In this episode, Jack sits down with Diego Andres of Smart Boston for a conversation centered on money, mindset, and the power of human connection. Diego breaks down how Smart Boston is using street interviews and real conversations to understand how Gen Z thinks about wealth, relationships, confidence, and personal responsibility. He shares why he believes proximity, curiosity, and the willingness to feel uncomfortable matter more than resumes, credentials, or trying to look polished too early. The episode also gets personal, as Diego opens up about depression, loneliness, early entrepreneurial losses, and the hard lessons that shaped his perspective on leadership and success. It is a sharp, high-energy conversation about rejection, self-awareness, and what it actually takes to build a bigger life from the inside out.

SmartBoston
Diego Andres

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Host: Jack Moran

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