His maternal grandfather survived being shot at Gallipoli before marrying a nurse from the Australian Outback who was caring for Kiwi soldiers in Rotorua.
His other grandfather ran away from home at an early age, joined the British Merchant Navy at age 14, and arrived in New Zealand after his ship was dismasted in the Tasman Sea. His mother, aged 93, lives in Auckland.
"They were all very formative with their values and work ethic."
Mr Stanway hunted deer to pay his way through Massey University. He was a 20-year-old student when he married his wife Jude, who was 19. The couple now have four daughters, all aged in their 30s and 40s, and eight grandchildren.
After university, Mr Stanway went farming, his Bachelor of Science degree making him "the Coromandel's most qualified shepherd". He also worked in a freezing works in Feilding for six months.
His break into business came when he joined pharmaceutical company Pfizer, where he worked his way up to become national sales manager for the animal health division. He was still only in his late 20s.
"Those were great times," he says.
Mr Stanway resigned from Pfizer and bought a cafe on Ponsonby Rd, Auckland, to free up enough time for him to pursue his dream of owning a farm by age 35.
He and Jude listed all of the things they wanted in life and found that the Bay of Plenty ticked all the right boxes. He went to an auction in Rotorua and bought a farm called Sun Valley Station.
It was 1984, the year of Rogernomics. Interest rates were up around 24 per cent. Inflation was in double figures. But the Stanways survived.
After 10 years they sold the farm and bought a 4ha lifestyle block on the western shores of Lake Rotorua, where they "did some high-risk forestry stuff".
Another career change saw him working as Rotorua District Council's economic development manager for seven years.
His next big move brought him to the Western Bay. In 2002, Mr Stanway became chief executive of Priority One, a body established by local authorities and businesses which aims to help grow the region's economy.
And then, in 2006, he joined Realty Group.
"It was the last year of the boom times, before the global financial crisis. We invested in people, and when the upturn came two years ago we were in great shape to run with that."
Mr Stanway describes the current market surge as "quite phenomenal", but is confident that the Bay of Plenty market will level off, rather than fall significantly, because it is supported by growth and a healthy local economy.
Mr Stanway will retire at the end of March, but is likely to remain busy. He is president of the Tauranga Golf Club, owns a storage business and is involved with a Maori trust.
He still enjoys hunting and is a keen swimmer, but "has to be careful now" after having had spinal surgery and "shearing my collarbone off while boogie-boarding".
Still, his eyes light up with talk of his Oceanbeach Rd home, which looks out over the dunes to the beach.
"I love the sea," Mr Stanway says.
"That's where we've always wanted to be."
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On the Bay's buoyant property market:
"It's been quite phenomenal growth, and I think it's too easy to pass it off as the Auckland effect.
"Quite frankly, I think what's attracting people are factors like the climate, but there's also some real growth in the commercial sector. So we hear about a property boom, but what we're seeing is far more sustainable."
On the changes in the industry:
"I believe there is a high value in dealing with people face to face, and I don't think that's altered. But there have been technological advances - buyers can have a virtual tour of a property now, access LINZ reports, files, Google Earth ... Before, a real estate agent was the font of all knowledge, but now they are often the last point of contact."
On success in business:
"I've always had a pretty good idea of what needs to be done and how it can be achieved. The main difference between (successful and unsuccessful) businesses is the people and the culture. Dealing with people eyeball to eyeball is a huge part of business success."
On life choices:
"If you're not having fun, go and do something else."