From Beer Kegs to Business Deals: My Winding Road Through Entrepreneurship
I never planned to be an entrepreneur.
I wasn’t slinging lemonade as a kid or flipping baseball cards in high school. Starting a business felt completely foreign and not something I was destined to do. In fact, the idea didn’t even cross my mind until my final year of university when a friend said, “We should start a business.” And fatefully, I said yes.
Since then, entrepreneurship and I have had the kind of relationship you’d warn a friend about. It’s been passionate, chaotic, fulfilling, and at times, soul crushing. We break up. We get back together. And somehow, we always find our way back to each other.
This is the story of how I stumbled into startups, burned out hard, bounced between ideas, and eventually found myself in a career I never expected, helping other entrepreneurs sell their businesses and move on to whatever’s next.
How I Accidentally Became an Entrepreneur
As I rushed through my last stages of undergrad at University of Ottawa, I was eager to be done with the impractical rigmarole of academia and start doing something in the real world. I had no idea what that looked like and my good friend, Adrian, and I had talked for the last year about how we should start a business one day. But it was simply a hypothetical notion and we had no concrete ideas at that time.
Adrian had been doing some design consulting for a craft brewery outside of Ottawa and one day they approached him about a problem they were having: tracking kegs.
Huh?
That was my response at least. In a nutshell, breweries mostly own their own kegs and send them off to bars and restaurants all over their region and beyond and want to get them back as quickly as possible so they can send them out again. They typically rely on spreadsheets, whiteboards, and a prayer that these $100-$200 assets will make it back to their brewery. Average loss rates in the industry are around 5-8% per year so if you have thousands or even a few hundred kegs, these are not insignificant losses for a small business. While figuring out ways to fix this problem, we quickly realized that breweries all over the world were having this same problem and no one was solving it particularly well.
So we got to work and started to build Kegshoe.
We built a basic version of the product in five months. After eight, we had our first customer. Being tied into the university ecosystem gave us access to grants, pitch competitions, and early investor interest. It was exciting. For two undergrads who liked craft beer and wanted to build something, it was perfect.
We were suddenly making big decisions like where to base the company, who to pitch, what kind of business we wanted to build. It was the height of the craft beer boom, and “beer tech” was hot. Investors wanted in.
Burnout Doesn’t Care About Your Business Plan
And then I broke.
Just as we were finalizing plans with investors and outlining our next big growth moves, I hit a wall. I spent an entire long weekend in my room in Ottawa, unable to write a single email. Every time I opened my laptop, my heart would race like I was about to give a TED Talk in my underwear.
I actually Googled: “Why can’t I write an email?” The answer: anxiety and panic attacks.
And so began the journey (that still continues to this day). I moved home with my parents in BC for the summer and we tried to reset my nervous system. All business plans were put on hold and Adrian took the reins to keep the wheels rolling on our keg tracking bus as best he could. I spent my days in nature, searching for calm in the mountains, lakes, and trees. From the outside, it looked like a peaceful summer. Internally, it was chaos.
This drastically changed the course of my entrepreneurial journey. Though we tried to regain momentum over the years, my capacity for a high stress / high pressure environment just wasn’t there. I needed to find balance and healthy equilibrium between work and life. I was not destined for a Silicon Valley, hockey-stick-growth, life. In hindsight, I’m grateful for that. Though I didn’t expect to hit my wall so early in life, it taught me huge lessons on what I truly value in life.
Throwing Spaghetti at the Business Wall
Though Kegshoe continued to run slowly and steadily in the background, I wasn’t convinced the entrepreneur life was for me. With my newfound discoveries on work-life balance, a standard 9-5 where I would actually get paid and have weekends off sounded dreamy. I managed to find a job helping a local Vancouver privacy consulting company that wanted help growing their business. It was perfect. I got to help someone grow their company while getting a steady pay cheque.
But after two years, I was getting bored. I was feeling that familiar draw back to the self-employed world where you had control over your own destiny.
Though my passions don’t lie in keg tracking, I tried different avenues like starting a cleaning company, explored dehydrated meals for backcountry campers, and chased a handful of other ideas. Some worked, most didn’t, but nothing lit me up enough to fully commit.”
I was in an epic battle of Pong getting bounced between boredom and overworked, unable to find the right fix of something I enjoyed doing and challenged me while still having a balanced lifestyle.
Despite my restlessness, health continued to play a major role in my day-to-day life. What started as an uneventful bout of COVID in 2023 turned into an ongoing case of Long COVID. It’s a story for another day, but it’s been a constant battle between rest and restlessness. A tough balance in entrepreneurship-land, but one I was determined to find.
Buying a Business Sounded Easier on YouTube
For the longest time, I’d thought about buying a business. I’ll admit, I got sucked into the influencer algorithms around “boring businesses” that generate cash flow with little to no money down. But I genuinely loved the idea of bringing what we’d learned from growing a software company into local, service-driven businesses. The kinds that quietly power our day-to-day lives. There was something poetic about it.
For about a year, I was your typical passive searcher just hoping an opportunity would jump up, slap me in the face, and say “buy me!”.
As anyone that has bought a business knows, it’s pretty darn hard to find an opportunity this way. I signed some NDAs, talked to a few business owners, but literally had no idea what I was doing. Probably the thing that surprised me the most though, was the diverse array of crap that came to me when I wanted to learn more about a business. For one business in particular, the real estate agent representing the business, simply sent me the business’ tax return. It blew my mind. There were so many solid businesses out there that have good reputations and generate cash flow but it was impossible to get a good understanding of the business. There were some business brokers posting businesses but the quality and consistency of their listings varied widely.
Welcome to the Wild West of Business Brokerage
After months of aimlessly browsing listings, signing NDAs, and getting half-baked info from sellers and realtors, I started wondering if the entire world of small business sales was just... broken.
The quality of listings was all over the place. Brokers ranged from unresponsive to downright shady. In one case, I asked for financials and got a single tax return from a real estate agent who clearly didn’t understand how to sell a business. It was baffling.
I wanted to learn more, not just to buy a business, but to understand why this space felt so opaque. That curiosity led me down a rabbit hole of research, conversations, and eventually, a deeper involvement in the world of business brokerage.
The more I learned, the more obvious it became: this industry is still the wild west. In Canada, literally anyone can call themselves a business broker. No license. No training. No standards. And unfortunately, that means a lot of business owners get bad advice or walk away from the process frustrated and disillusioned.
But as I dug deeper, something clicked. I realized this might actually be the space I’d been looking for. I had this weird mix of skills of entrepreneurial experience, founder empathy, and a genuine love for small businesses. And this was one of the few roles where that mix actually mattered.
On paper, it checked a lot of boxes:
There’s a massive wave of retiring owners with no succession plan.
Most entrepreneurs have no idea how to sell their business and no one’s really teaching them.
The space is ripe for disruption but still deeply human and relationship-driven.
I wasn’t drawn to high finance or private equity. I wanted something more grounded.
And even if it didn’t stick, I’d learn how to buy a business the right way
But beyond the logic, it just felt right.
Eventually, I found myself working with a team that shared those same values. The team at Chinook Business Advisory were focused on building trust, improving the process, and doing right by the founders they work with. That alignment was what sealed it for me. Because I’ve come to believe that when you put people first, everything else tends to fall into place.
Why I’m Writing This
I’ve spent the last eight months working with a great team, helping business owners navigate the often murky process of selling their companies. I’ve closed a handful of deals and I get to spend my days in conversation with entrepreneurs, helping them make sense of one of the most important decisions of their careers.Outside of that, I still run side projects and continue to support Kegshoe, which helps hundreds of breweries manage and track their assets.
I still hesitate to call myself an entrepreneur and still struggle to concisely answer the “what do you do for work?” question. There are plenty of flaws in capitalism, but building something useful, working on your own terms, and having the flexibility to explore new ideas? That’s hard to beat.
Entrepreneurship can be a bitch, it can whittle you down to your bones, and is not for the faint of heart. But it can be equally rewarding and freeing. You don’t need to make the next Facebook, work 100 hour weeks, or even feel like you’re a natural-born entrepreneur just to build something fulfilling and sustainable.
Through this writing, I’m aiming to pull back the curtain on what it’s really like to buy and sell small businesses and to share what I’m learning about entrepreneurship, health, and life along the way. Thanks for reading. I’ll be posting every couple of weeks. Some posts will be business-focused, others more personal, but always honest, and hopefully useful.
If you want to talk about buying businesses, selling businesses, or tracking beer kegs, there’s a good chance I’m the only person oddly qualified to do all three.
