He wasn't so certain at 1pm and flopped down on a purple blanket for his five minute break, while a member of his support team massaged his aching legs.
"I feel like I've got knots in my legs and I probably look like a ghost," he said.
Organiser and team support member Kate Shellard had been supporting her friend on and off for 16 hours.
"We're all tired, but we want him to keep going - we don't want him to give up. He's doing so well," she said.
But as the crowds grew, so did the support and the atmosphere of Taradale Park was turned upside down. Music was pumping, horns tooting and so began the New Zealand national anthem for probably the fifth or sixth time that day.
The fatigue began to leave the teenager's face as more people gathered around him, cheering in support as the countdown began - 2.15 struck the clock and he'd done it.
O'Brien's bizarre world record choice has reached corners of the earth, with support coming from Ireland, Scotland and Canada.
"He's certainly putting Taradale on the map," one supporter said.
His team of at least 20 people have been working in four hour shifts, monitoring O'Brien all times as well as being filming him on camera. No one is allowed to push him and he has to keep moving at all times.
Although they're sleepy eyed, they remain positive and offer strong words of encouragement as he pushes on to reach the ultimate goal of 40 hours.