Our annual Nicky Chapin Lecture, a cherished tradition for the whole Chapin community, welcomed back Regina Gilgan ’94 as its 23rd speaker.
This special event is named after alumna and former faculty member Nicky Stout Chapin ’52, who, in 1957, began a 43-year career at Chapin as an Advisor, Class 7 supervisor, and teacher of history and geography before retiring in 2000.
The morning began with breakfast and conversation in the Berendsen Room, where our guests, family members, professional community (PC) and alumnae gathered to celebrate and reconnect. (Several members of Ms. Gilgan’s class came to support her!)
At 10 a.m., Upper School (US) students filed into the Assembly Room, eager to hear about Ms. Gilgan’s journey from being a Chapin student to becoming the Senior Executive Producer and Managing Editor of Mad Money with Jim Cramer at CNBC.
Following a warm introduction from Arreyana K., Class 12 President of News, and Nicky Stout Chapin ’52, Ms. Gilgan delivered her presentation, From the Classroom to the Control Room: Shaping a Voice in Media. Addressing the US, PC and alums, she shared inspiring stories and valuable insights from her impressive career in television.
After graduating from Chapin and Georgetown University, Ms. Gilgan began her career at CBS News, working on news gathering and in the documentary unit. She later joined CNBC where her “entrepreneurial drive helped her build one of the best-known brands in television,” Mad Money with Jim Cramer. The show, which launched in 2005, was designed to help viewers think like professional investors and learn how to analyze the stock market.
Ms. Gilgan structured her talk around the three C’s — curiosity, courage and community — lessons she shared that she’d first learned at Chapin and has carried with her throughout her professional journey.
1. Curiosity
“Chapin students vibrate with curiosity,” Ms. Gilgan said. “Chapin wants you to ask questions and explore.” She encouraged current students to take advantage of every opportunity within the School — to explore, experiment and try new things.
During college, she noted, her career path took an unexpected turn when she didn’t receive the CBS News internship she had hoped for. Instead, she was placed in a different newsroom at CBS — an experience that proved transformative. At another point, she decided to take a leap into financial journalism. She was hired at CNBC for a short project and the work she did there set her on a path from a six-week gig to a 22-year career. “Sometimes the unknown paths turn out to be the best ones,” she reflected.
Ms. Gilgan emphasized that learning new things and developing a range of skills is essential. She acknowledged that mistakes are inevitable and what truly matters is learning from them.
2. Community
Ms. Gilgan spoke about the value of the relationships built at Chapin — with classmates, teachers and mentors — and how they “show up again and again in your life.” That sentiment was reflected in the number of classmates who came to support Ms. Gilgan during her lecture, decades after graduation.
“Being a part of a community creates opportunities for connection and awareness,” she said. “And being part of a community means challenging it.”
At Mad Money, Ms. Gilgan has always strived to foster a positive, supportive work environment where everyone feels valued. Early in her career, she noticed that many producers and anchors didn’t know the names of those working behind the scenes — something she made a point to change. By leading with empathy and inclusion, she has built an integrated, collaborative team that embodies the very sense of community she had at Chapin.
3. Courage
“You are on your own, kid,” Ms. Gilgan said, referencing a Taylor Swift lyric — familiar to many in the audience. She explained that she interprets this line not as isolating, but as empowering — an invitation to trust yourself and “be brave enough to take your own winding path.”
When Ms. Gilgan launched Mad Money, she became the youngest and only female Executive Producer at the network at that time. It required courage to face skepticism and sexism in the workplace, but she refused to let those barriers deter her.
Ms. Gilgan shared an example from her early days working on Mad Money when she and Jim Cramer were being interviewed for a feature on another network. When Ms. Gilgan arrived, the female reporter said "I'm waiting for the Executive Producer to arrive and he's late."
Ms. Gilgan realized it had not occurred to the reporter that the show could possibly be run by a woman. While the reporter apologized the next day in a thoughtful letter, the experience itself was disheartening, and a moment that helped shape the leader she would become, giving her confidence and determination to continue her important work. “Even people with the best intentions have blind spots,” she said.
To conclude her lecture, Ms. Gilgan urged students to “pay attention to the people around you — don’t be on your own mission,” as the people around you, you not only work with but can learn from.
Following Ms. Gilgan’s talk, the floor opened for a Q&A session. When asked what she was most proud of in the show, she said that Mad Money has helped countless viewers across generations gain confidence and success in investing. She recalled hosting Mad Money college events and hearing firsthand how the show had changed lives.
The Assembly Room erupted in applause and excitement as this notable alumna left the podium — a powerful and inspiring start to the morning for the Chapin community.
