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The Entrepreneurial Edge: Ingenuity, Resilience, and Persistence

The Entrepreneurial Edge: Ingenuity, Resilience, and Persistence

The challenges facing business leaders and owners today are exponential, fueled by the advancement of technology and a rapidly changing world. Markets shift quickly, customer expectations keep rising, and the way we work, connect with, and serve people is constantly evolving.

Business success comes to those who can adapt, persevere, and show resilience in the face of adversity, embracing innovative thinking to keep moving forward. No one exemplifies this mindset more than Canadian entrepreneurs, whose very livelihoods depend on their ability to read shifting tides and move with them.  

We’re proud to represent some of these very people, entrepreneurs who have overcome incredible challenges and come out stronger on the other side. Their stories could be Hollywood movies from a founder who launched a business only to learn it was illegal, to starting a new retail brand behind bars that is now sold in major grocery chains across North America, to spotting a gap in an established industry and transforming it into a fast-growing business that has changed the very landscape it operates in.  

Meet some of these entrepreneurial speakers below and discover how their stories are helping to build a stronger, more innovative, and resilient business sector in Canada.

The Resilient Entrepreneur

Graham Sherman

Graham Sherman

Multi-Award-Winning Entrepreneur and Leader | Innovator

Graham Sherman is a self-professed “high level geek” who used his love of technology to disrupt an entire industry. In 2013, Graham took homebrewing “too far” when he quit his well-paying, stable government job to jump head-first into the craft brewing industry, launching the Tool Shed Brewing Company. What was originally a hobby in his backyard tool shed is now a 22,000 square foot brewery with product sold in over 1000 locations.

A success story for sure, but the road to get there is nothing short of extraordinary. Shortly after launching, Graham learned that his new-found vocation was actually illegal in his home province of Alberta. It took one year of relentless perseverance for the Alberta Gaming and Liquor Corporation to change their legislation, but he walked away victorious.

This win led him to open his first on-site taproom in 2014, which later evolved into the current Tool Shed Beer and BBQ restaurant experience in 2020. Then COVID hit. Overnight, Graham lost 75% of his business. He looked for innovative ways to keep his doors open, including teaming up with a local food delivery business to convert his brewery into their storage facility, but with operating costs still hovering around $250,000 a month, the math was brutal: no beer sales, no revenue.

To make matters worse, Graham’s bank decided not to renew their business loan, leaving him $400,000 in debt with no financial support and his investors moved to take the company from him. In the face of financial ruin and the loss of his beloved brewery, Graham’s legal team discovered an innovative loophole that allowed him to outline a pathway to buy back his own business instead of declare bankruptcy, and the courts sided with him.

That was in early 2024. By June 2025, Graham found himself in the extraordinary position of smoking and serving brisket for the presidents and prime ministers of some of the world’s most powerful countries at the G7 Summit in Kananaskis, Alberta. Then just over a year later, WestJet announced that Tool Shed would be sold on all flights as their exclusive onboard beer provider.

Graham’s entrepreneurial journey is a masterclass in perseverance and innovative thinking. His high-energy, high-fun keynotes take audiences through the moments that nearly broke his business and the creative solutions that saved it. Whether speaking to entrepreneurs or corporate teams, he leaves audiences with the mindset to challenge assumptions, push through setbacks, and find opportunity where others see roadblocks.

The Comeback Entrepreneur

Emily OBrien 2026 Headshot

Emily O’Brien

Founder and CEO of Comeback Snacks

An award-winning entrepreneur, Emily O’Brien built a social enterprise that began in the most unlikely place: a prison cell.

Emily is the founder of Comeback Snacks — “popcorn so good, it’s criminal”. The idea took root while she was serving her sentence, inspired by the creative seasonings her fellow inmates used to dress up popcorn. Refusing to let her circumstances define her future, she began laying the groundwork for the business from behind bars — coordinating market research and branding through hand-written letters. Upon her release, she scaled that groundwork into a brand now sold in more than 1,200 stores across Canada and the US. The company hires formerly incarcerated people, and Emily has since co-founded Comeback Catalyst, a non-profit that teaches business skills to people who’ve been through the justice system.

Recovering and rebounding from difficult circumstances is easier said than done but not impossible. In her deeply personal and inspiring keynotes, Emily breaks down her proven “comeback blueprint”, designed after successfully navigating the criminal justice system and the world of entrepreneurship. Through sharing the highs and lows of building her business, she speaks candidly about the guilt, anger, and embarrassment that followed her mistakes, and how taking ownership of her past became the foundation for everything she’s built. For entrepreneurs and corporate audiences alike, she makes a powerful case that kindness and resilience are non-negotiable, and that a setback is never the end of the story.

The Barrier-Breaking Entrepreneur

Alicia Woods Headshot 2026

Alicia Woods

Award-Winning Entrepreneur | CEO, Covergalls Workwear

Alicia Woods spent years working in an industry that wasn’t made for her, so she decided to change it.

Raised in a mining family, Alicia dreamed of following in her father’s footsteps. But at 21, stepping into mining equipment sales, she quickly discovered the industry had no room — literally — for women. No facilities underground. No proper safety gear. Just ill-fitting coveralls and the expectation to make it work.

Instead of quitting, Alicia grabbed a seamstress and created her own solution. When other women started asking where they could get one of her custom coveralls, she realized she wasn’t just solving her problem, she was filling a massive market gap.

Alicia is now the founder and CEO of Covergalls Workwear, a venture she successfully pitched on CBC’s Dragons’ Den. She has spent more than 20 years breaking barriers in the mining industry, with Covergalls now offering a full line of women’s workwear with its products sold in Mark’s Work Wearhouse stores across Canada. The brand’s success led her to expand into menswear, making Covergalls a one-stop shop for companies looking to outfit their entire crew.

In her keynotes, Alicia shares how she turned years of frustration into a business that is changing the way an entire industry outfits and supports women. Drawing on more than 20 years of breaking barriers in mining, she shows entrepreneurs and corporate audiences alike how to spot opportunity in what others accept as normal, push forward in the face of skepticism, and turn inclusion into a competitive advantage.

Hire an Entrepreneurial Speaker for Your Next Event

Our entrepreneurial speakers have turned some of the toughest setbacks in business into lasting success. They bring those hard-won lessons and insights to the stage with keynotes that equip audiences with practical strategies for navigating change, overcoming adversity, and turning obstacles into opportunity.

Contact our team today to learn more and to book one of these speakers for your next event.

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