My Longest Relationship: Three Decades of Friendship & Evolution (with Jaime O'Brien)

Host Kris Saim celebrates a friendship that has endured and evolved for nearly three decades with his "great pal," Jaime O'Brien. Their story is a powerful exploration of loyalty and meaningful reconnection. Kris and Jaime discuss how their paths continually wove back together: from Kris being Jaime’s empowering boss to Kris becoming Jaime's realtor , and now, as peers leading a professional Mastermind group. They reflect on wild memories—from covering the "NASCAR for bass fishermen" FLW tour to chaotic late-night taxi rides and an unexpected trip to the ER. The core lesson is clear: Time doesn't have to dilute friendship; it can make it stronger. Jaime urges listeners: "Don't put off reconnecting with somebody... it's never too late to just reconnect". This episode is proof that the best relationships keep showing up, no matter how uncomfortable the roads become.