As someone who’s passionate about meaningful work, personal growth, and the people behind the projects, I’m always energized by conversations with leaders who’ve built something from the ground up. I recently had the chance to sit down with one of our clients, Glen Demetrioff—an IT entrepreneur, family man, and culinary enthusiast—whose cottage build we wrap up this fall. What began as a chat about design quickly unfolded into an honest and thoughtful reflection on his journey through business, family, and the pursuit of purpose.
To understand where that journey began, I asked Glen to take me back to the early days.
Q. Can you take us back to the early days — your journey, what kind of business did you build, and what first sparked the idea to start it?
A. “My wife and I built a software business called DMT Development Systems Group Inc. that had grown from two employees to over 300. It was staggering how it grew over the 25 years we owned it. But the starting line wasn’t when we created DMT but many years before that. Prior to DMT, I was accumulating business knowledge, life lessons, learning theory, experiencing failure and hardships—all of which were the building blocks required to start DMT.
Turning back the clock to my Junior High days, I credit my grade 8 math teacher, Mr. Hildebrand as the reason why software played a huge role in my life. Mr. Hildebrand received the first shipment of Apple computers for the school, and he let me skip recess and stay late to play around and explore programming. There was no formal curriculum at that time, so everything was self-taught. I found programming extremely interesting, and you could say, I got hooked.
While in Junior High, my brother and I had started a small business called Thunder Bay Tackle Manufacturing. We had lots of small, tedious assembly processes to deal with and that’s when the lightbulb went on. I was able to apply software methodology that I learned to help streamline some of our workflows and improve productivity. It was very cool to see how software could solve real business problems. But what I also learnt the hard way is that software is only an enabler—it doesn’t manage your business for you. Eventually, poor management took its toll, and we lost everything…and I mean everything. I had dropped out of university to focus on the business so even my education was now years behind. Even though I was bankrupt and failed horrifically, I had learnt so much in terms of business management. Deep down, I kinda felt there would be a next time. I was 20 at the time.
From the fishing business, I got into the car business. I worked at a local Toyota dealership in sales. While there, I dusted off my programming skills and wrote software to automate lease calculations for salespeople. Lucky for me, it got the attention of Toyota Canada. In 1995, Toyota Canada asked me to present the leasing software at a sales manager’s meeting in Kelowna. After that meeting, dealerships wanted to buy the software, and that sparked the idea to start another business. I began selling the software commercially in 1996, left the dealership in 1998, and that’s when DMT Development Systems Group Inc. became full-time. Sharon and I incorporated it, and I brought in a partner in 1999. Together we grew the company from there.”
Q. What inspired you to pursue entrepreneurship in the first place?
A. “Probably my dad. My dad was a big believer in me—he was my biggest advocate outside of my wife & daughters. He taught me to have no fear and to keep trying.
There was one time I remember when my brother and I had the fishing tackle business—it was a Saturday morning. The business needed more sales and since I was in school, I couldn’t visit any potential clients during the week. So, I put on my suit, assembled my samples in my briefcase, and was getting ready to walk the two kilometers to Canadian Tire on Portage Avenue when I heard my mom whisper to my dad “Mel, we’ve got to talk to him.” My dad called me into the room and said, “You can’t go to Canadian Tire.” I was crushed. It was the only time he ever told me not to try something, but he just knew it wasn’t the right time. Other than that, he always supported me. That belief meant everything.
Q. Could you share a pivotal moment or decision that significantly impacted your career?
A. “There’s one that really sticks out. Since I didn’t have any formal training for programming, I was stuck on compiling my software code—which is essentially a lock so someone couldn’t reverse engineer it. I found a book from a publisher in California, and I reached out to the author through the publisher, thinking nothing would come of it. But two weeks later, he called me.
He explained the in’s and out’s of compiling, and then he mailed me a compiler on a 3 ½” floppy disk. A couple weeks later, I got the disk and it worked. That changed everything. It was the missing piece I needed to have production-ready software.”
Q. Looking back, what kind of legacy did you want to leave through your business — and do you feel you accomplished that?
A. DMT was an extension of who I am in real life. The business served my family with purpose, and it had a start date and an expiry. I’m not sure if I have a specific legacy goal but in general, I hope my journey inspires others to never stop learning, to keep creating, and to challenge the status quo. To take a stand for bold ideas regardless of where they come from, to set the bar high for fairness to employees, and reward loyalty.
While the truth of a legacy is ultimately decided by others, I do feel I delivered on these—or at the very least, tried with everything I had.
Q. How did that chapter of growing and eventually selling your business shape who you are today — as a leader, a husband, and a father?
A. “When you have too much on your plate—too much work, too much travel, too many commitments—it all takes time from other things. Sometimes you don’t realize what you’re taking for granted until it’s gone.
I think it taught me that the pursuit of “more” never ends. There’s always a bigger car or better boat. But none of that means anything without the right people around you. All the things you acquire are just empty shells until you fill them with people.”
Q. After selling the business, what shifted for you and Sharon — in mindset, priorities, or how you spend your time?
A. “Exiting the business helped us replay how the business affected our family over 25 years. What we learned was the importance of boundaries and communication. Boundaries are needed for work, family, and even friends. We identified a pattern that when boundaries and communication weren’t applied, when support was blurred from stress, it turned to be a very difficult period in our lives.
Today, we know the boundaries—our limitations—to ensure we remain aligned and supportive for our next chapter. For me, cooking and business is a part of my DNA so for my next chapter, I’m opening The Forge Bagel Co. with my oldest daughter. For Sharon, she is spending more time gardening and providing amazing support for our children. Together, we are spending more quality time. Whether that’s traveling, catching up on lost time with friends, or quieter moments of talking without rushing out the door. It’s been a great transition.
Q. Why did building a cottage feel like the right next step for you and your family at this stage in life?
A. “Our family is expanding, and we need more living space. We needed more bedrooms, the bigger kitchen, all the things. But I’ve told our kids—even with a beautiful cottage—it means nothing unless we fill it with the right people. It’s a thing. A really nice thing. But it only becomes meaningful when it’s filled with connection.
Building a new cottage wouldn’t even be a consideration unless we found the right builder. We knew of Pine Creek many years before from a Cottage show we attended. We met Josh and our positive impression of him lasted for many years until we called him again. We had a rough idea of what we wanted but the discovery meeting at Pine Creek made it feel real and obtainable. Sharon and I knew it was the right fit.”
Q. What does “dream cottage” mean to you now — what kind of lifestyle or environment are you creating out there?
A. “To Sharon and me, a dream cottage is a hub. A place where people come together, relax, enjoy the outdoors, but also feel that warmth inside—the warmth of a fire, of companionship. Game nights and family time.
Our favorite place in our former cottage was the sunroom. We had many great memories there and lots of cribbage! We think the sunroom in the new cottage will be the same—where everyone clusters, even though the whole place is beautiful.”
Q. Was there a moment during the design or build that really made it feel real — like, “This is exactly what we hoped for”?
A. “I don’t know if there was one single “aha” moment. It was more like a marathon—the small stuff. Every step with Pine Creek gave us reassurance. Every interaction made us feel grateful and confident to move forward. Even the site—just how clean it was—made it feel like ours.”
Q. When choosing a builder for something so personal, what were you truly looking for in a team or partnership?
A. A can-do attitude and transparency. Transparency means there’s trust—nothing to hide. If something couldn’t be done, you looked at it and tried. We never felt shoehorned into someone else’s vision.
You guys were always accommodating. Even small things—like when Sharon asked for a redesign of our walk-in closet late in the process—you just did it. That says a lot. We’ve built six homes in our family. This one stands out for the professionalism, the partnership. It felt like family.”
How would you suggest we communicate that kind of experience to people?
“Honestly, it’s hard. People must pick up the phone and talk to references. That’s what convinced me. You can’t convey it in a slogan or a marketing message because every company says they are awesome or whatever. It’s only through real conversations with real people that you can separate marketing from reality. The Pine Creek team is, in my opinion, a gold standard for builders. Every single reference I called said the same thing to me and now my wife and I have experienced it as well. It doesn’t mean Pine Creek is perfect—there are so many moving parts to building a cottage, and things come up—but it means when an issue does surface, it’s dealt with professionally and resolved fairly. What more can anyone ask for?”
Q. What’s Next for you Glen?
A. “As I mentioned, I’m starting something new—The Forge Bagel Co. It’s a passion project based on baking and culinary experiences. My oldest daughter, Rachelle and I are leading it, and the rest of the family is cheering us on. We’re opening Fall 2025 in St. Vital at 692 St Anne’s Rd. It’s about doing something meaningful and building something that represents the values of my family.”
Glen’s story is a reminder that success isn’t just about what you build—it’s about who you build it with, and why you started in the first place. From humble beginnings of writing code in his parents’ basement, to presenting to Toyota Canada, to building a cottage designed for connection, his journey has always been rooted in purpose. It’s not the titles, milestones, or even the final product that leave a lasting impact—it’s the relationships, the risks, and the values you carry with you along the way.
