In this exclusive interview with CanadianSME Small Business Magazine, we sit down with Greg O’Brien , a seasoned entrepreneur and the proud recipient of the Canadian Franchise Association’s Gold Award for Franchisee of the Year in the Non-Traditional Category. Greg’s entrepreneurial journey, which started with a successful food manufacturing business and expanded into the construction industry with Hickory Dickory Decks, is a testament to his commitment to innovation, leadership, and community engagement. Throughout his career, Greg has maintained a deep focus on giving back to his local community, from supporting youth sports teams to organizing educational field trips. Greg shares valuable insights on the importance of community involvement, the challenges and rewards of franchising, and his approach to building businesses that not only thrive but also make a positive impact. His passion for community, leadership, and growth continues to shape his approach to business and life.
Greg O’Brien is a seasoned entrepreneur and business leader who earned his Commerce degree from St. Mary’s University before launching his first business at just 21 years old — a successful food manufacturing company that marked the beginning of his entrepreneurial journey.
What inspired you to become a Hickory Dickory Decks franchisee, and how has your journey shaped your approach to entrepreneurship and leadership?
What inspired me to become a Hickory Dickory Decks franchisee was the chance to combine my passion for building with my desire to do something more personal and fulfilling after years in the corporate world. I spent over 15 years in medical technology, but construction has always been in my blood. My grandfather and uncle were both master carpenters, and while I never pursued it as a career, I’ve always enjoyed building as a side project.
As a small business owner, I take pride not only in growing my business but also in contributing to my local community. When I discovered Hickory Dickory Decks, a Canadian company with a long-standing reputation and a proud member of the Canadian Franchise Association since 2005, it felt like the perfect fit. Franchising gave me the opportunity to get up and running quickly with the support of a trusted brand.
Since launching in 2022, this journey has been everything I hoped for and more. It has reinforced for me that leadership is about setting the tone, staying involved, and being a strong role model—for both my team and the community I serve.
As the recipient of the CFA Franchisee of the Year (Gold, Non-Traditional Category), what does this recognition mean to you personally and professionally, and how has it influenced your business philosophy?
I’m incredibly grateful to the Canadian Franchise Association team. Receiving the CFA Franchisee of the Year award meant a lot to me. Personally, it was a great reminder that it’s never too late to take a new path and follow something you’re truly passionate about. Professionally, it felt like recognition for all the hard work I’ve put into building a business that values quality, trust, and strong ties to the community.
The Franchisee of the Year award recognizes outstanding franchisees for their unique accomplishments and excellence in a few different areas: business performance, community service, and brand involvement. It meant a lot to me to be nominated by the Hickory Dickory Decks team, among the very strong community of franchisees within this system. But it was also an honour to be chosen from all the nominees as the Gold recipient! I’m proud that my community involvement has translated into such a prestigious award.
Community involvement is a significant part of your story, from sponsoring youth sports teams to organizing educational field trips. Can you share a specific experience?
Supporting youth in our community has always been important to me. I sponsor several local sports teams like the TASA Minor Hockey Association and the Halifax Dockers Aussie Football League, and I also help individual kids cover fees or equipment costs if they need it.
One recent experience that really stood out for me was organizing an educational field trip to the Discovery Centre for over 120 local students. For many of the kids, it was their first time visiting a museum, and seeing their excitement and curiosity throughout the day was incredibly rewarding. I covered the transportation, admission, and even had custom T-shirts made so every child felt like part of something special. It was more than just a day out—it was about creating a moment that they’ll remember.
These initiatives have helped me remember that it’s not just about what you build, it’s also about the people you build it for.
Why is giving back to your local community important to you? What inspired you to support youth sports in particular?
Giving back to my local community is important to me because it’s part of who I am. Supporting youth sports is something I’m passionate about because I see firsthand how important it is for kids to stay active, build friendships, and develop life skills like teamwork and discipline. When I was growing up, there was no internet, so we were always outside-running, biking, playing. Today, with technology and the challenges of modern life, it’s even more important to get kids moving and socializing. Sports can help with that.
I also understand how expensive sports can be now. From travel to equipment, it adds up quickly. So, helping local teams and kids participate is a way to make sure they don’t miss out on these valuable experiences. Whether it’s a fun field trip or supporting a hockey team, I want to help keep our community healthy, active, and connected.
Finally, what advice or message would you like to share with fellow small and medium-sized business owners who aspire to make a positive impact in their communities while growing their businesses?
I believe if you’re able to give, you should. Some people are naturally wired to give back, but even if you’re not, trying it often brings that rewarding feeling inside. It doesn’t have to be big–a small act, like organizing a field trip or supporting a local program, can have a lasting impact.
A lot of people don’t realize that franchises are locally-owned small businesses, with business owners who live in and give back to their local community. That kind of giving is important to me, and I love that as a member of a franchise system I have the support of the brand behind me.
For anyone who is considering buying a franchise, I’d also encourage them to look for the CFA member logo when they are looking at brands to invest in. Brands that hold membership in the CFA sign on to a code of ethics and represent a high standard of excellence in franchising—including a commitment to giving back!
