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In the latest episode of the ABWilson Heart of the Matter podcast, I sit down with A.J. Vassar, a self-proclaimed underdog whose path from homelessness to purpose is fueled by ambition, resilience and a deep sense of compassion. From the moment A.J. begins sharing his story, his authenticity and drive are unmistakable.

He takes us through his early years growing up in a large family, where competition for attention and resources taught him valuable lessons about ambition, grit and finding his own path forward.

Despite facing challenges that might have discouraged many, AJ.embraced his identity as a late bloomer, using it as motivation to exceed expectations. His dedication to personal growth was evident even in his college days, where he played football at Southeast Missouri State, a formative experience that instilled discipline and a love for hard work.

One of the most striking chapters of A.J.’s story is his spontaneous move to Medellín, Colombia, a city he had never visited. Drawn to its energy and known as the city of eternal spring, Medellín became a backdrop for both personal transformation and a renewed sense of freedom. Yet A.J.’s path wasn’t without hardship. At one point, he found himself homeless and sleeping in his car. Rather than give in to despair, he turned this experience into the foundation of a mission: to give away cars to others in need.

A.J. explains how he sources these vehicles and why the act of giving them away holds such deep personal meaning. It's just one of the many bold moves in his life, including a remarkable 40-day water fast that tested him physically, mentally and spiritually. That experience, along with other challenging feats like walking long distances for charity, underscores his belief in the power of doing hard things to unlock personal growth.

Discipline remains a cornerstone of A.J.’s lifestyle. He shares his go-to self-care practices, including daily meditation and cold showers, which help him stay grounded and focused. These habits support his latest ventures, including an exciting foray into government contracting, an opportunity made even more meaningful through mentorship within his own family.

Throughout the conversation, A.J. returns to a central theme: living life on your own terms. He’s passionate about helping others design a vacation lifestyle, one where work and life blend with purpose, joy and freedom. For those curious about his mindset, A.J. recommends several books that have shaped his outlook, including Rich Dad Poor Dad, As a Man Thinketh, and the Book of Proverbs.

As the episode wraps, A.J. leaves listeners with a powerful reminder about the importance of connection, community and having the courage to take leaps of faith. His story is a testament to what’s possible when you choose to bet on yourself and live with intention and heart.

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