Many of the conversations at Web Summit Vancouver this week have been about the technology: artificial intelligence (AI), decentralized social media, and more AI. But Thursday night’s Cansbridge Fellowship event focused on the people behind the tech, the decisions that have shaped their lives and careers, and what others can learn from them.
“If you lean into risk when you’re young … great things can happen in your life.”
Isaac Souweine, Pender
Hosted in partnership with BetaKit and La base entrepreneuriale at McCarthy Tétrault’s Vancouver office, the event brought together a mix of nearly 100 student entrepreneurs and established leaders from across Canada’s tech sector to network and share stories about personal inflection points: when and why they decided to dream bigger and take greater risks.
“These stories consistently highlight that opportunity kind of comes out of nowhere. If you’re just open to it, and you’re bumping into the right people, you never know what can happen,” Cansbridge Fellowship executive director Gabrielle Foss told attendees.
A trio of 2022 Cansbridge Fellows took the stage last night, including Avo co-founder and CEO Anjali Dhaliwal, Slate co-founder Callum Woznow, and Vunatec founder Jesse Pound. They were joined by BetaKit CEO Siri Agrell, Blossom Social co-founder and CEO Maxwell Nicholson, and Pender Ventures partner Isaac Souweine.
The speakers predominantly told tales about why they decided to pivot or get into tech. The decisions were sometimes small, but often very big. Dhaliwal described how finding the strength to ask questions in school was the first in a long line of decisions that led to her shed an introverted nature and speak in front of large crowds. “You just learn to try things, and over time, it works out,” she said.
Pound explained how she decided to move to Kenya to support a startup helping farmers reduce post-harvest food waste, while Woznow recalled the moment he realized the true extent of his personal agency after choosing to intern at a German car company despite COVID-19 restrictions on travel.
“I haven’t looked at the world the same way ever since then,” he said.
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For many of the speakers still early in their careers, these inflection points were recent experiences. For others, they were decisions that helped set a career trajectory they’re still on to this day.
Souweine’s inflection point was a risk he took as a Columbia University student studying Eastern religion and philosophy, when he met a guy building Studentonline.com, a startup that provided web services to small colleges during the end of the dot-com bubble. Souweine joined with a friend to help with sales and marketing, but returned to school after an “absolutely disastrous” summer. But when they found out the firm was raising $4 million from a rich angel, they dropped out and rejoined, telling their parents that “anything could happen.” From there, Studentonline.com lasted nine months. “You can calculate the burn rate,” Souweine joked.
After returning to Columbia to finish his degree, Souweine decided to get a job by selling himself as “a tech guy,” which helped him land a gig as a product manager at Scholastic. That kickstarted a career in Canadian tech that has spanned leadership roles at Frank & Oak, Sonder, Real Ventures, and Pender, which just closed its second fund last fall.
“What is the moral?” Souweine said. “If you lean into risk when you’re young, and you just look up a little bit and get a sense of the way the wind is blowing, and catch that wind and put it in your sails, great things can happen in your life.”
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Nicholson’s inflection point required the courage to sail in a different direction. He told the story of Blossom Social’s pivot from trying to build a social brokerage to creating a social network for investors. The startup’s initial vision was to make a Canadian equivalent of the American investing app Public, and develop an alternative to the likes of Wealthsimple and Questrade in Canada.
The Blossom CEO, who grew up in a small town in British Columbia, told attendees that Blossom was particularly wary of facing off against all of the US startups that had raised more money to build social investing communities.
“I wouldn’t admit it at the time, but we were scared to compete.” Nicholson said, “We were thinking small.”
In 2023, Blossom ultimately chose to abandon its brokerage vision, broaden its market, and move into the US. It was not an easy decision.
“Pivoting fucking sucks,” Nicholson said—but it has already paid dividends. He claimed Blossom now has over 300,000 users—adding 1,000 daily—generated $1.1 million in revenue last year, and is on pace to hit $2.5 million this year. The FinTech company also just recently closed a $3-million financing via crowdfunding from its users and strategic angels.
Nicholson advised attendees to follow in his footsteps and go global. “Don’t be afraid to compete, and don’t be afraid to think big,” he added.
Agrell closed the evening by charting her winding career journey from journalism, to politics, to tech, and back to journalism. She has worked as a Globe and Mail reporter, overseen communications for the Government of Ontario, spearheaded strategic initiatives for the City of Toronto, and led innovation hub OneEleven before becoming CEO of BetaKit last year.
“Looking back now, every turn, every unexpected path, I think, is actually just leading you exactly where you need to go,” Agrell said.
Feature image courtesy Cansbridge Fellowship, by Justin Kung and Matthew Liew.