Originally from Toronto, the Oldland family left city life for the small, quiet town of North Hatley after Oldland patriarch, John, accepted a job at Bishop’s University. “My dad saw an ad in the Globe and Mail in 1983 for a Business Professor at BU,” Chris shared. “He’d always wanted to be a teacher, so he quit his job running an ad agency in Toronto and we moved to North Hatley on the suggestion of some family friends who had their summer cottage there.”

Chris and brother Nick enrolled at Bishop’s College School across from BU, while young Jeremy attended North Hatley Elementary for a year before joining his brothers at BCS. “Because [our dad] was working at BU, we’d all ride in together in the morning. He’d drop us off and then pick us up after crease if he was working late.”

The spirited brothers excelled in the athletic arena, playing hockey, football, rugby, soccer, and tennis—even trying out karate. “Mr. Goodwin was a great hockey coach. Some of my most memorable moments were the hockey tournaments in the States versus Deerfield and Eaglebrook,” Jeremy remembers. “I don’t think we would know how to play hockey if it wasn’t for BCS,” pipes in Chris. “Mr. Commons was an awesome English teacher and rugby coach. One of my favourite memories is the rugby tour of Scotland—that was a blast.” And despite a perhaps lacklustre academic record, the brothers recognize how lucky they were to attend BCS and benefit from such an environment. “We were blessed with crazy good teachers and coaches,” says Jeremy. “Mr. Slocombe, Mr. MacDonald, and Mr. Trower, who ran the model airplane club—I was so into that!” As Chris adds, “You have to dedicate a lot of your time as a teacher at BCS. You’re either into it or you’re not, and—lucky for us—they were all into it.” 

Natural born risk-takers (it runs in Oldland veins!), their time at BCS further cemented the value of taking chances and learning from mistakes or perceived failures, not to mention granting second chances. Chris shared one such experience of his, courtesy of a former Head of School: “When I graduated Form VI, I left to go to CEGEP. But I quickly realized I was going to blow the year six days into it. I went to Mr. Cruickshank three days before the start of the school year and asked if he would let me come back for Form VII. He said ‘sure.’ I was really thankful for that because I definitely wasn’t ready for all that freedom yet.”

Chris may have benefitted from the then-Head’s leniency and understanding, but his younger brothers were a different story. Both were ‘advised to leave’ in April of their respective Form V years but remained friends of the school and have stayed in close touch with many of their BCS classmates. They each completed their last two years of secondary in the United Kingdom (at an all-boys boarding school that “really was not as much fun as co-ed,” quips Jeremy) before heading off to Mount Allison University. Nick graduated with a B.A. in Fine Arts while Jeremy received a B.A. Sc. in Computer Science and Engineering. Chris, for his part, studied history at UWO after finishing his Form VII year. 

After university, the brothers ventured out into the working world and were scattered across North America when their parents asked them if they were interested in taking over the couple’s small company. “Back in 1999, they were tired of running the business, and they called me and Nick and asked us if we wanted it,” Chris shared. “I was still in New York at the time, Nick was doing stand-up and making documentary films in Vancouver, and Jeremy was in Toronto working for an up-and-coming tech start-up.” It took little persuading—after all, taking risks and trying new things is stitched in their DNA—so the brothers quit their jobs, packed up their lives, and made their way home.

The brainchild of Alice and John Oldland, Hatley had humble beginnings. “It was a gift store selling candles, cards, and t-shirts. Our parents were silk-screening t-shirts and keeping them in boxes at home.” Despite its small size, the brothers agreed to take over operations on the condition that their parents give them total control. “We were all working successful jobs and would be taking a pay cut to come back,” Chris explains. The request was granted, and the senior Oldlands handed over the keys along with full rein to their three sons—and promptly took off for Europe. It was sink or swim, with the company’s future resting entirely on the boys’ shoulders.

The trio made it work by trusting their guts and one another, working hard, and always having fun. They made mistakes, they hit some bumps in the road, but they persevered. The brothers share that there is no secret formula; they simply push ideas and projects forward, and work hard. When a mistake happens—and it will, they promise!—they quickly move on, learning in the process. “We make big mistakes but we don’t dwell on them. We just say, ‘Okay I made a mistake. Now what?’ We just keep going. There is no straightforward way to growing a business. As long as you’re right 51% of the time, that’s good enough!”

There is also no time for sibling rivalry or ego in an environment where decisions are made quickly and all three are responsible for a different area of operations. “Our parents were really smart and gave each of us a third of the business, so there’s never been anything to gain in fighting. We all own the same exact amount and get paid the same exact thing,” says Chris. Jeremy agrees, adding: “There’s no point in getting mad at one of my brothers for making a questionable decision because, chances are, I’ll be making one next.”

The boys have come a long way since they first took over, recognizing the importance of having an experienced team and investing in expertise. “At the scale that the company is now, it can’t just be one person; it needs to be a team effort. Thankfully, the company isn’t relying on three amateurs anymore,” they explain. For the last seven years, they have re-organized and hired industry experts, including a team of illustrators based in Toronto (led by Nick) to keep up with the demanding schedule of a new collection every six months. Never in their wildest dreams did they think that the company would be where it is today. “It’s really exciting and satisfying that here we are 20 years later and it’s working, AND we’re having even more fun than we did at the beginning.”

The company has grown exponentially in those 20 years, remaining true to the values on which it was founded: hard work, quality, and doing the right thing. Even during the hardest times (having to move production overseas, fighting trademark pirates in a Chinese court of law, selling and re-mortgaging their houses), the brothers never compromised on the quality of their brand or their morals. They’ve continued to make ethically-sourced and sustainable items, while maintaining an involved and hands-on approach. Jeremy and Nick even moved to India temporarily to oversee the production factories, observe their daily operations, and get to know the employees. 

“When you visit and meet these people, you see how they’re contributing and realize what you’re responsible for. You can’t help but recognize that you should be doing your part.” Those aren’t just words: the company sponsors an Indian orphanage near the Hatley factory and has so far provided a university education for two of its residents. The brothers chose to add this children’s home to their portfolio of charitable giving because, “it just feels right. We did it because it was the right thing to do.”

It seems the Oldland brothers have built their successful company not only on instinct and hard work, but also with heart. And while they are quick to joke around and have fun, they take their responsibility as employers and citizens of a global community very seriously. When asked about what they are most proud, their newest location at Pierre Elliott Trudeau International Airport quickly comes to mind, but they agree their ability to provide for and help their employees in times of need easily trumps the high-visibility boutique.

What was once a small side business run out of a guesthouse is now a multimillion dollar company with 32 stores worldwide, the result of perseverance and continued professional growth. Throughout it all, Chris, Nick, and Jeremy have stayed true to themselves and to the heart of the brand—learning from their mistakes, trusting one another, and embracing their rebellious and fun-loving nature. “Every mistake is a learning experience. There are still so many more learning experiences; mistakes to be made and fun to be had. We’re not done yet.”