Rise, Heal, and Grow (Episode 34) with Leah M Hill featuring Randy Ross

In this engaging episode of Rise, Heal, and Grow, Leah sits down with Boston-based writer, performer, and world traveler Randy Ross, whose sharp wit and fearless storytelling have captivated audiences across the U.S., Canada, and the U.K. Randy shares how a disastrous four-month solo trip through developing countries became the inspiration for his acclaimed novel God Bless Cambodia and two hit one-man shows, including The Chronic Single’s Handbook and Tales of a Reluctant World Traveler. He opens up about crafting his newest book, The Squid and the Spaceman, a dysfunctional love story exploring how far we can—or should—go to change for someone we love, and previews his upcoming live performance blending scenes from the novel with insights from his research on loneliness. With reflections on growing up in Westchester, life in Boston since the ’80s, a decade on the Fringe Festival circuit, and the belief that “persistence pays off,” Randy reminds us that it’s never too late to take risks. His trademark humor—featuring favorites from Beverly Sills and Steven Wright—makes this conversation both heartfelt and hilariously unforgettable.