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.