Emily O’Brien transformed what could be seen as an obstacle into a life-changing opportunity. The idea for a popcorn brand came to her while watching the 2018 Super Bowl and enjoying a flavoured popcorn her fellow inmates had created.
Serving a prison sentence for drug smuggling at the time, Emily used her network outside of prison to conduct market research on the popcorn industry, and a few months later, her brand Comeback Snacks became a viable business with approval from Correctional Services Canada.
When she was released from custody in late 2018, she was ready to take her business to the next level. Today, her products are available in close to a thousand stores throughout Canada.
What were you dreaming of as a career growing up? Was it something completely different from what you’re doing today?
Actually, it kind of was, and it kind of wasn’t. I think my hero when I was young was Amelia Earhart. I really always wanted to be a pilot. And I just loved how adventurous she was and how determined she was and how independent. She fought for so many things, and unfortunately, it ended up meeting her demise. But although I didn’t become a physical pilot, I think metaphorically we were all pilots of our own life.
Tell us about your journey, from going to school to eventually starting the company.
I grew up in Hamilton, Ontario. I was a middle child of three daughters, so insert middle child syndrome joke here! I was always very adventurous, very curious, very loving too. As I got into high school, I started getting into trouble because I was a little bit of a rebel. And I liked learning, but I didn’t like learning things that were forced on me.
All throughout high school, I’d really found beauty in travelling. We travelled as a family when we were young. I did all these things in different countries, and it was doing that kind of work that really made me feel fulfilled and free. When I went to the University of Guelph in Ontario, Canada, I chose International Development, so hopefully, I could turn that into a career.
But I also had an interest in nutrition. Growing up, we were always very healthy, although I did struggle with eating for quite some time. That was what led to my substance abuse issues, actually. Funnily enough, my chemistry grades weren’t good enough for the nutrition program at Guelph.
And my maths grades weren’t calculus, so I couldn’t get into business school, which is funny because, as people will know, I work in both those fields now.
Throughout university, I began to use more substances and there was definitely a big party aspect to it. After graduation, I was like, “Well, I’m just gonna try the corporate route”. So I got a job, that was when I learned that I was really good at sales.
Then, that turned into networking, which turned into running my own business in Toronto which was a social media company because I wanted to combine all my elements of travel with my elements of people. I created a company that revolved around sharing stories via social media.
That’s when the true Emily came out. Another thing that happened at that same time was that my family fell apart. I went from drinking casually to drinking for medication. I fell into some cocaine usage as well, and I knew it wasn’t good, but I also found it very easy to hide.
I knew that my motivation was going down, and I met someone through my work, which developed into a close relationship, I wouldn’t say romantic, but just very close and trusting.
And he wanted to take me on a trip. As soon as we got on this trip to St. Lucia, we had a great three days in the sand and sun, and on the third day, he tells me that we have to bring drugs back over the border.
I knew there were some red flags, but there are only red flags once we see them. I just wanted to go home. I didn’t know this world. He booked the ticket, so he had all the information on me and my family, and apparently, he was in a lot of debt, and he had told these people down there that I was doing this with him prior to our departure.
I didn’t want to play hardball. I wanted to go home, which I’m sure a lot of people would’ve done: choosing what seemed like the safest option to just get you back. You always get so many armchair experts when these things happen, right? They’re like, “You should have done this, done this or this”. But when you’re actually in this situation, you’d be surprised how quickly things change.
So on the final day of the trip, I was suited up with two kilograms of cocaine and put on the airplane with him. And when we got to Pearson [International Airport], I knew I was going to be bad at it. I was a terrible liar. I didn’t want to do it. I wanted to go home. And body language is often the loudest voice in the room, right?
Luckily, I think that saved me because we got pulled into secondary, and after they asked me questions, I said “yes”. I was concealing narcotics. And that was the beginning, a prequel to the entrepreneurial journey I’m at now.
Did you know how were you able to navigate what came next?
After I was arrested, I had to spend the first bit on house arrest with my mom because it takes a long time for these cases to go through the system, but I knew that I was going to plead guilty because, although I didn’t orchestrate this operation, I knew that I had to take responsibility.
We all have to take responsibility for our lives. And I knew that I couldn’t move forward until I stopped harbouring all this anger and resentment toward this person that had brought me on this trip. My family was under tremendous stress. On pieces of paper, it’s like you are this horrible person, but I had to look back on the rest of my life and know that this was one thing that happened one day.
I’m 26 years old, and there are 365 days in a year. I’m pretty sure for most of those days I’ve been a pretty good person. It was also hard to get beyond all those negative things that were said by law enforcement and things like that.
When I got to prison, I saw how a lot of people felt the same way. We all had maybe done things that we’d regretted or been involved in things that got us there. But also realized that I was very lucky in the sense that I did have a supportive family.
In prison, we would all make different kinds of dishes. Some people would make their favourite dish from whatever country they were from – and popcorn was a popular prison snack. We put lemon pepper and dill on it one day because we had access to certain spices. I was in a medium security unit.
I also saw a lot of creativity in there, a lot of people making their own outfits and doing amazing art, creating amazing food, writing amazing stories; just bringing people together. There was so much humanity in there, and people think prison is the opposite of that. I wanted to help change that perspective, and popcorn was that vector. So I decided to start a popcorn [business] in prison.
All popcorn kernels look the same right before they’re popped, but depending on what environment you pop them in… If you pop them for too long if you don’t put them the right way, then they’re going to get burnt. It all depends on our environment, how we pop.
When you started the business officially, was that something you did while you were still behind bars, or did that happen afterwards?
I had a year, actually. My sentence was a total of four years, but for people that don’t know, you have to serve a certain amount inside, a quarter, basically. Then you can be eligible to enter the community given the fact that you hadn’t had any infractions. Everyone gets the same chance out on a certain day after a certain amount of time.
And nothing is stopping me from getting out at this time. So I used the 11 months that I was in there to just read and write letters and learn about people, learn about the system. I had an entire library that I had access to, and I had none of the distractions.
So the idea for Comeback Snacks sparked in there somewhere.
Did you know already you wanted to start a business again because you were an entrepreneur prior to landing in jail? Or was it coming to the conclusion that it might be hard to find employment afterwards?
Finding employment is one of the big things that people are worried about. There are still a large number of organizations that will not even look at you if you have this record. When really, sometimes, if you have been through really crappy times in your life, you are strong, and you are ready to fight for something that can actually make you a really good employee.
I think it was a combination of both. I didn’t know what business I was going to start. I knew for sure I wasn’t going to write a book. I didn’t really feel like I was worthy to write a book. I knew that through the business… Because it does have a massive social enterprise element to it, which is contributing dollars to organizations that help other women, and other individuals, coming out of prison.
Also, to help people. I knew that I was going to do something, but I just didn’t know what it was going to be. It wasn’t until I had lived that experience that really got something because I was rooted in that now.
People pay 50,000 dollars for rehab. So I was like, “I’m gonna take every element of this and reframe it in a way that it’s productive and positive for me, but also realistic”. You have to know that things are really serious, and you have to treat them seriously, like a business.
A business isn’t a joke either. You can have fun elements to it, but when it comes down to it if you’re going to actually support yourself and the people you are trying to serve, you have to be serious.
When did you make Comeback Snacks official, and when did you realize the business was actually going to take off?
I knew in my heart I was going to make it take off because I believed in the cause so much. I believed in the people that I met in there so much just by seeing how misunderstood we were and how the media plays a huge role in negatively impacting people’s abilities for successful reintegration.
I went straight to the media when I got out, I was like, “This is what I’m going to do”. I know not everyone’s going to be a fan of it right away because as soon as you come out with anything that involves crime, you always have the “do the crime, do the time” people, and “she should rot in jail”.
But I knew I was expected for those, and I was already used to that language from law enforcement anyway. It didn’t really mean anything. Even in the modern world, people talk shit about people all the time, so it wasn’t really that difficult for me because. It was more like a challenge.
It was taking ownership, taking control of your narrative before other people might; which, I think, is a good lesson for any entrepreneur, any woman in business, right? Even if the circumstances are different, and they didn’t do prison time or commit a crime, often if we leave it to others, the narrative is not ours. And that can lead to so many other worse things.
So I went out, and I was like, “I owned it and this is how I’m going to fix it, and this is how I’m going to help others at the same time”. And hopefully help society as well, because there were a lot of laws in place that weren’t helpful for people coming out of prison, like mandatory minimums, for example.
Most people that have been convicted of mandatory minimums in the drug smuggling world weren’t making anything off that. It’s always someone higher up, and you’re just a used drug mule, so that someone else with more amounts could get through.
Yet they’re putting these people in jail for four years or more, which is not only expensive. It’s $160,000 a year to keep a female inmate. You don’t get to build your finances in there. You come out with $200, and with nowhere to live. So what could that money be going towards?
It could be going towards rehabilitation. It could be going towards career development or actual education. Something that could actually keep the community safer, and also keep that person safer, so that wouldn’t happen again.
Now I work with the federal government and the provincial government. I worked with law enforcement, human trafficking agencies, and it all started with popcorn. Popcorn was the vector to really explore and fight for all these changes that needed to be made.
Did you encounter resistance at first? What was the feedback when you were on the outside and starting to promote and talk about the business?
Resistance is a challenge for me. It’s a good challenge, a fight for what you believe in. I couldn’t fight for it if I didn’t go to prison, if I didn’t see it for myself, I wouldn’t be so focused on proving other people wrong and proving myself.
When I came out of there I wasn’t well known by any means, but the people that knew me knew that was not me. They knew that I was a good person. I had a lot of great support, and sharing stories in the media… It was little insults and jabs and all that stuff. But they’ve actually stopped because I’ve just walked the walk. I haven’t just talked the talk, and I’ve met so many people along the way.
Once the business started taking off, what was that first cornerstone moment for you?
When I did my first pop-up in Toronto and John Tory came. He made a Twitter post about me, and it was terrifying, actually. Because you know how Twitter is, and I was like, “Oh my God, people are just gonna rip me apart”.
Some did, but then it wasn’t that bad. It was the first celebrity that tweeted about this initiative. It’s always hard to take the hate the first time, and then after a while, you just dwindle off because you’re proving them wrong, and you know who you are. You’ve heard it all at this point, so what are they going to say?
That’s why I changed the name to Comeback Snacks. Mistakes are universal, but our comeback it’s not just about prison time. It can be coming back from not just physical prison, but any kind of prison. It can be a physical prison in the sense that you have an injury, and you feel like you can’t move.
Or mental health prison, where you feel like you don’t know who you are and or you don’t know how to say things. Or a financial prison, a marital prison. It can be a geographical prison. You might want to move, and you can’t because it’s too expensive. I think we’ve all been in prisons before, and it’s more about realizing that, and we all need each other in supportive comebacks.
What do you think you bring to your role as a leader, and how do you view leadership in general?
I view leadership as family, to be honest. When I have the individuals that we work with, they can text me whenever they want because we’re still small. But I don’t want them to be afraid of things. And sometimes they’re leading me, sometimes they’re teaching me things as well. We all have things that we can teach each other. But it also comes down to learning hard lessons as well, right?
Leadership can come in so many ways, shapes and forms, but it all comes down to honesty, being realistic, but also being able to laugh and having that family environment.
What would your advice be to women entrepreneurs who are thinking of starting a social enterprise?
Number one, for me, was my lived experience. And not things. So we all have something that we really care about, but we can’t do it alone. I think alongside that, you have to get to know the people that you’re trying to help. You have to not just work with them, but also work with other people that have built similar things.
It’s all about connection, and that’s how you can truly make a big impact. And be relentless. Be relentless with your story. Be relentless with your beliefs. You’re going to have to say it a million times. You’re going to have to say it 2 million times. But it’s also going to evolve, and the more that you share it, the more you’re going to help other people.
And that’s how you will truly find a business and work in a business that works for you, not just financially and supports you, but supports you emotionally. I call that emotional profit, and that’s how you can be truly rich.
Listen to our full podcast interview with Emily O’Brien, Founder & CEO of Comeback Snacks HERE.