Future Leader: Cal Masterson, Director, Originations, NewPoint Real Estate Capital

Cal Masterson, Director, Originations at NewPoint Real Estate Capital, has been named a 2025 Future Leader by Senior Housing News.

To become a Future Leader, an individual is nominated by their peers. The candidate must be a high-performing employee who is 40 years of age or younger, a passionate worker who knows how to put vision into action, and an advocate for older adults and the committed professionals who ensure their well-being.

Masterson sat down with Senior Housing News to share what drew him to the senior housing & senior living industry, the biggest leadership lessons he has learned, his thoughts on the future of senior housing & senior living, and much more. To learn more about the Future Leaders Awards program, visit https://futureleaders.wtwhmedia.com/.

SHN: What drew you to the senior housing & senior living industry?

Masterson: I’ve always been passionate about mental and physical wellness, especially as these concepts become increasingly integrated into the broader healthcare landscape. The idea of health span — not just living longer but living well — has shaped both my professional perspective and personal outlook. This mindset first developed during my pre-med coursework in college and was reinforced by my experience working in an emergency room, where I saw the value of proactive, holistic care firsthand.

I was drawn to the senior living industry because it allows the opportunity to apply this philosophy on a larger scale, especially from the financial and operational side, where thoughtful capital investment and strategy can create meaningful impact.

SHN: What’s your biggest leadership lesson learned since starting to serve this industry?

Masterson: The most valuable leadership lesson I’ve learned is the importance of resourcefulness, the ability to adapt, problem-solve, and find creative solutions even when resources are limited.

Senior living is a dynamic industry, and we often face challenges that don’t come with a clear playbook such as staffing shortages, regulatory changes, and economic pressures. Resourcefulness means staying calm under pressure, thinking strategically, and rallying the team to find opportunities within constraints. It’s about turning obstacles into innovation and asking, “How can we make the most of what we have?”

This mindset has not only helped us execute tough transactions but also strengthened relationships across the industry.

SHN: If you could change one thing with an eye toward the future of the senior housing & senior living industry, what would it be?

Masterson: If I could change one thing, it would be to accelerate innovation in how technology is integrated with value-based care, not just as a tool for operational efficiency, but as a bridge for connection and personalization.

I envision a future where data, artificial intelligence (AI), and smart systems proactively support residents’ independence, well-being, and social engagement, while also easing the burden on frontline caregivers. By embracing innovation, we can help redefine aging in a way that is more human, dignified, and empowering.

SHN: In one word, how would you describe the future of senior housing & senior living?

Masterson: Integrated.

In the future, integrated senior living environments will combine healthcare, lifestyle, technology, and community into a seamless experience. Rather than treating healthcare, housing, and social life as separate entities, integrated care models will bring them together, creating ecosystems where residents can comfortably age in place with all their needs met holistically.

SHN: If you had a crystal ball, what do you think will impact the senior housing & senior living industry now and into 2026?

Masterson: A key trend shaping the future of senior housing is the influx of new capital from institutional investors and private equity firms.

As the sector continues to demonstrate long-term resilience and demographic-driven growth potential, it’s attracting capital partners who have traditionally focused on more conventional real estate asset classes. These new entrants bring not only capital, but also heightened expectations around operational efficiency, scalability, data transparency, and return on investment.

This shift is likely to accelerate industry consolidation, favor operators with strong brand differentiation and proven outcomes, and drive the adoption of tech-enabled management practices.

SHN: In your opinion, what qualities must all Future Leaders possess?

Masterson: Intellectual curiosity is essential for any future leader in senior living. This industry is evolving rapidly, from advancements in healthcare technology to shifting economic landscapes, and leaders must be eager to learn, challenge assumptions, and explore new possibilities.

Curiosity drives innovation, encourages continuous improvement, and helps leaders stay ahead of emerging trends. Just as importantly, future leaders must be empathetic, adaptable, and collaborative. But it all starts with a growth mindset and a genuine commitment to understanding the “why” behind the work we do.

SHN: If you could give advice to yourself looking back to your first day in the senior housing & senior living industry, what would it be and why?

Masterson: I would tell myself, “Be a sponge. Absorb everything you can, and don’t be afraid to ask questions.”

There is so much knowledge and wisdom in this industry, especially among seasoned leaders and who have seen it evolve firsthand. Early on, I learned that the fastest way to grow is to stay curious and seek out conversations — whether it’s getting coffee with an owner-operator or reaching out to mentors, every interaction is a chance to learn something new. The more questions you ask and the more perspectives you gather, the better equipped you are to lead.

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