Kai Lenny is one of the best and most daring surfers in the world. In the water, he displays an awe-inspiring sense of freedom: He can do whatever he wants, go wherever he wants. His approach to big wave surf is characterized by creative lines of attack and aerial maneuvers previously only seen on snowboard slopes and skate ramps. Thanks to his skill as not just the world’s most exciting surfer, but also currently the world’s greatest waterman, with guts and a winning personality to boot, he’s a budding media juggernaut. That translates to countless viral videos, over a million Instagram followers, a reality web series Life of Kai, and a breakout spot on HBO’s docu-series 100 Foot Wave.

If there’s a storm system creating massive waves described as “liquid napalm” in some corner of the world? He’s probably there. But these days, Lenny is looking over his shoulder more than usual. The waves still call, his greatness continues to peak, but he’s got two new projects at home that are making him think on the future, about what brought him here: his twin one-year-old daughters Willa and Senna. For our annual Outside Issue, Fatherly contributing editor Alex French spoke to Lenny and his extended family, not to mention some legendary surfers, about Kai’s career and new role as a dad, taking risks and instilling in kids a love of the water.