Stang Stories

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, community-rooted organizations, and Diana's practical advice for students exploring meaningful careers.

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 building space technology, the company’s mission-driven focus on reliable mission execution, plans to expand satellite and processing capabilities, and his advice to students to find a guiding purpose and ways to serve their communities.

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 Colby College and through the diverse learning experience that have guided his career as an architect and designer. Lyle offers advice for Milton students to make the most of their years and relationships and to dream big.

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' 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.