Q
You enlisted in the U.S. Army after high school because you felt you needed more structure. What did you hope the Army would provide?
A
I was fortunate to have people in my life who gave me honest advice. They told me that college right after high school might not be the best path for me. So I enlisted in the Army as a light infantry soldier. The experience taught me discipline, teamwork, and how to appreciate the things we often take for granted.
FAVORITE YANKEES PLAYER: Don Mattingly (“What a great hitter and a great presence on the team. I admired everything about him, even the long hair.”)
FAVORITE VACATION SPOT: Montauk, Long Island, New York (“But Montana runs a very close second.”)
FAVORITE BASEBALL MOVIE: The Natural
FAVORITE ACTOR: Robert De Niro
FAVORITE MUSICIAN: “I’m a classic rock guy through and through. Led Zeppelin first, but I’ve always got The Rolling Stones and Van Halen in the mix.”
FAVORITE WESTCHESTER COUNTY, N.Y., RESTAURANT: Crabtree’s Kittle House (“They have one of the greatest wine cellars in the world and an atmosphere to match.”)
Q
Growing up, you played a lot of baseball, and you had a neighbor who played for the New York Yankees.
A
One of my best friends growing up was the son of Frank Tepedino, who played for the Yankees, Milwaukee Brewers, and the Atlanta Braves. Having someone like that across the street was incredible. Baseball was my first love. I played from when I was 5 years old until I graduated high school. It taught me about dedication, teamwork, and resilience, lessons that still resonate.
Q
Who were your childhood heroes?
A
Having a Major League Baseball player across the street certainly left an impression. But my father was my hero—an incredibly bright man and one of the best salespeople I’ve ever known. He had a long, successful career in pharmaceutical sales, but more than that, he was genuine, compassionate, and led by example.
Q
Do you apply lessons from your father in your work today?
A
Absolutely. My father was deeply empathetic and believed in treating everyone with respect, no matter their role or position. He always gave people the benefit of the doubt and looked for the best in them.
Q
What does a perfect weekend look like for you?
A
My wife and I have four kids—a daughter and three sons—and they are all incredibly active in sports. A perfect weekend for me is spending time with them, catching their games, and just being together. When we can get away, we love going out to Montauk, on Long Island, to unwind and enjoy the beach.
Q
After selling health insurance for Aetna, you started your own business, JS Diamond Group. Did you always have entrepreneurial aspirations?
A
Yes. Even as a kid, I was shoveling driveways or mowing lawns to earn a few dollars. When I entered the corporate world, I quickly realized I wanted more control over my own destiny. That drive led me to start JS Diamond Group, which became the foundation of Marshall+Sterling’s employee benefits practice.
Q
What three words would your co-workers use to describe your management style?
A
I’d like to think they’d say, “leads by example.” Leadership is about setting the tone—being willing to roll up your sleeves, make tough decisions, and demonstrate the values you expect from others.
Q
Is there a lesson you learned in the Army that you carried into your business life?
A
Accountability. In the Army, accountability is everything—to yourself, your team, and your mission. In business, success depends on people taking ownership of their responsibilities and having each other’s backs.
Q
What is something your co-workers would be surprised to learn about you?
A
Probably how different I am at home with my family. In the office, I can be very focused and direct. At home, my kids bring out the softer side of me.
Q
If you could change one thing about the insurance industry, what would it be?
A
I’d love to see more data transparency and clarity in how premiums are developed and risks are underwritten. There’s tremendous opportunity for the industry to become more client-centric through technology, analytics, and communication.
Q
What gives you your leader’s edge?
A
I’m not afraid to take on challenges head-on. That mindset, coupled with the incredible employee-owners I work alongside, gives us a real competitive edge.
