Phil Sitter returns to the Great Friends podcast with a conversation that feels more like a leadership workshop than an interview. As the founder and CEO of RepeatMD, Phil shares how he has evolved from building products to building people, reframing culture as the ultimate competitive advantage. He and John explore what it means to “live it, not preach it” — the discipline of modeling clarity, accountability, and integrity so that teams naturally rise to the same standard.

Throughout the discussion, Phil unpacks the systems that allow RepeatMD to scale without fracturing its identity. He introduces the idea of strategic anchors — principles that guide every decision, from hiring to product development. These anchors, such as Patient Obsession, Product Leadership, and Your Success Is Our Success, act as the company’s internal compass, ensuring that culture and execution remain aligned even as the team expands.

Phil also describes how RepeatMD V3 marks the next phase of that philosophy in action. The platform’s new “automated revenue” model, featuring SkinDrop and AI treatment advisors, is designed to let clinics scale while doing less manual work and offering more personalized experiences. Rather than replacing the human element, the technology reinforces it—freeing teams to focus on relationships, creativity, and client success.

At its core, this episode is about transformation: the shift from reactive leadership to intentional design. Phil’s honesty about navigating uncertainty, hiring missteps, and maintaining standards in times of pressure provides a rare look at the emotional architecture of leadership. His story illustrates how vision, when paired with structure, can turn a company into a movement. For founders, operators, and creators alike, it’s a reminder that real growth begins with responsibility—and that the best systems are built to preserve humanity at scale.