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

23:19And 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 made me flashbacks for conversation I had with Jimmy Kauai. He said, we don't need more people that are shit at physics. Find the thing you're going to 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? So this is going to be a long way to get there, but I think it's important.

23:53When I was building that t -shirt business in college, a mentor of mine, his name is Philip Rimer. He's a senior partner at a very prestigious law firm called Dentons. 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, not to become a lawyer. He's like the skills that you need given what I think your ambitions are around business creation, business building entrepreneurship. You are lacking some sophistication. You're always going to struggle with these sort of things.

24:29He's like, but I have this idea, which is go to law school, not to get good grades necessarily, not to get, not to become a lawyer, but to effectively selfishly disseminate all this information from your classes to make you a better entrepreneur. And I think because I sort of had a very clear view that 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 of 21. I thought this teacher business would just be the thing I'd keep doing for many more years.

25:02But 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 operatives, something that existed, no one is looking at, but that I can take advantage of. Something unique. Is that what you say? 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 to not be a lawyer, but to be a better entrepreneur.

25:35And 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. You could have gone, like Steve Jobs did that typography class. That's right. And that's where we have these incredible devices in front of us. That's right. So it's an obvious 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.

26:04But now in hindsight, when you think about it, you're like, well, that makes total sense. Look, I went to public high school and it was good school, but 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 factim's and memo's all day long. I learned how to negotiate and how to do the real critical debate and critical reasoning. I learned how to read 2000 pages and pick out the one line that matters. All these things on their own doesn't seem like it would create the curriculum of a great long -term entrepreneur. But it did.

26:38And 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.

27:08I 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 point? Is this going to make me a better entrepreneur? And I think if I would have realized that 10 or 15 years later, 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.

27:42I think this is an exceptionally undisputed 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 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 a few just in the top 10 % at six complimentary skills, you're the best in a village at that particular thing.

28:19Like 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, the best shooter in the world. He doesn't take the best free kicks in the world, doesn't head the ball the best in the world. He's considered the best player in the world by many because he indexes high, the top 10 % at various things. I think about Jack, he records this podcast. Now, if Jack was a, 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, the place to be placing your time to become the best in the world.

28:54As we saw in the case of Steve Jobs, he went into typography and design and then made these beautiful devices. Jack should probably go and try and get an unobvious, but 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, or DJing, if you went and learn to be a DJ, then he would learn about stems in music and whatever else. Or set design, if you went and did a theory. So it's and that would make him be, I'm not using job just saying someone is Jack's position.

29:31That would make them be a real fucking hard to find talent. But it's funny because we can in industries like always think this about code is and I don't hate to swear generalize here, but it probably doesn't look 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, 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.

30:05Sure. And actually, the numbers of two points. One is most people start companies with people just like them. Yeah. 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 faculty arts or the faculty of philosophy, or the faculty of engineering, and find someone they're sort of company with.

30:33I think some of the best partnerships and relationships that I've seen that have built things that are that change the world from a company perspective, film, film, thropically, whatever they're trying to build might be. Building with other people with complimentary 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 DJ DJ like hundreds and hundreds of bar mitzvahs over my time hundreds. I never appreciated what I learned as a DJ and how I applied to running a large public company.

31:10But 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 or 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.

31:39So now before I go into any 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 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 a rap or something like that, top 40. Like, you can see glimpses of that.

32:11You try one song. You see how people watch their faces, how do people resonate? Oh, they really like this on great. I'm going to go like, mo money, mo problems from Tori's BIG and the whole crowd rubs. 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 where the 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, please get up in your chairs and take the time steps forward because the father of the bride is going to say a few words.

32:47And everyone gets up and comes out 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, but find better strategies for getting the thing accomplished. I learned all that in Dejing and I can apply all that to running a large public company today. When we start businesses and stuff, go back to that point again, 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.

33:20Then, like, 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 the hobbies are again deducted toys or games. Yeah, yeah, yeah, I mean, look, I mean, this is what a polymath is. A polymath understands a lot of different areas of the world or comprehensiveist understand a lot of there and pulls those different things in my what's the polymath?

33:58Polymath 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 is one. My wife started an ice cream company in 2016 after we had our first daughter after our first child. My wife really wants to start an ice cream shop in our 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 things like accounting or accounts payable accounts receivable or helping her procure ice cream from the ice cream makers.

34:30That 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 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 ringing so much more coffee, but I was by myself at home way more like double or even triple the consumption. And my best friend, who is 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 and replace your coffee with really great green tea.

35:11I 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 shop. And I think this tea thing, I think most people's experience with tea was like someone getting like, yes, gift basket. And there 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 firebally. And both, both those things were sort of hobbies in my life.

35:38There 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 of shop. I so much more valuable. I understand pretty much every feature and functionality the shop light 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 of shopify.

36:11And it's just a hobby. There's something really, really powerful in that because when we, when I start this conversation, I ask you why people don't take the leap. And a lot of the reason why I think is because we talked about this psychology is when I think about starting a business like a tea business or any business. I'm still at the bottom of Mount Everest looking up thinking, Jesus Christ, like I've got to find a website. Like 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? What's the packaging? I need to do branding and I need to do all now.

36:43And and also there's this other thing which in our minds, we think of success as being me making millions or me making the ton of money. What what I almost heard as you're telling that tea story was like, have this passion. Remove the expectation, which so David Brails would told me that really well just remove the expectation if you have ever been anything more than a hobby. And just get going and you'll you'll stumble forward along the way and and that's okay. I think if more entrepreneurs could see that Mount Everest is just a bunch of pebbles. And there's and remove the timeframe where possible remove the expectation of huge success and just stumble forward through the process.

37:18We'd have so many great great more businesses that we do now and everyone listening to this has that they have the hobby they have the they love tea or they love I know coffee or match or whatever it is. That perspective change of like, okay, well today I'm going to start my shopper. I still tomorrow 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 and we hope you can see what we get to in 10 years. Most people on Shopify don't register their business until weeks after they sent up for Shopify. So most people don't even assume they're going to need to register a business and that's okay.

37:50And it's not to say that every idea you have in the shower needs to be commercialized needs to see the light of day. But if if there's an idea you have the shower and you're having it a couple days in a row, try it out. Like, I mean, this isn't a pitch for shop of I but like it's it's less than a couple Starbucks coffees to go start a business today. And if you fail the cost of failure, this is close to zero as it's ever been. You don't have to take a low enough. 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.

38:22But 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, you know, 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 going to be a huge success. So it's kind of the perfect time to get started, whether you're in high school like with my DJ business or in college with my with when I sold t -shirts. There was very little expectation. I mean, no one thought it was going to be successful anyway.

38:56And you still want everyone clapped. Yeah, they're like, great, you're that's so cool. You have a business. No one asked me what my revenue is. No one's asked me what my Ibit of margins. I think it is a lot easier to get started on a business when you're in school or you're where you have a job. And this is sort of your side hustle. The amount of people shop I right now is about 10 % of all e -commerce in the United States in place 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.

39:30It was Heather and Shrinas sitting at a coffee shop not too far from here with a friend of theirs. That was a doctor who's wearing these hospital scrubs that just looked like shit. They're like, we can do this better. That's a fix was born. It was Ben Francis who said, why is there no clothes for just regular gym people? Either it's like gym rat stuff like bodybuilders or it's yoga. And that was the that's how Jim Shark came to the world. Or it's Tim and Joey at Albert saying, why is there no really great sustainable sneaker that feels good, that's washable, that costs this amount of money? That's how Albert got started.

40:01So most no one had this massive 80 page business plan and then got started. That's not how business 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 try this other stuff. And that's how you build companies that are long -lastic that changed the fucking world. And that's how shopper fight 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.

40:32And he looks around and he sees snow everywhere and he says, I'm going to start a snowboard company. In 2004, there's two ways to sell a product on the internet. One way you sell in a marketplace, which is very cheap, very inexpensive. Like a bank 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.

41:05And the snowboard shop was called snow devil. And very quickly, people started asking him if they can use a software to sell their own products and he decided snowboard store was a good idea. The software behind it was a great idea. And that was how shopper 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 you shopify in 2006. And then you were the first non technical employee as well. That's right. Yeah. A couple years later, after law school, I called him and said, I want to join you in a small handful of engineers.

41:36Smartest people have ever met in my life still to this day. And said, let me, let me be your Swiss Army knife. Let me come in. I don't care what you call me. I'll be sales, I'll be finance, I'll be marketing, I'll form partnerships. I'll do 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, 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.

42:07And here we are today, you know, it's worth $10 billions or whatever. I want to zoom in on a particular thing, which is at that time, because I hear this all the time for a bunch of people. And it's one of the barriers for them starting is, well, someone's 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 it probably better capitalized. Better capitalized more people. More information. Yeah, smarter, yeah, all those things. And it never has mattered.

42:36And I can't quite articulate why it doesn't matter. I can 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 is a really big company. Yahoo stores existed. There were companies called Magento, which isn't 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 some and 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.

43:17That 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 art and crafts, like an Etsy kind of style or as for big companies, IBM, SAP Oracle, had competitors there. Yahoo stores focused on 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.

43:58And 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, cross different markets? What if we create sort of a bank account to help them manage their cash flow? Over time, it's 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.

44:31And 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. 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 future. And just do it better. I mean, this could have sound trite, but having deep empathy for how merchants and how your customer uses your product is very, very important.

45:07And 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. And they were, you know, hegemonic incumbents. It's great. I love that we have staples. And I love that we have spanks. And I love that we have, you know, black and decker and Mattel using Shopify. But those are companies that were already successful before they started using Shopify.

45:44The stories 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, it just works from out 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.

46:16And they decide to either shut it down or they decide to pivot to different businesses. We're okay with that. We're not changing the physics. We know that most small businesses will not be multimillion our 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. And 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 times, you are not overwhelmed.

46:47And I think we are very hard in ourselves. And that's the right time. We're hard in ourselves that we really want to continue to push the envelope. Here's a very simple example. Everyone right now is talking about AI. Everyone's talking about, obviously, ChachiBT 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 be cool if AI helped merchants write product descriptions.

47:20So you put in your product photography or some meta tags. And ChachiBT helps you write a product description that will convert better. That is really practical. Obviously, in Web 3, 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?

47:53I have a bit of a Moby Dick story. My Moby Dick in terms of Shopify, the one brand merchant that I 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 every 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.

48:33Most companies would have shot 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 a, there's a great book by NISTEMTEL, I've called Anti -Fragile. I remember 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.

49:01There's the fragile system. I take this glass. I drop it at 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 rebuild 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 called pain, call a 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.

49:40Really 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're bringing to its traffic. So that provider is never going to have incredibly sexual podcast, sexual 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. Yeah. So we moved to a different someone else that could host us because they said that we had too many downloads.

50:10You have too many debt 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. We were costing them too much money. By the way, most companies are like that. They fire customers that pull them in in different directions as opposed to the best companies embrace that and they come break our stuff. It's going to make us better. If you believe, like, and by the 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.

50:44Do I wish it? Those things wouldn't have happened potentially. I mean, in hindsight, I wish I would have had less anxiety, maybe. But maybe I would be sitting here with you, Steve, today, if those things wouldn't have happened. It's 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, we're going to, 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.

51:11You'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 do you, how do you create that culture, that foster that sense of like resiliency and positive attitude towards change? 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 some of 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, had had something happen to them that allowed them to build resilience on their own.

51:44Some of them, you know, cracked, but others actually, it's like, you know, the metaphor that I love to use is like a huge tidal wave is coming. Some people grab their surfboards and some people run for the beach at the towel. I like to surf where people. The surf where 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.

52:20And actually, rather than doing their own ventures, we are collectively coming together to build something much bigger together, like 1 plus 1 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. Let's 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, anyone I met, where do the entrepreneurs hang out?

52:51And 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 up when you're building your company, you're trying to create a culture that is super effective that has, it looks for the alpha opportunities that is very ambitious, that works hard.

53:26And I think that's what we've done. And I think we've got 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 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 entrepreneur way to do it. The non -autchppin 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.

54:00Most 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 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 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.

54:33And they set that philosophy. This is who we are. We care about the bookshelf being the same, the 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 will come to culture. If they went somewhere else, they probably behave differently. But that comes down to the culture just being absolutely crystal clear and the hiring of that culture being disciplined and the firing. 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.

55:09And 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, famously, Paddy McCormick created what's now famous. It was the Netflix culture guide. Yeah, I remember reading. 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 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's just it's very honest about this is the type of place.

55:42I think one of the one of the funniest lines in there was mediocre performance will lead to superior severance. I love that, right? Super, super cool. So there's there's that aspect, which I think 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 days where, you know, like there's a photo that floats around every now and that of me sweeping the floors.

56:21I get it. There's that was kind of romantic that we sleep the floors ourselves. But I actually think over time you can have a fan if you 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 be 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 like pull the product in a really unique positive way.

56:55That'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 when I speak about culture, I think I'm kind of using the word interchangeably with the word in that particular case, maybe the word values. But let's if we think about company culture in the context you're describing it. I was doing some writing over new years and I was looking at the life cycles of companies and they often start like cults. And I went through I think IBM Instagram all of these huge companies.

57:29And 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 down with the little cult and they like help in that growth phase. And then they get to kind of 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.

58:00Now 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, he's words to the effect of the start should resemble a cult. Do you believe that I something I've pondered because the word cult is such a toxic words to be careful. I mean, I, I, yeah, I don't know much of culture 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 place where I can do my best work is because the mission is not interesting or cool or it really hits home for me.

58:46I'm not something to say that I wouldn't be a good, 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 the end of the day, the mission of the company, even if you add all types of rose petal glasses and you say, well, we're not, we're not selling cola.

59:18We 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 every, at any stage, really hits you hard, that's probably the company you should go work at. And you probably say that for a very long time. And even the fact that not every, not every person needs to say 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 fun.

59:52But 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 shop I didn't exist, I probably would be doing something around encouraging more entrepreneurship, inspiring more entrepreneurs, creating tools that help entrepreneurs start to work. And I think that's a good thing about scale and build faster. I just found this, this vehicle that does it way more efficiently that I ever could do on my own. It's called Shopify. So you damn right. I'm going to be wanting to be on that bus or that rocket ship. But I don't think it is anything to do with what's on the wall.

1:00:23I think it has to do with the fact like, what is the company actually doing? If you strip away all the marketing speak and all the brand speak, what is the point of the company? What's the objective? And I think that's that really matters. 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 telling your hobby into a 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.

1:00:55So 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 to order earlier on used to add 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 to tell a 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 T from? How would you recommend an entrepreneur solve the information problem?

1:01:30And 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 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 perceived to have really great relationship with their spouses. And I went through the list and I kind of laughed as like, okay, like, am I really going to ask that person to my mentor? Like, I don't really respect that person in any other avenue in their life.

1:02:05So like, why would that person be my mentor? So I went through this list and I realized, you know what? I'm doing this all wrong. If I want to be a really good husband, a really good father, a really good leader of Shopify, I want to be a really good human being from a charity or philanthropy perspective. Instead of trying to find one size fits all like one person that's all those things where it all comes together, it would be so much better for me actually to just focus on verticals. So in the vertical of parenting, who's someone that I think that's a really good job on parenting? Three or four people, I'll give them a call.

1:02:36The neat part of it doing in that way as opposed to saying, by the way, the person that like, I can't really be sharing this, but this is kind of funny. I told you about a mentor in mind that can be going 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. Maybe your divorce mentor maybe. Yeah, but he's really good about understanding skill set or skill stacking as we talked about. There was someone that I called when I was about to get married to Lindsay, who I just felt had the most special relationship with his wife.

1:03:08And 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 that's important is because like that like a video game or like any skill said, you can't be good at everything. And so I'm able to derive different things from each of these mentors and then create my own version of it. But the second reason it's so it's 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 in other aspects of the life, he's not someone who I'd want to who I would admire.

1:03:50And so the way that I've always thought 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 is really only valuable for newborns. And it turned out that a couple years, you know, as the kids grew, it wasn't 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 square to my philosophy on mentorship more generally.

1:04:22I think there's sort of two sides. So you've mentorship on this side, which is like people you want to emulate. But there's also the sort of the tribe side of things. 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.

1:04:54We 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 there everywhere. But finding them used to be really difficult, actually now it's much easier. Go to Reddit, look on YouTube. Like, you can literally go, 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.

1:05:28You can find those people either online or in person, and you can build yourself in informal board of directors when you're getting started. Now, if one of you eclipsed this the other in terms of growth, you're probably not going to find as much value from that particular tribe as you, as you previously did. You're going to want a different tribe. But if you do this over time, you actually end up with far more, the, the acquisition of information gets much easier over time. And I don't think enough people take advantage of that. If I gave you, 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 shopper by customers.

1:06:08Who 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 other, 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 YouTube channel.

1:06:48And they want to, they want to expand their monetization. So they do something like they make t -shirts with, you know, the director of CO 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 Burlant. 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.

1:07:31She 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. 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. Would Jimmy did with like Beast Burgers or with festivals? Mr. Beast. Mr. Beast did with, with, with Beast Burger or Beastables. He didn't just go and go to a chocolate company and say, I want to create a Mr.

1:08:07Beast chocolate bar. He went, he loves chocolate. He loves chocolate. He loves chocolate. He loves burgers. And he said, let's create a better burger than I can get right now in 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. Those, I would definitely put one of those millions of dollars into the hands of a creator who's on the precipice, a 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 and already exists.

1:08:41But 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 nichey. 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 Perse. James Perse 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.

1:09:16And I would say, go do more of this. Because I actually, now I don't know my 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 makes other clothing, but he has a ping pong table. I'm not joking that he makes, which is the most beautiful ping pong table he's ever seen. He has a couple of these sort of villa rentals in Mexico, which he designed himself.

1:09:52But he's one particular vertical that I think is really, really cool. Maybe the third thing that I would invest in. So Conti Creator be first, someone like James Perst, who does one vertical really well, 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 sure SM7B. And from everything I've read, because I like this type of stuff, it is one of the greatest pieces of engineering, audio engineering ever created, which is why sure who makes the microphone hasn't really changed much.

1:10:26This 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, some more people can try their hand at podcasting, that would be really cool too. Interesting. Making the quality more accessible to the masses, right? That's right. And I don't just mean like there are other good microphones out there, but you know the difference between the 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 good to sound repetitive, but it's resiliency.

1:11:07I'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 are, that grab the surfboard are optimistic. I want people that are hard working, but I find generally the people that grab the surfboard are also hard working. 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 ten million dollars, or a hundred million dollars, they would still do the exact same thing the day later, because that is their mission, that is their life's work.

1:11:37And 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 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 either the surfboard people, because I think surfboard people are deeply important. But curious and deeply ambitious. We spoke to your team and asked them what you in particular were good at. Oh God. They, they, 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?

1:12:07And 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. We, I heard the gasp, but backstage here. Someone in, probably couldn't hear that on the mic. But everyone, everyone that like works closely on the on my team are also all entrepreneurs themselves. They all have side houses. Oh really? Yeah. No, they said lots of many, many amazing things about you. Many, many amazing things. The one that I wanted to focus in on, because I can quite, 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.

1:12:43What, what an earth does that mean? I calendar everything. Well, they made it sound much better. Maybe they should be the story type. I mean, I truly, like, before I came here, I wanted to grab a quick coffee. That was in the calendar. My, my meditation this morning is in the calendar. The things that I really, really care about, I die rise. 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 are like, they're always kind of in a rush.

1:13:19Me? 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 diarizing or, you know, scheduling, I don't know, like a lunch. I, I, this is going to send, 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.

1:13:52Everything is in the calendar. Every person, someone that I want to hang out with, that I want to actually, I'm meant to remind 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 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 like nice to have in my life. I don't do the nice to have thing. These are things that are in my life are must -haves.

1:14:24And Shopify is very important to me. Lindsay and the girls are very important to me. Like some of the charity projects we're doing, particularly some of the, 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 do research on some other topic. Like this is kind of the stuff that matters. And so when we, when we, when we first, when 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, Ike guy?

1:15:04Yeah. Yeah. So when I think about the Ike guy 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 the term life's work. But what am I good at? What is the world going to find value in? What kind of get paid for and, and what, 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 the end 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.

1:15:36It was obviously, 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 Ike guy spectrum or on the life's work spectrum? I think that's why they say that. Q1 is often when businesses start implementing new systems and processes in hopes of creating efficiencies for the year ahead. And over the course of my career, I've learnt just how crucial having the right systems in places, one which has helped me across many of my investments is NetSuite. They're also a sponsor of this podcast. NetSuite is the number one cloud financial system through their streamlined platform.

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1:16:46That's NetSuite .com slash Bartlett. 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 on energy. I was high in anxiety and I wasn't making time. I 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.

1:17:28We were always by ourselves. We were fully remote at that point. And 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, with virtual coffees.

1:18:03I 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 a 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 head count.

1:18:39Like all these different teams reported up to me. From a head count perspective, there were like 6 ,000 people that reported to me. It was kind of a crazy thing. And, but I knew it wasn't the right job for me. But I did not have the confidence, self confidence. Nor did I have the 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 be, you're not going to have 6 ,000 record ports.

1:19:10But rather, you're going to have a couple hundred record ports, 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 doing the same thing, which is grabbing as much as I can, trying to like Swiss Army and stuff. But I never kind of settled in to say, where do I actually want to do?

1:19:42Like, what is my craft here? I always love 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 to do this rest of my life. I don't like it 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 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 river stone.

1:20:24In 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? Um, no. I don't think I was... 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 my max here, right? I mean, I've been here 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...

1:21:00The thing that I really want to do is also the thing that everyone else really wants me to do. And so it's really the thing that is most valuable to the company at this particular place. For yourself, Sistine, that enough. But that's not enough. Yeah. Am I doing enough? Am I contributing enough? And what does that mean about me and myself? That's right. Obviously, I'm not enough. I'm the happiest. I'm not just saying that because Ron Cameron, 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...

1:21:32I'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 head count. And most of them 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 I'm like, do I feel like I'm growing? I feel like I'm actually contributing both to the company, but also to my own developments. 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.

1:22:12Again, you can just do what you want. Like, if I want to, like, if I just want to be the chef at Shopify, it's not really good at much value. But if it turns out, and that the Vendigarm over up, what am I really good at? What does the company value for me? And what is something that is uniquely in my skill set? Wherever the Vendigarm 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 or wife or partner to say, listen, I'm struggling here.

1:22:56And do we do it after? Do we do it during? When did you do it? I didn't wait too late. I waited too long for that, and I wish I hadn't. I think it would have saved a lot of grief.

1:23:07I 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 little 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, yeah, that I had enough permission to complain. Like, there were people that were losing their jobs and there were people that were dying.

1:23:40They were sick. Like, I'm going to 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 had, 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. That's bullshit, that is. 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.

1:24:14And you may actually hit your goals way faster and 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. And I mean, 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.

1:24:41And 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. Special in 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.

1:25:09I 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 depress 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, this sort of misrepresentation of strength, we see being vulnerable as a repellent, as in I will lose things.

1:25:56People will leave me, they'll think I'm weird or weak, whatever. And then every time I've ran the experiment of vulnerability, and when I say experiment, I mean because it feels a little risky sometimes, it's a magnet. Almost always. It's like the antidote for loneliness in many respects. And there's another really important thing to say because you are 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 Sinek's 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.

1:26:28And the brain goes, do you not have any friends? He goes, I have loads of friends. I have 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. Because I think in where you hedge your family, hedge your wife, then 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.

1:27:03Yeah. And if you do that across a couple of different areas of your life, 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 stuff for them too. There's an immediate connection there. So in one case, you're not alone, because you've someone running with you, but you're lonely. In other 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.

1:27:36How does that square with Shopify's approach to remote working? Because this is a debate I've pundit 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 and community institutions in our world. So in the UK, like all the pubs are shutting down. We don't have community centers, churches, etc. Work seems to be one of those institutions that remains that does bring us together.

1:28:07Although that's a dangerous thing also. Of course. And it's also age and demographic specific. And there's a little bit of privilege in there as well. Because everyone's situation is different. This is something I'm evolving on. But when I'm like an 18, 19 -year -old, just left Univertnik. When I'm 21 years old and I've just left university, do I not want to be around people to 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?

1:28:46How'd you square all of that together? So the reason that we're not fully remote is because of that exact reason. We had about 10 or 11, some of 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 centrality is over. And the reason that's important for us is that we've been building this company out of Canada 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.

1:29:21And so that immediately limited the type of talents of people who have come to Shopify. And so there's a real advantage of 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.

1:30:02And 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. 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 just work 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.

1:30:34For sure. Office of interest, he 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's not, 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. Are you hearing like Snapchat and Twitter? Twitter. Yeah. They're all going, they seem to be going back to like 80 % in the office, etc.

1:31:05The good news of the bad news, I don't think anyone's got this right. And the company is that we'll 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 that the company is very valuable and live anywhere they want. That is an amazing, I, you know, in the early days of Shopify, I moved to Ottawa, Canada for Shopify.

1:31:34And that's a big thing for my family. So the fact that they can live anywhere I think is really good, but I don't think anyone has really not to have 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, 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.

1:32:12But 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.

1:32:43And the direction of travel at a very macro level with all these things that are happening in technology seems to be one in which where we're being stripped of community and in -person connection, which seems to humans aren't changing, technologies, but are innate fundamental mazlovian or like psychological needs aren't changing. But the society we live in, I think, is optimizing against our against natural connection, living in, you know, full 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 rubbing us of that connection.

1:33:19And I reflect on this a lot. I go, the reason why the driver's here 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 hard 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.

1:33:46Yeah. It's 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.

1:34:21Like really, 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 are very honest about that, like when they're lonely, they say, I am lonely, hear the change they 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 this sort of epiphany that holy shit, no one has their shit together, we're all trying to figure it out in our own ways.

1:34:55It 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 are way more successful than I am. I've listened to a lot of 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 made these cards. They're actually on sale on Shopify. We use Shopify to sell these cards. And it's very much, I'm glad you said, I didn't want to say that.

1:35:31They call the Diorevasio Conversation cards. What we've done is we've taken all of the questions that all of our guests have left in the famous Diorevasio. All of the amazing guests we've had on the show. We always asked them to write a question that helps people 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 count 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.

1:36:05You just have to pick one. Sure.

1:36:10Gary 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 like 10 units of energy and if I give you energy somewhere else, then I don't give it to that. And I haven't figured out the right dynamic yet. And 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 I really want to be a great father. So. That's kind of it's quite vulnerable, but that's a truth. Is that because if you were definition of what a great father looks like is maybe not fitting the great father that you are?

1:37:02Potentially. Just what I mean by that. Yeah, I do. Because you're an inspiration. Am I, so mean this goes back to am I enough of a father? Am I enough? Right. But the thing about the being a great father is there is a limited time component to it. I don't know how much like bailiast 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 my present with them. I'm mindful to their needs. But that's something that I struggle with.

1:37:45And I'd like to be, if I sort of think about three or four things, I'll answer my life that I want to be world class, my work, my relationship to Lindsay, my contribution to the world, charity perspective, that fourth bucket is, is kind of 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 that's more correlation versus causation.

1:38:21But 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 is 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 isn't itself what I'm trying to do. As is the case with the 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.

1:39:03And maybe there is someone who's watching that actually is like, I actually think I am a great father. And here are the couple of things that I use to gauge that. Interesting. One of my friend of mine who he's not really my parent, Romano, but maybe he becomes at some point. I asked him when a great father, 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're a good parent. Another one says like, you know, there's a famous quote, which is, you're only as happy as your least happy child.

1:39:41If you've heard that, right? I've actually heard the corporate version of that, which is like, your only successful is your least successful division of your company, which is also really interesting way to kind of put that. But I 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 with a last guest. Ask a question for the next guest. Obviously that's what becomes these conversation guards. The question that's been left for you, interesting one, because it's a bit left -field.

1:40:10What's the common misconception people have about you? And more importantly, how does it make you feel?

1:40:19Because 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, which I 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.

1:40:59It 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 the space for the venue to talk about the slipper company, the poker chip company, the nurse uniform company. Like those are all real companies that I started when I was in college or undergrad or when I was in college. 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 that's the understanding 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 time I don't love, but often when you become, 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.

1:41:57I have that as well. So here's another way to put sort of the the failure thing. I do a lot of TV and and I'll get feedback that you know that was really great. I saw you in the show where I saw you do this interview or saw you on on on on SquawkBox. And I'm like great. Yeah thanks. No, I appreciate the common stuff. Sometimes I want to tell them, 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. If you think I'm a good storyteller, you don't think I'm good storyteller, like I put a lot of time into preparing for my conversation with you today.

1:42:42A 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 Rogan interview. I don't think I do have I don't I do a disservice, I think, to a lot of people. And I'm working on this already, a round vulnerability of actually sharing, this is not easy for me. I'm not naturally I can naturally memorize. I'm not 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. So when I look in the mirror and I think to myself, where is the dissonance?

1:43:15It's that sometimes less, less recently, but, but certainly often time, 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 smarter than I was in my classes. When I wanted to do on a class, I just outworked everybody else. And I think if 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 I wouldn't try anything else in the world.

1:44:00But I've had tons of failures and I work really hard to make sure that I fewer of those over time. But it doesn't come easy to me. Holly, thank you so much. Incredibly enjoyable conversation. I've learned so much. But I've, it's funny that I've done so many of these podcasts and I still continue to learn from every single individual and 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 guest we've got coming up and the guest 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.

1:44:37Started as a me as a young entrepreneur building a company, et cetera, et cetera. 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. 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.

1:45:13And because you, if you, if you can remember that, it means that there's absolutely no reason why you should 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.

1:45:47Means 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 one, they scale. When you look across the stores on Shopify that have been successful, all of them didn't start out with this, this vision of building a billion dollar company at some point.

1:46:24And 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 multi -billion dollar company. That's what you want. That did not happen. And it's certainly not happening in the time span that it's happening right now. The companies now, there are companies on Shopify 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.

1:47:08And so... What a time to be alive. What a time 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 mutzabal soup. Mutzabal soup is a Jewish chicken soup. It's just mutzabal. It's like, if you go to Jewish Delhi, you should actually try this. There is a store on Shopify that says mutzabal soups. And when you look at the story of how it got there, they were just making mutzabal soup for their friends and family.

1:47:40And at some point, they realize 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 it right now. What a time to be alive. Hi, Lee. Thank you so much for your time and your generosity. It means a world to me, and it's been an incredibly important conversation. Great conversation. Thank you for inviting me.

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