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

26:18I 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 have not discovered yet. And so on that spiky point, I think the sooner you figure out that spiky point, you don't have to be precise. I didn't know I was going to run a software company, but I knew that entrepreneurship was deeply important to me. And so as I made decisions starting at 21 years old, every decision was under the lens of, is this going to help sharpen my point?

26:51Is this going to make me a better entrepreneur? and i think if i would have realized that 10 or 15 years later um it still would have been fine but it may have not have happened as it wouldn't have happened the same way and it may have not led me to join a group of you know a handful of really smart engineers building this crazy piece of software called shopify 14 years ago i think this is an exceptionally un underspoken about point which is this idea of like skill stacking but stacking skills that are unobvious and rare within an industry so if we take i think we should go through this in a little bit more detail because i think it can really have a profound impact on people i read about how um the best people in the world i think it's a mathematical equation where if you're the best at six skills in an industry that are like unobvious you actually are the best in a million people at that thing so i mean if there's a village of a million people and they showed this little graph i remember seeing it and writing about it a little bit where if you just if you're just in the top 10 at six complementary skills you're the best in the village at that particular thing like cristiana Ronaldo, the football player, he's not the best.

27:52He's not the fastest player in the world. He's not the best shooter in the world. He doesn't take the best free kicks in the world, doesn't head the ball the best in the world. He's considered the best player in the world by many because he indexes high, the top 10 % of various things. I think about Jack who records this podcast. Now, if Jack wanted to be a podcast director, what all podcast directors or producers do is they'll go learn how to do microphones and cameras. Now, interestingly, I don't think that's the the place to be placing your time to become the best in the world as we saw in the case of steve jobs who went into typography and design and then made these beautiful devices jack should probably go and try and get an unobvious but a skill that would be in high demand and low supply in this industry so if jack went into theater he would learn maybe about how to construct a story arc or if he went and did like i don't know set design also yeah or djing he went and learned to be a dj then he would learn about stems and music and whatever else or set design if he went and did a theory so it's and and that would make him be i'm not using i'm just saying someone in jack's position that would make them be a real fucking hard to find talent but it's funny because we can in industries like i always think this about um coders and i don't hate to sort of generalize here but it probably does sound like a generalization um it's sometimes hard to find someone who can code who's also an exceptional storyteller and visionary.

29:22Often in companies, they're two separate roles, right? So if you're a coder, instead of becoming even better at coding, for example, going and doing those little like public speaking sessions is probably an unbelievable hack because then you can build and sell. Sure. And actually that brings up two points. One is most people start companies with people just like them. Most people start companies with people that they would have been friends within 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.

29:55Walk across the street, go to a different faculty, go to the faculty of arts or the faculty of philosophy, go to the faculty of engineering, and find someone there to start a company with. I think some of the best partnerships and relationships that I've seen that have built things that are, that changed the world from a company perspective, philanthropically, whatever they're trying to build might be. Building with other people with complementary skill sets is incredibly valuable. In fact, I think you get a much richer set of stacking of skills. You mentioned DJing in terms of skill set. I never appreciated ever how important my experience DJing.

30:32I DJed like hundreds and hundreds of bar mitzvahs over my time, hundreds. I never appreciated what I learned as a DJ and how I apply to running a large public company. But the truth is there's all these different things. So for example, something I noticed early on, it's like 14 or 15 years old. If the pre-meeting went really well with the client, no matter how the party went, it was going to be a great result. Because if 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.

31:06And they were on your side. And they were on my side. There was this immediate connection. And so now before I go into any, any, you know, serious negotiation, I try to get to know the person on the other side of the table. I try to find some common ground. We're both dads or both parents or both, you know, whatever. We're both from the same place. That's the first thing. The second thing is read the room. So one of the things about DJing you have to do is you have to read the audience. And if the audience, you know, is clearly, if you're, if you're playing disco and no one's dancing and you got to make, you know, like a hard right into hip hop or rap or something or top 40 like you can see glimpses of that you try one song you see how people you watch their faces how do people resonate oh they really like this song great i'm gonna go like mo money mo problems from notorious big and the whole crowd erupts things like that really do make a difference um you know there is instead of asking people to get up from their chairs and come onto the dance floor which is an awkward thing to ask people to do after dinner, instead have something in the middle of the dance floor that people want to see.

32:06So maybe, for example, one of the people that is hosting makes a speech and you say, ladies and gentlemen, at this point, please get up in your chairs and take 10 steps forward because the father of the bride is going to say a few words. And everyone gets up and comes on the dance floor. And then when that speech is done, everyone's already on the dance floor. And so finding these hacks and these sort of ways to not manipulate, but find better strategies for getting the thing accomplished. I learned all that in DJing and I can apply all that to running a large public company today. This, you know, when we start businesses and stuff, going back to that point again, like we tend to go deep on the subject matter.

32:42But what I've heard from that is our hobbies and the things and the curiosity we have outside of the area that we're building in is equally important than like if I'm building a, I don't know, if I'm building a, I'm building mugs for people to drink tea out of. Much of my inspiration will come from all the other things I do in my part. And the problem is we kind of deprioritize that part of our lives to focus on this thing. But taking a step away from the painting allows us to see the picture a bit clearer and also to create that picture a bit clearer, which I think is a conversation people don't have enough because they think their hobbies are, again, deductive.

33:15Toys or games. Yeah, yeah, yeah. I totally agree. I mean, look, I mean, this is what a polymath is. A polymath understands a lot of different areas of the world or a comprehensivist. Understand a lot of it and pulls those different things in. What's a polymath, sorry? A polymath is someone who knows a lot about a lot of different things. Okay. Now, there are two things that I've done that were hobbies that ended up being hugely valuable. One, my wife started an ice cream company. In 2016, after we had our first daughter, after our first child, my wife really wanted to start an ice cream shop in our neighborhood.

33:47There was an ice cream shop. And so it was clear it was her business, not mine. She was very clear about that. She wanted independence. But even just helping her on things like accounting or accounts payable or accounts receivable or helping her procure ice cream from the ice cream makers. That was super valuable because one, it built huge empathy for the people that you shop that they're starting out. And the second thing I did was during the pandemic, I was all by myself. I'm an extrovert, as you probably can tell. My anxiety had increased to a degree that I had not felt in many, many years.

34:19And what I realized was I was drinking so much more coffee when I was by myself at home. Way more, like double or even triple the consumption. and my best friend who's a sort of a tea you know tea guy loves tea said to me I'm gonna actually get you to stop drinking coffee in the afternoon and replace your coffee with really great green tea I wasn't really a tea drinker and so David started to bring me this great tea and at some point I was like you know David I want to actually experiment with more of the features on Shopify and I think this tea thing I think most people's experience with tea was like someone get in the gift basket and it was some bunch of crappy tea in there I was like people don't know like about this really great tea.

34:59They don't know how to make it. They don't know what to use it for, when to drink it. And so we created this little tea business called FireBelly. And both those things were sort of hobbies in my life. They were sort of Sunday afternoon activities. I don't really watch sports on Sunday afternoons. I like to tinker and try different business ideas. Both those things have made me as a leader at ShopFly so much more valuable. I understand pretty much every feature and functionality that ShopFly has because I try it 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?

35:31That seems silly. You're not going to change your life financially. It feels like a distraction. And I would say that's one of the greatest tools that I've ever, greatest things that I've ever done that has made me a better leader at Shopify. And it's just a hobby. There's something really, really powerful in that because when we, when I started this conversation, I asked you why people don't take the leap. And a lot of the reason why I think is because, and we talked about the psychology is when I think about starting a business, like a business or any business i'm stood at the bottom of mount everest looking up thinking jesus christ like i've got to find a website as you said i think i need loads of money who's going to work for me where do i get the tea from how do i send it in a post um what's the packaging i need to do branding and i need to do it all now and and also there's this other thing which in our minds we think of success as being me making millions or me making a ton of money what i almost heard as you were telling that tea story was like have this passion remove the expectation which sir david brailsford told me about really well just remove the expectation if you have ever being anything more than a hobby and just get going and you'll you'll stumble forward along the way and and that's okay i think if more entrepreneurs could see that mount everest there's just a bunch of pebbles and there's and remove the time frame where possible remove the expectation of huge success and just stumble forward through the process we'd have so many great great more businesses that we do now.

36:51And everyone listening to this has that. They have the hobby. They have the, they love tea or they love, I don't know, coffee or matcha or whatever it is. That perspective change of like, okay, well today I'm going to start my Shopify store. Tomorrow I'll think of the name. I won't, I won't even tell anybody just to remove even more expectation. And I'll just stumble forward through in my hobby and see where we get to in 10 years. Most people on Shopify don't register their business until weeks after they sign up for Shopify. So most people don't even assume they're going to need to register a business and that's okay.

37:20And it's not to say that every idea you have in the shower needs to be commercialized, needs to see the light of day. But if there's an idea you have in the shower and you're having it a couple of days in a row, try it out. Like, I mean, this isn't a pitch for Shopify, but like it's less than a couple Starbucks coffees to go start a business today. And if you fail, the cost of failure is as close to zero as it's ever been. You don't have to take a loan out. You don't have 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.

37:52But 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, it, there was very little expectation. I mean, no one thought it was going to be successful anyway.

38:26You sell one, everyone clap. Yeah. They're like, great. You're, you're, that's so cool. You have a business. No one asked me what my revenue is. No one's asking my EBITDA 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 Shopify right now is about 10 % of all e-commerce in the United States. In places like Australia, it's 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.

39:00It was Heather and Trina sitting at a coffee shop not too far from here with a friend of theirs that was a doctor who was wearing these hospital scrubs that just looked like shit. They're like, we can do this better. And that's how Figs was born. It was Ben Francis who said, why is there no clothes for just regular gym people? Either it's like gym rat stuff, like bodybuilders, or it's yoga. And that's how Gymshark came to the world. Or it's Tim and Joey at Allbirds saying, why is there no really great sustainable sneaker that feels good, that's washable, that costs this amount of money? That's how Allbirds got started.

39:31So no one had this massive 80-page business plan and then got started. That's not how businesses are created in modern times. They're created based on this nugget of an idea, and they're explored. and you get curious about it and you try this other stuff. And that's how you build companies that are long lasting, that change the fucking world. And that's how Shopify was started as well. Indeed. Indeed. It was an immigrant from Germany coming to Canada because he fell in love with a girl and got to this new country and couldn't get a job because he didn't have his working papers and was told he can start a business.

40:02And he looks around and he sees snow everywhere and he says, I'm going to start a snowboard company. And in 2004, there's two ways to sell a product on the internet. One way, you sell on a marketplace, which is very cheap, very inexpensive. Like eBay or something. Exactly. But you're renting customers from that marketplace. They're not your customers. The other way was to spend seven figures, no exaggeration, and have one of these big enterprise companies build you an online store. And he didn't have that kind of money. He didn't like those options, so he wrote a piece of software and started selling snowboards.

40:34And the snowboard shop was called Snow Devil. And very quickly, people started asking him if they can use the software to sell their own products. And he decided the snowboard store was a good idea, but the software behind it was a great idea. And that was how Shopify was born. And I met Toby around that time when he was transitioning from snowboards into software. And I became one of the first customers to use Shopify in 2006. And then you were the first non-technical employee as well. That's right. Yeah. And a couple of years later, after law school, I called him and said, I want to join you and a small handful of engineers, smartest people I've ever met in my life, still to this day.

41:08and said, let me be your Swiss army knife. Let me come in. I don't care what you call me. I'll be sales. I'll be finance. I'll be marketing. I'll form partnerships. I'll do anything and everything you need because I believe the world will be better if we actually get this thing off the ground. And we've been working at this for, you know, it's my 14th year now. When people hear those stories of these, you know, couple of women, couple of men, couple of people who had an idea, they saw a kind of gap in the market, they pivoted into it seamlessly and here we are today, you know it's worth tens of billions of dollars whatever that i want to zoom in on a particular thing which is at that time because i hear this all the time from entrepreneurs it's one of the again one of the barriers for them starting is well someone is already doing it there's a there's competition and i think about every business that i've been involved in that's been successful and at the time when i did it there was someone that was way further down the head than me and probably better capitalized capitalized more information that's right yeah smarter yeah all those things and it never has mattered.

42:06And 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 was a really big company. Yahoo stores existed. There were companies called Magento, which is still around today. Not as prevalent, but that was around. There are major competitors out there. But the idea wasn't necessarily to try to do something no one else was doing. It was try to do it better. And that, I think, is the difference between the great companies and just the good companies.

42:47That 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 arts and crafts, like an Etsy kind of style, or it was for big companies. IBM, SAP, Oracle had competitors there. Yahoo stores focused on very, very small businesses. But we never gave ourselves those constraints. It was let's allow people and enable them to build beautiful online stores quickly, effectively, that were customized for their particular brand, and try to bend the learning curve around entrepreneurship.

43:31And over time, like over many, you know, it's now almost 20 years. Over time, we're like, let's add payments. Let's add capital. Let's help with fulfillment. We should do point of sale because physical retail is important. What if we also help them with things like cross-selling across different markets? What if we create sort of a bank account to help them manage their cash flow? Over time, it sort of evolved from that. But the initial idea had lots of other competitors in the space. This was not this massive novel thing. We just did it better. And it's funny because a lot of those competitors, we absolutely do not remember now because you did it better.

44:04And 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 view, and just do it better? I mean, this is going to sound trite, but having deep empathy for how merchants and how your customer uses your product is very, very important.

44:36And 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 multibillion-dollar hegemonic incumbents. It's great. I love that we have Staples, and I love that we have Spanx, and I love that we have Black & Decker and Mattel using Shopify. But those are companies that were already successful before they started using Shopify. The stores that we are most proud of that we love to talk about are the homegrown success stories, because even though we are not responsible for their success, we simply made the journey a little bit less difficult over time.

45:24But 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 adding more value, a disproportionate value every single step of the way, we think we build a lot of loyalty with our merchants. And what then happens is the ones that do become successful never leave Shopify. So there are people that start a business that fails and they decide to either shut it down or they decide to pivot to a different business. We're okay with that. We're not changing physics. We know that most small businesses will not be multimillionaire companies over time.

45:55But the key for us is that the ones that do succeed never have to leave the platform. So it's almost like when you start on Shopify, it's super easy, super simple. In an hour or two, you can build a beautiful online store. But over time, as the complexity of your business increases, the solutions on Shopify sort of reveals itself over time. But it does so at the right time so you are not overwhelmed. And I think we are very hard on ourselves. And that's the right time. We're hard on ourselves that we really want to continue to push the envelope. Here's a very simple example. Everyone right now is talking about AI.

46:29Obviously, ChatGPT is really, really cool. We were using it already in a couple different ways. But the way we thought about it when it first came out was, this is all great, very cool technology. What is it going to do for merchants? What is the practical implications of AI on the lives of the merchants? And for us, it was like, well, wouldn't it be cool if AI helped merchants write product descriptions? So you put in your product photography or some meta tags, and ChatGBT helps you write a product description that will convert better. That is really practical. You know, obviously in Web3, for example, we always thought about this is all cool technology.

47:04The blockchain is amazing. What can we do with it? What if we can do token gated commerce so that you can reward your most loyal customers with new opportunities, new discounts, new events? We use this lens of practicality across every single feature we have. And we also think about, well, what happens if this particular merchant gets really, really big? I have a bit of a Moby Dick story. my Moby Dick in terms of Shopify, the one brand merchant that I've wanted on Shopify for so damn long is a company called Supreme. They're incredible. The Supreme story is amazing. But the reason I wanted Supreme on Shopify so badly, more than almost any other brand, is because I knew that they would test the limits of Shopify.

47:48Their flash sales are probably the largest flash sales across the entire internet, which means they're probably the largest flash sales across all of retail. and I knew that if we got them on, it would pull Shopify into a new category of resiliency, of performance. Most companies would have shied away from that. Most companies have been like, we don't want Supreme. We know they're a great brand, but they're gonna break this place. They're gonna break our product. They're gonna break our infrastructure. We invite that in. We want Supreme to be on because we know that if we can handle an iconic Supreme flash sale, we can handle anything else.

48:20And there's a little bit of like, there's this great book by Nassim Taleb called Anti-Fragile. Are you familiar with that? I love that book. And for those that haven't read the book, all you have to understand is that there are three systems. There's the fragile system. I take this glass, I drop it, it breaks. There's a robust system. I take this, I drop it, it stays as a glass. But there's a third system, like the immune system, where if you break it, it actually rebuilds itself better, stronger, faster. And Shopify is fundamentally an anti-fragile company. And I think your companies are the same way.

48:52You guys invite what call it pain, call it challenge, because ultimately you want to come out the other side better. And most companies, like literally 95 % of companies out there, maybe more, don't want that pain. They want to be copacetic and they want to continue the status quo. Really interesting. You know, I mean, my head went all over the place when you're just going through those stories, because I remember when this podcast started to grow, our provider actually told us to leave because we were bringing too much traffic. So that provider is never going to have incredibly successful podcast ever again, because they told you to leave.

49:27What if they would have invited you to stay and said, we're going to build more resiliency for you. They were like complaining about us. They were like, shame on them. Shame on them. Yeah. So we moved to a different, um, someone else that could host us because they said that we had too many downloads or something. You have too many. That is literally saying you were too successful. Am I right, Chuck? I want to make sure I'm correct because you dealt with them. yeah they basically said we were costing them too much money i mean 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 say come break our stuff it's going to make us better if you believe like and by the way anti-fragility is not just something for companies also for human beings i think all the stuff we talked about about my upbringing made me better made me stronger do i wish it those things wouldn't have happened potentially i mean in hindsight i wish i would have had i'd have less anxiety maybe but maybe i would be sitting here with with you steve today if those things wouldn't have happened is resilience the antidote for that and 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 you know ai comes out and you're saying to the team listen forward let's figure this thing out let's let's build some stuff and let's try it let's go forward you're gonna have to bring people along with you and those people are gonna go i just got comfortable with with what we're doing now, Harley.

50:46And now you're telling me to, so do you, how do you create that culture that fosters that sense of like resiliency and positive attitude towards change? Yeah. Two things. One is resiliency can be taught. You're not born resilient. You can actually learn resiliency. You can learn from your experiences. You can learn it from practice, but resiliency, I don't believe is something you either have or you don't. You can actually build resiliency. In fact, I think people, the most interesting people that I know that are resilient have had something happened to them that allowed them to build resilience on their own.

51:14Some 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, get the towel. I like the surfboard people. The surfboard people are my people. Those are the entrepreneurs. In terms of how we do it at Shopify, is Shopify is a company building software for entrepreneurs that is built by entrepreneurs. The amount of people at Shopify who had a business, have a business, are about to start a business, have side hustles. Anyone you've ever met that works at Shopify, because I know the people you've met at Shopify, Steve, they're also entrepreneurs.

51:49And actually, rather than doing their own ventures, we are collectively coming together to build something much bigger together, like one plus one equals 10. And I think one of the ways that you foster a culture of resiliency is look for the entrepreneurs. The reason I met Toby in 2005 was I moved to Ottawa to go to law school, had no friends, no family, never been to the city. I only went there because a mentor told me to go to law school and he was teaching law at the University of Ottawa. That's how I got there. And I asked one simple question, anyone I met, where do the entrepreneurs hang out?

52:21And I found this coffee shop with five other entrepreneurs who every Friday night got together and spent time learning from each other and sharing war stories and sharing tactics. And that became my tribe. One of those entrepreneurs was Toby. So I love entrepreneurial people. I love resilient people. And so you can search those people out. When you're building your company, you're trying to create a culture that is super effective, that looks for the alpha opportunities, that is very ambitious, that works hard. Invite entrepreneurs into your company. Create an environment that entrepreneurs want to be there.

52:56And 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, you know, Jack taking a photo of the bookshelf. I mean, I'm not just saying because he's filming us and he's got to make me look good here, but like that's the entrepreneurial way to do it. The non-entrepreneur way to do it is to be like, yeah, we need some books. You have the exact same books behind you here as you do in London.

53:30Most people won't notice that, but I notice the amount of attention and to detail you have and the care you've taken that every, that, that, that B is exactly where the B is on the shelf behind you. That matters. It doesn't matter to everybody, but it matters to the right types of people. And when you do that, you invite more of those people into your life. Do you, do you think as well though, that when you think about companies and leaders and how the culture is set and how that philosophy of like attention to detail is set, I've often thought that you might get like a group of people, like disciples of the culture, maybe the original founders or something.

54:03And they set that philosophy. They go, this is who we are. We care about the bookshelf being the same no matter where we are in the world. And then you have this other type of people who are susceptible to go either way depending on the culture they're in. And if the culture is strong, those people become the culture. If cultures, if they went somewhere else, they probably behave differently. And, but that comes down to the culture just being absolutely crystal clear and the hiring of that culture being, disciplined and the firing yeah i mean let me let me disagree with you on one point i don't think culture should be static i should think that every new person that joins your company or my company the culture should change slightly and hopefully it gets better over time but i think there's a lot of companies that they put a poster of an eagle up on the wall that's his leadership underneath and they call that culture or they say you know they're famously um patty mccormick created what's what's now famous known as the netflix culture guide yeah i remember and what what's 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.

55:02It was a public document. So you can read this. And if this does not resonate or this is offensive to you, don't even apply. I think that's actually a very good thing to do because it just, it's very honest about this is the type of place. I think one of the, one of the funniest lines in there was, um, uh, mediocre performance will lead to a superior severance. I love that. Right. It's super, super cool. So there's, there's, there's that aspect, which I think is, is really interesting, but I think the culture should continue to evolve and everyone that joins, it should get better and better. But I want to just say something like this is this narrative of the early days, I think is bullshit.

55:38Like this is a better version of Shopify right now than we've ever had. Our team is better. Our leaders are better. Yeah. There's some romanticism about the early days where, you know, like there's a photo that floats around every now and then of me sweeping the floors. I get it. There's, that was kind of romantic that we sleep the floors ourself. 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.

56:11I 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 that's a place where more people like us want to work and therefore other people like us want to work as well and that's why i love the idea of like building a company for entrepreneurs built by entrepreneurs that is really compelling when i when i when i speak about culture i think i'm kind of using the word interchangeably with the word um in that particular case maybe the word values but let's if we think about company culture in the context you're describing it I was um I was doing some writing over new years and I was looking at the life cycles of companies and they they often start like cults and I went through I think IBM Instagram all of these huge companies and I found quotes of the founders describing the early days like a cult and then they go into this kind of growth phase where because everything is breaking and they're trying to keep up with the market demand they're having to like rapidly install processes this is usually where founders like hire someone who's got like gray hair who's done it before and they sit them down with the little cult and they're like help in that growth phase and then they get to kind of like this enterprise phase where the processes are in place work-life balance has kind of been restored they have a lot of people so now they have like a hr department and things are different now going back to that first phase that cult phase it seemed pretty clear to me even like peter there was a quote from peter thiel where he was like you know um words to the effect of the start should resemble a cult.

57:44Do you believe that? It's something I've pondered because the word cult is such a toxic word. So be careful here, Ali. I mean, I, I, I, yeah, I don't, I don't know. I'm not sure if cult's the word I would, I would use. What I do think is that you need to have like, and this is not just in early days. It's at every stage of a great company. You have to have a strong mission. And part of the reason that I think Shopify, for me at least, is the place where I can do my best work is because the mission is not interesting or cool or it really hits home for me. I'm not, it's not to say that I wouldn't be a good, a good president of, of, of Pepsi.

58:20I'm sure Pepsi's mission, I don't know what it is, but I assume it's something like do something with the world and make people happy or something like that. Ultimately they're selling products. They're selling sugar water and they're selling candy and they're selling chips and whatever they, whatever Pepsi sells. I don't think I can do my life's work at Pepsi. I don't. Because ultimately, at the end of the day, the mission of the company, even if you add all types of, you know, rose petal glasses and you say, well, we're not it's we're not selling cola. We are, you know, we are nourishing the youth of the world to pursue their path.

58:53You're selling something that like I like, but I don't really love. and I think if you're if you have the ability to find a company whose mission you believe in in every at any stage really hits you hard that's probably the company you should go work at and you probably say that for a very long time and even the fact that not every not every person needs to stay at every company forever not everyone's gonna be a lifer that's okay people want to jump on the bus and or the rocket ship at different times that's fine but I think you do your best work when the mission of the company deeply reflects your own life's mission.

59:28If I wasn't at Shopify, if Shopify didn't exist, I probably would be doing something around encouraging more entrepreneurship, inspiring more entrepreneurs, creating tools that help entrepreneurs start, scale, and build faster. I just found this vehicle that does it way more efficiently than I ever could do on my own. It's called Shopify. So you're damn right I'm going to want to be on that bus or that rocket ship. But I don't think it has anything to do with what's on the wall. I think it has to do with the fact like, what is the company actually doing? If you strip away all the marketing speak and all the brands speak, what is the point of the company?

1:00:01What's the objective? And I think that really matters. For those entrepreneurs then that Shopify supports, when we talked about this Mount Everest analogy where you're thinking about starting a business, you're looking up, it feels super intimidating. We talked about how you can break that down into simpler steps focusing on turning your hobby into a into a small business you gave the example that many of shopify's merchants don't even register the company by the time they start the store the other part that's um intimidating when i'm thinking about starting a business if i'm a startup entrepreneur it's just information and you used the word earlier on use the word mentorship now okay i've got a philosophy to how i'm going to start it i'm going to focus on a hobby, Harley.

1:00:42I don't need a ton of capital as you've outlined. But then there's this information piece, which is maybe the most important piece because information, for example, is even the knowledge that out of Shopify exists. It's also like, how do I find where I'm going to get this tea from? How would you recommend an entrepreneur solve the information problem? And if you could give me some kind of reference to your framework on mentorship, that'd be super helpful. Yeah. I mean, the mentorship framework that I use, it's actually really simple. It's that I don't think any one particular mentor is going to be, you should wholesale take everything they say.

1:01:15Lindsay and I got married in 2013. And I thought about who are all the people that I perceived to have a really great relationship with our spouses. And I went through the list. And I kind of laughed. I was like, okay, am I really going to ask that person to be my mentor? I don't really respect that person in any other avenue of their life. So why would that person be my mentor? So I went through this list and I realized, you know what, like I'm doing this all wrong. If I want to be a really good husband, a really good father, a really good leader of Shopify, I want to be a really good 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.

1:01:58So in the vertical of parenting, who's someone that I think does a really good job on parenting? Three or four people, I'll give them a call. The neat part about doing it that way as opposed to saying, and by the way, the person that, like, I can't believe I'm sharing this, but this is kind of funny. I told you about a mentor of mine that convinced me to go to law school. I love that guy. He's a huge part of my life. he's on his third marriage yeah he's not going to be my marriage mentor he'll be 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 lindsey who i just felt had the most special relationship with his wife and i began meeting him and asking questions about how do you cultivate that the same thing with parenting but all of these mentors in each of these verticals they're not the same people now the reason that's that's that's important is because like that, like a video game or like any skill set, you can't be good at everything.

1:02:54And so I'm able to derive different things from each of these mentors and then create my own version of it. But the second reason it's a really cool way to do it is that person who is a really great husband, but maybe not a great entrepreneur. A lot of people, like no one else is calling him to ask for his advice on parenting because most people are like, well, he's not someone that I'd want to emulate because in business, he's not that successful or, or in other aspects of life, he's not someone who I'd want to, who I admire. And so the way that I've always thought of mentoring is find these different people for different aspects of your life.

1:03:24And then as, as, as your, as you evolve, you may have to replace them and bring them in and bring them out. Some people may be around for a long time. Other people after two years, I mean, I had a really good mentor around parenting who was really only valuable for newborns. And it turned out that a couple of years, you know, as the kids grew, it wasn't doing a very good job. He wasn't teaching his kids all the cool stuff that I want to teach my kids, like skiing, for example. So that's part of my philosophy on mentorship more generally. I think there's sort of two sides. So you have mentorship on this side, which is like people you want to emulate.

1:03:55But there's also 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. We probably both need to figure out like how to set up a bank account and how to get our first sale.

1:04:28And we probably have to figure out like simple bookkeeping, for example. So finding people that actually are at a similar stage, even if they're not at the same vertical as you are, is super valuable. And those people exist. They're everywhere. But finding them used to be really difficult. Actually, now it's much easier. Go to Reddit. Look on YouTube. You can literally go, if there's a video about bookkeeping for DJ companies, there's probably a video on YouTube somewhere. Go look at the comments. Who's engaging the comments there? Who's replying to those comments? Or on Reddit, who's sort of a power user in a particular subreddit?

1:04:57You can find those people either online or in person, and you can build yourself and inform a board of directors when you're getting started. Now, if one of you eclipses the other in terms of growth, you're probably not going to find as much value from that particular tribe as you previously did. You're going to want a different tribe. But if you do this over time, you actually end up with far more, the acquisition of information gets much easier over time. And I don't think enough people take advantage of that. If I gave you$3 million and I said, Harley, you've got to invest$1 million in three companies, more specifically, three founders that are currently Shopify customers, who would you invest it in?

1:05:40And why would you choose those entrepreneurs and founders? It's like asking me like, you know. Choose your babies. Yeah. Choose your favorite child. Yeah. Really, I'm trying to get at the characteristics of the founders that you back. You know, I know right now it's almost, if you sort of word clouded social media right now, the term content creator would come up probably more than any other term. And I think actually it is completely misguided of what people think content creators are or do. I think a lot of people assume that what's happening right now in sort of the content creation space is you have someone that has a super successful podcast, for example, or a super successful blog, or a super successful, you know, YouTube channel.

1:06:18and they want to expand their monetization. So they do something like they make t-shirts with the diary of CEO on it. The greatest content creators now that I see really building their brands are doing something totally different. And I know this is an obvious example, but what Kylie Jenner did with Kylie Cosmetics is nothing short of brilliant. Now, it's not to say that 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.

1:07:01She was in makeup tutorials, and she was doing makeup classes, and she was giving tips and tricks about makeup. And then eventually she's like, you know what? I want to create a better version of makeup for myself. And so she went into the lab. I know where the lab is. It's not too far from here. I know the store really well. And she went and she created what she believed was a better version of makeup called Kylie Cosmetics. And then she brought it to the world. What Jimmy did with like Beast Burgers or with Feastables. Mr. Beast. Mr. Beast, yeah. Mr. Beast did with Beast Burger or Feastables.

1:07:33He didn't just go to a chocolate company and say, I want to create a Mr. Beast chocolate bar. He went, he loves chocolate. He loves chocolate. He also loves burgers. And he said, let's create a better burger than I can get right now on Uber Eats. And he went and he cultivated it. He said, this is fucking delicious. And now he's going to actually distribute it. He's going to actually scale it. I would definitely put one of those millions of dollars into the hands of a creator who's on the precipice of figuring out what exactly does my audience like and then creating a better version of that. Because I think that most of the content creators out there do create promotional products where they put their sticker on something that already exists.

1:08:11But the good ones, the great ones, they actually improve on what already exists in the world. And then they have a built-in distribution channel because they already have an audience. So that would be the first one. The second one, I think, would be someone who does something very niche-y. You and I are both in black t-shirts. In my opinion, there is someone who thinks about black t-shirts more than anybody else on the planet. His name is James, James Purse. James Purse is obsessed with black t-shirts. And so I love wearing black t-shirts. So this is maybe a selfish one, but I'd put a million dollars out of the three million that you're giving me metaphorically into James.

1:08:46And I would say, go do more of this. Because I actually, now I'm not sure he needs my money. Certainly Mr. Beast doesn't need my money either. But I love the idea of someone going super deep on one particular thing and building the best version of it on the planet. I don't think most people do it. I think most people start with something like a t-shirt and they go very, very broad. And James hasn't. I mean, he makes other clothing, but he has a ping pong table, not joking, that he makes, which is the most beautiful ping pong table I've ever seen. He has a couple of these sort of villa rentals in Mexico, which he designed himself.

1:09:22But it's one particular vertical that I think is really, really cool. Maybe the third thing that I would invest in, so content creator would be first. Someone like James Purst, who does one vertical really well, would be the second. The third one would be someone who is trying to bring something that was unattainable for the masses into their hands. So this microphone that we're using right now is a Shure SM7B. And from everything I've read, because I like this type of stuff, it is like one of the greatest pieces of engineering, audio engineering ever created, which is why Shure, who makes the microphone, hasn't really changed it much.

1:09:57This is a great microphone. It's expensive. someone who is taking a microphone like this this type of quality and creating a less expensive version of this so more people can try their hand at podcasting that would be really cool too interesting making like quality more accessible to the masses right that's right and and i don't just mean like there are other good microphones out there but you know the difference between a dslr camera that we're using now versus a webcam of course and in terms of the characteristics of the human, what do you bet on? I mean, we talked about this a lot, so it's going to sound repetitive, but it's resiliency.

1:10:37I'm looking for those surfboard people, the people that see that wave and grab the surfboard. I want people that are optimistic, but I think generally the people that grab the surfboard are optimistic. I want people that are hardworking, but I find generally the people that grab the surfboard are also hardworking. I want people that are high character. I think those are often the same people. But I want someone who, if you were to give them a million dollars or$10 million or$100 million, they would still do the exact same thing the day later because that is their mission. That is their life's work.

1:11:06And I think if you find that, you should cherish that. Anyone who's watching that has found that thing that no matter what they had or don't have would do this particular thing, those are the types of people that I would back. I don't really care where they're based. I don't really care what their experience is. um i care about are they the surfboard people because i think surfboard people are deeply curious and deeply ambitious we spoke to your team and asked them what you in particular were good at um oh god they um they did not tell me you did that did they not they did not we said we said could you tell us everything harley's good at and there was like a big sort of 30 second pause and then they just hung on the phone and so we can so we'll move on um we i heard the gasp backstage stage here yeah someone in you probably couldn't hear that on the mics by the way everyone everyone that like works closely on my team uh are all also all entrepreneurs themselves they all have side hustles oh really cool yeah no they said lots of many many amazing things about you um many many amazing things the one that i wanted to focus in on because i couldn't 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 what what on earth does that mean I calendar everything.

1:12:17Well, they made it sound much better. Maybe they should be the storytellers. I truly like before I came here, I want to grab a quick coffee. That was in the calendar. My meditation this morning is in the calendar. The things that I really, really care about, I diarize and I stick to that diarization. And because of that, I think it's easier for me to prioritize what's important in my life, both professionally and personally, than most people who they try to fit things in. Um, 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. Me.

1:12:49Okay. I'm not, I'm, I'm usually not in a rush. I'm, I'm, 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 diarize or, you know, scheduling, I don't know, like lunch. I, I, this is going to sound maybe lame to some people. It's worked well for me. In my calendar, you will see walk with Lindsay, like walk with my wife. You will see like ski time with Bailey or Zoe.

1:13:22Everything is in the calendar. Every person, someone that I want to hang out with that I want to actually, a mentor of mine that I don't think I'm spending enough time with. They go in the calendar every four weeks and I commit to that. That helps me. I'm not sure I'm like the world's greatest prioritizer, but because of that, I'm able to prioritize things in a way that I think most people may not always be able to do. So that's one thing. In terms of the other prioritization, there's very few things that are like nice to haves in my life. I don't do the nice to have thing. These are things that are in my life are must haves.

1:13:54And 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 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 um you know do research on some other topic like this is kind of the stuff that matters and so when when I when we you and I first connected I knew that I would one day would love to be on your show why because like when I think about do you know the concept of ikigai yeah yeah so when I think about the ikigai concept which is really life's work by the way which is a Japanese a Japanese version of it which is far more elegant than the term life's work.

1:14:42But what am I good at? What is the world going to find value in? What can I get paid for? And what adds the most amount of value, I think, generally? I forgot the exact terms. This conversation with you hits a bunch of those, like the intersections of Venn diagram, this hits. You're a great entrepreneur. Your audience are great entrepreneurs. I knew the conversation would be interesting because I listened to this podcast and I love your show. It was obvious to say yes. if someone else asked me to do a conversation for a couple of hours like we are today, I have to put it through the filter of like, where does this hit on the icky guy spectrum or on the life's work spectrum?

1:15:20I think that's why they say that. During your time at Shopify, what has been your most difficult personal challenge? Like what was the day or the period where you had your hardest time? I think it was on a personal level, it was probably the pandemic. I felt very, very lonely. I was low in energy. I was high in anxiety. And I wasn't making time. It was like the pandemic was crazy for Shopify. Overnight, every physical retailer shut down. And we were really lucky in that a lot of them ended up coming online with Shopify. That was really cool. But we ended up hiring a ton of people very, very quickly.

1:16:01We were always by ourselves. We were fully, you know, fully remote at that point. And I, I was not in a good place. What do you mean you weren't in a good place? I wasn't present at all for my, I don't think I was present for my team and I don't think I was present at home. I felt like I was simply just trying to tread water and I wasn't making time. I had this sort of great, I talked about my calendar efficiency. I had this great sort of plan usually. And then the pandemic hit and like everything changed and scheduling all this time. Like I didn't replace the time with mentors that I meet in person with, with virtual coffees.

1:16:36I just canceled it. And so I just, it was a very, um, reactive period for me where I don't think I was mindful of what I needed to be a good leader. And we were just hiring a ton of people and I was lonely. I was really fucking lonely. That was a low point on the professional side. On a personal side, it actually happened a couple years prior to that. And it was really around the transition from being sort of COO to being president. I felt like I was letting down the company. I was letting down Toby. I was letting down myself if I didn't have a particular role at the company. And that role came with a huge headcount.

1:17:12Like all these different teams reported up to me from a headcount perspective. There were like 6 ,000 people that reported to me. It was kind of a crazy thing. But I knew it wasn't the right job for me, but I did not have the self-confidence, nor did I have enough introspection to say, I'm in the wrong job. And I was fortunate that other people, especially Toby, kind of pulled me into this new thing and said, hey, there's a role here that is different than what you're doing. And if you can just get over the fact that you're not going to have 6 ,000 direct reports, but rather you're going to have a couple hundred direct reports or maybe less than that even, but you're going to do more of the stuff you want, which also happens to be more valuable for Shopify, that we're going to have a new phase.

1:17:54We 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. I was just grabbing as much as I can, trying like Swiss Army knife stuff. But I never kind of settled in to say, where do I actually want to do? Like, Like, what is my craft here? I always loved storytelling, but I was never, I think I was too caught up with ego and insecurity to admit this is the shit I want to do. I don't want this the rest of my life.

1:18:30I don't want to get so good at this. And it was really with help with coaching and the people around me that I was like, hey, what if I actually just did this thing? What if I took this other role called the president of Shopify and I just focus 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, and I think I'm a much more valuable member of our team because I've, I've sharpened my point rather than become a well-rounded Riverstone. In those dark moments and those hard times, did you, did you speak to anybody? As in what I'm saying?

1:19:02I mean, speak to the people that were next to you. Did you speak to Toby? Did you tell your wife how you were feeling? My wife knew I wasn't happy. Did you have a conversation? No, I don't think I was able, I don't think at that particular moment I was able to actually even see it. I was like, look, I've been here for a long time. Maybe this is it. Maybe I've, I've hit, I've hit the, my max here, right? I mean, been here for a third of my life. Maybe this is it. Maybe like I should just quit while I'm ahead. And what I didn't fully appreciate is that the thing that I really want to do is also the thing that everyone else really wants me to do.

1:19:37It's also really the thing that is most valuable to the company at this particular. For your self-esteem, that enoughness. I was like, but that's not enough. Yeah. I'm not doing enough. I'm not contributing enough. And what does that mean about me and myself? That's right. Obviously, I'm not enough. I am the happiest. I'm not just saying that because we're on camera. At this particular moment, I'm the happiest and most fulfilled. And I find the most meaning in my work that I have in a very, very long time. And it's because I'm doing the thing I should be doing. which is this particular skill, this particular role that I have is kind of built perfectly for me.

1:20:14And I need to be okay with the fact that I don't have the largest headcount and most of the company doesn't report to me. And I don't really care about that. What I care about is, am I adding the most amount of value? And do I feel like I'm growing? Do I feel like I'm actually contributing both to the company, but also to my own 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. Again, you can't just do what you want. Like, you know, if I just want to be the chef at Shopify, I'm not really going to add much value.

1:20:52But if it turns out that the Venn diagram overlap of what am I really good at, what does a company value for me, and what is something that is uniquely in my skill set, if wherever the venn diagram overlaps if you can do that you win what about in the pandemic when you're struggling did you did you have a actual conversation this i'm asking this question because i'm so compelled by like when specifically with some men who are often a little bit more hesitant to talk i'm compelled by this idea of like when we speak when we reach out to a friend a wife a partner to say listen i'm struggling here and do we do it after do we do it during when did you do that.

1:21:32I did it way too late. I waited way too long for that. And I wish I had, and I think it would have saved a lot of grief. Um, it would have, I would have been, I don't think the pandemic was especially great for anyone. All of us sort of dealt with it in our own, in our own way. But I think that I, I made it way more difficult on myself because I, I was lonely and unhappy and maybe had some sort of, you know, maybe there was, I talked about anxiety, but maybe there's a bit depression there as well. However, I didn't talk to anyone about it because I didn't feel like I had the right to complain.

1:22:04I 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 are people that were dying. They 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 it 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 happened by, by, by telling people that by saying it out loud, you know, there's that, that whole theory about don't tell people your goals.

1:22:36I call bullshit. I think it's ridiculous. Don't tell people your goals. I think you tell everybody your goals because the cool part is if you have people around you that are good people, they're going to hold you accountable and you may actually hit your goals way faster, more effectively. And it's fun to share in a celebration and celebrate someone, you know, who deeply wanted to do something who actually ends up doing that thing. so it's funny because if you feel like you can't share with people people your goals it's really what you should do is get new friends totally i mean like why wouldn't you want to tell your friends and the people around you you have ambitions well the common critique of telling people your goals is that when you tell someone your goal you as an individual you get something from that and and and and so the 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.

1:23:24In 12 months from now, I'm gonna run a marathon or ultra marathon. In 10 months from now, I'm gonna have$2 million of sales in my online store. In 10 months from now, I'm gonna do something really challenging and difficult. Especially 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. I hesitated and it's because of some weird bravado that like I'm strong, I'm capable and I'm fortunate and therefore I don't deserve to be unhappy you're depressed or anxious. And I actually think my biggest lesson from all of that is vulnerability for the right people.

1:24:02To your point, good friends, good family, good colleagues, good partners. It shows strength. It does not show weakness. And I was very weak and I didn't want to show vulnerability. I wrote in my diary the other day that vulnerability is a magnet, not a repellent. And I think in our masculinity, in our toxic masculinity, sometimes in our sense of wanting to be what we think strong is, the sort of misrepresentation of strength, we see being vulnerable as a repellent, as in, I will lose things. People will leave me. They'll think I'm weird or weak or whatever. And then every time I've ran the experiment of vulnerability, and when I say experiment, I mean, because it feels risky sometimes.

1:24:38It'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 were in that basement during the pandemic. your family were there in the house and we often confuse this idea of being alone with loneliness totally and simon 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 and the brain goes do you have any friends he goes i have loads of friends i've loads of people around me have a big team but i'm lonely there's an important distinction to make um which i'm sure you can speak to in europe because i was thinking well you had your family had your wife but i was like no steve you're falling into the trap again.

1:25:15He wasn't alone. So I was not alone, but I was lonely. And actually this is where going back to your, your point earlier, which is a great point about entrepreneurship being a lonely activity or a lonely sport by having more people around you on the journey with you, even if they're on their own journeys, but they're sort of tangential to your journey, it's a little bit less lonely. Yeah. And if you do that across a couple of different areas of your life, like if you work out at a gym or you go for runs in the morning, finding someone else to run with you is one thing but finding someone else to run with you who's sort of going through the same like i want to run five kilometers and it's tough for me right now you do it with somebody else who also wants to run five kilometers and stuff for them too there's an immediate connection there so in one case you may be not like you're not alone because you have someone running with you but you're lonely in other case if you're on a similar journey together you have a shared experience or you're sharing an experience that takes away from the loneliness how does that square with shopify's approach to remote working because i've this is a debate i've pondered over and over and over again in my head which is like there's no correct answer here we all know that everyone's got a different mission every company's got a different mission but one of my reasons against um this total remote work scenario is because i think there's been a decay in institute 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 although that's a dangerous thing also right of course and it's also age and demographic specific and there's a little bit of privilege in there as well because you know everyone's situation is different this is something i'm evolving on but when i'm like an 18 19 year old just left university when i'm 21 years old and i've just left university i want to be do i not want to be around people um 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 um as i used to once upon a time how do you square all of that together so the reason that we're not fully remote is because of that exact reason.

1:27:25We had about, I don't know, 10 or 11, something like that, offices around the world. And we were full-time in the office pre-pandemic. And now we sort of have this model which we refer to as digital by design, which means that office centricity is over. And the reason that's important for us is that we've been building this company out of Canada, you know, for almost two decades now. And so in every single job offer we gave, there was an asterisk that said, It's part of this offer. There's a condition you have to move to Canada. And so that immediately limited the type of talent of people that come to Shopify.

1:27:59And so there's a real advantage to the fact that now you can work anywhere you want. So that's really valuable for us. First time that our new CFO is based in New York, our new GC is based in DC, our chief operating officer is down south. That is great. People can live wherever they want. However, we didn't close the offices. We converted them from quote-unquote offices to more of these we call bursting locations where you can come in for a burst, which is just an onsite. And we actually not only like the idea of people coming in, we force people to spend time with their teams in person at least once a quarter.

1:28:35And 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's 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 for sure office centricity has a downside a clear one what's the downside in your view of that work from wherever you want but once a quarter uh it's that not it depends on if your manager really likes the idea of being in person you're probably gonna be in person more often and if your manager does not you may be less um so we're trying to work around that and create some guardrails there but i don't think there's any perfect solution um a lot of companies are going the opposite way now you're hearing like snapchat and twitter on twitter yeah they're all going they seem to be going back to like 80 in the office etc the good news or the bad news i don't think anyone's got this right yeah and the companies that will get it right longer term are gonna be the ones that are most introspective about this.

1:29:44What's working, what's not. Be honest about it. So we know that being fully remote doesn't work for us. We need to be in person sometimes. We also realize that it's really an amazing opportunity for someone to come to Shopify who can have an incredible role building great product or doing something at the company that's very valuable and live anywhere they want. That is an amazing opportunity. In the early days of Shopify, I moved to Ottawa, Canada for Shopify. And that's 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 knocked it out of the park just yet.

1:30:15What I would also say is that just back to the Simon Sinek quote or philosophy. I think we all need like we may not go to church as much anymore or youth groups or, you know, organized sports. I think we all need our own version of that tribe. And I think developing your own community and your own tribe, even if you guys sit around and stare at screens and you're playing video games together, I think having these rituals, I'm not religious, I'm Jewish, but I'm not religious. But every Friday night we have a Sabbath dinner, Shabbat dinner. And we say sort of the very basic Jewish prayers. But this ritual that my kids look forward to where they, you know, they say Shabbat Shalom and my wife, you know, makes this amazing like home cooked dinner.

1:31:01I mean no matter what happens I'm home Friday nights even if I have to travel I'll go home then I'll leave Saturday morning because that is a ritual that I think is important and I think we all need rituals in our lives and I think the cool part of rituals is like you can create new ones all the time the key though is consistency and and the direction of travel at a very macro level with all these things that are happening in technology seems to be um one in which where we're being stripped of community and in-person connection which seems to humans aren't changing technology is but our innate fundamental maslovian or like psychological needs aren't changing but the society we live in i think is optimizing against our um against natural connection living in you know four white walls in the middle of a big city alone swiping on tinder ordering your food using a piece of glass screen all of these things seem to be robbing us of that connection And I reflect on this a lot.

1:31:53I go, the reason why the Diary Overseer is successful and the reason why a lot of the things we've done have really worked well in terms of like the content and the media is because we, without really being that intentional about it, to be honest, have created a sense of connection for people. They will hear your story about your own insecurities or about the things you struggled with. And that'll make them feel heard and understood and connected in some way. I love that. I actually think that that is one of the most, this sort of shared experience, even if I don't know you, is really impactful.

1:32:22We 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 got 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.

1:32:54No one has that. 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 the like when they're lonely they say i'm lonely here are the changes i have to make but no one has it all figured out and i think that in itself is what i figured out when i had 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 it was freeing for me it's so true that nobody's there it's like a party that you're striving towards that actually nobody's out you know everyone i mean you know more people than i like the people that sit in this chair that you know are way more successful than i am i've listened to a lot of your interviews, we're all kind of working on our own shit.

1:33:47Yeah, 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, I didn't want to say that. They're called the Diary of a CEO conversation cards. And what we've done is we've taken all of the questions that all of our guests have left in the famous Diary of a CEO. all of the amazing guests we've had on the show we always ask them to write a question that helps people to to go a little bit deeper and we've made them into these cards on the front of the card you'll see the question and the person who wrote the question on the back you have a qr code scan that you can see that the next guest that had to answer it so we're really letting the cat out the bag here cool i picked three cards for you the idea is that people will buy these and then play them at home with their friends and connect because vulnerability is the door to connection you just have to pick one sure

1:34:43Gary Neville tell me something you've never told anyone before I don't think I'm a great father I want to be a great father but I don't feel I'm a great father I feel like I only have I have like 10 units of energy and if I give units of 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 um and i really want to be a great father so that's kind of it's quite vulnerable but that that's the truth um yeah is that because of your definition of what a great father looks like is maybe not fitting the great father that you are um potentially uh do you see what i mean by that Yeah, I do.

1:35:39Because you're an inspiration. So, I mean, this goes back to am I enough of a father? Am I enough, right? But the thing about being a great father is there is a limited time component to it. I don't know how much, like Bailey is six. In 12 years, she's going to be off out of the house somewhere, I suspect. I get 12 years to become a great father. And I don't know exactly the right path to get there. I know what my weaknesses are, but they're a little bit elusive. Am I present with them? Am I mindful to their needs? But that's something that I struggle with. And I'd like to be, if I sort of think about three or four elements in 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, can I be a really great dad?

1:36:34And I don't also know how to gauge that. a lot of the other metrics I can gauge. Lindsay was very clear to say, like, you're a great husband or like you weren't a great husband this week. My work can be reflected by my performance. I don't know the stock price is exactly directly. You know, I don't think there, I think that's more correlation versus causation. But the other points in my life, my contributions to the community, I can measure those things. 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 um i've never met someone that says i am a great father yeah you may be right um now maybe actually the pursuit of that is in itself what i'm trying to do as is the case with the life right right exactly exactly right um but by the way even like okay go back to vulnerability Millions of people are going to watch this And maybe there is someone who's watching That actually is like hey I actually think I am a great father And here are the couple things that I use to gauge that One of my Friend of mine who He's not really my parent role model But maybe he becomes that at some point I asked him what a great father or 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.

1:38:08Another one says like, there's a famous quote, which is you're only as happy as your least happy child. Have you heard that, right? I've actually heard the corporate version of that, which is like your only successful is your least successful division of your company, which is also a really interesting way to kind of put that. But that would sort of be the one that I don't think I've admitted that because I haven't really had a venue to actually say something like that before. we have a closing tradition on this podcast where the last guest asks a question for the next guest we'll see that's what becomes these conversation cards um the question that's been left for you interesting one because it's a bit left field but what's a common misconception people have about you and more importantly how does it make you feel

1:38:52because i talk so much about entrepreneurship there is i've heard this now from a number of people that I don't ever talk about the failures that I've had from a business perspective. And partially, I don't do that because I don't think they're necessarily that valuable relative to some of the successes. We talk about DJing and t-shirts and Shopify. There are literally 20 other companies that I've started that have been total fucking failures. And I think the common misconception is that the stuff that I've worked on have all been not huge success, but generally successful because I talk about them so much.

1:39:31And I, I, it makes me feel sometimes like I'm not more recently that I'm not being as helpful or honest as I, as I, as I should be, because I just don't have, I don't have the space or the venue to talk about the slipper company, the poker chip company, the nurse uniform company. Like those are all real companies that I started when I was in college or undergrad or when I was a teenager that failed miserably. And the misconception is that I think that everything that I've worked on has turned out to be good or successful. When you look at yourself in the mirror, and I'm just saying that as a metaphor, and then you look at the perception of you, does that create a certain dissonance or a feeling of like, I don't know, people call it imposter syndrome, which is a term I don't love.

1:40:17But 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 i have i have that as well so here's another here's another way to put sort of the the failure thing um i do a lot of tv and and um and i'll get feedback that you know that was really great i saw you on the show or i saw you do this interview or saw you on on on squawk box um and i'm like great yeah thanks no i appreciate the confidence stuff. Sometimes I want to tell them and I don't often tell them, do you know that I put in five hours of work memorizing those data points?

1:40:58I 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 a good storyteller, like I put a lot of time into preparing for my conversation with you today. A lot of time. I've watched all your interviews. I literally, as I told you, like I, I didn't finish my run until I listened to the entire Seth Rogen interview. Um, 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 around vulnerability of actually sharing.

1:41:32This 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. And so when I look in the mirror and I think to myself, where is the dissonance? It's that sometimes, less recently, but certainly oftentimes, previously in the past years, I've made it seem like this is easy for me. And it's not easy for me. And I was never the smartest kid in any of my classes. I never got, I probably made it seem like I was smarter than I was in the classes.

1:42:10When I wanted to do well in a class, I just outworked everybody else. And I think if anyone out there wants to emulate anything that I've done, emulate my work ethic and the journey, not the destination, because it's been fucking hard and still fucking hard. And I embrace it and I enjoy it. And I wouldn't trade for anything else in the world, but I've had tons of failures and I work really hard to make sure that I have fewer of those over time, but it doesn't come easy to me. Harley, thank you so much. Incredibly enjoyable conversation and I've learned so much, but I've, it's funny though, I've done this, I've done so many of these podcasts and I still continue to learn from every single individual and so many incredibly unique and, and for me, really defining ways.

1:42:57I wanted to close with just one thing because I think I'm thinking forward at the guests we've got coming up and the guests we've had previously, and maybe you're the guest's best place to answer this this started as a very business-centric show business-centric podcast started as a me as a young entrepreneur building a company etc etc there's a huge part of my audience base that are doing exactly that right now like they're like maybe they've started their shopify store um maybe it's day one they know what they want to sell maybe they don't maybe they're not quite there yet but if there were a piece of advice you could lend to someone who wants to go on that journey of entrepreneurship of all the things we've discussed today what would that closing remark be?

1:43:39Remember that the cost of failure right now is the lowest it's ever been in the history of the world. And if you can remember that, it means that there's absolutely no reason why you shouldn't keep trying. And if it doesn't actually work, try something else. I think this idea of cost of failure is a fascinating one because it's never going to be zero, right? Because ultimately, 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 to zero as it's ever been means that if you have any instinct to start a business in the shower, when you're driving, when you're on a walk, randomly you have this like, this would be a cool idea.

1:44:29Try it. when you look across the millions of stores on Shopify, who've now sold more than half a trillion dollars on Shopify, the vast majority of them did not wake up and say, I'm going to be a great entrepreneur. They tried something, it worked, they scaled it. They tried something, it didn't work, they tried something else. That was when they scale. When you look across the stores on Shopify that have been successful, all of them didn't start out with this vision of building a billion-dollar company at some point. And I think that the fact that we can start a business now for the price of a couple cups of coffee, and that business can grow to be a large, multinational, multibillion-dollar company if that's what you want, that did not happen.

1:45:11And it certainly did not happen in the time span that's happening right now. The companies now, there are companies on ShopLite today where they're doing a billion dollars or more in sales that didn't exist six years ago. Six years ago, it was a shower idea. and now they're a multi-billion dollar company. Or if you don't care about building a billion dollar company, they've changed their entire vertical, their entire, their world, whatever the world they're in, they've changed it entirely and it'll never be the same again. And so - What a time to be alive. What a time to be alive. What a time to be someone who actually has an idea and wants to share that idea with the world.

1:45:49And if you're not sure about an idea, what you could sell, how you could start, think about something you already do. There is a store on Shopify that sells the most delicious matzo ball soup. What's matzo ball? Matzo ball soup is a Jewish chicken soup. Okay. It's this matzo ball. It's like if you go to a Jewish deli, you should actually try this. You should go. There's a store on Shopify that says matzo ball soups. And when you look at the story of how it got there, they were just making matzo ball soup for their friends and family. And at some point they realized, maybe I can share this with the world.

1:46:17And they do. And now they have a real business doing the thing they already were doing, except now someone is paying them for that. That is incredible. And that's the time we're living in right now. What a time to be alive. Harley, thank you so much for your time and your generosity. It means the world to me. And it's been an incredibly important conversation. Great conversation. Thank you for inviting me.

1:46:54you