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Today, Damien Grant features in NBR for his role as principal of Waterstone Insolvency, unwinding the mess at companies that have gone off the rails – or in his role as a conservative political commentator. He's an entrepreneur (Waterstone is just one of several business interests), a family man and someone with a reputation for being brutally honest.
Things were racier in his youth.
At age 26, Grant was sentenced to 30 months’ jail for his part in a multi-million-dollar share-dealing scam.
He was living the high life, spending money on his lifestyle and travel, and "working" when he wanted to.
"It’s intellectually very interesting because you’re operating against the state," he says now, of the lifestyle back then.
"There are people who want to stop you doing what you’re doing. Once you beat the system and get some money out of it, there is an arrogance and a hubris that comes with that.
“Here I am in my early 20s, and the government and state have set up all these things – and I managed to beat it. Aren’t I clever."
Things began to unravel when he and some cohorts converted some of their ill-gotten scrip to gold, then tried to smuggle the ingots out of the country. They got caught.
Initially, he made bail. Then, panicking, he went on the run for a month, hiding with friends down the line. But he found the freedom to be illusory; he had little freedom of choice or action as he tried to "go off the reservation."
When he returned to Auckland, this time as a known flight risk, he knew his High Court hearing would not go well (read documents relating to the case and its aftermath here and here) – and when the judge adjourned the session for lunch, he walked over the road to a cafe and bought three cigarette packets (the maximum he could take to prison).
He can't remember who else was in the van, only the fear.
His purchase was indeed prescient. The judge ordered he be held on remand, and he was bundled into a police van and taken to Mt Eden Prison, where he would stay for the weeks until his sentencing.
Grant's first three months, at the gothic Mt Eden then, post-sentencing, Waikeria – the minimum to high-security 650-prisoner jail south of Hamilton (that has recently been at the centre of the "mega prison" debate) – were the hardest.
There were only three or four other white faces, he says.
He had to share a cell, and witnessed some brutal scenes.
At one point he sat playing chess with a fellow inmate as he listened to the screams from a known sex offender being beaten in a toilet block "and beaten hard." Guards arrived and the victim was segregated but it was a terrifying reminder of "just how Lord of the Flies-vulnerable you were if the mood of that group of people went against you," he says.
He tried to keep to himself but it wasn't an option.
He learned that to survive, you had to stand up for yourself. To gain respect, you had to fight back, even if you lost.
"If somebody wants to fight you, you have to engage," he says.
Grant himself survived on his wits. He developed a higher-brow defence mechanism, revolving around verbally engaging with other prisoners, forming links by asking them the old prison-film standby, "what are you in for?"
He recounts, "Oddly enough some of the harder guys, the more senior guys, once they were confident in talking to me, they were quite interesting — senior gang guys. Junior guys would talk about selling drugs, [and] the senior guys would talk about the commercialisation — how they ran their dubious criminal empires. I got to know some of those guys and formed a good relationship."
He also bonded with other inmates by accepting an invite to play "Crash," a bone-crunching version of rugby played on hard asphalt. It sounds unforgiving but Grant says he actually enjoyed it because it was the only opportunity for physical contact.
He read books, often many times overs. He bought cigarettes, which he had to ration to three or four a day. Mainly, he got spectacularly bored.
Move to the volcanic plateau
Things got easier when Grant was moved to Tongariro/Rangipo Prison, the low-to-medium security prison-farm at Turangi, where he would spend the rest of his sentence (which, in the end, was 13 months, plus his time on remand).
He got his own room and found that, "if you stayed within the rules, it was a relatively easy experience." He cut down trees, wielding a chainsaw badly, and befriended local farmers.
He says the hardest, scariest thing was trying to get his head around what he would do when he got out.
In the end he was, of course, able to found and build Waterstone. He's always been up-front about his past (albeit with coverage by NBR and other media about his escapades giving him little choice at times).
Life after porridge
By choosing to live a relatively high-profile life through his political commentary and newspaper column, Grant was aware his past would always be highlighted.
At times it has hurt. NBR initially resisted publishing anything by Grant. But his self-published pieces on business were so good that he eventually inveigled his way in.
Still, his past lingers. One member of the NBR View production crew, who knows people financially hurt by Grant's offending, was disgusted this interview was ever arranged.
“It’s not on my website and it’s not a point of difference that I look to sell my business with," Grant says of his background.
“But when you look at what I do — I’m a liquidator. I’ve got millions of dollars sitting in my trust account. I got out there, I ask people, I ask banks. I was in a meeting yesterday with Inland Revenue, asking for its support [with a liquidation].
"I look at it like this: People like you who don’t have a conviction for dishonesty are entitled to a presumption of integrity; you are entitled to think that other people out there will assess you as an honest person. Your actions can confirm or dissuade people from their default position but you’re entitled to that presumption of honesty. I’m not, because I have these convictions for dishonesty," he says.
"So, if people use that as their starting point, I can’t complain about that. What I need to do is demonstrate as to why the wider commercial community and my staff and the banks and people who engage with me that I am entitled to be considered as an honest person despite what I’ve done in the past.
"And if I’m going to ask people to do that, then the quid pro quo is that, if someone like yourself says ‘hey, I want to talk about this stuff,’ I can’t duck away and hide."
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