Lil Len

Kai Lenny

Anything that involves the ocean, I’m game!

Kai Lenny paddling through the waves
© Brian Bielmann/Red Bull Content Pool

Hi, my name is Kai Lenny. My discipline is surfing big wave, free surfing windsurfing, wave kitesurfing freestyle. My friends call me Lil Len. I was born on 8 October 1992 in Maui, Hawaii, USA. My special talent is having lots of fun. My philosophy of life is live life to the fullest, have fun, never give up and be the best you can be. My favourite food is burritos.


Kai Lenny is one of the world’s most complete watermen. Be it kiteboarding, windsurfing, stand-up paddleboarding, big-wave surfing, or anything else in the water, Kai does it, and does it well.

Growing up on the swell-rich northern shore of Maui as the son of ocean enthusiasts, he was surfing by the time he was five and was behind a kite before he was 10.

He’s had an impressive lineup of mentors: windsurfing legend Robby Naish and big-wave veterans Laird Hamilton and Dave Kalama have been some of Kai’s most dynamic teachers.

He’s done the gruelling 32-mile Molokai to Oahu paddle many times, was a veteran on the Professional Windsurfing Association World Wave Tour, has been runner-up at the Kite Surf Pro World Championships, and he’s won the SUP World Title six times and counting.

Yet through it all, he remains modest and humble. “All of my sports are surfing based,” says Kai. “My favourite thing in the world is riding a wave, so as long as I’m riding a wave, I’m happy.”

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Career Highlights

  1. 2016
    1. 2nd Place: Hong Kong International SUP Championships

      Hong Kong, China

  2. 2016
    1. 3rd Place: Stand Up World Series Victoria Cup

      Zushi, Japan

  3. 2015
    1. 2nd Place: Moloka’i-2-O’ahu Paddleboard World Championships

      Oahu, Hawaii, USA

    2. 1st Place: Sunset Beach SUP Pro

      Oahu, Hawaii, USA

    3. 1st Place: Da Hui Backdoor Shootout - Pipeline

      Oahu, Hawaii, USA

  4. 2014
    1. 1st Place Overall: Standup World Cup Series Finals

      Long Distance Race

      Oahu, Hawaii

  5. 2013
    1. SUP Overall World Champion

      As well as SUP Race World Champion and SUP Wave World Champion

    2. Sunset Beach Pro Champion

      Kai also won the 2010 and 2011 editions of the tournament