From Prison to Popcorn: Emily O’Brien’s Comeback Snacks Story

A Trip to St. Lucia That Wasn’t What She Thought

Emily O’Brien grew up in Canada, went to Catholic school, graduated university with honors, did an internship for the Ministry of Foreign Affairs in Indonesia, and lived with a Muslim family there for two stretches of three months each. By any outside read, she was the last person you’d expect to end up shackled in a Canadian courtroom on a drug charge. That’s exactly why I wanted her on the show.

When Emily and I talked, she walked me through how a guy she’d been dating, a customer of her social media company, talked her into a trip he sold as a sober getaway. The first three days were normal. Pool, beach, the usual. On the third day, he started using and told her they weren’t going to the pool that afternoon. They weren’t there for fun.

They ended up at a house Emily described as looking like a bed and breakfast. A grandma, maybe a kid. No guns, no threats from the people at the house. But the boyfriend had given her passport to a woman there before she even knew what was happening. That woman took her measurements, made her a set of bike shorts with pouches sewn in front and back, and took her shopping at the duty free to pick out a dress that would cover the smuggling gear.

“I’m so confused as to like really like what’s going on,” Emily told me. “I didn’t know how this all worked so it was all just like whatever happened next happened next.”

She wasn’t threatened by the people at the house. She was threatened by him if she didn’t go through with it. So she went along, hoping she could just get home.

The Walk Through Toronto Customs

On the last day, she made a choice that surprised me when she said it. She didn’t drink. Most people in that spot would do anything to numb out. She wanted to feel exactly what she was feeling.

“I’m not hiding how I feel,” she said. “I made that conscious choice and it was the best decision I think I have ever made.”

The boyfriend had promised her she could ditch the drugs in a bathroom at Toronto Pearson and hand him the backpack. As soon as they landed, she went to do exactly that. He grabbed her and told her it was too late. He’d never planned on taking those drugs off her. He’d done these trips before, which she only found out when he was trying to calm her down on the way to the airport.

They got through the first checkpoint. The officers asked how long they’d been gone. One minute he said she was his girlfriend, the next minute he said she was his friend. The stories weren’t matching. They picked up their bags, handed over the slip of paper Canadian customs gives you when you land, and got sent to secondary.

The officer asked Emily if there was anything she wanted to clear up before they did a physical search. She stared at the floor too long. The officer had to ask twice. Then she looked up at the boyfriend.

“The loudest silence,” Emily told me. “You know that expression like the sound of silence is deafening. I looked him right in the eye and I said yeah.”

A female officer searched her. The drugs tested positive. She was under arrest.

A Year of House Arrest, Then the Bus

Emily’s parents had to put up an assurity to get her out. Two kilograms of cocaine isn’t a charge you bail out of with a phone call to a friend. She spent close to a year on house arrest waiting for the case to move. She was alone, she couldn’t really talk to anyone about the case, and the first year was, in her words, hell.

She wanted to take it to trial. She wanted to prove that the boyfriend had set her up. But she did the math.

“I’m not going to go up to trial against drug cartel whoever they were in that world,” she said. “I brought those drugs over that line and that was it.”

She pled guilty. Because of the weight, there was a mandatory minimum of four years.

Before she went in, she did what someone with a university degree does. She researched. She volunteered with the John Howard Society to help them with their social media, and through that volunteer work she met a woman who’d been to the exact same prison for the exact same kind of charge years earlier. That woman became her coach, her mentor, and a friend who helped her family through it.

When the federal transfer bus finally came, Emily got shackled hand and foot, then shackled to everyone else on the bus. The heat was blasting. It was January in Toronto, everyone was wearing winter coats, the bus picked up women from other jails, and nobody got a bathroom stop. One woman wet herself.

At processing they took her prints, the sides of her hands, the whole nine yards. She got placed in medium security because she had no prior history and her charge wasn’t violent. In medium, she lived in what the prison calls a house with women convicted of all sorts of things, including very violent crimes, because once you’re past the first two years of a murder sentence in max you can be reassessed down.

Drug smuggling, she said, wasn’t a charge that got punished socially inside. She ended up being the class clown. People asked her what she was even doing there.

Why Popcorn

Here’s the part I love. Emily didn’t sit in that prison waiting for her sentence to run out. She decided going in that she was going to do something good with the situation and that she wasn’t going to hide from it.

“People want to cancel anyone for anything these days,” she said. “And I was like no one’s going to cancel me. People might not like what I have to say and still be upset by this. But I’m going to do the right thing and take accountability.”

In medium, the women cooked their own food. There was a small kitchen and access to ingredients off the canteen, and people would make dishes from home and tell each other their stories around the food. Emily said it over and over in our conversation. Food brought everyone together. Everybody wanted a second chance, and food was the place that happened.

Popcorn was a popular snack inside. It was also one of her favorites. She’d struggled with food issues before she got there, and she was careful about what she put in her body now. She started experimenting. There weren’t real spice shakers, so she’d buy KD powder, the Canadian Kraft Dinner cheese mix, off the canteen and dust it on popcorn. Whatever she could get her hands on, she’d try.

That experimenting turned into Comeback Snacks, the company she runs now. It’s in more than a thousand retail stores across North America. She’s also mentoring and employing formerly incarcerated people, which is the part that actually matters to me. Anyone who’s done time knows the hardest thing on the back end isn’t the time itself. It’s getting somebody to give you a real shot when you walk out. Emily lived it, and now she hands that shot to other people.

What Stayed With Me

A few things from this conversation I keep thinking about. Emily was raised by loving parents. She went to church on Sundays. She graduated with honors. She traveled the world on her own as a kid. None of that protected her from a guy who’d been quietly setting her up the whole time he was helping her walk her dog and fixing her car.

She was clear with me about that part. She didn’t dress it up. He’d done good things for her. She still sees some good in him somewhere. She also told me he’d been investigated for the same trips before he ever brought her down to St. Lucia, and that the investigators went through her after the fact and found nothing. No financial incentive, no involvement in the operation, no plan.

The other thing she said that I want to leave you with is about that moment in the airport when she chose not to drink. She knew the safest move was to get out, not to try to blow up somebody else’s drug operation from inside another country with a phone call. Nobody was coming to save her. She wasn’t going to sabotage what he had going, because those weren’t her drugs and that wasn’t her fight. But she also wasn’t going to protect him anymore by hiding how she felt. When the officer asked, she answered.

Four years later, she’s running a popcorn company in over a thousand stores, hiring people who came out of the same world she did, and telling the story straight. Go check out comebacksnacks.com. The holidays are coming up and she has more flavors than you’d believe.