This conversation explores the evolution of stand up paddling (SUP), from its explosive rise in popularity in the mid-2000s to its current status. The speakers reflect on their personal experiences with the sport, the influence of pioneers like Laird Hamilton, and the challenges faced by athletes in maintaining careers in SUP. They discuss the evolution of paddle boards, the transition to foiling, and the changing attitudes towards different water sports. Kai shares his journey in stand up paddle racing, detailing his pursuit of breaking the world record in the Molokai to Oahu race, the challenges he faced, and the iconic events that shaped his career. He discusses the importance of fitness, mental resilience, and the competitive nature of the sport, particularly during the Sunset Beach event and the Battle of the Paddle. They reflect on the drama and excitement of past competitions, the challenges faced by the sport today, and the importance of safety in big wave surfing. The discussion also touches on innovative ideas for future SUP events, emphasizing the need for accessibility and fun in the sport.