Shopify President, Harley Finkelstein on What is Being a Good Husband | Full Interview

(beeping) Three, two, one, zero. You have now arrived at your destination. Harley, I'm so excited for this. I cannot believe it's been five years since our last episode, but thank you so much for joining me today.

Oh, it's, it's such an honor and a pleasure to be here, uh, Harry. Five years ago, uh, I, I can't even... I actually... I, I re-listened to our episode from, from five years back, and in some ways everything has changed, and in some ways, um, a lot of things are, are still the same. But, uh, I just wanna say as b- on behalf of an early guest, uh, and a, and, and a active listener, um, what you've built here with the podcast is nothing short of amazing. I think that all of us, um, number one, are, are, are s- we love the show, but we're so proud to see y- how you've built this show over the years. And, and you are a testament to perseverance and how-

Hah.

... just doing the work day after day without... with sort of this relentless pursuit, um, has built one of the best podcasts in the world. It's, it's amazing.

Man, I, I, I so appreciate that. The funny thing for me is you seem to have got younger as I've-

(laughs)

... drastically got older in those five years. I, I, I do wanna start, though, for those that maybe missed the show five years ago when I was a terrible interviewer-

(laughs)

... with a little bit on the context. How did you and Tobi come together, and how did you come to be president of Shopify as you are today?

Yeah. So I, I've been an entrepreneur for most of my life. Um, my, my sort of first foray into entrepreneurship happened when I was a kid. I was 13 years old. Uh, I'm Jewish, and when you're 13 years old and you're Jewish, you end up going to a lot of bar mitzvahs and bat mitzvahs.

(laughs)

And I thought the coolest people in the world, uh, having seen that experience, were the DJs, uh, who were effectively, you know, using, uh, their minds and using, uh, their voice and using their music selection, was effectively able to change the energy of a crowd. Uh, one minute, you know, you have 300 people sitting down eating, like, some rubber chicken dinner at some, you know, hall, uh, and then a minute later everyone's doing the Conga line. And I just thought, "What an amazing m- you know, magic trick." And so I became incredibly enthralled with this idea of, of DJing. And, and so I called around a bunch of DJ companies, and, and of course, uh, I asked if they would hire me, and, and they said no. Uh, I had no DJ experience. I looked like I was a eight-year-old kid, even at 13 years old. Um, so I s- I, I asked my dad what I should do, and he sort of, you know, lightly suggested why don't I start my own DJ company. And the l- the light bulb went off that, hey, this thing called entrepreneurship is not just fun, uh, but it's also a great way to solve problems. The problem at that point was I wanted to be a DJ. But my real entrepreneurial career happened, um, I was... We moved from Canada to South Florida, and then we mo- I moved back to Canada to go to McGill University in 2001. I was 17. And my family lost everything. Uh, my dad was no longer around. And so once again, I sort of pulled out this tool called entrepreneurship out of my tool belt and started selling T-shirts to local universities in Montreal and then the rest of Canada. A mentor of mine by the end of my undergrad had convinced me that my T-shirt business was, uh, well, it was cute, and, and you know, it allowed me to pay the bills and support my mom and sisters, but it was not a real business. Uh, it had no advent- c- advantage, it had no moat around the business. And so that mentor, uh, convinced me to consider law school, uh, not to become a lawyer but to become a better entrepreneur.