Usually when I interview someone, I ask most of the questions. That’s normally the way it works. But when I meet Jack Yan, he’s found out all about me before we even sit down. He apologises, and we meander our way through an interview that lasts almost three times as long as planned, and involves many tangents and rants on both our parts. I have to confess, I’ve never enjoyed an interview more.

But lets get back to Jack. He is the editor of fashion magazine Lucire, has dabbled in politics, web design and contributed to piles of books, columns, magazines and papers. He speaks 2 dialects of Chinese, English, French, some Swedish and German, blogs extremely frequently, is a business mentor, judges Miss Universe New Zealand, and runs a thinktank in Sweden. I wanted to ask him what his inspiration is to do all this, and what he’s planning to do next.

He initially founded his own font company in 1987 while still a teenager, doing calligraphy and then moved onto becoming the first digital typeface designer in New Zealand.

This theme of being ‘first’ rears it’s head often, and Jack says that this, rather than the money, is where the appeal for him always lay. “It’s like going to the moon, everyone remembers Armstong, and a lot of people remember Buzz Aldrin, but after that, who else went to the moon? No one remembers those guys. I’m sure they got rich because they went to the moon, but in terms of reputation, it’s Armstrong who gets it. And I suppose, coming from a not really rich background, money has never been a be all and end all. Money has never defined me.” Then he adds as an afterthought, “and my bank balance proves that that is true!”

I learn that his drive to succeed had slightly more sinister roots too, as he quietly describes the racism that he experienced while growing up. “I guess it was kinda a good thing there was prejudice and racism. It gave me a stubborn ‘I’ll show you’ attitude, and made me work extra hard to achieve my goals. You know, I went to Victoria University and did a BCA, majoring in Marketing. At that time, if you were Chinese and doing a BCA people assumed you were doing accounting and there wasn’t room for anything else. I would never want to just be something because the system tells me I should. And going back another generation it’s grocers and Chinese takeaway owners. It’s that I don’t want others to go through this, I don’t care what race they are.”

“So I guess I was able to turn a negative thing into a positive thing, I saw being first as a way to leapfrog all that negativity that used to drag me down. I thought, I’m not going to be compared to anyone if I’m first.”

Another way he was arguably first, was when he started doing web design in 1992. He laughs when he thinks how he dismissed the internet as just another fad. “I’ve had an email account since 1989 but I never saw the point of the internet. I thought, why would you want to be on the internet?”

But he saw the opportunities soon enough, and began using the web as a publishing medium. “At that time Vogue and Elle weren’t online. There were Mercury and Saturn, two car brands and a couple of TimeWarner sites, but generally the web was a vast frontier of nothingness.” So he put CAP online in 1994, making it one of the first business magazines on the internet.

But the real dream was to own a fashion magazine. He’ll admit that he didn’t have a great knowledge of fashion when he began, but he says “I thought ‘I know what I like, I know what a good photo looks like, I have a basic understanding.’ The reason I picked fashion was because in 1989 I bought a copy of Studio Collections, and it was the most beautifully typeset magazine I’d ever seen. I thought that if that has an impression on me, it will have an impression on someone else. So it became a sort of obsession, I wanted to see a fashion magazine online. Just wanted to prove to myself it could be done. And that’s how Lucire began.”

Lucire missed an issue this year, which Yan calls a ‘great source of shame’. The recession has hit hard, and advertising is down. But still, it migrated from online to print, another first, and proof that a web brand could become a print brand. It is currently being printed in New Zealand and in Thailand. “I had one in Romania but I had to shut it down. It was tough because the mafia control the distribution there. So unless you are prepared to give out brown envelopes you will not be distributed. So we shut it down.”

He’s been accused of being contentious, and praised for being opinionated. I have to ask: what does he think? Does he consider himself a deliberately contentious person? There was the very publicly aired laundry after his departure of his longtime stint on TVNZ Breakfast Show in 2006. There’s his open hatred of Facebook, whom he says are accusing him of violating copyright. And then there’s the time he registered the trademark of just recently defunct Magazine Pavement provoking a barrage of abuse and his steadfast insistence that he did it transparently, and wanted to help rescue the magazine.

But while he denies the ‘controversial’ label, he will admit he’s outspoken, “I’ll say things that are a bit extreme to provoke a reaction, I want people to think about what I’m saying.” He also mentions what he reckons isn’t necessarily malicious racism, but does affect people’s view of him: “If a white man walks in the room and does something, they call him confident. If a woman walks in the room and does exactly the same thing, they call her bitchy. And then if a coloured man walks in the room they call him arrogant.”

Back to Lucire, he says the enquiries for publishing it overseas are still coming in, but it’s hard to tell if they are serious. “It’s hard to tell if they’re just trying to beat the recession. That’s one of the things about owning a fashion magazine: everyone thinks you are a moneybags.” He becomes a bit downcast at this point, telling me “That was something I noticed when I first started the print magazine. The number of sociopaths and leeches and losers that try to cling onto your coattails was mindboggling. I had run the web side of the business for 7 years by then and arrogantly thought, “I know how to deal with difficult people. But no. I was not prepared. It was a hard lesson to learn. Employees, freelancers, the whole bunch. I knew that there were people that I was paying, that did not have my best interests at heart.”

On a completely different, and far more upbeat note, he delights in telling me that he was recently asked for ID while out on a pub crawl in Christchurch with ‘some young folks’. “I thought the bouncer was kidding! And when I saw he wasn’t, I showed him my ID – I think he got quite a shock when he saw I was about 10 years older than him!”

Time to wrap up our extended interviewing session, and so we turn to discuss his current plans.

For now, while he’s probably better known outside New Zealand, he still works here from his home in Kilbirnie, Wellington, and travels when he needs to. He’s a volunteer business mentor at the moment, which he finds rewarding and enjoys immensely, and has turned his ‘old-fashioned’ hand to what he calls ‘courting’. ‘It’s expensive!’ he chuckles.

Besides the gigantic car-database website he’s building, he’s concentrating on his font business, and his consulting company. And he just happens to be gearing up to run for Mayor of Wellington too. He starts out forbidding me to mention this fact, but then relents. Given his longstanding track record of achievements, it looks like a definite possibility that this is another he’ll be able to bag before he turns 40.

I leave the restaurant keen to wait and see what the future holds for Mr Yan. A few more firsts, maybe some more opinionated controversy? Maybe next time I see him we’ll stick to the prepared questions. But then again, I really hope not!