"That's when I came up with the idea - let's just start our own walk here in Auckland instead," he said.
"The first year it was just an idea of raising a bit of money and having a bit of fun but then everyone just started taking it a bit too seriously."
In 2012 the event raised $8,000 and 12 months later it raised $16,000.
"One of the fundamental issues I've found with some charity events is you don't really know where the money's going, so I thought, well, why don't we start a charity where you can see where the money is spent, where you can actually spend it locally where it's needed?"
Projects have included life-skills programmes at Randwick Park School in Manurewa and Glenn Innes School; sending dozens of kids on a sports camp; planting hundreds of trees and setting up Garden to Table at Sir Edmund Hillary Collegiate in Otara.
The latter involves creating vegetable gardens that are maintained by the students, who then use the produce to cook nutritious meals.
Papatoetoe West Primary School principal Diana Tregoweth said the programme would give her students valuable skills for life.
"I've seen it work really well at other schools so I'm really excited about the programme," Tregoweth said.
"We're just so grateful that we've been one of the lucky schools that have been picked."
The Head2Head Walk begins in Awhitu at the Manukau Heads on Saturday, November 8.
So far, 10 teams of five have signed up, but Dickson expected more to enter as the start date draws closer.
The route is split into five legs, with each team member walking about 25km.