How I'm Investing: Jack Boxer

Name: Jack Boxer

Time investing: Eight years

Jack was inspired by his grandfather to start investing, and his first position was a small amount of bitcoin when he was 18, but since then he’s grown his portfolio to the point where he’s been able to cash out and start his own business.

Like any investor, Jack’s had his ups and downs but his big bets on tech companies have paid off and he’s comfortable taking bigger bets as he holds his convictions even during dips. Here’s how Jack invests.

A note: Do your own research and make your own decisions. This article gives you insight into the trading strategies of Stake customers and real life examples of how they approach investing. It’s not a recommendation to invest in any stocks featured and should not be taken as financial advice.

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 Success 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 I wanted to invest in Dan Bilzerian’s Marijuana company but it was private. 

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).

What’s your investing style and has it changed over time?

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 would favour businesses with a super exciting outlook in the medium term. I would always use dollar-cost averaging into positions.

What have been your biggest wins to date?

In no particular order…

• Palantir ($PLTR): I Invested A$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 approx US$90. This turned A$10k into approximately A$33k. The share price has doubled since I sold – it will either be the smartest or dumbest decision I’ve ever made.
• Tesla ($TSLA). I turned approximately A$1k into approx A$8k the first time I invested between 2018 to 2020. The second time was more like a 40% gain from what I can remember.
• Meta ($META). I turned approximately A$1.6k into around A$5k.
• Nordstrom, a now delisted stock. I turned A$3k into over A$6k.

Did you always have a goal of starting a business with your investment, or was there another plan when you first started?

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!

Have you started investing again?

No, 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 you buy, sell or hold?

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 react when you first 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 and remove yourself from checking your portfolio every day and when a stock does dip just try to understand whether it’s because the entire market dipped or if it’s something specific to do with the company. 

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

What advice would you give your younger self just before they made their first trade?

Take bigger bets. Focus on making money first and 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.

Finally, describe how it feels 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. 

This is not financial advice nor a recommendation to invest in the securities listed. The information presented is intended to be of a factual nature only. 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.