Logan Freeman has only seen his dad get mad once - when Freeman spent his entire $11,000 savings as a 15-year-old buying socks from China.
Yet Freeman's big move starting a sock brand during high school quickly paid off because at age 18 he used his $40,000 hosiery profits to buy his first home.
His property success contrasts with that of many other young Kiwis.
Home ownership rates have plummeted over the last 20 years as houses have become ever more expensive on the back of skyrocketing prices.
But Freeman - like 25-year-old property investor Riyaan Mohamed who featured in a Herald report last week - said he's "sick of reading" media reports about how hard it is to buy a house.
The negative reports only convinced young Kiwis to give up, believing it was too hard, he said.
Freeman - who raised the $11,000 start-up cash for his sock venture from after-school work washing cars - said he was only ever offered sound advice rather than cash handouts.
Both his parents were real estate agents and he's watched family friends make plenty of money from property investing.
That gave him the motivation to save and take up an after-school job washing cars, while also spending his nights dreaming.
"I used to draw ideas and think of ways to make some money - then one night I started drawing socks," he said.
Sitting up all night, he posted a buying request on a Chinese website.
A bunch of factories wrote back, and after a week Freeman picked one.
"I spent every cent I had - it was $11,000 from washing cars - on the socks," he said.
"That was probably the first time I'd ever seen my dad mad. But I said, 'watch this I'll get rid of them'."
Freeman pounded the pavement, walking into retail outlets and delivering his sales pitches in his school uniform.
Once he got it into one store, other outlets noticed and even Australian stores contacted him.
His phone started running hot in school during accounting and English lessons.
"I had a room in my parents house that was full of socks," he said.
"I'd be on the phone getting orders, and I'd text my mum and she'd go package them up and send them away - that was 100 per cent what I did at school."
"I sucked in the classroom, my teachers hated me, and I was ready to leave on my final day."
The day after his final school exam, he started selling cars at a Nissan dealership.
The job gave him the steady income he needed to convince the banks he could repay a home loan.
About six months later in 2015, he put down a $40,000 deposit on his first house, a three-bedroom unit in Edgeware on Christchurch city's fringe for $305,000.
Eighteen months after that in April 2017, he bought his next two-bedroom flat on the same street in Edgeware for $320,000.
New Loan-to-value restrictions meant he had to put down a 30 per cent deposit, but he was able to cover that through a mix of fresh savings and his first house gaining $25,000 in equity.
Months later he paid $395,000 for a third house, a newbuild two-bedroom townhouse in Richmond, once again using a mixture of refinancing his home loans.
He credited the purchase to an "amazing" mortgage broker, who actually sent Freeman out to look for the third house after telling him he had enough equity to buy again.
He said it was easier to get a loan when buying newbuilds.
And while the rents from the houses weren't enough to pay off the mortgages, Freeman said he was able to make repayments from his salary while still also saving extra cash.
Now after four years as a car salesman - including one year back at the Mercedes dealership where he originally washed cars - Freeman has started as a real estate agent with Harcourts in Christchurch.
He mostly deals with first-home buyers and investors and puts as much time into helping young buyers as he can, he said.
He tells them he bought his houses by getting the best advice possible, wanting it and working "stupid hard" - yet he also feels like he hasn't had to sacrifice too much.
"I stopped playing rugby to work, but it didn't bother me because I was no good anyway," he joked.
"And I'm far from stingy, I buy stuff, I go out drinking, but I also know that if I spend X amount of money, I have to work extra hard to make it back."