Written by: Techub News Organized

Introduction

At the main stage of Toronto Tech Week 2025, a heavyweight dialogue focusing on "ambition" is taking place. Shopify President Harley Finkelstein is hosting the discussion with Canadian fintech star Wealthsimple's founder and CEO Mike Katchen, along with global AI unicorn Cohere's co-founder and CEO Aidan Gomez, exploring the future of technology entrepreneurship in Canada.

These three men are leaders in the e-commerce, fintech, and AI sectors. The companies they lead are not only well-known domestically but also have significant influence globally. Their dialogue is important because it directly addresses the long-standing core issues that have plagued the Canadian tech ecosystem — "ambition" and "brain drain" — and attempts to provide a strong answer: stop complaining and start building, right here in Canada.

Summary

• Clarifying Misunderstandings about Ambition: Harley Finkelstein clarified his remarks about Canada needing more "ambition," emphasizing that it is not a lack of ambition among Canadians, but rather that all entrepreneurs need greater aspirations and sustained innovative energy.
• The Power of "Naive Ambition": Mike Katchen proposed the concept of "naive ambition," which means setting aside countless reasons of "impossible," and thinking instead about "what needs to be believed to succeed," which was key in challenging traditional financial barriers to establish Wealthsimple.
• Staying in Canada, Serving the World: Aidan Gomez emphasized the reasons for establishing Cohere in Canada (Toronto) based on loyalty and strategic choice, pointing out that Canadian brands are a tremendous asset in global geopolitics, and calling for the establishment of Canadian institutions that benefit the world, not just local markets.
• Proactively Rejecting External "Pull": The three founders shared how they rejected pressures to relocate to the U.S., declining acquisition offers and the pressure to transform their company structures into U.S. entities, emphasizing the importance of maintaining a Canadian headquarters and building local giants for the ecosystem and the country's future.

Refuting Misunderstandings: What We Need is Greater Ambition, Not Doubting Its Existence

At the beginning of the dialogue, Harley Finkelstein first clarified a public misunderstanding that had troubled him for eight months. Eight months ago, he stated that Canadian tech entrepreneurship needed a "600-pound gorilla in the room," implying a need for greater "ambition." However, the next day, almost all media interpreted it as "Harley thinks Canadians lack ambition." Finkelstein emphasized that his original intent was exactly the opposite: Canadian entrepreneurs are ambitious, but we need more and greater ambition, along with the energy to sustain that ambition.

He cited data from S&P 500 constituent companies to support this viewpoint: "The average age of S&P 500 companies has dropped from a historical 36 years to just 21 years today. When you look at those that were removed, it turns out they didn't die from competition, but from stagnation — they lost the energy and spark that initially filled them with ambition." Finkelstein hopes that today's dialogue will inject more of that energy into everyone.

He went on to point out that sitting next to him, Mike Katchen and Aidan Gomez are practitioners of this "grand ambition," each challenging the heavily regulated financial services industry and at the forefront of the artificial intelligence sector, establishing world-class companies in Canada.

"Naive Ambition": The Art of Challenging the Impossible

When asked how he built Wealthsimple in the heavily guarded financial services sector, Mike Katchen shared one of the company's core values: "naive ambition."

"When you propose a new idea, like 'let's start a financial services company,' most people's first reaction is to list thousands of reasons why it will never succeed," Katchen recalled, noting that he was 25 at the time with no prior experience in the finance industry. "People said Canadian banks have absolute monopolies on trust, it will never work."

Wealthsimple's approach was to "flip the question": "We asked ourselves: 'What do we need to believe for this to succeed?' That's what 'naive ambition' is all about." He stresses that Canada needs more of this "naive ambition," firmly believing that the world's best companies can be built from here.

Katchen believes this ambition should not be limited to founders. At Wealthsimple, they uphold "naive ambition" as a corporate value, expecting every employee to drive the company's aspirations. "My favorite moments are when we achieve great success, and I'm the last person to know about it," he explained, citing an event two weeks prior at the same venue where Wealthsimple hosted a large event titled "The End of Banking," attracting 100,000 viewers across Canada, while he was completely unaware of the event's planning as the speaker. "That tells me we've created a culture where people believe great things are possible."

Why Root in Toronto: Loyalty, Talent, and National Brand

Aidan Gomez shared his thoughts on why he chose to establish Cohere in Toronto instead of Silicon Valley or elsewhere. He believes the problem in Canada is not a lack of ambition, but rather "brain drain" — a significant amount of top talent heading to the Bay Area or elsewhere, undermining the local ecosystem.

Gomez and his co-founders were all born in Canada; for them, this is home. "The taxpayers of this country paid for my education, my healthcare, so there is no other choice. I have a deep nationalism and loyalty to this country, to build here, and as Harley said, to contribute a company with global ambition for our country." He emphasized that the goal should not just be to build a company serving Canada, but rather to establish a company in Canada that serves the world.

Additionally, Gomez pointed out the strategic advantages of starting up in Canada: Canada's national brand is a significant asset. "As geopolitical changes unfold on the global stage, the Canadian brand has never been stronger... Canada is seen as a truly good country, with a strong moral and ethical framework. People want Canada to succeed, and they are on our side." This brand reputation brings global trust and collaboration opportunities for companies like Cohere.

Gomez mentioned that Cohere has even experienced "reverse brain drain" — talents from places like the U.S. wanting to come to Toronto to join them. This is thanks to Toronto’s continually evolving ecosystem and community cohesiveness, achieved through organizing events like Toronto Tech Week, bringing communities together to inspire and connect.

Telling the Story Well: A Cultural Shift from "Apology" to "Pride"

Harley Finkelstein posed a critical question: Are Canadians poor at telling the success stories of their companies and their country? He observed that many entrepreneurs are dedicated to their toil but are either shy or neglectful of sharing their achievements.

"I think we often felt sorry for our success in the past," Finkelstein said, but the situation is changing now. "I think a major shift that has occurred is that now we have a sense of pride — just like I can build this company anywhere I want." He shared his decision to stay in Canada (moving from Ottawa to Montreal) rather than return to the U.S., where the general expectation was he would leave Canada.

Aidan Gomez attributed the ability to tell stories to community and "the spirit of the times." He noted that Toronto is forming an emerging "spirit of the times," with vibrant communities (he mentioned Vin and 535) creating spaces for ideas to collide and stories to emerge. "We are phenomenal storytellers and brand builders, capable of creating what the world wants to see. We just need to invest time and do more."

Mike Katchen believed that the key to storytelling lies in engaging in meaningful pursuits. "If you're engaged in something meaningful and purposeful, it becomes very easy to tell stories around it." He reflected on his deeper motivation for returning to Canada, which was concern over the trajectory of the country’s economy: "We only do two things: we dig things out of the ground, and we finance digging those things. If, twenty years from now, the story I tell my children is still this, then the wonderful things we enjoy — education and healthcare that someone pays for — will all disappear." In his view, reshaping the economy through entrepreneurship is the only way out, and that goal itself constitutes the most powerful story.

Resisting the "Pull": Saying "No" to Acquisitions, Saying "No" to Relocation

As a focal point of the global AI surge, Cohere is undoubtedly a "hot cake" in the eyes of numerous giants' acquisition departments. Harley Finkelstein was curious about how Aidan Gomez resisted those tempting acquisition offers.

Gomez's response was straightforward: "We simply do not open ourselves up (to be acquired). We are not for sale." He bluntly stated: "To me, being acquired is a failure, it ends the process of building." He shared an early experience: at a time when the language model market did not yet exist, Cohere received a "nine-figure" acquisition offer from an American tech giant. The board seriously considered it but ultimately rejected it. "I am now extremely, extremely grateful we didn’t accept. We are still rapidly growing; I just focus on the reality of building, with no time to consider another (acquisition) reality."

Finkelstein added that Shopify's early practice was to simply not respond to any acquisition department's calls, to avoid initiating a conversation loop that might lead to distraction.

Beyond acquisitions, the greater "pull" comes from pressures to relocate the company or convert its legal entity to a U.S. corporation (like a Delaware company). Gomez revealed that he recently received a plea from a founder who was accepted into a top U.S. incubator, which required him to turn the company into a Delaware entity. Gomez's advice was to firmly decline: "We need to start saying 'no' to these kinds of pressures... We need to take a proactive nationalist stance and build for Canada."

Finkelstein and Katchen also shared similar experiences. Finkelstein recalled that during Shopify's Series A funding, investors made relocation to Silicon Valley a condition for investment, but they declined and ultimately found investors who didn’t care about where they were located, only about their vision and team. Katchen recounted the early struggle of Wealthsimple when no one was willing to invest; they sought support from Canadian institutions (like Power Corp), which provided them with stable capital focused on business development, ultimately attracting top global investors to invest in Canada for the first time.

They all emphasized that today the environment for financing and building global companies in Canada is "much easier" than it was ten years ago, thanks to the path paved by pioneers like Shopify, Wealthsimple, and Cohere.

Looking to the Future: Companies Worth a Trillion and the Survival of the Nation

As the dialogue came to a close, Harley Finkelstein proposed an inspiring goal: Canada has never birthed a trillion-dollar company in its history. He firmly believes that someone in the room—be it on stage or in the audience—will achieve this landmark in the next ten or twenty years. "Whoever you are, you not only have our complete support, but you also have the support of the entire nation. We stand behind you." He promised to provide whatever help is necessary.

Aidan Gomez took the topic to the level of national survival. "I think Canada is facing threats... The question of 'should Canada exist' has been put on the table. If we do not strengthen our economy, do not establish diversified supply chains and clusters of companies... we will cease to exist half a century from now. This is a matter of survival." Therefore, he called on Canadians to "build for the nation," which requires deep commitment and ambition. Fortunately, the global trust and support for Canada provide enormous opportunities for this. "Everyone in the world loves Canada; they want to buy your products. Give them a reason. Go build, go global. This is the only way we defend our home."

Mike Katchen referenced the book "Why Don’t Mexicans Drink Molson Beer?" as a closing point. This book explores the predicament of Canada having all the elements to build world champion companies yet failing to find the "formula." His wish is: "I hope my children will never read that book because it will become irrelevant due to the leading world-class companies built by those present here. Canada will hold its rightful place in the global economy."

Finally, Finkelstein delivered a clear message to all ambitious entrepreneurs in Canada building great companies: you have a supportive community behind you, with Mike, Aidan, and me, along with the entire community, ready to help you realize your dreams. The only request is: Go do it and tell the world loudly.

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