Jack Boxer

Occupation: Founder, Vysionary

Location: Sydney

Investment approach: Medium-term investor

Let's start from the beginning: what got you into investing?

I blindly put $250 into bitcoin in 2017 when I was 18. But for the stock market it was a combination of a couple of things.

I read the book Maximum Achievement by Brian Tracy and it opened my eyes to the fact there were more opportunities out there than just a job, and that led me to investing. Also my grandfather (we call him Puppa) had a lot of his money invested and a chat with him solidified that I should start.

What were your first investments?

Ha! I thought the cannabis industry was about to take off with legalisation and wanted to invest in Dan Bilzerian’s Marijuana company, but it was private.

So, my first ever stock was a company called Cronos Group ($CRON), who are engaged in cannabis research and product development. My second investment was a random Florida based Insurance company.

My first ‘smart’ investments were Disney ($DIS) and the Vanguard total stock market index ($VTI).

Describe your investing style

I would look for companies that had huge potential over the next 2-5 year time frame. 

I’ve always been a long term investor, but favour businesses with a super exciting outlook in the medium term. I would always dollar-cost average into positions.

What stocks or ETFs have been your biggest winners?

In no particular order…

• Palantir ($PLTR). I invested $10K over about a month in early 2021, with an average cost of approximately US$24. I sold everything in May 2025, when I moved to Sydney to start Vysionary, at an average price of around US$90. This turned $10K into approximately $33K. The share price has doubled since I sold – it’ll either be the smartest or dumbest decision I’ve ever made.

• Tesla ($TSLA). I turned approximately $1K into around $8K the first time I invested, between 2018 and 2020. The second time was more like a 40% gain from what I can remember.

• Meta ($META). I turned approximately $1.6K into around $5K.

• Nordstrom, a now delisted stock. I turned $3K into over $6K.

Did you always plan to use your investments to start a business?

No. Initially, the plan was to just consistently invest and grow my portfolio over decades, with the goal of eventually living off dividends. I was obsessed with passive income when I was 18!

I sold everything in May 2025 to fund Vysionary and all of my money is tied up in the business for now.

What research do you do before buying a stock?

To be honest, most of the time when I found a company, I would watch as many YouTube videos as possible of different people analysing the stock and get as many opinions as possible from people who have already done the deep dives on the numbers.

I would ensure I understood exactly what they sell, and the likelihood of that stock’s market cap reaching or exceeding that of some of their bigger competitors. I would also always watch interviews of the founder – that tells you a lot.

How did you first react when you saw one of your investments go down?

It definitely makes your stomach drop the first couple of times. But after a while, you realise this is just part of the game and short term movements mean nothing, mostly.

You have to try to stop yourself from checking your portfolio every day. When a stock does dip, try to understand whether it’s because the entire market has dipped or if it’s something specific to the company.

Market shifts happen all the time and mostly shouldn’t change your opinion of the stock you hold. It just presents an opportunity to increase your position at a cheaper price!

What advice would you give your younger self before making your first trade?

Take bigger bets. Focus on making money first, then invest. If you hit a 100% - 300% winner but you only invested $500, it doesn’t mean much. Whereas if that happens with $10k, you’ve just made half the average yearly salary. 

Do more research. Invest in a smaller number of companies you truly believe in and ensure you have a goal sale price before you start buying.

How does it feel to be an investor?

It feels powerful. Knowing you own a piece of some of the biggest companies in the world and your net worth is rising with their company valuation, it’s awesome. Plus, knowing you’re making money from your own good judgement is an incredible feeling.

The personal views in this article do not reflect the views of Stake and do not constitute financial advice, nor a recommendation to invest in the securities listed. Past performance is not a reliable indicator of future performance. As always, do your own research and consider seeking financial, legal and taxation advice before investing.