The Canadian Business Evolution Summit returned this month, uniting Canada’s top business minds to explore critical themes in innovation, resilience, and entrepreneurship. Hosted at King West’s Luma venue atop the TIFF Lightbox, this multi-day event offered a platform for forward-thinking discussions on Canadian micro-business, Indigenous entrepreneurship, and the evolving importance of brand trust.

Night One – Building Resilience for Micro-Entrepreneurs

Sponsored by Wave and Amazon Web Services (AWS), the first evening of the summit focused on strategies for resilience for Canada’s micro-entrepreneurs. CB Publisher Jason Maghanoy set the stage, describing the summit as a week dedicated to exploring “all those incredible moments” in business—whether they are moments of breakthrough or hardship.

The evening’s live taping of CB – The Moment podcast featured Maghanoy and co-host Fatima Zaidi with their guest, Marie Chevrier, former CEO of Sampler. Chevrier’s journey, including the rise and eventual closure of her company, brought home the realities of the entrepreneurial rollercoaster. Reflecting on her experience, Chevrier emphasized the value of resilience over perfection: “If we can master the art of rebounding, each next business becomes stronger and smarter.” 

The marquee panel followed, with insights from Wave’s Zahir Khoja, AWS’ Dan Stark, Mayana Genevière’s Nadine Woods, and Anishinaabe entrepreneur Chelsee Pettit. Each speaker offered practical insights into the trials and successes unique to small businesses. Woods underscored the strength in community, sharing how she leveraged local connections to navigate post-pandemic challenges: “Community isn’t just a buzzword. For us, it’s survival and strength. By hosting events and fostering a space of support, we build a brand with purpose and connection.”

Pettit highlighted the pressing reality of cash flow for small businesses, noting that despite the reality that waiting for payments can leave one feeling overwhelmed, it forces businesses to learn how to adapt. Khoja shared that cash flow is foundational: “Cash flow isn’t optional—it’s survival. When money flows in more than it flows out, you can actually focus on building the business.”

Stark also touched on technology’s role in small business success, affirming: “Technology isn’t optional anymore. The pandemic has proven that without it, businesses can’t compete.” Stark noted that small business owners with limited resources are increasingly using AI and digital tools to streamline operations, to remain agile and resilient.

The evening closed with a networking hour—an invaluable chance for attendees in all chapters of their business journeys to connect over food and drinks, courtesy of Luma.

Night Two – Indigenous Entrepreneurship and Brand Trust

The second night of the summit – sponsored by BMO, Mastercard Canada, and Beneva Insurance – tackled Indigenous entrepreneurship, technology’s role in business, and the evolving landscape of brand trust. 

The evening began with a VIP fireside chat featuring Bobbie Racette, CEO of Virtual Gurus, and Sasha Krstic, President of Mastercard Canada. Racette’s inspiring journey as a queer Indigenous woman in tech resonated with the audience as she recounted overcoming barriers: “One hundred seventy investors said no. But if you’re driven by purpose, you keep pushing forward, no matter how many doors close.” Despite these obstacles, she grew her business from a $300 startup to a global platform.

Krstic noted Mastercard’s dedication to Indigenous prosperity: “We can’t grow Canada’s economy without including the Indigenous economy. Empowering Indigenous businesses isn’t just a goal—it’s essential to our national success.”

Related: How This Brand Owner is Nurturing Indigenous Wisdom, Wellness and Entrepreneurship

The final  panel of the night, arranged in sponsorship by Beneva Insurance, transitioned the discussion to brand trust and AI, featuring insights from Sara Cappe, President of The Harris Poll Canada; Greg Brown, VP at BMO; and John Weigelt, National Technology Officer at Microsoft Canada. 

Cappe observed that Canadians tend to scrutinize homegrown companies more critically, noting, “Trust is earned every day, and for Canadian companies, the bar is set higher. Canadians expect authenticity and integrity from brands that call Canada home.” Brown added that, in digital banking, “Trust is built on privacy, security, and simplicity.” Weigelt explained that for Microsoft, trust hinges on using AI responsibly, especially given Canada’s cautious approach: “AI is transformative, but it demands responsible implementation. Canadians expect accountability and transparency.”

As businesses face a technology-driven future, the panelists highlighted the importance of using innovation to not only stay relevant but to strengthen relationships with their communities. In a climate where consumer expectations are increasingly tied to values like security and transparency, the night’s speakers emphasized that trust and technology must go hand-in-hand to build resilient, impactful brands.

As night two closed with a lively networking session, attendees exchanged ideas and inspiration over drinks and bites, embodying the values of community central to Canada’s evolving business landscape.