But if this was fairytale stuff to rank alongside Cinderella going to the ball, even more mind-blowing was how that one crazy night of crime effectively also launched a ceiling-busting career path in the footwear industry.
Through his new athletics links, Armstrong secured a part time job unloading containers of Converse shoes in an Auckland distribution centre - which ultimately led to him being appointed president for Adidas North America in 2018, where he oversaw 12,500 staff, inked deals with some of the world’s biggest sports and music stars and took annual profit to a record $US6 billion after a couple of years.
In the latest Between Two Beers podcast out this week, Armstrong reflected on a life less ordinary, in which he had enough smarts to rapidly rise through the ranks in the footwear industry after being born in Otara and surviving an often messy upbringing in the boondocks of Massey, with four step-fathers, six sisters and three brothers.
Having dropped out of school at 16 with nothing to show for it except a bad Westie mullet, Armstrong quickly developed the gift of the gab, and was extremely proactive. He soon got on the road making sports shoe sales, and by the age of 24 was head of footwear at Adidas New Zealand.
From that toehold he proceeded to precociously climb the corporate ladder and land major leadership roles in Germany, Hong Kong and South Korea before getting the gig as president for Adidas North America.
Here Armstrong can name-drop some ultra-impressive dealings, playing a link role in facilitating Inter Miami’s signing of Lionel Messi, securing Kansas City Chiefs quarterback Patrick Mahomes on an Adidas promotional contract, and working on projects with Grammy award-winning rapper Pharrell Williams.
And then finally, in 2022, Armstrong walked away from this rock-and-roll lifestyle and returned to New Zealand in pursuit of being a better dad in the wake of his divorce, not wanting his children to experience the same disconnect he had often endured as a kid.
Messi to Miami
Armstrong can point to a host of highlights during his years abroad, but was particularly proud to have played a small role in helping get football superstar Lionel Messi to Inter Miami, after one of the co-owners reached out for a meeting, initially insisting he just wanted to show him the club’s stadium.
“I was like, ‘you haven’t come this way this far to just show me the stadium because you’d love Adidas on the side of it.’ And he said, ‘we’d love to have that conversation, but buildings don’t create connections with communities, right?’
“Then the truth really comes out. He said, ‘Look, we’re thinking about trying to get Messi into Miami’. At that point in time, the Saudi Arabia thing wasn’t really on the horizon and there was no way he was going go to Latin America. If he’s going to go anywhere, it’s going to be the United States. And out of all the teams in the United States, where’s he going to go? It’s going to be Miami...
“So I write to our global head of sport relations, who’s an amazing guy, been with the company a long, long time, and said, ‘put them in touch’, and told him that this was their plan.
“And that was the end of my doings. But now if you watch the (David) Beckham documentary, after that, they went up and met him and obviously the magic happened. And so I claim I got Messi into Miami.”
Later, Armstrong could also more tangibly point to about 600,000 Messi shirts being sold on “launch day”.
Patrick Mahomes and million-dollar deals
Just as fascinating was Armstrong’s nervous dealings in trying to negotiate a contract renewal with grid iron superstar Mahomes - who already had one Superbowl under his belt - as a promotional athlete during the COVID pandemic.
“Obviously in COVID, we were going through crisis management. So investing more money into athletes when they’re not playing, there’s no sport and we don’t know how long this thing’s going to last.
“We’re in financial trouble, like can we pay our employees, let alone extend an athlete and again, football in Germany is not known like football in the United States...
“So we’re doing the pitch. And I’m on Zoom and sitting in Portland and I’m nervous we would lose Patrick, because Nike was obviously offering a ton of money and we couldn’t compete with that money.
“We’re doing the pitch and ‘hey, we want to make a training shoe for you. The golf guys are interested in doing product with you’. Because he loves golf, he’s amazing golfer.
“And halfway through he goes: “You guys have been good to me, you’ve been so loyal to me. Stop. Let’s keep this going. I’ve got no interest in going anywhere else. Let’s keep this rolling.’
“My face lit up. I thought it was sensational, because I had to battle to get the funds out of out of the board and all the rest.
“And the most humbling moment was about 24 hours later, reading on ESPN Kansas City Chiefs announced Patrick Mahomes extension for $US525 million.
“Next time, he said, ‘I could see man that you’re going through so much pain - I don’t want to put you through that. I knew I had this deal done. So your $US1 million didn’t add sh*t’.
“He’s just a humble, humble human... I just love watching him on Quarterback (television documentary series developed for Netflix).”
Creating funds with Pharrell
Armstrong also forged an instant connection, with Pharrell Williams, a long-time collaborator with Adidas, who was very committed to the idea of “giving back”.
“He’s one of the most intelligent guys I’ve ever, ever met. very calm, very captivating. Every word that comes out, you say, ‘oh, man, I wish I was that smart’. But he’s also really intense. So when he’s with you, it’s on.
“We just became closer and closer. And I’m not saying we were mates but I had the opportunity, meet him multiple times.”
That included at Super Bowl Miami in 2020.
“We had to have a chat about some business things that were going well, and he said, ‘hey, something in the water in Virginia - I want to do this event and put Virginia back on the map. And I want to make sure we’re giving back to where I came from as well’.
“I said ‘We’ll be there, we will support you - my great grandfather was from Virginia’. He goes, ‘Why didn’t you ever tell me? Was your great grandfather black?’.
“Yes. And he just looks at me: ‘Brother’. I think because I didn’t tell him that, to use as leverage, I also gained even more trust.”
Pharrell asked Armstrong if Adidas could build him a promotional basketball court on the beach in Virginia. Armstrong not only authorised a $1 million project but made sure the Adidas recruitment and talent acquisition team and design teams were there.
This Armstrong defended as a good use of company money.
“If you’re happy to have these consumers buy your product in places all throughout the United States. And then you’re so happy to spend your money on the big glittery things versus these being the kids that actually pay our salaries.
“They’re buying our product, they’re wearing our product, they’re endorsing us. And if you don’t really support the community in authentic way, it’s a really dangerous way to to kill your brand fast.”
Armstrong ended up creating a fund with Pharrell to the tune of $US10 million called Black Ambition, that every year has budding entrepreneurs propose ideas for start-ups.
“I was lucky enough to present back to the inaugural year. Unfortunately it was on Zoom and Teams because of COVID, but seeing them burst into tears, that they had the backing of Pharrell and Adidas and money to start their business ideas from a couple of presentations with somebody, I’ll never forget.”
An unlikely meeting with Prince Albert
But for all his corporate interactions, as far as name-dropping goes, Armstrong’s unwitting acquaintance with Prince Albert of Monaco (monarch since 2005) is hard to beat.
In 1996 Armstrong got a call out of the blue, inviting him to join a New Zealand team for the World Bobsled Push Championships as a brakeman, in a paid-for trip to Monte Carlo.
It was not something Armstrong had ever done before, but he took up the challenge.
“Anyway, the opening ceremony, we’re at the palace (Monaco). As you do, you walk around and shake hands and kiss babies and talk to people.
“So I meet the captain of the Monaco team. We’re talking away for a decent amount of time and I say, ‘man, your English is good’. Anyway, I’m just talking like a normal Kiwi and he says ‘I really enjoyed talking to you. Here’s a personal invite to the closing ceremony at my personal nightclub’.
“Okay, great, awesome Albert, thanks.”
It took team mate Nigel Avery to inform an astonished Armstrong that “Albert” was actually the Prince of Monaco.
“I went to the private party afterwards, and had a good night. And he (Prince Albert) said, ‘What time’s your flight tomorrow?’ I told him, he said ‘blah, blah, blah, we’ll pick you up’. So cool.”
But the next morning in leaving the Grand Hotel in Nice, Armstrong was alarmed when his driver appeared to be taking a wrong turn.
“My French is rubbish and the French driver is not really responding too much. Anyway, we pull up and the palace helicopter is sitting there waiting for me and takes me across to the Nice airport where the boys are sitting on their butts.”
Returning home to NZ
These days Armstrong has thrown in his lot with rising Kiwi baby and children’s clothing company Jamie Kay, which he is working to turn into a global brand.
His return to New Zealand was triggered by a several factors, including experiences during the COVID pandemic, when in isolation he read “The Top Five Regrets of the Dying” by Bronnie Ware, a book which outlined the most common regrets that the people the author worked for in palliative care had expressed.
At the same time, he endured a sobering conversation with his son on a road trip.
“My son was very quiet and I said ‘what’s wrong’? he said, ‘You’re just a stranger now’.
So despite having just signed a 3-year extension as president, it convinced Armstrong he needed to put his kids first, with a return to New Zealand a core part of that.
Meanwhile back in Auckland Armstrong still reflects on how Dallow made this epic journey possible all those years ago.
“He (Dallow) was fun, but also strict. I didn’t realise that at the time, but every weekend, he made me go and help him in his garden - he had all these palm trees - and I realise now he was keeping me off the streets.
“I was getting some pocket money and his lovely wife, Denise, would would feed me and it was always a beautiful spread, which I wasn’t used to. And then every single night he’d be there for training. It was awesome that all of a sudden I had someone there - a constant my life.
“At the start obviously there wasn’t that sort of love. But over time, I just absolutely adored the man. And it wasn’t for him. I wouldn’t be here today.”