As a kid in Ottawa, I’d cut the flowers from my mom’s garden, bundle them into bouquets, and sell them to passersby. I went door-to-door down my street, trading old toys for pocket change. On family road trips, I ran a “convenience store” from the back seat, charging my parents for the very snacks they packed. Thankfully, they nurtured my business instincts instead of shutting them down.

This eventually led me to study at Babson College, known for its hands-on approach to teaching  entrepreneurship. I wanted real experiences–not just lectures. In my freshman year, I launched a small business selling promotional goods for conferences, forcing me to learn pricing, margins, and customer empathy the hard way. But by graduation, I didn’t have an idea worth devoting the next decade to, so I chose another training ground: investment banking.

Banking promised a crash course in how companies are built and valued–and it delivered, at first. After a year, though, the learning curve flattened, and the limits of my U.S. visa began to weigh on me. I wanted a different path, where I could be closer to operators, customers, and the messy decisions that make or break a business.

That opportunity came when I connected with  a marketing firm producing videos and TV spots for major brands. The company had traction but struggled to turn one-off wins into recurring revenue. I moved back to Toronto and eventually led its day-to-day operations, building a solid portfolio of retainer clients. Through this role, I gained invaluable experience in production, operations, and logistics, while deepening my understanding of customer satisfaction. 

In 2016, a friend asked me to help buy a used car—an experience that became the catalyst for Clutch, the online car retailer I founded that same year. As a lifelong car enthusiast, I happily obliged. What followed was dealership hell: inconsistent information, questionable pricing tactics, and salespeople more focused on their commissions than helping us find the right car. 

Around the same time, we signed a large automotive lender as a client at the firm. To better understand the industry, I visited dealerships with our new clients and realized how broken the system was. General managers and sales leaders openly discussed the tactics used to move cars quickly and profitably, showing little concern for customers. Having just been on the buyers’ side, I was appalled at how undervalued buyers were in the industry. 

I knew there had to be a better way. I envisioned a truly integrated process, where cars were inspected and reconditioned to high standards before listing, a sleek interface that made car buying as easy as ordering on Amazon, and a money-back guarantee to give customers confidence.

I pitched the idea to the lender–they recoiled. The model would compete against dealerships that supplied nearly all their leads. If the incumbents wouldn’t make the leap, I decided I would.

I lost count of how many times I heard “Online sales will never work.” The industry doubted the idea, but I forged ahead anyway. I raised a small family-and-friends round, hired a small team, and conducted extensive user research to build a minimum viable product. We applied for a dealer license in Ontario and waited eagerly only to have our momentum stall when the application was rejected. 

I knew the idea was promising. I just needed a jurisdiction that would let us prove it. I looked for places a short flight from Toronto, with business-friendly regulations and enough population density. That pointed me to Halifax, Nova Scotia. I booked a one-way flight and, for the next nine months, it became home.

Now licensed, we faced just one problem: no cars to sell. Capital was scarce, and the best debt line I could secure was $50,000–personally guaranteed. We needed inventory to show customers, but I couldn’t outbid dealers at auction or afford to carry dozens of cars on my balance sheet.

So, I turned to the private market. I found myself in people’s living rooms, pitching what sounded like a crazy idea: hand over their car and ownership documents, which I’d take to a storage facility they’d never seen, recondition it, and offer it for test drives by strangers. When the car was sold, we’d split the profit. To my surprise—and eternal gratitude—enough people said yes.

Our first car buyer was Barry from Sydney, Nova Scotia. He bought a 2010 Toyota Corolla for his daughter. I delivered it to their home myself. That first sale was proof the model worked.

I quickly realized how capital-intensive growing the business would be, requiring substantial equity to buy, recondition, and deliver vehicles. Most investors told the same thing: Clutch was too asset-heavy for venture capital and too capital-intensive to grow. They urged us to pivot to a lighter “marketplace” model that looked like a better classifieds site. But the real value lay in controlling every step of the process. By managing vehicle quality, reconditioning, pricing, and the customer experience end to end, we could make used-car buying simple, trustworthy, and transparent. 

In early 2019, we raised capital from several venture funds. By then, I had personally guaranteed over $1 million in debt to keep inventory flowing. Now with a proven track record, we were licensed and preparing to relaunch in Ontario. I knew we needed a partner to help raise capital and recruit a world-class team. Enter Dan Park, the then general manager and head of Uber Eats Canada. He joined the business as CEO, and in winter 2020, we relaunched in Toronto. 

After the initial COVID-19 lockdowns, demand surged. Consumers were suddenly more comfortable buying big-ticket items online. Given social distancing, we made a risky move: we eliminated test drives and shifted to a fully online purchasing experience. Conversion improved, and so did customer satisfaction. 

We proceeded to raise a $75 million in Series B and expanded into new markets. But with growth came new challenges. Firstly, we struggled to source enough cars. Competing at wholesale auctions—where other dealers purchase inventory—was a zero-sum game. Secondly, our reconditioning model, split between internal mechanics and third-party shops, struggled under volume. External vendors couldn’t keep pace, and our internal teams needed a better system.

So we started to reimagine both processes. To solve supply, we launched “Sell to Clutch,” allowing people to sell their cars directly–often within hours. It unlocked a new, higher-quality inventory stream and offered sellers a better experience. It also pushed us to build instant-pricing software capable of valuing vehicles on the spot—a first in the Canadian market. On the operations side, we redesigned our reconditioning process using lean manufacturing principles, modelling it after automotive assembly lines rather than the traditional one-technician-per-car approach. Throughput increased, quality improved, and costs dropped.

Those decisions compounded. We grew to become the country’s leading  buyer and seller of vehicles. What began as a better way to buy a car evolved into a two-sided platform where selling to us is just as compelling. To date, we’ve purchased more than $1 billion worth of vehicles directly from consumers. We’ve more than doubled the size of the business every year and are on pace to do it again.

Related: Plug and Play: The Canadian Companies Revolutionizing the EV Industry

Looking back, the toughest challenges weren’t technical but human: convincing regulators that online sales could be safe and transparent, earning early sellers’ trust, and showing investors that capital intensity was a competitive advantage for a model built on quality assurance—not advertising. And, of course, convincing ourselves to take uncomfortable leaps at the right moments.

Canada’s auto market is massive, and modern buyers expect transparency, speed, and certainty—all from their couch. That’s the standard we set for ourselves every day. I started Clutch to fix what felt broken in car buying. Today, with a national footprint, unique supply engine, and customer experience rooted in trust, I’ve never been more excited about what lies ahead.

– As told to Samantha Fink