In this conversation, Dr. Dan welcomes David Goldring, Chairman and CEO of Overseas Military Sales Corporation, stand-up comedian, speaker, and author of the USA Today bestselling book Stand-Up and Lead. David explains why commanding a comedy stage and leading an organization rest on the same fundamentals: authenticity, vulnerability, empathy, presence, adaptability, and real connection with the people in the room. A comedian’s job is to bring a room full of very different people together around one shared experience. David came to see a leader’s job the same way, as uniting people around a common vision, and the realization changed how he leads.

David opens up about the hardest chapter of his life, when his first wife developed dementia at 42 and later passed away. Raising two young children while running his company, he stopped pretending to have everything under control, told his team what he was facing, and asked for their help. The decision became a defining moment in his leadership. From there, David and Dr. Dan talk about the fear of failure and rejection, why decades of stand-up taught David to treat a bombed joke as information instead of a verdict on his worth, and why the so-called soft skills of empathy, active listening, and authenticity are the hardest ones to master. They close with a call for presence in a distracted world and a reminder for every leader: sometimes the strongest words are “I don’t know. I need your help. Let’s figure it out together.”