Wil Brawley ’92 · TWP #33
From The Woodberry Podcast by Woodberry Forest School
November 11, 2025 · 34 min · Season 3 · Episode 5
About this episode
Headmaster Byron Hulsey interviews alumnus Wil Brawley about his journey and the values instilled by Woodberry Forest 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.
People in this episode
Host: Byron Hulsey
Guest: Wil Brawley
Topics covered
- entrepreneurship
- alumni relations
- school values
- community connection
- personal journey
Keywords
- Woodberry Forest School
- Wil Brawley
- entrepreneur
- ScheduleFly
- alumni
- school values
- community
Mentioned in this episode
Organizations: ScheduleFly, Woodberry Forest School
More episodes of The Woodberry Podcast
- Drew Collier ’03 · TWP #40 · May 21, 2026 · 28 min
- Julia Hixson · TWP #39 · May 1, 2026 · 36 min
- Jason Ramsden · TWP #38 · April 15, 2026 · 32 min
- Colin Gay ’93 · TWP #37 · January 29, 2026 · 33 min
- Sean Harvey · TWP #36 · January 13, 2026 · 29 min
- Dr. Michael C. Reichert · TWP #35 · January 8, 2026 · 33 min
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