Inspired by my colleagues, I took a leap and launched a dual career—a bold move that changed everything.

 

What has brought me joy is creating joyful experiences for others, which I’ve done largely through education. This passion began when I was a kid, loving sports. My dad was a gym teacher and coach, and I wanted to be just like him. After studying exercise and physiology in college, I was hired as a coach and physical education teacher at an elementary school. I coached baseball, girls’ volleyball, and boys’ basketball.

 

Coaching was a blast, but it also overlapped with another passion of mine: real estate. A colleague of mine, who taught and worked as a REALTOR®, introduced me to the world of property. I felt an instant connection to real estate, so I got my license in 2005. At that point, I decided to slowly transition out of coaching so I could balance a dual career as a REALTOR® and physical education teacher.

 

At this time, I was fortunate to work with an assistant coach who was a REALTOR® and became my mentor. We made a team and I learned through hands-on experience. It was hard work, but the challenge made me more determined to succeed.

 

Life took an exciting turn when, one night, my friend and I went to a Brazilian restaurant, and there she was—Gabby, our bartender for the evening. She’s from Brazil, and after we bonded over a caipirinha, I knew I wanted to see her again. We began dating, and over time we got married—it’s been 20 years now—and we welcomed our daughter, Isabella.

 

Through it all, I continued my dual career. I didn’t want to jump full-time as a REALTOR® yet since I loved teaching. I enjoyed organizing games for the kids and watching them have fun. What has kept me going throughout the years is watching their excitement as they play. Through physical activity, they realize they can accomplish things and learn from their mistakes. 

 

I kept my dual career for many years, and although life was stable, a life-changing event struck when my younger sister was diagnosed with stage 4 breast cancer. We were all shocked and left in a haze, especially since she was only 33. It was during this time that the Mama Mare Breast Cancer Foundation reached out to us. They became like family, helping my sister by covering her bills and even sending her on her honeymoon. After 4 years of battling cancer, my sister passed away. Losing her left me grappling with grief and an understanding of life’s fragility.

 

My family and I have become very involved with the Mama Mare Breast Cancer Foundation. I run fundraising events at my school, and my family alone has contributed around 150K to help the foundation continue supporting women battling breast cancer. Besides fundraising, my free time is spent playing golf, hosting barbecues with friends and family, or traveling the world with Isabella and Gabby. And, of course, my 2 French bulldogs, Oscar and Ollie, are like my children—they bring me endless joy.

 

My students are also dear to me. I still teach physical education—I've been doing it for 24 years now—and I’m getting ready for retirement from that chapter of my life. As I    transition out of teaching, my involvement in real estate has only grown. I remain determined to serve my clients at the highest level.

 

Looking back, I feel fortunate to have had careers where I get to bring joy and empowerment to others. My career in real estate isn’t just about transactions—it’s about helping people create a future filled with promise.

 

With 20 years of experience as a REALTOR®, I’ve encountered virtually every scenario and take pride in confidently guiding my clients through any market. My goal is to handle every step of the transaction so they never feel stressed. I start by clearly explaining what to expect, then walk them through the entire process, ensuring there are no surprises later on. I keep everything transparent and tackle any issues as soon as they arise, preventing them from escalating.

 

I believe in building lasting relationships rather than just completing transactions, so I’m always available—even after the deal is done. In fact, every Christmas, I personally bake and deliver pumpkin bread to my clients as a token of appreciation. When you work with me, you can trust that I’ll be there to help with any future real estate needs. With honesty, proactive problem-solving, and a genuine commitment to my clients’ comfort, I support and guide them at every stage of their real estate journey.

 

Sincerely,

 

 

Matt Gregorin