Giving thanks for 20 years of entrepreneurship

At 17, I was homeless. At 37, I’m filming a TV show, "Building A Billion-Dollar Business". Here’s what 20 years of entrepreneurship taught me about winning—and what really matters. Today I'm giving thanks.

At 17, I registered my first business while homeless in downtown Victoria, Canada. I lived between a friend’s car parked in a field, park benches when I was too tired to walk out of downtown, and a day-rate hostel dorm whenever I could scrape together some cash.

I survived on dollar-a-slice pizza, showered at the YMCA on a donation pass, and took whatever day labor I could find. When I turned 18, I secured a $5,400 student loan, quit college before tuition was due, and went all-in on my first business. Was it risky? Absolutely. Am I proud of it? Not really. But it worked.

I'll never forget the one and only time I went to youth counselling. I was frustrated with myself that I couldn’t make enough money fast enough to afford a place to live by the time college started, and maybe actually stay in school, and get a laptop to study and work. I wanted to talk to someone, process it all, and figure out a plan.

The counselor started by asking, “When was the last time you had a shower?” I told her, “Three days ago, at the YMCA.” Then she asked where I lived. “In a friend’s car parked in a field,” I said. “But sometimes I stay at the Turtle Inn downtown if a 4-hour cleaning shift is available to swap for a free night stay.”

When she asked about my plan, I told her straight up: “I’m going to drop out of school and use my student loan to start a business. But please don’t tell anyone. I might find a way to double the money in the next few weeks and stay in school”

She just paused, then laughed—not in a dismissive way, but in this peaceful, encouraging way that caught me off guard. “Do you realize how much you’re doing and trying to handle right now?” she asked.

I shrugged, not knowing how to respond.

Then she said something that’s stayed with me for the rest of my life: “You should absolutely not be hard on yourself. Do you know that you're doing way more than you think?”

That simple statement and Jedi-reversal-question became an anchor for me. Amidst all the chaos of entrepreneurship and life, it’s a reminder I hold onto: Don’t be hard on yourself. You’re doing way more than you think.

The drive to win at all costs feels absolutely insane looking back—but it taught me resilience. And trust me, I’ve had more epic failures than I can count.

For fun, here are a few of the more creative ones:

I decided to fly to Kazakhstan over Christmas, lock myself in a hotel for two weeks, and write a book called Sh*t Creek as a gift to myself (inspired by The Alchemist author Paulo Coelho, who apparently did something similar) and ode to the roundabout journey of life involving entrepreneurship. It sounded poetic until I discovered the TV show Schitt’s Creek launched around the same time—buzzkill on my title. Then I started reading Anthony Kiedis’s Scar Tissue, and it turned me off from publicizing all my failures. Double Entendre Fail.

Then there was the time I bought a shoebox full of weed from a Trinidadian, thinking I could low-key flip it on public buses and double my money. I didn’t even smoke, so I couldn’t answer any stoner questions (KYC = Know Your Customer). Fail. Stupid, illegal, and embarrassing.

Or the time I decided to import discount clothing from Bebe and resell it in Facebook groups back in 2007. I made a ton of money... until I got sued by Bebe New York for not owning a store or distributorship. They forced me to give back all of the inventory, even though I technically bought it all from them, so instead I donated all of these high end winter jackets and clothes to the women's shelter. I wrote Bebe a letter and sent them the pics to sympathize. Law suit went away, but I was all-in and knew zilch about diversification. So 100% gains and principal fail.

At 19-20, I moved to Thailand to DJ, teach English, and side hustle exporting Billabong factory board shorts, all while running all-ages parties and concerts back in Canada with high schoolers as promoters. Some pretty awesome lifestyle wins on that one, for a minute, but in the end? Someone got stabbed at an event, brand reputation damages, major lack of focus, and unreliable high-schoolers! Who knew?! Messy fail. Moved back from Thailand to hunker down on the concerts business and get serious about scaling it.

And how could I forget: At 21 years old, I was dating a girl for three months, and watched the movie 'Into The Wild' (my favourite movie forever since). It was based on the autobiography of Christopher McCandless "Alexander Supertramp", and written by Jon Krakauer, who also wrote the book 'Into Thin Air', about the deaths of his guides during a Mount Everest expedition. I fell in love with a quote in the movie, and the concept of, "the climactic battle to kill the false being within and victoriously conclude the spiritual pilgrimage". I was utterly moved to leave everyone and everything like McCandless did. So I told the girl I wanted to move to Nepal to go live with sherpas and train to climb Mount Everest. She dumped me. I went and bought mountaineering equipment and a one-way ticket to Kathmandu. Park fees, gear, flights and living was all-in $30,000, and I had just the right amount saved.

My business at the time was promoting concerts, and things were going well. Then, just weeks before I was set to leave for Nepal to climb Mount Everest, I got the news: the #1 independent hip-hop artist, Tech N9ne—someone everyone had been asking me to book—accepted my bid for three nights on tour. At $11,000 per night ($33,000 total), he agreed to perform in my region as part of his international tour.

It felt like a dream come true. I saw the opportunity to invest my "Everest money" into the show, double it, and still fund the climb right after the tour. But suddenly, I was stuck between two dreams: one professional, one deeply personal. Everest had become a full-blown obsession for me, and the girl I was dating had already broken up with me over it (understandably, since I vowed to leave for longer than we had been together). I was all-in on the mountain.

But in the end, I canceled my ticket to Kathmandu and decided to take the risk on the show. I poured everything into promoting it, traveling all over Vancouver Island and going as big as possible. I rented an outdoor speedway and headlined Embrace Fest with Tech N9ne. The night was a huge success—grossing over $100,000!

And then, disaster.

That same night, all of the cash was stolen from the registers.

In an instant, everything I’d worked for was gone. I had to forfeit my trip to Nepal, sell and return all of my mountaineering gear, and use every penny to pay off some of the vendors, staff, and artists. Even after that, I was left with massive losses. My savings were wiped out, and Everest was officially off the table.

With no other option, I moved to northern Alberta and worked on the oil rigs for a soul-crushing year to pay off the debts as fast as I could. I quit the rigs the exact same day I sent the final payment to TD Bank on my line of credit. Walking away with $0 to my name, I found one small silver lining: I still had an $8,000 credit from a deposit I’d made for Warren G to perform on a leg of his tour in Victoria and Campbell River.

I left the rigs, finished out the Warren G tour (shoutout to #Regulators), and that was one of my last events as a promoter. From there, it was onto the next chapter: starting an advertising agency.

It was a major epic fail, but also the beginning of something new. #NextBusiness. #Resilience. #Entrepreneurship.

At the time, all of these failures felt like the end of the world. Gut-wrenching, painful experiences. Like when you lose everything you have, and worked so hard, and you still owe people money and have to work more just to get back to zero, it feels like nobody can possibly understand what's going on. But looking back on it all, these experiences build something far more important: resilience.

Now, as a parent, I sometimes wonder how I’ll teach my kids that kind of resilience. It seems impossible to reproduce the positive impact of failure without putting them through the same pain and hardship—and that’s not exactly something I’d want for them. Resilience, it seems, comes with a steep price.

Fast forward 20 years to today: I’ve been fortunate to travel and spend time in 6 continents and 45 countries (I even had a free trip lined up to Antarctica this year to film a TV show, Travel by Dart, and finally tick off that 7th continent—but missed it because of... the business!). Along the journey, I found and married an incredible woman, the love of my life and we've welcomed two beautiful daughters into the world, and I can now say I have an actual home for all of us to live in. Safe to say my girls won't be sleeping on park benches. But the thought of that is now an

Absolute. Mind. F*ck.

To think that all of what we have in life, in some way or another, relies on the businesses and networks I’ve been able to co-create throughout many of these trials and tribulations—and with such unbelievable support and faith of others helping me to exist, let alone succeed—is beyond humbling. If it takes a village to raise a child, then I am the living, breathing example of what a village can do. From living on food donations and welfare for so many years in my childhood upbringing, to free places to stay in my youth and adulthood, even, to investors who’ve now trusted me with millions of their hard-earned dollars (God, please bless them all and return it to them a hundredfold through Napkin Inc. ), I am infinitely grateful for the grace and provision and all of what has carried me throughout the years.

But here’s the truth:

Time and health are the real currencies to count. Family and love are the real measures of ROI. Everything else must now work to serve those purposes.

It has taken me 20 years to realize this. I literally thought about it and it all clicked just yesterday, watching my wife walk my eldest daughter into hip-hop dance class on a -17 below Celcius Wednesday night in St. Albert. I actually cried as though a manifestation of love took over me in a moment. Enough to make me entirely reflect on life and write this post. Juxtaposing what I have with what I 'deserve' blows my mind. I am in absolutely no ways a rich person in terms of dollars, at all, but I have chased money endlessly without regard for health, family, or security, and it has been such a gamble. I’m finally at a place where I’m striving to find balance—not just crushing goals, but nurturing my family, my health, and a good amount of time spent now focusing on my faith.

To some people, entrepreneurship is like a drug. It fills all kinds of holes you wouldn't even think or guess existed. The risks can catch you big-time and end in ruins. Two people I know deeply, have indeed ended their own lives due to financial hardships -- one caused by their business failing, when few had any idea of it and would have gladly helped. A note was written and found, and in reflection, having more of either of the two, Time and Health, would have rightfully kept both of them alive.

Here’s a few things I’ve learned along the way, to help make life easier moving forward:

1. Health and faith over hustle. Treat your body like a temple and align your work with a higher purpose. Your eyes are the lamp to the soul—what you watch, read, and expose yourself to impacts you more than you realize. Positively charge your energy. Everything is connected, and nothing is exactly as it seems. The real battle isn’t between flesh and blood, but between spirit and spirit. Hustle all you want, but remember this: God knows your heart and exactly what you need to feel blessed and loved. When you connect with faith, your hustle naturally shifts to serve you better—not the other way around.
2. Work smart, not just hard. There are levels to this game. Learn to hire, delegate, plan, and prioritize self-care. And for the love of sanity: take a vacation. I just took my first real vacation in four years (and I’ve been married for five). Idiot move on my part—I should have done this WAY sooner. Here’s the thing: there’s never a “perfect” time for a founder to take a break. You think, “As long as I have investors, I can’t rest until they exit,” right? WRONG. They want you at your best, not as a burnt-out shell barely holding it together. Not to mention, my spouse is an absolute saint for putting up with me and my ‘for the business’ excuses—the endless trips away, the all-nighters, the constant grind. It’s crazy. But here’s the truth: the business has to work for you, not the other way around.
3. Rest isn’t optional; it’s mandatory. Rest is fuel. For the past ten years, I’ve practiced Shabbat—24 hours of no work from Friday sunset to Saturday sunset, wherever I am in the world. (Okay, except the North Pole—true story, I was filming a TV show in Svalbard over Christmas, where it’s dark 24/7, so that one was a bit tricky.) But seriously, Shabbat has been a game-changer for my life and my business. That weekly “reset” recharges my energy, creativity, and focus in ways I can’t fully describe. After a week of rejections, cash-raising stress, customer chaos, staff issues, and acquisitions, Shabbat brings an almost supernatural level of clarity and peace. It’s like hitting the Omg button—literally. The metaphysical connection of resting in God’s presence and finding strength in His embrace is fuel like no other. That one day of rest primes all the essential entrepreneurial muscles—faith, creativity, steadfastness, strength, and patience—for the week ahead. If you haven’t tried it yet, I can’t recommend it enough. Faith and intentional rest will guide you in ways hustle never can. Shabbat isn’t just a reset; it’s a revelation.

All this to say: hard work can literally take you from homelessness to your wildest dreams, but if health and family aren’t part of those dreams, it’s all pointless. The grind without balance is just gambling on borrowed time.

To my fellow entrepreneurs and hustlers: Please don’t let the rat race steal what matters most. Build your success on a foundation of health, family, and purpose. Even if you're young, family isn't just marriage -- it's your sister or brother; or a friend in need that will have your back in 20 years from now; or your parent who's dying to talk with you because you're an entrepreneur and have been such an *sshole to them for God knows how many years (sorry, mom, if you're reading this) all for the sake of your business. The hamster wheel is always going to be there, no matter what. You can hop on any time. Investors, staff, clients, they are always there and happy to harass you whenever you want! Just be chill. And always remember, "you should absolutely not be hard on yourself, you're doing WAY more than you think".

Tell me how this made you feel in the comments. Should I keep these posts coming? I don't know. Feels like someone out there needs it right now. Whoever you are... you got this.

Love you!

#entrepreneurship #growth #health #family #faith #leadership Napkin Inc. #happythanksgiving