Jon Brady’s career has taken him from teaching aerobics at a YMCA in New Zealand, to building a professional rugby club from scratch, to leading one of the most iconic premium health clubs in the United States as President of Midtown Athletic. In this conversation, Jon joins Andy to unpack how sport, education, and community shaped his philosophy on leadership and wellness.

He shares how he helped transform Midtown from a mid-market tennis and fitness business into a high-end, multi dimensional social wellness club, why “better than yesterday” is a core value, and how his team uses machine learning and data to keep members consistent without feeling creepy. Jon also goes deep on vulnerability based leadership, culture as a daily practice, and why the future of fitness is less about aesthetics and more about how people feel, connect, and belong.

If you lead teams, work in fitness or hospitality, or care about building real community in a lonely world, this episode will resonate.