He’s fostered an image as an enigmatic underdog who proved his doubters wrong. But Robett Hollis has spent an extraordinary life trying to avoid being put in a box.

Robett Hollis wears the same outfit everyday: a plain black shirt, a black fitted cap, and a pair of Nikes.

It’s his uniform, he says. When he wears it he feels more creative, efficient, fully in work mode. These days you’ll see him wearing it on Facebook live streams interviewing industry leaders and politicians like Rob Fyfe and Paul Goldsmith, talking Covid-19 strategy and trying to funnel advice to business owners impacted by the pandemic.

It’s all part of his self-described role as a “Global Kiwi and Multi-Exit Entrepreneur” – the words boldly displayed on his website above his long list of accolades: LinkedIn’s top three most influential New Zealanders, Metro magazine’s top 10 innovators of the year, Kiwibank New Zealander of the year nominee.

Below that are his videos; each one depicting the charismatic Māori entrepreneur giving interviews or travelling around the country, inspiring business leaders and high school audiences to say #yestosuccess and destroy tall poppy syndrome.

Then there’s the descriptions of his career as a pro-snowboarder, an author, a founder of a sports media company and the creator of the country’s largest co-working space network. After 10 minutes on his website, it seemed pretty clear that I was dealing with a true force of nature: a role model, a dynamo, and possibly the most confident man in New Zealand. So I sent off an email asking if I could write a story about him.

Then came his reply: “I’m not really profile calibre. I’m just an overweight bald washed up never has been. Haha.”

It was so dissonant, and pure tall poppy – the self-effacing modesty that plagues New Zealand society at every level.

But it suggested that the man was far more complex than his image suggested. He said he was in the US; living in San Francisco with his wife and two young daughters. But after some back and forth he agreed to the interview.

A week later, we sat down to talk via Zoom.

“So what kind of story are you doing?” he asks with the same reticence. “I felt kind of awkward agreeing to this. It’s a bit weird.”

Why is it weird?

“Not many people have seen behind the curtain. No one knows who’s in my circle, and no one knows what I’m actually doing.”

“It’s almost by design, because what I learned super early on is that when you told people who you’re with and what you’re doing, it was actually intel that people would use as ammunition against me.”

It’s the type of talk you’d expect from someone who’s used to competing; who’s struggled and strategised against a system that’s geared against him. When I learn Hollis’s story, it starts to make sense.

The outsider

Hollis has been an outsider for as long as he can remember. Ngāti Porou through his father, he was born in Arapohue on the outskirts of Dargaville in 1985, the only brown kid in a community of mostly white farmers. Then, when he was five, he moved to Fiji with his family, where his olive skin made him look like a white kid in a community of Fijian and Indian kids. When the family moved to Mt Pleasant in Christchurch, he was the only Māori kid in a neighbourhood of affluent Pākehā families. It’s a trend, he says, that has continued throughout his entire life.

“This is my world. It’s tension. My entire life has been tension. But I’ve needed that because it gives me that drive.”

He uses those words a lot: “drive,”and “my lane”. They’re words that evoke images of speed, momentum, a need to move constantly. He describes it himself on a kind of prep document he sends out to potential business partners before he meets them.

“In meetings of any type, I always move, fidget and can’t sit still for more than a few minutes…. SERIOUSLY,” it reads. “So if I start rocking or moving or shaking my knee – don’t take it personally. My brain and body just doesn’t stop…. Seriously.”

It’s an idiosyncrasy that started early and would propel him through life. Then, he says, there’s his insatiable appetite to “hustle”.

The ‘hustle’

Hollis’s business career started young. At age five he started selling paper boats made by another classmate and spending the proceeds on ice cream. At 12 he was hawking A4 printouts of celebrities like Jennifer Aniston to classmates. Once, when Sir Edmund Hillary visited his high school, he got two five dollar notes autographed: one for himself and one that he could sell years later, once it had appreciated in value.

“I was hustling my way through childhood. I didn’t have entrepreneurial tendencies – I had entrepreneurial tendons. It was in my blood and bones.”

Perhaps it’s the standard behaviour of the archetypal high achiever. After all, every school seems to have at least one ultra-competitive and precocious kid who wins at everything. For some it’s just a normal part of growing up.

However, what was to follow in Hollis’s life was anything but normal.

Formative moments

By age 11, he had moved back from Fiji and had settled in the low-decile suburb of Aranui, Christchurch with his parents and two sisters.

One day, his father suddenly collapsed at the bus depot where he worked. When he was taken to hospital, they discovered he’d suffered a double brain haemorrhage as a result of a heavy stroke. Incapacitated, his brain regressed to the capacity of a six-year-old, he had to learn to read and write from scratch. Abruptly, he changed from a jovial and loving man to an angry and sometimes abusive figure as he struggled to recover.

“It took away my childhood,” Hollis says. “Instantly I had to jump to the man of the house, because I was! None of our family was in town, just my mum and two sisters. So yeah, 11 years old, and it was, ‘do I decide to be a little badass?’ No, no, because it’s going to make it harder on mum and the fam.”

Years of rehabilitation followed for Hollis’s father, with his mother the main caregiver. Despite his father’s haemorrhage – or perhaps because of it – Hollis continued to dominate the various sports and activities he tried his hand at. As a natural athlete, he excelled in softball, basketball and soccer – playing at national youth level for the latter two.

By the year 2000, his family life had begun to return to normal. His dad’s health had improved considerably, and he was able to resume work part-time.

In December, the family went on a road-trip from Christchurch to his father’s tūrangawaewae on the North Island’s East Coast and then to Waitomo to attend a wedding. On the way home, they were driving to Te Kaha when an oncoming motorist swerved across the centre line, hitting the car Hollis’s dad was driving and killing him instantly. Hollis was travelling in the car behind and saw the whole tragedy unfold.

“That was the worst moment of my entire life,” he says.

Hollis returned to school several weeks later and got on with life. He didn’t really discuss what happened for almost 10 years.

“I never wanted pity, ever,” he says. “In typical Kiwi style, no one ever brought it up or talked about it, and I finally figured out why. A lot of my Aranui clique had no dad at home either.”

He describes his father’s sickness and premature death as two of three formative moments in his life; crucial developments that would have a profound influence on his coming journey.

The third came not long after, during a visit to the career advisor at Aranui High School. Although he had his strengths, Hollis says he lacked book smarts. ”I never enjoyed sitting and learning. My brain couldn’t really concentrate on anything I wasn’t really interested in.”

The careers adviser had him take a computer assessment that would supposedly identify the most suitable careers for him. When he finished, the advisor suggested that after he finished school he could work in a warehouse packing boxes.

“When I heard those words, I flipped,” he says. “That’s your ceiling? It was just a pure feeling of determination and stubbornness and competitive drive to just dominate the whole thing, like 100%.”

It was at that moment, when the system attempted to impose limitations on him based on his background and academic record, that his natural drive galvanised into an all-out offensive.

Three years later he was a pro-snowboarder travelling all over the world.

The snowboarder

Like his business ventures, Hollis’s snowboarding career started early. At age 11 he got hooked on the sport on a school trip. After getting a part-time job at Cheapskates renting out gear, he gradually became more immersed in life on the mountain.

“For me, snowboarding felt like an ‘out’,” he says. “I figured if I got good at it, it could really take me somewhere. I became so competitive that I would constantly challenge myself to master it quickly as I did with basketball and soccer. I told my brain I would do it – so I did.”

He says he was never the best snowboarder, but his accolades tell a different story. At 18, after spending three months in Japan teaching English and snowboarding, he returned to New Zealand to win the Methven Big Air. Later that year, he turned pro, earning a full-time salary and signing contracts with the likes of Mt Hutt, Westbeach, Federation, Salomon Snowboard and Adidas.

The following year he won the Forum YoungBlood Competition in New Zealand, which took him to the world finals, where he won a silver medal. He also helped create the New Zealand Snowboard Union and was named the NZSBA rider of the year.

At the same time, he continued feeding his entrepreneurial appetite through ventures such as importing poker sets, and a snowboarding blog and content site that would eventually morph into the successful NZsnowboard.com.

And just like that, having mastered snowboarding at 20 years old and on the cusp of a brilliant career, he gave it all up. After the world finals he told his friends that he’d be retiring at the end of the year to focus entirely on producing content.

“I never wanted to be tagged as the snowboard guy,” he says. “It was the last thing I wanted on my business card. I didn’t want to be defined by a title. I wanted just to be me, Robett.

“Every business starts because of a need, and at the time I had an issue with snowboarding websites who were happy to take money from advertisers but do nothing for the industry. They weren’t supporting events, creating content, or putting anything back into the community.

“I took this personally.”

The businessman

From 2006 onward, with the backing of some industry friends, Hollis launched six other websites and wrapped them into an action sports media company. In 2011, NZsnowboard.com became Airtime, which would go on to become Frontside, New Zealand’s largest action sports network.

“Our golden egg was capturing good content and putting it in front of eyeballs,” he says.

In 2011, he married his girlfriend whom he’d met two years earlier in California, and the couple moved back to Auckland. While working in the CBD at Frontside, Hollis would eventually start his next venture: ColabNZ, a shared workspace concept that would grow to become the country’s largest network of co-working spaces for tech startups. At its height it occupied several downtown Auckland buildings, with his office on one of the top floors overlooking the city.

“I was living the corporate dream at the age of 28,” he says. “I understood that many people had worked their entire lives, struggled through the corporate game to get to the top floor of such a building.”

Yet Hollis began to notice that his success and the audacious manner in which he was rising was striking the wrong note with some people within the business community.

“There’s a certain type of individual that I’ve had some negative backlash or, you know, back-channel bullshit from,” he says. “And it comes a lot from those who don’t have enough bravery to go and do something themselves. It’s the fact that they see me genuinely being me being free, but it’s actually resentment against themselves. So I feel empathy for them.”

As a CEO and business leader, he also began to notice another factor at play. Occasionally, when someone came up to meet him for the first time, they would initially assume that Hollis’s older, white colleague in the next room was actually the CEO.

While he took it lightly and incorporated it into his distinct image as a maverick, he says it’s a symptom of the underlying racism and lack of diversity within the sector.

“It’s influenced me more the older I’ve got, because I’ve become more aware of what the world is actually like.

“It hides in all the places that you don’t expect. It hides literally at the top table.

“But I think the game is changing. And the people who get it are really embracing all those around them. And those that don’t are just going to get left behind.”

The role model

Hollis exited Frontside and ColabNZ in 2018. By this time he and his wife had had a little girl, and he had become a business mentor and keynote speaker through his company, Aranui Ventures.

Unlike traditional business speakers, he takes an unorthodox approach, channelling his own experience and natural charisma through unscripted monologues. His aim, he says, is to use his platform and profile to show others that despite their circumstances or perceived limitations, they can achieve whatever they want.

“Our epicness stays silent,” he says. “I think it’s the responsibility of every single Kiwi who’s done well to create more breadcrumbs for the next person who wants to get in their lane. And if you don’t, you’re being flippin’ selfish.”

True to his character, he’s also known to get over-animated – occasionally exerting more energy than the average audience or business associates can handle.

“I have code words from my right hand. They’ll text me or call me and say ‘Pineapple!’ Then I’ll know then that I’ve gone too loose or too gnarly.”

Those who know him well say it’s all part of what makes the man special.

“He’s a fairly eccentric character,” says Tim Marshall, a friend and former colleague at Frontside. “And he’s consistently eccentric. The way he wears the same clothes everyday and his favourite team is the Oakland Raiders – probably the worst team in the NFL.

“But he’s not perfect either, and he’d probably be the first person to tell you that.”

Is that why he was wary about revealing too much about himself?

“I think in recent years he’s become more family focused. I can understand why he’d want to keep his private life quiet and away from, well, he would call them haters.”

Who are the haters exactly? While there has been no notable public feuds, friend and business associate Rob Campbell says it’s perfectly reasonable for Hollis to be on his guard.

“Most successful people have a vulnerable side and he’s had very tough times in his life. He does get attacked, I’ve heard people say some very negative things about him.”

“He’s a bit out there and he projects a lot of confidence and energy and image. He’s got a brand and he pushes it hard. And there are people who are jealous or annoyed of that. Some establishment people he really pisses off and they need pissing off, to be honest. He doesn’t like being disliked, not many of us do. But it doesn’t stop him pushing ahead, and that’s great.”

Pride

Having shared his past through Zoom, Hollis tells me about his next big project: fatherhood. With two young daughters and a pandemic preventing the family’s move back to New Zealand, he doesn’t get out all that much – but that suits him fine on his mission to be a present dad.

Has his new role changed his perspective on life?

“I’m way more calculated than I was 10 years ago. I got two daughters under two and my priorities have shifted. But am I still just as hyped on certain things? 100%! I think I’m probably just using more of a sniper to shoot shit now instead of a shotgun.”

The shotgun, the sniper: they’re the words that evoke images of battle, of competing, of someone who has New Zealand’s insecurities in his crosshairs.

Does that include his own? After all, there was still the paradox of his self-effacing email. Is that what he’s concealing behind the curtain?

He ponders it for a moment. “I was kind of fearful to do this interview. Because sometimes I don’t think I’m worthy of the spotlight. So in some ways, maybe I’m being tall poppy against myself too.”

He says it comes down to a struggle between pride and arrogance and a desire to use his profile as a conduit for other’s success, rather than “flexing” his own accomplishments out of ego. It’s an inescapable byproduct of having his story, his personality, intimately woven with a public-facing brand.

But what about him? When he changes from his black uniform into his “chill clothes” and takes a break from the hustle to sit still and reflect on his life, what does he feel?

“I’m proud of it. I’m extremely proud of it,” he says.

“I got it.”