We started out years ago on either side of the interviewing table - me with a shorthand notebook and tape recorder, he with his penetrating, bright blue eyes and opinions, espousing his views on the New Zealand economy, free-market theories, why "super smart" Helen Clark got it wrong, why attitudes needed to change.
During one interview at a downtown café with a noise volume the equivalent of a war zone, Myers didn't seem to notice that neither me nor my tape recorder could hear what he was saying. He mumbled along, eating a ham and tomato toasted sandwich, and seemed happy with the resulting article even though 80 per cent of the interview was missing.
He never questioned what I wrote and was surprisingly candid during interviews, unlike many wealthy or famous people. (Elle MacPherson once told me off for daring to ask what she'd given Elton John for his birthday present after she told me she went to his party.)
But Myers seemed not to care too much about his privacy.
He'd chat about his family, about his children, causing me to filter some of what he said just for their sakes. He talked about the affair his mother had with an American stationed in New Zealand during the war, details he allowed to be published in a book, The Myers, by Michael Bassett and Paul Goldsmith.
He talked about his privileged upbringing and wealth, trusting me not to stick the knife in for the sake of it.
Four years ago, Myers was told he was dying. Bowel cancer from five years before had spread; 12 tumours had invaded five organs and, he was told, his body would soon shut down. Doctors talked in terms of months.
He faced his cancer like he did everything in life, with a furious energy and determination.
He sought out the best oncologist and cancer researchers and bought himself time, undergoing a cocktail of chemotherapy drugs that cost him hundreds of thousands of dollars and left him with an array of unpleasant side effects.
Once I asked him if he'd sacrifice all his wealth to have his health back.
No, he answered. "Maybe at your age I would. But not at my age." He'd stick with the money and enjoy the time he had left.
After I was diagnosed with breast cancer nearly four years ago, we'd swap war stories - either during phone interviews or in email correspondence. He'd laugh at my description of my wig blowing off on the Huka jet boat in front of startled Japanese tourists.
He in turn would make light of his side effects, describing a terrifying plummet down an 18-metre cliff at the Matauri Bay family farm as his first "skydive", a fall caused by numbness in his feet after heavy-duty chemo.
And he chuckled that the same numbness caused him to trip and fall under an SUV in Eaton Square.
He called the sympathetic letters and emails from friends his "obituaries."
He kept me up to date with new cancer treatments and drugs, attaching articles to his emails.
He'd become so interested in cancer research after he was diagnosed that he invested in, and later bought, a company that tests drugs for pharmaceutical companies. As is the Myers way, that company doubled its profits within a year.
Myers was rich, richer than the Queen, a fact that he shrugged off. It was just the way it was, he said.
He was the sort of man who lunched at the Dorchester, headed off to the Seychelles for a spot of fly fishing, took his family cruising on the Med and was approached by Google mogul Larry Page to see if he would sell his superyacht, the 193-foot Senses. (It was later sold to Page for $45 million).
He could be rude and crude. Long before I met him I heard a story - possibly an urban myth - that in the middle of a Lion Nathan business meeting Myers got up to relieve himself in an adjoining toilet, leaving the door open and not letting the flow interrupt the conversation.
Urban myth or not, those that knew him thought it was quite possible.
He'd call people pricks and bastards and once showed me a carefully written note from his granddaughter: "Douglas Myers, please stop saying the "f" word and "b" word. He kept the note in his wallet.
I knew his borrowed time was running out when, in February, I received an email that read like a goodbye. He and his wife Barbara were leaving Matauri Bay and rushing back to London.
He was, he said, "pretty peaceful".
The things that mattered to him were thriving. The family businesses were "doing excellently" and his three children were married and settled. Two new grandsons were on the way. His oldest daughter Jessica, was having her fifth baby and daughter Laura her first, baby boys that Douglas knew he would never meet.
I wrote straight back but never got a reply. Even though Myers lived in London, his heart was here and New Zealand was always somewhere he wanted to come back to.