Interviews
Ryan Castle: Adaptability and Foresight
October 25, 2024
By Arianna Marino
The Cape Cod & Islands Association of REALTORS® (CCIAOR) and Cape Cod & Islands Association MLS (CCIMLS) services over 2,800 members across Cape Cod, Nantucket, and Martha’s Vineyard. As the CEO, Ryan Castle has become a prominent name in the real estate industry since assuming his role in 2014. With a background that spans government affairs, journalism, and association management, Castle's journey is one of adaptability and strategic foresight. His leadership has been pivotal in re-engineering the culture of CCIAOR, CCIMLS, and the Martha’s Vineyard MLS (MVMLS), which he has led since its incorporation in 2018. Under his guidance, these organizations have not only embraced new technologies but have also reshaped their value proposition to better serve their members and the community.
Castle’s early career as a communication advisor to the Governor of South Carolina and as an award-winning newspaper editor provided him with a unique skill set that has proven invaluable in his current role. Castle also holds the designation of REALTOR® Certified Executive (RCE), is a graduate of the Institute of Organizational Management by the U.S. Chamber of Commerce, and is certified REALTOR® Professional Standards Administrator. In the following conversation, Castle highlights how his ability to quickly grasp complex issues and communicate them effectively has enabled him to lead with clarity and vision. Join us as we delve into his journey to CEO, discuss the evolving challenges within the MLS industry, and explore his vision for the future of real estate.
Background and Career Journey
How did you get involved with the MLS and PropTech industry?
I came to the Association of REALTORS® world through politics. I was a speechwriter for a South Carolina governor and got hired at 25 to be the Government Affairs Director for a local association of REALTORS® in my hometown of Charleston, SC. From there, and through that experience, I moved up to a chief executive officer position at my current association - serving Cape Cod, Martha's Vineyard, and Nantucket. I had to quickly immerse myself in the world of MLS to understand that as a new, young executive, I had little experience and knowledge of the world - yet, we owned and operated one. That was now ten years ago.
What inspired you to pursue a career in this industry?
I met some alumni of my alma mater through my fraternity who were lobbyists for the State Association of REALTORS®, and we talked about the issues they pursued and why. Those key issues of protecting private property rights, pushing economic development initiatives, and homeownership opportunities resonated with me from a political beliefs perspective, so I always had in my mind to work for the REALTORS®. When I fell in love with local government at a young age, the only pro-business groups with government affairs professionals at the regional level were the REALTORS® and the Chamber, so it had to be one of those two groups, and the REALTORS® were hiring.
How have your previous experiences shaped your approach to your current role?
I prepared to be a journalist for all of high school and college. I wrote news stories, was editor of both my high school and college newspapers, interned for newspapers, and even my first real job out of college was as a news reporter and then an editor of a small town newspaper. This skill set allows me to understand how things work quickly, figure out what we are talking about, and then convey that to an audience - and move from one topic to another quickly. In my role as the CEO of both an association and MLS, you need those skills as one minute you are in a conversation about technology or data, and the next, we are discussing an education class, then the company's business operations, and so on.
Who in the industry, past or present, do you admire the most and why?
Several I have previously worked with. Will Riley, CEO at Charleston Trident Association of REALTORS®, has taught me so much about managing people. His kindness, empathy, and way of managing people put everyone at ease. He knows how to lay out strategic planning in a significant way. Joseph Cullom, CEO of CHS Regional MLS in Charleston, has taught me what I know about MLS. He is a great MLS mind because he is not obsessed with the newest shiny toy or goes outside the MLS wheelhouse, but focuses on working on the main value proposition of the MLS.
Industry Insights
What do you think are the biggest challenges facing the MLS industry today?
The biggest challenge is having enough qualified people to serve in leadership roles nationwide. With more than 500 MLSs and probably the average board of directors having at least ten members, we're talking 5,000 real estate professionals who sit on boards of directors around the country. Not many people think about the purpose and value of MLS at that level when sitting in these rooms. This is not discussed around MLS consolidation, but it needs to be. Most brokers and agents are trying to earn a living - and rightfully so - and are not concerning themselves with the issue of data integrity, data movement, and cooperation principles and policies, so they have not thought deeply about these issues to be able to sit on a board and advise on them.
In your opinion, what is the most underrated tool or technology in real estate right now?
The cell phone, without a doubt. Think about how it has made real estate more efficient and effective, yet no one considers it, and many MLSs still need to realize the investment that needs to be made in the mobile world. Luckily, I haven't even had to consider that as we use FlexMLS by FBS, and they have had a first-class app for over a decade, and it's just become something my members expect. But I am amazed when I think about other MLSs still trying to figure out a great user experience on the smartphone or buying external products to have a mobile experience. I don't know why the industry has let this happen.
How do you see technology transforming the real estate market in the next five years?
It will all be about how to be more efficient, which will allow the agents who can be productive to be more productive. This will continue to allow those who can do systems and processes to focus on real estate aspects and get more clients. Whether it's AI, the integration of data, or more flexible technologies, it is all about being more efficient and productive for the agent and broker.
What's your prediction for the next big disruption in MLS or real estate technology?
There is a massive disconnect between where the industry is headed and where the everyday practitioner wants it to head. No one is connecting the dots for the practitioner. We need to make a more forceful case about how the changes to the MLS right now are benefitting the everyday practitioner because, without that, the next significant disruption will be that MLSs will be broken apart back into smaller silos again.
What is your vision for the future of MLS and PropTech?
We have to move the MLS away from being a listing-centric database to a property-centric database. Realizing most MLS systems were simply the book on a computer screen; we have to evolve and think about what the MLS would be and look like if we created it today. I would start with property data, then overlay listing data and other data to create a full property record. Then I would ask agents where they go for information about properties not in the MLS and then input that data in the MLS. Additionally, we need to double down on cooperation. Compensation may have gone away from MLS, but the duty to cooperate has not. I think we need to double down on policies, especially technology, to create more cooperation.
Leadership and Management
How do you approach decision-making and strategy as CEO?
My role as the chief executive is to think three to five years ahead of my members. I want my senior staff and volunteer leadership to be eighteen months to three years ahead of my membership. Then, the rest of my staff and board think six months to a year ahead of the members. This way, we are staying ahead. There are ideas and initiatives I conceived three to five years ago, but I am just getting off the drawing board now because the need is becoming more apparent. You cannot wait until your members come to you and say ‘this is a problem.’
What is your leadership style, and how has it evolved?
Having children (mine are six and five) has taught me to have more patience, which comes through in my leadership style. I was very impatient and wanted everything done yesterday, but through raising children, my patience is getting better (although my wife would still say it needs much more work!).
Ultimately, my leadership style is to hire staff that I trust and then trust them to do their job. If they are not doing their job, it will show in projects or initiatives, or even daily tasks will not get done. I will know.
What do you believe is key to maintaining a productive and happy team?
When I discover it, I will let you know. There is no key because you have to adapt your leadership style to your team, so it's about recognizing what those are and adapting your style to it. However, I am a big believer that generalists rule the world. For every team member I have, I either designed the job they do or they do something different than they were hired for because, over time, we redefine the job to their strengths and interests. You need to be flexible and realize that people evolve.
Wisdom & Advice
How do you stay informed and ahead in this rapidly evolving sector?
Read MLS PropTech Digest, of course! You need to read a lot and talk to people. Pick up the phone, call folks, and ask what's on their minds. I talk to my large brokers almost weekly, as well as those around the industry. Remember, this is a relationship business, so talk to people.
What advice do you have for emerging leaders in the industry?
While giving respect to those who came before, you need to realize that we give a lot of deference to those influenced by people still looking through a lens thinking it's 2004. As such, always ask the ‘why’ on the given things in the industry. Many will say ‘this is how we do it,’ and should instead ask ‘why do we do it that way.’ If they can't articulate the reason, then it may be time to rethink it.
How do you balance work and personal life in such a demanding industry?
You have to carve out time for yourself and your family. That conference may not be that important. That meeting could happen without you. The new world of work where you are not tethered to an office helps, and it gives you more hours back in a day. But it's essential to have plans and keep a schedule. I was not good at being tethered to a schedule, but over time, I have learned that we have to plan six months to a year out or even longer in order to carve out that needed time with family and pursue my hobbies and interests.
What advice would you give your younger self?
Don't waste the time you have. I always tell my younger staff to take advantage of their time. In college, you think you have no time, but then you get your first job and think you have no time. But then you get married and have kids. When you are younger, you need to learn time management because you have all the time to do more things.
Personal Insights
If you weren't working in MLS and PropTech, what would you be doing?
I would be doing a mixture of political consulting and government affairs work. I love political campaigns as they satisfy my need for competition and strategy. Additionally, I love getting into the weeds of policy, figuring out how to fix things through proposed laws, and being creative to find solutions.
Do you wish to share anything about your family?
I have a 6-year-old and a 5-year-old that keeps u busy. They love the water and swimming. They love being active and doing as many 'ninja' courses as possible. My wife is my rock. She has a great sense of humor. She has been a nurse for several years and at home, she takes great care of the kids. Her job has always kept my life and career in perspective, as nothing that happens to me in a day is as bad as the stuff she dealt with as a nurse at a hospital. Also, as frustrating as it is at times, she is one of the few who has been consistently able to call me on my BS.
What do you do to unwind or relax after a busy week?
I go to dinner with my wife (and possibly friends) and leave the kids with a babysitter. Living in the Charleston area, there is no shortage of great restaurants, so we have a date night or a friend's group dinner several times a month to ensure we're taking the time to be together and relax. Then, coming home to a house of sleeping kids is always nice to relax and unwind with each other, catching up on shows.
What is your favorite quote?
“Life is not fair, so make it fair for yourself.” - Ryan Castle
Where is your favorite vacation spot?
Anguilla. My wife and in-laws kept talking about it, but nothing prepares you for when you go. There are a bunch of beach bars with beach chairs, where you just sit at the beach with a bar serving cold beer and food they are cooking on a grill. It's such a relaxing experience.