“The Smiley Group (TSG) is a residential real estate team created around the premise that whether someone is buying, selling, or leasing property or land, the experience and service delivered should be tailored to each individual client. Each client and property is unique. Why would any real estate agent or team approach each buying/selling process the same? The service TSG provides is customized to meet each client’s where they are.

Each member of The Smiley Group brings their whole self to what they do. One wouldn’t likely find any of the agents presented as one would expect from ’traditional” real estate agents. That’s just not who we are. The Smiley Group aims to provide professional yet comfortable, relatable, and enjoyable service to its clients. If we are stuffy, the process will be stuffy and that does not make for an enjoyable buying/selling experience. Make no mistake, while we are casual and comfortable, we are serious real estate professionals that serve clients in all demographics and price ranges.
The Smiley Group has built relationships with the industry’s top service providers to ensure that the same high-level service is continued through the entire real estate process and long afterward. The service providers and vendors that we recommend have been extensively vetted. TSG would not make a referral based on any financial benefit to our team. Our goal is to make sure that whether you are working with one of our Advisors, a home inspector, a mortgage lender, or any other of our partners, the level of service you receive should be seamless and consistent.
Our mission is simple…. “A real estate experience that makes you smile!” It may sound cliché, but an enjoyable and stress-free real estate experience is what we strive for each and every day. Contact The Smiley Group for the best partnership on your next real estate adventure!

Octavius “O” Smiley-Humphries

Hailing from Atlanta, Georgia, “O” as he is affectionately called, relocated to North Carolina in 2015. For the first two years in NC, Octavius was a stay-at-home dad. This time taught him two things:

1. Patience…. A whole lot of patience!!!

2. That life is best lived when it is driven by passion.

The ladder idea is the force that prompted Octavius to get back into real estate. You see, O became a licensed real estate agent in Atlanta during the most exciting time in real estate… 2006! If you are too young to remember that time period, that was just about the time the real estate “bubble” was ready to burst. By 2009, Octavius was out of a job in the one profession that he truly loved.

It was not easy returning to real estate, but Octavius found it important to prove to his son that while you may fall and get bumped and bruised, you can always get back up. Now, Octavius is a top producing Realtor® in the Triangle area of Raleigh, NC. Working with clients is not enough for this avid UGA Bulldogs fan, lover of food, and self-proclaimed shopaholic. Octavius serves as the Vice President of the greater Triangle chapter of NAGLREP (National Association of Gay and Lesbian Real Estate Professionals), as a board member of The United Way of Chatham County, and as a parent rep for his son’s school’s PTSA.

“My goal is to partner with each and every person I have the opportunity to represent. Each client is unique, and each transaction is unique. That is why I provide an authentic and tailored experience for my clients!”

John Tassa

If there is one thing John knows for certain in this world it’s that change happens…whether we are ready or not. As a child, he lived in six different states from New Jersey to Texas before he was even a teenager (Papa was a rolling stone). He then moved four more times as an adult. Once for school, once for work and a couple of times just for the fun of it! After an incredible run in Colorado, John and his wife decided to make one last big move. To put down roots in North Carolina and start a family together. Along with their cat, 2 dogs and a bearded dragon named Biscuit, they loaded up their cars and hit the road. It wasn’t long before they found their niche in the Bull City and have been proud to call Durham “home” ever since.

John’s path to Real Estate (much like his path to North Carolina) has provided him with some amazing life experiences. His professional life began in the restaurant business as a server, cook and eventually Chef. After fifteen years of culinary adventures, he decided to step out of food service to be a stay at home parent to his son and a foster parent to some truly amazing kiddos. All of these experiences have taught him the value of trust, reliability, service, and the importance of supporting the communities in which we live. In addition to helping people navigate the wide world of real estate, he delivers fresh food for individuals with mobility challenges through Mobile Market, helps organize a yearly Christmas Market for families in need, and serves as Vice-Chair on the Board of Directors for the Duke Memorial Weekday School. Oh, and he also likes to pretend he knows how to play the guitar.

Life is full of changes and we all need a little help on our journey from time to time. Change can be nerve-wracking, but John knows from experience that with the right people around you it can be rewarding, memorable, and a whole lot of fun!

Kevin McIntyre

Kevin loves living in North Carolina! Growing up in Morgantown, WV, then moving onto Ohio, Virginia, and Pennsylvania has given him the perspective to see what amazing opportunities are offered in this great state: the mountains, the beaches, the peaceful farms, and the busy city nightlife. Kevin cherishes the opportunity to live and work in such a diverse state.

Kevin’s favorite thing about North Carolina is the beautiful range of year-round weather and the beauty it has to offer- the colorful leaves hanging around throughout the fall, the mild winters and the sun glinting off the ocean waves in the summer. Kevin has lived throughout the Triangle, and vacations frequently in the Outer Banks and the Wilmington area. He loves seeing properties from all eras and designs but has a special interest for modernist architecture.

Now that Kevin has cemented his roots in the Triangle area of Raleigh, NC, he has jumped in headfirst as a contributor to his local personal communities. It should come as no surprise because service is at the heart of who Kevin is as a person. Kevin’s involvement with the Crape Myrtle Festival, the National Association of Gay and Lesbian Real Estate Professionals (NAGLREP), and the Realtor Foundation of Wake County fuel his commitment to giving more of himself to the people and communities around him.

Kevin brings abundant energy, creativity, and dedication to his work. He takes time to listen and learn about his clients’ needs, wants and desires to match them to the right property and create a positive experience. From the first call, all the way through closing, Kevin promises to bring integrity, energy, hard work, and passion to our relationship.

“Whether relocating from across the country or just across town, I am ready to help you find a place that you can call home.”

Robby Nash

Robby Nash

Robby joined The Smiley Group in January of 2020 after settling in North Carolina in 2019, but it was a winding road to get here.  Originally from the beautiful Shenandoah Valley in Virginia, Robby moved to Blacksburg to study at Virginia Tech for 4 years.  He eventually received a master’s degree in education from Radford University and taught high school math at Blacksburg High for 4 years, a challenging and rewarding opportunity.  Channeling his inner Michael Greller (professional golfer Jordan Spieth’s caddy who also use to teach math), he then moved west to sunny California where he became a full-time golf caddy helping golfers navigate the challenges of the course for 4 years at Bighorn Golf Club.  


Now a licensed real estate professional, Robby desires to help buyers through the often unknown process of purchasing a home.  He loves working with and educating first-time home buyers and making sure they are well represented in an ever-changing market.  He also has a passion for linking his dad’s business as a contractor and home builder with his real estate business through new home construction and equitable rehabilitation.  


Leaving no stone unturned, no attic un-attended, and no crawlspace un-crawled, Robby is here to help “caddy” you through all of your real estate needs.

The Smiley Group