Cheekbone Beauty’s Jenn Harper Joins Mission Critical and Mastercard for a Night of Purpose-Driven Conversation
Earlier this summer, GLORY brought together Toronto’s sharpest creative minds and business builders for a special live edition of its flagship podcast, Mission Critical with Lance Chung. Held in the heart of the city at Waterworks Food Hall, the event—presented in partnership with Mastercard—was an ode to the passion, purpose, and resilience of Canadian small business owners.
Against the industrial-chic backdrop of Waterworks, guests filtered into the intimate space from across the entrepreneurial spectrum: ceramicists, jewelers, restaurant owners, content creators, fashion founders, and beauty entrepreneurs. What they had in common was grit, creativity, and a shared understanding that building something from scratch is no small feat.
Before the main event, the crowd networked over drinks and bites, swapping information, Instagram handles, and founder stories. A Cheekbone Beauty station showcased the brand’s cult-favourite products—an immersive prelude to the conversation ahead.
Then, it was time to talk business. Nadine Arous, Director of Small and Medium Enterprises at Mastercard in Canada, opened the evening with a rallying call to entrepreneurs, speaking to the vital role small businesses play in strengthening our communities. She highlighted Mastercard’s commitment to empowering small businesses by building solutions that meet their needs—whether through funding, mentorship, products, partnerships, or other essential resources. By championing small businesses, Mastercard is fostering growth that not only uplifts local entrepreneurs but also drives prosperity for communities. Because when a small business succeeds, it benefits everyone.
Enter Jenn Harper, founder of Cheekbone Beauty and the evening’s guest of honour. In conversation with host Lance Chung, Harper offered a candid, vulnerable look into her entrepreneurial journey: from selling fish and battling addiction to launching one of Canada’s most impactful beauty brands. “Cheekbone started with a dream—and not the metaphorical kind,” she shared. “I literally dreamt about three Indigenous girls wearing lip gloss. That was the spark.”
She spoke about launching Cheekbone’s now-celebrated Scholarship Fund, which has awarded 30 scholarships to Indigenous youth since 2021—an initiative made possible by sponsors like Mastercard. She also touched on the role of her brand’s community: “We were this close to not existing last year. Nothing exists without the support of your community—who are your customers.”
Perhaps the most powerful moment came when Harper laid out her long-term vision: to define “Indigenous beauty” as a global category rooted in authentic sustainability, and to scale Cheekbone into a billion-dollar brand. “Why not us?” she said. “Why not now?”
The evening wrapped with more conversation, new connections, and the unmistakable feeling that something important had just happened. Because when you put Canada’s brightest entrepreneurs in a room, give them the space to connect, and the tools to grow—something powerful happens.
This event was an example of Mastercard’s impactful support for the small business community in Canada. If you’re interested in learning more about future events featuring entrepreneurs like Jenn Harper, tapping into a small business network, or accessing resources that support Canada’s vibrant entrepreneurs, join the Mastercard Small Business Community.
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