The iconic and innovative Pipeline master has never been a man of wind sports. Kai Lenny enjoys surfing, stand-up paddleboarding, windsurfing and even kitesurfing, so he invite O'Brien to a waterman's day.

Maui was the right place for Jamie O'Brien first windsurfing experience. The baptism got underway in windy conditions, but before sailing time, both riders went out for a SUP train.

Soon after, Jamie O'Brien was laughing about the long windsurf fin, the need for an harness, the sail and the mast. What's this for? Kai wanted to help, but it wouldn't be easy.

In the first few seconds of tandem windsurfing, Jamie falls. One, two, three, several times. Minutes later, they were both sailing well, always together, and under Lenny's surveillance. Not bad.

In the dying seconds of the windsurfing experience, Kai decides to sail as fast as he can towards the beach, leaving poor old Jamie alone in a sand crash accident. Impressive stunt. Will Jamie O'Brien ever get back to windsurfing?