This episode of the Society of Actuaries' Professional Development Edge podcast features Dave Dillon, Senior Vice President and Principal at Lewis & Ellis; entrepreneur and founder of Cost Plus Drugs, Mark Cuban; and Jon Forster, the SOA's Director of PD Learning and Content Design. Together, they explore entrepreneurship, artificial intelligence, and the evolving healthcare landscape. The conversations move from what it takes to be successful in business, the current healthcare landscape, and the state of AI in Actuarial work. Mark shares the origin and mission behind Cost Plus Drugs, underscoring the critical role of price transparency and trust in improving healthcare access and affordability. Listeners will gain practical insights and forward-looking perspectives relevant to actuaries, business leaders, and anyone interested in the future of healthcare and innovation. Contributors: Mark Cuban; Dave Dillon, FSA, FCA, MAAA; Jon Forster, ASA, MAAA