Stephen William Day was the hyperactive youngest of five children. He was brought up as an only child as his siblings had already left home when he came along. It was a “fabulous” but certainly not wealthy lower middle class upbringing in Nelson and his parents, a primary school teacher and a housewife, put a high value on education.

“Dad’s OE involved shooting Germans. World War II deprived him of an education,” Day says. “In hindsight, responding to that, I did too much [studying]. I should have been out there, doing it.”

Day was in his early 30s when he finished his third Victoria University degree — a Masters of Business Administration to follow a BA and a law degree.

By then he had endured years of wild entrepreneurial dreams that were never quite realised as he swung between mediocrity and outright failure.

He attempted mussel farming in the Marlborough Sounds around 1980 but this was a flop, as was his foray into residential property development in Wellington. He had some success with a tenpin bowling alley and a gig as a management consultant, but he was bored.

Then he and a mate set themselves up as diving instructors, doing the odd commercial salvage job. Day became a fireman to round out his working week.

He met his wife, “the long-suffering Karen”, when she signed up for one of his diving courses. “[Karen] needed a lot of extra training, yep,” he says.

Karen Day’s salary paid the bills for many years. She was a lab technician while her husband continued to study, fight fires and dabble in various ventures. Day says he lived on dreams while his wife, famously, made cups of tea for the bailiff.

The slow and steady, pay off your mortgage, save for retirement existence was never for them.

Day concedes entrepreneurs make unnerving life partners. Their blinkered determination can lead to “all sorts of suffering for family and friends”. Entrepreneurs are future focused, and failure fades into the past very quickly, he says. When confronted with failure, men and women like him don’t even have the good grace to feel bruised, to lament what could have been or take stock of the sacrifices others have made on their behalf; they’re too busy mortgaging their family home to chase the next whiff of potential.

“I’m partly guilty of that,” he says.

If those days were hard on Karen Day, she doesn’t seem to have any lingering ill will. In fact, she says she is thoroughly grateful to Day for the life they’ve shared for almost 30 years. She always had belief that, eventually, one of his ventures would come off.

“I think it’s pretty obvious to most people who meet him that he’s got something special.” Karen Day says entrepreneurs like her husband tend to be on the optimistic side of reality, while she is naturally more pessimistic. When failures did befall her husband’s ventures, the one advantage of being a pessimist kicked in: she wasn’t too disappointed.

While Bill Day may not be interested in identifying the obstacles to success on any given project, he’s now willing to listen to those who do. With age, his wife says, Day has become better at listening to those around him and seeing other points of view.

Karen Day may not feel she needs to be repaid for the years of uncertainty, but Bill Day obviously feels a debt of gratitude. At 52, he is keen to start spending more time with his wife and two sons, aged 18 and 21, and discover a life after Seaworks.