#235 Harley Finkelstein: Why You Must Requalify for Your Role—Every Year

My dad is an immigrant. We're in Montreal, and he immigrated here in the 1950s. His parents were Holocaust survivors. After surviving the concentration camps, they went to Debrecen, Hungary. During the Hungarian Revolution, conditions were dire for everyone, especially Jews. Canada had an amazing program, allowing 40,000 Hungarian immigrants to enter the country during the revolution. Many Hungarians in Canada today arrived in '56 as part of this cohort. They all came by boat, including my dad. When they arrived, they had no money, knew no one, and lacked education.

Around the same time, when I was 13, I was deeply impressed by DJs. As you may recall, I've mentioned that 13-year-old Jewish kids often attend many Bar Mitzvahs every weekend. I found the DJs at these events captivating, almost like magicians. I truly thought they were the coolest people I had ever seen. Although my dad didn't have much money, he always supported my ideas. Whenever I shared an idea with him, he'd say, "Great idea," and then he'd make me business cards, a tangible sign of his support.

There's intentionality in everything we do. I approach leading Shopify with my team with the same intentionality Lindsay uses when cooking dinner, or even when I consider the wine we'll drink tonight. This intentionality makes life fun and interesting. After 16 years at Shopify, I've realized my greatest value comes from being a great storyteller. I want to be world-class at that.

It's especially hard if those things, those elements, give you joy. I don't think you can live without them. If you adopt the philosophy that how you do anything is how you do everything, you must be very careful about your approach. If you aim to do everything well and with intentionality, you simply have to be selective. I don't know anyone who excels at everything. My mentors and role models tend to be "spiky objects." Shopify is a team of spiky objects. We often joke about it being like the Island of Misfit Toys, but what we truly mean is that no consultant would have assembled a team like Shopify's, either in its early days, post-IPO, or even now in 2025.

I value individuals who demonstrate exceptional dedication. This is why I admire entrepreneurs so much; the best entrepreneurs simply out-care others. If you put two people in a room, one operating at 50% capacity and the other at 100%, but the 100% person doesn't care as much as the 50% person, I believe I can help the 50% person develop more skills. However, I'm not sure I can alter their level of ambition. While ambition can be influenced, I think sheer, innate, deep-rooted ambition—call it care or whatever you prefer—is a superpower.

It's really hard. I don't want to create artificial scarcity or pretend our life is different than it is for my kids. Lindsay, a psychotherapist, thinks about this more than I do. She often reminds me it's not what you say, but what you do and what they see. For example, we're fortunate to have help at home, but Bailey makes her bed every day and puts her dishes away. This differs from how Chris Bosh grew up, but we show respect and care for those who help us and are around us.

Ultimately, Shopify's mission is to create more entrepreneurs and make entrepreneurship more accessible. We want more people to use it to achieve their version of success. This could range from becoming the youngest billionaire in the UK, like Ben Francis of Gymshark, to simply affording hockey equipment. We believe entrepreneurship empowers anyone to achieve their goals; it's the great equalizer. The significant unfair advantage large companies have over small ones is headcount. They have many people performing various jobs. While we've made entrepreneurship easier, a resource constraint still exists for a one-person operation, as they lack multiple teams.