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Growing up in Maui, Jesse Richman learned to fly a kite in the ocean. At age 9 he was harnessing the wind to pull him across waves while strapped to a board. He won his first world kiteboarding title at 16. Now 24, Mr. Richman is pushing the boundaries of his sport. “My focus is bigger waves and bigger air,” he says.

Mr. Richman performs wakeboard-like tricks 50 feet in the air and uses his kite to ride a surfboard on Pe’ahi, or Jaws, a wave on Maui renowned for its 30-plus-foot faces. His daring stunts earned him first…