In our case, Brian's long-held passion for the news media generally and business news, in particular, coincided with a deeply challenging period for the media, but one in which the notion of paying for news was gaining currency.
He backed us to succeed, bringing not just his capital but the sound instincts, relentlessness and clarity of vision that marked his many contributions to NZ's public life and public markets.
His business style was refreshingly straightforward.
After several weeks of lawyers suggesting multi-page agreements with numerous appendices to document his investment in BusinessDesk, Brian produced a set of words so frighteningly succinct that they barely ran to two lines.
It would either work or it wouldn't.
It did.
There were many things Brian disliked, but legal documents, banking processes, shabbily constructed IPOs and the failings of NZ's capital market regulators were always near the top of his list.
Of banks, he once remarked: "Banks are like the sort of person who asks for their umbrella back when it starts to rain."
Driven and restlessly energetic, he was one of the NZX's greatest champions, in that he deeply opposed the loss of major listings to offshore exchanges, but also one of its harshest critics, precisely because of his ambitions for what he felt it could or should be.
That was Brian.
His columns on a Saturday morning were required reading for every investor and for anyone who wanted an investor's money.
He was the small investor's champion, a campaigner for a fairer but also more vibrant investment environment, and very often the scourge of the top end of town for expressing views that were often unpopular, iconoclastic and emphatically expressed.
Brian was a man whose preference was to call a spade an extremely poor shovel.
There was rarely any doubt about where you stood with him. His standards were as high as his generosity to the people, causes and businesses he decided to back.
The old days
I met Brian Gaynor as a cub business reporter for the Dominion in 1983/84.
Those were free-wheeling days. Sharebrokers, equities analysts and journalists regularly shared gossip that would often, today, be a clear breach of NZX listing rules.
Back then, those rules didn't even seem to exist, let alone be written down.
While Brian would become one of the foremost champions of ending such practices, he was generous to a young journalist, gregarious, a mine of information and, being Irish, had no objection to a serious discussion over a beer.
Just last week, a contemporary of Brian's from those times described him to me as "one of the investment gurus" of the 1980s investment world – a surprise when his own description of his entry into the investment world was that it was an accident. He came to NZ from Ireland "with a rucksack on my back" and ran out of money.
His first job was with the broking firm Daysh, Renouf. The rest is history.
As a young journalist then and an older one now, he had contrarian views that were always worth listening to.
He had a tendency to be right about how things were likely to play out.
He was a formidable analyst who mixed the empirical with a solid dose of gut instinct, which he trusted more than perhaps anyone I've ever worked with.
Champion of change
Back in the day, he may have heard the gossip, but he also spent most of his career fighting the lax environment that meant small shareholders were usually the last to know what was happening to their company.
"We had very weak regulators at the time, to the extent that the Securities Commission really didn't have any statutory powers in terms of prosecution," he told the Spinoff's Michael Andrew last year, discussing the 1980s. "They could write reports and make recommendations about new laws that should be introduced. But they had no statutory power like the FMA does, to actually investigate something, and to prosecute someone."
Back then, our interactions were genial, casual and occasional. He was a master of the universe to my somewhat star-struck neophyte.
Later, Brian was seconded into the advisory group of the then prime minister, David Lange, at around the time I was preparing to leave the office of the finance minister, Roger Douglas, and the two titans of the fourth Labour government were at war.
From what Brian has told me more recently, it is clear that he was one of those who persuaded Lange to can Douglas' December 17, 1987, flat tax package – a radical set of measures in which Douglas hoped to exploit the economic pall cast by the October 1987 sharemarket crash to entrench the Rogernomics revolution.
To Brian, they were the apogee of an approach to economic policy that was deeply at odds with his own politics, which seemed to me to be essentially liberal and centrist. He was deeply sceptical about the idea that allowing nationally significant assets to be sold to offshore owners was in NZ's best interests.
He was a capitalist, and a flinty one when negotiating a deal and insisting on the letter of it.
But he was more economic nationalist rather than a neo-liberal enthusiast.
For many years after the Beehive, our paths would cross only occasionally.
A mighty pen
During a stint as communications manager for Contact Energy, I had my first real taste of Brian's influence as a columnist and his staunch advocacy for a stronger domestic capital market.
Contact's majority owner at the time was ASX-listed Origin Energy, which had structured a takeover of Contact as a dual-listed merger, angering a swathe of the top end of town in NZ corporate circles.
I recall ringing Brian to remonstrate about a column roundly attacking the proposal, and his response. It was emphatic and to the effect that it didn't matter how much PR spin or money the Aussies threw at Contact's NZ shareholders, this takeover was bad for the NZX and bad for the country.
Brian had firmly held views about most of the big names in NZ financial circles of the past 40 years, as well as an encyclopaedic memory for the rogues.
Such was his tendency to forthright expression that while Brian had a massive following as a columnist first in NBR, then the NZ Herald for more than 22 years, and then with BusinessDesk, he excited strongly held views in return.
His habit of routinely eviscerating the performance of the NZX, criticising the growing dominance of NZ capital markets and broking activity by a decreasing number of advisory firms and calling out shonky-looking IPOs exasperated powerful rivals. In some cases, enmities ran deep and both ways.
Now, suddenly, he is gone.
Geoff Senescall, one of the Herald's top business journalists in the 1990s, summed it up in one of the dozens of text and personal messages that have begun flowing since the news of Brian's death was announced.
"Extraordinarily sad news about Brian. A huge loss of market knowledge and also for the rights of the little joker. Can't quite believe it."
