Shopify President: How To Become A Millionaire For The Price Of A Starbucks Coffee! E245

Harley Finkelstein 0:00 One of the greatest hacks for being an ambitious, hard-driving entrepreneur is- And that's why Kylie Jenner is nothing short of brilliant. Harley Finkelstein is the president of Shopify, one of the largest e-commerce platforms.

Steven Bartlett 0:12 Worth over $60 billion, he's helped scale brands worldwide. And he's now on a mission to help you start your own business.

Harley Finkelstein 0:18 About a month into college, I got a call from my mom and said, "Dad's been arrested, and he's going to jail." College is over, and I was shifted into this survival mode. I had no choice, and it's a very powerful driver. I met Tobi around that time. The initial idea had lots of other competitors. This was not this massive novel thing. We just did it better, and that was how Shopify was born. There's a perception that entrepreneurship is very expensive. That's not true. It's less than a couple Starbucks coffees to go start a business today. There are still far too many people that work at a job they absolutely hate because they think they have no choice. No one had this massive 80-page business plan and then got started. That's not how businesses are created. They're created based on this nugget of an idea, and they're explored, and you get curious about it, and you try this other stuff. And that's how you build companies that change the (censored) world. I wake up every morning encouraging more entrepreneurship, creating tools that help entrepreneurs start, scale, and build faster. That drives me to keep building and keep growing. The stories that we are most proud of are the homegrown success stories that grew to be multibillion-dollar businesses.

Steven Bartlett 1:15 If I gave you $3 million, who would you invest it in?

Harley Finkelstein 1:18 I would definitely put one of those millions of dollars into the hands of a creator who's ... The second one I think would be ... The third one would be someone ...

Steven Bartlett 1:26 Oh, really?

Harley Finkelstein 1:27 Yeah. Those are the types of people that, that I would back.

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Steven Bartlett 2:05 Harley, in your own words, who are you, what do you do, and what mission are you on?

Harley Finkelstein 2:14 Hmm. I've always self-identified as an entrepreneur, full stop. Um, that's kind of the tool that I use to solve every problem in my life and to have fun is always through the lens of entrepreneurship. What do I do? Um, I mean, I think technically I'm, I'm the president of Shopify, but I view my role as being the chief storyteller. How can I get the world to know that Shopify is the entrepreneurship company and invite more people to participate in that? The mission that I'm on, this is gonna sound really repetitive now, but, is I want more people to try their hand at this thing that, that I call business creation or entrepreneurship. And I don't think right now most people consider entrepreneurship as a thing that they can do to self-actualize.

Steven Bartlett 2:56 Well, why, why does it matter if they, if more people become entrepreneurs?

Harley Finkelstein 3:00 I think the world is far more colorful, and I think humans are far more interesting when they commercialize their hobby, for example. I think there are still far too many people that work at a job they absolutely hate. In fact, I would say that they loathe because they think they have no choice. And that was the case for a long time. You go back 40 years, 50 years, not everyone could be an entrepreneur. That is different. And I'm not saying that everyone that has a great hobby should commercialize that hobby. Some hobbies should stay hobbies. But there are a ton of people who work at a job they, they despise. They go home at night, they go to their garage or their workshop or their kitchen table, and they tinker on cool stuff, but they don't share that with the world. If they did that, consumers would get really better stuff that they can purchase and they can use, but those particular people behind those businesses can find their life's work. And this, this concept of life's work is not something that my parents, my grandparents, and my great-grandparents even had in their lexicon. But I think the idea of finding your life's work, I think you have done that, Steve, and I hope that I've done that too. That is a life-changing moment.

Steven Bartlett 4:03 There's, there's gonna be potentially millions of people listening to this now that resonate with what you're saying. They are in situations that are not serving them on some kind of psychological fulfillment level. Um, why aren't those people, in your view, pursuing what their life work is? I'm trying to, like, create some, I guess, some nuance or trying to step into their mindset so that they feel understood. What is the, the, the gap, the Grand Canyon that they need to cross in their mind to get to that other side, which is their life's work? Why don't people do it?

Harley Finkelstein 4:37 I think a big part of it is perception. I think a lot of people perceive entrepreneurship as something that's out of reach, for usually one of two reasons. The first reason is, is financial. They have a family member or a friend or they've heard an anecdote of someone who started a business that was not successful, and ultimately it cost them their entire life. They couldn't ... You know, they lost their house. They couldn't put food on their table. And so there's a perception that entrepreneurship is very expensive. If you don't have money, you cannot start. And actually, I would say that for the vast majority of the time that entrepreneurship or, or business has been available in the world, which is, you know, entrepreneurship or business is about as old as currency, so thousands and thousands of years, the main ingredient in starting a business was capital. And if you didn't have capital, you couldn't start. And I think that's changed, and we can get back to that in a second. The second part is the understanding or the experience or the know-how to begin. And I think that also has changed. I think now you don't have to go to business school. You don't have to, you know, have, have grown up in a, in a, in a home with entrepreneurs to start a business. I think that anyone can start. And so on both those things, I think the cost of failure is as close to zero as it's ever been, right now, like as we sit here. And the second part is, I think that if you try something and it doesn't work, you can try it again. And that may be, you know, your Gymshark, your Alo Yoga, your James Perse.

Steven Bartlett 5:57 I- from a psychological perspective, some people, you know, they often say, "Well, you know, it requires a lot of self-belief."They talk about self-belief and confidence as being this kind of macro force that drives people to, to start. And I was sat here the other day with an entrepreneur who's built multiple companies and been very, very successful, and he was saying to me, he said something to me like, when the, it's actually pain, the pain of his current situation, which drove him to take the, the leap. As it relates to people's, like, psychology and their self-belief and their self-confidence, um, when you're th- trying to get people to become entrepreneurs, what can we do there to get them to take the leap? Is there anything that can be done?

Harley Finkelstein 6:35 I mean, first of all, I think that there's two types of catalysts for starting a business. One is passion, and the other is d- disparity or- or being desperate. And actually, I think entrepreneurs, by necessity, are a big part of m- the, the greatest companies ever being created. The reason I became an entrepreneur, I mean, I, I, I toyed with it as a kid, but, but when I really became an entrepreneur, it was because I had no choice, and that's a very powerful driver. It wasn't about my self-confidence or my swagger, whether or not I thought I could. I had no choice. In terms of, you know, you had Richard Branson on. He has this famous line, "Screw it, just do it."

Steven Bartlett 7:11 Mm-hmm.

Harley Finkelstein 7:11 I think that plays in sort of the passion side of things.

Steven Bartlett 7:14 Mm-hmm.

Harley Finkelstein 7:15 Not necessarily in the disparity kind of things. I didn't say, "Screw it, just do it." I was like, "I have no choice. What am I gonna do right now? I either have to, like, move back home to South Florida and live at home with my mom and, m- mom and sisters," Dad wasn't around, "or I can actually figure this out on my own, and I can pay for school, and I can help support my family." And so, it wasn't about, "Screw it, just do it," that, like it wasn't about self-confidence. It was, "Here's a way for me to actually survive." I think

Harley Finkelstein 7:41 that- I think that matters.

Steven Bartlett 7:42 The role of passion in entrepreneurship, you know, you'll, you'll know that a lot of entrepreneurs, they are so, um, in love with the idea of being rich and successful that they'll kind of try and reverse engineer a passion into this, th- their journey of being rich and successful. So, they'll sit down and say, "What do I think is gonna make me rich and successful?" This happens all the time, you know, entrepreneurs will come up to me and say, "Um, I've got three ideas," and they'll name three random things. "I'm gonna start a hair care business, I might do a coffee company, or I might do crypto," for example. And then y- you look at that and go, like, "Well, it's gonna get so difficult for you at year, in year one, you're gonna quit all of these things." What role do you think passion plays in eventual success?

Harley Finkelstein 8:19 I think you have to actually like the thing you're doing to do it over a long period of time. (laughs) My, my first, uh... When I was 13 years old, um, I grew up in Montreal. I- I'm Jewish. I went to a lot of bar and bat mitzvahs, that thing you do when, you know, 13-year-old kids. Uh, 12 years old if you're a girl, 13 years old if you're a boy. You go to these bar mitzvah parties. And I remember seeing the DJs at these parties on stage playing, I don't know, cheesy music, very cheesy music. But I was just enthralled with them. I thought they were the coolest people in the world because in a matter of minutes, they would take a group of 300 sleepy people eating rubber chicken dinner, and like a minute later, a couple minutes later, they'd be doing the Conga Line. And it looked like magic to me, and I really thought that'd be super cool for me to partake in. And so, there was a passion for me to, "I want to be a DJ." Turned out nobody would hire me 'cause I wasn't really a DJ. I didn't know how to DJ, and I looked like I was eight years old. I mean, I'm, I've always been a little bit short. I'm still short. Uh, but I looked r- I was really short when I was 13. And so there was no way anyone would hire me, and I decided I'd just start my own DJ company and hire myself. So there's some passion to it. When I was 17 years old and I moved from... We moved to South Florida when I was, uh, around that time. We moved back to Montreal when I was 17 to go to McGill University. My dad, uh, was no longer around. We can, we can get into that if you want to. But I, at that point, it wasn't like, "I'm gonna go back to DJing." It was, "Okay, things are really bad right now. Like, Dad's not around. I have too much younger sisters. Mom needs help. What am I gonna do?" And I started selling T-shirts to universities across Canada. I had very little passion towards T-shirts. I like wearing T-shirts, as we talked about earlier. I like, black T-shirts are something that I, I like, but I was not a passionate T-shirt entrepreneur manufacturer. I was passionate about survival. I was passionate about supporting my mom and my sisters. And so, I don't think the T-shirt business was going to be something that I would, I was going to be doing the rest of my life. That was not my life's work. Fast-forward till today, in l- leading Shopify with, with our team, I'm very passionate about Shopify's mission. This idea that more people can be entrepreneurs because of the work we do at Shopify, I can do this the rest of my life if, if the board will have me. Um, so I think there's a time and a place for passion in these things, but I don't think it's the only reason to start.

Steven Bartlett 10:34 Y- y- you referenced a few things there that I thought were quite interesting and that made my mind wander onto, um, adjacent subject matter. One of those is that you're talking there about what's driving us at different moments in our life. One of the, um, conversations I had on this podcast with Barbara Corcoran-

Harley Finkelstein 10:48 Mm-hmm.

Steven Bartlett 10:48 ... the Shark over here in the US, uh, she said to me that her best investments she makes from entrepreneurs, they tend to have some kind of underlying trauma, and, and that ends up being fuel in their engine. So when things get really, really hard, they're driven and in such an obsessive way. And I remember then listening, and I've always thought this, I've always thought that insecurity and shame and these kinds of things are unbelievably unappreciated drivers in people. For better or for worse, it comes with a downside.

Harley Finkelstein 11:15 Mm-hmm.

Steven Bartlett 11:16 Um, do you think entrepreneurs should, and founders, should go to therapy?

Harley Finkelstein 11:22 Uh, I think some should. I think entrepreneurs and founders need to be self-aware. I think that f- fir- that's the first thing. Once they're self-aware and they understand, hey, there are some things going on in my mind, in my personality, in my whatever, my, my, my being, I don't know what, how to describe it, that I need to work on, I think therapy is a hack to get there faster. You can do it on your own, and some people do. Some people do it through books, and they do it through meditation, and they go do, you know, ayahuasca in a, in a, in a desert somewhere. But I think if you have, if you have the means to go to therapy, how could you not? There is someone whose job it is to make you better. Now, I think a lot of people make a mistake where they go to see one therapist and they're like, "This doesn't work for me."

Steven Bartlett 12:03 Yeah.

Harley Finkelstein 12:04 ... and they're like, "Therapy doesn't work." No. That therapist didn't work. If you date somebody and the relationship doesn't work, it doesn't mean you're never gonna date again. It means that was the wrong person for you. And so one thing I think about is whether it's coaching or it's mentors or it's something like a, a, a therapist or a psychologist in your life, or psychiatrist, you need to find the right fit. But if you have the means to do so, it just, it's the greatest hack ever to just know more, to realize more. Is it gonna be painful? Unequivocally. The joke that I have with, with my therapist is I know it's been a good session if I feel worse after than when I did coming in, 'cause sometimes I come into these sessions and I got swagger and I just had a great day and things are going all-

Steven Bartlett 12:39 Yeah.

Harley Finkelstein 12:39 ... things are going my way. Then an hour later, I leave and I'm like, "Oh my God. I'm still like, I'm, I'm still such a work in progress." You know, one ... But, but that's, I think, what we're all choosing here. There's this great ... My favorite poem or, or speech ever is this Teddy Roosevelt speech. The man in the arena. Do, do you know it?

Steven Bartlett 12:56 No.

Harley Finkelstein 12:57 I'm gonna butcher it, but it's effectively like, "It is not the critic that counts, but the m- the man or the woman or the human in the arena that matters." And the reason I love that speech so much is because if you don't want any of this stuff, you, like, you can, you can be a critic, you can be a spectator, but if you're an entrepreneur or you're s- you're a doer or a builder or someone that deeply wants to do cool shit and build something for yourself, for your family, for the world, you gotta be in the arena. And in the arena, there's a lot of fighting, and there's a l- it, it's tough. But I think it's a better way to live. That's the reason why the best articulation of all this is, is this term entrepreneurship, because entrepreneurship is fundamentally you have a problem and you are solving in a way that uses the least amount of resources, but has the highest amount of, of output. And that's the reason why I love entrepreneurship. I love ... We have millions of stores on Shopify. Some of them started because they were passionate about commercializing their, their craft. In some cases, they started because they had no choice. But the end result is they built something that is of value and they've shared it with everybody else. And so, that's what I signed up for, but if I'm going to check that box that this is the life I, that if I w- I'm going to be the man in the arena, I need to acknowledge there's gonna be critics who are gonna try to tear me down, there's gonna be internal critics that are gonna try to mess that up, and I'm still gonna pursue, I'm still gonna move forward and progress. Um, and I think therapy helps with that.

Steven Bartlett 14:22 Wh- what's your relationship like with failure? We talked a little bit about f- the idea of failure at the start of this conversation, why people don't take the leap from th- th- you know, a, a miserable certain situation into an uncertain situation that might make, give them a better life, but what's your relationship been like with failure, because everybody knows to be a successful entrepreneur, to build great products, you have to fail fast. Um, but if you're struggling with, you know, enough-ness, then it seems like that might limit your ability to want to fail f- fast.

Harley Finkelstein 14:49 You know, it, it, it is certain that the more, the more successes you have under your belt, the easier it is to fail, because you feel like if you've had, you know, nine out of ten things have been successful and that tenth has not, it doesn't mean you are a failure. So one thing is, uh, I think separating like you being a failure versus the project or the, the particular thing being a failure is very, very different.

Steven Bartlett 15:10 Which is hard.

Harley Finkelstein 15:10 Which is very hard. Um, Tobi, uh, who, you know, is founder of Shopify and the person I spend most of my time with, um, building this company over the last 13 or 14 years, he has this great line which is that failure is the discovery of something that, that didn't work. And when I think when you use that lens, that failure is the discovery of something that didn't work, which he taught me, that made failure totally different. So now it's no longer about failing. It's like, what did I actually get from that that's gonna make it better the next time? And Shopify puts out a lot of products. We had our, uh, we had some things called Shopify Editions which happened in February where we, twice a year, we basically do almost like the fashion industry. We do like our spring collection and our winter collection. So we do these things called editions where we put out all of the products and features that we've built over the last six months, and we do about 100 of them each time, which is a lot. Not every one of them is going to be a huge success, but some of those will be a complete game changer for our business, but also in the lives of the people that use our product. And I think we have a courage about that. I'm trying to have more of a courage about that myself. If I take on new responsibilities or new roles, am I gonna be a failure? And, and the best example I can give you is for about five years or so, I was Shopify's chief operating officer, and I don't think I was ever the most operationally minded person, meaning I didn't necessarily live in the details. I didn't necessarily live in spreadsheets. But when Tobi and the board asked me to be the chief operating officer, it was a huge, it was a huge honor. I mean, Shopify is such a great company. Wow, like that's what they're asking me. And I worked really, really hard to be the best version of a chief operating officer. And it was only three years ago or so that at some point it was obvious to me that like, that's not really my skillset, but I didn't want to say anything about that because I really believed that like I can figure it out, and I think I did a good job, but maybe not the best job ever. And once I began to talk about, hey, this is probably not the right role for me where I can be the best in the world at, there is this other role which traditionally is called the president role, which is very external-facing. Maybe I can be the best in the world at that thing. I'm not there yet, but I can ... Like, that is a journey I can get on, and maybe I don't have to be well-rounded. Maybe I can actually be spiky, and instead of actually trying to be a well-rounded leader, maybe I can focus on sharpening that point and sharpening that point over and over again. And that's when, you know, I had a conversation with, with Tobi and, and, and, and, and the team and said, "Look, there is this other role and we need to bring someone in who's life's work it would be to be a great chief operating officer." And w- we have that now. But man, Steve, I did not want to admit that I was not the right COO for Shopify because-

Steven Bartlett 17:46 Ego, right?

Harley Finkelstein 17:47 Total. And in- and ego and insecurity. One, I'm admitting failure. The other one is I like this role. It's a very important role. But it was only when I sort of began to be honest about is this the right role for me that I began to say, "Hey, there's this other thing." And I can tell you, I am not a little bit happier now in my current role and, and not, not and, and-... and more, like, it is so much more meaningful for me to have this role today, because I feel like this is really where Shopify will benefit the most from what is my superpower, which is really storytelling. And the company's better. I like it better. The current CEO was so much better at it than I was ever. Everything kind of came, came about, but it took, it probably took too long.

Steven Bartlett 18:29 I, I think that story's an incredibly powerful one, because, uh, I come across people all the time within my own companies, but also just people that will send me messages who are currently in a role. Um, maybe they're being offered a promotion into another role, and because it's a bigger role with a bigger salary, they are inclined to take it. But there, there, there's that missing pause of sort of self-awareness, where you've got your ego pulling you because, "I'm gonna have, you know, higher status in this company. I'm gonna get more pay. People are gonna think I'm cooler and more impressive." But then the most important long-term question is, of course, like, "Am I good at this, and do I, would I really love my life more?" You see that a lot, don't you, when someone gets promoted to a management position and suddenly the group of friends they have are now (laughs) the people that they have to manage. That point of self-awareness is so incredible. Like, I, I re- I reflect on a guy called Pete, who I offered a promotion to (laughs) one day. And he was like, "No, I'm not ready." And I'm, I'm, I'm ... This, uh, this must have been six or-

Harley Finkelstein 19:24 You're like, "What?"

Steven Bartlett 19:25 ... I don't ... What? (laughs)

Harley Finkelstein 19:26 (laughs)

Steven Bartlett 19:26 I'm offering you more money, the chance to become a director in the business. And he'd been with the business for four years at that point. Um, he, he stayed for two years after I even left. He was just like, "I'm not quite ready yet." He goes, "I've still got a lot left to learn, a lot of skills. Um, I, like, really like my current job."

Harley Finkelstein 19:43 Yeah. I like Pete.

Steven Bartlett 19:45 Pete is the happiest guy I know. He has his shit together-

Harley Finkelstein 19:48 Yeah.

Steven Bartlett 19:48 ... way more than I do. (laughs)

Harley Finkelstein 19:49 And not, not only is he happy, but he also, he, he's great. He's got great self-awareness. You know, one change that we recently made at Shopify was we realized that a lot of people, as they were going through the IC track, or Individual Contributor track, eventually it just leads to a manager track.

Steven Bartlett 20:02 Mm-hmm.

Harley Finkelstein 20:02 And so the upward mobility of your career ended up being you actually, at some point, if you're really good, stop doing the thing you're really good at. And so very recently, we put out, uh, sort of a new operating model, uh, for our team, for our organization. And I, I think, I think it's been... I think it got leaked to the press, so it's, it's, this is all public information. But if you wanna be an incredible senior independent contributor, like a senior IC, we will pay you the same rate that we would pay a senior manager. And that if you actually like your craft, whether you're a developer or a marketer or a salesperson, or you're, you're, you're doing, um, data analysis, you're a data scientist, if you love your craft, and I know some people who love their craft, they've been doing it for 30 years, you do not necessarily need to leave that craft to be a manager to get some sort of additional seniority or additional compensation. And dispelling some of that, frankly, like, the bullshit around the only way to be successful is to be a manager, is to lead people. Not everyone needs to lead people. Some people should be a coach. Other people should just continue becoming, like, the greatest player on the field ever. And making that okay, I think, is gonna make Shopify a, a much better company. But one thing you did talk about that, that you sort of raised that, that, that I'm, I, that got me thinking about, like, the self-identity thing is that I think a lot of times for this guy, Pete, Pete may really just be ambitious about perfecting his craft and his skill set. And he doesn't necessarily believe he's ready yet to leave that, because there's still work to be done. I love that. And I think in most companies what you end up with is the Petes of the world, when they say we don't, they, they don't want a promotion, they often get, get taken out completely. "Well, Pete's not ambitious. Pete's not gonna be someone who's gonna be, you know, a real contributor longer term here. Maybe he's lazy." Pete's not lazy. He has a deep understanding ... I don't know who Pete is. This is gonna be hilarious when he hears this.

Steven Bartlett 21:49 You're naming it though, yeah.

Harley Finkelstein 21:50 Um, maybe I do know Pete. But, but Pete has obviously a clear understanding of, "Hey, there's this thing, there's this, this spiky object. Don't make me a river stone. I don't wanna be well-rounded. I wanna be so good at this. And by the way, if I do this, the company's gonna get better. I'm gonna be happier. Our customers are gonna be happier." It all kind of works out. I think most companies turn their employees ultimately into river stones. They say, "You gotta be better here and better there." And I think instead, this sort of T-shaped ... Have you heard of this sort of T-shaped model of skill set? I think the T-shaped is much better, where you can go broad on a lot of different things, but you go deep on one.

Steven Bartlett 22:24 Mm.

Harley Finkelstein 22:24 And that one thing for me is the storytelling aspect of my job, is making sure investors, the public, our merchants, media, everyone in the world knows what Shopify is up to and understands what our ambitions are. And so I'm trying to get really deep on the storytelling, but I also need to understand our API. I need to understand our infrastructure. I need to understand, you know, how we, how we build product and how we get shit done at Shopify. So I understand all those things, because I need to tell, speak to it intelligently and with conviction and with a deep understanding. But I'm never gonna write code, because there are people that, that should write code that are s- gonna be so much better than I'll ever be.

Steven Bartlett 22:57 You, you did, you did nail Pete. I, I remember him saying ... One of the things I do remember in that meeting, I remember where I sat. It's so funny, because it was such a interesting moment for me. I was very young in my career as, like, a CEO, and I, I remember where I sat when he said ... And what I re- recall is he was referencing that he still felt that there was work to be done in his role.

Harley Finkelstein 23:14 Yeah.

Steven Bartlett 23:15 And that he didn't want to move up into this ... Uh, I think it was a global role we were offering him, because he didn't feel like he'd quite finished the work in his current role, which was just in the UK. Um, you referenced spikiness. You know, you said you ... I don't ... That made, gave me flashbacks of a conversation I had with, um, Jimmy Carr, where he said, "We don't need more people that are shit at physics." (laughs) Find the thing you're good at and, like, double down there.

Harley Finkelstein 23:37 Yeah.

Steven Bartlett 23:38 As career advice for an entrepreneur or someone that's not an entrepreneur, what do you mean by spikiness, and why is it important?

Harley Finkelstein 23:45 Oh, so this is gonna be, uh, a long-winded way to get there, but I think it's important.

Steven Bartlett 23:48 Go long.

Harley Finkelstein 23:48 Um, I, um ... When I was building that T-shirt business in college, a mentor of mine, I'll say his name, his name is Philip Reimer. He's a senior partner at a very prestigious law firm called Dentons. They're in the U- They're everywhere. They're all over the world. And he's like, you know, he's had this incredible white shoe law firm career. He basically convinced me to go to law school.And he convinced me to go to law school, not to become a lawyer. He's like, "The skill set that you need, given what I think your ambitions are around business creation, business building, entrepreneurship, you are lacking some, some sophistication. You're, you're always going to struggle with these sort of things." And he's like, "But I have this idea, which is, go to law school, not to get good grades necessarily, not to get, not to become a lawyer, but to effectively, selfishly disseminate all this information from your classes to make you a better entrepreneur." And I think because I sort of had a very clear view that w- I, I wasn't sure at, at that time, I was 21 when I started law school, I didn't know exactly what my spiky point was, but I knew it had to do with entrepreneurship. And so Phil, when you're 21, I didn't know very much at 21, um, I thought this t-shirt business would just be a thing I'd keep doing for, for, for many more years. But Phil had this idea that actually to

Harley Finkelstein 25:00 sharpen your point, you should do something that is not obvious. And in hindsight, it really feels like what Phil was helping me to figure out was finding more alpha in terms of entrepreneurship, finding some arbitrage opportunity, something that, that is, that exists that no one is looking at, but that I can take advantage of.

Steven Bartlett 25:16 Something unique? Is, is that what you're saying?

Harley Finkelstein 25:18 Yeah, s- exactly, something really unique. That, hey, you're a good entrepreneur, you're not a great entrepreneur, you're not sophisticated, you, you don't understand, you don't understand all these different aspects of entrepreneurship. You should go to law school to c- not to be a lawyer, but to be a better entrepreneur, and you should be selfish in law school and in that, in, in your curriculum in deriving as much insight as possible, so that when you leave law school, you can return to entrepreneurship in a much better version of yourself.

Steven Bartlett 25:42 Because you'll have something that the competitor set, other entrepreneurs-

Harley Finkelstein 25:45 Wouldn't have.

Steven Bartlett 25:46 ... wouldn't have.

Harley Finkelstein 25:46 That's right.

Steven Bartlett 25:46 So you could have gone, like, you know, Steve Jobs did that, like, typography class.

Harley Finkelstein 25:49 That's right.

Steven Bartlett 25:49 And that's why we have these incredible devices in front of us.

Harley Finkelstein 25:51 That's right.

Steven Bartlett 25:52 So it's an unobvious skill that's complementary.

Harley Finkelstein 25:54 And that's why I say it's sort of finding alpha or, or an arbitrage opportunity, because it, it'll, it, it's something that is not obvious to most people, but now in hindsight when you think about it, you're like, "Well, that makes total sense." Look, I, I, I went to, like, I went to public high school, and it was a good school, but I didn't learn how to write very well. And then I went to McGill and economics, I didn't learn how to write very well. I learned how to write really well in law school, because all you're doing is writing factums and memos all day l- you know, all day long. I learned how to negotiate and how to do d- real critical debate and critical reasoning. I learned how to read 2,000 pages and pick out the one line that matters. All these things on their own does- doesn't seem like it would, it would create the curriculum of a great long-term entrepreneur, but it did. And I think part of the reason why I allowed myself to go through that process of law school was, I didn't know exactly what my spiky point was, but it felt like it's, it's definitely in the realm of entrepreneurship. I didn't realize that I, I would help build a company that would create millions of new entrepreneurs, but I knew entrepreneurship was deeply personal to me, because it helped me, it was my family story of survival. It just felt like this incredible tool that, that most people had not discovered yet. And so on that spiky point, I think the sooner you figure out that spiky point, ev- you don't have to be precise. I didn't know I was gonna run a software company, but I knew that entrepreneurship was deeply important to me, and so as I made decisions starting at 21 years old, every decision was under the lens of, "Is this going to help sharpen my, my, my, my, my points? Is this going to make me a better entrepreneur?" And I think if I would have realized that 10 or 15 years later, um, it still would have been fine, but it may have not have happened as... it wouldn't have happened the same way, and it may have not led me to join a group of, uh, you know, a handful of really smart engineers building this crazy piece of software called Shopify 14 years ago.

Steven Bartlett 27:38 I think this is, uh, an exceptionally un- underspoken about point, which is this idea of, like, skill stacking, but stacking skills that are unobvious and rare within an industry. So if we take... and I think we should go through this in a little bit more detail, because I think it can really have a profound impact on people. I read about how, um, the best people in the world, I think it's a mathematical equation, where if you're the best at six skills in an industry that are, like, unobvious, you actually are the best in a million people at that thing. So I mean, if there's a village of a million people, and, and they showed this little graph, I remember seeing it and writing about it a little bit, where if you just, if you're just in the top 10% at six complementary skills, you're the best in the village at that particular thing. Like Cristiano Ronaldo, the football player, he's not the best, he's not the fastest player in the world, he's not the, the, the, um, the best shooter in the world, he doesn't take the best free kicks in the world, doesn't head the ball the best in the world. He's considered the best player in the world by many because he indexes high the top 10% at various things. I think about Jack who records this podcast. Now, if Jack was a- wanted to be a, a podcast director, what all podcast directors or producers do is they'll go learn how to do microphones and cameras. Now interestingly, I don't think that's the, the, the place to be placing your time to become the best in the world. As we saw in the case of Steve Jobs, who went and did typography and design, and then made these beautiful devices, Jack should probably go and try and get an unobvious but- uh, skill that would be in high demand and low supply in this industry. So if Jack went into theater, he would learn maybe about how to cr- construct a story arc.

Harley Finkelstein 29:10 Mm-hmm.

Steven Bartlett 29:11 Or if he went and did, like, I don't know-

Harley Finkelstein 29:13 Or set, set design also. You could use theater.

Steven Bartlett 29:14 Yeah, or DJing, if he went and learned to be a DJ, then he would learn about stems and music and whatever else, or set design if he went and did a theo- so it's, it, and, and that would make him be... I'm not s- using Jack, I'm just saying someone in Jack's position, that would make them be a real fucking hard to find talent. But yeah, it's funny because we can, in industries like, I always think this about, um, coders, and, um, I don't hate to sort of generalize here, but it probably does sound like a generalization, um, it's sometimes hard to find someone who can code who's also an exceptional storyteller and visionary.

Harley Finkelstein 29:46 Mm-hmm.

Steven Bartlett 29:48 Often in companies there are two separate roles, right? So if you're a, if you're a coder instead of becoming even better at coding, for example, going and doing those little, like, public speaking sessions is probably an unbelievable hack, because then you can build and sell.

Harley Finkelstein 30:00 Sure. And actually, that brings up two, two points. One is, most people start companies with people just like them.

Steven Bartlett 30:06 Yeah, yeah.

Harley Finkelstein 30:07 Most people start companies with people that they would have been friends with in high school-I think that's a terrible idea. In fact, if you are in college right now listening or watching this, and you're in the business program, commerce, or you're in the engineering program, don't start a company with the person sitting next to you. Walk across the street, go to a different faculty, go to the Faculty of Arts, or go to the Faculty of Philosophy, or go to the Faculty of Engineering, and find someone there to start a company with.

Steven Bartlett 30:29 Mm.

Harley Finkelstein 30:29 I think some of the best partnerships and relationships that I've seen that have built things that are, that change the world from a company perspective, phil- philanthropically, whatever they, whatever they're, they're trying to build might be, building with other people with complementary skill sets is incredibly valuable. In fact, I think you get a much richer set of stacking of skills. You mentioned DJing in terms of skill set. I never appreciated ever how important my experience DJing, I DJed like hundreds and hundreds of bar mitzvahs over my time, hundreds. Um, I never appreciated what I learnt from, as a DJ and how, how I apply it to running a large public company. But the truth is, there's all these different things. So for example, something I noticed early on, I was like 14 or 15 years old, if the pre-meeting went really well with the clients, no matter how the party went, it was going to be a great result. Because if I had a good relationship, a good connection with the client, even if half the party didn't want to dance, the client knew me and knew enough about me and knew that I was going to try my best, that even if half the party was dancing, they were happy about that.

Steven Bartlett 31:32 And they were on your side.

Harley Finkelstein 31:32 And they were on my side. There was this immediate connection. And so now before I, I go into any, any, you know, serious negotiation, I try to get to know the person on the other side of the table. I try to find some common ground. We're both dads, we're both parents, we're both, you know, uh, whatever, we're both from the same place. That's the first thing. The second thing is read the room. So one of the things about DJing you have to do is you have to read the, the audience. And if the audience, you know, is clearly, uh, if you're, if you're playing disco and no one's dancing and you gotta make, you know, like a hard right into hip hop or rap or something, or top 40, like you can see glimpses of that. You, you try one song, you see how people, you watch their faces. How do people resonate? Oh, they really like this song. Great. I'm gonna go like Mo Money, Mo Problems from Notorious B.I.G., and the whole crowd erupts.

Steven Bartlett 32:16 Mm-hmm.

Harley Finkelstein 32:17 Things like that really do make a difference. Um, you know, there is, instead of asking people to get up from their chairs and come onto the dance floor, which is an awkward thing to ask people to do after dinner, instead have something in the middle of the dance floor that people want to see. So maybe, for example, one of the people that is hosting makes a speech and you say, "Uh, ladies and gentlemen, at this point, please, please get up in your chairs and take ten steps forward because the father of the bride is gonna say a few words." And everyone gets up and comes on the dance floor. And then when that speech is done, everyone's already on the dance floor. And so finding these hacks and these, these sort of ways to, um, not manipulate, but, but, but find better strategies for getting the thing accomplished, I learnt all that in DJing and I can apply all that to running a large public company today.

Steven Bartlett 33:01 This, um, you know, when we start businesses and stuff, go- going back to that point again, like we, we tend to go deep on the subject matter, but what I've heard from that is our hobbies and the things and the curiosity we have outside of the area that we're building in is equally important than, like, if I'm building a th- I don't know, if I'm building a, um, I'm building mugs for people to drink tea out of, much of my inspiration will come from all the other things I do in my pa... And the problem is we kind of deprioritize that part of our lives to, to focus on this thing. But taking a step away from the painting allows us to see the picture a bit clearer and also to, to create that picture a bit clearer, which I think is a conversation people don't have enough, because they think their hobbies are, again, deductive.

Harley Finkelstein 33:41 Toys or games.

Steven Bartlett 33:42 Yeah, yeah, yeah.

Harley Finkelstein 33:42 I totally, totally agree.

Steven Bartlett 33:43 A waste of time. Yeah.

Harley Finkelstein 33:43 I mean, look, I mean, this is what a polymath is. A polymath understands a lot of different areas of the world, uh, or comprehensivists understand a lot of the other, and pulls those, those different things in. My, um-

Steven Bartlett 33:52 What's a polymath? Sorry.

Harley Finkelstein 33:53 A polymath is someone who knows a lot about a lot of different things.

Steven Bartlett 33:55 Okay.

Harley Finkelstein 33:57 Now there are two things that I've done that were hobbies that ended up being hugely valuable is one, my wife started an ice cream company. In 2016 after we had our first daughter, uh, after our, our first child, my wife really wanted to start an ice cream shop in our, in our, in our neighborhood. There wasn't an ice cream shop. And so it was clear it was her business, not mine. She was very clear about that. She wanted independence. But even just helping her on things like accounting or, um, accounts payable or accounts receivable or helping her procure ice cream from the ice cream makers, that was super valuable, because one, it built huge empathy for the people that you shop with that are starting out. And the second thing I did was, um, during the pandemic, I was all by myself. I'm an extrovert, as, as, as you probably can tell. Um, my anxiety had, had, had, had increased to a degree that I had not felt in many, many years. And what I realized was I was drinking so much more coffee when I was by myself at home, way more, like double or even triple the consumption. And, um, my best friend, um, who's a sort of a tea f- you know, tea guy, loves tea, said to me, "I'm gonna actually get you to stop drinking coffee in the afternoon. I'm gonna replace your coffee with really great green tea." And I wasn't really a tea drinker. And so David started to bring me this great tea. And at some point I was like, "You know, David, I want to actually experiment with more of the features on Shopify." And I think this tea thing, I think most people's experience with tea was like someone getting the gis- gift basket and it was some bunch of crappy tea in there. I was like, people don't know, like, about this really great tea. They don't know how to make it. They don't know what to use it for, when to drink it. And so we created this, this little tea business called Fire Belly. And both, both those things were sort of hobbies in my life. They were sort of Sunday afternoon activities. I don't really watch sports on Sunday afternoons. I like to tinker and, and, and try different business ideas. Both those things have made me as a leader at Shopify so much more valuable. I understand pretty much every feature and functionality that Shopify has because I tried for myself. And initially when I told people that I was starting a little tea business, the answer was, "I don't..." Like, "Why are you doing that? That seems silly. You're not gonna change your life financially. It feels like a distraction." And I would say that's one of the greatest tools that I've ever, greatest things that I've ever done that has made me a better leader at Shopify. And it's just a hobby.

Steven Bartlett 36:09 Th- th- there's something, uh...... really, really powerful in that because when we, when I started this conversation, I asked you why people don't take the leap, and a lot of the reason why I think is because, a- and we talked about the psychology, is when I think about starting a business, like a tea business or any business, I'm stood at the bottom of Mount Everest looking up thinking, "Jesus Christ, like, I've got to find a website." As you said, "I think I need loads of money. Who's gonna work for me? Where do I get the tea from? How do I send it in the post? Um, what's the packaging? I need to do branding, and I need to do it all now?" And, and also, there's this other thing which e- in our minds we think of success as being me making millions or me making a ton of money. What- what I a- almost heard as you were telling that tea story was like, have this passion, remove the expectation, which Sir David Brailsford told me about really well, just remove the expectation of you ever, e- ever being anything more than a hobby, and just get going. And you'll, you'll stumble forward along the way, and, and that's okay. I think if more entrepreneurs could see that Mount Everest as just a bunch of pebbles and as... And remove the timeframe, uh, where possible, remove the expectation of huge success, and just stumble forward through the process, we'd have so many great, great more businesses than we do now. And everyone listening to this has that.

Harley Finkelstein 37:19 Yeah.

Steven Bartlett 37:19 They have the hobby. They have the f- they love tea. Or they love, I don't know, coffee or matcha or whatever it is. That perspective change of like, "Okay, well, today I'm gonna start my Shopify store. Tomorrow I'll think of the name. I won't, I won't even tell anybody just to remove even more expectation. And I'll just stumble forward through in my hobby and see where we get to in 10 years."

Harley Finkelstein 37:35 Most people on Shopify don't register their business until weeks after they sign up for Shopify. So most people don't even assume they're gonna need to register a business, and that's okay. I'm not... It's not to say that every idea you have in the shower needs to be commercialized, needs to see the light of day, but if, if there is an idea you have in the shower and you're having it a couple of days in a row, try it out. Like, y- I mean, this isn't a pitch for Shopify, but like, it's, it's less than a couple Starbucks coffees to go start a business today. And if you fail, the cost of failure is as close to zero as it's ever been. You don't have to take a loan out, you don't have to mortgage your house, you don't have to take food off the table hopefully. And if it works, you try it. And if it doesn't work, you try something different. But this idea of, yeah, that there's like this barrier to getting started. And I think, you know, one of the reasons that I think one of the best times to start your entrepreneurial career or your entrepreneurial, you know, business is in, is in school. The reason I think is because when you're in school as a student, there's very few expectations on you that this is going to be a huge success. So it's kind of the perfect time to get started, whether you're in high school, like with my DJ business, or in college with my, with when I sold T-shirts. It... There was very little expectation of me. No one thought it was gonna be successful anyway. And-

Steven Bartlett 38:52 If you sell one, everyone claps. (laughs)

Harley Finkelstein 38:52 Yeah, they're like, "Great, you're, you're... That's so cool. You have a business." No one asked me what my revenue is. No one's asked me about my EBITDA margins. I think it is a lot easier to get started on a business when you're in school or you're, or you have a job and this is sort of your side hustle. The amount of people... Shopify right now is about 10% of all e-commerce in the United States. Um, in places like Australia, it's e- way more than that. Um, I know most of our largest merchants 'cause I'm obsessed with this stuff. I love it. Most of the businesses on Shopify that are really successful, the homegrown success stories, they were accidental. It was Heather and Trina sitting at a coffee shop, not too far from here, with a friend of theirs that was a doctor who was wearing these hospital scrubs that just looked like shit. And they were like, "We can do this better." And that's how Figs was born. It was Ben Francis who said, "Why is there no clothes for just regular gym people? Either it's like gym rat stuff, like bodybuilders, or it's yoga." And that was the... That's how Gymshark came to the world. Or it's Ju- Tim and Joey at Allbirds saying, "Why is there no really great sustainable sneaker that feels good, that's washable, that costs this amount of money?" That was, uh, that, that's how Allbirds got started. So most... No one had this massive 80-page business plan and then got started. That's not how businesses are created in modern times. They're created based on this nugget of an idea, and they're explored, and you have, and you get curious about it, and you try this other stuff. And that's how you build companies that are long-lasting that change the fucking world.

Steven Bartlett 40:13 And that's how Shopify was started as well.

Harley Finkelstein 40:15 Indeed. Indeed. It was an immigrant from Germany coming to Canada 'cause he fell in love with a girl and got to, got to this new country and couldn't get a job because he didn't have his working papers and was told he could start a business. And he looks around, and he sees snow everywhere. And he says, "I'm gonna start a snowboard company." And in 2004, there's two ways to sell a product on the internet. One way, you sell them on Marketplace, which is very cheap, very inexpensive, but-

Steven Bartlett 40:40 Like eBay or something.

Harley Finkelstein 40:41 Exactly. But you're renting customers from that marketplace. They are not your customers. The other way was to spend seven figures, no exaggeration, and have one of these big enterprise companies build you an online store. And he didn't have that kind of money. He didn't like those options, so he wrote a piece of software and started selling snowboards. And the snowboard shop was called Snow Devil. And very quickly, people started asking him if they can use the software to sell their own products. And he decided snowboard store was a good idea, but the software behind it was a great idea. And that was how Shopify was born. And I met Tobi around that time when he was transitioning from snowboards into software, and I became one of the first customers to use Shopify in 2006.

Steven Bartlett 41:21 And then you were the first non-technical employee as well.

Harley Finkelstein 41:24 That's right. Yeah. Then a couple years later, after law school, uh, I called him and said, "I want join you and a small handful of engineers," smartest people I've ever met in my life still to this day, and said, "Let me, let me be your Swiss Army knife. Let me come in. I don't care what you call me. I'll be sales. I'll be finance. I'll be marketing. I'll form partnerships. I'll do, uh, uh, I'll do anything and everything you need because I believe the world will be better if we actually get this thing off the ground." And, and we've been working at this for, you know, um, it's my 14th

Harley Finkelstein 41:52 year now.

Steven Bartlett 41:52 When people hear those stories of these, you know, couple of, couple of women, couple of men, couple of people who had an idea, they saw a kind of gap in the market, they pivoted into it seamlessly, and here we are today, you know, it's worth tens of billions of dollars, whatever. The... I wanna zoom in on a particular thing, which is, at that ti- 'cause I hear this all the time from entrepreneurs. It's one of, again, one of the barriers for them starting is, well, someone is already doing it.... there's a- there's competition. And I think about every business that I've been involved in that's been successful, and at the time when I did it, there was someone that was way further down the head than me.

Harley Finkelstein 42:24 And probably better capitalized?

Steven Bartlett 42:25 Better capitalized, m- more information. (laughs)

Harley Finkelstein 42:27 More people. That's right.

Steven Bartlett 42:27 (laughs) Yeah. Smarter, yeah, all those things. And it never has mattered. And I- I- I c-can't quite articulate why it doesn't matter. I could probably try, but I want you to. Um, when you ... Toby, that small group of people, yourself, went off on that journey, was there competitors?

Harley Finkelstein 42:43 Totally. Tons. Very well... Big ones too. Yahoo Stores. Remember-

Steven Bartlett 42:48 No idea. (laughs)

Harley Finkelstein 42:49 In- in- in 2006, Yahoo was a really big company.

Steven Bartlett 42:53 It was huge.

Harley Finkelstein 42:53 Yahoo Stores existed. There were companies called Magento, which is n- still around today, uh-

Steven Bartlett 42:57 Yeah, yeah.

Harley Finkelstein 42:57 ... not- not- not- not as prevalent, but th- that was around.

Steven Bartlett 43:00 (clears throat)

Harley Finkelstein 43:00 There were major competitors out there. But the idea wasn't necessarily to- to try to do something no one else was doing, it was try to do it better. And that, I think, is the difference between the great companies and- and just the good companies, that there are always going to be good companies out there, but most of them are not necessarily trying to completely, you know, ch- like, move the needle on, like, what is possible. Um, all of those companies, by the way, that existed when Shopify was just getting started served a particular segment. It was either for, you know, like arts and crafts, like an Etsy kind of style, or it was for big companies, IBM, SAP Oracle had competitors there. Uh, Yahoo Stores focused on very, very small businesses. But we never gave ourselves those constraints. It was let's allow people and enable them to build beautiful online stores quickly, effectively, that were customized for their particular brand, and- and try to bend the learning curve around entrepreneurship. And over time, like over many, you know ... O- o- it's now almost 20 years. Over time, we're like, "Let's add payments. Let's add capital. Let's help with fulfillment. We should do point of sale because physical retail is important. What if we also help them with things like cross-selling across different markets? What if we create sort of a bank account to help them manage their cash flow?" Over time, it sort of evolved from that, but the initial idea had lots of other competitors in the space. This was not this massive novel thing. We just did it better.

Steven Bartlett 44:26 And it's funny, 'cause a lot of those competitors we absolutely do not remember now because you did it better. And that's the really important perspective shift, which is not like, "Am I the only one with this idea?" There's probably not a lot of value in the idea itself, but the execution of that idea, "Can I do it better?" is really where winners and losers are established. So that begs the question, h- how, what's the philosophy, and I'm very intentional with the word philosophy there, that enables a team to take a challenge where there's multiple competitors, in your view, and just do it better?

Harley Finkelstein 44:55 I mean, this is gonna sound trite, but- but, you know, having deep empathy for how merchants and how your customer uses your product is very, very important. And I think a lot of companies lose sight of that. They p- they- they focus on what, you know, what is- wha- what is known as, like, whales. Like, who are the power users? Let's focus on that. But we never did that. We actually think that the ... All of the merchants that I brought up so far in our conversation were- were merchants that started at their mom's kitchen table that grew to be multi-billion dollar, you know, hegemonic, um, incumbents. It's great. I- I love that we have Staples, and I love that we have SPANX, and I love that we have, you know, uh- um, uh, Black & Decker and Mattel using Shopify. But- but those are companies that were already successful before they started using Shopify. The stores that we are most proud of, that we love to talk about, are the homegrown success stories, because even though we are not responsible for their success, we simply made the journey a little bit less difficult over time. But the way that we think about these sort of things are, can we use software, can we use technology, to make things better? And by doing ... by adding more value, a disproportionate amount of value every single step of the way, we think we build a lot of loyalty with our merchants. And that ... What- what then happens is the ones that do become successful never leave Shopify. So there are people that start a business that- that- that- that fails, um, and- and- and they decide to either shut it down or they decide to pivot to a different business. We're okay with that. We're not changing physics. We know that n- that most small businesses will not be multimillion dollar companies over time. But the key for us is that the ones that do succeed never have to leave the platform. So it's almost like when you start on Shopify, it's super easy, super simple. In an hour or two, you can build a beautiful online store. But over time, as the complexity of your business increases, the solutions on Shopify sort of reveals itself over time. But it does so at the right time so you are not overwhelmed. And I think we are very hard on ourselves and ... I mean, that's the right term. We're hard on ourselves that we really want to continue to push the envelope. Here's a very simple example. Um, everyone right now is talking about AI. Everyone's ta- ev- obviously ChatGBT is really, really cool. We were using it already in a couple different ways. But the way we thought about it when it first came out was, this is all great, very cool technology. What is it gonna do for merchants? What is the practical implications of AI on the lives of- of the merchants? And for us it was like, "Well, wouldn't it be cool if AI helped merchants write product descriptions?" So you- you put in your product photography or some meta tags and ChatGBT helps you write a prompt description that will convert better. That is really practical. Um, you know, obviously in Web3, for example, we always thought about this is all cool technology, the blockchain is amazing. What can we do with it? Well, what if we can do token-gated commerce so that you can reward your most loyal customers with new opportunities, new discounts, new events? We use this lens of- of- of practicality across every single feature we have. And we also think about, well, what happens if this particular merchant gets really, really big? Um, I have a- a bit of a Moby Dick story. Um, my Moby Dick in terms of Shopify, the- the- the one brand merchant that I've wanted on Shopify for so damn long is a company called Supreme. You familiar with it?

Steven Bartlett 48:02 Yeah, of course. Yeah, yeah.

Harley Finkelstein 48:02 They're incredible.

Steven Bartlett 48:03 (laughs)

Harley Finkelstein 48:03 The Supreme story is amazing, but the reason I wanted Supreme on Shopify so badly, more than almost every other, any other brand, um, is because I knew that they would test the limits of Shopify. Their flash sales are probably the largest flash sales across the entire internet, which means they're probably the largest flash sales across all of retail. And I knew that if we got them on, it would pull Shopify into a new category of resiliency, of performance.... most companies would've shied away from that. Most companies would've been like, "We don't want Supreme. We know they're a great brand, but they're gonna break this place. They're gonna break our product. They're gonna break our infrastructure." We invite that in. We want Supreme to be on because we know that if we can handle a s- an iconic Supreme flash sale, we can handle anything else. And there's a little bit of like, um, there's a great book by Nassim Taleb called Antifragile.

Steven Bartlett 48:50 Yeah.

Harley Finkelstein 48:50 Are you familiar with that? I love that book. And, and all, for those that haven't read the book, all you have to understand is that there are three systems. There's the fragile system. I take this glass, I drop it, it breaks. There's the robust system. I take this, I drop it, it stays, uh, stays as, as a glass. But there's a third system, like the immune system, where if you break it, it actually rebuilds itself better, stronger, faster. And Shopify's fundamentally an antifragile company. And I, I think you, your companies are, are the same way. You guys invite what, call it pain, call it challenge, because ultimately you want to come out the other side better. And most companies, like literally 95% of companies out there, maybe more, don't want that pain. They want to be copacetic, and they wanna continue the status quo.

Steven Bartlett 49:35 Really interesting. You know, I, I mean, my, my head went all over the place when you were just going through those stories, because I remember when this podcast started to grow, our provider actually told us to leave because we were bringing too much traffic. (laughs) Which-

Harley Finkelstein 49:47 So that provider is never going to have-

Steven Bartlett 49:49 (laughs)

Harley Finkelstein 49:49 ... incredibly sexual pod- successful podcasts-

Steven Bartlett 49:51 Yeah.

Harley Finkelstein 49:51 ... ever again because they told you to leave. What if they would've invited you to stay and said, "We're gonna build more resiliency for you"?

Steven Bartlett 49:57 Yes, they were like complaining about us. (laughs) They were like-

Harley Finkelstein 49:59 Shame on them.

Steven Bartlett 49:59 (laughs) Yeah.

Harley Finkelstein 49:59 Shame on them.

Steven Bartlett 50:00 Yeah. So we, we, we moved to a different, um, h- someone else that could host us because they said that, that we were, we had too many downloads or something. Which is-

Harley Finkelstein 50:07 You have too many down... That, that, that is literally saying you were too successful.

Steven Bartlett 50:10 I- am I right, Jack? I wanna make sure I'm correct. Yeah. 'Cause you dealt with them. Yeah, they basically said we were costing them too much money.

Harley Finkelstein 50:16 I mean, that-

Steven Bartlett 50:16 We are costing them too much money.

Harley Finkelstein 50:18 By the way, most companies are like that. They fire customers that pull them in, in different directions. As opposed to the best companies embrace that.

Steven Bartlett 50:27 Mm.

Harley Finkelstein 50:27 And say, "Come. Break our stuff. It's going to make us better." If you believe, like... And by the way, antifragility is not just something for companies. It's also for human beings.

Steven Bartlett 50:35 Mm-hmm.

Harley Finkelstein 50:35 I think all of the stuff we talked about, about my upbringing made me better, made me stronger. Do I wish it, those things wouldn't have happened? Potentially. I mean, in hindsight, I, I wish I would've had (laughs) I'd had less anxiety maybe.

Steven Bartlett 50:46 Mm.

Harley Finkelstein 50:46 But maybe I would be sitting here with, with you, Steve, today if those things wouldn't have

Harley Finkelstein 50:50 happened.

Steven Bartlett 50:50 Is resilience the antidote for that? And, and if so, then how do we foster resilience in teams and people?

Harley Finkelstein 50:55 Uh...

Steven Bartlett 50:55 Because if you're at Shopify and you're an ambitious company, as I know you guys are, and you're saying, "We're go..." You know, AI comes out, and you're saying to the team, "Listen, forward. Let's figure this thing out. Let's, let's build some stuff, and let's try it. Let's go forward," uh, y- you're gonna have to bring people along with you. And those people are gonna go, "I just got comfortable with, with what we're doing now, Harley, and now you're telling me to..." So do you ha- how do you create that culture that fosters that sense of, like, resiliency and positive attitude towards change?

Harley Finkelstein 51:19 Yeah, two things. One is resiliency can be taught. You're not born resilient. You can actually learn resiliency. You can learn from your experiences. You can learn it from practice. But resiliency I don't believe is something you either have or you don't. You can actually build resiliency. In fact, I think people, the most interesting people that I know that are resilient have had something happen to them that allowed them to build resilience on their own. Some of them, you know, cracked.

Steven Bartlett 51:42 Mm.

Harley Finkelstein 51:42 But others actually... It, it's like, you know, uh, the, the, the metaphor that I love to use is like a huge tidal wave is coming. Some people grab their surfboards, and some people run for the beach to get the towel. W- I like the surfboard people. The surfboard people are my people. Those are the entrepreneurs. In terms of how we do it at Shopify, is Shopify is a company building software for entrepreneurs that is built by entrepreneurs. The, like, the amount of people at Shopify who had a business, have a business, are about to start a business, have side hustles, anyone you've ever met that works at Shopify, 'cause I know the people you've met at Shopify, Steve, they're also entrepreneurs. And actually, rather than on, doing their own ventures, we are collectively coming together to build something much bigger together. Like 1 + 1 = 10. Um, and I think one of the ways that you foster a culture of resiliency is look for the entrepreneurs. The reason I met Tobi in 2005 was I moved to Ottawa to go to law school. Had no friends, no family, never been to the city. I only went there because a mentor told me to go to law school, and he was teaching law at the University of Ottawa. That's how I got there. And I asked one simple question to anyone I met, "Where do the entrepreneurs hang out?" And I found this coffee shop with five other entrepreneurs who every Friday night got together and spent time learning from each other and sharing war stories and sharing tactics. And that became my tribe. One of those entrepreneurs was Tobi. So I love entrepreneurial people. I love resilient people. And so you can search those people out. When you're building your company, you're trying to create a culture that is, you know, super effective, that has, that looks for, that looks for the alpha opportunities, that is very ambitious, that works hard, invite entrepreneurs into your company. Create an environment that entrepreneurs want to be there. And, and I, I think that's what we've done. And I think, we have about 10,000 people at Shopify, and I would say the vast majority of them would say they're either entrepreneurs or aspiring entrepreneurs, but every single person at Shopify is very entrepreneurial. And it's the same reason where you gave, you told me a story earlier about, you know, Jack taking a photo of the, of the bookshelf.

Steven Bartlett 53:41 Yeah. (laughs)

Harley Finkelstein 53:42 I mean, I'm not just saying 'cause he's filming us and he's gotta make me look good here. But like, that's the entrepreneurial way to do it. The non-entrepreneurial way to do it is to be like, "Yeah, we need some books." You have the exact same books behind you here as you do in London. Most people won't notice that. But I notice the amount of attention and, to detail you have and the care you've taken, that every, that, that, that B is exactly where the B is on the shelf behind you. That matters. It doesn't matter to everybody, but it matters to the right types of people. And when you do that, you invite more of those people into your life.

Steven Bartlett 54:13 Do you, do you think as well, though, that when you think about companies and leaders and how the culture is set and how that philosophy of, like, attention to detail is set, I, I've often thought that you might get like a group of people, like disciples of the culture, maybe the original founders or something, and they set, they set that philosophy. They go, "This is who we are. We care about the bookshelf being the same no matter where we are in the world." And then you have this other type of people who are susceptible to go either way depending on the culture they're in.And if the culture's strong, those people become the culture. If the culture's... If they went somewhere else, they'd probably behave differently and... But that comes down to the culture just being absolutely crystal clear, and the hiring of that culture being disciplined, and the firing.

Harley Finkelstein 54:54 Yeah. A- a- I mean, let me, let me disagree with you on, on one point. I don't think culture should be static. I should think that every new person that joins your company or my company, the culture should change slightly. And hopefully it gets better over time. But I think there's a lot of companies that they put a, a poster of an eagle up on the wall that says, "Leadership," underneath, and they call that culture. Or they say... You know, there... Famously, uh, Patty McCormick created what's, what's now famously known as the Netflix culture guide.

Steven Bartlett 55:20 Yeah, I remember reading that.

Harley Finkelstein 55:21 And what was cool about that was the talent team, the recruiting team at, at Netflix, gave out this culture guide in advance of you even applying to Netflix. It was a public document. So you can read this and if this does not resonate or this is offensive to you, don't even apply. I think that's actually a very good thing to do because it just... It's very honest about, "This is the type of place." I think one of the, one of the funniest, uh, lines in there was, um, uh, "Mediocre performance will lead to, uh, superior severance."

Steven Bartlett 55:46 Yeah, yeah. (laughs)

Harley Finkelstein 55:47 I love that, right? It's super, super cool. So there's, there's, there's that aspect which I think is, is really interesting. But I think the culture should continue to evolve and everyone that joins, it should get better and better. But I wanna just say something, like this is... This narrative of the early days, I think is bullshit. Like this is a better version of Shopify right now than we've ever had. Our team is better. Our leaders are better. Yeah, there's some romanticism about the early days where, you know, like there's a photo that floats around every now and then of me sweeping the floors. I get it. There's... That was kind of romantic that we sweep the floors ourself. But I actually think over time, you could have a fa-... If you... Like part of this is like is your company founder-led or professionally managed? And those are fine things. But it... I don't actually think you need to actually have a founder there to be... to have a founder mindset. I think you actually need to have... If your culture is strong and, and people do the right thing when no one is watching, and people are constantly challenging each other, and people are constantly trying to, like, pull the product in, in a really unique positive way, that's a place where more people like us want to work. And therefore other people like us want to work as well. And that's why I love the idea of, like, building a company for entrepreneurs built by entrepreneurs. That is really compelling.

Steven Bartlett 57:03 When I- when I- when I speak about culture, I think I'm kind of using the word interchangeably with the word, um... In that particular case, maybe the word values. But let's... If we think about company culture in, in the context you're describing it, I was, um... I was doing some writing over New Years and I was looking at the f- the life cycles of, of companies and they, they often start like cults. And I went through, I think IBM, Instagram, all of these huge companies, and I, I found quotes of the founders describing the early days like a cult. And then they go into this kind of growth phase where because everything is breaking and they're trying to keep up with the market demand, they're having to, like, rapidly install processes. This is usually where founders, like, hire someone (laughs) -

Harley Finkelstein 57:39 Yeah.

Steven Bartlett 57:39 ... who's got like gray hair, who's done it before, and they sit them down with the little cult and they're like, "Help," in that growth phase. And then they get to kind of like this enterprise phase where the processes are in place, work/life balance has kind of been restored. They have a lot of people, so now they have like a HR department and things are different. Now going back to that first phase, that cult phase, it seemed pretty clear to me even like Peter... There was a quote from Peter Thiel where he was like, you know, um, he... Words to the effect of, "The start should resemble a cult." Do you believe that? It's something I've pondered-

Harley Finkelstein 58:12 Yeah.

Steven Bartlett 58:12 (laughs) Because the word cult is such a toxic word, so be careful here, Ali.

Harley Finkelstein 58:15 I mean, I, I, I... Yeah, I don't, I don't know-

Steven Bartlett 58:18 I'll tell... Let me-

Harley Finkelstein 58:18 I'm not sure if cult's the word I would, I would use. What I do think is that you need to have like... And this is not just in early days. It's, it's at every stage of a great company. You have to have a strong mission. And part of the reason that I think Shopify, for me at least, is the place where I can do my best work is because the mission is not interesting or cool or... It really hits home for me. I'm not... It's not to say that I wouldn't be a good, a good president of, of, of Pepsi. I'm sure Pepsi's mission... I don't know what it is, but I assume it's something like, "Do something with the world and make people happy," or something like that. Ultimately, they're- they're selling products. They're selling sugar water, and they're selling candy, and they're selling chips, and whatever they... whatever Pepsi sells. I don't think I can do my life's work at Pepsi. I don't. Because ultimately, at the end of the day, the mission of the company, even if you add all types of, you know, rose petal glasses and, and you say, "Well we're not..." It's, "We're not selling cola. We are, you know, uh-"

Steven Bartlett 59:15 Selling dreams.

Harley Finkelstein 59:15 "... we are nourishing the youth of the world to pursue their path." You're selling something that, like, I like, but I don't really love. And I think if you're... if you have the ability to find a company whose mission you believe in, in every... at any stage really hits you hard, that's probably the company you should go work at. And you should probably stay there for a very long time. And even the fact that not every c- not every person needs to stay at every company forever. Not everyone's gonna be a lifer. That's okay. People want to jump on the bus and... or the rocket ship at different times. That's fine. But I think you do your best work when the mission of the company deeply reflects your own life's mission. If I wasn't at Shopify, if Shopify didn't exist, I probably would be doing something around encouraging more entrepreneurship, inspiring more entrepreneurs, creating tools that help entrepreneurs start, scale, and build faster. I just found this, this vehicle that does it way more efficiently than I ever could do on my own. It's called Shopify. So you're damn right I'm gonna be... want to be on that bus or that rocket ship. But I don't think it has any- anything to do with what's on the wall. I think it has to do with the fact, like, what is the company actually doing? If you strip away all the marketing speak and all the brand speak, what is the point of the company? What's the objective? And I think that's... that really matters.

Steven Bartlett 1:00:31 For those entrepreneurs then that Shopify supports, wh- when we talked about this Mount Everest analogy where you're- you're thinking about starting a business, you're looking up, it feels super intimidating. We talked about how you can break that down into simpler steps, focusing on turning your hobby into a- into a small business. You gave the example that many of S- Shopify's merchants don't even register the company by the time they start the store. The other part that's, um, intimidating when I'm thinking about starting a business, if I'm a startup entrepreneur, is just information. And you used the word, uh, earlier on, you used the word mentorship. Now, okay, I've got a philosophy to how I'm going to start it, I'm going to focus on a hobby, Harley, um, I don't need a ton of capital as you've outlined, but then there's this information piece, which is maybe the most important piece. Because information, for example, is even the knowledge that a Shopify exists. It's also like, how do I find where I'm gonna get this tee from? How would you recommend an entrepreneur solve the information problem? And if you could give me some kind of reference to your framework on entre- on mentorship, that'd be super helpful.

Harley Finkelstein 1:01:30 Yeah, I mean, the mentorship framework that I use, it's actually really simple, it's that I don't think any- any one particular mentor is going to be, uh, you should wholesale take everything they say. Um, Lindsay and I got married in 2013, and I thought about who are all the people that I perceive to have a really great relationship with their spouses? And I went through the list, and I kind of laughed I was like, "Okay, like am I really gonna ask that person to be my mentor?" Like, I don't really respect that person in any other avenue in their life, so like, why would that person be my mentor? So I went through this list and I realized, "You know what?" Like, "I'm- I'm doing this all wrong." If I want to be a really good husband, a really good father, a really good leader of Shopify, I want to be a really good human being, uh, from a charity or philanthropy perspective, instead of trying to find one size fits all, like one person that's all those things where it all comes together, it would be so much better for me actually to just focus on verticals. So in the vertical of parenting, who's someone that I think does a really good job on parenting? Three or four people, I'll give them a call. The neat part about doing it that way as opposed to saying... and by the way, the person that like... I can't believe I'm sharing this, but this is kind of funny. Um, I told you about a mentor of mine that convinced me to go to law school. I love that guy, he's a huge part of my life, he's on his third marriage.

Steven Bartlett 1:02:48 Yeah.

Harley Finkelstein 1:02:48 He's not gonna be my marriage mentor.

Steven Bartlett 1:02:50 Could be your divorce mentor.

Harley Finkelstein 1:02:51 Maybe, yeah. But he's really good about understanding skill set or skill stacking as we talked about. There was someone that I called when I was about to get married to Lindsay who I just felt had the most special relationship with his wife, and I began meeting him and asking him questions about how do you cultivate that. The same thing with parenting. But all of these mentors in each of these verticals, they're not the same people. Now, the reason that's- that's- that's important is because like that, like a video game or like any skill set, you can't be good at everything and so I'm able to derive different things from each of these mentors and then create my own version of it but the second reason it's so, it's- it's a really cool way to do it is, that person who is a really great husband but maybe not a great entrepreneur, a lot of people... Like, no one else is calling him to ask for his advice on parenting because most people are like, "Well he's not someone that I'd want to emulate because in business he's not that successful or- or in other aspects of life he's not someone who I'd want to, who- who I- who I admire." And so the way that I've always thought of mentoring is find these different people for a different aspect of your life and then as it, as- as you're, as you evolve you may have to replace them and bring them in, bring them out. Some people may be around for a long time, other people after two years. I mean, I had a really good mentor around parenting who was really only valuable for newborns and it turned out that a couple years, you know, as the kids grew, he wasn't doing a very good job. He wasn't teaching his kids all the cool stuff that I want to teach my kids like skiing for example. So that's sort of my philosophy on- on mentorship, um, more generally. I think there's sort of two sides, so you have mentorship on this side which is like people you want to emulate, but then there's also sort of the tribe side of things. And the one thing that I don't think enough people take advantage of is whatever company you're trying to build in whatever vertical or geography or- or you know, whatever place, there are probably dozens of other people doing that exact same thing whether you're in London or you're in like Ottawa, Canada and finding a group of people who are at a similar stage even if they're not doing the same like, if I'm building a T-shirt business and you're building a DJ company like but I'm just getting started, you're just getting started, we probably both need to figure out like how to set up our bank accounts and how to get our first sale and we probably have to figure out like simple bookkeeping for example. So finding people that actually are at a similar stage even if they're not at the same vertical as you are is super valuable and those people exist, they're everywhere but finding them used to be really difficult. I actually think now it's much easier, go to Reddit, look on YouTube like you can literally go if there's a video about bookkeeping for DJ companies there's probably a video on YouTube somewhere. Go look at the comments, who's engaging in the comments there? Who's replying to those comments? Or on Reddit who's sort of a power user in a particular subreddit? You can find those people either online or- or- or- or in person and you can build yourself an informal board of directors when you're getting started. Now if one of you eclipses the other in terms of growth, you're probably not going to find as much value from that particular tribe as you- as you previously did, you're gonna want a different tribe but if you do this over time you actually end up with far more... The inf- the ac- the acquisition of information gets much easier over time and I don't think enough people take advantage of that.

Steven Bartlett 1:05:51 If I- if I gave you, um, if I gave you $3 million and I said, "Harley, you've got to invest $1 million in three companies more specifically three founders that are currently Shopify customers," who would you invest it in and why would you choose those entrepreneurs and founders?

Harley Finkelstein 1:06:10 It's like asking me like, you know-

Steven Bartlett 1:06:12 Choose your babies. (laughs)