Kendall had coached during his competitive career, so the transition to doing it full-time was straightforward. His first gig was at the 1996 Atlanta Games.
"I coached Barbara and Aaron [McIntosh] for that Olympics and then I started coaching other countries. I've been doing it ever since."
While he loves coaching, Kendall says he's getting weary of living out of a suitcase.
"I tried to get out of coaching after the last Olympics because of the birth of my son [but] it didn't quite work out the way I needed it to, so I [went] back to coaching to prop up the bank account and feed the family.
"I think it's harder for my wife. I've got a five-year-old daughter as well and it's been very difficult."
Kendall has spent most of his life in sailing. As children, he and Barbara spent their free time on the family keel boat and competing at the Bucklands Beach and Kohimarama yacht clubs.
"Our parents were very supportive of our sport," he says. "They didn't have a lot of money but helped us out in every way they could. Barbara and I were always competitive against each other."
The siblings were cruelly denied a moment of family glory at the Barcelona Games thanks to gear failure, which cut short Kendall's run for a third-straight Olympic medal.
In the third race of a seven-race series, the fin on the board Kendall had been supplied with broke due to a manufacturing error. At that time, if you were unable to finish a race because of gear failure, you earned no points from that race.
Kendall immediately appealed but the decision was confirmed as he came ashore after his final race. The docked points meant he finished just outside the medals.
"That was pretty crushing - to know I'd finished fourth instead of [winning] a medal, which I should have had.
"Within minutes after that, Barbara came ashore having just won the gold medal. It was pretty hard to feel happy for her, which was horrible. It was just a really hard moment."
He managed to put the incident behind him by lobbying successfully for a rule change and went on to win the world championships in Japan the following year.
Kendall has lived a remarkable life but says he's now reached the point where he's starting to crave something a little more ordinary.
"I'm hoping I can find a way to earn a living where I can spend more time with my family," he says. "It sounds exotic to be travelling the world, coaching all over the place and seeing all these amazing things but, to be honest, I'd rather just be in New Zealand."
