Shopify president calls Montréal “the most entrepreneurial city on the planet” at North Star event

Amiral Ventures partner Nectarios Economakis (L) and Shopify president Harley Finkelstein (R).
Event panel included insights from Stay22, Dialogue, Nesto, and PemPem founders.

At HEC Montréal, just across the street from Shopify’s office, more than 300 members of the local tech ecosystem gathered to glean insights from different stages of the entrepreneurial journey. 


“You’re all in, but you’re planning on a marathon, not a sprint. And so that means you’ve got to take care of yourself and the people around you.”

Joann de Zegher
PemPem

The first edition of North Star, a new Montréal-based event series, was jointly organized by Nectarios Economakis, partner at Amiral Ventures, Gabriel Sundaram, co-founder of Attain, and Éléonore Jarry, partner at Brightspark Ventures, with collaboration from student teams at McGill Ventures and HEC Montréal’s La base entrepreneuriale. 

The evening kicked off with a panel of student founders running early-stage ventures, followed by a roundtable of established CEOs providing career insights. It ended with a fireside chat between Economakis and Shopify president Harley Finkelstein.

The audience was filled with nearly 60 percent founders and startup team members, according to the North Star organizers, representing 97 startups. Supporting partners included Startupfest and Stay22, a travel tech startup run by panellist Andrew Lockhead. Stay22’s head of product, Laura Di Constanzo, also unveiled the Montréal Startup Guide, a new website that centralizes Montréal startup community events and resources. 

The founder panel, moderated by Sundaram, included Stay22 founder and CEO Andrew Lockhead, Coral co-founder and former Dialogue CPO Anna Chif, Nesto co-founder and CEO Malik Yacoubi, and PemPem founder and CEO Joann de Zegher. 

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On stage, they highlighted different approaches to success—knowing when to pivot, Lockhead said, was a key skill he learned when the COVID-19 pandemic hit and Stay22’s revenue dropped by 90 percent. Another skill, according to Chif and Yacoubi, was obsessing over the right details.

“At Dialogue, we became the largest telemedicine company in Canada,” Chif said. “And I think part of it was because we were obsessed with the user experience.”

In response to an audience question about balancing obsession with mental health, de Zegher said to surround oneself with co-workers who will break up the grind.

“You’re all in, but you’re planning on a marathon, not a sprint,” de Zegher said. “And so that means you’ve got to take care of yourself and the people around you.”

From L to R: Attain co-founder Gabriel Sundaram, Stay22 CEO Andrew Lockhead, Dialogue co-founder Anna Chif, Nesto CEO Malik Yacoubi, and PemPem CEO Joann de Zegher. Image courtesy Eva Blue Photography.

The student panel made it clear that passion, and obsession, were in no short supply in Montréal tech. Two out of four student panellists were transforming lab-created ideas into ventures—Dr. Roseline Olory, founder and CEO of BrainInnov, is developing an early screening tool for lung cancer, while Le Thuy Duong Nguyen, founder and CEO of unbIAsed.Rx, is building a platform to identify biases in drug prescriptions. They both raised the challenges of pivoting from research to a business mindset, especially for women in male-dominated fields.

Anthony Azrak, co-founder of artificial intelligence (AI) software-as-a-service (SaaS) platform OpenSesame, called out the low levels of capital circulating in the province and blamed it on university policies making it difficult for students to start ventures.

“At [the University of] Waterloo, you can take a semester off to start a business,” Azrak said. “Why can’t we do that in Québec?”

Azrak and Woo Park, operations lead at NationGraph, admitted they were both leaving Montréal to continue working at their respective startups. 

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In a fireside chat, Shopify president Harley Finkelstein presented himself as Montréal tech’s cheerleader, calling it “the most entrepreneurial city in the world.” He encouraged the audience to build in Canada, and create a country of “HQs” and “acquirers, not acquirees.” 

He referenced his previous comment from Elevate Fest in October, where he called Canada’s lack of ambition the 600-pound beaver in the room. At North Star, he acknowledged some of the backlash his comments roused at the time, including that structural barriers were disincentivizing entrepreneurship in Canada. 

“I’m not saying that it’s the most perfect environment for entrepreneurs in Canada,” Finkelstein said. “What I’m saying is, who fucking cares?”

The sentiment matched Finkelstein’s appearance on The BetaKit Podcast last September, when he encouraged entrepreneurs to build companies with a global mindset without using Canadian identity as an excuse for poor performance. 

Some younger founders BetaKit spoke with after the event said that though they appreciated Finkelstein’s insistence that most successful people have pasts “littered with failure,” they wished they had a better picture of what failure looks like.

Unfortunately, no time was allotted for audience questions and Finkelstein did not make himself available to the media.

Feature image courtesy Eva Blue Photography.

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