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“5 Things I Wish Someone Told Me Before I Became CEO of Maplewood Senior Living & Inspīr”, With Gregory D. Smith

…Being an entrepreneur, I knew the importance of clear vision, but I don’t think I fully understood that quick thinking and dynamic action wasn’t always a good thing. Knowing where I wanted to go and taking the time to work with my team to get there has allowed me to stay true to our mission… […]

…Being an entrepreneur, I knew the importance of clear vision, but I don’t think I fully understood that quick thinking and dynamic action wasn’t always a good thing. Knowing where I wanted to go and taking the time to work with my team to get there has allowed me to stay true to our mission…


I had the pleasure to interview Gregory Smith, president and CEO of Maplewood Senior Living and Inspīr, an urban international luxury brand. Gregory has a career spanning nearly 25 years and has led the development of a myriad of properties in residential and commercial real estate, hospitality, healthcare, and senior living industries with a collective value exceeding $1 billion. In 2005, Mr. Smith founded the Maplewood brand, which consists of luxury senior living residences throughout Connecticut, Massachusetts and Ohio, with future expansion into New Jersey and other parts of the country. As president and CEO, Mr. Smith overseas the development, construction, finance, and management of the Maplewood brand including Maplewood Senior Living communities and the latest addition to the Maplewood portfolio, Inspir, an international luxury brand of urban senior living residences. In 2017, Mr. Smith embarked on creating a new concept in senior living and announced the new Inspīr brand, which is the convergence of luxury residences, unparalleled hospitality, and world-class healthcare offered to seniors in urban markets. The first Inspīr property, Inspīr Carnegie Hill is set to open in 2019. Mr. Smith also serves as Chairman of the Board of Directors for Ability Beyond, a not-for- profit organization providing residential, employment and day programs to over 3,000 people with disabilities in Connecticut and New York. Mr. Smith is also proud to sit on the board of directors of the Alzheimer’s Association New York City chapter. He is a board member of the Western Connecticut Health Network Development Fund, Inc, and a member of the Network’s Planning Committee, which is tasked with strategic planning for its network. Mr. Smith resides with his wife and children in New Canaan, Connecticut, where he remains active with civic and community based organizations. Mr. Smith has had a lifelong commitment to wellness and fitness. He has incorporated his passion for healthy living into the Maplewood brand.


Thank you so much for joining us! Can you tell us the story about what brought you to this specific career path?

Mycareer started working in New York City’s finance industry. About seven years into my career, my brother — who had been in real estate — decided to buy his first office building and asked if I wanted to partner with him. This first investment led me to a career in real estate. As I expanded my portfolio beyond the first property, I acquired investments ranging from office buildings to full-service hotels throughout the country. There was one specific property I came across in 2004 that ignited a new passion and steered my career in a new direction.

The property was in Danbury, CT, not too far from where I lived with my family. I decided to purchase the property and expand my portfolio to include senior living residences. I was aware there soon would be a need for more senior housing. Baby boomers were about to hit retirement age, and predictions of longer life expectancy and a population shift made this new market very attractive to me. However, this was not strictly a professional decision, and I had personal reasons for the purchase. With beloved family members aging and in need of more care, I wanted to create a place that would meet the expectations of my family, and at the time, there wasn’t anything available.

As my vision for the residence came to life, my mother realized it would be a great option for my grandmother and great aunt. I knew I was creating something that would satisfy the needs of my family as well as the others who were facing similar challenges. That piece of property became my very first senior living community, Maplewood at Danbury, and my grandmother and great aunt were two of the first residents to move in. Soon after, I had other family members become residents.

Today, Maplewood Senior Living operates 15 properties around the country, with five more in the pipeline. This winter, we will debut, Inspīr Carnegie Hill, our first luxury, urban senior living residence under our Inspīr brand.

Can you share one of the major challenges you encountered when first leading the company? What lesson did you learn from that?

My hospitality background and experience managing real estate prepared me for my entree into the senior living space, but there were aspects of the business that were less familiar. The biggest hurdle for me was to understand the care component of senior living better. I knew how to deliver world-class hospitality, but I wasn’t involved with care delivery before Maplewood. To ensure residents received quality care, I brought in a third-party management company and committed to learning as much as I possibly could about that side of the business. I thoughtfully took the time to understand care delivery, what is needed, and how it impacts the lives of our residents, their families, and our staff. Moreover, I found ways to improve on existing models to elevate the care Maplewood residents received, and in doing so, I raised the standard for the industry.

Since I had family members living in the first community in Danbury, I had a unique perspective of seeing both the business side and the point of view of the family. This perspective led me to continually seek opportunities to improve upon how we deliver care and support families during a challenging time in their lives. The lesson I learned through this dual perspective was how important empathy is in leadership and how necessary it is to put yourself into the shoes of your customers. We understand how everything we do affects every resident’s life. It is what helped us develop a reputation for delivering the exceptional care that Maplewood is well known for.

What are some of the factors that you believe led to your eventual success?

I firmly believe that true success stems from teamwork and collaboration. Early on, I surrounded myself with colleagues that shared my passion and were exceptionally talented in their respective disciplines. By communicating my vision, listening and learning from my team, and encouraging new perspectives and ideas to be shared openly, I was able to create a truly collaborative environment. This approach led to our initial success and continues to drive the business forward. When you have talented people who feel valued, have pride of ownership, and know their voices are heard, you can accomplish great things. This is part of our organization’s DNA and I am extremely proud of that.

What are your “5 Things I Wish Someone Told Me Before I Became CEO”?

Recognize the level of commitment needed to be a CEO

Being a CEO requires an enormous commitment and it is not a role for everyone. Some entrepreneurs start businesses thinking that they will work less and rarely is that the case. A CEO is involved in every aspect of the business and it requires your full commitment to the success of the organization as well as a good portion of your time. From the operations to the development, to the marketing and sales, and the programming, I have my fingerprint on all of it. It is a big responsibility and a tremendous undertaking.

Understand the business you are starting

If you are going to run a successful company, you must understand the industry, and this might require additional learning. When I started Maplewood Senior Living, I had a solid understanding of the real estate market and the hospitality industry, but I knew there was more I needed learn about senior living. It was crucial that I educate myself about the inner workings of the industry so I could deliver an exceptional product that surpassed anything on the market. Once I understood the business, I was able to grow and expand into new locations. Investing my time to learn about senior housing enabled me to push my vision forward and scale-up.

Trust people and collaborate

In the beginning, I had to have my arms around everything. The project was my vision and I believed the more I did on my own, the greater the chance for that vision to come to fruition. Luckily, I learned quickly the value of collaboration and began to see how input from others made a difference in the organization. I recognized I needed people with different skills to have a seat at the table for the business to be successful. I learned to trust in their expertise to help me realize my vision for the company. It was through collaboration and trust that Maplewood Senior Living has grown into an industry leader.

Learn to prioritize your time…and be patient

Being an entrepreneur, I knew the importance of clear vision, but I don’t think I fully understood that quick thinking and dynamic action wasn’t always a good thing. Knowing where I wanted to go and taking the time to work with my team to get there has allowed me to stay true to our mission and create two best-in-class senior living brands.

Work-life balance is critical

As a CEO managing work/life balance is difficult. Getting advice on maintaining that balance from a CEO or a person in a position that required this level of commitment, time, resources, and capital, is a conversation I wish I had.

What advice would you give to your colleagues to help them to thrive and not “burn out”?

Have a passion for your work and the success will come. I became involved in senior living to provide a better option than what was available at that time. I had aging loved ones and what I saw in the industry didn’t meet my standards and weren’t places I wanted my family to live. I knew there could be a better way that offered a vibrant, more meaningful lifestyle and provided best-in-class care. Knowing that I can make a difference and create opportunities to improve the lives of our elders is what continues to drive me.

Beyond having passion for your work, it is also extremely important to recognize the need for self-care. My advice to my colleagues is to take care of your physical health and know when you need to step away to rejuvenate and reset. For me, spending time with family, exercising, eating well and traveling gives me the recharge I need.

None of us are able to achieve success without some help along the way. Is there a particular person who you are grateful towards who helped get you to where you are? Can you share a story?

My partners Shane Herlet and Tom Gaston played a critical role in the success of the business through the years. I am grateful for the knowledge and insight they imparted that enabled us to push the mission of the company forward. We all share the same vision, and they have helped tremendously advance our organization to where we are today. More importantly, I am truly grateful for their friendship and continuous support.

What are some of the goals you still have and are working to accomplish, both personally and professionally?

My personal and professional goals intersect. I am passionate about my work; it is a part of who I am. I consistently set new goals and always push the envelope to evolve the company even further. That evolution never stops. I would like to take what we’ve created with both Maplewood Senior Living and Inspīr brands and bring the luxury senior living concept to suburban areas across the country and other gateway cities globally. I don’t ever want to be complacent or static. Maplewood Senior Living has become a leader in the industry because we are always considering new approaches that will make life easier and more purposeful for our residents. Ultimately, I want us to make noticeable differences and change the old paradigms for aging. I want Maplewood Senior Living and Inspīr to raise the bar for what is expected in senior living.

What do you hope to leave as your lasting legacy?

I hope my mark on the industry is that Maplewood Senior Living and Inspīr helped change the expectation of what aging and retirement look like. I believe we have already begun to do that through the exceptional services and care we provide. With a philosophy that embraces enhanced wellness and immersive experiences, we are elevating expectations right now. Our communities combine luxury accommodations, exceptional hospitality, cutting-edge technology, innovative wellness programs, and world-class care all under one roof. My hope is that my vision for transforming the senior living model continues beyond my years. It would be incredible to know I played a small role in changing senior living and providing a new paradigm that allows society to look forward to their elder years.

You are a person of great influence. If you could start a movement that would enhance people’s lives in some way, what would it be? You never know what your idea can trigger!

I want to collaborate with other leaders in the industry to develop programs and initiatives to better support caregivers. Providing care is tough and emotionally taxing on individuals. Burnout is a very real problem in the industry as they work tirelessly and rarely have the support or resources they need. It is our responsibility as leaders in the industry to develop more programs designed to support the caregiver. Regardless if they are staying at a community or if they are providing care in their own homes. As more of the population ages beyond retirement and the need for caregivers increases, we will need to find new ways to ensure they have the help and support they need.

How can our readers follow you on social media?

@MaplewoodSeniorLiving

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