What does military leadership really teach you about success after the uniform comes off? In this episode of the Adapt and Overcome Podcast, host Tommy Hardaway sits down with Army veteran and investor Jon Kerr to explore how discipline, structure, and leadership learned in the military can directly translate into business and investing success.

Jon shares his journey from serving as an Army captain to becoming an investor in multiple companies. He explains why he proudly calls himself an investor instead of an entrepreneur, how he evaluates businesses before putting his money to work, and why leadership teams matter more than ideas alone. Throughout the conversation, Jon breaks down the importance of finding differentiated businesses, owning equity, and taking a long-term view when building multiple income streams.

The conversation also dives deep into how military culture shaped Jon’s approach to leadership. From understanding accountability to helping teams succeed, Jon explains how lessons from drill sergeants and commanders still guide how he supports the companies he invests in today. He also offers honest advice for people looking to create income beyond a traditional 9-to-5 and why there is no such thing as “easy money.”

This episode is packed with practical insights for veterans, entrepreneurs, and anyone interested in investing, leadership, or building financial independence.

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