When Harley Finkelstein opened his talk at Elevate Festival in 2024, he didn’t expect a Globe & Mail call-out. 

Last year, the Shopify President, in discussion with astronaut Chris Hadfield, said “the 600 pound elephant in the room is that Canadians need more ambition.” 

The next morning, he woke up to a front-page headline reading ’President of Shopify says Canadians have no ambition.’ The illustration of a 600-pound beaver was the icing on the cake.

“That’s not what I said,” laughed Finkelstein, on stage again at Elevate Festival 2025, interviewed by Super.com’s co-founder and CEO Hussein Fazal. 

“I said Canadians need more ambition.”

His point was, and remains, simple: Canada has great founders and builders but not enough belief in its own capacity to lead. It was a call for urgency, not ego. 

In a separate session, Maverix Private Equity founder and managing partner John Ruffolo echoed that concern from a different angle: “If someone were to invade our land and control our land, you would engage in a war and try to throw them out,” he said. 

“It’s the same thing from an economic perspective. Instead of supply chains of physical warehouses, it’s supply chains of servers and data.”

Both conversations came back to the same question: what kind of country does Canada want to be? Finkelstein argued that ambition fuels innovation. Ruffolo warned that without digital control, even the most ambitious companies risk building prosperity that others will own.

As Interac’s Debbie Gamble said, before interviewing Ruffolo on the festival’s main stage, “Canada has found its way to lead, not just through its size, but through trust. Trust has always been part of our DNA.”

Canadian contributions to the world like insulin and peacekeeping, and even the evolution of AI, are not just rooted in policy or tech. 

“They’re about trust, trust in our institutions, in science and in each other,” she added. 

“When we talk about sovereignty, it’s not just about borders and treaties. At its core, Canadian sovereignty means our ability to define our own future without foreign influence, to drive our agendas and our ambitions.”

Reclaiming control in a digital economy

Ruffolo has been sounding the alarm on digital sovereignty for years, but he says it only started gaining traction when the risks became impossible to ignore. 

“It really wasn’t until the White House started playing with our sovereignty that it started to come to light,” he said.

For him, sovereignty isn’t abstract. It’s about who controls the servers, data, and supply chains that now define national economies. 

“The seven most powerful, valuable companies in the world today are all technology companies based in the United States, and that just gives you a sense of the threat of digital sovereignty over this country,” he said.

Canada, he argues, still treats digital infrastructure like an afterthought, while the U.S. and the European Union have already built frameworks to protect their assets. 

“Our current frameworks and legal needs are structured still on a post-World War Two industrial economy,” he said. 

That lag has consequences. Canada risks becoming, in Ruffolo’s words, “a branch-plant economy” that produces ideas and talent only to see them commercialized elsewhere. 

“You don’t really understand what’s at stake until it’s taken away,” he added.

The ambition problem

Finkelstein’s argument is less about policy and more about mindset. Canada, he says, has the people and ideas to lead globally but often limits its own potential. In doubling down, he’s clarifying that the country doesn’t lack talent but underestimates what it can achieve.

“We need more Husseins. We need more Super.coms,” he said, referring to Fazal’s Toronto-based company. “We need more of a lot of the companies you are building here.”

For Finkelstein, the challenge isn’t just scaling startups but creating systems that let them compete on a global scale. Shopify’s model, he explained, shows how Canadian companies can lead without being confined by geography. 

“You can build a company from anywhere you want, and you can hire people anywhere in the world, and you can have customers anywhere in the world,” he said.

That flexibility is an advantage, but only if Canadian founders believe they can play on that level. Finkelstein called for a cultural shift, arguing that ambition has to be taught and celebrated, not treated as arrogance. 

“We’ve got to start celebrating the wins and the losses,” he said. 

Finkelstein noted that if you walk into a bookstore asking about BlackBerry or Nortel, the books you’ll be handed are all going to be about the demise of the companies.

“There’s no books about the fact that Blackberry, these great entrepreneurs from Waterloo, Canada, basically created the smartphone industry, or that Nortel created a whole cohort of millionaires that have now become angel investors.”

Competing on Canadian terms

For Ruffolo, reclaiming control starts with confidence in Canadian capability. 

“We have the talent. We have the brain power,” he said. “We need to keep the capital here.”

That includes supporting homegrown companies through procurement and investment, something he says Canadians still hesitate to do. 

“[The US] is proud to say ‘Buy American.’ We’re scared to say ‘Buy Canada.’”

Finkelstein’s version of the same argument is cultural rather than policy-driven. He wants ambition to become part of the national identity — a reflex, not a rarity. 

He pointed to education as a starting point, pointing to the classic question kids in elementary school are asked: what do you want to be when you grow up? 

“I kid you not, logician is often on this list, true, but entrepreneur is never on the list, ever.”

Ultimately, both leaders are talking about sovereignty, just in different languages. 

Ruffolo’s version is about control of systems. Finkelstein’s is about mindset. One defends infrastructure; the other defends belief.

Building a future worth owning

Canada’s economic future depends on both. Without sovereignty, ambition risks being co-opted by foreign systems. Without ambition, sovereignty risks turning into protectionism without progress.

Ruffolo ended his conversation on a note of optimism. 

“The key word here is hope,” he said. “I have been very publicly grumpy because I was getting frustrated that you could see us going down a very, very dark path.”

He added, “I’ve never seen such a shift of thinking as I’ve seen in these last few months.”

That shift might be the most Canadian thing about the moment: a mix of realism and resolve. 

Final shots

• Sovereignty and ambition aren’t competing ideas. Canada needs both to stay competitive.
• Building Canadian companies means keeping data, capital, and confidence at home.
• The real test of leadership is whether the next generation still believes Canada is the best place to build.