The Intentional Investor is free for everyone to access. You can grab the mp3 file below, or you can subscribe at:
From bagpipes to bouncing to betting markets, Andrew Mack’s journey to becoming a successful trader and sports bettor is anything but conventional. In this deeply personal and wide-ranging conversation, Andrew opens up about the detours, doubts, and decisions that shaped his unlikely path from rural Canada to algorithmic trading. Along the way, he shares what working in oil fields, selling used cars, and studying sociology taught him about risk, discipline, and finding conviction in uncertainty. This is a story about reinvention, self-reliance, and the grit it takes to build your own edge from scratch.
you get it here first - my notes and 3 big takeaways for work, life, and legacy, straight out of m time with Andrew Mack:
Do you know Andrew Mack? The bagpipe-playing, electrician-turned-options trader who sports bets the market and built himself from rural Ontario log cabin to financial independence through pure grit and intellectual curiosity?
If not, allow me to introduce you. Andrew has navigated everything from nightclub bouncing to oil rigs, from law school to data science, ultimately finding his edge in applying sports betting methodologies to options trading. I wanted to connect with him because he embodies something I value deeply: the relentless pursuit of self-mastery through unconventional paths and the courage to keep iterating until you find what works.
Our conversation is LIVE now on the Epsilon Theory YouTube channel (and this Cultish Creative Playlist). Listen and you’ll hear Andrew’s wild journey from playing bagpipes in rural Canada to “sports betting the options market” and building genuine momentum after years of grinding through dead-end jobs.
In the meantime, I wanted to pull THREE KEY LESSONS from my time with Andrew to share with you (and drop into my Personal Archive).
Read on and you’ll find a quote with a lesson and a reflection you can Take to work with you, Bring home with you, and Leave behind with your legacy.
WORK: Exit Velocity Requires Extra Push
-Andrew Mack, The Intentional Investor on Epsilon Theory YouTube
Key Concept: Breaking free from your current circumstances requires extraordinary effort beyond what’s needed to maintain the status quo. Andrew learned that reaching “exit velocity” - the thrust needed to break gravity - meant putting in extra hours every single day when he was already exhausted from physical labor. This principle applies to any career transition: if you want to move to a new stage of life, you can’t just do the bare minimum. You need sustained, focused effort in your off-hours to build the skills and knowledge that will eventually lift you out of your current situation.
Personal Archive Note-To-Self: I’ve written about it before, but the question that helped change my life was, “How am I complicit in creating the things I say I don’t want?” This is true in regular life, but it’s really true - and probably easier to fix/troubleshoot - in work life.
The big trap is if you are just waiting for a meritocratic promotion. You can be doing all the things somebody else tells you to. You can be investing all of your time and energy and sanity into playing by the rules. You can be - let’s call it what it is - orbiting their planet and playing by the stated rules of their gravity, waiting to be cleared by someone else for liftoff even though you know you’re ready, and guess what? You’re stuck until they make the decision, no matter how rocket-fueled up you are.
When Andrew talks about figuring out how to achieve exit velocity, he’s not just talking about the speed to do it. He’s talking about the choice too. And, choices are hard, but if you can combine them with agency and a direction, you’re headed off to new horizons.
Work question for you: What extra hours could you dedicate each day to building skills that would create exit velocity from your current professional constraints?
LIFE: Identity Beyond Any Single Thing
-Andrew Mack, The Intentional Investor on Epsilon Theory YouTube
Key Concept: True resilience comes from recognizing that you are more than any single identity or role. When Andrew’s hockey career ended due to injury, he faced the painful realization that he had built his entire sense of self around being a hockey player. This forced reckoning taught him that sustainable identity comes from adaptability and growth rather than attachment to any particular skill or position. The lesson extends to all areas of life - whether you identify as your job title, your relationship status, or your achievements, real strength comes from knowing you can reinvent yourself when circumstances change.
Personal Archive Note-To-Self: Sometimes you choose to change. Sometimes you’re forced to change. And even in those latter examples, if you are stubborn - and listen, I can be s-t-u-b-b-o-r-n, so I get this deeply - it can still be hard to choose to change even when life is forcing you to.
I’ve lived in crappy situations. I’ve worked with and for crappy people. I’ve channeled all the good-guy tolerance tips my church-going upbringing planted in my head. It’s not a bunch of hooey. It serves a person well, most of the time.
But sometimes, when life breaks you, and you have to admit it, you have to admit you can’t go back either. You should go back and really listen to Andrew tell this story. Versions of it play out over and over for him. Life is daring you to change, and sometimes you have to start to change before you know what the new identity is, and maybe THAT’s one of the hardest truths of our entire conversation.
Sometimes you just don’t know. Sometimes you just have to make a bet, and see what happens. And then, learn something, and do it again.
Life Question For You: What single identity or role are you overly attached to that might be limiting your ability to adapt and grow?
LEGACY: Turning Your Mind On Again
-Andrew Mack, The Intentional Investor on Epsilon Theory YouTube
Key Concept: Sometimes life beats you down to the point where you stop engaging intellectually, but the right challenge can reignite your curiosity and analytical thinking. Andrew’s experience with electrical trade school and law school reminded him of his intellectual capacity after years of grinding through manual labor jobs. The key insight is that “turning your mind on again” often happens when you find subjects with objective standards and clear problem-solving frameworks, rather than subjective exercises in regurgitation. This intellectual reawakening becomes the foundation for everything that follows.
Personal Archive Note-To-Self: Learning is a muscle. When I’m writing these posts spread out over a week or so, and not just cramming them down onto a page, or, when I take two weeks off (rare) and then have to dive back in, I can feel the atrophy.
The best thing to remember is - you can turn it on again. We all know people in our lives who have shut it off. People who have gone complacent, for a short period of time or for a long period. But, while you can’t force people out of complacency, anyone can come out, so long as they’re still alive.
In Andrew’s case, when he started, it’s almost like he couldn’t stop. Electrical training turned into law school turned into programming turned into all the stuff he does now. That’s exit velocity again. It’s opting in to whatever choice you want to go for, saying goodbye to whatever comforts you had before, and hurtling off into space determined to make a future out of your life that you want to live in.
Legacy question for you: What area of learning could you explore that would challenge you to think rigorously and potentially reignite your intellectual curiosity?
BEFORE YOU GO: Be sure to…