The Exchanges

Q How, how did you develop that skill? What does that look like? Like, how do we make other people world-class or better at storytelling?

A Practice really helps. You know, now I get to do, like, the knowledge projects. It's like, this is a big podcast. I'm not trying to, you know, blow smoke or flatter you, but this is a big podcast. Um, I didn't start by doing the Shane Parrish podcast. I started by doing a lot of tiny little local podcasts and watching them over and over again. You know, I know there's some people that, that hate watching themselves on camera. Uh, maybe this sounds like narcissistic or something, but I, I don't mind. I actually like the, I like watching it because I was able to remove connector words. For example, I say, um, A lot less than most people do, because I've watched myself do it a lot, and I'm like, I'm gonna fix this particular issue. That's the first thing. The second thing is, I think a lot of people end up trying to emulate other speakers. I see a lot of, in tech in particular, there was an era where, like, everyone kind of sounded like Gary Vaynerchuk for a little bit. I know Gary well. He's a friend. I think Gary is an incredible, you know, speaker, and his keynotes are legendary, but that's his style. And then, You see other people that try to do the whole Rogan thing, or the Shane thing, or the Tim Ferriss thing, and, and I don't, I never tried to be somebody else. I wanted to be my, the version of me, which is a little bit excited, not always as perfectly articulate. I speak …

AI assessment note: “I started by doing a lot of tiny little local podcasts and watching them”

Q What does it look like when he reminds you that there's another level for you? Does he just come, he doesn't come to you and say, hey, Harley, there's another level for you. What does he say?

A He's much more German about it. Um, Which is funny because he sort of calls it the German, it's like the German thing for him, but it's actually also like the Jewish mother thing for me, which is, you know, you just got 98% on your exam, you go show your mom, and your mom says, great, what happened to the other two percent? Um, which actually I've now learned it's actually very much a, um, at least the way it's been described to me is that it's actually an immigrant thing, that a lot of immigrant parents are like that. Like, that's great, but like, what happened here? How can you do better? So that's part of it. The other part of it is just that when he gives me A compliment. It is because I went, I went so above and beyond, like, he basically sets a bar for me of what great looks like, and doing my job really well is the expectation. Knocking out of the park, going, like, resetting what corporate storytelling looks like, or how to do, you know, earnings. When you do that exceptionally well, that's when he says, that was a great job. And he is, he's very thoughtful about how he explains, how he gives those, that was really great. He kind of shows you that thing you did that is so far beyond the expectation of, of the industry that you were resetting it. There's this really great thing we talk about, um, which is, it'd be really great, like, I say this, I say this a lot, but I d…

AI assessment note: “he basically sets a bar for me of what great looks like”

Q your selling today. Shopify.com slash knowledge project. Going into all the elements of your life, I know you're very selective about the things that you take on and the things that you do and you say no to a lot. I want to explore that a little bit. What do you want to be world-class at? And so what are the key elements of your life that you're pushing on?

A I am, I'm not a generalist. I've never been a generalist. If you were to ask Lindsay, if you'd ask my wife, um, in fact, if you were to ask my eight-year-old daughter, Bailey, or my six-year-old daughter, Zoe, what our family motto is, they'd all tell you the exact same thing. Uh, it is how you do anything is how you do everything. That is our family motto, which frankly, it means, because they're six and eight, uh, it means it's my family motto, and I've just sort of told them that's their family motto, and they've, they've adopted wholesale. Eventually, they'll be old enough to decide whether it's for them or not, but That motto, certainly for me and Lindsay, my wife, it, it describes our life. There is an intentionality about everything that we do in our lives. The way that I think about, um, leading this incredible company, um, with my team at Shopify, to the way Lindsay thinks about cooking dinner, to, um, the wine that I've been thinking about, you and I are going to drink later tonight. There's a great intentionality about all these things, and, and, I think that makes life fun and interesting. But what I've come to realize, um, this is my 16th year at Shopify. I'm 41, so I've been here for not quite half my life, but almost. Um, the way that I think I had the most amount of value to Shopify is the same thing that I want to be well-classed at, which is I want to be a gre…

AI assessment note: “the thing that I want to be well-classed at, which is I want to be a great storyteller.”

Q I think you're, you're really hard on yourself. What does high agency mean to you?

A I don't think you have to have the glory without the, the high agency, meaning I like people that take deep responsibility for things. This idea, you know, back to expressions that I hate. Well, that's not my job. That is an expression I loathe, especially like in a, in a setting of a company. Um, I, I just, I don't believe that. I don't think that's at any, and frankly, at any stage of company, I mean, there's sometimes where like that literally is someone else's job. I get that, but high agency is someone that sees a problem and says, I'm going to fix it, and then fixes it themselves, that they take, they put themselves into the role of single-threaded owner, responsible person. I take high agency in everything that I have. It's actually a great term. I don't, I shouldn't think about that term that often. I love that term. I think the people I admire most all have high agency. They see something, they, they take responsibility for it, which means that if it goes well, it's up, it's, it's their win. It doesn't go well. It's their loss, but they're able to, they have the levers in their hand. They're able to maneuver those levers and However, they best see fit, and they're willing to accept the consequences of those results.

AI assessment note: “high agency is someone that sees a problem and says, I'm going to fix it”

Q Talk to me about the, the notion of requalifying for your job every year. What does that mean?

A Um, it's sort of, I mean, it's, it's in the sort of same way that like we have this trust battery metaphor that at Shopify, those with autonomy have a very high trust battery, and those that end up having to leave the company, it's because their trust battery is so low that like an old cell phone, it just cannot be recharged. You don't know exactly are you at 46% or 66%, but you know direction where you're at. Um, the same thing exists for this requalification that you can tell when someone, I think you can tell when someone is requalifying for their job. What that means is if you think about the growth of Shopify, which it grows, you know, we've, we're going to log, forget sort of the top line revenue or free cash flow margin growth or anything like that, but just like the growth of Shopify, product areas, GMV, the number of merchants, the geographies, the impact we have on the world, it is growing at this massive pace. I think in order to be on our team, especially to be a leader at Shopify, you have to believe that you have to want to keep getting better, meaning stasis is not acceptable. The thing you did last year may have got you a high five and an attaboy and a pat on the back and, and, and a, and a, whatever. All the great stuff that comes along with that, that is not good enough anymore. And actually at Shopify, I think that's truly, I mean, The source of that energy i…

AI assessment note: “meaning stasis is not acceptable. The thing you did last year... is not good enough anymore.”

Q It's fascinating to me. What do you think the impact will be on Shopify in five years? Like internally, not for your merchants, but like Do you need 10,000 employees? Do you need, like, how does this change the, the dynamic?

A I mean, in terms of the size of company, we, I, I think the size of our company right now and the shape of our company right now is, is, is, is, it's really good. Like, we are very happy with the size. It means we can do more with, with, with the same amount of people. It means we can go into new areas. It means we can build faster. I think not just for Shopify, but I think the companies that are going to be, that are going to embrace it, not utilize it, but truly embrace it and make it part of their daily flow, I mean, look, we talked about schedules and, and, and, and prioritization just before. Once a quarter, when I had time, I go and look through my calendar. I can now create a very simple, like, agentic tool that basically looks at my calendar every week, and on Sunday it says, dude, you got too many social things, or dude, you got too many one-on-one meetings, or like, whatever it is. I can be, all the things that I want to do in my life, I think, can be made better for that. Um, one of my mentors is a guy named Aldo Bensadun. Aldo's 85 years old. Um, he was, um, a Moroccan immigrant to Canada. He built Aldo Shoes. Um, he's, you know, he's, he's built a multi-billion dollar company, and, um, Aldo and I were giving a talk together, um, at, uh, he just gave a bunch of money to McGill to create the, the Benson School of Retail, uh, Faculty of Retail at McGill, which is, uh,…

AI assessment note: “we are very happy with the size. It means we can do more with, with, with the same amount of people.”