In this episode of The Woodberry Podcast, Dr. Byron Hulsey welcomes Jason Ramsden, host of This Empty Nest Life, for a thoughtful conversation about one of parenting’s most significant transitions.

As children take their next big steps, heading off to college, boarding school, or into independence, parents are often left navigating a new and unfamiliar season. Byron and Jason explore the emotional dynamics of becoming an empty nester, offering practical advice on how to process the change, maintain strong relationships, and build healthy habits in this next chapter of life.

Drawing on his work as a coach and podcast host, Jason shares insights on finding purpose beyond parenting, staying connected without overreaching, and embracing the opportunities that come with change.

In this episode of The Woodberry Podcast, Headmaster Byron Hulsey reconnects with Colin Gay ’93, Woodberry alumnus and longtime faculty member. After graduating from Woodberry, Colin returned to the Forest to teach, serving the school for 19 years before wrapping up his time on the faculty in 2022. He now works at GovSmart, Inc., while continuing to pursue meaningful challenges beyond his career.

Byron and Colin reflect on Colin’s life path, his years teaching and mentoring boys at Woodberry, and the lessons that emerged from nearly two decades on campus. The conversation also turns to Colin’s remarkable personal goal: a quest to ride his bike 10,000 days in a row. Colin shares what the streak represents, how it has shaped his discipline and perspective, and why daily commitments—big or small—can become anchors in a meaningful life.

In this episode of The Woodberry Podcast, Headmaster Byron Hulsey is joined by Sean Harvey, founder of the Warrior Compassion Institute and a men’s engagement strategist whose work focuses on purpose, healing, and authentic connection.

Byron and Sean explore how Sean’s work with men, helping them confront deeper questions of identity, meaning, and belonging, aligns closely with Woodberry Forest’s mission of knowing, challenging, and loving the boys in our care. Sean shares what he has learned from working with adult men who are seeking clarity and wholeness later in life, and why intentional formation during adolescence matters so deeply.

Together, they reflect on the cultural divides that fragment our world and discuss how compassion, accountability, and honest conversation can help foster healthier individuals and stronger communities. This episode offers a powerful perspective on what it means to raise young men prepared not just for success, but for meaningful lives.

In this episode of The Woodberry Podcast, Headmaster Byron Hulsey sits down with renowned author and psychologist Dr. Michael C. Reichert to explore the development and education of boys in today’s world. Dr. Reichert is an applied and research psychologist with over 30 years of experience working with children, families, and schools across clinical, community, and educational settings. He serves as Executive Director of the Center for the Study of Boys’ and Girls’ Lives in partnership with the University of Pennsylvania and has consulted and spoken globally on effective practices in boys’ education.

Byron and Dr. Reichert discuss the path that led him to his vital work—blending research, clinical practice, and advocacy—and unpack key ideas about how boys learn, grow, and thrive in relational environments. They dive deep into topics from Dr. Reichert’s influential writings, including Reaching Boys, Teaching Boys, and How to Raise a Boy: The Power of Connection to Build Good Men, discussing the importance of emotional literacy, supportive relationships, and reimagining traditional notions of masculinity in education.

In this episode of The Woodberry Podcast, Headmaster Byron Hulsey is joined by Janney Jay, mother of Morgan Jay ’25, for a conversation about one family's journey through a Woodberry education. Janney shares what led the Jay family to choose Woodberry Forest School and reflects on how the experience has shaped Morgan’s growth along the way.

Byron and Janney also discuss the strength and reach of the Woodberry parent network and how it brings together families from all walks of life and from around the world, united by shared values and a deep commitment to their sons and the school.

In this episode of The Woodberry Podcast, Headmaster Byron Hulsey welcomes Wil Brawley '92, entrepreneur, proud alumnus, and longtime friend of the school. As the co-owner of ScheduleFly, Wil has built a successful business rooted in service and relationships, values that trace back to his time at Woodberry.

Byron and Wil reflect on Will’s journey from his early days as a Woodberry sports camper to his years as a student and now as a dedicated alumnus. Together, they explore the enduring strength of the Woodberry bond, how the school’s focus on honor, humility, and brotherhood continues to shape its graduates and inspire their lifelong connection to the community.

In this episode of The Woodberry Podcast, Headmaster Byron Hulsey welcomes Dr. Tiff Jones, founder and owner of X-Factor Performance Consulting and a Certified Mental Performance Coach. With more than two decades of experience working with professional, collegiate, and youth athletes, Dr. Tiff helps individuals and teams reach their highest potential, both in competition and in life.

Byron and Dr. Tiff discuss the power of mindset and mental skills training in shaping performance, resilience, and leadership. They also explore her holistic approach, which blends behavioral profiling and Chopra-certified practices in health, meditation, and well-being. Dr. Tiff shares how these techniques are transforming not just sports, but also the corporate and educational worlds.

In this episode of The Woodberry Podcast, Headmaster Byron Hulsey welcomes John Gulla, Executive Director of the Edward E. Ford Foundation, for a wide-ranging discussion on the forces shaping secondary education today.

Together, Byron and John explore the broader trends influencing independent middle and high schools, from shifting demographics and financial models to questions of access, equity, and innovation. With years of experience leading and supporting schools across the country, John offers thoughtful insights into both the challenges and opportunities that lie ahead for independent education.

In this episode of The Woodberry Podcast, Headmaster Byron Hulsey welcomes Harry Lavant, an Internationally Certified Gambling Counselor, for a timely discussion on the rapidly evolving world of sports gambling.

Together, Byron and Harry explore how the expansion of legalized sports betting is shaping culture, the unique risks it poses for young people, and the challenges parents and educators face in addressing it. They also brainstorm strategies for fostering awareness and ensuring that communities approach gambling responsibly in the years ahead.

In this episode of The Woodberry Podcast, Headmaster Byron Hulsey sits down with a very special guest, his daughter, Claire Hulsey. A rising senior at St. Andrew’s School in Delaware, Claire reflects on her own educational journey while sharing what it was like to grow up on the Woodberry campus as the daughter of a headmaster.

Byron and Claire talk candidly about the unique perspective that comes with being part of the Woodberry community from childhood, the lessons Claire has carried with her to St. Andrew’s, and the ways her path has been shaped by both family and school life.