Colin Milbourn & Kingston Oliver on Finding Your Place and Leading with Purpose

In Episode 23 of Season Two of The Late Start Show, we sit down with two University School seniors who took different paths to US, and found their place in the same community: Colin Milbourn, a two-sport athlete in football and basketball who transferred in looking for a bigger challenge, and Kingston Oliver, a varsity basketball player and cellist whose move to US brought an early culture shock and a fast transition through sports. Together, they reflect on what it really feels like to “find your footing” at a new school, meeting people through teams, leaning on teachers and mentors, and discovering that brotherhood shows up in everything from the classroom to the student section. Along the way, they shout out the classes and educators that shaped their experience and talk about how sports, clubs, and music widened their circles and built relationships that stuck.

From there, the conversation shifts to senior-year leadership and what it means to carry yourself when the stakes are higher, staying steady in big moments, leading by example, and helping build a culture where showing up for each other is the norm. Colin and Kingston break down the energy behind this year’s school spirit, why their class has kept it going, and how support can look like cheering at games, or showing up to an orchestra concert. They also get real about balancing academics, athletics, friends, and family, share what they’ll miss most about a small-school environment, and offer advice to younger students on finding support early and making the most of the time you have. They close with their “why”: gratitude for family sacrifice, and a commitment to being intentional in everything they do.

Credits to Theo Walter for Production and Editing, Russ Nobles for the Intro and Outro songs, Mr. Wickboldt for being our advisor, and you for listening to our podcast and keeping up with the latest US news.