Jason Simmons

About Jason

My interest in finance began with childhood walks around Baltimore, searching for coins with my Pop. My grandparents, though modest in means, were generous and loving, teaching me that money isn’t everything. However, they instilled the value of striving for a better future, a lesson passed down through my parents.

My dad, a paint salesman and my best friend, and my mom, a part-time HR coordinator, showed me the importance of hard work and doing the right thing. When I started my finance career in 1998, I carried those values with me. Over the years, I’ve had the privilege of helping clients from all financial backgrounds—people like my grandparents, my parents, and those with greater financial success. Building relationships and friendships along the way has been the most rewarding part of my journey.

I attended Calvert Hall in Towson, where I first opened an investment account with my uncle, sparking my lifelong fascination with the stock market. I went on to graduate from Loyola College with a finance degree and have worked at several investment firms, including Red Oak Financial Group, where I’m happy to have returned home.

I’ve lived in Bel Air, MD, since 1986 and now reside with my three sons. My youngest, Trevor, keeps me active with soccer, while my oldest, Jake, studies business, and Dylan has been in an HVAC apprenticeship. We’re passionate sports fans and enjoy attending Ravens and Orioles games together.

A lot has changed since 1998, but the timeless values of learning, hard work, and respect remain at the core of my life and work. I aim to live by those values every day and pass them on to my boys as they forge their own paths.