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This Is How She Does it: This Popcorn Entrepreneur Makes $85,000 Per Year and Talks Destigmatizing the Ex-Convict Label

Emily O'Brien poses in a striped black and white shirt with bags of popcorn
Girl And A Camera

After serving a four-year sentence for drug smuggling, Emily O’Brien left prison with a kernel of an idea. During her time in a 10-woman prison unit, she’d encountered a plethora of recipes from a variety of backgrounds. One universal beloved treat, however, stuck with her: popcorn.

As the founder and creative director of Comeback Snacks, the entrepreneur launched her popcorn shop nearly three years ago before opening a brick and mortar location in Hamilton, Ont. With a goal of not only launching her own business, but giving back to the community in some way, O’Brien made a point of hiring ex-convicts, offering them the employment opportunities that otherwise might not be made available to them.

“I wanted to fight for something that was right and that was creating second chances for others and changing the stigma around formerly incarcerated people,” she says.

Now, with her delicious products sold in more than 250 stores across Canada, O’Brien continues to employ ex-convicts like herself to help her run her business and meet supply-and-demand. It’s also part of her business mandate to align with various organizations that work with at-risk youth, reformed convicts and those battling addictions.

As for her favourite Comeback Snacks popcorn flavour? “Currently, it’s peanut butter and chocolate caramel, but we are launching a savoury line in January and there’s going to be lemon pepper dill.”

This interview has been edited and condensed for clarity. The views and opinions expressed in this interview are those of the interviewee and do not reflect the position of and any of its affiliates.

Emily O'Brien poses in a rattan chair in a leather jacket
Girl And A Camera

What’s your official job title and salary?

I’m a creative director [of Comeback Snacks]. I have a great business partner and he kind of does the nitty-gritty spreadsheets and operations that definitely aren’t where my strengths are. My work involves partnering with organizations and participating in speaking engagements, going to events and visiting stores and creating content around the stuff that we do and the people we’re trying to serve. [As for my salary], I put everything I make into the business, but because I do a number of speaking engagements and workshops, I take home about $85,000.

Related: This Is How She Does It: This ER nurse makes $67K a year and opens up about healthcare during the pandemic.


What inspired you to start Comeback Snacks?

I started Comeback Snacks when I was incarcerated. I was basically trapped on vacation with my former partner who told me I had to bring drugs back over the border with him to get back into Canada and I was scared, confused and wanted to go home. So I did it and got arrested. Two-and-a-half years later, I was sentenced to four years in prison and while there I saw how much food brought people together and also how much talent people had and how there’s a lot of anxiety and insecurity about re-entering the workforce [after prison], so I wanted to be a part of changing that narrative for myself and also for others.

I’ve always had an entrepreneurial side — a very feisty side to me — and I wanted to fight for something that was right and that was creating second chances for others and changing the stigma around formerly incarcerated people.

When we first started [Comeback Snacks], our first hire was actually a male and then he moved out of the city. If someone comes to us and they want a chance or somewhere to work or get back on the right path, we kind of say yes to everyone as long as they’re really willing to work with us. If we don’t have the capacity, because sometimes we get so many requests, we now have partnerships with Goodwill Canada (who has a partnership with Corrections Canada) and other organizations that help provide employment as well. So we’ve extended our network of employees from internal to other organizations as well.

Related: 10 things you should negotiate before you start a job.


a variety of Comeback Snacks popcorn products on a table
Girl And A Camera

Tell us about your food experiences while in prison.

A lot of people don’t know this, but in women’s federal prison we actually have to cook our own food. We have access to a limited number of ingredients and some of those things were spices and popcorn, so we kind of threw together different [seasoning] recipes. Popcorn wasn’t the only thing, but it really resonated with me because I’ve always liked to eat healthy and there aren’t a ton of popcorn companies out there that go the healthier route [while also doing] something good for the community.

We all lived in little units, so there’s like 10 women per unit. It was like a small house, and we had a little kitchen in there with two fridges where everyone had their own space and their own food. We had pots and pans. We didn’t have cookbooks, but that was something we shared with each other — our knowledge of cooking. We would eat different cuisines from around the world, like Caribbean night, and everyone would cook their favourite recipe. It was really nice. It made people forget they were in prison and allowed people to share their stories. It brought a kind of peace among everyone.

Related: 10 genius money hacks we snagged from TikTok.

What is your biggest goal for both yourself and your business?

Our biggest goal is to reinvent as many lives as we can and make people feel good about their path going forward and feeling like they’re human again. We want people to feel good about their potential. Often what gets taken away is people’s humanity and their belief that they are capable of doing something more with their lives. It’s not really part of the incarceration path — it’s not something that’s encouraged. You’re not told you’re good at something or the good things you’ve done, you’re basically told ‘oh, you did this.’ We’ve all made mistakes and we’ve all gone down roads that we regret. [We want to help others] get back on their feet because we’ve all needed help in our lives.

See also: Why getting a mentor will make your career this year.


Typically, what are your hours like?

My hours are 24/7 365 days. I eat, sleep and breathe it. I wake up and I’m like, ‘OK, what am I doing today to fulfill this mission?’ I think by the time I get out the door, everything has to do with Comeback Snacks… but that’s what entrepreneurship is, right? It’s your life. But I’m very lucky in that I have a wonderful fusion of life and work, so I enjoy all of it.

You may also like: This is How She Does It: This LA-based multifaceted entrepreneur makes $231K per year.

Comeback Snacks also aligns itself with various organizations. Tell us a bit about that.

There are three organizations that we primarily work with. The first one is the Yonge Street Mission (YSM). They have a program called HOPE [Helping Offenders on Probation Excel]. The [YSM] do a number of different initiatives, but this one in particular helps at-risk youth that have maybe become intertwined in this stuff and don’t have a positive network to help them get out.

The second one is the Elizabeth Fry Society, which works directly with women who are coming out of incarceration. Often they won’t be able to feed their kids or have anywhere to live and, unfortunately, with women, there’s often a man involved. If they don’t have proper support they just go right back into that relationship that got them into prison in the first place.

The third one is Renascent. It’s where people go when they’ve struggled with addiction and substance abuse, which also correlates very strongly with incarceration.

We try to focus on three different areas that are all involved in incarceration and try to help others that are going through different things because it’s all so complicated and no one’s history is the same, so we just try to work with them and see if we can do anything.

Related: On a budget? here are 11 ways you can still support social justice issues in Canada.


Emily O'Brien sitting at her desk with her laptop open, looking at the camera
Girl And A Camera

What are some of the biggest challenges you’ve faced with your business?

Well, I’m almost done my sentence, so being on parole and trying to go to different places, it’s a challenge because I have to get approvals. I would also say, trying to do everything. You always want to be able to help so many people, but sometimes you just can’t and that can be hard. We want to do all the fundraising that we get requests for, we want to hire as many people as we can, but you can’t. You still have to be a business and pay your staff and stuff like that. So that’s why we thought we should create a way we can partner with other organizations that are hiring.

Related: Forget ‘how are you’ — this is how successful people do small talk.

How do you deal with stress or burnout?

I sleep. I’ve really noticed the importance of sleep lately and, you know, in the past 10, 15 years, entrepreneurship has been glorified by not sleeping. Also, just being alone is really important because, with my work especially, it’s very people-focused and you’re always kind of ‘on’ so it’s important to have the ‘off’ time where you’re by yourself. I also enjoy running. That’s just me, I know some people hate running, but I love it and being outdoors.

See also: 10 signs you’re heading for a burnout diagnosis.

What advice would you give someone looking to start their own business?

I would say to build it off a lived experience because that is truly a way you can help others because you’ve been through it. [But] just because it’s personal to you, it doesn’t mean it’s personal to everyone else. It’s about finding something you care a lot about that can help others and something that you’re willing to give things up for. It’s definitely not easy and there are very, very challenging days. You will get exhausted. I don’t think it’s about finding a balance because I honestly don’t think that’s true in entrepreneurship, it’s more about managing the imbalance that is part of this kind of life.

Related: I lived in the back of my store and this is what I learned.


What’s the biggest lesson you’ve learned so far about being an entrepreneur?

To own your story. Own everything. Own your failures. Own your faults, and share them. A lot of people don’t — they want to talk about how happy they are. But if it isn’t true you can’t really help people if you’re just fabricating a journey, the results or feelings because that’s just not the way that it works. You’re going to have to ask for help. If you’re struggling with something, ask for help because you don’t always have the answers. Always have a mentor and, if you already have a mentor, make sure they’re related to what you’re doing. Be selective in who you’re taking your advice from to make sure it’s legit.

Related: 16 great jobs for women in trades

What do you love most about your job?

That I wake up every day excited. I see the beauty in helping people even if it comes from answering a single text message or answering one phone call. You don’t have to do grandiose things to make a difference in someone’s life. You can really help them even by doing small things. Try to help others the way people have helped you. Then you’ll do well.

See also: 20 low-stress jobs that pay more than $100K.

What’s next for Comeback Snacks?

We just filed our trademark for the US and got that approved, and we have a second line [of popcorn], a savoury line, in January. We’ve also launched a three-part docuseries on Bell Fibe and we’re going to stream it all across Canada after the license with Bell is done and then raise money for organizations that support those who have struggled with addiction or substance abuse or have been intertwined with the law. As part of raising money, we’re also going to stream the series in theatres [in Hamilton, Ont. and Oakville, Ont. to start].

You may also like: How to start managing your money after landing your first job.


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