Growing up in Baltimore, Jason Caldwell had what he calls the stereotypical “African American in an inner city” experience—until his athletic prowess earned him a scholarship and a chance at a different life. Today, he’s a three-time Fordham graduate and vice president of private wealth management at Goldman Sachs.

“I stand on the shoulders of hundreds of people who saw something in me and who gave me an opportunity to be successful,” he said. “It was up to me to continue to push forward, but there were hundreds of people who actually pried the door open or at least gave me a glimpse of what success looked like.”

As a member of the President’s Council—a group of successful alumni who are committed to mentoring Fordham’s future leaders, funding key initiatives, and raising the University’s profile—and a loyal supporter of both Fordham athletics and the Fordham Founder’s Undergraduate Scholarship Fund, Caldwell said he is able to pay it forward to students who “need that one shot or opportunity. That’s all it took for me to get where I am today: just somebody opening the door and showing me what’s possible.”

Redefining Success

Caldwell and his siblings were raised by their mother, Dawn, in Baltimore. He didn’t have much ambition as a kid: His goals were to earn a high school diploma, secure a job in government, and have a baby—“that was what the legal route of success was,” he said. Though Caldwell is close to his mother and counts her as the most positive influence in his life, as a kid, the most financially successful people in his life were drug dealers.

“I vividly remember modeling myself behind my uncle, who was in that life and who sold drugs, and trying to be like him because he was the richest person I knew, thinking, ‘If I want to be rich … then I need to do what he does or act like him,’” he said.

Fortunately, Caldwell was a talented athlete who earned a basketball scholarship to attend St. Paul’s School for Boys, a college preparatory school outside of Baltimore. And when two of his brothers were murdered when he was in high school, prompting his mother to send him to live with one of his classmates, he got a glimpse at another kind of success: His classmates were thinking about colleges and careers, and they had both a “mom and a dad at home,” showing him “oh, this is what a family looks like.” Caldwell realized that not only did he now want the same things, but with a bit of focus and effort, he could persevere and earn them. When he earned a football scholarship to attend Fordham, he got his chance.

Leveraging an Injury for a Master’s Degree

At Fordham, Caldwell studied finance at the Gabelli School of Business. Though he had a new focus and determination, he said he couldn’t have succeeded without the support he received on campus: He, and countless other student-athletes, had a Catholic nun, Ann Walsh, R.H.S.M., behind them. As a sort of second mom, “she was the person that, if we were doing something we shouldn’t have been doing, would discipline us in her beautiful way. … You could tell it came with love,” he said.

She would “bring you to her office and walk you through an entire book; she’d read an entire book with you to make sure that you understood the coursework,” he said. “She went above and beyond what her job required to help us succeed. She will always be one of the catalysts of my success.”

During his first year on the football team, Caldwell was injured, giving him the option to come back for a fifth year to play. He agreed, but only if he could get into a master’s program. He did: He earned a B.S. in finance in 2010, an M.A. in humanities in 2011, and an M.B.A. in 2017.

Getting a Leg Up from the Fordham Network

Though he worked hard and made the most of the support and opportunities the University offered him, Caldwell is the first to point out that he owes many of his career breaks to the Fordham alumni network.

He learned about his first job after graduation, as an associate on the variable annuity sales desk at MetLife, from one of his teammates, whose father was an executive at the company. Since then, he’s worked at three other companies, and every job he’s gotten since he graduated has been through a Fordham alumnus.

Arguably the most important connection he forged at the University, though, was with Katheryn Pereyra-Caldwell, FCRH ’08, now his wife. Already parents to 2-year-old Chloe, the couple is expecting their second child, a boy, in November.

“I met my wife at Fordham,” he said. “The first three clients I brought on here at Goldman have been Fordham alumni. … Fordham has just been the anchor of my career, of my time and my life here in New York City, so I feel like it’s my duty to give back as much as I can.”

Holding Open the Door

Caldwell said he feels indebted to the University for “opening so many doors, creating so many opportunities when it comes to jobs, or advice, or mentors,” and that’s why he feels that it’s his duty to give back however he can—sharing his time, speaking at events, giving financially.

This past May, Caldwell attended a graduation reception at the Rose Hill campus for first-generation college students, getting to know the small group of attendees and encouraging them to stay in touch.

Through such events and serving on the President’s Council, Caldwell said he believes he’s in the best position to help pry open doors for Fordham students from backgrounds similar to his own, students who just need a chance to thrive. He also hopes that, with that support, those students feel empowered to take risks.

“I wish I would’ve taken more chances [growing up],” he said. “As a Black man in America, I felt like I didn’t have that many chances, so when I get this one opportunity, I got to take it and I got to make the most of it. Now how I look at life is it’s okay to fail. It’s okay to fall short or to start over. It’s not about how many times you get knocked down; what’s more important is how many times you get back up.”

Fordham Five (Plus One)

What are you most passionate about?
I’m most passionate about the next generation. Some would argue that I’m a success story, but what they fail to realize is that I could not get to where I am in life without the help of others. Because of this, I feel like it’s my duty to give back to the next generation. This is why I go out of my way to help as many people as I can.

What’s the best piece of advice you’ve ever received?  
Don’t be afraid to take risk. Success in my mind is about how many times you get back up after being knocked down.

What’s your favorite place in New York City? In the world?
This is a tough question. When I was younger, I would have said the end zone after scoring a touchdown on the football field at Fordham, but now I would say the whale room at the American Museum of Natural History, [where I go]with my 2-year-old daughter, Chloe.

My favorite place in the world is back home in Baltimore with my mom and siblings, enjoying a bushel of Maryland blue crabs.

Name a book that has had a lasting influence on you.
The Daily Stoic, a book written by Ryan Holiday that provides 366 meditations on peace, wisdom, and perseverance. Each day, you’re supposed to read an excerpt from the book, which gives you a full day of insight and reflection.

Who is the Fordham grad or professor you admire most?  
The Fordham grad that I admire the most is my wife: one of the hardest workers I know. She has overcome a tremendous amount of adversity and is now a well-respected attorney.

What are you optimistic about?  
Although the political and social landscape has been rocky, I am encouraged when I see diversity in leadership at big institutions like Fordham University. I haven’t had a chance to meet Tania Tetlow yet, but I’m excited to see the first woman and first lay president to lead Fordham University since it was founded.