Stang Stories
A platform to engage Milton’s students and alumni through conversation.
Episodes
In this episode of Stang Stories, host Hunter Caggiano '27 interviews Milton alum Diana Rakow '95, president and CEO of Hawaiian Airlines. Diana recounts her unconventional career path from chemistry at Harvard to public health and healthcare leadership, and ultimately to aviation at Alaska and Hawaiian Airlines. They discuss the influence of Milton’s people and arts on her leadership style, the challenges of leading large, c...
On this episode of Stang Stories, Molly O'Brien '26 interviews Jennifer Saarbach '02, co-founder of the Wall Street Skinny podcast, about her formative years at Milton, her Princeton studies, and her early career on Wall Street. Jennifer also explains why she transitioned to real estate and offers advice to current Milton students.
On this episode of Stang Stories Gustavo dos Reis '26 interviews Milton alum Betsy Beers '75, a TV and film producer behind hits like Grey's Anatomy, Scandal, How to Get Away with Murder, and Bridgerton.
Betsy reflects on how Milton shaped her curiosity and confidence, her path from theater and script reading to producing, lessons learned from failures and odd jobs, and practical advice for students pursuing the arts.
On this episode of the Stang Stories podcast, Hunter Caggiano '27 sits down with John Serafini '94, founder and CEO of Hawkeye 360. John shares his journey from Milton Academy to West Point, military service, Harvard, venture capital, and founding a company that uses small satellites to detect and analyze radio frequency signals for defense, intelligence, maritime awareness, and emergency response.
John discusses the challenges of ...
On this episode of the Stang Stories podcast, Giselle Figueroa '27 sits down with Lyle Bradley '95, an architect and partner at ART Architects. Lyle shares his experience as part of the Milton 13 year club, the kindergarten origins of his passion for woodworking, and some of his favorite renovation projects that his architecture firm has completed on Milton's campus.
Giselle and Lyle trace his journey from Milton Academy to C...
Host Tyla Tsang '28 interviews Frank Smith '07, a Milton alumnus turned TV writer, about his time at Milton, speech and debate, leadership lessons, and an unexpected career pivot from pre-med to entertainment.
Frank discusses overcoming rejection, queer representation in his work, projects like Open To It, and offers practical advice for students navigating school, college, and career choices.
In this episode of the Stang Stories Podcast Jazlyn Fuentes '25 interviews Milton alumnus Robb Chavis '94 about his time at Milton, memorable school moments, and influential teachers. He shares his senior project, balancing academics and activities, and lessons learned from setbacks.
Rob traces his path from Duke and Harvard Law to advertising and then television—writing spec scripts, moving to L.A., breaking into writers' ro...
In this episode Hunter Caggiano '27 interviews Karl Austen '82, an entertainment lawyer at Jackoway Austen, about his path from boarding school and speech team to Amherst, Harvard Law, and a career negotiating major film and TV deals for clients like Matt Reeves, Jude Law, and Seth MacFarlane.
Karl reflects on how Milton shaped his love of storytelling, shares early Hollywood anecdotes, and offers practical advice for young people ...
On this episode of the Stang Stories podcast, Molly O'Brien '26 interviews Mike Connolly '96, about his journey from South Boston to Milton Academy—earning a full scholarship, repeating seventh grade, bonding over sports and homeroom, and finding inspiration in an astronomy class and senior projects in photography and essays.
Mike recounts his college years at Tufts, a shift from engineering into sales, the mentors who guided...
Welcome to Stang Stories with Oliver Sin '25 featuring Tonantzin Carmona '08. In this episode she recounts her transition from Chicago’s Little Village to Milton, the mentors and traditions that shaped her, and how listening to diverse perspectives led her into a career in public policy. Tonantzin discusses building Chicago’s municipal ID, work at Brookings, Treasury and the White House NEC, lessons on leadership and pu...
Welcome to this episode of the Stang Stories podcast, where Jason Yu '25 interviews Mark Denneen '84, Milton Academy alumnus and CEO of Denneen & Company. Mark shares his journey from being a student at Milton to leading a successful growth strategy consulting firm. He discusses the profound impact Milton had on his intellectual and professional development, highlighting the significance of lifelong friendships and the foundati...
In this episode of the Stang Stories podcast, Milton Academy senior Jason Yu '25 interviews Kabeer Parwani '07. Kabeer shares his journey from being an improv enthusiast and theater lover at Milton to serving as a Foreign Service Officer at the U.S. Embassy in Lisbon, Portugal. He reflects on the significant impact his school years had on his interest in international diplomacy and how these experiences shaped his career trajectory...
Join us on this episode of the Stang Stories podcast as Gustavo dos Reis sits down with Mr. Lamont Gordon '87, a proud Milton Academy alumnus and the executive director of College Visions. Reflecting on his years at Milton and beyond, Mr. Gordon shares the transformative experiences and leadership roles that shaped his path in education. From advocating for minority students to founding impactful programs at Brown University, his j...
Welcome to this inspiring episode of the Stang Stories podcast! Ladia Khaing sits down with Jamie Mittelman, a Milton alumna and CEO of Flamebearers, a platform dedicated to uplifting the stories of female Olympians and Paralympians. Jamie shares insights from her time at Milton, her eclectic educational and professional journey, and her ardent passion for advocating women's stories in sports media.
Discover how Jamie went from par...
In this episode of the Stang Stories podcast, host Jazlyn Fuentes '25 converses with Dr. Alexandra Rodman, a distinguished alumna from Milton's class of '06 and a psychology professor at Northeastern University. Dr. Rodman shares insights about her transformative experiences at Milton, including her involvement in boarding life and the Octet music group, which paved her path toward acapella in college.
Dr. Rodman discusses her acad...
In this episode of the Stang Stories podcast, Jason Yu '25 chats with Dr. Annie LaVigne '07, a current instructor at Johns Hopkins University School of Medicine. There, LaVigne focuses on intersecting the health humanities with radiation oncology, bringing humanism to the center of the medical field. Learn about LaVigne's daring cross-country biking treks, swims with sharks in South Africa, and current research on radiotherapy dese...
In this episode of Stang Stories Podcast, Ladia Khaing '25 sits down with Maggie Jackson, a distinguished non-fiction author and Milton alumna from the class of 1978. Maggie shares her transformative experiences at Milton and how they laid the foundation for her illustrious career as a journalist and author.
Delve into Maggie's journey from her early days at Milton, where she honed her skills in journalism and theater, to her acade...
In this captivating episode, Oliver Sin sits down with Mr. Rod Skinner '72, a distinguished alumnus of Milton Academy's class of 1972 and the Dean of College Counseling from 1999 to 2023. Mr. Skinner shares his unique experiences as a student during the Vietnam War era, shedding light on the anti-war protests that marked his high school years.
The conversation delves into the historical context of Milton Academy, contrasting the in...
In this episode of Stang Stories, Jason Yu '25 interviews Louis Demetroulakos '15, the Strategic Alliances Director at Playroll, a company dedicated to facilitating global expansion for businesses. Louis, who served as Head Monitor during his senior year, shares his journey through Milton, NYU, Shanghai, and various other cities worldwide, highlighting the cultural awakenings he experienced along the way. As a new school year appro...
In this episode of Stang Stories, Diane Asiedu interviews Claire Cheney ‘02, founder of Curio Spice. Claire shares her passion for spices with audience members and reveals how Milton influenced her journey to finding happiness and success in her professional life.
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