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After Incarceration, Entrepreneurship Offers a Path to Empowerment

Formerly incarcerated individuals face stigma and employment barriers, but Emily O'Brien believes they have the creativity and resourcefulness to succeed as entrepreneurs
Woman climbing over a prison wall.
{Photography: iStock}
By Emily O'Brien
Jul 21, 2025

A trip to St. Lucia in 2015 took a sharp turn for the worse when I got coerced into strapping two kilos of cocaine to myself to smuggle into Canada. I realized too late that a close friend I trusted had given my passport information to drug dealers, telling them I would help him transport drugs across the border. I had never thought of doing anything like that in my life, and I was scared of what would happen if I refused.  

Arrested on my way out of Toronto’s Pearson Airport, I started my prison sentence in January 2018. Within a year, I was released on parole and transferred to a halfway house. That’s when I first encountered the stigma and barriers that those who have served time face when trying to re-enter the workforce. 

When someone is released from prison, they receive almost no financial or emotional support to successfully reintegrate into society. A study by the John Howard Society on employer attitudes towards formerly incarcerated people found that 51 per cent of respondents would not hire someone with a criminal record. Additionally, 55 percent believed these applicants posed a “heightened risk and liability” in terms of physical safety or economic impact, and assumed they had lower skill levels compared to applicants without a criminal record. Yet, paradoxically, 92 per cent of those same respondents also expressed support for reintegrating people with histories of incarceration into the workforce. 

Although many formerly incarcerated people possess transferable skills that could improve their lives, these skills often fail to translate into better futures. A 2019 study by Correctional Services Canada (CSC) found that 23 percent of federal offenders from a 2011 cohort re-offended. Supporting these individuals in developing their business ideas and securing sustainable work through entrepreneurship can play a crucial role in reducing recidivism.

Despite persistent stereotypes, formerly incarcerated people have the creativity and resourcefulness needed to run a business. During my time in prison, I saw inmates make lipstick out of beet juice or thread their eyebrows using tampon strings. I also gained hands-on experience working various jobs throughout my sentence. The idea for my popcorn business, Comeback Snacks, actually came to me while incarcerated. Popcorn kernels were one of the few foods freely available, so I began experimenting with different flavours based on suggestions from my fellow inmates. One of our signature flavours, Jailhouse Cheese, was created by pouring Kraft Dinner cheese powder onto a bowl of popcorn. 

Popcorn became a blank canvas for my creativity, and before long, I was obsessed with crafting new flavours. I never would have come up with the idea for Comeback Snacks without experiencing prison firsthand and confronting the stigma society often places on people like me.

My story isn’t unique—many successful businesses are led by formerly incarcerated people. Queen Coffee Bean, a coffee roaster in North Carolina, and Conbody, a gym in New York, were both founded by people who’ve served time. These entrepreneurs use their creativity and ingenuity to redefine what’s possible after incarceration. Employment agencies like Cornbread Hustle in Texas are also helping people find meaningful, sustainable careers after their release.

After I was released on parole in 2018, I remember how nervous I felt every time I saw the criminal record question on job applications. After countless rejections, I finally landed a customer service job at a gym by being honest about my past and adding the work I’d done while incarcerated to my resume. It paid minimum wage and offered little room to grow—but it was a start.

That experience made it clear just how difficult it can be to find work after incarceration. It’s part of what motivated me to co-found Comeback Catalyst with Lucy Cullen—a new program designed to help formerly incarcerated people launch their own businesses. Participants share their business ideas, and we provide the resources and expertise they need to bring them to life. This commitment to empowerment is deeply personal to me. In fact, the first person I hired at Comeback Snacks had also been incarcerated. His hiring, combined with my own experiences, reinforced my determination to break down the workplace and societal stigma faced by people with criminal records.

Several people I met in prison had committed crimes for financial reasons. Supporting incarcerated people in developing their business ideas not only helps them build stable livelihoods but also brings a whole population ready to contribute to the workforce–something that could help Canada’s ongoing labour shortage. When I speak with Comeback Catalyst applicants, I’m always proud of their achievements. I’ve been on the inside, heard my idea was foolish, and told no one was going to buy popcorn from someone with a criminal record like me. 

My first call with these participants focused less on business and more on expressing gratitude for their efforts. They’ve defied the societal narrative that a person’s life is defined by their worst day, using Comeback Catalyst’s resources to turn their ideas into reality. It’s exactly the kind of program I wish I’d had when I was starting Comeback Snacks.

Related: Six organizations offering support for entrepreneurs from underserved communities

I ultimately succeeded because of the people who supported me along the way–like my family, who encouraged me to share my story, and the Corrections Canada staff at the halfway house, who helped me buy my first supplies. Churches and event organizers also stepped up, donating and hosting events to support my business after hearing my story. To me, Comeback Snacks is truly a community-built company, shaped by the support of so many throughout the journey.

When I entered prison, I was determined to change my life for the better and to reconcile with my family after the immense pain I caused them. I hope my story and the slowly shifting attitudes towards prison reform can help reduce stigma, and ensure formerly incarcerated people are treated as the valuable members of society they are.

– As told to Alice Boyle

Emily O'Brien
Emily O'Brien
Emily O’Brien, founder of Comeback Snacks, started her popcorn company after serving a four-year federal prison sentence. Drawing on her entrepreneurial background, she launched the brand to challenge stigma against people with criminal records. Today, her popcorn is sold in over 1,200 locations across Canada and the US.

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