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Jack Roach has spent a lifetime learning from coaches—and helping coaches and athletes learn from one another.

In this conversation, Jack reflects on his time leading USA Swimming’s National Junior Team, where he helped create developmental experiences that connected young swimmers with senior athletes and brought coaches into a broader web of relationships. But his philosophy extends well beyond any particular program: coaches shouldn’t simply provide answers. Their job is to ask questions, deepen awareness and help reveal the wisdom already developing within the athlete.

We discuss purpose, autonomy, the difference between being unable and unwilling, admitting weakness as a coach, and why genuinely caring about someone sometimes requires walking directly into difficult conversations. Jack also shares lessons from Eddie Reese and his longtime mentor, Jon Urbanchek—including one question that has stayed with him: How much are you willing to care?

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What makes swimmers want to keep showing up—not because an attendance policy requires it, but because they genuinely want to be there?

Jonathan Kaplan, head coach and director of SwimRVA, joins Chris to discuss a collaborative approach to coaching built around athlete ownership. Jonathan explains why he has never used an attendance policy, how coaches can teach swimmers to manage the psychological demands of practice, and what happens when an athlete’s entire identity becomes tied to results.

They also explore confidence without false modesty, the damage created by praising outcomes while ignoring the process, and why much of championship-meet coaching becomes an attempt to undo lessons athletes learned when they were younger.

Jonathan then shares how SwimRVA was designed around the needs of its community—removing barriers while creating space for everyone from seasonal participants to nationally competitive swimmers—and why good leadership requires enough confidence to question your own ideas.

The result is not a rejection of performance. It is a different path toward it: build better people, give swimmers meaningful ownership, and create a program they don’t want to leave.

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What does it take to build a championship-level program without allowing college swimming to become purely transactional?

Stanford men’s swimming head coach Dan Schemmel joins Chris DeSantis to discuss his unlikely path from Hawaii to one of the most prestigious jobs in the sport—and the moment he finally felt that he belonged there. They explore how Stanford is navigating NIL, the transfer era, and the growing pressure to treat the athlete-coach relationship as an exchange of immediate benefits.

Dan also explains why recruiting athletes who genuinely love swimming matters, how a strong team culture can sustain people when their individual motivation fades, and why the sport needs to better recognize age-group and club coaches. The conversation closes with a look at leadership, the difference between “learners” and “knowers,” and whether faster performances are necessarily producing better swimmers.