The Game

January 10^th, 1991. That’s the earliest reconciliation I've had since I first started following this game—the game that is markets, investing, and finance. That was my first recording in the “Notebook.” 

The hard-to-read handwriting stated: 

“Yesterday, the down payment on a house was reduced to 5%; also, yesterday, the Toronto Stock Market climbed 65 points, the most in 4 years.” 

From that early age, something about numbers, stocks, investing, and seeking edges captured my attention, and I became hooked on the game. It must have just been in me from the start. The process has evolved over the years, but the notebook, measuring and mapping macro, and the data points have been a part of how I play the game for a long time. 

I did not grow up in a financially literate home. My parents were educated at a university, but were hardly educated about the realities of the economic world. My mother was a social worker, and my father was a gym teacher. They saddled themselves with a high-priced mortgage that their fixed, fiat income salaries as civil servants could not afford, cosigned by their grandfather as a means for the Bank to say okay. 

As a kid, particular events stand out to you and shape you for who you will be and how you think about life. My parents separated and divorced around the time of this journal entry in 1991. My mother cared deeply for me and my sister and did her best to raise us, trapped with the debt burden of a single mother trying to run a house that required two more of her income. 

I vividly remember my mother repeatedly writing her monthly budget on the dining room table to make the math work. Her visible frustration and the toll it took on her mentally were evident. The math was never going to balance out, no matter how many different times she tried to write it out. 

Before I ever owned a stock, I learned from the kitchen table’s relentless hunt for balance and margin between what you have and what you need. 

Grade 9 was my favourite grade in school, and it stood out for one main reason: it has had a lasting impact on my life since then. We had a social studies course taught by a vibrant, energetic man, Mr. Stacey. 

The main project of the course was a 10-week mock stock market challenge. We were put into groups of four and set up a mock trading account to compete against other groups. Competition has always motivated me.

You have to remember that back then, there was no internet, no YouTube, no instant stock quotes, and no market coverage like today. 

Our research involved obtaining the daily paper, where every stock traded on the Toronto Stock Exchange had the prior day’s closing price printed in long form, including volume and 52-week high and low.

We would track the companies we chose to buy and our performance over the ten weeks, following companies we were interested in the media. Back then, that was our Bloomberg, our trading view. 

In that Stock Market competition for grade 9, I had yet to learn how my group had finished, but I was hooked. You can invest money in a company, and its value could increase. 

A way to freedom that wealth provides outside of a 9-5 job. No one had ever explained that to me (as they didn’t know). Most people thought having a “good job” was the ultimate goal. A government job was the ticket for >99% of the people in my community and family during the 1990s. 

After completing that course that year, I begged my mother to let me open a trading account. TD Waterhouse was the brokerage firm. I remember filling out the paperwork. I was <16, so I could not open the account independently, and my mother had to be the account holder. I put in about $400 at the time (trading commissions back then were ~$49), which was a lot to get going. 

You always remember you’re first. The first stock I bought with real money was Arizona Star Resources. It was a junior exploration company that I had read about in an investment newsletter, the Investor's Digest. The company ended up 4 to 5 times what I had bought it for, and that was it; I had my winner and some dollars to buy more stocks.

I don’t recall the names of other stocks I went on to buy, but they were probably also in the resource sector.

From then on, I knew I wanted to pursue a career in the investment industry. There wasn’t anything else that spiked my interest. 

There was a great Canadian TV show from 1996 to 2000 titled Traders. It profiled the fictional investment bank, Gardner Ross, on Bay Street. The show had everything for finance junkies pre-YouTube, pre-Twitter. They had a trading floor with a loud, obnoxious head trader, a brilliant autistic quant, and a merchant bank division. Looking back now, I realize this show was so good for its time. I saw myself one day working at a Gardner Ross. 

ARBITRAGE: 1998 was my last year of high school. I was a good student, with a mid-to-low 80% average. I wasn’t the top in the class by any means, but I did love math, and we had some great math teachers. 

Our school had two different math classes, both teaching similar curricula, but one was labelled an advanced course, focusing on pre-university concepts, and the other was academic.

I was in the same courses as all the students in the advanced course, and we all took an additional statistics course. However, I noticed a $500 scholarship for the top math average in advanced math and the same for academic math courses at the beginning of the school year. Signing up for the academic math course would put me at no disadvantage for starting university, but I knew I’d never beat the top students in the advanced course for the $500. 

#Edge. I beat another guy by 2 points to earn the top average and $500 in academic math that year. More money I could then put toward my investing account. I bet the person who got 2nd second-highest mark in the advanced course doesn’t even remember today. 

You don’t think you have an edge? Create one. Everyone has something that makes them unique on this planet, and the more influences you have, sometimes it’s easier to see then what you’re edge really is. 

I undertook a business degree at university. With business degrees, you can focus on various concentrations: marketing, human resources, technology, accounting, and finance. There was no doubt that I would pursue a career in finance. It had all the courses I wanted: finance, international finance, options and derivatives, etc. We had a great professor in our small group, Dr. Alex Faseruk, who was the foremost expert on options and derivatives in our area. The guy used to get downright giddy about put/call swap spreads and strategies. It was fun. Our finance group was small (<20) compared to the overall B. It's a community class, but many of those guys went on to have high-profile investment careers on Bay Street (Colin, Steve, Aubrey, hi, hope you’re well). 

I took a different route. I didn’t want to live in Toronto in 2003 for $ 38,000 per year (the average starting salary). I took a job as a small loans officer for an economic development organization in the exact opposite of North America, in Inuvik, NT, where it’s fully dark for two months of the year and sunlight for two months in the summer. It was a great learning experience because I had an old-school boss, and we even handled repossessions when clients stopped paying. I was exposed to the oil and gas industry's natural resources and travelled to the most isolated communities in Northern Canada, places I would never have reached. 

The next step was transitioning into a commercial banking role, where I worked with entrepreneurs, analyzed cash flow and balance sheets, and gained insight into the realities of managing an enterprise through a lender's lens. 

The investing game was always part of my journey as a banker, and I viewed every file not as a banker, but as the person borrowing the money to put capital to work myself. I viewed my clients as people from whom I could learn. 

Trading financial markets is the ultimate game you can play. There is no finish line or set of rules to define the game. The game is constantly evolving, and as such, you need to grow with it to stay in the game. It’s not you against other players; it’s you against yourself. 

The process evolves from traditional finance education and knowledge to how markets work and the power of the “machine.” A science, math-based approach is better than a narrative approach.  More than ever, the game is driven by flows, volatility and a rules-based approach of the machine.

My first stock wasn’t from some “guru” on CNBC, but from the pages of a print newsletter long before streaming tickers and YouTube trade tips. Grade 9’s stock market challenge set my hook, and I’ve been chasing edges, making trades in all areas of life and learning from my constant mistakes ever since. 

Embrace the suck. That’s really how you survive and thrive playing the game. Humility will come from challenging tasks in life, like hunting big game (moose), doing bodybuilding competitions or trading with your family’s hard-earned capital in the market, competing against yourself. Tough and challenging things have always been fruitful for me and my passions. 

No uncle at the bank. No “big break.” Just curiosity, competition, and the thrill of the most excellent game there is: investing. 

Today, Dragon Fly Capital enters its new chapter.

My mission is to share my journey, real lessons and an honest map for anyone who loves the game - no matter where you’re starting from. 

The ‘Notebook” is still open.

The rules are constantly changing. That’s the game. 

Every investment decision—win or lose—became a line in my own version of the “Notebook.” Over the years, those pages filled up with stock charts, lessons, market obsessions, missed edges, and the hard-won insights that you don’t get from books alone.

I’ve learned the real value in this game has never been the dollar amount on a brokerage statement, but the process of staying curious, resilient, and honest with yourself.

You’re never playing against the market—you’re always playing against your own impatience, overconfidence, and fear.

In the end, investing is the most excellent game because it’s never mastered. The rules change with every new cycle, every innovation, every unexpected headline. The game will humble you and, on the best days, reward you with clarity and purpose.

That’s the spirit behind Dragon Fly Capital: sharing the ongoing journey and opening the Notebook. Mapping out the macro, learning from the numbers, and never pretending there’s only one way to play. This isn’t about being perfect—it’s about continuing to evolve and love the challenge of the game.

Whether you’re just starting, coming back after a harsh lesson, or searching for your next edge, I hope Dragon Fly Capital gives you something tangible to carry into your own game. Because the pursuit never ends—it only gets richer.

Here’s to the love of the game, and to playing it our way.