The Exchanges

Q So what advice do you have to people who, you know, have a target list of, of, of people who could be role models and mentors and like, like what, what do they need to type in the DM for, for someone like you to open it up and read it and reply?

A I, I, I find for some, um, the DM is really, really challenging sometimes because they have a lot of things coming in and a lot of people coming in, a lot of people messaging them. One, one other way that's super simple is almost everyone you want to meet has some sort of, um, not everyone, but most people will have some sort of philanthropic charity foundation they're connected to that means a lot to them. And if you do research on them, it is very obvious what that is. And if you make a donation, it can be literally 18 dollars, ok? Because I've tried this. 18 dollars, uh, to a, a charity or a foundation that they care about, and you put in the memo, like, I am donating this because I was inspired by this particular thing this particular person did, and I'm doing it in, in, in their honor. Um, and, and then you DM them. Now it's like, now you have two different touch points. Now all of a sudden they're like, I keep seeing this guy's name, like, like, who the fuck is Harley Finkelstein? He gave 18 dollars to this charity I really care about. He sent me a DM. He also bought something from my merch store. He bought, like, three t-shirts and left a really nice comment, a nice review. You can create something that is, number one, very lightweight, very inexpensive, that can give you a ridiculous amount of reach to the people that you want. And then, once you have those relationship…

AI assessment note: “make a donation, it can be literally 18 dollars... and then you DM them”

Q So. If you're not from Montreal, or you're not from Chicago, you're not from LA, you're not from Miami, what, what are some takeaways for people that they could wake up Monday morning and get into that Montreal mentality?

A Okay, so I, I, I, I've been thinking a lot about this because I live in Ottawa. Okay, I've lived in Ottawa now. I moved here in 2005 to go to law school. Uh, that was the year I met Toby, became one of the first merchants on Shopify. Like, that was a, you know, it was, it was important, but I came to Ottawa to go to law school because a mentor of mine Happened to be teaching law at the University of Ottawa in, and he convinced me to go to law school to become a better entrepreneur. I think I've told that story on the show before. Ottawa is not an entrepreneurial city. Ottawa is a government town. One third of, I think it's like 32% to be specific, of the residents in this city work for the government. It's the capital of Canada. So inherently, there is not an entrepreneurial spirit in this city. You don't have the same type of immigrant hustle here you do in Montreal. And that was really challenging for me. And so what we had to do was, because There wasn't organically a tribe around us of other people like us. We had to build our own. And that actually led to, uh, Fresh Founders, which was the group of, of, of a number of us that got together every Friday. And we created a tribe of our own of entrepreneurs in a city that is not inherently entrepreneurial. And funny enough, that, that group that we created ended up building, you know, get around, uh, travel pod, uh, fellow, uh,…

AI assessment note: “There wasn't organically a tribe around us of other people like us. We had to build our own.”

Q Here's, I want to double click into the alpha comment that you made. Here's why non-obvious mentors provide alpha is because they're going to help you create products that go against the grain. And when you go against the grain, that's where the opportunities lie, right? Like if everyone is saying, Hey, go build a startup like XYZ on Twitter, then the moat, you have a smaller moat.

A Yeah. It's, it's, you know, um, after we had our first child, after Bailey was born in. My wife and I would go for these walks every day, newborn baby, like can't do much. Uh, you know, baby's like sleeping or eating most of the time. So we went for these walks around our neighborhood, um, here in Ottawa and Lindsay, my wife had said, Hey, you know, I, I, I would love to go for some great ice cream. There's no ice cream shop. I'm going to create an ice cream company. I'm going to create an ice cream retail shop, uh, called Sunday school. And of course, like, I'm like, you know, I'm, I'm, I'm, I'm the poster child for entrepreneurship. I'm like the physical manifestation of like the entrepreneurial spirit. Uh, at least I hope I am or try to be. And I was like, Lynn's great idea. Let's do that. And she's like, great. Who do I talk to? I was like, I have no idea. I don't know anyone that like, I was like, maybe we can call Ben and Jerry. Like, I think, you know, like I, I, I, maybe they'll take my call. Maybe the ones from my email. Anyways, Lindsay's like, leave it to me. And she went around and she found all these incredible ice cream entrepreneurs and she developed these relationships with them. And Sunday School, like, was rocking. Like, like, the setup, the design, the production, uh, every aspect of Sunday School was like, um, this is like me being very proud of my wife, lik…

AI assessment note: “she found all these incredible ice cream entrepreneurs and she developed these relationships with them”

Q rinse or repeat. You're at the point that if you can use eight to 10 hours in a highly leveraged way in a week, that creates more return than 50 hours of hustle. Strive for those eight to 10 hours to be worth 5000 dollars an hour, and then do all the things with the rest of your time to keep those hours valuable. What do you think about that?

A I think that's great. I mean, I, I think, you know, there's sort of this, this mantra in our, in our world, in the sort of entrepreneurship world, which is, uh, work really, really, really hard. And, and then there's this other mantra, which is like, work really, really, really smart. And I, I think, by the way, I think platitudes are, are a silly way to run your life. But I, I think in particular, those two, like, um, it's a false dichotomy. It's not either you're working hard or working smart. I think there are certain times where you just have to do the work. Um, when I'm preparing for an earnings call, there are, I don't know, 50, 60 metrics that I have to know. I just have to do the work. I have to memorize those metrics. I have to really understand how we did, what the different, you know, factors that led to those, uh, results have been. There's no shortcut for that. In other times, there's a particular goal. I want to get, I don't know, over here, Supreme onto Shopify. And like, that's my goal. And in that, those cases, there's probably a smart way to do it. There's also probably a hard way to do it. And in that case, I find, you know, the smart way is almost always better. So I agree with that. And by the way, you waking up on a Monday, and you're not feeling great, like, that is a very healthy thing. Nobody wakes up every single Monday feeling like they have the world…

AI assessment note: “I think that's great... it's a false dichotomy. It's not either you're working hard”

Q I've got a loaded last question. Where do you think the, the tea space is going? Cause I know you are involved in a tea company and, and next time, well, you're, you can come back on the show anytime you want, but the next time we need to be drinking tea.

A I, I totally, I totally agree. I'm, I'm drinking my fire belly tea right now. I mean, part of the fire belly thing is, uh, this is not me trying to, you know, Promote fire belly, but I've been drinking coffee for most of my life. Um, I've had anxiety most of my life as well. I didn't necessarily recognize that there was a direct relationship between my afternoon coffee consumption and my anxiety levels. And it was only the last couple of years actually through COVID that I discovered it. One of my closest friends is David Siegel, who, uh, famously built, uh, I think probably one of the only billion dollar tea companies ever, David's tea. Uh, they had like 400 locations. He took it public in 2013, I think, um, and so during COVID, I told him that I need to stop drinking coffee because I was just, my anxiety levels were not being helped by it, and he turned me on to green tea, and he curated this amazing green tea for me, like the best green tea on the planet, and so that happens, and then at the same time, uh, the last time I built a store on Shopify was in, like, 2006. It was a t-shirt shop. I was one of the first merchants on Shopify. That's how I met You know, that's how I got introduced to the company. And I want to know what it's like to build a brand new, uh, business and brand in 2022. And so we launched Fire Belly Tea together. And so, uh, we had this great tea company, …

AI assessment note: “this is not me trying to, you know, Promote fire belly, but”

Q reactions to that. Number one, like, I think it's so important that everyone finds their own gentilities. Whatever that is, you know, just a safe spot where they could share stories, share experiences. Um, Harley, I'm curious, like, how, how important do you think that is to some of the entrepreneurs that you see in terms of, you know, having a safe spot? Is that, is that key to success?

A So we're going to jump around timelines a little bit here, but, um, just to connect some dots. So I finished undergrad, finished, uh, university. I actually didn't finish at McGill. I finished at Concordia, which is, uh, sort of, you know, McGill's kind of, uh, younger brother across the street in Montreal. My teacher business had, you know, had some success and McGill did not encourage you to be a full-time, uh, working student. You either went to school or you worked, but doing it together concurrently was sort of frowned upon and they would encourage you to do Uh, a reduced course load. And, you know, I was all of 18 years old or 19 years old, and I didn't want to do that. So there was another university in, in Montreal, which is, you know, not necessarily as prestigious or well-known as McGill, but they, they were totally fine with me being an entrepreneur student. So I transferred and I graduated and a mentor of mine, uh, who'd been a mentor of mine since I was a kid, convinced me to go to law school, um, not to become a lawyer, but to become a better entrepreneur. And this particular mentor, his name is Philip Reimer. Um, He was teaching law that, that year in 2005 at the University of Ottawa. He was effectively taken off some time from his legal practice to teach, which is something that was very meaningful to him. And so he said, why don't you, you know, apply to school…

AI assessment note: “So we're going to jump around timelines a little bit here”