The Diary Of A CEO with Steven Bartlett - Shopify President: How To Become A Millionaire For The Price Of A Starbucks Coffee!

Episode Date: May 8, 2023

In this new episode Steven sits down with the Canadian entrepreneur and President of Shopify, Harley Finkelstein. Harley was 17 years when we started his first company selling T-shirts at University. Later, while studying law at the University of Ottawa, Harley met the future co-founder of Shopify, Tobias Lütke, and became an early adopter of the platform. After graduating from law school, Harley worked as a lawyer before joining Shopify in 2010 as it’s first employee. Since then Harley has helped Shopify grow from a start-up to one of the world’s leading e-commerce platforms in the world, powering over 1 million businesses in 175 countries. In this conversation Harley and Steven discuss topics, such as: Harley’s mission to make more people into entrepreneurs Why Harley had no choice but to become an entrepreneur Downshifting and what ‘being enough’ truly means Why Harley searches for meaning rather than happiness Follow: Instagram: https://bit.ly/3M49FnB Twitter: https://bit.ly/3M3BLPF Follow me: https://beacons.ai/diaryofaceo

Quick one. Just wanted to say a big thank you to three people very quickly. First people I want to say thank you to is all of you that listen to the show. Never in my wildest dreams is all I can say. Never in my wildest dreams did I think I'd start a podcast in my kitchen and that it would expand all over the world as it has done. And we've now opened our first studio in America, thanks to my very helpful team led by Jack on the production side of things. So thank you to Jack and the team for building out the new American studio. And thirdly to to Amazon Music, who when they heard that we were expanding to the United States, and I'd be recording a lot more over in the States, they put a massive billboard in Times Square for the show. So thank you so much, Amazon Music. Thank you to our team. And

thank you to all of you that listened to this show. Let's continue. One of the greatest hacks for being an ambitious, hard driving entrepreneur. 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. Worth over $60 billion. He's helped scale brands worldwide. And he's now on a mission to help you start your own business. 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 shifted into this survival mode. I had no choice. And it's a very powerful driver. I met Toby 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's so 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 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 stores that we are most proud of are the homegrown success stories that grew to be multi-billion dollar businesses. If I gave you $3 million, who would you invest it in?

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 who... Oh, really? Yeah, those types of people that I would back. Harley, in your own words, who are you, what do you do? And what mission are you on?

I've always self-identified as an entrepreneur, full stop. 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? I mean, I think technically 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 going to sound really repetitive now, but is I want more people to try their hand at this thing that I call business creation entrepreneurship. And I don't think right now most people consider entrepreneurship as a thing that they can do to self-actualize. Why does it matter if more

people become entrepreneurs? 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's 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 despise. They go home at night, they go to the 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 concept of life's work is not something that my parents, my grandparents, 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. There's going to 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 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? 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 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 costs 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 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 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 of 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 grown up 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 that doesn't work, you can try it again. And that may be, you know, your Gymshark, your Alo Yoga, your James Purse. 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 start. And I was sat here the other day with an entrepreneur who's built multiple companies and been very people 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 it's actually pain, the pain of his current situation,

which drove him to take the leap. As it relates to people's like psychology and their self-belief and their self-confidence, when you're trying to get people to become entrepreneurs, what can we do there 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? 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 disparity or being desperate. And actually I think entrepreneurs by necessity are a big part of the greatest companies ever been created. The reason I became

an entrepreneur, I mean, I toyed with it as a kid, but when I really became an entrepreneur, it was because I had no choice. And it'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. I think that plays in sort of the passion side of things, 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 going to do right now? Either have to move back home to South Florida and live at home with my 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, just do it. That like, it wasn't about self-confidence. It was, here's a way for me to actually survive. And then that matters. 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 their journey of being rich and successful so they'll sit down and say what do i think is going to 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 going to start a hair care business i might do a coffee company or i might do crypto for example and you look at that and go. I'm going to start a haircare business. I might do a coffee company or I might do crypto, for example. And you look at that and go like, it's going to get so difficult for you in year one. You're going to quit all of these things.

What role do you think passion plays in eventual success? I think you have to actually like the thing you're doing to do it over a long period of time. My first, when I was 13 years old, I grew up in Montreal. I'm Jewish. I went to a lot of bar mitzvahs, that thing you do when, you know, 13 year old kids, 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. It turned out nobody would hire me because 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've always been a little bit short. I'm so short. But I looked,

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 around that time, moved back to Montreal when I was 17 to go to McGill University. My dad was no longer around. We can get into that if you want to. But I, at that point, it wasn't like, I'm going to 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 going to 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 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 that 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 to today, leading Shopify 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 the board will have me. So I think there's a time and a place for passion in these things, but I don't think it's the board will have me. 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. You referenced a few things there that I thought were quite interesting and that made my mind wander on to 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 conversations I had on this podcast with Barbara Cochran, the shark over here in the US, she said to me that her best investments she makes in entrepreneurs, they tend to have some kind of underlying trauma. And that ends up being fuel in their engine. So when things get really, really hard, they're driven 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 um do you think entrepreneurs should and founders

should go to therapy uh I think some should I think entrepreneurs and founders need to be self-aware I think that that's the first thing once they're self-aware and they understand hey there are some things that going on in my mind mind, in my personality, in my whatever, my being, I don't know 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 ayahu 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's 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. Yeah. And they're like, therapy doesn't work. No, that therapist didn't work. If you date somebody and the relation doesn't work, doesn't mean you're never going to 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 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's the greatest hack ever to just know more, to realize more. Is it gonna be painful? Unequivocally. The joke that I have with my therapist is I know it's been a good session if I feel worse after than when I did coming in. Because sometimes I come into these sessions

and I got swagger and I just had a great day and things are going my way. Then an hour later, I leave and I'm like, oh my God, I'm still such a work in progress. But that's, I think, what we're all choosing here. There's this great, my favorite poem or speech ever is this Teddy Roosevelt speech, the man in the arena. Did you know it? No, I'm going to butcher it, but it's effectively like, it is not the critic that counts, but 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, 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 got to be in the arena and in the arena, there's a lot of fighting and there's a, 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 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 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 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've signed up for. But if I'm going to check that box, this is the life I want, I'm going to be the man in the arena.

I need to acknowledge there's going to be critics who are going to try to tear me down. There's going to be the man in the arena. I need to acknowledge there's going to be critics who are going to try to tear me down. There's going to be internal critics that are going to try to mess that up. And I'm still going to pursue. I'm still going to move forward and progress. And I think therapy helps with that. What's your relationship like with failure? We talked a little bit about the idea of failure at the start of this conversation, why people don't take the leap from that, you know, 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. But if you're struggling with,

you know, enoughness, then it seems like that might limit your ability to want to fail fast. You know, 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 10 things have been successful and that 10th is not, it doesn't mean you are a failure. So one thing is I think separating like you being a failure versus the project or the particular thing being a failure is very, very different. Which is hard. Which is very hard. Toby, who is founder of Shopify and the person I spend most of my time with, 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 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 going to make it better the next time? And Shopify puts out a lot of products. We had our, we had something called Shopify additions, 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 additions where we put out all of the products and features that we built over the last six months. We do about a hundred 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 going to be a failure? 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 Toby and the board asked me to be the chief operating officer,

it was a huge honor. I mean, Shoplight 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 believe that like I can figure it out. 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 Toby and the team and said, look, there is this other role and we need

to bring someone in whose life's work it would be to be a great chief operating officer. We have that now. But man, Steve, I did not want to admit that I was not the right COO for Shopify because- Ego, right? Total. 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 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 than I was ever. Everything kind of came about, but it probably took too long. I think that story is an incredibly powerful one

because 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. 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'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 i know the people that they have to manage that point of self-awareness is so incredible i i reflect on a guy called pete who i offered a promotion to one day and he was like no i'm not ready and this must have been 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. 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. And I like really like my current job. Yeah. I like Pete.

Pete is the happiest guy I know. He has his shit together way more than I do. And not only is he happy, but he also, 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 just leads to a manager track. 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 sort of a new operating model for our team, for our organization.

And I think it's been, I think it got leaked to the press. So this is all public information. But if you want to be an incredible senior independent contributor in your IT, 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 doing data analysis or 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 going to make Shopify a much better company. But one thing you did talk about that you sort of raised 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 skillset. 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 Pete's of the world, when they say they don't want a promotion, they often get taken out completely. Well, Pete's not ambitious.

Pete's not going to be someone who's going to be 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. It's going to be hilarious when he hears this. Yeah. Maybe I do know Pete. But Pete has obviously a clear understanding of don't know pete is it's gonna be hilarious yeah um maybe i

do know pete but but pete is obviously a clear understanding of hey there's this thing this is the spiky object don't make me a riverstone i don't want to be well-rounded i want to 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 riverstones they say you got to be better here and better there. And I think instead, this sort of T-shaped, you've heard this sort of T-shaped model of skillset. 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. 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 how we build product and how we get shit done at Shopify. So I understand all those things because I need to speak to it intelligently and with conviction and with a deep understanding. But I'm never going to write code because there are people that should write code that are going to be so much better than I'll ever be. You did nail Pete. 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 an interesting moment for me. I was very young in my career as like a CEO. And I remember where I sat when he said, and what I recall is he was referencing that he still felt that there was work to be done in his role and that he didn't want to move up into this. I think it was a global role we're offering him because he didn't feel like he'd quite finished the work in his current role, which was just in the UK. You referenced spikiness. You know, you said you, and that gave me flashbacks to a conversation i had with um jimmy carl where he said we don't need more people that are shit at physics find the thing you'll get out and like double down there as career advice for an entrepreneur also when

that's not an entrepreneur what do you mean by spikiness and why is it important oh so this is going to be uh a long way to get there but i think it's important. Go long. 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 Denton's. They're everywhere. They're all over the world. 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 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

sophistication you're you're always going to struggle with these sort of things he's like but i have this idea which is go to law school not not to get good grades necessarily, 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 I wasn't sure 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. I thought this t-shirt business would just be the thing I'd keep doing for many more years. But Phil had this idea that actually to 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, something that exists that no one is looking at, but that I can take advantage of. Something unique? Is that what you're saying? Yes, exactly. Something really unique that, hey, you're a good entrepreneur. You're not a great entrepreneur. You're not sophisticated. You don't understand all these different aspects of entrepreneurship. You should go to law school not to be a lawyer, but to be a better entrepreneur. And you should be selfish in law school

and in your curriculum in deriving as much insight as possible. So when you leave law school, you can return to entrepreneurship in a much better version of yourself. Because you'll have something that the competitor set, other entrepreneurs wouldn't have. That's right.

So you could have gone like, you know, Steve Jobs did that like typography class. That's right. And that's why we have these incredible devices in front of us. That's right. So it could have gone like, you know, Steve Jobs did that like typography class. That's right. And that's why we have these incredible devices in front of us. That's right. So it's an unobvious skill that's complementary. And that's why I say it's sort of finding alpha or an arbitrage opportunity, because 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 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, you know, all day long. I learned how to negotiate and how to do real critical debate and critical reasoning. I learned how to read 2000 pages and pick out the one line that matters.

All of these things on their own doesn't seem like 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 definitely in the realm of entrepreneurship. I didn't realize that 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 most people had not discovered yet. And so on that spiky point, I think the sooner you figure out that spiky point, you don't have to be precise. I didn't

know I was going to 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 point? 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, you know, a handful of really smart engineers building this crazy piece of software called Shopify 14 years ago. I think this is an exceptionally 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, 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 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% of various things. I think about Jack, he records this podcast. Now, if Jack wanted to be 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 place to be placing your time to become the best in the world.

As we saw in the case of steve jobs who went into typography and design and then made these beautiful devices jack should probably go and try and get an unobvious but a 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 construct a story arc or if he went and did like i don't know set design also yeah or djing if you went and learned to be a dj then he would learn about stems and musics and whatever else or set design if he went and did a theory so it's and and that would make him be i'm not using i'm just saying someone in jack's position

that would make them be a real fucking hard to find talent. But it's funny because we can, in industries like, I always think this about coders and I don't hate to sort of generalize here, but it probably does sound like a generalization. It's sometimes hard to find someone who can code, who's also an exceptional storyteller and visionary. Often in companies, they're two separate roles, right? So 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. Sure. And actually that brings up two points. One is most people start companies with people just like them. 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, go to the faculty of philosophy,

go to the faculty of engineering, and find someone there to start a company with. I think some of the best partnerships and relationships that I've seen that have built things that change the world from a company perspective, philanthropically, whatever 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, DJing like hundreds and hundreds of bar mitzvahs over my time, hundreds. I never appreciated what I learned as a DJ and how I apply to running a large public company. But the truth is there's all these different things. So for example, something I noticed early on, it's 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 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. And they were on your side. And they were on my side. There was this immediate connection. And so now before 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 or both parents or both, you know, 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 audience. And if the audience, you know, is clearly, if you're playing disco and no one's dancing and you got to make, you know, like a hard right into hip hop or rap or something like top 40, like you can see glimpses

of that. 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 going to go like, mo' money, mo' problems from Notorious B.I.G. And the whole crowd erupts. Things like that really do make a difference. 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, ladies and gentlemen, at this point, please get up in your chairs and take 10 steps forward because the father of the bride is going to 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 sort of ways to not manipulate, but find better strategies for getting the thing accomplished. I learned all that in DJing and I can apply all that to running a large public company today. This, you know, when we start businesses and stuff, going back to that point again, like 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, I don't know, if I'm building a, 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 part. And the problem is we kind of deprioritize

that part of our lives 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 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. Toys or games. Yeah, yeah, yeah. I totally agree. I mean, look, I mean, this is what a polymath is. A polymath understands a lot of different areas of the world, or a comprehensivist, understands a lot of there and pulls those different things in. My... What's a polymath, sorry? A polymath is someone who knows a lot about a lot of different areas of the world, or a comprehensivist, understands a lot of, and pulls those different things in.

What's a polymath, sorry? Polymath is someone who knows a lot about a lot of different things. Okay. Now, there are two things that I've done that were hobbies that ended up being hugely valuable. One, my wife started an ice cream company. In 2016, after we had our first daughter,

after our first child, my wife really wanted to start an ice cream shop in our neighborhood. There was 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 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

that they're starting out. And the second thing I did was during the pandemic, I was all by myself. I'm an extrovert as, as, as you probably can tell. 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 my best friend, who's a sort of a tea guy, loves tea, said to me, I'm going to actually get you to stop drinking coffee in the afternoon. I'm going to replace your coffee with really great green tea. 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 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 little tea business called Firebelly. And 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 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 going to 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. There's something really, really powerful in that because 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, 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, I've got to find a website. As you said, I think I need loads of money. Who's going to work for me where do i get the tea from how do i send it in a 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 in our minds we think of success as being me making millions or me making a ton of money

what what i 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 being anything more than a hobby and just get going. And you'll stumble forward along the way and that's okay. I think if more entrepreneurs could see that Mount Everest, there's just a bunch of pebbles

and remove the timeframe 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. They have the hobby, they have the, 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 going to 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. 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 going to need to register a business and that's okay. And 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 there's an idea you have in the shower and you're having it a couple of days in a row, try it out. Like, I mean, this isn't a pitch for Shopify, but like 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 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, 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 business 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 gonna 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 when I sold t-shirts, there was very little expectation. I mean, no one thought it was gonna be successful anyway. You sell one, everyone clapped. Yeah. They're like, great. That's so cool. You have a business. No one asked me what my revenue is. No one's asked me what 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. In places like Australia, it's even way more than that. I know most of our largest merchants

because 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 they're 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 he that's how gym shark came to the world or it's tim and joey at all birds saying why is there no really great

sustainable sneaker that feels good, that's washable, that costs this amount of money? That's how Allbirds got started. So 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 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. And that's how Shopify was started as well. Indeed, indeed.

It was an immigrant from Germany coming to Canada because he fell in love with a girl and got to this new country and couldn't get a job because he didn't have his working papers and was told he can start a business. And he looks around and he sees snow everywhere. And he says, I'm going to start a snowboard company. And in 2004, there's two ways to sell a product on the internet.

One way, you sell it on a marketplace, which is very cheap, very inexpensive. Like eBay or something. Exactly. But you're renting customers from that marketplace. They're 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 Snowdevil. And very quickly, people started asking him if they can use the software to sell their own products. And he decided the 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 Toby around that time when he was transitioning from snowboards into software. And I became one of the first customers to use Shopify in 2006. And then you were the first non-technical employee as well. That's right. Yeah. And a couple of years later, after law school,

I called him and said, I want to 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 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 anything and everything you need because I believe the world will be better if we actually get this thing off the ground. And we've been working at this for, you know, it's my 14th year now. When people hear those stories of these, you know, 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. I want to zoom in on a particular thing, which is at that time, because 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 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. And probably better capitalized. Better capitalized, more information. That's right. Yeah, smarter, yeah, all those things. And it never has

mattered. And I can't quite articulate why it doesn't matter. I could probably try, but I want you to. When Toby, that small group of people, yourself, went off on that journey, what's their competitors? Totally. Tons. Very well. Big ones too. Yahoo stores. No idea. In 2006, Yahoo was a really big company. Yahoo stores existed. There were companies called Magento, which is still around today. Not as prevalent, but that was around. There were major competitors out there, but the idea wasn't necessarily 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 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, like move the needle on what is possible. 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's for big companies, IBM, SAP, Oracle had competitors there. 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 try to bend the learning curve around entrepreneurship. And over time, like over many, you know, 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 cashflow? 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. And it's funny because 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 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? I mean, this is going to sound trite, but 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 focus on 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 all of the merchants that I brought up so far in our conversation were merchants that started at their mom's kitchen table that grew to be multi-billion dollar hegemonic incumbents. It's great. I love that we have Staples and I love that we have Spanx and I love that we have, you know, Black & Decker and Mattel using Shopify. 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 then happens is the ones that do become successful never leave Shopify. So there are people that start a business that fails 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 most small businesses will not be multimillionaire 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. Everyone right now is talking about AI. Obviously, ChatGPT 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 going to do for merchants? What is the practical implications of AI on the lives of the merchants? And for us, it was like, well, wouldn't it be cool if AI helped merchants write product descriptions? So you put in your product photography or some meta tags, and ChatGBT helps you write a product description that will convert better. That is really practical.

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? 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 practicality across every single feature we have. And we also think about, well, what happens if this particular merchant gets really, really big? I have a bit of a Moby Dick story. My Moby Dick in terms of Shopify, the one brand merchant that

I've wanted on Shopify for so damn long is a company called Supreme. They're incredible. The Supreme story is amazing. But the reason I wanted Supreme on Shopify so badly, more than almost any other brand, 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 have shied away from that. Most companies have been like, we don't want Supreme. We know they're a great brand,

but they're going to break this place. They're going to break our product. They're going to break our infrastructure. We invite that in. We want Supreme to be on because we know that if we can handle an iconic Supreme flash sale, we can handle anything else. And there's a little bit of like, there's this great book by Nassim Taleb called Anti-Fragile. Are you familiar with that? I love that book. And 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 a robust system. I take this, I drop it, it stays 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 is fundamentally an anti-fragile company. And I think your companies

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 want to continue the status quo. Really interesting. You know, I mean, my head went all over the place when you're 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. So that provider is never going to have incredibly successful podcast ever again,

because they told you to leave. What if they would have invited you to stay and said, we're going to build more resiliency for you? They were like complaining about us. They were like, shame on them. Shame on them. Yeah. So we moved to a different, someone else that could host us because they said that we had too many downloads or something. You have too many downloads. That is literally saying you were too successful. Am I right, Chuck? I want to make sure I'm correct because you dealt with them. Yeah, they basically said we were costing them

too much money. We were costing them too much money. By the way, most companies are like that. They fire customers that pull them in different directions as opposed to the best companies embrace that and say, come, break our stuff. It's going to make us better. If you

believe like, and by the way, anti-fragility is not just something for companies, also for human beings. I think all the stuff we talked about, about my upbringing made me better, made me stronger. Do I wish those things wouldn't have happened? Potentially. I mean, in hindsight, I wish I would have had, I'd have less anxiety maybe, but maybe I wouldn't be sitting here with you, Steve, today if those things wouldn't have happened. Is resilience the antidote for that? And if so, then how do we foster resilience in teams and people? Because if you're at Shopify and you're an ambitious company, as I know you guys are, and you're saying, you know, AI comes out and you're saying to the team, listen, forward, let's figure this thing out. Let's build some stuff and let's try it. Let's go forward.

You're going to have to bring people along with you. And those people are going to go, I just got comfortable with what we're doing now, Harley. And now you're telling me to, so how do you create that culture that fosters that sense of like resiliency and positive attitude towards change? 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, but others actually, it's like, you know, the metaphor that I love to use, like a huge tidal wave is coming. Some people grab their surfboards and some people run for the beach, get the towel. 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 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, because I know the people you've met at Shopify, Steve, they're also entrepreneurs. And actually, rather than doing their own ventures,

we are collectively coming together to build something much bigger together, like one plus one equals 10. And I think one of the ways that you foster a culture of resiliency is look for the entrepreneurs. The reason I met Toby 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 Toby. 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 super effective, 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 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 told me a story earlier about, you know, Jack taking a photo of the bookshelf. I mean, I'm not just saying because he's filming us and he's got to make me look good here, but like that's the entrepreneurial way to do it. The non-entrepreneur 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 noticed 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. 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'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 that philosophy that 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 is strong those people become the culture if cultures if they went somewhere else they 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. Yeah. I mean, let me, let me disagree with you 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 poster of an eagle up on the wall that says leadership underneath, and they call that culture. Or they say, you know,

famously, Patty McCormick created what's now famously known as the Netflix culture guide. Yeah, I remember. And what was cool about that was the talent team, the recruiting team 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 lines in there was, um, uh, mediocre performance will lead to a superior severance. 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 want to just say something like this is this narrative of the early days. I think it's 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 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. That was kind of romantic that we sweep the floors ourselves. But I actually think over time, you can have a fan, like part of this is like, is your

company founder led or professionally managed? And those are fine things, but I don't actually think you need to actually have a founder there to have a founder mindset. I think you actually need to have, if your culture is strong and people do the right thing when no one is watching and people are constantly challenging each other and people are constantly trying to pull the product 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. When I speak about culture, I think I'm kind of using the word interchangeably with the word in that particular particular case maybe the word values but let's if we think about company culture in the context you're describing it i was um i was doing some writing over new years and i was looking at the life cycles of companies and they they often start like cults and i went through i think ibm instagram all of these huge companies and 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 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 because the word cult is such a toxic word.

So be careful, Yali. I mean, I, yeah, I don't know. I'm not sure if cult's the word I would use. What I do think is that you need to have like, and this is not just in early days, 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 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. It really hits home for me. It's not to say that I wouldn't be a good president 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 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 you

say, well, we're not, it's, we're not selling cola. We are, you know, 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, in any stage really hits you hard, that's probably the company you should go work at. And you should probably say that for a very long time. And even the fact that not every person needs to stay at every company forever. Not everyone's going to be a lifer. That's okay. People want to jump on the bus 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 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 going to want to be on that bus or that rocket ship. But I don't think it has 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 brands speak, what is the point of the company? What's the objective? And I think that really matters.

For those entrepreneurs then that Shopify supports, when we talked about this Mount Everest analogy where 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 small business. You gave the example that many of Shopify's merchants don't even register the company

by the time they start the store. The other part that's intimidating when I'm thinking about starting a business, if I'm a startup entrepreneur, is just information. And you used the word 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. 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 going to get this tea 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 mentorship, that'd be super

helpful. Yeah, I mean, the mentorship framework that I use, it's actually really simple. It's that I don't think any one particular mentor is going to be, you should wholesale take everything they say. Lindsay and I got married in 2013. And I thought about who are all the people that I perceive to have 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 going to ask that person to be my mentor? Like, I don't really respect that person in any other avenue of 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 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 husband, a really good father, a really good leader of Shopify, I want to be a really good human being from a charity or philanthropy perspective,

instead of trying to find one size fits all, like one person does 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 of it 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. 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. He's not going to be my marriage mentor. He'd be your

divorce mentor. Maybe. Yeah. But he's really good about understanding skillset 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 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 important is because 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 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 I admire. And so the way that I've always thought of mentoring is find these different people for different aspects of your life. And then 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 of years, you know, as the kids grew, it 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 mentorship 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 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 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 a bank account 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 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 in person, and you can build yourself and inform a 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 previously did. You're going to want a different tribe. But if you do this over time, you actually end up with far more, the acquisition of information gets much easier over time.

And I don't think enough people take advantage of that. 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?

It's like asking me like, you know. Choose your babies. Yeah, choose your favorite child. Yeah, really I'm trying to get at the characteristics of the founders that you back. You know, I know right now it's almost, if you sort of word clouded social media right now, the term content creator would come up

probably more than any other term. And I think actually it is completely misguided of what people think content creators are or do. I think a lot of people assume that what's happening right now in sort of the content creation spaces, you have someone that has a super successful podcast, for example, or a super successful blog or a super successful, you know, YouTube channel. And they want to, they want to expand their monetization. So they do something like they make t-shirts with, you know, the diary of the CEO on it. The greatest content creators now that I see really building their brands are doing something totally different. And I know this is an obvious example, but what Kylie Jenner did

with Kylie Cosmetics is nothing short of brilliant. Now, it's not to say that, you know, she came with a built-in audience. She was on this crazy TV show for her whole childhood. But she was someone who, if you followed her on social media eight years ago, eight years ago, you would have seen she really cares about makeup. She was in makeup tutorials and she was doing makeup classes and she was giving tips and tricks about makeup. And then eventually she's like, you know what? I want to create a better version of makeup for myself. And so she went into the lab. I know where the lab is. It's not too far from here. I know the store really well. And she went and she created what

she believed was a better version of makeup called Kylie Cosmetics. And then she brought it to the world. What Jimmy did with like Beast Burgers or with Feastables. Mr. Beast. Mr. Beast. Yeah. Yeah. Mr. Beast did with Beast Burger or Feastables. He didn't just go and go to a chocolate company and say, I want to create a Mr. Beast chocolate bar. He went, he loves chocolate. He loves chocolate. He also loves burgers. And he said, let's create a better burger than I can get right now on Uber Eats. And he went and he cultivated it. He said, this is fucking delicious. And now he's going to actually distribute it. He's going to actually scale it. I would definitely put one of those millions of dollars into the hands of a creator

who's on the precipice of figuring out what exactly does my audience like and then creating a better version of that. Because I think that most of the content creators out there do create promotional products where they put their sticker on something that already exists, but the good ones, the great ones, they actually improve on what already exists in the world. And then they have a built-in distribution channel because they already have an audience. So that would be the first one. The second one I think would be someone who does something very niche-y. You and I are both in black t-shirts.

In my opinion, there is someone who thinks about black t-shirts more than anybody else on the planet. His name is James, James Purse. James Purse is obsessed with black t-shirts. And so I love wearing black t-shirts. So this is maybe a selfish one. But I'd put a million dollars out of the three million that you're giving me metaphorically into James. And I would say, go do more of this. Because I actually, now I'm not sure he needs my money. Certainly, Mr. Beast doesn't need my money either. But I love the idea of someone going super deep

on one particular thing and building the best version of it on the planet. I don't think most people do it. I think most people start with something like a t-shirt and they go very, very broad. And James hasn't. I mean, he has, he makes other clothing, but he has a ping pong table, not joking, that he makes, which is the most beautiful ping pong table he's ever, I've ever seen. He has a couple of these sort of villa rentals in Mexico, which he designed himself. But he's, he, it's one particular vertical that I think is really, really cool. Maybe the third thing that I would invest in, so content creator would be first, someone like James Purst, who does one vertical really well, would be the second. The third one would be someone who is trying to bring something that was unattainable for the masses into their

hands. So this microphone that we're using right now is a Shure SM7B. And from everything I've read, because I like this type of stuff, it is like one of the greatest pieces of engineering, audio engineering ever created, which is why Shure, who makes the microphone, hasn't really changed it much. This is a great microphone. It's expensive. Someone who is taking a microphone like this this type of quality and creating a less expensive version of this so more people can try their hand at podcasting that would be really cool too interesting making like quality more accessible to the masses right that's right and and i don't just mean like there are other good microphones out there but you know the difference between

a dslr camera that we're using now versus a webcam. Of course. And in terms of the characteristics of the human, what do you bet on? I mean, we talked about this a lot, so it's going to sound repetitive, but it's resiliency. I'm looking for those surfboard people, the people that see that wave and grab the surfboard. I want people that are optimistic, but I think generally the people that grab the surfboard are optimistic. I want people that are hardworking, but I find generally the people that grab the surfboard are also hardworking. I want people that are high character. I think those are often the same people. But I want someone who, if you were to give them a million dollars or $10 million or $100 million, they would still do the exact same thing the day later because that is their mission.

That is their life's work. And I think if you find that, you should cherish that. Anyone who's watching that has found that thing that no matter what they had or don't have would do this particular thing, those are the types of people that I would back. I don't really care where they're based. I don't really care what their experience is.

I care about, are they the surfboard people? Because I think surfboard people are deeply curious and deeply ambitious. We spoke to your team and asked them what you in particular were good at. Oh God. They did not tell me you did that. Did they not?

They did not. We said, we said, could you tell us everything Harley's good at? And there was like a big sort of 30 second pause and then they just hung up the phone. And so we can, so we'll move on. I heard the gasp backstage here yeah someone in you probably couldn't hear that on the mics but everyone everyone that like works

closely on my team uh are all also all entrepreneurs themselves they all have side hustles oh really cool yeah no they said lots of many many amazing things about you um many many amazing things the one that i wanted to focus in on, because I wanted you to kind of explain this, is one of your team members said he's very, very good at the telescope process of effective prioritization. What on earth does that mean? I calendar everything. Well, they made it sound much better. Maybe they should be the storytellers. I truly, like, before I came here, I wanted to grab a quick coffee. That was in the calendar. My meditation this morning is in the calendar. The things that I really, really care about,

I diarize and I stick to that diarization. And because of that, I think it's easier for me to prioritize what's important to my life, both professionally and personally than most people who they try to fit things in. I often don't walk into a place, you know, you ever meet those people that like, they're always kind of in a rush? Me. Okay. I'm not, I'm usually not in a rush. I'm hard driving and I'm like, I'm always, you know, super go, go, go all the time, but I'm not usually not in a rush. And the reason is because the things that are deeply important to me are in the calendar. And I think most people don't, I think the user, I think a lot of people use their calendar for diarizing a zoom call or diarizer, you know, scheduling, I don't know, like lunch. I, I, this is going to sound maybe lame to some people. It's worked well for me

in my calendar. You will see walk with Lindsay, like walk with my wife. You will see like ski time with Bailey or Zoe. Um, everything is in the calendar. Every person, someone that I want to hang out with that. I want to actually a mentor of mine that I don't think I'm spending enough time with, they go in the calendar every four weeks and I commit to that. That helps me. I'm not sure I'm like the world's greatest prioritizer, but because of that, I'm able to prioritize things in a way that I think most people may not always be able to do. So that's one thing. In terms of the other prioritization, there's very few things that are nice to haves in my life. I don't do the nice to have thing. Things that are in my life are must haves. And Shopify is very important to me. Lindsay and the girls are very important to me. Some of the charity projects we're doing, particularly some of the Jewish charity projects

we're doing right now in Canada are very important to me. There's not much else. I'm not trying to also qualify for a marathon. I'm not also trying to, you know, do research on some other topic. Like this is kind of the stuff that matters. And so when you when our, when we,

you and I first connected, I knew that I would one day would love to be on your show. Why? Because like, when I think about, do you know the concept of Ikigai? Yeah. Yeah. So when I think about the Ikigai concept, which is really life's work, by the way, which is a Japanese, a Japanese version of it, which is far more elegant than, than, than the term life's work. But what am I good at? What is the world going to find value in? What can I get paid for? And what adds the most amount of value? I think generally, I forgot the exact terms. This conversation with you hits a bunch of those, like the intersections of Venn diagram, this hits. You're a great entrepreneur. Your audience are great entrepreneurs.

I knew the conversation would be interesting because I listened to this podcast and I love your show. It was obvious to say yes. If someone else asked me to do a conversation for a couple of hours like we are today, I have to put it through the filter of like, where does this hit on the Ikigai spectrum or on the life's work spectrum? I think that's why they say that. During your time at Shopify, what has been your most difficult personal challenge? Like what was the day or the period where you had your hardest time? I think it was on a personal level, it was probably the pandemic.

I felt very, very lonely. I just, I was low in energy. I was high in anxiety. and i wasn't making time it was like the pandemic was crazy for shopify overnight every physical retailer shut down and we were really lucky in that a lot of them ended up coming online with shopify that was really cool but we ended up hiring a ton of people very very quickly we were always by ourselves we were fully you know fully remote at that point and i i was not in a good place. What do you mean you weren't in a good place? I wasn't present at all for my, I don't think I was present for my team and I don't think

I was present at home. I felt like I was simply just trying to tread water and I wasn't making time. I had this sort of great, I talked about my calendar efficiency. I had this great sort of plan usually. And then the pandemic hit and like everything changed and scheduling all this time. Like I didn't replace the time with mentors that I meet in person with virtual coffees. I just canceled it. And so I just, it was a very reactive period for me where I don't think I was mindful of what I needed to be a good leader. And we were just hiring a ton of people. And I was lonely. I was really fucking lonely. That was a low point on the professional side. On a personal side, it actually happened a couple years prior to that. And it was really around the transition from being sort of COO to being president. I felt like I was letting down the company. I was letting down Toby. I was

letting down myself if I didn't have a particular role at the company. And that role came with a huge headcount. All these different teams reported up to me. From a headcount perspective, there were like 6,000 people that reported to me. It was kind of a crazy thing. But I knew it wasn't the right job for me. But I did not have the self-confidence, nor did I have enough introspection to say, I'm in the wrong job. And I was fortunate that other people, especially Toby, kind of pulled me into this new thing and said, hey, there's a role here that is different than what you're doing. And if you can just get over the fact that you're not going to have 6,000 direct reports, but rather you're going to have a couple hundred direct reports or maybe less than that even, but you're going to do more of the stuff you want, which also happens to be more

valuable for Shopify, that we're going to have a new phase. We have this thing in Shopify called tours of duty. It's every three years. And a tour of duty is, you know, it's a new mandate, new objective. And for the most part, most of my tours of duty up until this most recent one, I was in the same thing. I was just grabbing as much as I can, trying like Swiss army knife stuff. But I never kind of settled in to say, where do I actually want to do? Like, what is my craft here? I always loved storytelling, but I was never, I think I was too caught up with ego and insecurity to admit this is the shit I want to do. I don't want this the rest of my life. I don't want to get so good at this.

And it was really with help with coaching and the people around me that I was like, hey, what if I actually just did this thing? What if I took this other role called the president of Shopify and I just focused on this one aspect versus all the other things I was doing? And it turned out not only is it okay, but it's way more valuable. And I think I'm a much more valuable member of our team because I've sharpened my point rather than become a well-rounded Riverstone. In those dark moments and those hard times, did you speak to anybody? As in what I'm saying, I mean, speak to the people that were next to you. Did you speak to Toby? Did you tell your wife how you were feeling? My wife knew I wasn't happy. Did you have a conversation?

No, I don't think I was able, I don't think at that particular moment I was able to actually even see it. I was like, look, I've been here for a long time. Maybe this is it. Maybe I've hit, I've hit the, my max here, right? I mean, been here for a third of my life. Maybe this is it. Maybe I've, I've hit, I've hit the, my max here. Right. I mean, bitter for a third of my life. Maybe this is it. Maybe like I should just quit while I'm ahead. And what I didn't fully appreciate is that the thing that I really want to do is also the thing that everyone else really wants me to do. It's also really the thing that is most valuable to the company at this particular. For your self-esteem. I was like, well, but that's not enough. Yeah. I'm not not enough yeah i'm not doing enough i'm not contributing enough and what does that mean about me and myself that's right like i'm

not i obviously i'm not enough i am the happiest i'm not just saying that uh because we're on camera at this particular moment i'm the happiest and most fulfilled and i find the most meaning in my work that i have in a very very long time and it's because I'm doing the thing I should be doing, which is this particular skill, this particular role that I have is kind of built perfectly for me. And I need to be okay with the fact that I don't have the largest headcount and most of the company doesn't report to me. And I don't really care about that. What I care about is, am I adding the most amount of value? And do I feel like I'm growing? Do I feel like I'm actually contributing both to the company, but also to my own development?

And I think that's, if you can find that, if you have people around you, your partners, your colleagues, your board, whatever it is, that give you the permission to do that. Again, you can't just do what you want. Like, you know, if I want to like, if I just want to be the chef at Shopify, I'm not really going to add much value. But if it turns out that the Venn diagram overlapped of what am I really good at?

What does the company value for me? And what is something that is uniquely in my skillset? If wherever the Venn diagram overlaps, if you can do that, you win. What about in the pandemic when you were struggling? Did you have an actual conversation? I'm asking this question because I'm so compelled by like, when specifically with some men

who are often a little bit more hesitant to talk, I'm compelled by this idea of like, when we speak, when we reach out to a friend, a wife, a partner to say, listen, I'm struggling here. And do we do it after? Do we do it during? When did you do it? I did it way too late. I waited way too long for that. And I wish I had, and I think it would have saved a lot of grief. It would have, I would have been, I don't think the pandemic was especially great for anyone. All of us sort of dealt with it in our own way.

But I think that I made it way more difficult on myself because I was lonely and unhappy and maybe had some sort of, you know, maybe there was, I talked about anxiety, but maybe there's a bit depression there as well. However, I didn't talk to anyone about it because I didn't feel like I had the right to complain. I didn't feel like I had enough, to complain. I didn't feel like I had enough,

yeah, that I had enough permission to complain. Like there were people that were losing their jobs and there were people that were dying, they were sick. Like I'm gonna complain about the fact that like I'm a bit lonely. And in hindsight, I should have done differently. I should have said, look, I recognize that I'm very fortunate, very blessed,

but I also recognize that I'm also really lonely right now. And I think what that would have, by telling people that, by saying it out loud, you know, there's that whole theory about don't tell people your goals. I call bullshit. I think it's ridiculous. Don't tell people your goals.

I think you should tell everybody your goals because the cool part is if you have people around you that are good people they're going to hold you accountable and you may actually hit your goals way faster more effectively and it's fun to share in a celebration and celebrate someone you know who deeply wanted to do something who actually ends up doing that thing so it's funny because if you feel like you can't share with people people your goals it's really what you should do is get new friends totally i mean like why wouldn't you want to tell your friends and the people around you, you have ambitions? Well, the common critique of telling people your goals is that when you tell someone your goal, you as an individual,

you get something from that. And so the critique of it is you don't deserve anything by just saying something out loud that I think it's complete bullshit. I think if you want to do something and you tell, put it on social media in 12 months from now, I'm going to run a marathon or ultra marathon. In 10 months from now, I'm going to have, you know, $2 million of sales in my online store. In 10 months from now, I'm going to, you know, do something really challenging and difficult, especially on social media where people love to rip into each other. That may hold you accountable.

So I did not do the right thing at that particular time. I hesitated. And it's because of some weird bravado that like, I'm strong, I'm capable, and I'm fortunate. And therefore, I don't deserve to be unhappy or depressed or anxious. And I actually think my biggest lesson from all of that is vulnerability for the right people. To your point, good friends, good family, good colleagues, good partners, it shows strength. It does not show weakness. And I was very weak and I didn't want to show vulnerability. I wrote in my diary the other day that vulnerability is a magnet, not a repellent.

And I think in our masculinity, in our toxic masculinity sometimes, in our sense of wanting to be what we think strong is, the sort of misrepresentation of strength, we see being vulnerable as a repellent, as in, I will lose things. People will leave me. They'll think I'm weird or weak or whatever. And then every time I've ran the experiment of vulnerability, and when I say experiment, I mean, because it feels risky sometimes.

It's a magnet. It's like the antidote for loneliness in many respects. And there's another really important thing to say, because you were in that basement during the pandemic your family were there in the house and we often confuse this idea of being alone with loneliness totally and simon cynics actually i give him credit he came on the podcast the other day and he said he talked about how lonely he is right now and the brain goes do you have any friends he goes i have loads of friends i've loads of people around me.

I have a big team, but I'm lonely. There's an important distinction to make, which I'm sure you can speak to in your, because I was thinking, well, you had your family, had your wife, but I was like, no, Steve, you're falling into the trap again. He wasn't alone. So I was not alone, but I was lonely.

And actually this is where going back to your point earlier, which is a great point about entrepreneurship, being a lonely activity or a lonely sport, by having more people around you on the journey with you, even if they're on their own journeys, but they're sort of tangential to your journey, it's a little bit less lonely. Yeah. And if you do that across a couple different areas of your life, like if you work out at a gym or you go for runs in the morning, finding someone else to run with you is one thing,

but finding someone else to run with you who's sort of going through the same, like I want to run five kilometers and it's tough for me right now. You do it with somebody else who also wants to run five kilometers and it's tough for them too. There's an immediate connection there.

So in one case, you may be not, like you're not alone because you have someone running with you, but you're lonely. In another case, if you're on a similar journey together and you have a shared experience or you're sharing an experience that takes away from the loneliness. How does that square with Shopify's approach to

remote working? Because I've, this is a debate I've pondered over and over and over again in my head, which is like, there's no correct answer here. We all know that everyone's got a different mission. Every company's got a different mission. But one of my reasons against this total remote work scenario is because I think there's been a decay in community institutions in our world. So in the UK, like all the pubs are shutting down. We don't have community centers, churches, et cetera. Work seems to be one of those institutions that remains that does bring us together. Although that's a dangerous thing also, right? Of course. And it's also age and demographic specific. And there's a little bit of privilege in there as well because you know everyone's situation is different this is something i'm evolving on but when i'm like an 18 19 year

old just left university when i'm 21 years old and i've just left university i want to be do i not want to be around people um build connections, to build skills for synchronous work? Will I not be more lonely doing remote work potentially from my studio apartment in the middle of the city where I live in a cardboard box, as I used to once upon a time? How do you square all of that together? So the reason that we're not fully remote is because of that exact reason. We had about, I don't know, 10 or 11, something like that, offices around the world. And we were full-time in the office pre-pandemic. And now we sort of have this model, which we refer to as digital by design, which means that office centricity is over. And the reason that's important for us is that we've

been building this company out of Canada, you know, for almost two decades now. And so in every single job offer we gave, there was an asterisk that said, it's part of this offer, there's a condition you have to move to Canada. And so that immediately limited the type of talent type of people that come to Shopify. And so there's a real advantage to the fact that now you can work anywhere you want. So that's really valuable for us. First time that our new CFO is based in New York, our new GC is based in DC, our chief operating officer is down south. That is great. People can live wherever they want. However, we didn't close the offices. We converted them from quote-unquote offices to more of these

we call bursting locations, where you can come in for a burst, which is just an onsite. And we actually not only like the idea of people coming in, we force people to spend time with their teams in person at least once a quarter. And what you see is the healthiest teams may not have to meet as regularly because there's enough of a trust battery where the residue of the trust battery can be distributed. know, can be distributed. But for teams that are just forming, it is really important for them to be in person. And we really encourage that. So we're not really hybrid because it's not three days in, two days out or anything like that. It's, it just works from anywhere you want with the condition that you must spend time together with your team in person at least once a

quarter, in some cases, once every month. Every solution, every answer has a downside. For sure. Office centricity has a downside, a clear one. What's the downside in your view of that work from wherever you want, but once a quarter? It depends on if your manager really likes the idea of being in person, you're probably going to be in person more often. And if your manager does not, you may be less. So we're trying to work around that and create some guardrails there. But I don't think there's any perfect solution. A lot of companies are going the opposite way now. You're hearing like Snapchat and Twitter. They're all going, they seem to be going back to like 80% in the office, et cetera. The good news or the bad news, I don't think anyone's got this right.

And the companies that will get it right longer term are going to be the ones that are most introspective about this. What's working, what's not. Be honest about it. So we know that being fully remote doesn't work for us. We need to be in person sometimes. We also realize that it's really an amazing opportunity for someone to come to Shopify who can have an incredible role building great product or doing something at the company that's very valuable and live anywhere they want. That is an amazing opportunity. In the early days of Shopify, I moved to Ottawa,

Canada for Shopify. And that's, that's a, that's a big thing for my family. So the fact that they can live anywhere I think is really great, but I don't think anyone has really knocked it out of the park just yet. What I would also say is that just back to the Simon Sinek quote or philosophy, I think we all need, like, we may not go to church as much anymore or youth groups or, you know, organized sports. I think we all need our own version of that tribe. And I think developing your own community and your own tribe, even if you guys sit around and stare at screens and you're playing video games together, I think having these rituals, I'm not religious, I'm Jewish, but I'm not religious. But every

Friday night, we have a Sabbath dinner, Shabbat dinner. And we say sort of the very basic Jewish prayers. But this ritual that my kids look forward to, where they, you know, they say Shabbat Shalom, and my wife, you know, makes this amazing like home cooked dinner. I mean, no matter what happens, I'm home Friday nights, even if I have to travel, I'll go home and then I'll leave Saturday morning because that is a ritual that I think is important. And I think we all need rituals in our lives. And I think the cool part of rituals is like you can create new ones all the time. The key though is consistency. And the direction of travel at a very macro level with all these things that are happening in technology seems to be um one in which where we're being stripped of community and in-person connection which seems to humans aren't changing technology

is but our innate fundamental maslovian or like psychological needs aren't changing but the society we live in i think is optimizing against our um against natural connection living in you know four white walls in the middle of a big city alone, swiping on Tinder, ordering your food, using a piece of glass screen, all of these things seem to be robbing us of that connection. And I reflect on this a lot. I go, the reason why the Diary of a Seer is successful, and the reason why a lot of the things we've done have really worked well in terms of like the content and the media, is because we, without really being that intentional about it, to be honest, have created a sense of connection for people. They will hear your story about your own insecurities or about the things

you struggled with, and that'll make them feel heard and understood and connected in some way. I love that. I actually think that that is one of the most, this sort of shared experience, even if I don't know you, is really impactful. We may not know each other. We may have never met before, people that are watching. But if you, if anything that I said, anything in my story resembles your own or resonates with you, hopefully all I can, what you take from this is that,

like there is a way to get over some of these things. Some things you don't get over, you simply manage it better. But there's no, there's no one, like I have not met, I get a chance to meet pretty much anyone I want, just like you do. Nobody has it figured out.

Nobody is 100% happy all the time. No one has a great relationship, great career, great health, great family. No one has that. We're all, but the best ones, in my view, are the ones that are self-aware of what to work on. And they have tactics and tools and traits to sort of move towards a better version of themselves. They grab their surfboard when things come on the resiliency side. They're very honest about like when they're lonely, they say, I'm lonely. Here are the changes I have to make. But no one has it all figured out. And I think that in itself is what I figured out

when I had the sort of epiphany that holy shit no one has their shit together we're all trying to figure it out in our own ways it was freeing for me it's so true that nobody's there it's like a party that you're striving towards that actually nobody's at you know everyone I mean you know more people than I like the people that sit in this chair that you know are way more successful than I am I've listened to a lot of your, your, your interviews. We're all kind of working on our own shit. Yeah. Everyone is. And the ones that say that they're good. I don't know. I think they're lying on that point then. So we've, we made these cards. They're actually on sale on Shopify. We, um, we use Shopify to sell these cards and it's very much, I'm glad you,

I didn't want to say that. they're called the diary of a co conversation cards and um what we've done is we've taken all of the questions that all of our guests have left in the famous diary of a ceo all of the amazing guests we've had on the show we always ask them to write a question that helps people to to go a little bit deeper and we've made them into these cards on the front of the card you'll see the question and the person who wrote the question on the back you have a qr code scan that you can see that the next guest that had to answer it so we're really letting the cat out the bag here cool i picked three cards for you the idea is that people will buy these and then play them at home with their friends and connect because

vulnerability is the door to connection you just have to pick one sure gary neville tell me something you've never told anyone before i don't think i'm a great father i want to be a great father but i don't feel i'm a great father i feel like i only have i have like 10 units of energy and if i give units energy somewhere else then I don't give it to that and I haven't figured out the right dynamic yet and I I worry that at some point my kids will be too old they'll be out of the house and it'll be too late and um and I really want to be a great father so that's kind of it's quite vulnerable, but that's the truth. Yeah.

Is that because of your definition of what a great father looks like is maybe not fitting the great father that you are? Potentially. Do you see what I mean by that? Yeah, I do. Because you're an inspiration. So I mean, this goes back to, am I enough of a father? Am I enough? Right. But the thing about the, the, like being a great father is there is a limited time component to it. I don't know how much, like Bailey is six in 12 years. She's going to be off out of the

house somewhere. I suspect I get 12 years to become a great father. And I don't know exactly the right path to get there. I know what my weaknesses are, but they're a little bit elusive. It's, am I present with them? Am I mindful to their needs? But that's something that I struggle with. And I'd like to be, if I sort of think of a three or four elements of my life that I want to be world-class, my work, my relationship to Lindsay, my contribution to the world, my charity perspective, that fourth bucket is, can I be a really great dad? And I don't also know how to gauge that. A lot of the other metrics I can gauge. Lindsay was very clear to say, like, you're a great husband or like, you weren't a great husband this week. My work can be reflected by my performance. I don't know the stock price is exactly directly. You know, I don't think there, I think that's more correlation versus causation. But the other

points in my life, my contributions to the community, I can measure those things. I don't know if I can measure if I'm a great father or not. Because of that, it makes the whole thing really challenging. Maybe like the other things we've spoken about, this great father party is a party that nobody's at. Potentially. I've never met someone that says, I am a great father. Yeah. You may be right. Now, maybe actually the pursuit of that is in itself what I'm trying to do. As is the case with life, right? Right. Exactly. Exactly right. But by the way, even like, okay, go back to vulnerability.

Millions of people are going to watch this. And maybe there is someone who's watching that actually is like, hey, I actually think I am a great father. And here are the couple of things that I use to gauge that. One of my friend of mine who, he's not really my parent role model, but maybe he becomes that at some point. I asked him what a great father or a great parent does. And he says, one thing, independence. Are your children able to be truly independent? I thought that was really interesting as sort of a metric for gauging whether or not you've raised You you you're a good parent. Um Another one says like, you know, there's a famous quote, which is you're only as happy as your least happy child

Have you heard that right? I've actually heard the corporate version that which is like you're only successful as your least successful division of your company Which is also a really interesting way to kind of put that um, but I I that that interesting way to kind of put that. But that would sort of be the one that, I don't think I've admitted that because I haven't really had a venue to actually say something like that before. We have a closing tradition on this podcast where the last guest asks a question for the next guest. Obviously that's what becomes these conversation cards. The question that's been left for you, interesting one, because it's a bit left field, but what's a common misconception

people have about you? And more importantly, how does it make you feel? Because I talk so much about entrepreneurship, there is, I've heard this now from a number of people that I don't ever talk about the failures that I've had from a business perspective. And partially I don't do that because I don't think they're necessarily that valuable relative to some of the successes. We talk about DJing and t-shirts and Shopify. There are literally 20 other companies that I've started that have been total fucking failures. And I think the common misconception is that the stuff that I've worked on have all been not huge success,

but generally successful because I talk about them so much. And it makes me feel sometimes like I'm not, more recently, that I'm not being as helpful or honest as I should be because I just don't have, I don't have the space or the venue to talk about the slipper company, the poker chip company, the nurse uniform company. Those are all real companies that I started when I was in college or undergrad or when I was a teenager that failed

miserably. And the misconception is that I think that everything that I've worked on has turned out to be good or successful. When you look at yourself in the mirror, and I'm just everything that I've worked on has turned out to be good or successful. When you look at yourself in the mirror, and I'm just saying that as a metaphor, and then you look at the perception of you, does that create a certain dissonance or a feeling of like, I don't know, people call it imposter syndrome, which is a term I don't love. But often when you reach high places because you're involved in very successful ventures and pursuits, there's this kind of like perception which might not match the perception or the voice that whispers in your head when you're alone i have i have that as well here's another here's another way to put sort of

the the failure thing um i do a lot of tv and and um and i'll get feedback that you know that was really great i saw you on the show or i saw you do this interview or saw you on Squawk Box. And I'm like, great. Yeah, thanks. I appreciate the compliment and stuff. Sometimes I want to tell them and I don't often tell them, do you know that I put in five hours of work memorizing those data points? I think sometimes I like to pretend like it comes easy to me.

It does not come easy to me. I work really, really hard in my craft. My, if you think I'm a good storyteller, you don't think I'm a good storyteller. Like I put a lot of time into preparing for my conversation with you today. A lot of time. I've watched all your interviews.

I literally, as I told you, like I didn't finish my run until I listened to the entire Seth Rogen interview. I don't think I do. I don't think I do. I do a disservice, I think, to a lot of people. And I'm working on this already around vulnerability of actually sharing. This is not easy for me. I'm not naturally, I can naturally memorize. I don't have photographic memory. What I do have is a really good work ethic. And I should be talking more about that than actually showing my work more than just the result of my work.

And so when I look in the mirror and I think to myself, where is the dissonance? It's that sometimes, less recently, but certainly oftentimes previously in the past years, I've made it seem like this is easy for me. And it's not easy for me. And I was never the smartest kid in any of my classes. I never got, I probably made it seem like I was, you know, smarter than I was in the classes. When I wanted to do all in a class, I just outworked everybody else. And I think if you should, if anyone out there wants to emulate anything that I've done, emulate my work ethic and the journey, not the destination, because it's been fucking hard and still fucking

hard. And I embrace it and I enjoy it. And I wouldn't trade for anything else in the world, but I've had tons of failures and I work really hard to make sure that I have fewer of those over time, but it doesn't come easy to me. Harley, thank you so much. Incredibly enjoyable conversation and I've learned so much, but it's funny though, I've done so many of these podcasts and I still continue to learn

from every single individual in so many incredibly unique and for me, really defining ways. I wanted to close with just one thing because I think I'm thinking forward at the guests we've got coming up and the guests we've had previously. And maybe you're the guest best place to answer this this started as a very business-centric show

business-centric podcast started as a me as a young entrepreneur building a company etc etc there's a huge part of my audience base that are doing exactly that right now like they're like maybe they've started their Shopify store um maybe it's day one. They know what they want to sell. Maybe they don't. Maybe they're not quite there yet. But if there were a piece of advice you could lend to someone who wants to go on that journey of entrepreneurship, of all the things we've discussed today, what would that closing remark be?

Remember that the cost of failure right now is the lowest it's ever been in the history of the world. And because you, if you can remember that, it means that there's absolutely no reason why you shouldn't keep trying. And if it doesn't actually work, try something else. I think this idea of cost of failure is a fascinating one because it's never going to be zero, right? Because ultimately, like, there is an opportunity cost in your time. You could be doing something else. You could be watching TV. You could be playing video game. You could have a job. But knowing that you are interested in entrepreneurship

and at the same time in modern day, you also realize that the cost of failure is as close as zero as it's ever been means that if you have any instinct to start a business in the shower, when you're driving, when you're on a walk, randomly you have this like, this would be a cool idea. Try it. When you look across the millions of stores on Shopify, who've now sold more than half a trillion dollars on Shopify, the vast majority of them did not wake up and say, I'm going to be a great entrepreneur. They tried something. It worked. They scaled it. They tried something, it didn't work. They tried something else. That was when they scale. When you look across the stores on Shove that have been successful, all of them didn't start out with this vision of building a billion dollar company at some point.

And I think that the fact that we can start a business now for the price of a couple cups of coffee, and that business can grow to be a large, multinational, multibillion-dollar company, if that's what you want, that did not happen. And it certainly did not happen in the time span that it's happening right now. The companies now, there are companies on shop like today where they're doing a billion dollars or more in sales

that didn't exist six years ago. Six years ago, it was a shower idea. And now they're a multi-billion dollar company. Or if you don't care about building a billion dollar company, they've changed their entire vertical, their entire, their world, whatever the world they're in, they've changed it entirely and it'll never be the same again. And so. What a time to be alive. What a time to be alive. What a time to be someone who actually has an to be alive. What a time to be someone

who actually has an idea and wants to share that idea with the world. And if you're not sure about an idea, what you could sell, how you could start, think about something you already do. There is a store on Shopify that sells the most delicious matzo ball soup. What's matzo ball? Matzo ball soup is a Jewish chicken soup. It's this matzo ball. It's like, if you go to a Jewish deli, you should actually try this. You should go try. There's a store in Shopify that says matzah ball soups.

And when you look at the story of how it got there, they were just making matzah ball soup for their friends and family. And at some point they realized, maybe I can share this with the world. And they do. And now they have a real business doing the thing they already were doing,

except now someone is paying them for that. That is incredible. And that's the time we're living in right now. What a time to be alive. Harley, thank you so much for your time and your generosity. It means the world to me. And it's been an incredibly important conversation. Great conversation. Thank you.