What happens when you blend Indigenous values, entrepreneurial grit, and a mission to do business differently? You get Cheekbone Beauty, one of Canada’s most purpose-driven beauty brands—and the brainchild of Jenn Harper.
In this live episode of Mission Critical recorded in Toronto at Waterworks Food Hall, Lance sits down with Jenn to unpack her incredible journey—from overcoming addiction and selling fish (quite literally) to discovering her purpose in a dream and pioneering what she calls Indigenous Beauty, a category rooted in authentic sustainability.
Jenn gets candid about the highs and lows of building a brand from scratch, how close she came to shutting down, and why community—especially her customers—has always been the foundation of her success.
This episode is presented by Mastercard Canada as part of a special series spotlighting small business owners who are shaping the future of Canadian entrepreneurship.
Listen now to hear how Jenn is rewriting the narrative—and what she wants the world to know about Indigenous excellence, sustainability, and the future of beauty.
Key Highlights & Takeaways
- 💄 Origin Story with Purpose: Cheekbone Beauty was born from a dream—and Jenn’s mission to give back to her Indigenous community and rewrite the narrative around Indigenous success.
- 📚 Scholarship Fund Impact: With the support of partners like Mastercard, Cheekbone Beauty launched a scholarship fund that has awarded 30+ scholarships to Indigenous youth since 2021.
- 🌱 Indigenous Beauty as a Category: Jenn is working to define Indigenous Beauty as a global category—anchored in authentic sustainability, community values, and cultural leadership.
- 🔥 Billion-Dollar Vision: She’s unapologetically building a brand with the goal of reaching a $1B valuation—and doing it with only six full-time staff and a lot of heart.
- 🤝 The Power of Community: Jenn credits her survival in business to loyal customers and movements like Buy Canadian, proving that small business success is community-driven.
- 💬 Leadership Through Love and Humility: Drawing from her Anishinaabe culture, Jenn built Cheekbone’s core values on love, humility, and integrity—redefining what business leadership can look like.
- 🎤 Being Vulnerable Online: Jenn opens up about sharing her story publicly, navigating social media as a founder, and why transparency helps build stronger customer relationships.
