Leveraging Family Legacy in Real Estate Entrepreneurship

Real estate has always been more than just a profession for me—it's been woven into the fabric of my family for generations. As a fourth-generation real estate developer, the lessons I learned growing up around dinner tables discussing cap rates, property management, and investment strategies laid the groundwork for my career in real estate finance and entrepreneurship. During my recent appearance on the RIS podcast, I shared how generational knowledge and legacy can uniquely position family offices and high-net-worth families to achieve long-term success in real estate investing.

Turning Family Dinner Conversations into Wealth Creation

Growing up in a real estate family meant business conversations often happened casually over meals. I vividly recall one instance as a child, riding in the car and seeing three gas stations on the same intersection. My immediate instinct—something my parents noticed and often joked about later—was that one of these businesses wouldn't survive due to oversupply. That early grasp of supply and demand, cultivated informally but consistently, became a foundational insight in my career.

Family offices and high-net-worth families can leverage similar opportunities by intentionally fostering regular discussions around strategic investments, market conditions, and business operations. It doesn't require formal training sessions, just a commitment to openly sharing business perspectives, investment decisions, and lessons learned. These everyday conversations can shape the next generation’s understanding and approach to wealth creation.

Balancing Legacy and Innovation in Family Offices

A common challenge for family offices and high-net-worth investors is balancing respect for legacy with the necessity of innovation. My grandfather’s legacy, honored in our firm's name, Stonehan (a combination of my grandpa’s surname, Stone, and mine, Bohan), reminds me daily of this responsibility. But equally important is our continual pursuit of innovation.

In practice, blending legacy with innovation means honoring foundational principles—such as integrity, stewardship, and prudent risk management—while also adopting new strategies and technologies to enhance returns. For instance, our focus on boutique hospitality investments and innovative multifamily rental models, like rent-by-the-room, reflect how modern insights can strengthen and amplify a family’s legacy rather than contradicting it.

The lesson here is clear: Family offices that strategically balance legacy with continuous improvement and innovation are uniquely positioned for long-term success, stability, and growth.

Strategic Insights from a Fourth-Generation Developer

Drawing from generations of collective experience offers a unique strategic advantage. Over my career, starting as a CPA with Rothstein Kass (later acquired by KPMG) and eventually founding Stonehan Accountancy, I learned to leverage both institutional expertise and entrepreneurial creativity. This blend provides a competitive advantage—especially for families managing significant real estate holdings.

Strategic insights I frequently share with family office clients include:

• Tax-Efficient Legacy Strategies: Real estate remains one of the most powerful tools for generational wealth preservation due to favorable capital gains treatments, depreciation benefits, and sophisticated tax-deferral strategies such as the 1031 exchange.

• Regulatory Clarity and Risk Management: Understanding zoning laws, local regulations, and compliance requirements is crucial, especially for investments intended to last across generations. Boutique hotels versus short-term rentals like Airbnb, for example, provide clarity and sustainability in increasingly regulated markets.

• Technological Leverage: Using modern tools such as AI-driven revenue management software allows even legacy investments to remain highly competitive and operationally efficient.

Putting Family Legacy to Work in Your Investments

Family offices and high-net-worth families are in a unique position: you can harness deep generational knowledge while remaining flexible and innovative in strategy and execution. Leveraging your legacy doesn't mean staying locked in past practices—it means thoughtfully applying enduring values in new ways that enhance your investments and protect wealth for generations to come.

At Stonehan, I work directly with family offices and investors to ensure their strategies balance tradition and innovation, building resilient portfolios capable of weathering market volatility and regulatory shifts.

If you're looking to turn generational wisdom into strategic real estate investments, our team is ready to guide you toward long-term success.