Matt Gillespie Guiding Dreams

Pittsburgh Real Producers, December 2023

In the world of real estate, success often boils down to a combination of genuine passion, relentless determination, and unwavering commitment to helping clients navigate the complexities of buying or selling a home. Matt Gillespie, the dynamic force behind The Gillespie Team, is a prime example of an agent who personifies these qualities.

With a small but dedicated team consisting of only himself and his licensed assistant, Laura Gans, Matt has carved a niche in Pittsburgh’s real estate scene that’s defined by personal connections, hard work, and a genuine love for his hometown.

Born and raised in Mount Lebanon, Pittsburgh flows through Matt’s veins. He started his journey into the world of business by establishing a moving company called “Make Moves” with his cousin, John. Their decision to venture into the moving industry in their early 20’s was a bold one, opting for hands-on experience instead of a traditional college education. This venture not only honed Matt’s entrepreneurial skills, but also planted the seeds of what would later become a thriving career in real estate.

For as long as Matt can remember he’s been interested in, and loved, real estate. And after dabbling in a few renovation projects, including his first home purchase, a deep passion was fostered. This ultimately culminated in getting his real estate license in 2015.

Known for his high energy and an unquenchable thirst for the chaotic pace of real estate, Matt found himself navigating a transformative moment in 2020 when his business experienced significant growth. In a tough market, he managed to close a remarkable 38 transactions, a testament to his unwavering commitment and the dedication of his clients.

Throughout his journey, Matt has encountered individuals who have made a profound impact on his life and career. One such figure is Linda Carnevali, a respected educator in the field. Matt credits her classes, which he took multiple times, with changing his life in numerous ways. If it wasn’t for his trusted lender and friend, Dave Holland, having invited him to attend her class, who knows how Matt’s journey would have changed.

He’s also benefited from his association with Brian Buffini, who has been a gamechanger for his business. They focus on
client relationships, organization through CRM, and creating advocates for their services. Matt also acknowledges the support and guidance of Anthony Leone, who played a pivotal role in helping him establish his real estate career in 2015.

For Matt, the most fulfilling aspect of his work is the act of helping people. He genuinely enjoys guiding clients through the real estate process, forming connections with them, and witnessing their growth and success. His approach is client-centric, always striving to prioritize their needs first.

In the journey of entrepreneurship, one pivotal moment for Matt was bringing Laura on board. Laura, his licensed assistant, has allowed Matt to focus on what he does best—working closely with his clients. Her unwavering support on the back end has significantly eased the workload and provided more time for personal interactions. Such interactions include the client
appreciation parties they recently implemented and host twice annually. These events not only show their clients how much they value the relationship, but also provide a fun, engaging atmosphere for all to enjoy.

On a daily basis, Matt makes it a point to remind himself and his kids of the importance of recognizing how they are blessed, loved, hardworking, and capable of achieving whatever they set their minds to. Matt’s family includes his wife, Alyson, with whom he has been together since they were 20, and their children, Griffin and Ella Jane. Their beloved 14-year-old dog, Bonita, completes the family picture.

In his free time, Matt indulges in playing Paddle (Platform Tennis) and enjoys spending time outdoors with his family, immersing himself in good reads, and making the most of Pittsburgh’s unique charm. Pittsburgh, he says, offers easy access, a blue-collar vibe, a history of hardworking people, and a family-oriented community. It’s a place where values are wholesome, and the hustle and bustle is grounded in down-to-earth principles.

Matt Gillespie’s journey is a testament to the enduring power of personal connections, hard work, and an unwavering commitment to his clients and community. With unwavering enthusiasm, he’s continuing to build success one home at a time, leaving a trail of satisfied clients and lifelong memories in his wake.



30 Under 35

Pittsburgh Real Producers, June 2023