At sunrise on the James River, Ben Roper cuts across glassy water on a slalom ski. The line is tight. The rhythm is steady. It looks simple from shore. It is not. “It’s not about what you make. It’s about what you keep,” he says. “Success is financial freedom and peace at the same time.” The water is his reset button. The lesson follows him back to work.
Relationships are the real asset
Roper’s career sits at the intersection of real estate, capital markets, and human nature. He is the REIT specialist at Capital Square in Richmond, Virginia. His focus is the Section 721 UPREIT exchange. In plain terms, he convinces owners and developers to contribute properties to a REIT in exchange for operating partnership units. It is a tax-efficient way to move from a single asset into a diversified, income-producing platform. It only works when trust is strong.
“Know people, know how people work and think,” he says. That line explains his approach. He studies incentives. He listens. He maps the fears that stall good deals. Then he makes a path that feels safe and clear.
A family name and a public path
Roper grew up in Richmond in a family that builds. His grandfather served as mayor of Petersburg and ran Roper Lumber. His father, Phil Roper, is a well known apartment developer. In August 2025, Ben was named Chief Investment Officer at his father’s firm, Real Estate Services. The title adds weight, but it also adds context. He is a bridge between two worlds. One foot is in development. The other is in capital formation.
He also spent time in politics and policy. He interned in the Senate. He worked in media relations at The Heritage Foundation. He even published commentary on how special envoys can complicate U.S. foreign policy. The throughline is clear. Remove friction. Clarify roles. Keep the main thing the main thing.
Property management in a crisis
Roper’s first real test came in property management. He started leasing apartments at the American Tobacco Center in Richmond. He moved into special projects. Then 2020 hit. Overnight, occupancy and collections were at risk. Roper helped keep buildings full and teams focused. The effort led to a move into an innovation role in Atlanta, where he pushed new tech and process across a growing portfolio.
Growth brought tension. “Right people, right seats,” he says, looking back on a period when the company doubled in size. He learned how fast hiring and shifting roles can break systems. The lesson pushed him toward the investment side, where clearer incentives and deal structures fit his style.
The 721 play
At Bonaventure, Roper shifted to sourcing apartment deals through 721 exchanges. He met property owners, family offices, and developers who wanted liquidity and diversification without a taxable sale. He helped them swap equity in a single property for units in a larger, managed fund. The move to Capital Square sharpened that focus. The mandate is clear. Grow the REIT through 721 contributions. Be the person who makes a complex trade feel simple and fair.
He frames the conversation in human terms. What will life feel like after the exchange. How will estate planning work. What control will remain. What cash flow can they expect. “People need to see themselves in the structure,” he says. “Then the numbers click.”
When reputation meets revenue
Deals can die for reasons that have nothing to do with NOI or cap rates. Roper learned this the hard way. Two owners walked away after reading a negative online article about him. They called his boss to say so. The lost equity totaled about 53 million dollars. It stung. It also sharpened his view of risk.
“Relationships take years. Search results take seconds,” he says. The experience pushed him to get proactive about public information, to keep focus on work, and to over-communicate with partners. It reinforced the core belief that trust is earned in small moments long before a term sheet lands.
Why people say yes
The best pitch in his toolkit is not a pitch. It is a story. Roper talks about a developer who built a great asset but felt trapped by concentration risk. The 721 exchange gave that owner units tied to a broader portfolio, professional management, and a path to liquidity over time. The developer stayed close to the work but gained freedom from single-asset risk. Simple. Human. True.
He uses the same approach at home. Waterski in the morning. Calls and meetings through the day. He listens more than he speaks. He writes follow-ups that do not waste time. He treats every yes as the start of a longer conversation.
What comes next
As CIO at Real Estate Services, Roper will help guide new projects while he continues to grow Capital Square’s REIT through 721 deals. It sounds like a lot. It is. But the frame stays narrow. Keep the line tight. Stay in rhythm. Protect what you build.
“Success is relationships in the right place,” he says. “Money is a byproduct. Peace is the goal.”
In the end, his work is about trade-offs, timing, and trust. The same rules that keep a skier upright at speed. The same rules that keep a deal moving toward a clean close.
Interview with Ben Roper
What first drew you into real estate?
I grew up around it. My dad is a developer, and my grandfather owned a lumber company and served as mayor of Petersburg. Real estate was always part of our family conversations. After college I started leasing apartments, and that gave me a ground-level view of how properties actually run. From there, it just kept building.
You’ve talked about 721 exchanges being your main focus. Why is that structure so important?
The 721 UPREIT exchange gives property owners something rare: a way to swap their building for shares in a REIT without triggering a taxable event. It helps them diversify and still feel tied to real estate. For me, it’s a conversation about trust. Owners need to know they’re not giving up control, they’re gaining stability and flexibility.
Can you share a moment in your career when things didn’t go as planned?
Absolutely. Early on, I lost two deals worth $53 million in equity because of an old article online. The owners saw it and decided not to move forward. That was tough. But it forced me to think about reputation in a new way. I learned you can’t just manage numbers—you have to manage perception too.
What was it like working through COVID in property management?
It was intense. Occupancies could have fallen fast, but my team in Richmond worked around the clock to keep people in their homes. We had to be creative with communication and flexible with residents. That period taught me how to stay calm and practical when the pressure is highest.
What lessons from outside work have shaped your approach to deals?
Waterskiing, for one. Out on the river, you have to stay balanced and keep a tight line, or you’ll go down fast. Deals are the same. It’s about rhythm, control, and knowing when to adjust. That mindset has been with me from sports to business.
How do you personally define success?
It’s not just about money. It’s financial freedom, yes, but it’s also peace of mind. It means relationships are healthy, morals are steady, and the day-to-day feels balanced. If you can keep your work strong and your personal life centered, you’re already ahead.
