Introduction
Welcome to another episode of Mastery Fractional CFO’s Punchy Podcast, where we bring you insights from inspiring business leaders who are making an impact in their industries.
In this episode, Ryan Chenier, founder and CEO of Mastery Fractional CFO Services, speaks with Sean Rayland-Boubar, the founder of Red Rebel Armour Inc.
Red Rebel Armour is one of Canada’s leading Indigenous clothing brands, operating as an e-commerce business based in Winnipeg. More than just a streetwear company, it’s a social enterprise on a mission to reduce recidivism by providing on-the-job training and employment to people exiting the criminal justice system. Sean’s journey from personal transformation to entrepreneurship is not just inspiring—it’s a lesson in resilience, purpose, and strategic business growth.
From Personal Struggles to Social Entrepreneurship
Sean Rayland-Boubar’s path to business ownership was anything but conventional. As an ex-gang member and former addict, Sean knows firsthand the challenges of reintegration into society. When he was released from prison in 2018, he made a commitment to change. He completed his education, immersed himself in learning about social entrepreneurship, and soon realized he could use his experiences to help others.
Through Red Rebel Armor, Sean hires and trains people transitioning from incarceration, offering them not just a job but a supportive environment that fosters long-term change. Recognizing that many face systemic barriers such as criminal records, lack of transportation, and limited work experience, his company provides a structure where employees can develop skills, earn an income, and build stability.
The Evolution of a Purpose-Driven Brand
Red Rebel Armor’s clothing is more than just apparel—it’s a movement. The brand’s designs carry messages of healing, cultural preservation, and empowerment. Sean was inspired to create streetwear that represents resilience and growth, contrasting the often-negative imagery found in mainstream fashion.
His focus on quality also sets the brand apart. Red Rebel Armour’s clothing is crafted from high-quality, comfortable materials, with designs that appeal to a broad customer base—from executives and educators to social workers and Indigenous advocates. By ensuring that every product tells a story and aligns with a greater mission, Sean has built a loyal and engaged customer base.
Scaling an E-Commerce Business: Lessons in Growth
Growing a business comes with challenges, and for Red Rebel Armour, inventory management and operational scaling have been major hurdles. Initially, Sean handled sales in a grassroots manner—selling directly to students and teachers while studying at RRC Polytech. As demand increased, he had to shift from a hands-on sales approach to leveraging digital marketing, including Facebook ads and email marketing.
Red Rebel Armour now operates out of a dedicated facility with a team of four full-time staff and five on-call employees. But with growth comes complexity. Managing inventory efficiently while ensuring high-quality production has been an ongoing challenge. The company has turned to software solutions like Katana to optimize order fulfillment and manufacturing processes, reducing errors and improving workflow.
The Financial Turning Point
Before partnering with Mastery Fractional CFO Services, Red Rebel Armor’s financials were in disarray. Sean openly admitted that he had been prioritizing sales without a clear view of his business’s financial health. Inaccurate balance sheets, inconsistent profit and loss tracking, and disconnected accounting systems between Shopify and QuickBooks led to confusion.
Since working with Mastery Fractional CFO Services, Red Rebel's books are now clean, and proper cash flow forecasting is in place. As well, Mastery Fractional CFO Services and Red Rebel Armour are in the process of putting together a structured financial plan.
Having clarity on financial performance has not only improved decision-making but also provided Sean with the peace of mind needed to focus on long-term growth. Looking ahead, Mastery Fractional CFO's focus for Red Rebel will be on formal budgeting and financial planning to prepare for potential investors.
The Future of Red Rebel Armour
Sean’s vision for Red Rebel Armour extends beyond its current success. In the short term, he aims to optimize internal processes, improve training programs for new employees, and enhance product quality. Expanding into international markets, particularly in the Indo-Pacific region, is also on his radar.
Corporate partnerships are another avenue for growth. Larger orders from organizations provide financial stability and allow the business to maintain a steady workflow for its employees. Sean is also exploring ways to expand the brand’s impact by creating apparel specifically designed for entrepreneurs and professionals.
CFO Question: Advice for Growing E-Commerce Businesses
When asked what advice he would give to other e-commerce entrepreneurs, Sean emphasized the importance of financial planning:
“Use a cash flow forecast. Build it into your skill set. It will make decision-making so much easier and help you align new opportunities with your actual financial position.”
Entrepreneurs often carry everything in their heads, but having a structured financial plan can provide clarity and prevent costly mistakes. That's where a fractional CFO comes in.
Final Thoughts
Red Rebel Armour is a prime example of how business can be a vehicle for change. Sean’s journey demonstrates the power of resilience, purpose, and strategic thinking. By aligning sales, operations, and finances, he has positioned his company for sustainable growth while staying true to his mission.
If you’re interested in supporting Red Rebel Armour, you can find their products at redrebelarmour.ca. For business owners looking for financial clarity and strategic guidance, Mastery Fractional CFO Services is here to help.
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What’s Your Next Step? If you found value in today’s conversation, share this blog with another entrepreneur who might benefit from it. And if you’re ready to take control of your business’s financial future, reach out to us at Mastery Fractional CFO Services.
Stay tuned for more insightful conversations with business leaders who are making a difference. Until next time!
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