, a Jedi master of negotiation, opportunity-spotting, and structuring world-class deals. He also served as an adjunct professor at my alma mater, Palm Beach Atlantic University. His academic background gives him a uniquely strategic and analytical edge — not just in deal-making, but also in contract law and investment advisory.
So, without further ado — the man, the myth, the legend: William Roger Cummings. William, how are you?

William Roger Cummings:
I’m doing wonderful, and thank you so much for having me on this amazing podcast. We’re all familiar with 9X90™, and it’s truly a pleasure to be here.

Adi Soozin:
You bought your first property at 21 — that’s almost unheard of, especially back then. Nowadays, you see a few software kids doing it, but 50 years ago? That was rare.

William Roger Cummings:
Yes, my father was instrumental in guiding me. He was a real estate investor himself and told me early on: “Paying interest is bad. Collecting rent is good.”

Adi Soozin:
Ah, so you’re second-generation. I didn’t realize that! I’m fifth-generation — and you’re right, having access to your parents for real estate advice is a total game changer.

William Roger Cummings:
Absolutely. That’s why I try to give back by working with students, especially from Palm Beach Atlantic University, to offer a bit of guidance. At that age, you often don’t yet have the confidence or understanding. But the earlier you get into real estate, the better.

Adi Soozin:
No doubt about it. Especially right now — with certain asset classes declining, people who’ve only been in the game for three to five years are underwater. And we’re coming in like white knights, because they had no idea how to handle market corrections.

William Roger Cummings:
Exactly. The longer you’re in the business, the better you get. I’ve bought properties that I sold for two, three, even four times what I paid — and if I had held onto them, they’d be worth 25 times that today. So I always tell students: resist the urge to sell your income-producing properties. Just keep raising the rent.

Adi Soozin:
Yes! With your academic background — business, accounting, and law — how have those disciplines shaped the way you approach deals and client relationships?

William Roger Cummings:
It all happened naturally. I bought my first property during my second year of law school, with help from my father. I lived in one of the units and managed the rest while splitting my studies between Boston and Portland, Maine. Later, I was accepted into the University of Miami Law School for a master’s in tax law.
When I moved to Miami, I left the property in Maine under the management of a former girlfriend from high school. We made a business arrangement, and that partnership turned into a long-standing friendship.

Adi Soozin:
One of my older cousins did the same — bought a triplex, lived in one unit, renovated the others, then moved out. It’s such a smart way to build your foundation.

William Roger Cummings:
It really is. If it has a roof, four walls, plumbing, and electricity — that’s a solid start. As long as it’s four units or fewer, you can qualify for residential financing, live in one, and have the others help pay your mortgage.

Adi Soozin:
Yes! That’s such a powerful advantage in the U.S. — and too few people take advantage of it. In other countries, people would kill for that kind of opportunity.

William Roger Cummings:
Absolutely. And with my background in business and accounting, I realized early on how crucial it is to have a good CPA. You need the right professionals to help you build — an accountant, a real estate attorney, a broker, maybe even a mentor. That team is everything.

Adi Soozin:
Couldn’t agree more. Real estate isn’t golf — it’s soccer. Or maybe football. You need a full team to win. People who try to do it all themselves? They burn out or break.

William Roger Cummings:
Exactly. And with your soccer analogy — every good team also needs a captain. That might be you, or someone you designate, but you need leadership. A strategist. A cabinet of advisors.

Adi Soozin:
Exactly! The managing partner at the fund I’m at — I call him “Coach.” I’ll say, “Thanks, Coach.” He laughs, but he fully embodies that leadership role. That’s the key: building an All-Star team and knowing how to use it.
When you’re working with high-value assets, operations and execution determine whether a building becomes a loss… or delivers a 2x, 3x, even 4x return. It’s all about the equity multiple.

William Roger Cummings:
It really is. And when you have good inspectors, reliable contractors, and subcontractors you can trust — it makes all the difference in how fast and effectively you can move.

Adi Soozin:
So true. Now, you also served as Director of the Century 21 University of Learning for over a decade. What were some of the major initiatives you led there — and how did they impact agent development in South Florida?

William Roger Cummings:
Thank you for asking. Yes, I had the privilege of leading Century 21’s University of Learning for South Florida — covering Miami-Dade, Broward, and Palm Beach counties. We had multiple classrooms in each area, and licensed instructors preparing students for the state exams — whether for real estate brokerage or mortgage licensing.
I was also selected to lead a satellite classroom tour across Florida twice a year. We’d visit cities like Jacksonville and Naples, training new licensees. Florida has rigorous continuing education requirements, and I was proud to be part of that. I met agents from all over the state and gained an appreciation for the diversity of real estate cultures — especially compared to my experience in Maine.

Adi Soozin:
Wow, so you were really covering the entire East Coast. Would you say your work has primarily been focused in Florida and Maine?

William Roger Cummings:
Yes — Maine will always be part of my heritage. It was my father’s home. But I knew early on that Florida offered greater opportunity. When I was 15, I joined my dad on a business trip to Miami Beach in the middle of winter — and it made quite an impression.
So when it came time for college, I only applied to one school: the University of Miami. Thankfully, they accepted me.

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Adi Soozin: Oh my goodness, that’s funny. When I was living in Europe — I spent about five and a half years there — I came back to New Jersey one January, and it was absolutely freezing. I remember walking just two blocks in below-zero temperatures to my dad’s office and saying, “I love you, but I’m moving to California.”

William Roger Cummings: I had a bit of a shocking moment in Germany myself. I was a cast member on a German reality TV show and went there for some promotional events. When I got off the plane and made my way through the parking lot, I realized very quickly that Italian loafers are not ideal for German snowbanks — my feet were freezing.

Adi Soozin: Oh my gosh, that reminds me of a hilarious Italian shoe story. You know how in Italy they practically worship their shoes? One day, I was at the library and lost track of time — I just love getting lost in books. When I finally went to check out, it was pouring outside. The woman behind the desk looked at me and asked, “Would you like a bag for your shoes?” I said, “What do you mean?” She told me the parking lot was flooded and warned that I’d ruin my shoes if I wore them out. I was like, “So you’d rather I walk barefoot in freezing rain than risk damaging my leather shoes?” She said, “Yes. This is the Italian way.” None of my American friends ever believe that story!

William Roger Cummings: Honestly, it makes a lot of sense. Italian shoes have gotten even more expensive lately.

Adi Soozin: I know, right? You have to shop during the January or August sales — otherwise, forget it.

William Roger Cummings: Exactly.

Adi Soozin: But the quality is incredible. The craftsmanship is unreal — they study human anatomy to shape shoes that are not only beautiful but also comfortable. In the U.S., we just don’t see that level of design detail, especially when it comes to comfort.

William Roger Cummings: You know, we’re off on a bit of a fashion tangent here, but I understand the passion. I once met Manolo Blahnik before a show — very charming guy. He looked at me and said, “I love your hat.” I thought, “Wow, thank you!”

Adi Soozin: That’s amazing! I remember walking around Clematis Street about ten years ago, and you were still wearing that hat. Someone saw you and whispered, “That’s the godfather of real estate in South Florida.” You were just sitting outside Starbucks, but they said it with so much reverence. Has the hat always been your signature?

William Roger Cummings: Honestly, I didn’t choose it as a signature look. I started wearing it because of a bit of hair loss on top. Sometimes male pattern baldness turns you into a scientist — you start experimenting with solutions!

Adi Soozin: Haha, I totally thought it was a branding move — like Taylor Swift has her red lipstick, and you have your iconic hat.

William Roger Cummings: I mean, I don’t know why more people in Florida don’t wear hats. It’s so sunny here.

Adi Soozin: Right?! Between the sun exposure, skin cancer risks, and even eye cancer — it’s intense.

William Roger Cummings: Sadly, we recently lost Jimmy Buffett to skin cancer. He really embodied the South Florida beach lifestyle. It was painful and ironic to lose someone so symbolic of the coastal way of life.

Adi Soozin: That’s heartbreaking. And skin cancer can spread so aggressively. It’s wild.
But, back to real estate — and sorry for all our side tangents!
As someone who’s led in organizations like Kiwanis International and American Mensa, how has your community involvement shaped your professional journey?

William Roger Cummings: I think letting people get to know you — the real you — helps build trust. Not everyone will be a fit, and I don’t try to pursue everyone as a client. But those who resonate with me are usually people I connect with on a deeper level. That shared understanding leads to meaningful relationships — and often to long-term business.

Adi Soozin: Someone recently asked how I choose investors for our real estate fund. I said, “If I can’t sit and enjoy dinner with them once a month, I don’t want their money.” It’s not just about trust — you have to like each other too.

William Roger Cummings: Exactly. I’ve met people whose morals or priorities just don’t align with mine — and that’s okay. It’s better for both sides to go their separate ways than to force a working relationship.

Adi Soozin: Totally agree. I think young people often feel pressure to get along with everyone, but you don’t have to. You just need to find a few good people — those who share your values — and build with them.

William Roger Cummings: One of the reasons I’ve gotten more involved with Palm Beach Atlantic University is because of that values alignment. I’ve always known about the school, but recently I had lunch with Brian Stroud, Dean of the Rinker School of Business. He asked me to join the Advisory Board, and I was impressed. He and his wife are both PhDs, lifelong educators, and devoted parents to four high-achieving children.
Palm Beach Atlantic stands for faith, family values, and American free enterprise — so I was all in.

Adi Soozin: It really is a great school. I remember feeling completely safe on campus — something many young women can’t say about their college experience. People there were so focused: career-driven, health-conscious, and intentional about networking. It was like being in a bubble.
My brother went to Southeastern in North Florida and would joke, “At my sister’s school, the girls work out and eat healthy. At my school, it looks like the girls bake pies — and then eat them.”

William Roger Cummings: [laughs]

Adi Soozin: I didn’t realize how rare it was to be surrounded by such health-conscious, ambitious young people until I moved to Italy — the value system there was completely different.

William Roger Cummings: What’s also great about PBA is the leadership. President Deborah Schwinn kept the campus open during COVID while keeping everyone safe. People questioned it, but she said, “I’m a medical doctor.” Her leadership was courageous and deeply effective.

Adi Soozin: PBA also has one of the best pre-pharmacy programs in the country. I earned my bachelor’s in Medicinal and Biological Chemistry there.

William Roger Cummings: Impressive.

Adi Soozin: People always ask, “What even is that degree?” And I say, “It’s basically pre-pharmacy.” It was an amazing, rigorous experience.

William Roger Cummings: At the School of Business, we’re now emphasizing real estate investment. South Florida is becoming known as Wall Street South — and there’s tremendous development happening. Just look at the Waldorf Astoria going up in Miami — 100 stories tall on Biscayne Blvd.

Adi Soozin: I know! And people keep saying the Miami bubble’s going to burst — but it just keeps building.

William Roger Cummings: It does. We’ve got the ocean, the beauty, the climate…

Adi Soozin: Plus, emerging tech and venture capital. Silicon Valley types are moving here — we’re at the start of becoming the next NYC.

William Roger Cummings: Ken Griffin of Citadel, for example, has relocated his firm here. He’s bought four oceanfront lots in Palm Beach, right across from Mar-a-Lago, to build a residence for his mother.

Adi Soozin: That’s incredible. You mentioned this earlier, but I’d love to go deeper. What are you teaching students now who want to enter real estate?

William Roger Cummings: Through the Rinker School of Business, we’re building a real estate program to help students translate their degree paths into career paths. My advice is: use your degree to advance your career, accept promotions, grow — and then, at 5:30 p.m., turn it off. Make time for family, hobbies, and a meaningful life.
Meanwhile, invest passively in appreciating real estate assets. Pay down debt quickly to secure cash flow and long-term value. Keep adding properties in a thoughtful, sustainable way.

Adi Soozin: I love that. Because 15 years ago, college was more about getting a degree just to have one. But now, we’re returning to the core purpose — getting the tools and experience that will actually help you succeed in your career.

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William Roger Cummings: We’re really trying to align the degree path with the career path so that students are not just educated but empowered—using their academic foundation as a springboard toward self-actualization and rewarding careers.

Adi Soozin: We’re segueing a bit here, but what you’re doing is essentially restructuring the degree experience—making it a clear win-win for students pursuing a real estate career at PBA.
You also apply this win-win philosophy in your real estate transactions. Could you elaborate on that mindset? My family has a similar rule: if it’s not a win-win, we walk. There are enough good deals out there that don’t require compromising integrity.

William Roger Cummings: It really starts with getting to know the people you’re working with. I’ve been fortunate to spend my entire career in South Florida. I lived in Coconut Grove for eight years, earned my undergraduate degree at the University of Miami, and then a Master of Laws from their law school.
So, I know the area well—and that helps me guide clients more effectively. I can make suggestions based on real, local knowledge: where to buy, where to live, how to align their investment with their lifestyle. That allows me to match people with properties that not only provide a strong return on investment but also reduce friction in the transaction. That goes a long way.

Adi Soozin: Absolutely. My mom’s a broker, and I can’t tell you how many times she’s said, “You won’t believe what this client is asking me to do.” I always remind her: if they’re asking for more and not bringing anything to the table—especially after you’ve delivered great results in the past—maybe they’re not the right fit. You need to find clients who understand that real estate works best as a collaborative, win-win environment.

William Roger Cummings: That’s why I take a different approach. I’ve heard both sides—buyers who want to pay less than market, and sellers who want to ask more than the property’s worth. I tell them, “Sure, I can represent you. But help me understand your reasoning.”
If someone says, “I just want to pay less,” I explain that’s not a compelling negotiating position. But if we frame a logical, respectful rationale, it creates the possibility for a cooperative outcome—and maybe even future deals. Win-win relationships are built on mutual respect and logic, not shortcuts.

Adi Soozin: Yes, I completely agree. I’ve seen people try to game the system, cutting corners or squeezing others, and within five years, no one will do business with them. Their reputation precedes them, and the bridges they burned are gone for good—all over a few extra dollars.

William Roger Cummings: Exactly. I’m grateful that after decades in this market—from the Keys to Palm Beach—I don’t have to cross the street to avoid anyone. I can sit outside a Starbucks, and when people recognize me, they’ll say, “I worked with him—solid guy.” That kind of reputation is invaluable.

Adi Soozin: It really is. That kind of social equity is rare and incredibly powerful in real estate.
Now, having seen multiple market cycles over your 50+ year career, how have you adapted to those shifts? And what advice would you give to agents navigating today’s challenges?

William Roger Cummings: One of the biggest hurdles for new agents is that success doesn’t come quickly. Real estate is a long-game profession. You have to build relationships—start with your family, friends, your network—and ask for their support.
But this isn’t a job where you get a paycheck next Friday. You need to be able to sustain yourself through long lead times, irregular commissions, and uncertainty. If you have another job or income source while you build your real estate career, that’s completely fine. Just ease into it.
We’ve seen students who think they’re going to immediately broker a $50 million mansion and are already calculating the commission—before they’ve even met the homeowner.

Adi Soozin: This next question isn’t on the list, so feel free to pass, but I’m curious. With your network, knowledge, and experience—why haven’t you launched a real estate fund?

William Roger Cummings: Honestly? Because it’s work. It’s another full-time job. Just like I advise students to pursue real estate investments as a form of passive income, I view fund management as something entirely different.
Some students say, “Well, you could make more doing Airbnb.” Sure, but Airbnb is also another full-time job. So is running a fund. You have to vet investors, qualify your team, manage compliance, and answer to everyone. It’s serious.
I admire those who do it, and I often refer my clients to people running REITs. But for me, I do better by focusing on the work I enjoy—and that’s client relationships, real estate strategy, and teaching.

Adi Soozin: That totally makes sense. Some people look at the work I do for our fund and say, “I could never do that.” But for me, it’s fun. We all have our thing.

William Roger Cummings: Especially in family offices—people rely on you 100%. The stakes are high.

Adi Soozin: Yeah, well, my little sister’s on a two-year vacation in New Zealand, so… it’s me or no one.

William Roger Cummings: [laughs] New Zealand, huh? I’m sure it’s beautiful.

Adi Soozin: She looked at the family pressure, said “I love you,” and peaced out to New Zealand.

William Roger Cummings: [laughs] Well, we all have to play the cards we’re dealt. But truly—finding yourself, defining your own identity—that’s key to a fulfilled life. If you can align your work with who you really are, you’ll be more effective and much happier.

Adi Soozin: I agree 100%. I lived in Europe for five and a half years. Got my MBA. Built a software company that’s now used in 59 countries. Hit the bestseller list with a book. And then my dad said, “I’m retiring in 10 years. You have 10 years to figure out what I’m doing or you’ll miss the chance.”
Honestly, ten years ago, that would’ve felt suffocating. But now, having lived my own path, it’s the natural next step.

William Roger Cummings: Excellent choice. Really.

Adi Soozin: Thank you. And I love how you keep bringing it back to self-actualization. Not enough people prioritize that. Why do you think that is?

William Roger Cummings: I believe that so many problems—health, relationships, even job dissatisfaction—stem from internal stress. And that stress often comes from trying to be someone you’re not.
You end up chasing validation from people you don’t agree with or pursuing a path that doesn’t fit you. That creates emotional tension that wears on your well-being.
I was a lawyer for 15 years. I can still do it today. But I didn’t enjoy the intensity or the office culture. I love being around people, negotiating deals, and building things. That’s what makes me happy—and the income’s not bad either.

Adi Soozin: Same here. Our fund’s co-founder took me two years to find because people who value long-term relationships and win-win deals are rare. I wanted someone who still sleeps well at night. That’s the standard.

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Adi Soozin: What are some philosophy books that you’ve read? I know we’re going off script here—sorry!

William Roger Cummings: I wouldn’t say I read traditional philosophy books. I read people’s stories. I admire individuals—not necessarily because of what they do, but because of how they do it. Their work means something to them, and that inspires me.
Just yesterday, I was talking to a woman I have a great deal of respect for—she’s a librarian. I told her, “I admire you. The programs you bring us, the way you connect with us—it’s truly meaningful.” It’s not something I could do; I’m not academic enough, even though I have a bit of an academic streak. But she brings enrichment to our community every single day.
She’s not an NBA star, she’s not a celebrity—but she’s wonderful. And we cherish her at the King Library at the Society of the Four Arts.

Adi Soozin: Oh, I love the Society of the Four Arts. Their grounds are stunning.
Switching gears a bit—you’ve developed a strong interest in health and wellness. How do your personal wellness practices influence your professional life and overall wellbeing?

William Roger Cummings: Well, making good choices when it comes to health and wellness helps me get out of bed with energy every morning. It lets me enjoy life—go places, do things, stay active.
My motto is #NeverStop. If I hear about something interesting, I want to try it. And if I like it, I want to do it again. But you can’t live that way if you’re weighed down by bad habits.
In my generation, smoking and drinking were common. But around age 21, I realized these things weren’t helping me. If they were already bad for me then, I knew they’d be worse later. And they cost money. So I made the decision to cut them out—and it’s made all the difference.

Adi Soozin: And that’s why you look like you’re 50—even after being in real estate for over 50 years.

William Roger Cummings: (laughs) Well, I recently had a minor surgery and they told me I needed a physical. I didn’t have a primary doctor, so I found one. The doctor asked when my last physical was—I couldn’t remember. Then he asked what medications I take. I said, “None.”
He ran some basic tests and said, “You’re in great shape.” He added, “You scored a 97 on your respiratory.” I said, “Out of 100?” And he said yes. That’s when I knew skipping the cigarettes was the right call.

Adi Soozin: I know you work out too—what’s your routine?

William Roger Cummings: I’ve always belonged to gyms. I enjoy weight training and building stamina. Back when I was in law school in Boston, I heard about the Boston Marathon. At the time, I was lifting weights and thought, “26 miles? That’s impossible.” But 10,000 people were running it that day.
So when I moved back to Florida, I joined the Palm Beach Runners. I trained step-by-step with my girlfriend, and together we ran four marathons in Miami. They were incredible experiences.
I remember our first one: we woke up at 5 a.m., ran 26 miles, got a medal, came home to Palm Beach, cleaned up, and went to a gala at the Science Museum that night—danced for hours.
When you live right and follow the process, it works.

Adi Soozin: That’s amazing! I only ran a half marathon once, in Sydney, Australia. That’s the closest I’ve come.

William Roger Cummings: That’s a long way—great job.

Adi Soozin: Thank you! I tried to run the Paris marathon but tore all three ligaments in my knee during training. I was running with my dog, holding her leash, and she kept spotting chickens—there are wild chickens in northern Italy. One sudden pull and that was it. I didn’t even realize how bad my knee injury was until all three ligaments tore.

William Roger Cummings: That’s awful. I’m really sorry to hear that. Pets are strong—you’ve got to be careful when running with them.

Adi Soozin: So true. I have a Belgian Malinois—about 80 pounds—and I track my fitness with a friend. One day he asked why my heart rate was so high during a short walk. I said, “That wasn’t a walk. That was a power struggle with a canine bodybuilder.”

William Roger Cummings: (laughs) Yes, I know the type. Big, strong, and determined.

Adi Soozin: For people who want to invest with you or be mentored by you, what’s the best way to reach out? Is it LinkedIn?

William Roger Cummings: Yes, LinkedIn is best. They can connect, follow my updates, or send me a direct message. No matter where I am or what time zone I’m in, I can see it and respond when appropriate.
Phone calls are tough—I might be in Europe or with clients. And I don’t like taking calls when I’m spending quality time with people. I think they deserve my full attention.

Adi Soozin: Completely agree. Now, tell me about the two pins you’re wearing.

William Roger Cummings: The first one is from Palm Beach Atlantic University. It’s the same one our president, Dr. Deborah Schwinn, wears. I was honored to receive it. The smaller one is from Mensa.

Adi Soozin: Wait—you’re a Mensa member?

William Roger Cummings: I am. I used to be the LocSec—that’s short for Local Secretary—for the Palm Beach County chapter. Mensa had this quirky tradition of avoiding the term “President” because it sounded too autocratic. So we were called LocSec instead.
We had local proctors who administered IQ tests to those interested in joining. The organization brings together people from all walks of life who fall in the top percentiles on standardized intelligence tests.

Adi Soozin: Are you still active in Mensa?

William Roger Cummings: I am. The members come from such diverse backgrounds that I’m always learning something new. One of my personal role models when I was LocSec was John Hillis, the chief librarian for the City of West Palm Beach.

Adi Soozin: Another librarian you admire!

William Roger Cummings: Yes! He was an exceptional leader—this was back before everything was digital. He used the Dewey Decimal System to manage the entire library and support researchers. As a lawyer, I know how hard research can be. He was also a devoted family man and an all-around wonderful example of intellect and humility.

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Adi Soozin: When I applied to IE Business School, they had an IQ test as part of the admissions process. You had to score above a certain percentile to get in, but the required score varied depending on how many people were applying from your country. Their top priority was ethnic diversification. So, if you were the only applicant from your country, your score didn’t matter as much. But the year I applied, there were so many Americans that, if you were American, you had to score in the top 1% to be accepted.
When I came back to the U.S., someone suggested I join Mensa. But you’re actually the first person I’ve met in real estate who’s also part of Mensa.

William Roger Cummings: Well, I might be the first person you’ve met with my kind of profile. I have great respect for the Mensa organization—its members include authors, lecturers, and people with very high academic accolades.
But I’m a bit different. It’s almost embarrassing to say I’m “not academic,” since I’ve earned four or five advanced degrees. But I pursued those purely out of interest, not necessarily from an academic inclination.
When I was the LocSec—that’s the local secretary—of the Palm Beach County Mensa chapter, the previous LocSec had hosted academic lectures in his home in the historic Addison Mizner district of Boca Raton. It was very aristocratic and intellectual.
When I took over, I added something new: I started organizing group outings to discotheques. And I noticed that some of the members—especially those who were a little shy or socially reserved—had a fantastic time when they got dressed up and hit the dance floor. So did I!

Adi Soozin: That’s so neat. I might look into taking the test. Joining you guys could be fun.

William Roger Cummings: We’d love to have you. A lot of people don’t know how well they might score simply because they’ve never taken the test or never thought about it.
When I finished high school, my grades weren’t great. My father was in the Secret Service, and after my parents divorced in my early teens, I moved between a lot of schools. My guidance counselor actually said I might need to take a fifth year of high school before I’d be eligible for college—until the merit scholarships came in. Once I won a couple, she said, “You’ll be alright.”

Adi Soozin: In high school, I used to calculate what I needed to score on tests and homework to avoid writing papers. I could study for 30 minutes, ace the test, and breeze through the homework. But a 5- to 10-page paper? That could take up every weekend for a month!

William Roger Cummings: That reminds me of my own experience. When I was in the international business and tax master’s program at the University of Miami Law School—a program modeled after NYU’s—I was fortunate to be part of a lecture-based track that didn’t require a thesis.
But midway through my second year, I had a serious motorcycle accident and couldn’t attend classes. The Dean at the time, Rafael Benitez—an incredible man—restructured my path so I could graduate, but I had to write a thesis.
I wasn’t a natural writer. I brought him my draft, and he was kind and diplomatic, but you could tell he knew it needed work. He suggested I collaborate with a classmate who was a strong writer. That classmate didn’t charge much, but he did nearly wear out a blue pencil editing my pages—circling sections, crossing things out.
With his help, and the Dean’s support, I completed it. And now, if you go to the University of Miami Law Library, you’ll find my thesis on the shelf.

Adi Soozin: I made it through most of high school and college avoiding papers—unless it was a topic like Biblical Studies, which was easy. But for subjects like physics? Those papers were brutal. I always calculated how to avoid them.
And then, irony of ironies, I was hired to write a 400-page marketing book.

William Roger Cummings: Yes, and we’ve heard of that book—and its success. You may have started out avoiding writing, but I think you’ve evolved into quite a good writer.

Adi Soozin: I’ll admit the early editions were rough. Thankfully, I had a five-person editorial team reviewing each section. They’d say things like, “Pull this out,” or “Explain this in more detail.”
What I didn’t realize until later is that my brain tends to jump to tertiary effects. I’d say, “If X happens, obviously step 21 is the result.” But most readers were asking, “What happened between step 1 and step 21?”
Writing that book forced me to slow down, dissect each step, and essentially rewire how I communicate ideas. It was like having to rebuild a mental highway to explain every on-ramp and detour along the way.

William Roger Cummings: That’s a perfect analogy. And that’s exactly why your book has helped so many people—because they don’t naturally think that way.
In Mensa, one of the greatest lessons I’ve learned is how differently people approach problems and situations. That diversity of thought is powerful, especially in business and life.

Adi Soozin: That’s so true. I used to assume everyone thought marketing was obviously supposed to grow revenue. But many marketers focus on things like impressions, likes, and comments—as if that’s the end goal.
To me, the purpose of marketing is step 21: revenue. Otherwise, you won’t have a marketing budget next year!
The book is all about using neurobiology to drive that end result. But you’re right—I never thought about how my brain works being related to Mensa until this conversation.

William Roger Cummings: I had a similar revelation when a young woman in our group once looked at me and said, “You must be some kind of linear thinker.”
I asked her what that meant, and she said, “You think A leads to B, leads to C, leads to D. We don’t all think that way.”

Adi Soozin: Yes! And learning to understand people who don’t think that way is a skill in itself. I’m still learning.
Anyway, thank you so much for your time today. Is there anything else you’d like to share with the audience?

William Roger Cummings: Just this: think about what’s truly good for you. Think about what brings you joy, what rewards you, and what enriches your life—and the lives of those around you.
Find that identity. Find that sense of secure self. When you do, it will serve you well—and everyone you love.

Adi Soozin: Beautifully said. Thank you so much. And thank you to everyone who tuned in. I’ll see you online again soon—bye!

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