"The transition from 'I need to pretend like I know everything, because that is what's required of me as an entrepreneur' to 'I actually know very little' is an opening. That is the introduction to having a growth mindset, where you feel like you are constantly a work in progress."

In this episode

In our 50th episode of Supermanagers, Harley Finkelstein shares how he builds highly effective teams.

Harley began his first company selling and designing t-shirts when he was just 17 years old. He pursued his law career and worked at a Toronto law firm before deciding to pursue his passion for entrepreneurship. Today, Harley is the President of Shopify.

In this episode, Harley shares how vulnerability is a superpower and also talks about self-awareness and delegation. 

Harley also discusses how he leaves breadcrumbs while recruiting and why you always need to be on the search for great leaders.

Tune in to our 50th episode to hear from Harley Finkelstein!

Like this episode? Be sure to leave a ⭐️⭐️⭐️⭐️⭐️ review and share the podcast with your colleagues.


Is entrepreneurship and leadership the same?


Vulnerability as a superpower


Life before Shopify


Self-awareness and ego


Getting comfortable with delegation


Hiring isn’t transactional


Leaving breadcrumbs in your industry


Extending the hiring process


Your career can be a jungle gym


Learning from leaders across industries



Aydin Mirzaee (  00:14

Harley, Welcome to the show.

Harley Finkelstein (Shopify)  00:21

Hey, Aydin, thanks for having me. It’s a great privilege to be on the show.

Aydin Mirzaee (  02:50

Yeah, I’m super excited to do this. I mean, for longtime listeners and viewers. They know we’ve been working on this podcast for a while. So to have you as the guest for Episode 50. After a year of doing this is quite the honor. Wow. 50. That’s

Harley Finkelstein (Shopify)  03:04

amazing. Congratulations. It’s really cool.

Aydin Mirzaee (  03:06

Yeah, thank you. And I know we’re not too far away that you know, physical distance wise geographically,

Harley Finkelstein (Shopify)  03:11

you’re like around the corner from me, but but you might as well have been on the other side of the world, considering we can’t see each other.

Aydin Mirzaee (  03:17

Yeah, but this works as well. I feel like the video setup and you know, just like the recording setup almost makes it easier to do it remote.Even if you are in the same city, 

Harley Finkelstein (Shopify)  03:25

it’s actually quite amazing. In 2019, I spent about 95 or 96 nights. I think actually, I calculated this a little while ago, I think it was like 96 nights in a hotel, just traveling for work. And obviously in 2020, I think I spent like three nights because COVID hit in March. And one of the amazing things is that because the world has moved to fully digital, I realize how much more effective and productive I can be. If everyone just accepts video as being the default way to communicate. I used to go to Silicon Valley to have a one hour meeting. I mean, that’s a three day trip, give or take, you know with travel time and transfers of planes and, you know, trying to make the trip worthwhile for really a one hour meeting. Whereas now I can, you know, I can do it over lunch. It’s really amazing that we’ve all moved to this and embraced this so much.

Aydin Mirzaee (  04:16

Yeah, you guys famously went all remote. And I’m gonna ask you a lot about that and leadership while remote too. But I just wanted to kick things off. I think a lot of people have heard about your background. But obviously when you were 13, you were DJing special events and bar mitzvahs at 17. You started a T shirt company while attending McGill. You figured out that competitive advantage with your T shirt business would be tough. So you got into law school and did an MBA. And I think like that’s when you and I originally met, but you only practice law for a year, then by 10 months. So yeah, we don’t want to over estimate that. And then obviously the rest is history. You’re now president of Shopify and It’s one of the largest tech companies in the world. You know, the interesting thing about Shopify and yourself, I feel like every time I think about you or Shopify, it’s always about entrepreneurship, promoting entrepreneurship. And that’s really what the company is about. It’s like the entrepreneur company, one of the things I wanted to ask you about was, you know, just talking about leadership, and you know, how much you think leadership is part of the whole entrepreneurship story. I have it that you were actually class president growing up, is that true? 

Harley Finkelstein (Shopify)  05:31

It’s true. Yeah, I was. I was born in Montreal, I moved to South Florida when I was, but 12 or 13 years old, and went to this very large, pretty typical US public high school with three or 4000 kids. And, you know, I was a short Jewish kid, I couldn’t play basketball or play football. And I realized, actually, that that was sort of, for a lot of people in high school, the way that they found their identity was really through their extracurriculars. Whether it was sports, or drama, or debate, or whatever it was, I was just drawn to student politics. I like the idea of mitten, you know, maybe this sort of leads the entrepreneurship conversation, but I like the idea of advocating for people that may have otherwise not been able to advocate for themselves. I like the idea of leveling the playing field in a way that was effective and valuable for others. And so you know, whether it was getting our lunch hour extended by 10 minutes, because I recognize that there wasn’t enough time to get after the lunch Bell went off to get to your next class. And so many students were getting these detentions because they were late for class, because the commute time is a big High School and huge high school. It was enough. I always liked the idea of advocating for those that may have not been able to advocate for themselves. I am fairly assertive, fairly aggressive, incredibly extroverted, you know, Tim Ferriss refers to me as, as a power expert, which I think is accurate.

Aydin Mirzaee (  06:53

That’s awesome. And so can you be an entrepreneur without also being a leader? Like how much do these two things go hand in hand, I don’t think you need to be a particularly good leader to be an entrepreneur. I mean, if you go down to sort of the very basic building blocks of entrepreneurship, I think an entrepreneur is someone who sees an opportunity and, and fills that gap and decides to do something about it. And I know plenty of entrepreneurs who are sole proprietors, who are independent, you know, one man, one woman shops who don’t necessarily need to need to be a leader, I think the decision is around, am I a leader? Can I become a good leader that only comes about when scale becomes a factor? And so I think, in order for you to build a highly effective team that has scale, I think you need to be a great leader. And the funny part is, no one is born a good leader or a good manager, and that that is not inherent, you may have inherent leadership qualities. There’s, you know, there were those kids that in summer camp who no matter what crazy stuff they were doing, every other kid seemed to follow them. there obviously were people that had innate leadership qualities to them, but I don’t think that made them a really good leader. And but when you sort of zoom out, and you look at some of the most impactful companies, or some of the most impactful entrepreneurs, most of them, if not all of them have had to transition from tinkerer, maker builder to leader manager. And I think that’s the reason why at some point in all of our entrepreneurial journeys, you make the decision. Do I want to keep building? Or do I want to lead and help others build? And certainly for me, I didn’t realize how much I would love the leadership side of entrepreneurship, because for so long, I was just a one man marching band printing t shirts, selling t shirts, cleaning, you know, DJing carrying equipment selling DJ contracts. Yeah, that’s awesome. And so you know, you are talking about leadership qualities, and I’m like developing some of these over the course of time. So I had reached out to someone that you know, really well, Brennan, who I think just actually celebrated his 10 year anniversary, just celebrated his 10 year anniversary, and Brendan’s only, like 22 years old. So he started I’m just joking, it gets dirty. But Brennan was Shopify, Brandon Lowe and Daniel Beauchamp were really shocked by his first interns, in 2010. They kind of rented some co-working space for us. And, and and Daniel ended up building our entire AR VR practice and team at Shopify. And Brennan was sort of the first business developer at Shopify, and was sort of my protege for a long time. Yeah. And so it’s interesting. So I reached out to him, and my question was, you know, what kind of questions should I ask Harley? And one of the things that he mentioned was, I don’t know how he does it, but Harley’s turned vulnerability into a superpower. And I’m curious, what is that? What does that even mean to turn vulnerability into a superpower. A lot of people that self identify as Entrepreneurs are someone who identifies as sort of a founder, we tend to put on a bit of a facade. Sometimes the facade is out of necessity, because, you know, I remember selling my first t-shirt contract at McGill in 2001, I walked into that procurement meeting, as if I had the largest t-shirt company in the world. You know, the, the, you know, fake it till you make it phrases is is is certainly relevant in those days, eventually, you get to a point where you almost have to swap, as opposed to acting as if you have all the answers, because that’s what the client is buying, acting as if you have this inherent confidence that you know how to make great decisions. At some point. I think we all at least, those that really care about personal growth, that care about having a growth mindset that are playing the infinite game, as opposed to finite games, you begin to realize there’s a lot I don’t know. And that transition from I need to pretend like I know everything, because that is what’s required of me as a, as an entrepreneur to actually know very little, that a lot that that is an opening, that is a that is the introduction to having a growth mindset where you feel like you are constantly a work in progress. And I think what Brendon is alluding to is nearly as a Shopify, I don’t think I was especially self aware, I don’t think I was especially not that I didn’t have a growth mindset. But if you said to me, Hey, I need you to do this task, I would just kind of figure it out. Whereas now I think I’m a bit more thoughtful about Alright, well, who’s the best person around to do this task? What can I learn from them? How can I take some of their experience and add it to my Rolodex of my skill set. And the cool part about that idea of vulnerability, and Rene brown talks a ton about this. And so I’m sure I’m stealing a lot of her lessons. But the cool part of vulnerability is, as you progress in your career, as you progress in your business grows, the more vulnerability you show, you actually show more strength than you do weakness. And there’s a really interesting effect called the Dunning Kruger effect. Are you familiar with that? Yeah. But I’d love for you to explain it.

Harley Finkelstein (Shopify)  12:26

So during Dunning Kruger, two professors from Columbia University in Harlem in New York City, effectively talk about that, when you don’t know a lot about a particular topic, you don’t know enough to know you don’t know a lot. So you have a certain naivete about it, a sort of ignorance about it, which almost makes it seem like you know everything. It’s sort of like, you know, ignorance is bliss. The CounterPoint or the opposite of that is, as you begin to explore your field, your profession, your craft, at a much deeper way, with far more intention, you begin to realize, holy shit, I don’t know very much at all. And there’s two ways to look at that. One way is to say, I’m, I’m scared, like, I don’t know a lot like, what is this gonna lead to? Am I gonna get fired, in my mind completely unqualified. But another way to think about that is, I have so much to learn what an amazing opportunity I have right now to go deeper to get better. And at Shopify, we talk a lot about this idea that we are leaders, and we want all of our leaders at Shopify really to think about doubling down on their strengths as opposed to mitigating your weaknesses. I think in most companies, Shopify is currently from a market cap perspective, the largest company in Canada, we’re one of the largest companies in the tech industry in the world, which is unbelievable to even say aloud, and I’m sure it sounds crazy for you to hear, because you’ve been such a big part of the Shopify story, Hayden from day one. I mean, you introduced me to Toby, back in the day, it’s unbelievable. But one of the things about most big companies is they tend to want their leaders to be these well rounded objects, where they’re not spiky, but they actually, you know, they know enough about everything. And at Shopify, we’ve taken a different approach, which is that if you’re really good at this one thing, we want you to become the best in the world, that that one thing, and we will help you bring on people to mitigate and to, you know, fill those weaknesses. And so back to your vulnerability, one thing that that I’ve embraced, in the last, I don’t know, six or seven years or so, I’m going I’m going into my 12th year at Shopify, which is like a third of my life, but one of the things that happen, progress, you know, 2013 2014 or so is that I began to realize that Shopify is not only my life’s work, it’s not only the thing that like the Venn diagram with my personal ambition and my professional ambition are almost the same, which is entrepreneurship create more entrepreneurs support more entrepreneurs help help entrepreneurs scale level the playing field so more people can access entrepreneurship. But I also recognize that Shopify may be the greatest place in the world for me, not for everyone, but for Harley, to grow, to learn to develop. And I like to say that at Shopify, every single year, I work at Shopify, it feels like I’m getting 10 years worth of career development, which is amazing. The prerequisite to that, however, is that I have to show vulnerability. I have to be open to this if there’s all a bunch of stuff that I don’t really know about, I need some help. I need to hire people better, smarter and faster than me. And I need to listen to them. And that has been incredibly valuable. And I hope Brennan, who prompted this question, is kind of him to recognize that because something I don’t really talk about very often, but I think he’s on the same thing.

Aydin Mirzaee (  15:46

Yeah, that’s amazing. And I think like, these are me, it’s very interesting to hear your perspective on this. And as a development leader, leading a big company like Shopify, I did want to take some time, though, and rewind a little bit and go to the earlier version of yourself. And when you were first starting out your management career, you know, starting off, have you ever had a real manager or someone that you reported to outside of like the context of Toby in Shopify? Has there been ever anyone? Or has it always been you the entrepreneur,

Harley Finkelstein (Shopify)  16:19

I guess the only sort of job I’d ever had other than Shopify was as a lawyer, I worked in a law firm, I worked at a midsize firm in downtown, excuse me in Midtown Toronto. And it was a corporate finance firm. So it was mostly, you know, commercial law, which is like banking and real estate stuff. There were some m&a work as well. I did a bit of litigation. So sort of 10 months, five months was in sort of corporate commercial, five months was in litigation. So I went to coordinate arguments on behalf of clients, which was very valuable. I had a couple. So I had senior lawyers and supervise me in total candor. They were terrible managers. They were terrible leaders. They were uninspiring, they didn’t teach at all, they did not look at them, they did not view. And I’m sure that’s changed. And maybe that’s just unique to me, I don’t think it is, I think this is fairly common in a lot of service based professions, particularly in places like law firms, where the unit of productivity is time based, it’s an hourly rate. So the more hours I work, the more they can build clients, which is good for the firm and increases their profitability of the year. So there was no interest, there was no appetite, to teach me how to do things better and more effectively. In fact, the more time I spent, the better it was for the firm. And, in fact, my articles during my 10 months working as a lawyer were so bad. I’ve talked about this before, but maybe not as, as with as much bigger or as much enthusiasm or assertiveness, as I’m using now. But it might tell us as a lawyer we were so bad, that it pushed me right back to entrepreneurship. And in fact, it pushed me to call Toby and say, I was one of the first merchants on Shopify. I know what Shopify did for me. I want to offer that to others. And, and the end result is, you know, I left law as fast as I as I could and moved to Ottawa in early 2010. To go work for Toby.

Aydin Mirzaee (  18:21

Yeah. And so when you first started, I guess, you know, Shopify, obviously has been growing very fast. Since the very early days, as you started to become a manager there and the leader there, what would you say were some early lessons or some early mistakes that you made in those beginning years?

Harley Finkelstein (Shopify)  18:38

Part of it was going back to that lack of self awareness or ego I suppose I started at Shopify in my 20s. I didn’t have a good enough sense of self. I didn’t have a good gauge of, of who I was. I think that led to me making some really poor hiring decisions. I think I was scared to hire people better than I was, I think I was scared to hire people that were more experienced. And I was, I was trying to figure out what my place was there. And frankly, Ireland is a Shopify. We were just a handful of people. I was one of the only non engineers at the company. My job was to be a Swiss Army knife, who was what Daniel and Cody and Toby did not want to do? I’ll do that stuff. What are they, you know, not not enjoying or not like or maybe the stuff they’re not good at? I’ll take that stuff on. So I think one of the things was that that was one major mistake that I did. The second mistake I made was I didn’t actually seek out really good managers elsewhere outside the company. I had mentors. I’ve always had mentors throughout my life and mentorship is something that I still believe in. I am now trying to mentor more people and pay forward because people were so valuable, and so frankly, generous with their time. You know, you’ve heard me talk with Phil Reimer for example, or, or people like that, that have just given me a lot. But I had this amazing board of directors. I mean, Bessemer was on our board first Mark was on our board, john Phillips on our right this amazing Board of Directors, I could have easily approached them and asked them a very simple question which was Who are the best leaders who were the best managers that you know, and I could have easily made those phone calls and pick the brains and, and, and created a bit of a curriculum or a lesson plan for my own my own scaling of being a leader. I didn’t do that in the early days, that was a big mistake. Probably the third biggest mistake that I made in the early days as a leader was I didn’t really know how to do one on ones very well. In fact, I think, you know, this may be slightly revisionist history, but I think I viewed it one on one. With the people that reported to me in the early days, probably including Brennan as my one on one where I got a chance to tell him what to do. That’s not what a one a one, a one a one is, first off sacred. I may miss a couple meetings, you know, in a given week, that’s really, really busy. But the one meeting the meetings that I never, ever miss are my one on ones with my, with the people that report to me, because I think they’re sacred important, but they’re not my one on ones, it they’re their one on ones, it is their opportunity to come to me to ask for help to get guidance to update me on something. And I didn’t really appreciate the dynamic of the one on one. And today. I think I do a lot more.

Aydin Mirzaee (  21:08

Yeah, that I mean, those are, those are three incredible lessons. And I think, you know, one of one of the things that you referenced there in terms of, you know, hiring great people, I think that, you know, when you do hire really great people and people who are smarter and better at a particular function, I think one of the things such as delegation starts to become easier, because obviously, why wouldn’t you delegate, you know, this person is so much better than you somehow this concept of delegation is hard. You know, for first time managers, one of the things that I recall, you and I talking about, you know, at some point, I think it was like the early days of the build a business competition, obviously, like the first year, you guys invented this ran it, and then every year it came bigger and more exciting with and it just like almost became grew to the point where you’re like, how much bigger can this thing get? But one of the things I recall you telling me was, as a company started growing, was that you kind of missed this concept of like, being there and running the build a business competition. And I just feel like this is one of the things that, you know, I certainly also have difficulty with so how do you get comfortable with this concept of delegation and, and not like being intimately involved with all the details of your operation as it starts to scale.

Harley Finkelstein (Shopify)  22:26

So I think delegation is difficult, especially for founders and entrepreneurs, because it’s so deeply tied into the, the spirit of entrepreneurship, which was in the early days of any company, any business, you gotta do everything, you have to be the janitor, and the CEO, you have to be the receptionist and the head of production, you have to be the head of customer service, but also the head of technology. And when you start lots of companies, successful or not, since you’re a kid, 13 years old, for me, and I know, you’ve been starting companies, since you were a kid. Also, it’s just it becomes part of your condition, which is that you begin not to need to rely on anybody that is a, that is a mechanism that entrepreneurs build into their firmware, because they know that it’s better not to rely on anyone, it’s better just to be able to do everything yourself. And I think actually, it’s very valuable, like I knew, you know, I still know more about how to make a T shirt, whether it’s the rib or the GSM count, or how to do a cut and sew on a big piece of fabric and most t shirt brand owners, because when I was doing my T shirt brand, I could not afford to hire a head of manufacturing or screen printer or anyone on the production side. So I did everything myself. Now that made me also more valuable, you know, head of sales for my own company, because when some random person asked a question in a sales meeting, I knew everything there was whereas the other person that was pitching from another company, you know, coming from like, Russell athletics or gildan had no idea because they were just a sales rep, some other team handled production. So I think this idea of doing everything yourself is baked into the entrepreneurial condition. Eventually though, you realize that you can do a lot more, you can be a lot more effective, you can add a lot more value and impact if you start delegating specifically, if you’re delegating to people who are better at the task than you are, and then eventually the pendulum swings from do everything yourself to delegate everything. And you get to that delegate everything and you start feeling some sort of longing for your craft. And for me, that’s, you know, making deals. That’s storytelling. That is sort of the sales and marketing aspect of our business for Toby, of course, its product and writing code. And so I think I swing the pendulum way too far the other way. And so what I realize is there is some beautiful balance in this pendulum of do everything yourself and delegate everything. And for me, that means sometimes when I can be really effective, and I see there’s an opportunity for me to get my hands dirty and go really deep into something, I will do it. So if you want to build a business, you’re to build the best year ever Myself, then eventually, we had a marketing team, we had a CMO, we had, you know, all types of partnerships, people, and they got totally involved. And it was a really good result that there were parts that I missed. And I think that they were, in some cases, doing the same thing that I had originally architected at scale. And I wanted them to rethink everything. And so I got back involved. And so the balance that I think that I now have, if you can call it balance, is that right before this call, I was talking to a merchant, one of the largest brands direct to consumer brands on the planet, who is not on Shopify. But the idea, the objective is that the team was struggling to migrate them over from the enterprise platform, the CEO of the company, I have met a couple of times. And when I sort of was looking at the sales channel in Slack, and I saw they were struggling with that, I said, hey, look, I have some time today. Let me let me give the CEO a call. And so that gave me great energy. Now if I spent all of my time selling big brands, I would not be able to do the rest of my job. But if I never was able to get a chance to sell bigger brands on Shopify, one shop, I wouldn’t, may not get that brand on. And two, I wouldn’t be having as much fun. You know, we don’t really talk about this idea of fun very much, because specifically, when you’re, you know, you’re building this company fellow from scratch, and I’m operating Shopify at this incredible scale. We don’t often say, you know, we don’t often ask each other, Hey, are you having fun when you and I hang out, you know, in a pre COVID world a lot, and we talk about our businesses, we talk about our families and what we’re going through, and our kids are friends or wives or friends, we always talk about the stuff in our life. But I don’t think I’ve ever asked you or you’ve ever asked me Hey, are you having fun. And if you want to use a long term horizon of a role, a career being an if I want to be at Shopify, the rest of my life, I want Shopify to be the last job I’ve ever had, whenever that ends, you know, I hope it doesn’t end anytime soon. But when that ends, I’m not likely not going to have another job after this, I’ll do cool stuff. But a job like Shopify, I just can’t imagine doing something like this again, and most most of it is shop like is, it feels like Shopify is the company that I would have, you know, I would have created for myself as a job because it’s just, it’s perfectly matched to my my passion, my level, my my craft. But that being said, if you delegate everything, there are some things you miss. And I think it is possible, stop having fun. And so allow yourself to bring in some of those things, whether it’s one sales call a week, or it’s a couple product reviews, or writing some code, you know, once a quarter during hack days, I think that’s important.

Aydin Mirzaee (  27:30

[AD BREAK BEGINS] Hey, there before moving to the next part of the interview, quick introduction to tell you about one of the internet’s best kept secrets, the manager TLDR newsletter. So every two weeks, we read the best content out there, the greatest articles, the advice, the case studies, whatever the latest and greatest is, we summarize it, and we send it to your inbox, we know you don’t have the time to read everything. But because we’re doing the work, we’ll summarize it and send it to your inbox once every two weeks. And the best news is completely free. So go on over to fellow dot app slash newsletter, and sign up today. And with that said, let’s go back to the interview. [AD BREAK ENDS] Yeah, I love that you said that because I feel like the obvious, or like, the easy answer is, well, of course, if you want a skill, then you delegate and that’s how it works. And it’s true that like most things in business and leadership are always nuanced. It’s never, you know, one way or the other. And I love the pendulum analogy. And I love that it can swing from one direction to another, you zoom out, you zoom in, and ultimately have fun. I think that is a very good point. It’s so important to have fun. Yeah, if you want to do something for a long period of time, you can’t not have fun. But speaking about delegation and scale, you know, obviously, one of the unique vantage points that you have is just you’ve seen hiring literally like you probably interviewed hundreds, if not 1000s of people. And so when you interview that many people, one of the things that you presumably get good at especially as your company continues to succeed is identifying trends and patterns. And so what have you noticed in commonalities for some for the hires that you think that you’ve done the best set like, what have you learned in hiring during this period of time?

Harley Finkelstein (Shopify)  29:23

I think that a lot of companies look at hiring as being very transactional. you post a job description, someone applies or a few people apply. You look at those applications. You cut them down from 30 to 10. to three, you do interviews, you bring on other people to interview them as well. You make a hire, you give a Give, give a contract, they sign they come work for you.

Aydin Mirzaee (  29:45

Yeah, it’s very regimented in that way,

Harley Finkelstein (Shopify)  29:47

that’s not how at least the people that are closest to me, the people that I work with on a daily basis. That’s just not how it happens. I won’t say who this is because he won’t like it but there was someone that led him major, major part of our business for me now, and he was living in a US city working in a great company and had no intention of leaving. And almost on a, you know, every six months or so, I would make up some excuse for why I was in that city just to have breakfast with this person. And I’d call him and I would say, Hey, I’m in town, when I have breakfast. And every time we just chat, you know, I had hurt myself actually, I had heard about him from a journalist. And that’s sort of how it all is, that’s how I sort of connected with him and said, Oh, I heard about you, and, and you’ve done some cool things here. And then I think after probably the third breakfast we had at the end of that I was like, hey, just you know, I mean, this isn’t, you know, this isn’t a pitch or anything like that. But if you were ever to consider leaving your current job, we would love to have you at Shopify, we would we’d build a great team around you, we would give you a big, you know, big piece of the business, you’d have incredible mandate, you’d have autonomy, you can do everything that you do currently. And I think with a lot more upside, a lot more opportunity. He said, Sorry, I’m happy. I’m investing a great gig big job, you know, all the great things my family’s very happy living in United States, and it was only, you know, probably, you know, four months after that final breakfast that he called and said, I’m ready to talk, whatever you want to call that I sort of refer to as breadcrumbing. But like, I try to leave a lot of breadcrumbs around my industry, around the technology industry around the commerce industry. So that if someone is in one of these companies, big company or small company, and they’re getting, you know, the feeling a bit of an itch, maybe they’re contemplating, you know, what else is out there? They’re always thinking, well, I can always call Harley, I can always talk to Toby or Shopify, that’s always an opportunity. For me, that makes it far more long term. It’s not something you’ll do if you need to hire tomorrow, when you do that at scale over a long period of time, it really works out. I mean, it’s just like that in so many ways. You’re always recruiting, you’re always leaving breadcrumbs are always hinting at someone Hey, like, if you were to leave that thing, like there’s this really cool thing in Shopify that I think you would just do great at, you’d love it, you’d be able to build something from scratch. And I do that probably, I don’t know, 10% 15% of my time right now is spent on just that random stuff. A lot of times, you know, I all have, you know, zoom meetings with people just to check in on them. I heard they had a baby, or I heard they’re working on something new, or they went on this really cool ski trip. And I just kind of say, Tell me about the ski trip and leave a little hint at the end of the meeting and at the end of the call and say, Hey, just you know, there’s this really neat thing we’re working on. What do you think? I think that is a much less transactional, far more long term way to look at recruiting, I think that actually has a much higher, much higher return on investment.

Aydin Mirzaee (  32:36

Yeah, I love that. I mean, this concept of always being recruiting but it’s almost like, because you are so committed to the long term vision and you’re playing that long game that it almost makes sense. It’s not about, you know, who am I going to hire in the next month? It’s, you know, over the course of the next decade, who are the people that you know, might be involved in the company and just optimizing for that? 

Harley Finkelstein (Shopify)  32:58

How do you hire people that are effectively unhireable? You extend the process of engagement, you extend the dating process, that’s how you hire people that are effectively unhireable. And by the way, people that are quote, unquote, on hireable, they’re usually also very, very well paid. And so a financial incentive isn’t always going to be the trick to get them to come over. But you are showing this very long term, multi year interest in them. It’s not, it’s not a sure thing, they’re gonna come to you. But it may be the difference of like, wow, this company, these people, this person, really, really wants me to come work with them. Like, maybe I should talk to them about this.

Aydin Mirzaee (  33:39

Yeah, I love that. So I guess on a similar note, we’ve talked about hiring one of the things that, you know, I’ve been very curious about was a very unique characteristic of just like the team at Shopify. You know, we talked about Brennan earlier, and how he celebrated his 10 year work anniversary there. And you just talked about getting there. You know, you’re 12. And but that’s not an uncommon thing, like many people like Shopify is their first and only job. And many people have stayed there for like insanely long periods of time. You know, in a world where now it’s common for people to stay at a company for a year or just over. You guys have just demonstrated this crazy longevity. And I’m curious, how do you do it?

Harley Finkelstein (Shopify)  34:27

Lindsay Craig, who leads brand at Shopify, who leads one of our teams, wrote this great blog post about this idea of the career path not being a ladder, but being more sort of like snakes and ladders like, I think she calls it a jungle gym. That’s a big part of the culture at Shopify. Shopify is a place where your path inside of Shopify, whether it’s five years or 50 years, may not look like a traditional path. We have people that have led teams of 50 or 100 or 500 people who decide at some point They just want to be an individual contributor. And that’s okay. Or someone who is a salesperson, an amazing Rainmaker type salesperson, who decides they want to learn how to code and go be, you know, a junior developer or an apprentice Product Manager. That idea that at Shopify, it is okay to look at your career like a jungle gym, as opposed to a ladder has to go up, where there could be lateral moves, some moves may even seem from the outside world to be a demotion, even though it’s not we make it really okay to do stuff like that. And, you know, Brennan right now is working in marketing and marketing brand partnerships. But a year ago, he was leading one of our European International Business teams, and before that he was focused on sort of the ecosystem of Shopify. That I think is a big part of it. That’s the first thing. The second thing is because Shopify continues to evolve. I mean, you know, 10 years ago, if you would have asked what Shopify is, I would have said, We’re an e-commerce provider. Eight years ago, I would have said that, or I was an e commerce writer for small business eight years ago would have been like, well, we’re an e commerce provider for small business that turned into big businesses, in some cases, six years ago would have said that we are a commerce provider, because we do online and offline. Four years ago, I would have said, Well, you know, we’re a retail operating system, because we do all types of, you know, we enable you to sell anywhere you want. And today, we have a capital program, it’s given out of more than a billion dollars of capital, we have a payments business that is a large shipping film business, and there’s a lot of surface areas inside of Shopify. And so you, as someone that works at Shopify, whether it’s for a long period or a short period, we don’t want you jumping around too much. Because you know, you need to get deep in something before you have the conversation to go to something new. But there are enough opportunities that almost all these different teams, organizations at Shopify almost feel like you can have multiple careers at the same company. Not only do we make that available, we encourage it, we think it’s a really neat thing. My job today is very different than my job 12 months ago, and one that is scary as hell, but it means that my growth continues, and it doesn’t slow down. It also means I have to get good at new things all the time. It means I have to learn about new industries that I never thought I would. I think that’s a big part of why people stay at Shopify for a long time. Again, it goes back to if you can get 10 years worth of career development every year at Shopify, why would you leave, if you can sort of Choose Your Own Adventure across a whole bunch of different types of industries, be banking and payments and capital, or fulfillment and shipping, or e commerce or physical commerce, or international expansion or whatever it might be, or API’s and building the partner ecosystem and making sure there’s no better place for an app developer to ever have to build a commerce related app that leads to this very, very long term tenure. And the benefit of it, besides the individual, is that at Shopify, because there’s so much stuff happening, the longer you’re at the company, the more context you have, the more you’re able to connect different dots. And when you can begin to connect different dots. Because of that deep context, you are very valuable, you are very effective, you can add a ton of you can have a huge impact.

Aydin Mirzaee (  38:16

That’s incredible. And I love that context building and moving that from area to area. It was really interesting hearing you describe this, you know how Shopify has transformed its mission over the years. And, and and you are right, I do remember you describing Shopify in those ways, a lot along the process. If I remember correctly, you had this value: was it thrive on change? And so it’s really interesting just to know, how that relates, but not just to the growing of the business, but also, you know, allowing people to change their careers. I love that value. And it makes a lot of sense. When did you really understand how impactful culture was to where your company is today?

Harley Finkelstein (Shopify)  39:02

Well, I mean, I think I’m reminded of it almost daily. I mean, I think the Irish Prime Minister when COVID was hitting said, This credits amazing speech. And one of the one of the lines he had in the speech, which I remember was, let the world say about us. He’s talking about the country of Ireland here. Let the world say about us. When things were at their worst, we were at our best. I just love that. I thought that that was poetic, I think the way that Shopify showed up during COVID, in a pandemic, to not only support existing entrepreneurs and existing small businesses, but also invite more people to supplement their income to replace their income to adapt and pivot their business. I’m really proud of how Shopify adapted when the worst pandemic since 1918, Spanish Flu hit the world. And I think a big part of the reason that we’re able to do so is because of that culture, which thrives on change. Now, there’s a hack to that too, just to be clear. I think it was Patti McCormick, who was at Netflix, she was the one who created the Netflix culture deck, which creating a culture deck is not, you know, nothing mind blowing. But what I thought was interesting was the culture deck was actually given to folks that have not yet started at Netflix before they started. So almost, I think it was part of like, the application process was, hey, review the culture deck. If this seems like something for you, continuing the process, if it doesn’t, cool, it’s not for you. What I loved about that was it was basically a warning label on Hey, if you’re going to come work here, here’s what’s expected of you. And I think because we not only believe in this thrive on change value internally, but also, just like you’re mentioning, that people know that thriving on change is a big cultural value. Some people don’t like change, some people don’t want to thrive on change. Some people want stability, they want certainty. Shopify doesn’t have certainty, the business we’re in is changing rapidly, we’ve had 10 years worth of digitization of retail in the last nine and a half months. So it’s just this is a place where if it’s part of the reason why I think a lot of founders and founder types and entrepreneurs do really, really well at Shopify, because inherently to that entrepreneur condition is the need to pivot, adapt, drive on change. And so that, you know, I think that it was a good culture, a good cultural value has a timelessness to it, the only thing I can tell you about Shopify, whether you started in 2010, or 2015, or 2021, is that it’s going to change. And if you like that sort of stuff, we invite you in, you’re gonna have the most incredible journey with us. But if that’s not what you want, if you want to know exactly what your job is gonna look like for the next, you know, five years, or three years or 10 years, it’s probably not for you. And that’s okay. It’s not for everyone. But the other side of the culture thing that I think people get wrong is a culture is not static, that the culture should change with every new person, it should get better. The average quality of our team should get better with every new person that joins and the culture should be a living tree, should be a living thing, it should evolve, it should develop. And that’s, that is the healthiest way for a culture to not only continue, but to continuously improve. And that’s kind of what we look at, what you put on your wall. I mean, you remember, in the early days of Tucker’s marketplace, we had all types of signs on our wall, you know, get shit done. And, and, and things like that. Those are interesting. But what culture really is, is what are people doing when no one is looking? What is the level of care that they have? When shit is going sideways? How do they react to that? That’s what culture is.

Aydin Mirzaee (  42:32

Yeah, I love that. And it’s so interesting to see it just melted into every avenue. And I love this, like pre-framing what the company is going to be like setting expectations. I think it all ties very well together. Harley, I know we’re getting close to the end of time now. So it’s been so valuable. So many, so many really great insights. One question that we like to ask just to as a sort of, like, final question, for all our guests is for all the managers and leaders out there looking to constantly get better at their craft, what words of wisdom parting advice, books, resources, tips, just anything that you’d like to leave them with?

Harley Finkelstein (Shopify)  43:13

There’s also great books and a lot of great podcasts like this one, there’s lots of great resources to go and acquire information. I think the best thing that I’ve done for myself is to to get better as a manager to continue scaling my leadership qualities is just to find a really great people who they do something one thing that I really admire, I did this by the way, you know, when I got married to Lindsay, I did this when I had kids I looked at who are the best husbands out there. Who were the best dads out there who were the best, like people at the craft of romance and ask them hey, like, how do you keep you know, you’ve been married? You know, for 65 years? You seem incredibly in love. like as if you got married yesterday? What are some of the things you do? What are your rituals? What are the things that you do together? How do you keep that spark? I’ve tried to the same thing with with with managers and leaders as I you know, I get a chance to meet some amazing people, amazing leaders and managers all over the world in some of the biggest companies but also you know, at the butcher shop here in Beachwood where we live and watching the way Andy at the bookshop interacts with his team is inspiring. And he has taken people that don’t care about the cut of meat, whether it’s a ribeye or a strip or or a film in your and somehow we convinced them to get incredibly passionate about this stuff. Okay, well, Andy the butcher, how do you do that? And I think that if you begin to make a list either on a piece of paper or digitally or you just make a list in your head of people that you start noticing, hey, I really like how they do to be one of the greatest managers on the planet is Stephen Beckta. Stephen Baxter, who is one of my closest friends who runs three of the greatest restaurants in Canada. He not only cares about the customer, as well as restaurants, but the way that he’s able to get his staff to care so much, that in itself is just, it’s brilliant. And even though he’s in the culinary restaurant food business, and I’m in tech, there’s so much I can learn from him. And when you begin to sort of create a bit of a list of people and managers and leaders that you want to emulate, you can just ask them questions. And I think if you just focus on your particular industry, you’re going to miss out. But if you take a much wider perspective on the best managers, whether it’s any of the butcher it, Steve, back to the restaurants, her or it’s Aydin, the CEO of Fellow, you begin to build a really amazing catalogue of tactics and best practices and tricks to use something as simple as someone told me years ago, as an executive, at a Silicon Valley company at a big tech company, start your one on ones by saying, What can I do to be valuable? That’s it. What can I do to be valuable as a way to start one on one? I now do that every single one on one, you can ask my team, I’m not sure if there’s diminishing marginal returns or not, but that is created for that to change the tone of that one on one, it means that I’m there to serve. I’m there to help however I can. And so creating a set of mentors, and people that you really admire when it comes to managers and comes to leaders, has been very effective for me.

Aydin Mirzaee (  46:18

That’s great advice. Thank you, Harley. Thank you for doing this. 

Harley Finkelstein (Shopify)  46:27

Thanks Aydin.

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