This year he competed at the elite Coast to Coast in a two-day tandem event with school mate Dylan Sherwood but now intends to accomplish goals that will lead him to the path as an individual who will hopefully blossom into a professional.
"The plan in life is to get up there [elite level] and the first step is to do the Coast to Coast in one day," he says, finding inspiration from this year's Coast champion, Sam Clark, of Whakatane.
He hastens to add Abby Macredie, also of THS, is embarking on that path after competing in the two-day category.
Webb suspects his two elder brothers, George, 20, a crosscountry runner, and Angus, 19, a former Bay age-group hockey rep, "have got the brains in the family" while the academic genes lay dormant in his biological blueprint.
His brothers are pursuing engineering degrees at Canterbury and Auckland universities, respectively, since leaving THS.
"I haven't thought of anything apart from sport," says the year 12 pupil, who hopes to do something in physical education at Otago University as insurance cover in case his multisport dream dissipates.
X and Y chromosomes aside, the teenager has no doubts the home farming environment of his parents, Linda Ross and Graham Webb, have helped mould his mental fortitude to try to tame the wild.
In Rotorua, he dominated the kayak leg and was first out of the water, something he attributes to his parents' no-choice edict for all three boys to come to grips with water.
"We were all made to swim because they wanted us to be safe in water," he says but feels he needs to work on his running.
From the age of 4 he learned how to ride a motorbike and that gave him the licence to help muster sheep and cattle.
The following initiation was docking and dipping of livestock, something he still helps out with during holidays or when time permits from the demands of school work.
But it's the little things that he did subconsciously growing up in the farm that come in handy in handy in his adventure races.
"You know, you learn to tie a knot and things like that."
"Bush bashing [creating treks] is not big in Coast to Coast" but it has helped him heaps since he started adventure racing through school three years ago under the guidance of teachers Pauline Edwards and Phil Dooney.
He used to engage in other codes, such as hockey, tennis, football, but there was something "cool" about the adventure racing promotion that appealed as a good way to keep fit.
"I still do other sport but this [multisport] has just taken over. This sport is about doing things that average people can't do," he says, relishing the thought of traversing exotic and challenging terrain across outback New Zealand.
"There's way more adventure and, in most races, the worst thing about doing it is the body is aching and all you're thinking about is going to bed but then straight after crossing the line you instantly want to go back to doing more races.
"I just don't get that feeling with other sport."
Needless to say his parents delight in watching him compete in pursuits that get him off the couch although the impending trips in the wee hours of the morning to venues for training and competing over the years did have the adults wondering.
"It also costs a lot of money ... but I've got my driving licence now so they don't have to get me out at 7 o'clock in the mornings," he says with a grin.
Dooney helped hone his paddling skills in the first year before Edwards took over half way through the year, urging him to "never stop, go hard".
"She yells quite loudly so I'll be like running in the bush and I can hear. She's quite hard and doesn't take any excuses."
Webb finds multisport is about taking ownership because when something goes wrong it isn't anyone else's fault.
The individual Bay senior boys' triathlon champion last year, Webb says his school is the platform with participant numbers growing and the year 13s gearing for the full one-day event.
"Everything happens from school. We get our finding there, we use its name to obtain sponsorship for the nine of us this year and training with the teachers is another big part of it."