On the TechTO stage ×1
First seen on a TechTO stage in 2025. Every TechTO talk is searchable — ask the archive about Harley ↗
In their words
A lot of people make this terrible mistake with company culture — I swear they do this — they put a picture of an eagle on the wall that says 'leadership' underneath and they're like, that's our company culture. That is not company culture. Company culture is what you do when nobody is watching.
In places like Milan or New York, the posters on the wall are of fashion icons. In places like Texas or Alberta, it's the oil barons. But in Montreal it's Alain Bouchard from Couche-Tard, it's Sam Bronfman, it's Guy Laliberté, it's Aldo Bensadoun, it's Sal Parasuco — it feels like in Montreal we celebrate entrepreneurship in a different way than anywhere else.
Today if you don't succeed, you don't lose your house. You simply lose your 39 bucks. You can try something else. And that makes this time right now, as we sit here, the golden age of entrepreneurship. Full stop.
Around the web ×6
Quick answers
How did Harley Finkelstein end up at Shopify?
He went to Ottawa for law school, met Tobi Lütke there, and has now spent 17 years at Shopify — nearly half his life at 41. After practicing law for about two months, he was COO when Shopify listed on the NYSE in 2015 and is now President; before Shopify his only jobs were a DJ business and selling t-shirts at McGill.
Why does he live in Montreal?
He was born in Montreal, grew up in South Florida, and after 20 years building Shopify from Ottawa, he and his wife weighed Miami, New York, and Montreal — and moved to Montreal two years ago. He argues geography no longer caps ambition (most Shopify merchants have no idea the company is Canadian) and is a regular at Builder Sundays, which drew about 200 devs the Sunday before this talk.
What does he want changed about SR&ED?
Canada gives out $5 billion a year in SR&ED credits, but 80% of applications are filled out by consultants, so 20-30% of the money never reaches entrepreneurs. About ten days before this talk he handed Finance Minister Champagne a memo with wireframes for a 10-minute application with pre-approval — for example, connecting a GitHub account as proof you're doing R&D.