"All these people talking about me like they knew my whole life. Saying my parents had done a shit job... It was just really frustrating."
But Woolloff proved everyone wrong. The teenager now travels the country sharing his story with other young people, and runs a non-profit business, Increase Clothing NZ, to support other teen parents.
The business raises money to send young parents on adventure and leadership-based courses such as Outward Bound, which Woolloff recommends for all.
He has even found himself sharing a lunch with the President of Germany and a small group of other entrepreneurial young people.
Woolloff also works for a charity called Inspiring Stories, which is focused on young people and encouraging leadership and innovation.
He had been enrolled to do a marketing communications degree at university this year, but pulled out two weeks before the course began.
"I don't really want to commit to something and invest tens of thousands of dollars and four years of my life into something I'm not too sure I want to do for the rest of my life," he said.
"I just don't believe in doing something that doesn't make you happy. I think you've got to do what sets your heart on fire, as cheesy as that sounds."
What sets Woolloff's heart on fire is supporting other young people and young parents. He hopes to set up workshops for young fathers like himself, and loves the opportunity to share his journey with youth around the country.
He has done a Ted talk, toured New Zealand with World Vision, and spoken to 1300 young people at Festival for the Future.
"It's not about me advocating for teen pregnancy. It's more about how do we move forward as a society and not neglect others because of the situation that they're in."
Kyla turns 3 in March, and is "absolutely amazing".
The toddler, who is learning "the art of sulking", has made her father careful about what he invests his time in.
"I think she's impacted my life in every way. I can't remember not being a parent now, I think that's the same with most parents. You don't remember your life before that.
"I guess it's like, whatever you do there's always the bigger picture here now."