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

1. 0:00 – 15:00

   (beeping) Three, two, one,…

   1. HSHarry Stebbings0:00

      (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.

   2. HFHarley Finkelstein0:15

      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-

   3. HSHarry Stebbings0:49

      Hah.

   4. HFHarley Finkelstein0:49

      ... 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.

   5. HSHarry Stebbings0:59

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

   6. HFHarley Finkelstein1:02

      (laughs)

   7. HSHarry Stebbings1:02

      ... 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-

   8. HFHarley Finkelstein1:10

      (laughs)

   9. HSHarry Stebbings1:10

      ... 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?

   10. HFHarley Finkelstein1:16

       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.

   11. HSHarry Stebbings1:30

       (laughs)

   12. HFHarley Finkelstein1:30

       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.

   13. HSHarry Stebbings3:15

       Huh.

   14. HFHarley Finkelstein3:15

       And that mentor, uh, happened to be teaching law in 2005. He took a year off from his practice of law, um, he was a lawyer, uh, to teach law at the University of Ottawa. And so he said, "Why don't you apply to University of Ottawa?" And so I did. I applied to one school and, uh, luckily got in, moved to Ottawa in '05, and had no friends, had no family in Ottawa. Had never been to Ottawa in my life. It's the capital of Canada but I just had never been here. And so I immediately asked, what I always did when I was looking to make friends, y- "Wh- where are the entrepreneurs?" And I was directed to a coffee shop, uh, and I met a bunch of really amazing entrepreneurs. Um, and one of those entrepreneurs was Tobi. And Tobi was just... This is, uh, 2005 or so, so Tobi was just transitioning from selling snowboards on the internet, uh, he had moved to Canada, uh, from Germany and needed to make money, couldn't get a job 'cause he was a new immigrant. So he started a business selling, uh, snowboards on the internet. Frustrated with the lack of great software to sell something online, built this piece of software and sold the snowboards. And by 2005, it became clear to him that the software behind the snowboard business was more valuable than the snowboard business itself. And so he, he launched Shopify. And, uh, in that sort of first meeting I told him that, uh, you know, I was new to Ottawa, um, I had this wholesale T-shirt business that I wanted to move online, and I was intrigued by Shopify. And so I became one of the first merchants to use Shopify and, um, and I built an online T-shirt shop. And basically all throughout I was doing a, a joint law/MBA, uh, so all throughout law school and business school, I, I studied, but, I mean, I looked at law school more as, um, a selfish pursuit of ac- acquiring new skills. How can I be a better writer? How can I be a better reader? How can I be more articulate? How can I bet- be a better critical reasoner and debater? And all those sort of things. So law school for me was really more like finishing school for entrepreneurship. Um, but I also ran this business all, all along the way. And then in 2009, I was... I finished school and I was practicing law in Toronto, and I was hating law-

   15. HSHarry Stebbings5:11

       (laughs)

   16. HFHarley Finkelstein5:12

       ... and I called Tobi and, uh, I sort of begged him to let me come and join him and a very small handful of, of other people, mostly engineers, and, uh, join him on this journey to, um, you know, get Shopify out to the world and, and help more people become entrepreneurs. And that was about 13 years ago.

   17. HSHarry Stebbings5:28

       Man, I, I wanna go back a little bit. You know, I... you mentioned kind of my work ethic before. I have the work ethic 'cause my grandparents lost everything when I was very young and I saw them lose everything, and I promised myself I'd never let my family be in that position again.

   18. HFHarley Finkelstein5:41

       Right.

   19. HSHarry Stebbings5:41

       That's why I work my fucking ass off (laughs) . Um, you mentioned there losing everything. I, I, I hope it's okay for me to ask, how, how did you deal with that, one, and then two, how did it impact you do you think? Like for me, it made me just unwaveringly and unhealthily obsessive about winning.

   20. HFHarley Finkelstein5:59

       If you just look at COVID, for example, it was a great exam- it was a great opportunity to see this in, in r- in real time.Covid hits pretty much the whole world February, March, April 2020, and there was... You pretty much saw one of two reactions from people, from businesses, from, from corporations, from, um, associations. Just generally, there was a, there was, there were two ways that people reacted. One way was the sense of resistance that, "This is bad. I can't wait to go back to the, the old way." And there was this other group of people that were incredibly resilient that basically, you know, they saw this tidal wave and they took their surfboard and surfed and surfed. And, and, and they saw some opportunity in what was frankly, uh, you know, a global devastation. And I, I think that's kinda how most people deal with, with real big setbacks. Um, they either go to the couch and, and put their blanket over their head or they get up and, and they try to figure it out. And, um, I... The reason that I, the reason I've committed my entire life, both professionally with Shopify but also personally to entrepreneurship is because I think entrepreneurship is this incredible tool to dealing with incredible setback. Um, if you lose your job, you can use entrepreneurship to supplement your income. If your dad goes away and your mom and s- and sisters have no money, you can use entrepreneurship to make money concurrently while you're in school. By the way, entrepreneurship is not easy. Uh, it's not, not to say that everyone, you know, will be successful at it, but, you know, different people have different versions of success. And so my version of success when I was 17 and sort of the world ended for my family was survival. And I think, you know, same... My, my, my grandfather was a Hungarian immigrant, a Holocaust survivor. Comes to Canada in 1956, gets to Canada 'cause Canada had let in 40,000 Hungarians during the revolution in Hungary. His job wasn't necessarily, you know, to find his craft or to find his life's work. It was to survive and the way he did it was he sold eggs at a farmer's market for, you know, 60 years of his life. And I think those are the types of people, those sort of resilient people that see, um, devastation and try to find opportunity or try to make the best of it any way they can. Those are the people I think ultimately that, that, um, that I admire the most, that build the most character. Um, and, and so that's kind of how, you know, I, I sort of deal with... E- even today in, in our business, you know, Shopify is an incredible business and great company and, you know, two million entrepreneurs have, have been served by Shopify and hopefully many millions more. But on a day-to-day basis, there are setbacks, there are issues that happen. And I think the way that, that I try to deal with those issues is to say, "Okay, what can we learn from this, this setback? What are the opportunities that are now available that weren't?" Um, and Covid just going full circle was, was a great example of that because there were so many businesses that had yet, let's just say physical retail stores, that were not digitalizing fast enough or just didn't digitalize because they didn't feel they had to. And then you had this sort of mass catalyst of digitalization that was required of them because physical stores were closed. And on the other side of it, you have these businesses today that I think are better businesses, more resilient businesses, in many cases more profitable businesses than ever before. And it's because that trauma, in this case Covid, caused this incredible change to happen.

   21. HSHarry Stebbings9:21

       You're applying it back to the business there. I, I spoke to quite a few of our mutual friends before the show, and it was actually Amish at FirstMark who mentioned your empathy being almost unlike any other that he works with in terms of the operators-

   22. HFHarley Finkelstein9:32

       Mm-hmm.

   23. HSHarry Stebbings9:32

       ... and how you apply it to the business. I wanted to ask, how do you think about like what truly great listening means to your team and how do you think about creating that safety and that safe space where they can come to you with any of their problems and be much more open and candid than one probably used to be with a boss?

   24. HFHarley Finkelstein9:49

       Yeah. Yeah. Well, it's very kind of Amish to say that. Um, Amish has been a huge part of the Shopify story. As you know, he was, uh, he was in our series A, uh, first market in our series A back in, in 2020, 2010. Uh, it was actually, it was a seven million Series A, I think on a $25 million post valuation. So, uh, you know, we've come a long way since then.

   25. HSHarry Stebbings10:08

       It's a pre-seed today. Pre-seed. (laughs)

   26. HFHarley Finkelstein10:09

       Uh, yeah. It's n- it is crazy. Um... You know, I think for a lot of entrepreneurs and a lot of leaders, there is this, um, desire to go really, really fast and there's sort of this hyper, um, you know, efficiency drive that like, we're not gonna have a conversa... If the conversation should take 10 minutes, we're not gonna, we're not gonna take 20 minutes. It's gonna be a 10-minute conversation because I gotta go do something else. I gotta go s- to the next, the next item on my to, to-do list. And one of the things that I've felt that I was bad at, uh, in the early days was I would just, you know, that's how I ran my day-to-day. Um, don't get in my way because I'm, I'm, I'm a bull in a China shop and I'm, I need to get shit done. In fact, it's one of the cultural values of Shopify is get shit done. It only sort of dawned on me through, um, coaching and frankly some, some, some really well needed personal growth that I'm actually not as efficient as I th- as I thought I could be. Because even though I thought, uh, the 10-minute meeting was sufficient to provide the, you know, the roadmap to where we need to go to our desired destination, no one actually really understood what I meant. And they were sort of just nodding because my reputation or my, you know, my brand inside the company was, you know, Harley's going to be, he's gonna speak very quickly and you need to listen and you need to go. Um, and over time it became obvious that I wasn't actually being very efficient. In fact, I was being the opposite of efficient because I had to have a second meeting afterwards to re-explain, uh, in a different way to the team what actually I was talking about. And so I began to use new, you know, devices or new techniques and say at the end of the meeting, "Hey, like now is the time, if anyone doesn't understand what I mean, like now is the time to say something. And if you don't wanna say it right now (laughs) in front of the whole group, send me a Slack note immediately after and say, 'Hey, I'd like to just get another, uh, I'd like to do another summary.'" And what I started doing was, one, I would record the initial meeting, um, and then I would record all subsequent meetings should they be needed, like should they need additional explanation. And it turned out that as I began to do that more often, um-... yes, the meeting length may, may have expanded slightly, but in terms of productivity, it also expanded. And I, you know, I think for a lot of us, there's this kind of, you know, survival, going back to survival again, with early stage businesses where you need to fight all the time. And if you're not fighting, you're not grinding, and you're not hustling, and you're not, you know, working super hard all the time, you're not gonna survive. And there is an element of that. I mean, there's tons of hard work that goes into it. But as the company grows and the team expands, Shopify is now more than 10,000 people, I needed to change the way that I communicated. I needed to change the way that I, um, I provided a vision or direction. And the cool part is, the more you see it work, the more you realize, "Hey, like, like I'm g- I'm... This is a new tactic for me. This is a new tool I'm gonna use in my tool belt." And I think that that is all about empathy, which is like, okay, you think you're being clear. What does the other people, person think? If they don't think you're clear, then it doesn't matter what you think. Um, and so over time, it's not that I became, uh, m- an empathetic person generally. My wife would say that I still lack empathy in many situations.

   27. HSHarry Stebbings13:21

       (laughs)

   28. HFHarley Finkelstein13:21

       But, um, I recognize that I can get more by simply trying to understand how the other person is receiving it. And so, um, it's just a better way to do business.

   29. HSHarry Stebbings13:33

       I, I, I, I totally get you. I do have to ask you, in terms of the empathy there and the communication with the team, one thing that I find... Man, you have thousands, I have, you know, tens, but not everything is going great all the time. And I spend so much time, you know, Wolf of Wall Street chest pumping, (laughs) going, "We're gonna change the world," and sometimes it's not, and it's just not happening. And my question to you is, can you be vulne... 'Cause I know we speak about power of vulnerability and all that, which is true, but it's hard, and you don't want to demotivate the team. Can you be vulnerable today? And if so, how can you? And I guess you're kind of advising me here, 'cause I don't wanna lose the morale, and I don't wanna lose the excitement. How do I do it?

   30. HFHarley Finkelstein14:15

       Let me give you one great example, heh, that, that really worked well for me. Um, I've had anxiety for the ma- the majority of my life. Um, it was undiagnosed. I didn't know what it was, but there was this, always this thing that, like, I felt deep in my stomach or my gut or my heart, whatever it was. And it manifested itself in a lot of different ways over the years. Um, but eventually, you know, I wanted to understand more about... I wanted to be more self-aware. I wanted to be more self-introspective about, like, what drives me, wh- what are, what are things I need to work on? And so I began to see a psychologist, and I'd been seeing a coach for a while. And eventually, it became obvious that no, I... This thing that I have that I'm describing to all these people, it's anxiety. And so

2. 15:00 – 30:00

   You, you mentioned the…

   1. HFHarley Finkelstein15:00

      the cool part about, um, knowing that is now, now I have all this... now I have a, a terminology for it. Now I have nomenclature that I can say, like, I can go read books about anxiety. I can talk to people that, other people that have come out publicly that said they had anxiety. So one, getti- getting that language is really valuable. And then the second thing that I did was I began to talk about both internally at Shopify, but also externally, that I have anxiety. And the most remarkable thing happened. All these other people who I deeply respect, who I admire and look up to, they came to me and said, "Hey, I also have anxiety. Here are some of the tools that I, that I have to, um, that, that I, that I've used," whether it was mindfulness practice, or it was, you know, walks with the dog, or it was, you know, books to read or podcasts to read, or, you know, s- taking a 10-minute, you know, music break in the middle of my day. Um, all of these things actually made a huge difference. So one, I now was able to manage my anxiety better because now I can... I, I have a term for it. There's nomenclature. Second, I was on the receiving end of all this amazing advice from all these wonderful people about how they do it on their own. But the third thing, which is sort of this incredible bonus that came from it, is I started hearing from people that I seem far more approachable, that even though, you know, um, I don't really bang my chest, but, but I, you know, I'm, I'm... I spend a lot of time, you know, trying to motivate and get people excited about Shopify's mission, which is not a very difficult mission to get excited by. I mean, you know, we're trying to become the entrepreneurship company. If you believe in that, you're gonna be excited by that. Um, but it made me far more approachable. It made me more human. And what I've actually come to realize is that, um, in the right circumstances, with the right, you know, um, sequence of words and, uh, true... like, true... Like, not, not... I'm not talking about false modesty or false authenticity, but true authenticity, vulnerability actually can come off as an incredible strength, not a weakness. In fact, the opposite could be true. Um, bravado, particularly false bravado, uh, where people do see, you know, e- that there's no way Harley is always this motivated, always this ambitious, always this strong, um, that actually comes off as inauthentic. And therefore, this, when you, when you, when you're always banging your chest, and you're always kind of doing the, you know, the Wolf of Wall Street thing, um, there is always this filter that is g- that goes on everything you talk about which effectively makes you 10 or 15 or 20% less effective because they put on the Wolf of Wall Street filter, and they're like, "Yeah, yeah, we, we know, we know." Um, whereas by being more vulnerable, which means you're being more authentic, I find that people listen to you in a different way. And I actually, I think it's, it's, it's a wonderful way to, uh, to live, just, uh, as a human being, but it also, um, it brings your team closer to you. It creates a lot more connection with the, with the people you're talking to.

   2. HSHarry Stebbings17:51

      You, you mentioned the anxiety there, and I didn't actually know that. I, I, you know, I never like to, you know... Um, I'm always very cautious about the words that people use, especially kind of medically, you know? But I, I get very anxious today and feel often very insecure, bluntly, you know, manage a quarter of a billion dollars, which is a joke considering when we were five years ago. I had about 50 quid-

   3. HFHarley Finkelstein18:11

      It's an amazing thing. (laughs) Yeah.

   4. HSHarry Stebbings18:11

      ... to my name.

   5. HFHarley Finkelstein18:11

      (laughs)

   6. HSHarry Stebbings18:11

      Um, but, like, I'm always terrified I'm gonna be Macaulay Culkin, you know, the kid from Home Alone, where everyone's like, "Oh, where is he now?" and you're like, "Oof," (laughs) "I don't, don't know." Um, my point being, like, that's my big insecurity and, and fear. When you look today, man, respectfully, Shopify is vast company, and you're the president. Like, what insecurities do you have today? And I guess, you know, when you sit o- on your own in the armchair, what are you like, "I'm really insecure about this"?

   7. HFHarley Finkelstein18:41

      Um, I read this thing a couple of days ago, which I loved. I'm gonna try to pull it up here for a second, 'cause I wanna get it, I wanna get it exactly right. It goes like this, um: "The most important law of ecology is this." So there's, I think there's four laws of ecology, and this, this, this writer says is the most important law. "For an organism to survive, the rate of learning must be equal to or greater to..." Or excuse me, "Must be equal to or greater than the rate of change happening around them. With the rate of change escalating, we must learn faster, learn better, and learn more." I think a lot about that. Um, I- I- that's, those are, that's- that's a better way to put it. That's a better sequence of words than I've ever used, which is why I wanted to, I wanted to quote that directly. But that- that's what I'm insecure about. Um, I'm insecure about the fact that Shopify has, I think, one of the most incredible opportunities of any company that's ever been built to truly change the way entrepreneurship, business, independence, success is created. And again, not everyone is gonna want to take their company public, uh, like, you know, Figs or Allbirds, uh, on Shopify. Some, you know, set up stores on Shopify and businesses simply because they wanna put food on their table, like my grandfather, or they wanna afford, you know, ballet lessons or hockey lesson, or, you know, um, whatever it might be. But I think the opportunity that Shopify has is so unique. There's never been a company, I- I think, and- and- and I try to study this, that- that has the chance to be the world's entrepreneurship company, to create a real movement to encourage more people to do this thing that we call business creation. And I think business creation is important, because I think it's- it's not a perfect meritocracy, but it's the closest thing we as humans have to a meritocracy, where doesn't matter what your last name is or how much money you have. What matters is, do you, have you created something of value that someone else wants? And then we make it really easy. So, when I think about the opportunity that Shopify has, when I think about my role here, what makes me insecure is, I need to grow faster than Shopify. I mean, Shopify is growing really, really fast. I mean, 10% of all e-commerce in the United States is done via Shopify. Every 28 seconds, a new entrepreneur gets their first sale on Shopify. Um, these are incredible numbers. And so ... Now in that case, that insecurity actually drives me. So that's sort of why, or I think there's some nuance with this whole term of anxiety. And it goes back to the resistant versus resi- resistant versus resilient. I actually think you having anxiety about the fact that a quarter billion dollars of other people's money is being entrusted to you is probably incredibly motivating. And that's where we get into this, this difference between, you know, eustress and distress. Distress or distress can paralyze you. Eustress can be incredibly motivating. And I think that's sort of where the more you talk about these things, the more you have a- a good sense of mental health and what, you know, what this is, how I'm feeling right now, the more you can hone it and turn that vulnerability into (laughs) I hate to use such a cheesy term, but into a superpower. I actually think because I worry about Shopify growing so fast and my need to keep up, it is the greatest motivator for me learning, growing, adopting new habits, new tactics, and trying to have a great network of people that I can learn from. And I think in that way, um, it can be really valuable. And that again goes back to why it's important to talk about things, these things, because all these new tools that I have around managing anxiety that have helped me continue to grow, uh, at- at the same pace or faster than Shopify, um, I never would have had, I wouldn't have had half those tools if I wouldn't be talking about this stuff.

   8. HSHarry Stebbings22:22

      Can I ask, what's the difference between eustress and distress first?

   9. HFHarley Finkelstein22:26

      Well, so my wife's a psychotherapist, so I- I get all these sort of psychotherapist terms thrown at me on a daily basis. But one i- one is just how ... It- it's- it's simply two different reactions to stress, and one is paralyzing and debilitating, and the other one is action oriented and actually fairly, um, uh, fairly motivating, um, actually. I- I wasn't, I didn't want to use the term motivation, but- but it does, it motivates. My stress, and I think your stress to some extent, can be incredibly motivating if we hone it. Um, whereas other people's stress, um, when it's not managed properly, can be, you know, paralyzing.

   10. HSHarry Stebbings23:05

       You- you mentioned that kind of growing at the same rate that Shopify does. That's really fucking hard. (laughs)

   11. HFHarley Finkelstein23:11

       Yeah.

   12. HSHarry Stebbings23:11

       Um, my question to you is, what does your coach say and how do you approach that then? Because it is such a challenging thing to grapple with. How do you actually approach that, and what does your coach and support system say to help you think through that?

   13. HFHarley Finkelstein23:25

       I hear this thing, uh, that entrepreneurship is- is a personal growth, uh, journey disguised as a business.

   14. HSHarry Stebbings23:31

       (laughs)

   15. HFHarley Finkelstein23:32

       Um, that's kind of what Shopify is for me. Shopify, for me, is this incredible company that also allows me to- to- to- to- to grow at this- at this in- at this rate. Um, look, I- I- I think part of that journey ... I've been at Shopify now, it's- it's like my- my Shopify bar mitzvah. I've been at Shopify now for 13 years. Um, I'm 38 years old, so about a third of my life has been spent at this company, and I- I- I don't take that for granted. It's- it's ... I'm- I'm truly, like I- I feel really, really grateful for that. Um, but part of it is not necessarily doing everything, and part of it is knowing what I'm really, really good at and honing that skill. And I think actually this is where a lot of larger companies get this wrong, I think. Um, Tobi uses this great analogy of like a river stone. You take this like beautiful spiky stone, and if you put it in the river over years and decades and hundreds of years, it becomes this kind of smooth and evenly, you know, uh, n- non-spiky river stone. We don't want to create river stones at Shopify. I don't want to be a river stone. I want to be spiky in certain areas. But in order to be spiky in certain areas, that means that I'm not necessarily going to be great at everything. And so having that, you know, that awareness to say, "Look, this is not ..." Like, I'm- I'm not a details person. I don't go into, like I'm not in this ... There are some leaders who like, they are spreadsheet leaders, they live in spreadsheets. I am not. Um, I'm a storyteller. I like ... And- and the greatest story I believe that I could ever tell is that of Shopify, which is that of entrepreneurship, which is that of Harley and my family and- and it's just ... I'm lucky that my, the Venn diagram of my personal life and my professional life overlaps so meaningfully. Um, but...... I'm never going to be the best, you know, uh, operations manager. Um, therefore, the people that I surround myself with need to be really, really good at that. And so, that is also something really difficult, I think, to a lot of us that are entrepreneurs because in the early stages of company building, you have to be the s- you know, the CEO and the janitor and the receptionist and the head of sales and the head of production and the head of support. You just don't have anyone else to do it. So, you end up accidentally being kinda everything to everyone. But over time, if you care about scaling the business, you gotta get really clear on like what ... you know, where you're gonna spend your time. And I wanna be world class at helping the world know, uh, about Shopify. I want the whole, I want anyone who's thinking about a business in the shower in the morning, or anyone that has a hobby and they have some inclination to commercialize that hobby, to, to know that Shopify is the entrepreneurship company. And that is-

   16. HSHarry Stebbings26:05

       Right. Right.

   17. HFHarley Finkelstein26:05

       ... that's my life's work. And so, anything that doesn't help with that, um, I can't just say it doesn't matter. I have a responsibility to supplement that with people that do care about it.

   18. HSHarry Stebbings26:14

       Man, I, I, I have a bold statement here, but one that I worry about, and it worries me when I meet founders. I think we've lost the art of storytelling. I think a lot of founders today, 99%, cannot tell a brilliant narrative, cannot really entice people along their journey, uh, blunderingly, I think, in the way that me and you can. And I think it's maybe ... I, I don't know if it's the proliferation of capital that means they don't need to, whatever it is. Do you agree with the lost art of storytelling? And I guess, what do you think, and I can answer this 'cause I have thoughts on it, but like, makes a great story? (laughs)

   19. HFHarley Finkelstein26:47

       I think what you're talking about is actually, um, I would replace the term story with mission. I think that a lot of founders, um ... Like you, I'm, I'm very lucky to invest in, in a bunch of different startups. And, um, obviously, you know, the, the, the obvious things are you look for grit and you look for vision, you look for, you know, someone who's just gonna grind and someone who is so deeply passionate about solving a problem. But I think the companies that, that I, I think have done really well is they have a deep understanding of what their mission is. And you can call it story, um, but it, but I think the two are, are pretty much the same. Um, you know, from a very early stage, uh, you know, Zuck and, and, and, and Facebook, or Meta, they were very clear on what their mission was. You may not agree with it, but their mission was to connect the world. Um, and, you know, Google had a very clear mission. Uh, it, it was to organize the world's information. I mean, later on, it was do no e- you know do no evil or whatever it was. But initially, it was very obvious what the purpose of Google was. And I think if you look at these iconic companies, you, you have those. Um, so I don't think there is a way to build, um, a 100-year business, which is what we're trying to do, and we're, you know, 15 years in now, uh, or to have a company that fundamentally changes the way things are done if you don't have a very clear mission. And the way that the mission is articulated to the world is through storytelling. And so, I, I, I don't know if it's a lost art or people simply just don't necessarily need it the same way at the early stages as they do at sort of later stages. Um, but, like, I think maybe this is in our, our first episode from five years ago. One of the first things I did when I got to Shopify, um, was I told Tobi that I was gonna put signage all over our building that said Shopify. And he said, "Why?" 'Cause there was no signage. There was, like, just a building and it didn't say Shopify. And I was like, "Because I want the world to know that this is where entrepreneurship is being developed, and I want the world to know this is where Shopify is, and I want people walking on the streets to see Shopify and wonder what that is, and then eventually connect the dot that this is the, the entrepreneurship company." So, I, I ... At any stage, I think it's important but, um, there isn't ... I don't think ... You know, there was a article that is now fairly well-known, uh, in October or November, uh, in the Wall Street Journal, I think, or, or Washington Post, about the great resignation.

   20. HSHarry Stebbings29:04

       Yeah. Yeah.

   21. HFHarley Finkelstein29:04

       So, it's an interesting article because, you know, it ta- talked about most people or how many people had le- have left their jobs. Um, but, you know, what is now pretty well-known is, they didn't leave the workforce. They left jobs they didn't like. And at the same time, I think the numbers were like 4.6 million new business registrations happened, uh, in 2021 alone in u- in the United States. Like, this massive jump from a decade earlier. So, I think in many ways, not only do companies need to be good storytellers, particularly right about their mission, but I think if they wanna recruit, they have to be super clear about, "Hey, the reason to work here is not 'cause of the stock options, not just 'cause of the comp, not just because of the work is interesting and you can have a big impact, but also because do you have a connection to what we stand for?" And the people that work at Shopify, you know, all 10,000 and more, I think have a deep connection to entrepreneurship to some extent.

   22. HSHarry Stebbings29:54

       I, I ... Yeah. And I, I totally get you. That- I love that in terms of the billboards. For me, it's like, you know, you could say I started,

3. 30:00 – 45:00

   Yeah, yeah. I mean,…

   1. HSHarry Stebbings30:00

      you know, the podcast from the bedroom of my family home and I interviewed a VC. Or you could say I remember being super nervous. I asked my mother to unplug the home phones in case someone rang. I only had $50 in my bank account. And then, I started with Guy Kawasaki. I was super, super nervous, and so I had a chamomile tea beside me. And you bring in the essence that make it so much more familiar for people. Do you see what I mean? Like-

   2. HFHarley Finkelstein30:25

      Yeah, yeah. I mean, you're t-

   3. HSHarry Stebbings30:25

      ... it make-

   4. HFHarley Finkelstein30:25

      ... you're talking about the craft of the storytelling. And I think the craft-

   5. HSHarry Stebbings30:28

      Yeah.

   6. HFHarley Finkelstein30:28

      ... of storytelling is incredibly important. I mean, you're- you- you- you run a very successful podcast. You- you sort of by, by very nature have to be a great storyteller. The relationship that I have with Tobi is effectively that and the same. I mean, Tobi, I think, is the pro- probably the greatest product, uh, h- mind on the planet. I mean, I just, I, I don't say that, um, boastfully. I, I say that from great, you know, with great insight and, and great experience working side-by-side with him for, you know, a third of my life. Um, my job is then to take what he builds and ensure the world knows about it. And the only way the world's gonna, gonna, gonna actually care about it is if I leave these, these breadcrumbs of, of storytelling and narrative. And, you know, if you, if anyone follows me on social media, I talk about Shopify's products a bit, but what I really talk about is our merchant story. Because for me, the way to deeply understand Shopify is to look at Ben Francis in 2013, uh, as a pizza delivery boy in London, uh, in college-... who decides to start Gymshark, and to watch his journey to be one of the most important athletic brands on the planet in 2022. That, and- and the way to do that is not to just talk about his numbers, but I start with what he was doing before, I begin to talk about, you know, why he didn't think that the existing athletic companies and- and- and the- the existing, um, brands out there, you know, it was either for, like, you know, runners or it was for, like, gym rats, but there wasn't anything in between that. And so, he felt that he can build a brand for that particular niche that- that he himself was. And- and so, I actually think it's important to become good storytellers, but again, going back to the whole, you know, knowing what you're good at, you don't have to be a great storyteller, uh, when you're getting started. But at some point you're gonna n- gonna need to find somebody who is not like you. If you're, let's say you're a great engineer or a great product, uh, designer. You may have to, you're gonna have to find someone who is really good at that craft. And that actually is another sort of subtle point, I think, that a lot of people start businesses with people that are just like them, people that they would be friends in high school with, but if you look at some of the best teams out there that have built incredible companies, um, they are really different. I mean, their Venn diagrams in terms of skillsets don't really overlap. Rather, they extend the- the, you know, the aggregate skillset of the entire leadership team. And, uh, you know, I- I think Tobi has done a really good job of surrounding himself with people at Shopify who are not like him, which means that what you end up with is you end up with an, like, a skill s- an aggregate skillset that covers all the important things you need, whether it's product or engineering or scalability, or it's, you know, operational excellence or it's storytelling and- and commercialization.

   7. HSHarry Stebbings33:06

      Can I ask one that I find so interesting, and it's, you know, when you look at the relationship that you and Tobi have, you know, across the board, everyone says it- it's fantastic, it's wonderful, it's my favorite word, wholesome.

   8. HFHarley Finkelstein33:16

      (laughs)

   9. HSHarry Stebbings33:16

      Um, but, uh, my question to you, and it- it's always very interesting. Can you take me to your last disagreement, or a disagreement that you can remember, and how you approach conflict resolution as a- as a professional marriage?

   10. HFHarley Finkelstein33:29

       Yeah. Um, we are not the same. Um, him and I are- are very, very different. I think that the key, uh, the key for us has been, um, at certain times there needs to be a, you know, disagree but commit. Um, but there's always debate, and I- I think part of, you know, you've heard me, I think you've heard us talk about the trust battery. I think the trust battery is- is a metaphor that still, um, is, uh, is misunderstood. Everyone that comes to Shopify starts at- at a 50% trust battery. Um, and the key is to get your trust battery as high as possible, because at that point, that's when debate, that's when, um, disagreement becomes far richer, because now you're not challenging each other's, you know, individual, uh, you know, minds. You're not challenging, uh, e- e- each other, you know, on a personal level. You're actually just challenging ideas. Your trust battery is at a requisite or a- a sufficient, you know, benchmark that you actually can go deep on a topic and it doesn't feel personal. And that, I think, has been the key to- to- for Tobi and I. In fact, the- the key to most great partnerships has been this deep mutual respect. Um, and I think part of it is, uh, there's a default. There are certain times where he'll default to what I think, uh, because it's my craft, it's the thing that I've studied more than he has, and the opposite is true when it comes to product or technology. I think that's- that's a major part of it. And the other part of it is, like, something that is not talked about, and you used the term wholesome, but it- it's fun. We enjoy working together. I know that there is this, and I may- I don't know, maybe this is, like, gets controversial a bit, but, like, I don't think fun is talked about enough. Like, when you are doing this for a long time, a third of your life, and hopefully it'll be, you know, half of my life by the time I'm done at Shopify, um, if it's not fun, it's not gonna b- it's not gonna be a great journey. You're not gonna have as much, you're not gonna get as much joy out of it. You're not gonna get as much personal growth out of it. It's always going to feel like a grind. And sometimes it is a grind. It's okay for it to be a grind. You can have a bad day or a bad week. You can even have a bad month. But over the long term, you have to have fun with the people you want to work with, and you're not gonna read that in a business book, and there's probably not gonna be many podcasts that talk about that element, but that is the X factor to great partnership, is that you actually have fun even in the heat of a very, you know, in- in- in the heat of a disagreement, and I think we have fun with each other.

   11. HSHarry Stebbings36:01

       You say there about having fun in the partnership with Tobi, you know, and we said about wholesome. You know, obviously we're friends on different social networks. Uh, you have the most wonderful, loving relationship with your wife.

   12. HFHarley Finkelstein36:11

       Oh, thank you.

   13. HSHarry Stebbings36:12

       Um, t- talk to me about what makes a truly successful marriage, and, uh, advise me, 'cause I want a similar one.

   14. HFHarley Finkelstein36:18

       Uh, so just so you know, I mean, what I put out on social media, um, is, uh, I- I hope is a reflection of my- my loving marriage, um, but I- I- I- I will say this because I- I know other people, uh, who I'm- I'm, I have an intimate understanding of their marriage, who, on social media, they look like they have the greatest marriage, and- and- and I'm not sure they- they do. So, just- just as a sort of warning to- to everyone listening that, you know, um, everyone's putting up their highlight reels, not their blooper reels. Which I- which I think is well known, it's just I wanted to say that out loud. Um, I don't think I started out as a good husband. I don't think I sort of knew how to be a good husband. One thing that was helpful to me was, in the same way that, you know, pre-IPO, um, through people like Jeremy at, uh, Bessemer and- and Amish at FirstMark, I- I started asking around, you know, who are some of the best public company leaders, uh, out there? And Jeremy and Amish and all these great people in my life would say, "Talk to this person, talk to that person. They've done a good job here. They've done a good job here." And I'd sort of pick and choose certain a- attributes or- or character traits or tactics that each of those people use, and then I'd sort of build my own version of that. I did the same thing with- with getting married. Um, Lindsay and I got married in 2013, and we'd been dating for four, four or five years previously. Um...But over time, I, I sort of began to see other couples and, and some, I was like, "Uh," like, "I don't know. There, there seems like there's a lot of issue there." And others, I'd be like, "I don't understand. Like, those people always seem like they have this great relationship, this great, you know, yin and yang sort of dynamic." And first of all, I, I, I needed to figure out if that was true or that was just, again, like the social media version of, of the relationship. And then once I was able to ascertain that yeah, actually these two have been through a lot together, and yet they're so close, they're so committed. They really are like, th- they are, they're teammates. Um, I would call them and say, "Look, I know this is kind of a weird piece of advice to give, but I'd like to be a good husband, and I'd like to know what that means, and I'd like to understand, you know, what are some of the pitfalls that I, I could make." And, um, part of what, you know, Lindsay and I, uh, I think have been able to, uh, to develop together, um, is one, you know, (laughs) similar to me and Tobi, we have a lot of fun together. But two, um, it is, it is Harley and Lindsay versus the world. We, we are a team. And sometimes like I'm on Team Lindsay because she need- she's going through something. And sometimes she's on Team Harley 'cause I need something. And that ability to switch roles and not necessarily be, you know, it's, it's, it's, you know, with the Shopify kind of, you know, brand and, and where Shopify is in the world, it's very easy that everywhere we go becomes the Harley show or the Shopify show. And, and I don't want that. Lindsay's a great entrepreneur. She's a great psychotherapist. She's incredible in terms of, you know, the way she looks at philanthropy and, and, and community contribution. And so there's sort of, you know, I know when I am, uh, her date and she knows when, when she's my date and, and we're okay with that dynamic. Th- the second thing is, um ... (laughs) We ... I'll just say it 'cause I think it's helpful. We've been seeing a couples counselor almost since like day one.

   15. HSHarry Stebbings39:19

       Huh.

   16. HFHarley Finkelstein39:19

       We've been seeing, we've been going to couples therapy. And we initially did it, um, because on the advice of someone that one of these mentors that I think has a great relationship who only started seeing a couples counselor, uh, years after they got married, after they had a traumatic experience. Uh, they started seeing a couples counselor and they're like, "Hey, this has been an amazing thing." And so Lindsay and I adopted it fairly early on in our marriage. And the way we sort of looked at it was, you know, in, in the same way that it is, it is always easier to start going to the gym and seeing a trainer before you sort of need to and when you're still kind of in good shape, um, as opposed to waiting till you're totally out of shape and it's really, really difficult to get into shape at that point. That's kind of the way we looked at couples therapy. And we still see a couples therapist, uh, every two weeks. Sometimes it's, you know, uh, a session about how well things are going, and other times it's... The couples therapy is a forcing function for us just to say the thing, just to be super candid-

   17. HSHarry Stebbings40:11

       Mm-hmm.

   18. HFHarley Finkelstein40:11

       ... and honest with, "Hey, here's how we're feeling right now. Here's where Harley is not being supportive." You know, one obvious, you know, one, one thing that comes up a lot is Lindsay has an issue with something and Harley's solution is to solve the issue, or Harley's reaction is to solve the issue. And so that, that, I just, I don't know why. Just, I just, that's how I solved, that's how I reacted to Lindsay's problem. I sort of, you know, like an entrepreneur of just being Harley, like, that's how I did it. I was, I'd hear about a problem, something happened with, you know, uh, one of our kids' schools. And I'd say, "Okay, here's what we're gonna do." And she's like, "I, I'm already solving it. I don't need you to solve the problem. I just need you to hear what I'm saying and tell me that, that that sucks." And I have a really tough time saying, "That sucks," because that's just not how I'm built. I'm built for solution. And so now what I do is (laughs) again, very simple tactic. She says, she comes to me with a problem and I say, "Do you want me to be, you know, just to be list- do you want me to listen? Is it just me listening? Or do you want me to help solve the problem?" And nine times out of ten, she's like, "I just want you to listen." And I'm like, "Great." My, like, I'm able to switch on my, my prefrontal cortex and, and quiet down my, you know, my, uh, my amygdala, my lizard brain and now I just listen. And at the end, sympathetically and empathetically, I say, "You know, that sucks." And I, and I, I believe, you know, I try to be, you know, honest about that. And other times she's like, "Can you help me solve it?" And I'm like, "Yes, I can. Give me the problem. We're gonna solve it together." That small, those, th- those two lines, um, "Do you want me just to listen or do you want me to help you solve it?" I think has, um, increased our dynamic in our marriage and frankly, like, the romance and love of our relationship probably tenfold. And I'm not sure I would have ever had that had I not gone to couples therapy and spoken to people that have great relationships.

   19. HSHarry Stebbings41:52

       I think one of the biggest fallacy of relationships is we're, we're inherently expected to know how the other person feels. And I think you're absolutely right. Ask, "What do you want from me in this moment? And then I will provide it." Um, and most often, as you said, it's just someone being listened to and being heard. We, we chatted before, um, you know, very lucky to have a new wonderful girlfriend, but I worry about reverting to this mean state of mediocrity. You know, you said there about being Team Lindsay and being Team Harley, bluntly I think the best entrepreneurs are really selfish. Um, and I have been really selfish over my life because I haven't had anyone else. And now I'm worried that I will have to be less selfish 'cause I've got Team Paola as well. So how should I think about reverting to the mean in that concern?

   20. HFHarley Finkelstein42:37

       You know, uh, you want to go fast, go alone. You want to go far, go together. And I think, you know, I want to go far in my relationship. I believe that part of my ability to, um, operate at this, I don't know, the, the, the beats per minute of my life is very high, with Shopify, with my personal life having two, I have a two-year-old and a five-year-old. Zoey is two and, and Bailey is five years old. The only, you know, the only way I can do this is if I have a really strong foundation, and that strong foundation comes from my family. Uh, it comes from my marriage to Lindsay. It comes from my relationship to like my, my, my closest friends, my dynamic with my, my colleagues and, and, and Tobi. Um, and so I guard for that and, and, and I, I think you need to decide, uh, everyone needs to decide whether or not they want to run their marriage like they run their business. Um, and I'm not sure that's always the same thing. I do think actually there are a lot of similarities to it. You know, we talked about empathy earlier or authenticity or vulnerability. I mean, there's some things that are just universal things that, um, I think humans need to-... need to adopt, 'cause I think you, you, you get better results with it. Um, but I think, you know, like let's say you do ... Lindsey and I have a ritual. We, we, we have date night. And date night has become a little bit strange during COVID, but we've now resumed date night. And sometimes the date night is like, I plan the whole thing, and I'm a, I'm a planner, uh, so I think about, like, not only what restaurant we're going to, but I, I think about, this is gonna sound weird, but I wanna, I, like, I know the, the, the number, the table number of the table that I love at all my favorite restaurants. And I know the chefs at those restaurants too, because I go there a lot. And so I'll text the chef and say, "Hey, I know this is not on the menu, but it's a special night for me. It's date night. I'd love to have this." And I'm, you know ... How you do anything is how you do everything, I think, to some extent, and so I just, like, that's how I do it. And then other, other w- weeks, I'm like, "Linds, like, you know, it's your night." And, and she may plan something totally different, and I just go along with it. And I gotta tell you, sometimes I don't love going along with it. Sometimes when Lindsey says we're going to this restaurant, I think to myself, like, did she pick the table that I like at that restaurant or not? And over time, you know, this is gonna sound, you know, this is gonna sound super weird and, and, and OCD or type A, but it is more important that Lindsey feels that she is in control of that particular date night, because it's hers, uh, than whether or not I'm sitting at the right table. And over time,

4. 45:00 – 59:03

   Can I ask, you…

   1. HFHarley Finkelstein45:00

      practicing that, like any other skill set, it gets easier.

   2. HSHarry Stebbings45:05

      Can I ask, you mentioned very openly, you know, not being a great husband in the early days. Do you think you've always been a great father? It's f- it's so hard when you're president of Shopify, um, there's 10,000 employees. Have you always been a great father, and have you had some lessons on what great var- har- fatherhood means to you?

   3. HFHarley Finkelstein45:22

      No, I have not. I'll give you the best example. Um, I thought (laughs) uh, I thought being a great father ... Here's a, a, a perfect example of that. I thought being a great father was on Saturday mornings when my kids wanted pancakes, uh, or what Bailey calls brunch, uh, she doesn't really, she says, "I want brunch this morning," which she means is pancakes and bacon and, and that sort of thing. Um, making the best pancakes and having the best bacon, um, and setting the table really beautifully, that made me a great father. First of all, if you, any of you listening have small kids, um, they don't give a shit about that. They don't care about how nice the table's set. Um, what actually my kids valued more was my presence. Was I actually there, and was I mindful of them? In the early days, so I, I'd make these great, you know, brunch breakfasts, and I'd set up this nice table, and I'd get fresh-squeezed orange juice and make these great pancakes. I'd watch YouTube videos on ... We have a flattop in our kitchen, which is a really cool thing to have, and I'd watch YouTube videos on how to make the best pancakes and all this stuff, and I'd present it. And then, like, you know, I, I'd be there, but I'd also be like checking email or I'd, you know, I'd get a phone call and ... And it was during one of these couple sessions with Lindsey that, um, uh, the couple's therapist said, "Well, Harley, are you, are you a, a present father these days?" And I said, "Yeah," you know, I gave all these examples. And, and the therapist and Lindsey both said, "That is not what she's talking about. Um, the kids don't value, uh, some special pancake mix or some special bacon. The kids value do you h- do they have your entire attention." And that was like, that hit me right over the head, because, um, one, uh, it frightened me that if I don't make some changes that this is, I'm gonna kind of be that dad. I don't wanna be that, I don't wanna be the dad who superficially is a good dad, but authentically is not, practically is not. And so those are some of the change that I had to make. But by the way, that's another example of why having a venue, like, I'm not sure Lindsey and I would have ever had a conversation one-on-one, "Hey, Lindsey, am I a good dad?" I don't think she'd ever come to me and say, "Hey, you're not a good dad." But having a couple's therapist say, "Do you think you're, you know, you're a good dad right these days?" Or, "Are you, are you a present father?" Uh, which is something that I, I would have, wouldn't have said, that all of a sudden created this conversation that, that created space for Lindsey to say, um, "You're, you're not doing it the way you think you are."

   4. HSHarry Stebbings47:41

      Final one, and then we'll do a quick fire, but what changes have you actually made to be that present, loving, real father that you wanted, not just the superficial?

   5. HFHarley Finkelstein47:50

      A couple easy, uh, easy things, uh, were, you know, I, I, I work- like to work out every day, um, but I'd kind of work out whenever I finished work. And so, you know, I'd be here in my, I'm in my home office here, uh, I'd be here and then, I don't know, 6:00, or 7:00, 6:30 or something, 7:15, I'd go to the gym, work out for 45 minutes, and then go up to dinner. And I'd almost always miss, uh, the kids. Uh, Zoey would be sleeping by then or Bailey would be in bed by then. And I just, I couldn't figure out how to do this, because it was important for me to work really hard, it was ... and get, you know, finish my day, finish the work. It was important for me to get some exercise in, 'cause I just feel better when I, when I work out. And it was important for me to see my kids. And I felt like I had to choose. And so what I did was instead, uh, I just hired, uh, I hired a trainer, um, initially it was virtually, now it's, now it's in person, um, who every day at 5:30 would show up at the house. And I, I recognize not everyone ... You know, I wasn't able to afford that, uh, frankly, up until very recently, but, you know, like, even, you know, everyone has, a lot of us have Pelotons. My suspicion is most of us do the on-demand classes, not the scheduled classes. But actually, if you have to do the scheduled classes, because you have to show up at 4:30 or 5:30, it means that is blocking it off. And so now, I finish my day by 5:30, 'cause that's when the trainer shows up, or the, or yoga teacher, I do 45 minutes to an hour. After that, I'm able actually to be a part, like, I'm able to see my kids, put them to sleep, and then after, late at night, I may come back to the office and do another hour of work if I need to. Um, so there are these sort of, um, really good concrete, uh, almost like bookends of my day now that, that are, that are immovable, because someone is showing up at my door at 5:30, that's when I have to work out. And there are times where, like, there's something so urgent happening at the office, at the company, where I'm like, "Hey, I, I can't work out today. Like, so, I know you're here, um, like, like, if you don't mind, like, let's, I, I'm, I'm, you know, we'll fi- we'll find some time, but I'm gonna be 20 minutes late." But more times than not, that has been a, a really important tactic. The second thing is, um, weekends, I really try to do activities with the kids on weekends. So right now, uh-... Bailey, who's five, is becoming a great skier. Uh, so I'm skiing with her a lot. Zoey is two. I'm trying to get her on skis. Last weekend was the first time. This weekend will be the second time. But having these projects we work on together, where they have my full attention, I have their full attention, that has been amazing. And so rather than just kind of, like, like, again, um, scheduling is, is really important. So I will schedule all these things. I will put in my calendar, like, a two-hour block to ski with Bailey. Some people listening are gonna think that's totally ridiculous, but that helps me be more of an attentive and a, and a, um, a mindful and, and a fully present father.

   6. HSHarry Stebbings50:23

      No, I, I totally get it. I love that. The only challenge is I got told that calendar invites were unromantic, so, uh-

   7. HFHarley Finkelstein50:28

      Th- they are unromantic.

   8. HSHarry Stebbings50:29

      ... please, if you-

   9. HFHarley Finkelstein50:30

      But the, like, you know what's n- even worse? Like, nothing. That's way worse.

   10. HSHarry Stebbings50:34

       (laughs)

   11. HFHarley Finkelstein50:34

       And so, you know, pick, pick your poison. And then Lindsey, like, Lindsey also doesn't like the calendar invites. She's like, "You are completely flooding my weekend with calendar invites." Like, like, "Do we really need a calendar invite for, like, go for a walk?" And I'm like, "Y- uh, w- I kinda do need that." And, and, and if you're able to be okay with a very unromantic calendar invite to go for a walk, it means that, like, I will, I, I, I can be there for you in a way that I probably couldn't if our weekends were just kinda like, you know, let's just see where it goes and, and kinda go with the flow. I'm not a go-with-the-flow guy, and I, and I embrace that, and, and that's okay. But I also wanna be a, a good husband and good, and a good dad.

   12. HSHarry Stebbings51:12

       Man, I, I so love this discussion. We're gonna do a quick part now-

   13. HFHarley Finkelstein51:14

       This is totally not what I thought we were gonna talk about.

   14. HSHarry Stebbings51:16

       So I say-

   15. HFHarley Finkelstein51:16

       But, uh, hopefully, it's interesting.

   16. HSHarry Stebbings51:17

       No, n- neither me, but this is why I love the show. But I'm gonna say a short statement, and you're gonna give me your immediate thoughts. Does that sound okay?

   17. HFHarley Finkelstein51:22

       Sounds great, yeah.

   18. HSHarry Stebbings51:24

       So what's the favorite book and why?

   19. HFHarley Finkelstein51:27

       Uh, the book that I'm reading right now, actually, which is, um, I'm just highlighting it, is, is this book called Ichigo Ishi, which is basically making the most of every moment. Um, if, if, do you know ikigai? Do you know that concept?

   20. HSHarry Stebbings51:39

       Yeah, yeah, of course.

   21. HFHarley Finkelstein51:39

       Yeah, so ikigai's well-known. But, but there's, there's actually a second book after. Ikigai, just for those that are listening, is, uh, the Venn diagram overlap of, like, what you love doing, what the world will value, what you can get paid for, and s- one other thing, something that, like, uh, that you, you know, gives you, I don't know, gives you great joy. Maybe I already said that. But it's basically finding your life's work. But there's a second book called Ichigo Ishi, which is effectively making the most of every moment. Th- th- it's, I'm not necessarily recommending that book. What I am recommending is for those of you that are listening that are entrepreneurs or running businesses or you're kind of, you know, hard-driving type As, I actually think there's a lot of value of not reading more business books. Um, I've r- I've read a lot. Every now and then, I'll pick up a new one that I think is really interesting. Um, I still think High Output Management by Andy Grove is still the best book that I've ever read on business. Um, but I'm not reading business books right now. Even podcasts. I'm trying to listen to, like, uh, right now, How to Take Over the World, which is a history podcast, or, um, All Songs Considered, which is a music podcast. I find listening or reading about things that are completely outside my day-to-day is so incredibly, um, interesting. And I love, even though I don't necessarily, I can't understand everything that Rick Rubin is talking about when he talks about music production, I love hearing someone that goes so deep in a topic that I know nothing about.

   22. HSHarry Stebbings52:56

       You know, Harley, since we stopped talking about business as much, and we started talking about what makes great marriage and what makes great fatherhood, show's numbers, through the roof.

   23. HFHarley Finkelstein53:04

       (laughs) Seriously?

   24. HSHarry Stebbings53:04

       And actually, it's all applied to ... Yeah, s- uh, totally true. It's like d- doubled, trebled.

   25. HFHarley Finkelstein53:09

       Wow.

   26. HSHarry Stebbings53:09

       And it's applicable to management. Uh, it, it, it, people want people. Um, so I-

   27. HFHarley Finkelstein53:14

       Love that.

   28. HSHarry Stebbings53:14

       ... totally agree. What's the hardest element of your role with Shopify today?

   29. HFHarley Finkelstein53:17

       Keeping up. Uh, I just, a- again, you know, Shopify grows so quickly. C- uh, can I, can I learn at an equal or greater pace as Shopify? And I, I only say that because I think, um, you know, it's, it's great that Shopify has two million stores. Uh, I, I, I think we wanna turn more people into entrepreneurs. And that's a massive, massive mission of responsibility. And, and m- what keeps me up is, is can I keep growing at this pace? And I think I can. But it, it, it's not, uh, it, it's very difficult.

   30. HSHarry Stebbings53:44

       Which leader do you look up to and why?

Episode duration: 59:29