"I want to help break the stigma that surrounds being a young mum or dad in New Zealand," Woolloff told the Herald.
"There is an awful lot of judgment put on you, when all you are really trying to do is your best for yourself and your family.
"Some of the teen parents I have met are doing a better job of it than some of the older mums and dads."
The first of the youngsters he is assisting - 18-year-old Wellington school student mum Zara Smith - will be sent on a 21-day Outward Bound course in July, which costs about $4500.
The pair met when Woolloff spoke at He Huarahi Tamariki Secondary School for young parents in Tawaher, where she is a fulltime student as well as being mum to 2-year-old son Tamatea.
Some of the teen parents I have met are doing a better job of it than some of the older mums and dads.
"Being a teen parent means you are probably a bit more mature and organised than your friends, so a leadership course is ideal for building on that," Woolloff said. "I did the same Outward Bound course last year and really felt it benefited me.
"It got me even more motivated and got me thinking it would be nice to do the same for others."
Smith is delighted to be the first to be chosen.
"This is a cool opportunity for me and the main object is to get me to a higher state of mind," she said. "The only thing I'm nervous about is being away from my son for three weeks."
Woolloff will soon start a degree course in marketing communications at Massey University in Wellington. He reckoned the past two years has been a steep learning curve.
When he found out he was going to be a dad he kept the news from his mother, Siggy Woolloff, who was herself pregnant with Noa's brother.
The babies were born only two days apart, with baby Jimmy Davidson 48 hours older than his niece Kyla.
Worried about stressing out his mother it took Woolloff three months to tell her that he too was a parent. He shares the care of his daughter with his ex-partner.
"The kids are just like brother and sister now, they love playing with each other," he said.
"But they can get pretty cheeky and mischievous...you have to keep your eyes on them at all times."