How The Student Becomes The Advisor

Gregory Dexter was barely out of school when he faced his teachers again.

This time, he wasn’t their student. He was their advisor.

Dexter, age 24, is in his fourth year with New York Life, working as a financial advisor with Eagle Strategies, a registered investment advisor. 

He has been licensed since his junior year at St. Joseph University in Philadelphia, and he qualified for Million Dollar Round Table in 2020. 

Dexter is the third generation and the fourth member of his family to represent New York Life. His grandfather, Gregory Genovese, began his career in Long Island, N.Y., in 1965 and is now retired. Dexter’s uncle, also named Gregory Genovese, is a New York Life agent in Long Island, and another uncle, Mike Genovese, is an active agent based in California.

Despite his young age, Dexter has been able to gain the trust of clients who have known him ever since he was an aspiring percussionist attending a performing arts high school in a small town in northern Delaware. 

“I had a few clients while I was in college, but my first clients out of college were former teachers of mine,” he said. “I didn’t prospect them. But my mom worked at my former school. And it’s a place where everybody knows everybody. And things would come up in conversation — someone’s worried about the market, someone’s not happy with their financial professional. And my mom would say, ‘Maybe you should sit down with Gregory and have a conversation.’

“Here I was, a 22-year-old guy sitting down with my former teachers, asking them what are their incomes, what are their debts, what are their assets. So that was kind of an interesting experience because I was now in this environment where I looked up to them as mentors and now they’re looking to me for financial advice. They shared their wisdom with me, and now I’m sharing mine with them. But I think it gets to the heart of why I do what I do is because I know I’m going to make a difference in that person’s life.”

Dexter originally had planned to be a management consultant. He had an interest in finance, he enjoyed problem-solving and he liked to help people. By the time his junior year rolled around, he decided to get serious about zeroing in on a career, and he approached New York Life for a job as an agent. He quickly became licensed and was on his way.

“It was relatively easy for me to get in because of my family,” he said. “But it was up to me to say, OK, what am I going to make with this? Do I like it? Is it a good fit for me?”

Despite his early start in the business, Dexter said he still questioned whether it was what he wanted to do after graduation. “I wasn’t thinking about the traditional concerns when you’re in the business, like where’s the client going to come from? How am I going to make a living? How am I going to do all these things? For me, the question was, is this something I want to do when I graduate?”

It didn’t take long for Dexter to realize that the industry provided him with an opportunity to help others while pursuing his interest in finance.

“To me, this was the perfect fit, because I really am directly helping people, whether it’s protection with life insurance or helping them handle their retirement accounts. There are so many other programs and strategies and ideas that can help people and make a difference in their lives.”

Dexter said that after he graduated, “I hit the ground running and never looked back.”

A turning point in his career, he said, occurred when he was assigned to service a client, husband and wife, who did not have an agent associated with them. After meeting with them and reviewing their coverage, Dexter said, the wife revealed a serious medical issue. On top of that, her term life insurance was about to expire. Dexter was able to convert her term coverage into a permanent policy, which he said, “took a huge weight off her shoulders.”

“That was the first time where I saw really the benefit of what we do come into play not from delivering a death benefit but from helping give someone peace of mind while they are alive.”

Dexter said he is inspired to help as many people as he can. 

“That’s my challenge. How many people did I help today? How many people can I get in front of to show what I do? How many people can I assist with something so basic as life insurance or something as complex as a financial plan?”

Even though Dexter has been in the business for only a short time, he helps mentor the newer members of his general office. 

“A lot of times, they try and put the cart before the horse — to try to close the deal before they really even have an idea of what they should propose. I tell them you have to be able to understand what is going on before you can solve the problem.”

He shares with newer agents the importance of looking at the agent relationship as more than transactional.

“There are some clients who think buying life insurance is like buying a car. But you need to be relationship-oriented instead of looking at life insurance as a transaction where you never see the client again after the sale.

“I tell my clients that you’re going to hear from me even more now that you’re a client. I make them understand that this is a trusting relationship that we’re going to have. And in order for me to do the best job I can for you and your family, I’m going to need to know some of the most intimate financial details that you’ve probably never even shared with anybody. Maybe you probably haven’t even shared it with your spouse. But in order for us to have the best possible solution, we’re going to have to talk about this stuff.”

The COVID-19 pandemic forced many advisors to adapt to a remote way of doing business, but Dexter worked remotely long before it was the norm. He works from his home in the Philadelphia suburb of West Chester, Pa., going into the office occasionally but mostly traveling to where his clients and prospects are. 

His clients represent a wide range of occupations — teachers, firefighters, business owners, tradespeople, retirees and pre-retirees. “I’m a firm believer that everybody out there — there’s at least one thing I can do for them. It’s just a matter of getting them to sit down with me.”

Dexter frequently bounces ideas off his grandfather, who says that many of the same techniques used back when he started in the business are still relevant today.

“I tell Gregory that the basics haven’t changed,” Gregory Genovese said. “I tell him how important referrals are. And I tell him you have to be able to accept the nos and move on. I also talked to him about setting a particular goal and then rewarding yourself when you meet that goal.”

Genovese said he didn’t introduce his grandson to the business, “but he made it his own. He is conscientious and honest, and he will go far.”

Outside of work, Dexter’s love for music is still part of his life. He played drums in a band while at St. Joseph, performing during basketball games. He has played in a few jazz bands and is trying to find enough musicians to form a jazz big band. 

He is active in performing arts organizations and also serves on some nonprofit boards in his community.

“I don’t serve on boards to get business,” he said. “But I do it because I genuinely care about the work I’m doing. And then business just happens to flow from there.”

Creating happiness and helping people are at the core of everything Dexter does in and out of the office. 

“It’s all about what did I do to help somebody today — whether they enjoyed the music that I provided for them or whether it was the financial advice I gave.”

Susan Rupe is editor in chief, magazine, for InsuranceNewsNet. She formerly served as communications director for an insurance agents' association and was an award-winning newspaper reporter and editor. Contact her at [email protected].