Mr Dempster grew up in Flag Swamp.
He was the first of the fifth generation of Dempsters in the area to be a pupil at Flag Swamp School.
Then he went around the world, did a bit of everything, and became a full-time artist.
Now he is back with his family living in rural Flag Swamp, and the sixth generation of the Dempsters is in the area.
Mr Dempster (44) has set up a studio at the Flag Swamp house he shares with his partner and son, and is keen to get it all shipshape with displays of his work.
It is not Paris or London, but he said he was happy to be home and enjoying the area.
"I’ve always wanted to get back here. Always wanted to get back and show my paintings."
After Flag Swamp School he did a bit of correspondence school and then was a boarder at St Kevin’s College.
He then headed to the University of Otago, where he "did a bit of everything".
He dabbled in some history papers and went to teachers’ college before he headed to Victoria University of Wellington, where he met his partner Simon Poynter.
He studied for an MA in art history, focusing his studies on how the production in film had contributed to education.
But his itch for art never waned. He had begun working at Roslyn Gallery in Dunedin while studying at Otago.
During this time he was working on his own art, developing a style and working through it.
"I never made any money out of it but it was always something I wanted to do.
"There was a lot of pressure. A lot of that I put on myself.
"I always remember my grandfather telling me ‘you’ll never make any money out of that’."
He kept working on it and the couple headed to the United Kingdom in 2007.
With nothing solid work-wise, he joined an art collective in Herne Bay, Kent, and worked full-time on his painting.
"It was nerve-racking. You are putting yourself out there. Showing what you are about.
"You’ve really got [to] have some stamina and stick at it. Believe what you are doing is right."
Now, many years later, it is only getting better.
"As long as you are getting enjoyment out of it and bringing some pleasure to other people then that is cool.
"Just recently I was talking to someone who said they have been following me for the last 10 years.
"So yeah that does give you some satisfaction - a bit of a buzz."
His painting has evolved.
When he first lived in Europe he painted a mixture of urban and rural scenes from places he had visited. He termed them naive contemporary.
The couple came back to New Zealand about 10 years ago and lived in Dunedin for a good while, where Mr Dempster continued to develop his art.
He is now focused on cubist geometry - concentrating on colours and patterns - and has an emphasis on housing.
His partner was the main breadwinner but year on year, the art bank balance was increasing as Mr Dempster was selling more.
Paintings were sold through galleries or big art shows, and a few were held in major centres throughout the year.
He tried to manage a work day of 9am-3pm but it was not always easy.
His son Gethin (4) was a busy boy and would soon start school, though he would unfortunately not be the sixth generation to go to Flag Swamp School as it had closed down.
There was also a studio to get right at the Flag Swamp property.
The property they live on has a main house and a smaller house which used to be a bed and breakfast.
This would be converted to an art studio, where he would work and sell paintings.
Signage would go in and he would set it out to make it available for small numbers of people at a time.
Obviously foot traffic would not be large, but attracting people was more about word of mouth, he said.
