Two self-described serial entrepreneurs shared the stories of the many businesses they’ve started over the years, including their current ventures.
They both gleaned inspiration from other influential entrepreneurs in their lives, and they’re proud that Winnipeg is the hub for their thriving businesses.
Yvan Boisjoli, CEO of Peazy, and Chris Schmidt, founder and CEO of Parallel, provided entrepreneurial insights at the last WTC Talks event of 2024. The Nov. 20 networking event, hosted by World Trade Centre Winnipeg and sponsored by BDC, drew a crowd to Torque Brewing.
Boisjoli gained attention by co-founding Bold Innovation Group in 2013, an e-commerce technology company that rapidly ascended to prominence, serving over 90,000 customers. At Bold, he successfully secured $57 million in funding and established a proud Winnipeg-based enterprise. Under visionary leadership, Bold Commerce earned recognition as one of the fastest growing tech companies in Canada by Deloitte.
In recent years, Boisjoli transitioned from his role at Bold Commerce to focus his energy on his latest venture, Peazy. Peazy is a marketplace for mobile service providers that got its roots in Bold, where Boisjoli and fellow founders tried to create a great workplace culture by bringing in service providers like hair stylists, massage therapists, optometrist and more.
“When I left Bold, we built a marketplace for these service providers to exist,” he said.
“It makes it easier for businesses, but also what we discovered is residential towers or senior homes could also leverage that functionality. In the latest little bit, we’ve been pivoting and moving into building a platform for service providers so they can manage their mobile business. There’s nothing like it out there.”
Meanwhile, Schmidt found his entrepreneurial footing as a child when he launched a business to protect Winnipeg trees from Dutch Elm disease. After completing a bachelor of science degree at the University of Manitoba, he founded Geofilter Studio, the world’s first Snapchat filter company. Geofilter Studio experienced a whopping growth rate of 24,000 per cent and expanded to 85 employees within the first year.
In 2017, it was Canada’s fastest growing company and created over 100,000 filters, generating seven billion views worldwide. Then he established Every Studio, which encompassed Geofilter Studio, Every Studio AR and Every Studio Stickers. He sold Every Studio in 2019.
In 2018, Schmidt also founded Pluto Ventures, which is now building a social shopping platform called Parallel.
“It’s the best place to discover fashion, share your style and monetize your looks. We have millions of users across 194 countries in the world,” Schmidt said.
“It’s kind of fun that a team of 15 of us in Osborne Village is building the next big shopping platform.”
Looking back on their roots, both entrepreneurs got their start long before these successful businesses took off.
Schmidt recalls earning money at the tender age of three, alongside his two older brothers.
“My dad would pay us five or 10 cents for every acorn that we would pick up in the yard, and this was a way for him to get a clean yard and a way for me to fight with my brothers over acorns. So I think it was really instilled in us at an early age that, hey, if you work hard, you may be able to make $2 or $3. It was totally not a good sustainable economic model,” he said, eliciting laughter from the crowd.
“Now there’s more zeroes to the numbers, but I think it’s always been instilled in me and my brothers to go and work hard — and if you are lucky, you might find some success.”
When he was 10 years old, he was cutting his neighbour’s lawn and his dad told him to offer his tree-banding services. That was the beginning of his long-standing business called Schmidt Tree Banding, which he operated for 21 years before selling it in June.
Similarly, Boisjoli took the leap to start multiple businesses throughout his life.
“Before Bold, I started nine different companies with my brother. …. Bold was honestly the ninth idea that we worked together on — and it was the most feasible, so we went all in,” he said.
For Boisjoli, inspiration came from his dad, who owned an electrical company and started multiple other businesses.
“I think that by watching others go through it, you build a tolerance for risk. You understand the risk, but you also see how successful it can be,” he said.
“So you get the desire to follow in those footsteps and willing to take that risk to get there.”
Boisjoli and Schmidt also acknowledged the challenges involved with pursuing their business aspirations.
Schmidt noted that Parallel is the final product of seven years of struggle. He started the AI company called Pluto and spent years building a feature to get body dimensions. He used that feature to solve the problem of figuring out what clothing size to buy when online shopping.
“To solve that problem, I actually just made a data set and the data set is Parallel,” he said. “Parallel is a platform where you upload a photo of your outfit and tag the items that you’re wearing — and with that information and your body dimensional data, I can now recommend which pair of socks to buy.”
He overcame the challenge of getting people to sign up for the platform by hosting wine and cheese sessions at their office until they got to 1,000 users. After that, he tasked one of his team members with building a TikTok account that has now garnered more than 300 million views.
“The hardest thing of starting is actually getting someone to sign up — and it’s really, really hard,” he said.
Boisjoli noted that second-time business founders are often more successful than first-time founders because they’re more focused on distribution.
“They understand how they’re going to sell and get in front of their customers. That’s the No. 1 problem. If you’re thinking of starting a company, don’t even think about your product. Think about how you’re going to sell it to the right customer. If you can solve that, the rest should be somewhat easy. Although if you can’t get a product going, welcome to my life,” he said with a laugh. “The distribution is the biggest key.”
For Schmidt and Boisjoli, it’s a point of pride that they established their companies right here in Winnipeg — and they both give back by serving as mentors to others on a similar path.
“Probably the biggest thing I’m proud of is the company that we built in Winnipeg,” Boisjoli said of Bold Commerce. “We had over 350 employees with an amazing culture pre-COVID.”
Schmidt recalled receiving a lead from Disney in his inbox looking for filters for their movies. The Saudi royal family also requested a Snapchat filter for their two-year-old son’s birthday party.
“Our office was on Sergeant and we had 85 Winnipeg people making filters around the world,” he said of Geofilter Studio.
A full crowd at November’s WTC Talks event, at Torque Brewing
And when they reflect on why they changed course to launch new entrepreneurial endeavours, both business owners had a desire to keep moving forward.
“I think you’re not wired to relax. … If I just sat there and did nothing, I don’t know what the point would be,” said Boisjoli, adding that he loves having the opportunity to start again. “I think it’s a certain wiring that you have when you start a company.”
Schmidt estimates that serial entrepreneurs start a new business every decade. For himself, he ruminates on the notion that he’ll only have eight chances to start businesses since he started at age 10 and plans to work until he’s 90.
“I just turned 31 and I’ve done two businesses. Outside of Parallel, I only get another five shots,” he said. “So there’s this mindset as an entrepreneur that it’s not enough time. I get kind of antsy at two in the morning because I’ve only got 59 years to go.”
