Every business starts with a story. But not every story begins the way you expect. Some are shaped by uncertainty, setbacks, and the moments that force you to start again.

On March 23, women entrepreneurs, business owners, ecosystem partners, and community leaders gathered at Bayview Yards for Purpose, Resilience and Building a Business with Conviction – an afternoon event filled with honest, candid conversations, practical insight, and meaningful connection as part of Invest Ottawa’s International Women’s Month programming.

Attendees were greeted on entry by a building that was already buzzing with activity, as the event provided an opportunity before and after the keynote presentation to explore local businesses through an on-site Women-led Small Business Marketplace, where they could meet founders and discover products and services built across Ottawa’s entrepreneurial community.

While the afternoon’s theme of resilience carried undeniable weight, the atmosphere remained energetic and lively. And throughout the afternoon, there were moments of insight, connection and lightness that helped balance the incredible stories being shared.

Overall, the message for the afternoon was clear: there is no single path to entrepreneurship, but purpose, resilience, and community can carry founders forward.

An Afternoon of Conversation and Connection

The event opened with a welcome from Ashley Clark, founder of Bougie Birch, who grounded the gathering in place and purpose. She reminded attendees that Bayview Yards sits on the unceded territory of the Algonquin people and at a historic intersection of trade, movement, and exchange.

In recorded opening remarks, Invest Ottawa President and CEO Sonya Shorey framed the afternoon as both a celebration and a reflection on what it truly takes to build.

“Today is all about celebration. But it’s also about something deeper,” she said. “It’s about resilience, courage, elevating others, and it’s about what it truly takes to build, especially when the path forward isn’t very clear.”

Shorey emphasized that women entrepreneurs are not only building businesses but shaping stronger communities and creating opportunity for others.

“Because when women build, we don’t just build companies. We build stronger communities,” she said. “We build opportunity, and we help shape a more inclusive, sustainable, and prosperous future for everyone.”

Emily O’Brien’s Comeback Story: Building a Business From Behind Bars

The centrepiece of the event was a keynote from Emily O’Brien, founder of Comeback Snacks, whose story challenged assumptions about people, incarceration, entrepreneurship, and what it means to rebuild after setbacks.

O’Brien shared how her business, now carried in more than 1,200 stores across Canada, began in one of the most unlikely places imaginable: federal prison.

What followed was an unflinching account of addiction, coercion, incarceration, and the long process of reclaiming her life.

O’Brien was incarcerated after being coerced into transporting drugs across international borders, an experience that led to her arrest and a period of incarceration in Canada. In the aftermath, she faced the challenge of rebuilding her life, navigating stigma, and redefining her identity beyond a single moment.

She moved through painful chapters with striking honesty, offering occasional moments of lightness that helped the audience stay connected to a difficult story. That balance shaped the energy in the room.

Despite the seriousness of the subject matter, the audience leaned in, open and engaged, to hear more about her journey. She shared details of her time in prison, and how moments of connection and creativity began to shift her perspective.

Popcorn, a simple and widely shared snack, became something more.

“I didn’t meet inmates. I met moms, artists, writers, chefs,” she said, reflecting on the people around her. “People that were way more than just that.”

As they experimented with flavours, such as using mac and cheese powder and calling “prison cheese”, popcorn became both a creative outlet and the spark of an idea.

“Every kernel pops differently… if you put it under too much heat, it’s going to burn. If you don’t put any heat under it at all, it’s not going to pop,” she said. “It’s really all about your environment that determines how you can pop and thrive.” – Emily O’Brien, Founder of Comeback Snacks

That perspective carried into how she began to understand her own experience.

“I was 26 years old… I did one thing, like, on one day. So, I wasn’t going to be labelled for the rest of my life for that,” she said.

Supported by her family and the founders she connected with along the way, O’Brien made a decision to take ownership of her story rather than hide from it.

“I decided I was going to own the story,” she said. “My story ended up being my biggest asset.”

That decision became the foundation for Comeback Snacks, a brand built not only around product, but around purpose.

Since launching the business, O’Brien has created employment opportunities for people with lived experience of incarceration and continues to advocate for redemption, reintegration, and opportunity.

Even the brand itself reflects that perspective. With a tagline like “popcorn so good, it’s criminal,” O’Brien used humour and a new perspective as a form of ownership, reframing a difficult past into something creative, memorable, and unapologetically hers.

The Comeback Blueprint

As part of her presentation, O’Brien introduced what she called the Comeback Blueprint, a practical framework shaped by her own experience. The principles included commitment, ownership, morality, education, belief, accountability, courage and kindness (comeback).

Together, they formed the backbone of her message: comebacks do not happen by accident. They’re built step by step, through decisions, action, and a willingness to reframe the situation despite setbacks – and push ahead.

She also tied her framework to the International Women’s Day theme for 2026, Give to Gain, emphasizing that support does not always come in the form of capital, but through time, belief, and shared experience.

“A comeback is not proven by how far you go,” she said. “It’s proven by how many you actually bring with you. And that includes all of you in this room.”

As the audience applauded, O’Brien’s story moved beyond a personal narrative and became a shared framework for the room. Her message was not about overcoming a single challenge, but about choosing, again and again, to move forward.

A Conversation on Confidence, Reinvention and Being Underestimated

Following the keynote, O’Brien joined Sueling Ching, President and CEO of the Ottawa Board of Trade, for a fireside chat and moderated Q&A that drew out some of the afternoon’s most resonant moments.

Ching’s questions focused on reinvention, confidence, and what it means to keep moving when people underestimate you.

In the exchange, Ching noted that many women in the room had likely experienced assumptions being made about them because of their past, their circumstances, or simply because they are women, and asked O’Brien’s advice on convincing the doubters “without shrinking?”

O’Brien’s response was direct. “I just stopped trying to convince. I just did it,” she said. “I just learned. I did everything that people said I couldn’t do.”

“Selective hearing for good,” she added with a laugh and a shrug.

That same clarity and humour carried through the broader conversation, as she reflected on the emotional challenge of re-entering the world after incarceration, learning to advocate for herself, and quieting the need to view herself through other people’s judgment.

She also shared practical advice for anyone at the beginning of their own comeback, encouraging them to take one decision they can stand behind and act on it.

“Whether it’s starting something, stopping something, meeting someone, emailing someone… do that one thing,” she said. “And then once you get to that habit of making a decision and acting on it, it becomes a lot easier, and then you just do it.”

As she continued, she shared with the audience the power of community, for anyone looking for the drive to recover, to comeback or to start something new.

“Anyone can do it. Everyone has fallen; everyone has made mistakes. But it’s easier to make comebacks when you share your struggles with others,” she said. “Obviously at the beginning I didn’t want to talk to anyone about it, but then the more I did, I was like, oh my gosh, I didn’t realize it resonated with so many people, all over the world.”

“Definitely, can’t make comebacks alone,” she added in closing.

An Experience Built Around Community

Beyond the stage, the event was designed as a shared experience.

The Women-led Small Business Marketplace, hosted by Invest Ottawa’s Small Business Enterprise Centre, showcased local entrepreneurs offering products and services rooted in creativity, resilience, and purpose.

The space created opportunities for attendees to engage directly with founders, support local businesses, and build new connections.

A special thank you to the sponsors and partners whose contributions helped bring this event to life, including Rogers and Nelligan Law, and core contributions from the Government of Canada, the Government of Ontario and the City of Ottawa.

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Learn more about International Women’s Month at Invest Ottawa

• Explore upcoming events, and learn about International Women’s Month at Invest Ottawa: investottawa.ca/iwm
• Hear about the event from CTV Ottawa.
• Explore the Featured Leaders Series -collectively, these amazing women lead with purpose, champion inclusion, and actively mentor and support the next generation of founders and executives.