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Meet Jakson

What was your relationship with money like growing up?

Growing up, my grandpa always taught me to live within my means, budget carefully and save consistently. Go line by line through your expenses and watch where your money goes. He also preached to me to save hard, buy a house, follow the path and you’ll reach financial freedom.

I still track spending very closely today, but my perspective has evolved from what my grandpa taught me. Housing in Australia feels very unattainable for young people, so I've become more focused on investing, leverage and mobility rather than the traditional save-for-20-years-and-buy-a-house pathway. That has even meant using margin loans to accelerate my portfolio, which probably would have given my grandpa a heart attack. But the conventional wisdom seems less wise when a Melbourne house deposit will buy you a slice of turf in Sydney, if you're lucky.

What was your first job? (And how much did you get paid?)

I worked at KFC, packing chips and taking orders for a mighty $8.65 an hour at the age of 14. I couldn't do much investing back then, most of it went straight into school lunches.

How did you first come across investing?

While at university, I became fascinated by financial documentaries and the stories of some of the biggest figures in markets and business. People like J.P. Morgan, John D. Rockefeller, Bill Ackman and Michael Burry.

Finance felt like a window into this mysterious world of ambition, risk and psychology, and that fascination pushed me to learn what happens behind the curtain in investing and markets.

Was there a memorable early investment?

The first stock I ever bought was Super Retail Group after watching an Ausbiz video. I bought it at $12.25 and sold it at $15.42, then watched it climb to $18 about a year later. A painful lesson in patience.

How are you currently investing and can you provide a breakdown of your portfolio?

I'd describe my current approach as contrarian investing. I spend a lot of time reading news and watching events play out where markets usually overreact to temporary bad news: slowing growth, lawsuits, negative sentiment.

Companies like UnitedHealth Group, Delta Airlines, PepsiCo and Woolworths Group are all examples of businesses that have gone through periods of heavy pessimism. Predicting the future is very difficult (impossible), but I'm fascinated by the idea that a multi-billion dollar company can lose enormous value in a matter of days due to sentiment and market psychology.

Identifying when fear is doing more work than logic, that is the edge I am looking for.

Where do you see investing taking you?

Ideally investing gives me the thing money can’t actually buy: freedom and time.

Not a private jet landing in Gstaad or yachts in Mykonos.

Just the ability to say:

• I don't want to do this job anymore

• I'm taking a year off in Europe

• Or simply, less stress and more optionality in life

What is one super extravagant and outlandish purchase that you hope investing will be able to buy you in the future?

A house somewhere in Europe or Asia (once I sort out the visa situation), where the property market doesn't require me to harvest my organs for a deposit.

If you only had 25 words to convince someone to invest, what would you say?

Why gamble at the casino when you could slowly become an owner of the world's greatest companies? Better odds and better flex.

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Today on Get Started Investing

Bryce and Ren are joined by community member Damon on the latest episode of Boost My Budget.

Damon’s income varies a lot. He’s flying blind on how well his young family is actually living within their means. He’s wants sure up the long term stability of his families financial future.

He currently takes out $400 in cash every week, but what for? And how close is his family to saving a deposit for their dream home?

We analysed 12 months of his spending to turn this non existent budget into a steady road to financial safety.

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3 Pillars to this Contrarian Investor’s Philosophy

Jakson's strategy of buying companies like UnitedHealth and Woolworths during periods of heavy pessimism shows his belief in contrarian investing. It is one shared by Orbis, a global fund manager with over 50 years of history doing exactly this. Eric Marais, an investment specialist at Orbis, broke down their approach with Bryce and Ren on Basis Points. (Spotify | YouTube)

Eric: Our first pillar is fundamental. We try to think about a stock as though we’re going to buy the whole company and hold it forever, rather than worrying about what the price will be tomorrow or next quarter.

The second is long-term. Because we assume we will hold a company forever, what matters most is the underlying cash flow the business generates, not short term price movements.

The third, and the one that ties most directly to Jakson's approach, is contrarian. Orbis looks for opportunities that others are paying less attention to, things that are neglected, sometimes controversial, and don't carry the same spotlight as the most popular stocks in the market.

The logic behind why this works is simple but easy to forget. To buy a stock for less than it is worth, somebody else has to be willing to sell it to you for less than it is worth, and that is not a normal part of human behaviour. The most common reason someone is willing to do that is a run of bad news, a cyclical company at the bottom of its cycle, or a strong business going through a temporary rough patch that its current owner does not want to ride out.

It is worth being honest about the emotional side of this too. Being wrong alongside the crowd feels fine because misery loves company, but going against the crowd and being wrong feels awful, even though that is precisely the trade-off contrarian investing requires.