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' rooms, and becoming a co-executive producer at ABC studios. He offers advice on taking risks, finding your voice, and using life experiences to fuel creative work.

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 interested in entertainment law.

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 him, and how a personal loss led him to found Pay Forward Coaching in 2022, a nonprofit offering thousands of free career coaching sessions.

He closes with practical advice for current Milton students: do more extracurriculars and keep relationships alive.

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 public speaking, and her measured view on crypto and equitable economic policy. She closes with practical advice for students: take risks, be kind, and know your why.

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 foundation of essential skills such as critical thinking and public speaking.

Mark also reflects on his pioneering efforts as the founder of the Milton Paper, emphasizing the importance of independent student voices. He talks about his career trajectory, the challenges and rewards of entrepreneurship, and the role of history and leadership in shaping his path. Tune in to explore Mark's experiences and gain insights into the world of consulting, innovation, and the power of education.

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.

The conversation delves into Kabeer's day-to-day responsibilities as a political officer, the cultural challenges he navigates, and the diplomatic skills he employs to foster strong U.S.-Portugal relations. Kabeer also shares anecdotes from his global postings and provides valuable advice for current students aspiring to a career in international affairs. This episode offers a unique blend of personal history and professional insights, illustrating how leadership, adaptability, and communication are key to success in the world of diplomacy.

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 journey is a testament to the power of education and community.

Discover how the values of confidence, diversity, and authenticity learned at Milton Academy guided him through his career and informed his work with organizations like the Posse Foundation. Mr. Gordon’s story is a compelling narrative of dedication to making education accessible and equitable for all students. Gain insights into how Milton prepared him for success and the crucial mission he continues to pursue in the nonprofit sector.

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 participating in a multitude of extracurricular activities at Milton, to earning advanced degrees from prestigious institutions, and eventually finding her calling in supporting women athletes globally. She discusses the challenges and adversities faced in promoting women's sports and the transformative power of storytelling in making real-world impacts.

Join us for a conversation that celebrates resilience, inspiration, and the drive to make a positive change in the world through the power of storytelling and advocacy.