41. AI, Marriage, and Empowerment in Work: Bobbie Caldwell on 34 Years of Balance

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In this episode of Joy of the Hang, we sit down with Bobbie Caldwell—a business leader, husband, father of four, and lifelong learner—for a powerful conversation about relationships, vulnerability, and what it means to adapt, commit, and give back.  

We explore how artificial intelligence is reshaping the way we work, study, and communicate—and why embracing change doesn’t mean abandoning core values. Bobbie shares insights into building a lasting relationships through vulnerability while staying curious in the face of evolving technology. He explains how that same mindset helped him cultivate a 34-year marriage, raise four children, and maintain grounding in service to his community.  

His philosophy? Work hard, play hard—and lead with T.L.C. That’s Think, Laugh, and… Can you guess what 'C' stands for? You’ll have to tune in to find out!  

This episode is a thoughtful mix of empowerment, innovation, integrity, and a little wisdom from the home front.

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