When he left school he joined the NZ Army band as a trumpet player. It was the chance to travel as a professional musician that appealed, he tells the Money Talks podcast.
But with music as his profession, Roberts kept up his interest in investing.
He joined an investment club as a teenager with friends and family, and they all deposited $50 a week into a joint bank account.
Roberts describes himself as a natural risk-taker and a spender, but despite that – or perhaps because of it – he maintained his disciplined approach to investing through his poorest days as a student.
After a successful career at Kiwibank he took his biggest risk in teaming up with workmate Sonya Williams, their respective partners Brooke Roberts and Ben Crotty, as well as tech-savvy friends Richard Clark and Martyn Smith to create Sharesies.
“We quit our jobs to start the business. We started Sharesies with $20,000. When you’ve got six people trying to live off of it and build a company on it, it’s not a whole lot of money.”
The trading app has gone on to transform New Zealand’s investing landscape – particularly for younger people – allowing investors to buy into the share market with as little as $5.
Since launching in 2017, Sharesies has signed up more than half a million investors and has $2 billion of funds under management.
Roberts says the social inequality he saw in the investment world was one of the driving reasons for creating Sharesies.
“The fundamental problem is that people don’t start on equal footing, right? Most New Zealanders get their financial advice from their parents, or someone close.
“In fact, quite a small number of people in New Zealand actually have really good role models for that.”
Lack of education, low wages or issues like lingering fear of the stock market (after the wipeout New Zealanders endured in 1987) pushed people away from direct investment, he says.
“So we have a huge amount of people, and a huge amount of our economy, involved in housing as opposed to productive companies.
“The economics are a little bit twisted in New Zealand. I do think places are happier when there’s much more equality.
“That’s not to say I don’t think you need more wealthy people as well.
“But that’s not an ambition in itself. It’s a byproduct of something that you’ve achieved.”
When it comes to shifting the dial on poverty and inequality, Roberts says he likes ideas such as the universal basic income (UBI).
“But if we can start people young and do a much better job of giving people a platform so we’re on a much more even keel, I think that would be huge. And then things like financial education and stuff can become really, really valuable.”
As for his own wealth, Roberts says most of his money is going back into the business for now.
“I’m a pretty boring investor myself with funds and ETFs and stuff like that. But every now and again, I decide I wanna pick a company. And I give it a good crack.”
Listen to the full episode of Money Talks for more from Roberts on his experiences with money.
Money Talks is a podcast run by the NZ Herald. You can follow the series on iHeartRadio, Spotify, Apple Podcasts, or wherever you get your podcasts. New episodes are out every Saturday.