Sandro Kopp and Freeman White were once the archetype struggling artists - on the dole and living in a flat with 20 others.
The Wellingtonians shared a passion of capturing the human form in paint and later met another young aspiring painter named Matt Gauldie.
"There weren't that many people painting figuratively or painting paintings of people and that's what really made me want to meet Matt," Mr White said. "And also me and Sandro were at art school together, so it was about forming these bonds and creating a future in a way,"
While they have taken different paths, each is successful. Matt Gauldie is the New Zealand Army's official artist and has painted troops in Afghanistan - going from struggling artist to Captain Gauldie
"There was three months when I wasn't doing any art whatsoever," Mr Gauldie said. "I was doing basic training in Wairoru, going through the recruitment process like everybody does in the army, learning what else can you do, what else you got, who are you. Take away the art and artists, what are you made of. That was something very testing and trying for me."
Two years ago Mr White won the Adam National Portrait Award for his picture of a friend and playwright Ryan McFaddian, named Portrait of Hans.
"I've even tried to paint abstracts and paint things that I thought would be more accepted," he says. "And it would always come back to I'd be looking at these paintings and saying where are the figures? Where's the soul? Where's the personality in these paintings?"
Sandro Kopp has been on the move for two-and-a-half years. His work has been shown in New York, Los Angeles, and last year in the BP Portrait Awards at London's National Portrait Gallery.
"For me just to go 'well there's mine on the wall and down the wall is a Lucien Fuer' and having been lined up next to my heroes was very gratifying," he said.
And Mr Kopp proves you never know what can happen when you paint someone.
Mr Kopp was asked to sketch English actress Tilda Winton when she was starring in The Lion The Witch And The Wardrobe and they have been together ever since. They have a base in Scotland and support each other in their work.
"It's great having a partner who's also a artist who knows what it takes to make work," he says. "She's very supportive but at the same time she knows that I have to go off and do my own thing."
Painting portraits went into decline in the later part of last century, but now the painters say it is back in vogue.
All three painters have made people the focus of their creativity and expression and this week the trio have a show which opens in Wellington in what is a celebration of friendship and a shared passion.