He helped his father every day before school and landed his first sharemilking job in Matamata at the age of 18.
He set a farm production record in his first year, a feat he repeated at every farm he bought.
"I think it was what I'd learnt from my father. He was a very good farmer. It's basically about good grass management and looking after your animals."
At age of 21 he bought his first farm at Morrinsville; he sold a later farm at Te Aroha after a marriage break-up and moved to Northland because it was the only place he could afford to start again.
He was a reluctant Northlander at first, believing it wasn't a great place for farming, until he spotted a Dargaville property that had everything he wanted.
He bought another three farms at Dargaville before buying Ngatitara, south of Kaikohe, which became the core of his Mangakahia Rd farms. From 2006 onwards he started buying up neighbouring farms and converting them to dairy, eventually owning 10 farms stretching more than 40km. At the peak of their farming empire the Pinnys also owned or leased farms at Kai Iwi Lakes, Moerewa, Taupo Bay, Kerikeri and Purerua Peninsula.
They had 65 staff, 15,000 head of beef and dairy cattle, and produced 20 million litres of milk a year.
However, running so many farms over a large area turned out to be "a hell of a mission".
They sold some off and concentrated on the Mangakahia Rd farms with a staff of 36, some of whom stayed with the Pinnys as long as 10 years.
"The last crew I had were just fantastic. I can't speak highly enough of them," he said.
The couple decided to sell up three or four years ago.
"I felt like I'd done enough in the farming world, and there were other things I wanted to do. Music is one of them."
Mr Pinny's farm career was unusual in that he tried to combine it with singing and playing guitar.
He landed a recording contract and at one stage he was playing six nights a week in Auckland while farming in the Waikato by day. He has now set up his own recording studio at home on the Purerua Peninsula. His earliest recordings have been remastered and are about to be released on iTunes.
"So I've almost gone full circle," he said.
He currently performs with Bootleg, a rock/blues band due on stage at the upcoming Ocean and Orchard Festival in Kerikeri.
Mrs Pinny was using her newfound free time to focus on a business degree while he was enjoying not hearing his phone ring every five minutes.
"I'll probably go fishing, that sort of stuff. I'll be having fun and learning to enjoy the Bay of Islands - and catching up on family time," he said.
