Sean Rayland-Boubar: From Incarceration to Red Rebel Armour
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iHeartRadio After years in a gang, addiction and 17 months in custody, Sean Rayland-Boubar, an Anishinaabe entrepreneur from Sagkeeng First Nation, built Red Rebel Armour, a Winnipeg streetwear company that hires people leaving the justice system. He's giving others the second chance he had to fight for, while still facing many of the same barriers they do.
Sean tells Stuart why the gangs have always had one advantage over every employment program: they'll put you to work the day you get out. Red Rebel Armour is his attempt to match that low barrier to entry with work that leads somewhere better.
We're talking:
- Why transportation, not a criminal record, is often the biggest barrier to employment
- How flexibility and accountability work together in second-chance hiring
- How jail can feed gang recruitment instead of ending it
- Reconciliation, from treaty obligations to residential school denialism online
- The personal costs of being a cycle breaker
Sean also shares the story behind Red Rebel Armour's Every Child Matters design, which creates seasonal jobs each September and funds donations to local organizations.
He closes by reflecting on the documentary about his work with Elder Lionel Houston, with a message for anyone in prison who believes their life is over: "Whatever you're going through is just a season."