Rebel with a Cause

Photo: Sean Rayland-Boubar (R), a judge at the 2024 Manito Ahbee pitch competition, presents Simon Monteith (a.k.a. Simon the Scientist) with the Youth Prize and Fan Favourite prize. Submitted by Pow Wow Pitch, photo by Janique Tessier. 

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Altis is a proud partner of Pow Wow Pitch, a non-profit that supports and empowers Indigenous entrepreneurs through funds, mentorship and resources. This National Indigenous History Month, we’re featuring Pow Wow Pitch success stories, including 2022 Second Place Prize Winner, Sean Rayland-Boubar, founder of Red Rebel Armour.

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Highlights:

• Founded in Winnipeg in 2019, Red Rebel Armour is an Indigenous-owned streetwear company with a social purpose.
• Founder and owner Sean Rayland-Boubar from Sagkeeng First Nation is an ex-gang member and addict turned social entrepreneur.
• His company doesn’t just sell clothes — it creates second chances. Through Red Rebel Armour’s apparel line and Wahbanung Employment Service, they’ve hired and trained 21 Indigenous employees in a culturally safe environment, 13 of whom were formerly incarcerated (and of these, seven have been successfully reintegrated).
• The company also honours and preserves Indigenous cultures by incorporating traditional designs, techniques and symbols into their clothing, all created by Indigenous artists.
• In 2022, Sean won the Second Place Prize of $10,000 at Pow Wow Pitch.
• Since then, he has grown Red Rebel Armour to almost $1 million in annual sales and donated over $20,000 to Indigenous community initiatives.
• To scale his company further, he has launched a crowdfunding campaign with the goal of raising $300,000. Learn more.

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In May 2018, Sean Rayland-Boubar said goodbye to his old life.

While incarcerated in Winnipeg for gang- and drug-related activities, he decided it was time to put his street survival skills to good use by helping others.

It wasn’t an easy choice because once you’re in that world, he says, it’s hard to get out. “It’s like turning your back on your community. You get out [of prison], and everybody expects you to always do the same thing,” he says.

A member of the Eagle Clan from the Sagkeeng First Nation, Sean thinks these expectations are part of the reason why Indigenous people are overrepresented in the criminal justice system in Manitoba, where they account for over 75% of all admissions to prison despite making up only 18% of the province’s population (as of 2021).

It’s a cycle that “feeds itself” for many in his community, he says. They leave prison with a criminal record, no income, no housing and no connection to their family, so they turn back to the welcoming street community and a guaranteed source of income. And on it goes.

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Breaking the cycle by giving back

Upon his release from prison, Sean decided to launch a business instead. One that would help others like him get on a different path.

“In the beginning it was scary, but I'm glad I stood up and just kept going through it because now it's kind of like a beacon of light for others,” he says.

For two years, he studied Social Innovation and Community Development at RRC Polytech and graduated with a diploma in Indigenous Social Entrepreneurship. Then, he set out to combine streetwear fashion and social enterprise to elevate his community through his own story of healing, identity and resilience.

He launched streetwear brand Red Rebel Armour from his basement with a mission to break the cycle of recidivism by providing Indigenous people reintegrating into society after incarceration with flexible, paid, on-the-job training in a culturally safe work environment.

So far, he’s hired and trained 21 Indigenous employees, 13 of whom were formerly incarcerated (and of these, seven have been successfully reintegrated).

He teaches them the basic skills required to create his clothing line — a series of culturally representative hoodies, sweatshirts, T-shirts and more designed by Indigenous artists Amy Jackson from Opaskwayak First Nation and Kale Bonham from Swan Lake First Nation.

And more importantly, he shows his employees a different path in life, one that involves paid employment or schooling and a chance to reconnect with their culture and community. Past employees have returned to school and found work in construction or other industries.

In this way, Sean has not only changed lives but also estimates that he has saved the federal criminal justice system more than $500,000.

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Circle of Courage: Helping others go from surviving to thriving

While incarcerated, Sean connected to his culture through knowledge keeper and Elder Lionel Houston. Upon his release, he continued to work with Elder Houston, became a Sun Dancer, began attending ceremonies and sharing circles, and discovered Dr. Martin Brokenleg’s Circle of Courage theory, which emphasizes belonging, mastery, independence and generosity as essential values for developing Indigenous youth.

Today, Sean weaves this theory through everything he does at Red Rebel Armour.

“It’s first about creating a sense of belonging for somebody, so they can move into the mastery stage,” he says.

By offering a welcoming, culturally safe work environment, Red Rebel Armour gives its employees the chance to share their experiences with each other while learning new skills and navigating a new way of living.

He offers a flexible schedule, too, so his team can balance all the aspects of reintegrating into society — parole officer appointments, mental health treatments and schooling — with their work schedule. He subsidizes transportation to and from work, one of the main barriers many Indigenous people face upon leaving the criminal justice system. And he helps connect team members with organizations that provide stable housing.

“When they’re in the mastery stage, they’re able to learn more about themselves, along with new skills like how to operate a heat press, pack and ship inventory, operate an embroidery machine and Direct to Film printer,” Sean says. And eventually, they move into independence.

“Without employment, you’re only thinking about today. You have low self-esteem because you can’t take care of yourself without an income, so you have to ask for everything, even bus fare,” Sean says. “When somebody is able to maintain employment for at least three months, they move out of survival mode into thriving,” he says.

In other words, they move into independence. Learning to show up, do the work and get paid for it.

Finally, they learn about giving back — the generosity stage. Sean regularly raises money for Indigenous initiatives such as last year’s Eagle/Wolf Sundance, to which he donated $6,000. He explains to his team that just by showing up and doing their jobs, they’re giving back to others and adding value, something they never thought possible.

In total, Sean has donated more than $20,000 to Indigenous initiatives.

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Scaling and growing

Since founding Red Rebel Armour, Sean has steadfastly (and single-handedly) grown the company, reaching almost $1 million in sales today. And he has ambitious goals for the future.

In 2022, after winning the second-place prize of $10,000 at Pow Wow Pitch, he moved out of his cramped quarters and into a bigger warehouse, so he could employ more people, buy more equipment and scale his offering.

In addition to selling his regular line of clothing, which ebbs and flows with the demands of the season (for example, slower in the summer and post-Christmas), he purchased a Direct to Film printer that enables him to keep his shop running year-round by offering a custom printing service (for example, for companies looking to create corporate swag).

To reach new audiences, he’s also adamant that his clothing is for everyone — Indigenous and non-Indigenous people alike.

When people ask about cultural appropriation, his answer is always the same: “It's actually quite the opposite. If you come with the right intention, it's about cultural appreciation.” He encourages his customers to learn about his products and even provides a link to an Indigenous Ally Toolkit on his website.

A self-taught digital marketing pro, Sean manages all digital advertising, generating roughly half of the company’s revenue (the remainder is from the Shopify store), and juggles all the training and onboarding of his team as well.

It’s a lot, especially for a father of four young children ranging in age from 14 months to 12 years old.

As word continues to spread about his company, more people are showing up on his doorstep looking for work or contacting him by phone, email or social media inquiring about opportunities. “Even my staff have friends who want to come and work here because they know it’s a safe work environment,” he says.

“It’s amazing to see such commercial impact and social impact, but I’m at capacity myself,” he says.

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What’s next for Red Rebel Armour?

To keep growing, he realizes he needs additional capital to hire senior staff who can help with operations, maybe a fractional operations manager.

So, he launched a crowdfunding campaign with the goal of raising $300,000. Learn more and donate here.

Another possibility for growth is by launching Red Rebel Armour in other communities that are in need, something Sean says the government seems interested in. “There are at-risk youth in other places, so maybe we just franchise the model throughout the country,” he says.

And his North star goal?

“If we could hit $10 million, that would be great,” he says.

To learn more about Red Rebel Armour, visit https://redrebelarmour.ca.

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Watch the next round of Pow Wow Pitch entrepreneurs

Want to watch more inspiring Indigenous entrepreneurs pitch their business ideas for a chance at winning a prize? Mark your calendars for these upcoming pitch dates:

• September 2-12, 2025: Pow Wow Pitch Semi-Final Episodes will be dropped daily at 6:00 PM ET at www.powwowpitch.org/episodes.
• October 22, 2025: Join Pow Wow Pitch online for the Grand Finale live at 6:00 PM ET.
• Follow Pow Wow Pitch on social media for the latest news and stories.

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