The phone call that boosted the fortunes of mom-and-pop retailers around the world came on a grey Ottawa morning in 2008.
Tobias Lütke was staring at another month of dismal sales from his online snowboard shop when an entrepreneur from Toronto rang with an unusual request: Could he buy the software behind Lütke’s flailing business?
Within weeks, similar calls flooded in. Everyone wanted the platform. Nobody wanted the snowboards.
That's when the 27-year-old German-born programmer realized he'd been running the wrong business entirely — and discovered one of the most valuable lessons in entrepreneurship: sometimes your biggest flop reveals your greatest opportunity.
“Almost every good decision,” Lütke told Business Insider in 2021, “starts as a bad one first.”
Today, Shopify powers 4.6 million businesses across 175 countries and processes more than $235 billion in annual sales — generating $7.1 billion in revenue and employing about 12,000 people worldwide.
The company that made Lütke one of Canada’s richest entrepreneurs (earning $205 million in compensation last year, atop the Globe and Mail's highest paid CEOs list) began as Snowdevil, a spectacular failure that taught him to pivot for the right reasons: let the market lead you where you need to go, and don't get seduced by the founder's trap of sticking stubbornly to Plan A.
In 2004, Lütke wasn’t trying to revolutionize commerce. He just wanted to sell snowboards online from his apartment. Every e-commerce platform he tested was either prohibitively expensive or impossibly clunky. So he built his own using Ruby on Rails — a simple web programming framework that made building websites faster and easier — crafting something both elegant and intuitive.
Snowdevil looked beautiful and worked flawlessly. It just couldn't survive the 2008 financial crisis when customers stopped buying luxury sporting goods and started buying necessities instead.
Most entrepreneurs would have cut their losses. Lütke started selling his failure.
Lütke later reflected that he wasn’t really in the snowboard business, but rather in the business of helping people sell things online.
“What we're trying to do is take this really, really complex idea of internet entrepreneurship and make it as simple and straightforward as possible,” Lütke told the 2019 Open Core Summit. “We think there’s a huge global demand for people reaching for their own independence.”
Lütke's story resonates deeply in Canada, where resource constraints breed innovation. Without Silicon Valley’s venture capital or Bay Street’s connections, he built something genuinely superior, not just better-funded.
Small businesses across Canada were going digital but couldn't afford enterprise-level solutions.
Shopify democratized e-commerce by making sophisticated tools accessible to ordinary people, transforming entrepreneurship for merchants in every sector, every town, every city.
The platform that began in an Ottawa apartment would soon power Drake’s official store and thousands of small businesses that jumped online during the pandemic.
Lütke built more than a world-class company — he created the infrastructure for generations of entrepreneurs.
Seventeen years later, Lütke's journey teaches three essential lessons of entrepreneurship.
First, chase problems, not solutions.
Lütke thought he was solving “how to sell snowboards online.” He was solving “how to make e-commerce accessible to anyone.”
Many entrepreneurs pivot for the wrong reasons — chasing “shiny new things” like blockchain or wearable tech without their customers demanding it.
Lütke listened to his customers and delivered.
Second, embrace accidental customers.
Those early entrepreneurs calling about licensing weren't in his business plan. They were market signals about what he’d actually built.
The best opportunities come from paying attention to who uses your product in ways you never imagined.
Third, amplify your unfair advantage.
Lütke's programming skills and design instincts didn’t become irrelevant when he stopped selling snowboards.
They became the foundation for Shopify's ascent.
Lütke's pivot didn't just save his business — it enabled millions of others to flourish.
Shopify created an ecosystem where countless entrepreneurs could thrive. The failed snowboard seller became the rocket fuel of global commerce, a force that empowered other companies to launch, then pivot too.
As AI reshapes industries and economic uncertainty forces adaptation, companies that master intelligent pivoting will grow stronger.
Maybe your customers want an AI product that integrates your data to help them make better business decisions.
Ask them. Co-create it with them.
Canada faces post-pandemic realities, tariff shakes, and the AI revolution.
Lütke's journey from Snowdevil to a $140-billion powerhouse offers both hope and instruction.
Entrepreneurship isn't about executing flawless strategies, it's about staying curious enough to recognize when the market teaches you something new about what you’re really building.
The snowboards vanished long ago. The empire they inspired now spans the globe, seeding millions of dreams and proving that sometimes the best business plan is the one you never wrote.
What is your market trying to tell you?
Your next pivot might not be a retreat — it might be the breakthrough that changes everything.
