It was a revolutionary move in a competition constantly trying to push the barriers of the sport, and a big part of Team NZ's winning campaign.
"I knew it long before I knew about track cycling. It was just a roundabout way of getting here," van Velthooven recalls of his venture into sailing.
Part of the team to bring the Auld Mug back to Auckland, van Velthooven was determined to be a part of the defence. But with the cycling stations scrapped in the AC75 model to be sailed in Auckland in 2021, if he was going to be a part of the team again he had to learn the more conventional way of working the pedestals.
"I had to get out on the water and go sailing, get on the handles and do some training. It was a solid 18 months or two years of training to prove myself on the trial day," he says.
"The on-water grinding is very aerobic. You've got to be heavy-duty as well, so it's a mix of doing gym work and spinning handles and building that aerobic base. When we have to push the boat for over an hour of racing, it's going to hurt so I wanted to get across that barrier, or that hurdle."
With his goal set, van Velthooven immersed himself in the sailing world. Taking a job with local boat manufacturer Southern Spars, he worked at getting his head around the lingo and getting out on the water as much as possible to prepare for the team trials in early 2019.
"You've just got to put in the work, really. There's no skill set involved as such, the skills needed are at the back of the boat where people are driving, so all I really had to do was turn handles for a couple of years and build up the muscle memory."
The work was well worth putting in when trials came around, as team hopefuls were put through a series of power and endurance tests Team NZ chief executive Grant Dalton described as "brutal". As van Velthooven recalls, the physical demand of the trails was "the worst of the worst that you could imagine".
"It was a necessary evil to find out who will be able to handle it on the water come 2021," he says. "A lot of sports train for one day … but the America's Cup is over a couple of weeks and there's all the build-up work as well that you have to do. We've got to turn handles that whole time.
"Being a robust athlete that can handle the day in, day out s*** that goes along with the sport, that's necessary the most, and being able to handle a full regatta without being injured is another thing that's looked at. So it's not just putting up the best numbers on one day, it's putting out a lot of really good numbers over a long time."
Late last month, the 30-year-old's place in the 14-man crew tasked with defending the Auld Mug was confirmed.
It's an impressive feat for an athlete who just three years ago was a full-time cyclist competing for New Zealand at the Olympic Games in Rio de Janeiro.
"I think I was finished after Rio," he said of his track cycling career. "There was a little chance if we didn't win in Bermuda that I might have gone back as an endurance rider having quite a large endurance base from cycling on the boat, but you can't not want to help the team defend the cup in Auckland. That drive was there and the drive to defend the Cup with the team was the biggest thing really.
"The key word is a lot of training," he says of his successful transition into sailing. "I wasn't naturally gifted, I just trained a s*** load really."
With his spot in the team confirmed, van Velthooven isn't getting too far ahead of himself and knows there's plenty of work still to be done before the 2021 regatta. The first step is getting their first test boat on the water.
"The America's Cup is always about mystery and development and speed; I think this boat covers all of that.
"It's going to be a helluva time when all the team's boats are here in Auckland sailing around and it'll be even more exciting when we line up come 2021. The boats are pretty impressive and all teams are looking forward to getting out on them."
Parts for the vessel have been arriving in Auckland over the past few weeks and while the boat is in the process of being constructed, the team has been working on simulators.
Getting out on the water is a top priority for the team, who will look to spend as much time as possible on the water once the vessel is ready to go. Van Velthooven says the team is tentatively looking at a launch date in August or September.
"It's pretty broad," he said of the timeline. "Anything can change in this sport and with this event. I think everything's pointing to the end of august for a launch, but who knows. It could get pushed out in a half a second."
Team New Zealand's crew for 36th America's Cup: Blair Tuke, Peter Burling, Glenn Ashby, Ray Davies, Simon van Velthooven, Josh Junior, Joe Sullivan, Andy Maloney, Carlo Huisman, Guy Endean, Louis Sinclair, Steven Ferguson, Marcus Hansen and Marius van der Pol.