Harley Finkelstein: You Must Requalify for Your Role, Every Year

26:48I think in order to be on our team, especially to be a leader at Shopify, you have to believe that you have to want to keep getting better, meaning stasis is not acceptable. The thing you did last year may have got you a high five and an attaboy and a pat on the back and whatever. All the great stuff that comes along with that, that is not good enough anymore. And actually at Shopify, I think that's truly, I mean, the source of that energy is Toby. That there's probably no one that I've ever met on the planet. I've worked with Toby now for almost two decades. You know him very well too. He's a friend of yours as well.

27:22There is no one that pushes himself to be the very best at product and technology the way he does. And so he inspires all of us to just continuously say, okay, last year was pretty good. This next year, I think I can, like, I think there's another gear left. That's actually the gift that he has given me in my career is that he's consistently over, you know, almost two-decade period, he has been the person more than anyone in my life, maybe other than Lindsay, who has seen a better version of me than I saw for myself. He keeps reminding me all the time. It happened a couple weeks ago. We were on an offsite that there is another gear in me.

28:04And so now he presents that optionality, that opportunity. And now it's up to me to actually go through. And I think for someone with my personality, with someone with my ambition, that works very well for me. What does it look like when he reminds you that there's another level for you? Does he just come? it doesn't come to you and say hey harley there's another level for you what does he say he's much more german about it um which is funny because he sort of calls it the german it's like the german thing for him but it's actually also like the jewish mother thing for me which is you know you just got 98 percent of your exam you go to your mom and your mom says great what happened the other two percent um which actually i've now learned it's actually very much uh um at least the way it's been described to me is that it's actually an immigrant thing but a lot Immigrant parents are like that.

28:53Like, that's great, but like, what happened here? How can you do better? So that's part of it. The other part of it is just that when he gives me a compliment, it is because I went so above and beyond. Like, he basically sets a bar for me of what great looks like. And doing my job really well is the expectation. Knocking it out of the park, resetting what corporate storytelling looks like. or how to do earnings, when you do that exceptionally well, that's when he says, that was a great job. And he's very thoughtful about how he explains, how he gives those, that was really great. He kind of shows you that thing you did that is so far beyond the expectation of the industry that you were resetting it.

29:44There's this really great thing we talk about, which is, it'd be really great, like I say this a lot, but I adopted from him, which is every person that works at Shopify should be able to go to their industry conference, whatever area they're in business, and they should give the keynote about how they're doing their job completely different than everybody in the crowd, which is like the most global maxima, not local maxima thing. It is like the local maxima is like, you know, you're at the top of the mountain, you're doing better than everyone else is doing your job. The global maxima, which is like Toby in a nutshell is there's a whole other man over here.

30:20That's where, that's how you requalify. And that makes it incredibly challenging, but also incredibly rewarding. There's this, you know, thing about life's work. I think it obviously gets lumped into like, you know, happiness and contentment and all that sort of stuff. Also, we can talk about how to find your life's work, but ultimately the way you continue to do your life's work is, is when you feel fundamentally that you can see serious progress. It's not type one fun. It's like type two fun. And type two fun is the type of fun that you only realize that it was fun after you complete it. In the middle of the race, it's not really that much fun.

30:58It's at the finish line. You're like, wow, that was fun. That tends to be the developmental journey of Shopify. A little anecdote about the that's your job, that's what you're supposed to do. I was at an NFL training camp and I was with Kyle Dubas, who was the GM of the Maple Leafs at the time. We were watching this practice and this rookie receiver caught the ball and it was a great catch, but he started celebrating. The coach came over and he's like, that's what you're supposed to do. Why are you celebrating? I'm paying you to catch the ball. Your whole job. You're paid to catch the ball. And it stuck with me ever since then.

31:34That's right. It is, I think when you're playing at a certain level of play, whether it's through podcasts or through business or through sport or music, you know, or art, music, if you try to, if you want to be above average, most people can get there. practice determination but this idea of thinking about things and sort of this like local maxima versus global maxima perspective creates a whole other surface area of which you can go and do crazy and cool stuff i do think that is difficult to do by yourself um i think you actually are one of the unique situations where you hold yourself to such a high standard that you actually don't need anyone pulling you to get better at your craft because you hold yourself to this ridiculous standard most people are not like that most people need someone else to help them pull up to the next level and if you find someone like that and you can you sort of mutually commit to one another i mean that's real partnership that makes for that's how you build a hundred billion dollar company i think it's fascinating because i tell my kids that right like when you're at school like try to partner with the people who are going to hold you to the highest standard who are going to demand the most from you who are going to show you what you're capable of and what you can do and they take that too and they hold other people to really high standards.

32:54That's right. And then you sort of, you know, it is ironic though, almost paradoxical, that the people that you often hang out with in high school or school in general tend to be very much like you. And what I've actually experienced is that I think the best partnerships, at least from a business perspective, are people that are totally not like you. Totally. I'm not sure Toby and I would have been friends in high school. I was class president. He was like taking apart computers in his bedroom. the people you tend to spend more time with that you gravitate gravitate to you you tend to have similar interests with you tend to have similar skill sets with you're both into basketball you're both into you know debate club or whatever it might be but actually if you're in high school right now and you're watching this and you want to start a company my my advice would be if you're in like drama club go find someone like in the av club and then go find someone in like the computer like the coding club and go find someone like who's painting and those should be your co-founders because each of you now can bring different skill sets to the table and together you can build something remarkable.

33:50My youngest wants to start a company and he's like, why should I go to university? Why do I want to go to college? He's like, I don't need that. And I'm like, well, maybe just to find a co-founder. That's what they do. Yeah. For all the Ulfs on Wall Street and tauben geckos there out there. For all the people who have blood on the internet, that's for you. Until the 28th of February, the POE will open and we will take your first order provision to 500 euros.

34:18I want to come back to sort of requalifying for your job though because you switched from being COO to being president or chief storyteller as you call it. Talk to me about that transition, how you came to realize that was the thing because you went from thousands of people reporting to you to a smaller number. Usually if it's a lot of people, it's still much smaller. at a 7 ,000 or 8 ,000 person company. Like a small number of people still a lot of people. But yeah, that was... Okay, so a couple things on that and a couple different sort of levels of abstraction, I guess. I do believe that there are different phases of companies.

34:58And I think at the early phases of companies, it's just mayhem. Like everybody do everything. It's like Swiss Army knife time. And in those early days of Shopify, there's a photo that every couple of years I put out on social media of me like mopping the floors. You may have seen it, but like, I may have mopped the floor once or twice, but it was, it's sort of a, you know, it's, it's a metaphor for like those early days that like the floor is dirty. You do everything. You do everything. That's kind of how it works. And then I think, you know, as the company begins to operationalize, you begin to have teams and organizations and general managers and divisions and all that.

35:33I became chief operating officer around just, just post IPO until around 2021, I think so for six years. I did it because that's what Toby asked me to do. We'd never had a COO before. And it was sort of this way of me looking after operations, specifically business operations. It didn't come naturally to me. But back to sort of the lifelong learner and the global maxima thing, and Toby pushing me into different directions, I was like, I'm going to get good at this. But it was never natural to me, never felt like I was in my flow state. But I liked it. I liked having a big team. I liked being responsible for a lot of things.

36:13because there was a little bit of ego in there. I felt very important. And it took me a while to realize that maybe this isn't for me. Maybe I'm not the right person to do it. Around the same time, I had someone that we had hired that was reporting to me who was running our payments team, Kaz. And in almost every interaction I had, it did sort of feel like, man, Kaz really likes operations. It feels like his ground state. He's kind of always doing it. And so I saw glimmers of what people that are truly operationally minded look like. But a couple hurdles I had. One is that I don't think I was ready to admit that this was not for me.

37:03This wasn't my thing. I don't like to admit that I'm not good at something. I prefer to get better at it. And I also, I think I was afraid to say the thing I want to do is like storytelling. It felt like maybe that's not enough. And it came with, you know, smaller team. It came with, it just came with less, you know, less areas of responsibility. Even though each of those were shallow, I was like, what I really want to do is this other thing. It's like one area of responsibility, but it's really, really deep. Is that enough for me? It became obvious to me that that wasn't the right thing. And actually, I think it became obvious to Toby that I wasn't very happy.

37:44I wasn't being my exothermic self. And for someone that's always been exothermic, that's always been high energy, at the end of my COO stage, I didn't have it. I wasn't meeting merchants the same way. I love meeting merchants. My favorite thing in the world. I just, I wasn't, it was clear I was in the wrong gear. And it was Toby that identified it and said, there's this other thing. We could find someone to be the chief operating officer. And it was actually between myself and Kaz Sagan, it was Toby Shannon who initially took in. He was a great chief operating officer, chief CEO as well. Toby almost gave me the permission to say, this other thing that you think is maybe not enough, it's like, it's totally enough.

38:32Like this is super important. And more importantly, you can be world-class at this thing. And that was this like huge aha moment. That was, it reminded me that, okay, the Venn diagram of what I love doing, you know, like, it's like the icky guy almost perfectly described. Like, what do you love? What is the world value? What can you get paid for? What, like, I forget all the different components of it, but that's generally the icky guy. immediately as I began to even understand what Ikigai was, I was like, that's it for me. It's like this role, the storyteller, the president of the company, where my job is to infect in the most positive way the world with the Shopify message that every enterprise merchant on the planet that should be on Shopify, I'm going to convince them to do so.

39:20That every partner that should work with us, I'm going to convince them that every investor knows exactly how great of a company this is, that every media opportunity I have, that I'm going to talk about this journey, this product, this incredible piece of software we've built, why it is so important, why it is so dramatically different than everything else that has come before us. I don't know, it was four or five years ago. It completely changed my energy levels. It made me exothermic again. It made me excited again. It made me want to recommit year after year after year to Shopify and to Toby and to this mission that we're on.

39:59I fell in love with the mission again. I almost forgot about the mission for a while. It became so operational. And what it also substantiated was that I didn't have to be good at all these different things. If the one thing that I feel I can be world-class, to go back to that concept, is sufficiently value-add that will change the company, that will change the direction of the company, that's enough. I am enough to do that. And I really think that most companies end up looking at a buffet of their leaders and looking at the slots that are available and just go like, go here, go here, go there.

40:41And I think it takes a very thoughtful and very often a founder CEO or founder leader like Toby, someone like that to say, okay, here are the players I have. Here are the things that are most important. I'm going to skill match. So it isn't who's been there the longest or who's had that job somewhere else. It is who is the very best person on the planet, not in the company, on the planet for this job. And that person exists here. That's the job they should do. It allowed me to recommit for a lot longer to Shopify, to working here, to helping to build this company. It's made me a lot happier. Even Lindsay would say that between 2020 and 2022, which I use those years because we're still in COVID and like we're still work from home and I wasn't around a lot of people.

41:26And as a power extrovert, that was challenging for me, but simply changing my area's responsibility completely re-engaged me. And it feels like this is a job that I always should have had. I think Shopify, I think Shopify had to get to a particular size in place for me to do this. It almost feels like Shopify kind of grew into the company that would allow me to be its storyteller. I couldn't have done this in 2010 or 2013 or 2018. It had to happen at the right time. And I'm super fortunate that it did and grateful that it did. I feel like you've had more of an impact than you think, not only on Shopify, but on other companies.

42:03I feel like the storytelling and getting out there more, like you've really changed the bar for a lot of other companies as well. So not only Shopify, but you've sort of set other people didn't even know it was possible to have that sort of impact. That means a great deal to me. That goes back to that industry conference that we talked about as a metaphor that I try to stand, I want to be able to stand up at the conference of every chief storyteller, every president of any company in the world and say, here's, I'm doing it differently. Lulu is on our board. He was an amazing, probably one of the greatest comms geniuses on the planet talks about this go to rec.

42:41She's a famous go to rec manifesto. That's kind of what I've always been doing. This idea that even the way that I treat earnings, it's not an earnings call for me. It's a storytelling opportunity. And I love seeing all these companies now. Now you see a bunch of tech companies turning the camera around and them I'm being like, here's how the earnings went. Like, I've been doing that for a while now. And so I'm - That's what I mean there. It's, I think it's really fun. And I, and because I'm now seeing other companies do that, I'm like, okay, so like, now how can I keep going from there? How do I, like, what's the next step here?

43:14How do I requalify? I've done that already. I've done the, like, go direct them on earnings. Like, what's the, what's the 10X version of that? What's the global maximum version of that? That makes it really fun. And despite what you may think of yourself, I think of you as a world-class storyteller. Thank you. How did you develop that skill? What does that look like? Like, how do we make other people world-class or better at storytelling? Practice really helps. You know, now I get to do like the knowledge process. It's like, this is a big podcast. I'm not trying to, you know, blow smoke or flatter you, but this is a big podcast.

43:46I didn't start by doing the Shane Parrish podcast. I started by doing a lot of tiny little local podcasts and watching them over and over again. You know, I know there's some people that hate watching themselves on camera. Maybe this sounds like narcissistic or something, but I don't mind. I actually like watching it because I was able to remove connector words, for example. I say, um, a lot less than most people do because I've watched myself do it a lot. And I'm like, I'm going to fix this particular issue. That's the first thing. The second thing is, I think a lot of people end up trying to emulate other speakers.

44:19I see a lot of, in tech in particular, there was an era where like everyone kind of sounded like Gary Vaynerchuk for a little bit. I know Gary well, he's a friend. I think Gary is an incredible, you know, speaker and his keynotes are legendary, but that's his style. and then you see other people that try to do the whole Rogan thing or the Shane thing or the Tim Ferris thing and and I don't I never tried to be somebody else I want it to be my the version of me which is a little bit excited not always as perfectly articulate I speak very quickly I want to make sure everyone understands me but I've sort of developed my own style of it and maybe the third thing which is probably obvious but great mentors people that I deeply look up to when it comes to speaking.

45:03And I think the person that has probably done the most for me in terms of watching how he speaks, how he captures the attention of a crowd with story, is Seth Godin. I think Seth Godin is the world's greatest storyteller. He can tell a story about Brussels sprouts. I have a great story about Brussels sprouts he talks about. He can tell a story about coffee or purple cows and watching him and talking to him and learning from him. and then it's just reps. How many reps have you done? I mean, the reason that, you know, Toby is such a great coder is he's written more code than probably anyone else at Shopify.

45:40Even now, I mean, he doesn't write as much code now as he once did, but just in terms of longevity of software development, he's had more reps than other people have done. We hear this about athletes all the time that like the greatest athletes were the ones that got up early, that went to the gym before everyone else got to the gym. Like they had a double workout. But that's a big part of it. I think the other thing is the content you talk about. I think it is really easy to talk about stories that are your stories. When I tell a story, whether it's about Shopify or it's about my life or my family or DJing or something like that, I always start with my experience.

46:20When I was 13, when I was 18, when I traveled here, I think by starting with you and you putting yourself into the story, one, it can't be wrong because it's your story. It happened to you. But two, it immediately invokes, if it's true, you can speak with such conviction, with such passion. the easiest story for me to tell is out of shopify because the story of shopify is a story of entrepreneurship and the store and but my story is also of entrepreneurship my family story about entrepreneurship my friends around me you know you know almost every one of my best friends they're all entrepreneurs some of them are in the restaurant business and some of them are in fintech and some of them are lawyers but what they all have in common is they all are first and foremost entrepreneurs.

47:12So the storyline that I've chosen is entrepreneurship. And it's not an accident that the company that I've committed to for so long for decades is the entrepreneurship company. Could I sell cars or could I sell biotech? Maybe? I don't think I can tell the story in that way. I think part of what is wonderful about modern day business leadership is that we are not selling widgets. I don't know if you've ever watched some of the old, like Glenn Gary, Glenn Ross movies, or I mean, frankly, like - Always be selling. Oh yeah, ABC, right? Closing. Always be closing. Always be closing. You know, copies for closers.

48:00You watch some of these old school business or even Wall Street, Michael Douglas, amazing movie. You watch these movies and you see these business owners in these movies, and it's a reflection, of course, of the society in time, but they were selling widgets. The executive could be selling tires, or the executive could be selling soda water, or they could be selling whatever. It didn't matter. They were implementing the same strategies to sell one widget as they would any other. In many ways, business is now way more personal. And I think one of the advantages of it being more personal is that you're able, like the company can attract people whose personal mission is tied into the company's mission.

48:42I don't think that there are any, when I look at every leader that I admire, business leader that I admire, entrepreneur that I admire, there's no accident for why they're at their company or why they built their company. Either they experienced a problem themselves and they went to solve the problem or they had something happen to them when they were younger in life and that kind of changed their mindset around that product. There is a deep connection to it. I mean, Fire Belly Tea, my little tea company that I served with Dave Siegel that you're now involved with a little bit. The reason I wanted to start this company with Dave is like there's no one on the planet more passionate about tea.

49:24The fact that David Siegel, who created David's Tea, was not running a tea company in the modern world was ridiculous. All he cares about is tea. Of course he should start a tea company. He already started one because of some interpersonal issues. He ended up leaving his company. Of course he should start it. If you are deeply passionate about something, I wear a James Purse t-shirt every day, and today I'm wearing all James Purse. Of course James Purse is successful. because no one thinks about GSM counts or rib more than he does. No one thinks about Japanese cotton versus American cotton more than he does.

50:05No one thinks about, actually, these are called the parachute pants. These are his favorite pants. I hung out with him a couple weeks ago, and we both literally walked in wearing the exact same thing. Of course, his pants are amazing because he made these pants for himself. It just turns out that thousands of other people also want to wear those pants. The idea that the people that are running businesses are deeply connected to those businesses and the products they're creating, I think, is a new way to run companies that our parents and grandparents didn't have. Some, you know, go back 150 years.

50:36Some of the bakers truly loved baking. But some of them just did so because they had to survive. My grandfather had no interest in eggs whatsoever. Anytime I tried to engage him on eggs, I got a blank stare. He wasn't selling eggs because he cared about eggs. He was selling eggs as a means of survival. Forced entrepreneurship and passion-based entrepreneurship are very, very different things. And the idea of us, you doing your life's work and me doing my life's work, that is a concept that was foreign to our parents and grandparents. Totally. They did sort of what they had to. Life's work. That's a nice, you know, like, I never said that to my grandfather.

51:14That's a luxury. That's a luxury, young man. You know, wow, aren't you lucky? That sounds like a hobby to me, you know, as opposed to they were rough and tumble. They were like, do whatever we needed to do to survive. If it was eggs or it was garments or whatever, you know, we're sitting in Montreal right now. And about 10 kilometers north of here is the Chabanel Garment District. The Chabanel Garment District is an iconic area. It's probably four streets by four streets. and American Apparel, Buffalo Jeans, Algo Industries, so many companies, K-Parsuko, more modern companies, Essence is based there now, Moose Knuckles is based there.

51:57It's this tiny little area that so much of the apparel industries that we know today were created out of. Why did that exist? It existed because it was the lowest barrier to entry. The needle trade or the schmutz business, which is sort of the Jewish version of that, the reason you see so many Jewish immigrants go into the schmutz business, the needle trade, is because low barrowed entry. They couldn't go to biotech. Biotech had a high barrowed entry. You couldn't be, you couldn't have no money and start a biotech company or start a pharmaceutical company or start a technology company. But the clothing business, you need a sewing machine and that's it and i it's wonderful that we have that industry that's been built here but there's a lot of people that ended up building those companies that built it because they had no choice as opposed to because they chose to be like james chose to be in this industry you're the second person in the last month who's mentioned him and his shirts i gotta check these you gotta check them out they're yeah they're great i want to come back to mentors for a second so seth godin is one of your mentors you have a personal board of directors in different aspects of your life, whether it's relationship business, storytelling, walk me through some of the categories you have and some of the people that are in those categories.

53:16One thing that I think a lot of people and I myself made this mistake was that you end up, when you think about the idea of a mentor, you end up thinking about the 360 of the mentor. Like I'm going to emulate everything about the mentor. my experience has been that back to the spiky object thing that any of them any mentors that anyone watching or listening have in their lives they probably are really good at something look really good obviously they wouldn't be a mentor otherwise but they're probably lacking in other areas entirely and i had a mentor early on in my life that ended up convincing me to go to law school and i won't say his name now because i'm about to say something fairly uh well he won't mind, but I won't say his name anyway.

53:56He's on the head of convinced me to move to Ottawa to go to law school. He convinced me to go to law school to become a better entrepreneur, not become a lawyer. Great man. I've known him since I was a child. I was actually years before I was the ring bearer at his first or second, I think his first wedding or second wedding. Which brings me to my point is that like, this guy's an amazing career mentor and helped me more than almost anyone else. He's not what I would call a marriage or relationship mentor. He's on his third marriage now. And he's happily married now, but he's on his third marriage.

54:29If you try to cargo cult everything about one particular person, you're going to adopt all their good stuff and all their bad stuff. Instead, it's much easier to figure out what are the couple things I want to get good at. Entrepreneurship, being a great dad, being a great philanthropist, a great DJ. I want to be a great tea entrepreneur. And then looking at who's really good at that and ask them specifically to help you with that narrow category as opposed to being a lot more broad. The other thing that happens is that there's a timeliness to these mentors, meaning someone that was your mentor.

55:07I don't know if you've ever had any business coaches or any coaches in your life. Yeah. So I think I have a great coach in my life right now. It's probably my third or fourth coach that I've had. one of the things I think about coaching and business coaches in particular is at some point you end up hearing a lot of the same stories or lessons or tools meaning they have this wonderful toolbox and part of what you're paying them to be your coaches for them to open their toolbox and show you all their tools and you can adopt some of them for yourself but eventually you've seen the entire toolbox and that's a really good time and it's not a negative thing it's not a criticism it's a really good time to sort of move on to the next coach the same thing goes with mentors that I don't think, with very few exception, there's probably not going to be any one mentor that's going to be your life mentor in perpetuity.

55:53Because ultimately, you are going to change. They're going to change. You're going to want some new perspectives. But one of the things that Lindsay and I did before we got married was we began to look at the couples we knew, most of them meaningfully older than us, and say, who do we think has a really good relationship, a really good marriage? How can we kind of emulate that? and we didn't say anything to them at the time, but then after we got married, we began to nonchalantly start spending time with them, like double dates with them, and kind of seeing how they interact with each other and what their style was with each other, and we ended up developing kind of these relationship mentors, and we ended up developing parental mentors, and it's been awesome.

56:37It's been this incredible thing, and some of these people that are sort of quote-unquote mentors are famous people. Lindsay and I recently created our family foundation, and we want to have a real impact on our foundation. I got a chance to meet David Rubenstein, who created Carlisle Group. And I interviewed him for Big Shot, which is my little Jewish podcast archive that I have with David. And David Rubenstein talked about the rules of how he does philanthropy. So as an example, he talks about, like, he'll only write a big check for an organization or a foundation or a charity where, I'm going to get these kind of wrong, but effectively it's the project wouldn't start without him or the project wouldn't end without him, where he can see the efficacy of the investment in a 10-year period and it's deeply personal to him.

57:27And so he sort of puts up this rubric and if it fits those categories, he's in. He'll give, in David Rubinstein's case, he'll give like$10 million or$100 million. So I began to ask David about philanthropy well after the interview happened. Tell me about this and how you look at that as well. I'm not necessarily sure David Rubenstein is a mentor per se, but he has helped me shape my own understanding of philanthropy. So he's sort of one that's quite famous. But we also have some friends here in Montreal who are not well known. No one knows them. They're very quiet philanthropists. But the way they do it is kind of strange.

58:07It's all about like some people talk about impact investing. They kind of take this entrepreneurial approach to philanthropy, meaning they'll be very precise about what they donate to. So they'll walk into a hospital and they'll say, why is there a lineup here? And the foundation people at the hospital will be like, well, unfortunately, there's only one machine. And this is very popular. This is a cancer screening machine. They'll say, great. How much is a second machine? They'll be like, it's$2 million. Okay. Do you have capacity for it? Not really. What do you need? Well, I need a radiologist for it.

58:34Well, how much is that? And then these people will sort of go away and they'll come back to the hospital literally a week later. They'll say, great. We figured out that you need a radiologist, you need a machine, you need a new location. You all seem to change some power to sort of for this all to work because you don't have enough power supply here. So we think it's$4.5 million. We're going to go and raise$4.5 million for this exact thing, this precise thing. And lo and behold, six months later, you walk into this hospital, the machine is there. There's no lineup anymore and everything is solved.

59:01So they are not doing this sort of blanket philanthropy. They're being very precise. And so we've been able to kind of find these different people in these different categories. And it's amazing because you get this cheat sheet for anything you want to get good at. I started DJing again recently. And so I began talking to, there's this amazing shop here called Moog, M-O-O-G, Moog Audio. Amazing, like legendary music shop in the world, but certainly here in Montreal. all and so I started going to the shop more often hanging out there and like listening to the DJs and ended up meeting one of the DJs guy Alex who runs the shop and asking him like so how do you think about like when you beat mix what do you do is it eight beat counts or using new technology how do you think about fading um there's there's something called um stems in DJing so you take a song there are three stems there's basically the drum bass like the beat there's the vocals and there's the instrumentals and I was like when I was DJing we couldn't necessarily identify or isolate stems.

59:56I was like, but you seem to be doing that a lot when you're DJing. And I listen to your SoundCloud stuff. And he's like, well, here's how you can do this in every category of your life. And it doesn't have to be these famous people. It can be a random person you end up meeting at the DJ shop. And it's been it's been amazing for me and Lindsay. It's been amazing for my own life. But I will say that a lot of a lot of people try to emulate something like that. and there's this cringe factor involved that I find that most people can't get over. And the cringe factor is often, I have to send a lot of text messages and a lot of emails and a lot of, even now that some people know me, I still, like I have zero cringe in my life.

1:00:43I don't worry about cringe at all. I never feel that way at all. So if there's someone that I really want to get, you know, intro to and start working with and start getting mentorship from, I will go full on and I will never be disrespectful, but I have no issue with rejection whatsoever. And I think that's the largest blocker of why more people don't create these personal boards of directors. Let's go deeper on that for a second. I think you hit on a really key point, which is I kind of think of this as like most people don't want to look like an idiot in the short term to look like a genius in the long term.

1:01:15and because they're unwilling to do something where somebody might say no or it might make them look you know you want to start skateboarding well you you've got to get on a skateboard to actually start skateboarding but you're going to look like a fool for the first few months or maybe weeks or years or whatever but you're unwilling to do that and so you never get better at these things i have very high cringe pain tolerance whatever you want to call it i have no issue with that whatsoever i think that there is this this gets easier also with age i find the older I get, the less I really care about that stuff.

1:01:47But yeah, I think most people are not willing to look stupid for a period of time. I think the other thing is that I think about this all from the concept of entrepreneurship. In my office here in Montreal, Shopify office, I have the original screen print that Ben Francis used to create Gymshark. It was a gift. It's a super meaningful gift that he gave me. I love it. I have it hung up in my office. Part of the reason why it's up there is because I think that it's an amazing gift and Gymshark is this homegrown success story on Shopify. It exemplifies everything we stand for. It's incredible. But the other reason I have it up there is because what most people don't know is that that was not Ben Francis's first company.

1:02:24Ben Francis actually had a bunch of failed companies before he landed on Gymshark. And I think about this idea of this cost of failure, not just from entrepreneurship perspective, but in general. You have to basically figure out with anything you're doing, what is the cost of failure here? If the cost of failure is really high, you really have to think about it. You have to sort of do a little bit of like the math of is the benefit of success worth the cost of failure? And sometimes it's just not. But I mean, for$39 a month, you can build a store. It's not a pitch for shop, but$39, you can build a store.

1:02:58If it works, blow it up. If it doesn't work, try something else. There are still too many people that are apprehensive, that don't want to put themselves out there because of this fear of failure. And I've long believed that getting really, really comfortable with being uncomfortable is magic. It's totally magic. And I wasn't always good at that. I don't think you can be born with that. I think you can learn that. I think you can learn resilience. but I don't I don't know anyone I admire who's had success who has not gone through that period of making kind of looking kind of dumb and if you've watched the first interview you've ever done me oh god yeah look at that I wouldn't listen to the first I think like 20 or 30 of them I wanted to get a catalog and then I wanted to listen to them sure and then I went for like a really long run and i started listening to them and i was like oh my god and it's like i should have asked this follow-up why did i phrase it that way and like you i'm incredibly hard on myself came back went through every transcript and like i was like i want to get better at this for everybody else but yeah there's no secrets to why you've been so successful in my in my view i've known you now for a number of years you you simply out care other people and i think that outcaring thing.

1:04:50supersedes I think I can help that 50 % person get more skill. I'm not sure I can change their level of ambition. I think you can change ambition, but I think like sheer, innate, deep-rooted ambition, which call it care, whatever nomenclature you want to use, I think that is a superpower. And it's also the reason why when I meet someone, they say, what do you think I should do with my life? I often ask them, what do you do for fun? because often the what you do for fun question ends up turning into i really want to be a fashion designer and i'm like you should go be a fashion designer even though you've ever done it you may not have the raw skills you will learn those skills but you seem to really care about this thing you're probably going to be good at it is there a difference between who cares the most and who wants it more or the like how do you see that in your look at them the same in my view um usually high care comes from high intent or high uh an elevated level of desire to succeed i'm trying to teach my kids that right now i i spent a lot of you know this is kind of weird but i kind of wish i had kids pre-ipo rather than post-ipo why i think whatever success that i've had and success of of things i've been involved with they are more meaningful to me because obviously i know where i come from i know how hard it was but i also see how lindsey how my wife sees my relationship with things i've done in particular with shopify lindsey has great a wonderful emotional connection it's shopify for lindsey even my wife is not just a company she remembers you know those early days she remembers those like being on top of Tucker's Marketplace in the Byron Market.

1:06:46The office stunk like the buffet restaurant and struggling. This is pre-Series A even. And I like that. I love that she knows that. She knows how meaningful it is because she's seen the entire journey. My kids were born in the last eight years or so. They kind of only know our life being pretty good. Our life's changed post-IPO. I don't think that's a secret. But financially, my life changed. And I don't take it for granted. But I kind of wish they knew what Lindsay and my first apartment looked like in Ottawa, Canada. And how gross it was. It wasn't gross because it was dirty. It was just a nice apartment.

1:07:26Because we couldn't afford anything else. And so what Lindsay often tells me is just like, yeah, the kids didn't see that. But tell them those stories. And so I do. I tell those kids. I tell my daughters the stories of those early days and how scary it was. And we didn't know if it was going to succeed or not. And I want them to see that. I think I don't want them to think any of this came simply because it was fate or just kind of happened or, you know, I mean, luck plays a role here. But this was sheer grit and willpower. And it still is. part of the reason why I like starting these small projects like Big Shot or Firebelly is I want the kids to see that I want the kids to see this thing that you know that first episode of Big Shot we did was it was Charles Bronfman it didn't do very well I wasn't very good at it I wasn't a good interviewer I didn't know what questions to ask Dave and I were kind of awkward fumbling along together and Bailey my eldest has sort of memorized most of that episode and now she watches that.

1:08:31They love watching Big Shot. They also watched the most recent episode, Bobby Kotick, who built Activision Blizzard. We put that out last week. And I love watching her see the difference in style and the articulation because I want her to know that, like, all the things she wants in her life, she can have, but it won't be easy. No one's going to give it to her. And it's going to kind of suck at the beginning. Go a little bit deeper on that because you know what came to mind when you were saying that is this conversation i have with chris bosh and the thing about that entire interview that sticks out with me even to this day is he told me this story about how growing up they had nothing and he loved to play the private school kids yeah beat them because they're so entitled he's like they had air conditioning they don't know what it's like to work out in a gym when it's 110 degrees yeah i have no idea and i love to go in there and i love to win and he then at the end he sort of like twisted this around he's like now my kids are those private school kids it's really hard i mean i don't want to create artificial scarcity or artificial you know I don't want to create things that don't exist for my kids and pretend like our life is different than it is.

1:09:57This is where Lindsay's really great. Lindsay's a psychotherapist, so she thinks a lot more about this than I do. But she'll often remind me that, like, it's not what you say. It's what you do. It's what they see. And so, you know, for example, we're fortunate to have some help at the house. But, like, Bailey makes her bed every day. Bailey puts her dishes away. now that's very different than you know what chris bosh said about like the you know where how he grew up but there's a certain level of like respect that we show the people that have helped us there's a certain level of care that we show the people that are around us i'm not sure that i can invent some sort of some version of poverty for my children i think that would that would part of why i work harder so my my my kids can have you know less of that multi-generational trauma that I've felt.

1:10:44But I want them to be grateful and hardworking and have conviction. I want them to work on projects together. I want them to fall on their face when they haven't done the right thing. And I want to celebrate them when they work really, really hard. The type of school my daughters go to now was the type of school that my mom said she couldn't afford to send me to.

1:11:08And that's one of the reasons why I worry about, am I doing all the right things? am I a great parent, am I a great father I don't know that I am I like Sundays here at Shopify we have something called Builder Sundays so we open up the offices it's done in Montreal and Toronto so anyone in the city that's an entrepreneur can come in and work from here and I come in almost every Sunday and often we'll bring the kids, usually I'll bring Bailey with me and I'll just walk around and I'll talk to people and ask them how they can be helpful and stuff and I see Bailey watching me do this? And she's like, well, like, what's that person doing?

1:11:44I was like, well, that person's building a Shopify app. And she's like, well, what did you ask? And I was like, well, he asked, you know, once the app is built, how does he get people to use the app? And she said, well, what'd you say? And I said, well, you know, like, make sure the app adds a lot of value. And then the first five people that installed it, like call them and ask them how you can make it better. And if you've made it better and they're happy, ask them to write a review. And, and so I'm beginning to think that parenting is not that complicated, that we complicate it. We try all these devices and and and these techniques and these programs and all these sort of things but ultimately they're just watching us and and and they're going to they're going to copy and they're going to emulate the behavior they see from us and if we're respectful they're going to be respectful and we're hard working they're going to be hard working i think part of that back to that family motto of how you do anything is how you do everything i don't actually care what my kids end doing professionally, whether they're entrepreneurs or they're musicians or they have a trade that they work on.

1:12:47I just want them to have intentionality. I don't want them to do something just because, well, this is kind of where life brought me. I hate that. The opposite of how you do anything is how you do everything is this other term that I hate. I hate when anyone says it, which is it is what it is. I don't believe that to be true. I hate that expression. It is what it is. What does it even mean? It is what it is. It means that like somehow you were just this thing happened. You're accepting it. You can change your own fate. You can change your own life. You can change everything about everything around you.

1:13:18I want my kids to see that that is not the way to live. That living with great intentionality is important. And jury's still out on that. We'll see how they turn out. But so far, they're pretty good kids. I think you're really hard on yourself. What does high agency mean to you? I don't think you have to have the glory without the high agency, meaning I like people that take deep responsibility for things. This idea, you know, back to expressions that I hate. Well, that's not my job. That is an expression I loathe, especially like in a setting of a company. I just I don't believe that. I don't think that's and frankly, at any stage of company.

1:14:00I mean, there's sometimes where like that literally is someone else's job. I get that. But high agency is someone that sees a problem and says, I'm going to fix it, and then fixes it themselves. That they take, they put themselves into the role of single-threaded owner, responsible person. I take high agency in everything that I have. It's actually a great term. I actually don't think about that term that often. I love that term. I think the people I admire most all have high agency. They see something, they take responsibility for it, which means that if it goes well, it's their win. If it doesn't go well, it's their loss.

1:14:41But they have the levers in their hand. They're able to maneuver those levers however they best see fit, and they're willing to accept the consequences of those results. funny anecdote tying together parenting and uh it's not my job which triggered this memory i mean i once asked my kids i think they were seven and eight at the time i was like okay go clean the bathrooms in the house and they knew how to do it so asking them seemed appropriate and my eight-year-old looked at me and he's like uh that's not my job tess who was our house you know the lady who cleaned our house every couple weeks he's like that's tess's job and i remember just sitting there for like a brief second and i was like what do i do in this situation so i like picked up my phone i called tess and i said tess you don't have to come in tomorrow don't worry about it you're gonna get paid and the kids have volunteered to do all of your all of the stuff that you normally do for us amazing and so i made this list and it was like long and i was like you can't do any ipad no movies no anything until this list is guess what now it is your job and not once since that day have they ever pushed back when i asked them to do anything around the house or help out they're like no problem yeah of course i think it's looking and it's not that your your son was saying something wrong no he actually thought it was 100 which is why again like it's this crazy paradox like we we work so hard to give our kids these great these great lives and make their lives better but ultimately we don't want to deprive them from the things that actually will give them their own satisfaction later on i have uh you know without sort of naming names i have uh two two people that are close to me that are both third generation kind of big families meaning you know each of their parents i think were billionaires okay very wealthy people um and in both cases so I know the third gen in both cases one of them is one of the hardest working people I know the other one is not at all like the opposite super laid backs and they're both very happy people they're both wonderful people but it's fascinating to me how both of them are third gen yet completely different and it's all about the values they set one really wants to prove that he was able to, you know, he benefited from the past two generations, but he's going to make his own mark in the world.

1:17:21Making his own mark is deeply important to him because he wants to have personal meaning, personal accomplishment. The other one is like, look, I basically won the lottery. So I'm going to, I'm going to enjoy life more than anybody else because like, I don't even know how this happened, but I'm going to enjoy it. Neither of them are wrong or right, but I'm fascinated by how parenting translate into ambition and translate into meaning and conviction. I think a lot about that. I don't know. I definitely am a little ahead of you with the kids' ages, but I definitely do not have any answers to that.

1:17:53One of the only pieces of advice Charlie Munger gave me about parenting over dinner once was the parents that try to artificially impose a different lifestyle on their kids than they are living uh and he gave an extreme example of a guy getting like chauffeured to work with a driver and then telling his kids to get a very terribly monger version of this oh mcdonald's right and he said that that does nothing but cause resentment yeah because then again now you're creating something artificial it's not it's not it's not real yeah i want them you know i i want them to i want it to be real i see it actually i set up my my new dj booth um in my house and every time i dj i can almost count it like within 30 seconds both kids will come up and say i want to dj too amazing i could have bought them dj equipment for themselves that's sort of a i don't know like a rich dad thing to do like i'm djing i got you dj coming no instead they see how much fun i'm having djing and i love djing i put it on instagram stories every sunday a couple different mixes that i do but they watch how much fun i have and then they want to do it and now they're asking their DJ equipment?

1:19:02Of course, my answer is, well, you should save your money. You can do chores and your birthday money and all that. Eventually, you can save your money. I will go with you to the store. We can buy DJ equipment for you. But I never would have been able to inspire them to think about this thing called DJing and music if I was just throwing it at them. Rather, by showing them how much I enjoy it, they seem to gravitate to it way more. I love that. I want to come back Back to something we talked about earlier in terms of trying to be great and intentional at everything you do, which means you have to pick and choose what you do.

1:19:40One of the things that you've talked about in the past, we've never talked about, but you've talked about in the past is sort of your calendar management system for prioritization. And I often had this theory before I heard your story. And I, people would, when I ran a team for the government, people would tell me their priorities and I'd be like, show me your calendar. Don't, don't tell me your priorities, show me your calendar. Talk to me about how you use that to set priorities and then audit that you're spending time on the right things. Well, the audit's an easy one because I, I'm fairly compulsive about auditing my calendar once a quarter.

1:20:19And I do that with my team here at Shopify. I also do it with Lindsay, with my wife. So like Lindsay is also deeply involved in sort of in diarizing my priorities. I calendar everything. I calendar this interview we're doing together. I calendar what I'm going to do between now and our dinner tonight. I calendar our dinner tonight. I find that putting everything into my calendar, even though it sounds ridiculous to have like walk with wife or meditation. I want to meditate more. I have anxiety. I'd manage it really well. But part of how I manage it is through meditation. You want to see my priorities?

1:21:02Show my calendar. Every morning, there's a calendar. I do eight minutes a morning. There's a calendar reminder about meditation. It's in the calendar. It's permanent. It's always in there. It's been there for years. so I think most people use their calendar professionally but they don't want to use it personally it almost feels I don't know it feels icky to them or it feels too overly prescriptive and and formal it's not me everything is in there it's really really important years ago someone sent me the Paul Graham makers versus managers time which effectively is that you know the way that at least Paul Graham describes it is that he's got these blocks called manager's time, like they're 30 minute blocks, and he has maker's times, which are a lot longer for deeper thinking times.

1:21:48So I do that quite a bit. And I try to kind of bundle my meeting days on certain days, usually Monday, Wednesday, Fridays, and then more of my like, my maker days, Tuesdays and Thursdays, where I can have long form blocks of time to do thinking to do writing, if I'm writing a speech, or I'm now preparing for Shopify summit, which will bring a whole team together, or I have to write my keynote. I'm just, I'm intentional about that stuff. I don't think there's any other way to do it. What I also find is that I color code everything. And so what I can do by color coding everything is that I can see like, um, last night, Lindsay and I had dinner with another couple.

1:22:21It was really great, but that was color coding purple, um, sort of social dinners. And when I'm looking on a Sunday night reviewing my week, and I see a lot of those social dinners, I'm like, I think this week is a little too heavy. And so now I can sort of adjust. Okay. Like I'm okay to have one social dinner during the week. I can't have two or three of those. I'll just like, I need to preserve my own energies as well. The color coding thing is really helpful because you can see visually that like where's my time going? Jesse Itzler, I don't know who you're Jesse. He's the founder of Marquis Jet.

1:22:52He's married to Sarah Blakely who created Spanx. But I did an endurance race that he created called 2929. It's called Everesting. Effectively, there's like 12 of them. You climb these mountains and you emulate climbing Mount Everest, which is 29 ,000, 29 feet. And I did the Everesting race last September. I'm doing it again this year in Mont Tremblant. And so I got a chance to meet Jesse and spend some time with him. And also kind of I now follow him on social media. And he's got this thing called the Big Ass Calendar. It's literally a big ass calendar. And part of the reason why it's actually sells it on Shopify.

1:23:26It's pretty cool. But the reason why he does it is because it's in his office on the wall. and he can see literally 365 days, everything visually. And what he starts doing, which I really love, and I've tried this a little bit, although I don't have it printed out, is he'll start the year by saying, okay, what are the most important things? So he'll put in like school graduations or birthdays or earnings calls or whatever is important to him. And then he'll add to it, okay, trips, add the trips in. And once you actually have everything visually in front of you, now you're able to sort of take a stab back and say like, okay, now you see my calendar.

1:24:00do you see my priorities if i want to if i want to get better at like running where's the running stuff in there if it's if it's sporadic it's obviously not a priority and there is this you know i think lying to yourself is like it's kind of insane that that's really where stress comes from i find i think that stressing stress like comes from like when like fundamentally your mind and like your body like are just not aligned very well and when you look at something and you keep saying i'm really going to get into tennis in 2026 and you're looking at your calendar and there's like not much tennis on it you're like obviously it's bullshit like i'm lying to myself it's not that important and i i think the calendar especially like the great part about a digital calendar is you have it always on you it's always synced everywhere your ipad your desktop your laptop your phone you have it everywhere available to you can add people to it as well it just makes everything so much easier now now for the downside it can also be a burden i'm taking the kids um It's a long weekend here, and I'm taking the kids, and Lindsay and I and the kids are going to New York this weekend.

1:25:02And we want to go see Broadway shows, and we're huge foodies, one of some great restaurants. Taylor Swift's new favorite restaurant is going to be called Corner Store. I want to go there. And my wife and I want to do a spin class and all that. So if you were to look at my New York calendar coming up for this weekend, you would look at me like, dude, you're missing out on life. There's no room for serendipity. There's no room for you just getting lost in Central Park. There's no room for you just turning down the wrong street in Soho and finding a really cool boutique at a great sneaker shop. There's no room for, you know, I don't know, your kids like you taking a nap randomly.

1:25:41And that's true. That's not me. I'm not the sobriatic guy. I'm not the serendipity guy. I know who I am. I'm the type of person that wants to see my calendar for the next four days and be like, it's all on there because that's what gives me joy. And for other people, they would find it to be completely anxiety inducing. But that's not who I am. So I think being honest about the types of things that like you're into and how you want to live your life and then reflecting it and manifesting it in a way that like actually allows you to create these guardrails is super, super helpful. I appreciate that.

1:26:14You do that? Yeah. I don't calendar sort of like go for a coffee. But, you know, every morning, 9 to 12 is usually blocked off. There's no meetings. I tend to schedule things around energy. So like things I don't appreciate or like doing as much tend to go in the afternoon when I'm lower energy than in the morning. I'm glad we're recording this in the afternoon. Yeah, that's not what I meant. I mean, like lawyers or accountants or like reviewing things, you know, those aren't high energy tasks for me. But I've never thought about sort of like starting the year and putting in the most important dates first.

1:26:49I don't really use color coding to the extent that i probably should and this helps on the visual side of it like why is there so much green this week you're like what's green oh yeah green is like whatever you know uh extracurricular like there's too much green like you know i i something's wrong here it just allows you to just have the like holy shit moment something is off here there's no balance here for me my calendar needs to look like a rainbow if it looks like a rainbow i know that I have this balance that I myself am looking for. I love that. I want to come to AI and how it's impacting the workforce that you guys have, how it's impacting other things.

1:27:28But let's start with, Toby put out a memo. And we've talked about this sort of like texting. And so the memo came out and he put it out there. He said, basically, if you're not AI by default, you're in a lot of trouble. You know, talk to me about that. He actually said something slightly different, which he said that if you are not using AI reflexively, which is a very interesting term to use, right? By default is one thing. Reflexively is different, meaning in your jobs, everyone that's listening and watching, when you have a problem that you're working on a challenge, a project, are you reflexively thinking about what tool exists right now that I can pull down to help me do my job better?

1:28:07And that's, I mean, that memo obviously got leaked. It was an internal memo that he sent to the whole team. and he's done this before i mean you know historically i guess quasi famously he did a memo about shopify mobile that like we were still living kind of in like the desktop world and it was clear that e-commerce in particular was moving more to a mobile device that more traffic was coming in but shop it was still building kind of in this like web browser based you know desktop world and so he wrote this he wrote a memo to the company and eventually it also got leaked so maybe the story here is that a lot of things when you're a big company getting leaked but it was an important memo because it was a reminder to the company that like look this isn't just some random new tool this is a new type of programming language this is a fundamental paradigm shift in the way we all work and whether you are a storyteller where before I'm preparing for something and I'm like hey I just I want to check a couple things like here are the stats that I have I can throw it into I like to use perplexity or I actually really love Claude for projects on personal abuse, Claude.

1:29:11But for Claude, what I do is I have like I have a project for like health and wellness. So every blood test I have, I upload there. Actually, Toby kind of showed me how to like how to create these projects in a really interesting way that has these great triggers. And so somebody comes in over email from my doctor blood test. I put it in there or I'll have one around speaking. So I've uploaded every one of my transcripts of speaking. and so I can write something and I can put it into Claude and I can say, from a tone perspective, does this sound like me? Like what parts of this doesn't feel like my other talks?

1:29:41Or have I told this story before? It's this amazing tool. So I think what he does so well is he is the Overton window shifter and he kicks that window hard. And so he just wants to make sure that at Shopify, if you work here, you are within the, like the origin window of AI, like being reflexive is deeply met in the culture. Something else happened. Um, in February of this year, I had our, um, we did our Q4 earnings call. So Jeff and I are CFO on the earnings call. And then there were a bunch of reports, the analyst reports come on after the earnings call and stuff. I think we have like 46 or 47 an analyst covering Shopify.

1:30:25And a bunch of the reports mentioned on the, actually criticized me for saying, and also we were surprised that Harley did not talk more about AI. And I was like, this is weird. Like two or three reports came out like that. I was like, this is strange. I listened to the call again. And I listened to a lot of other calls too. What I realized was, I get it. All these other companies that reported around the same time as we did they basically spent 50 percent of the call talking about ai our ai investments what ai's to do for our customers it was like if you sort of word clouded the earnings call scripts by far ai would have been the largest cloud and it wasn't for us it was i mentioned i talked about shopify magic and all that and it it dawned on me that the reason that we were i was criticized we were criticized for this was that like i think a lot of companies are very hand-wavy about ai like ai is going to change our company and and it's going to like you know uh it's like that poster of like an eagle with leadership underneath and people like what's our culture it's that poster no that's not like that's a stupid poster culture is like what people do how people feel what what happens when no one's watching what is what does the team do that's real culture putting a sign up is completely superficial nonsense.

1:31:44Well, a lot of companies are sort of talking to the AI right now in a similar sort of superficial nonsense kind of way. Ultimately, if you think about the mission of Shopify, it's we want to create more entrepreneurs. We want to make entrepreneurship more accessible. We want more people to use it to whatever their version of success is. Maybe it's to be the youngest billionaire in the UK like Ben Francis and Gymshark, or maybe it's just to afford hockey equipment. But we think that entrepreneurship allows anyone to do that. It's the great equalizer. The unfair advantage that, like, unfair, like, big unfair advantage that large companies have over small companies is headcount.

1:32:28That they have a lot of people. And so they have a lot of people doing a lot of different jobs. as easy as we've made entrepreneurship there's still that there's still a resource constraint if you are a one man or one woman or a one person operation you don't have a lot of different teams what we think is so fundamentally game-changing and and mind-blowing about ai is that we are actually one of the companies i think that's best position to utilize it to create this like step function advantage for the people that you shop especially the small businesses this idea that we don't have an ai product but rather ai is built all across shopify i think is absolutely incredible um on big shot i interviewed mickey drexler mickey drexler ran the gap for 20 years you know mickey yeah have you had him on the show yeah okay amazing guy as you know he can tell stories forever uh so mickey told me that when he was at The Gap.

1:33:30The Gap had these like massive merchandising teams and product photography teams. And as he was telling me this, the first thing I thought about was, oh my God. If you compare Mickey Drucks for running The Gap in 1997, 1998, doing billions of dollars, a one-person operation at their mom's kitchen table right now on Shopify who needs to write a product description, who needs to do product photography, I suspect that today they can have a higher converting, a higher, a highly optimized or higher optimized product description and a better product photography taken than Mickey's 300 person team. That to me is like the ultimate, that's what, like, that's why AI matters to Shopify.

1:34:18It's not about the hand wavy, all this stuff and earnings call word, word cloud bubble stuff. It's about can we actually even further bend the learning curve and the barren entry into entrepreneurship? Nothing quite does this like AI does. Now, it doesn't mean you can effectively set it and forget it, but it just means that it's going to be a huge mass advantage. And I think the way that we're doing it is not simply by having one AI product, but rather literally embedding it across all of Shopify. I think that's going to be. From a trajectory perspective, you will see a pre and a post trajectory of business growth, particularly small business growth, because of AI relative to almost every other technology that came out.

1:35:02I mean, it is so substantially valuable for small teams because it puts so much of their – it gives them so many more resources in a way that they would never have unless they had bigger teams. And ultimately, if you think about like as a consumer, you are buying a T-shirt. You want to buy the very, very best T-shirt. You don't really care if the T-shirt company has 300 people or three people. You care about the T-shirt itself. But unfortunately, that 300-person company historically was able to get in front of more customers because they had merchandising teams and marketing teams and product photography teams and all types of other teams.

1:35:37But now that three-person team can actually do as much as a 300-person team. In fact, maybe they can do it better. and I think that is going to be remarkable. So I think from a Shopify perspective, I think our merchants will get a lot better and grow a lot faster because of it. But I think the companies that are able to adopt, and this is really the crux of the, like everyone was surprised by that memo that Toby sent out. We were not. Like most people at Shopify were not surprised by that. It was the most Toby memo. It was like, I want to be clear. Everyone's talking about AI, but what does it really mean?

1:36:09It means that if you work at Shopify, the expectation is that you use it reflexively. The expectation is before you go and try to hire another person for your team, you ask yourself and you test whether or not some sort of AI tool can actually do it better for you. And if it can, that's what you should be doing. I mean, the teams and the companies that embrace that are going to be far more successful than ones that adopt it with some, you know, mediocre energy. I was talking to my kids the other day and I was like, you have a thousand employees at your fingertips. Yes. And they were like, what do you mean?

1:36:42It was like all these GPUs, they work for you. Yes. They do exactly what you asked them to do and they do it better. For 20 bucks. In a lot of ways than most humans do at this point. A hundred percent. And especially with different models coming out and evolving. That's right. It's fascinating to me. What do you think the impact will be on Shopify in five years? Like internally, not for your merchants, but like, do you need 10 ,000 employees? Do you need like, how does this change the dynamic? I mean, in terms of size of the company, I think the size of our company right now and the shape of our company right now is really good.

1:37:17Like, we are very happy with the size. It means we can do more with the same amount of people. It means we can go into new areas. It means we can build faster. I think not just for Shopify, but I think the companies that are going to embrace it, not utilize it, but truly embrace it and make it part of their daily flow. I mean, look, we talked about schedules and prioritization before. once a quarter when I have time I go and look through my calendar I can now create a very simple like agentic tool that basically looks my calendar every week and on Sunday it says dude you got too many social things or dude you got too many one-on-one meetings or like whatever it is I can be all the things that I want to do in my life I think can be made better for that one of my mentors is a guy named Aldo Ben Sedun Aldo's 85 years old he was a Moroccan immigrant to Canada.

1:38:06He built Aldo Shoes. He's, you know, he's built a multi-billion dollar company. And Aldo and I were giving a talk together at, he just gave a bunch of money to McGill to create the Benson School of Retail, Faculty of Retail at McGill, which is, I'm involved with a really, really cool faculty. And we're on stage and I said to Aldo, I'm sort of like, Aldo's kind of an old school guy. And I said, Aldo, what do you think of AI? And I was kind of like, it was a bit of a joke. I was kind of poking fun of like the young guy, like the young retail guy poking the old retail guy and aldo without skimming a beat says it's like having a best friend in your pocket this is an 85 year old man he's seen you know he's seen everything he's seen all new technology for the last you know eight and a half decades but even the fact that he can appreciate how much leverage you get with this new technology i think i think is amazing so i think it'll make us move faster.

1:39:01I think it'll allow us to build stuff with smaller teams. I think it'll allow our merchants to make better decisions. I think you're going to see, you know, I'm blown away even pre kind of some of these large language models and AI tools coming out in the last four or five years. I've been, I found it to be remarkable that these companies have started in 2014 and become billion-dollar companies in the last 10 or 11 years. Typically, business does not happen like that. It took decades to become hegemonic, to become the leader in your category. And now you have companies like, I don't know what's it going to do, Viore, Aloe Yoga.

1:39:37These companies didn't exist a decade ago, and now they are absolutely unequivocal category leaders. It's wild. It took them like less than 10 years. Figs completely disrupted. Trina and Heather completely disrupted the hospital scrub industry. You walk into any hospital in North America, maybe in the world, and you look around and see like what most doctors are wearing or nurses are wearing, it's figs. That didn't exist a decade ago. And now they're publicly traded, multi-billion dollar company. So I've already been, it's been astonishing for me to watch from this perspective. Shopify basically runs about 12 % of all US e-commerce.

1:40:12So if you were to think about like, just in terms of size wise, we're like the second largest checkout on the internet, in the US at least, but in other countries, maybe even more so than that. The trajectory of business growth has been so remarkable so fast. 10 years, you go from an idea to a multi-billion dollar publicly traded company. Now you add on this layer of AI, which means you can make better decisions faster. You can make smaller teams way more productive. I think you're going to have another step function. I think that you will have this incredible hockey stick curve of businesses that grow from zero to$100 million in GMV inside of three years instead of 10 years.

1:40:54And, I mean, I pray at the altar of entrepreneurship. And there's been a couple things over the last, you know, 50 years that has made it much better. Obviously, the internet has made it much better. Obviously, things like Shopify has made it much better. But I think, like, this new era where you have all these things stacked with AI, it is the golden age of entrepreneurship. And I'm here for it. I think a lot of people our age are in more trouble than they realize if they're not using it. And I say this because I had dinner with a few friends the other night and this subject came up and I was like, how is everybody using AI?

1:41:30Like, I'm always interested in how other people like you were talking about sort of like putting your blood test results in a project and I'm like, I'm trying to learn from other people. And almost all of them were like, oh, it hallucinates. So I don't use it very much. And I'm just like, wow, like that's. And then they're like, what are you doing with it? And I go on for like 10 minutes, right? Like I'm coding. I haven't done that in like 10 years. I'm doing all these things with it. And they're just like, wow. I mean, you can literally generate a Python script right now in a matter of 30 seconds with OpenAI right now.

1:42:01You can generate, you can build an app in a matter of like, I mean, back to what you just said, that reaction of, I tried it once, it hallucinated. I think one of the things that you have to have if you're going to be successful in this new era of business and actually in any era with all this new technology is you have to be a techno optimist. You have to believe that things are getting so good at such a quick pace that it doesn't matter that it hallucinated, that the next time you use it, it probably won't hallucinate. And I think if you get stuck in this trap of it hallucinated once, therefore I now have scar tissue, I'm not going to use it, you're going to fall behind.

1:42:42It's one of the reasons why one of my mentors has, I think one of the reasons he spends time with me is he loves hanging out with people younger than him, much younger than him. I'm 40, 30 years younger than him. And he used to run one of the largest companies in Canada. He's an amazing man. And I always noticed that, that he's always hanging out with younger people. And I had someone, I said, you seem to like hanging out with younger people. It's like, because you guys teach me stuff. He's like, my friends don't teach me as much. He's like, my friends are in their 60s and 70s. We talk about golf.

1:43:11We talk about whiskey or wine, whatever. But when I hang out with you, Hartley, you tell me about like the new DJ equipment and how like it's all powered by AI. And you tell me about this new stuff. And then he goes one step further. He's like, and he also has friends that are in their 20s. And they tell me about all types of new technology. And I think there is this, there's something, maybe this is one of the great parts, but like one of the advantages of having kids is you see how they're interacting. You see what they're doing. You know, I sent a note over to David, who's the CEO of Roblox.

1:43:38and I was just explaining to them that the way my kids use Roblox is actually, yes, they're playing a game, but rather the game is almost passively in the background. They're having a conversation and rather than looking at each other, they're looking at this game together, kind of playing, but the actual, at least for my kids who are, you know, Bailey's eight years old, Roblox for her is simply a central chat room. It is not actually about the game itself and rather than staring at the person's face on screen as being the main focal point you know the face is kind of in the bottom right corner the main focal point is then in some random game and and rather you know it's maybe and david of course knows this but i was like what you've created is like a social network and like you call it a you know game ecosystem and all that but watching how people are using this technology is is remarkable and uh it's i think if you are a techno-optimist and you're paying attention to all these things that are happening, it is tough not to be incredibly optimistic about where we are and the world we're living in right now.

1:44:43It's amazing. I could go on for another couple hours. I think this is probably a good moment to sort of wrap this up. We always end with the same question, which is, what is success for you? I think about this term, I mentioned a few times, life's work. I think about this term, joie de vivre, which is joy of life, which is a beautiful French term that is, you know, for me, like Montreal is the joie de vivre capital. Um, I want more of those things in my life. I want to do more of my life's work. I want to have more joie de vivre in my life. And I don't want to, I don't want to sacrifice either of those things.

1:45:20Um, I think that's what success looks like. The, the harmonization of joie de vivre and life's work would be, um, that would make me successful. I think that's a beautiful answer. And we'll have to do part two, cause I got a million more questions, but I appreciate it. Appreciate it. Thanks for listening and learning with us. Be sure to sign up for my free weekly newsletter at fs. Dot blog slash newsletter. The Farnham street website is also where you can get more info on our membership program, which includes access to episode transcripts, my repository, ad-free episodes, and more. Follow myself and Farnam Street on X Instagram and LinkedIn to stay in the loop.

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