Entrepreneurship Is A Mindset: Shopify President Harley Finkelstein On Why Failure Is The Path To Success

24:08And I DJed about 500 parties between the ages of like 13 and 19 years old. Mostly barbara mitzvahs, weddings, that type of thing, private events. By the time I was in college, I realized that whatever I did, entrepreneurship was going to be a big part of my life. By the end, I didn't actually care so much about the DJing craft, the music, the mixing, the lighting. I just liked the idea that I was able to create something for myself. And I was able to make money from it. I was able to employ friends through it. It was just this really cool tool in a tool belt. But where things really got serious for me from an entrepreneurship perspective was we moved to South Florida when I was a kid.

24:51And I went to, so after high school, I moved back to Canada to go to McGill University to go to college. And my dad got into some trouble. And my dad ended up getting arrested, white collar crimes, and I was basically given this ultimatum, which was either I moved back down to South Florida with my mom and two much younger sisters, or I stay in Montreal. And I decided that I would try to use this tool, take it out of my tool belt again, called entrepreneurship, to solve this new problem. The DJ problem was one of passion. I wanted to do this craft, and no one would allow me to do it, so I used entrepreneurship to solve that problem.

25:28This next problem was I had to make real money. I have two much younger sisters. My mom needed help. financially. My dad wasn't around. I ended up selling t-shirts to universities across Canada. It was a real business. I made real money. I was able to help my sisters go to private school. I was able to help my mom with rent. And so entrepreneurship started as this interesting thing that was very much focused on craft and excitement and passion. And it migrated into this tool that would help me solve a problem. In this case, it was - A survival practice, right? Like you learned what you learned when you were younger.

26:09And when in your moment of need, you realized you could figure your way forward through this experience that you had had previously. That's exactly right. And not just that, but it was, it's not a perfect meritocracy, but it was the closest thing I could find to a meritocracy, which I needed because I didn't have family connections. I didn't have a bunch of money. I didn't have resources that would give me some sort of unfair advantage. You know, there was no alpha that I had at this particular time. And I ran this t-shirt business all throughout college and we sold promotional t-shirts to universities across Canada.

26:46And again, I wasn't necessarily passionate about t-shirts. I wear a black t-shirt almost every day now, but I mean, I like t-shirts, but it wasn't my calling, was my life's work. But this idea of using entrepreneurship to solve the problem became very real for me. And then a mentor of mine convinced me to go to law school, not to become a lawyer, but to become a better entrepreneur. His hypothesis, which he was right about, was this t-shirt business has no unfair advantage. You have no moat around your business. This thing is cool right now when you're 19 years old or 20 years old. This is not going to be truly something that is worthy of your life.

27:27And he's like, but if you're not sure what it is, why don't you consider entrepreneurship finishing school? And this particular mentor happened to be teaching law at the University of Ottawa, which is the capital of Canada. And he's like, why don't you apply to the University of Ottawa? I'm teaching here, you'll go to school here. You'll know at least one person in town. And that brought me to Ottawa. And within a few weeks of moving to Ottawa, I met this brilliant programmer who just moved from Germany to Canada. He moved to Canada because he made a girl. He was now his wife. And this incredible programmer couldn't get a job because he was a new immigrant.

28:01But he's living in Canada. And he decides he would start selling snowboards on the internet. And he couldn't find any good software to sell these snowboards. It was either very expensive, like a million dollars, to build an online store. Or you were forced to sell on a marketplace. The predominant one at that point was like eBay, effectively. Amazon did not allow third-party sales at this point. So he wrote this piece of code to sell these snowboards. And he realized that the actual code that he had written to sell these snowboards was far more valuable than the snowboard business itself. And he would change his business model to focus on helping others build similar online businesses.

28:35And I met Toby around that time and became one of the first merchants to use Shopify and started selling t-shirts. It's so interesting that you went to law school under the idea that it could be or is entrepreneurship finishing school. Like I went to law school. Yeah. That was not my experience at all. You actually practiced that. Yeah, well, you did for a year, right? You did for a year. But you were like, you were a real litigator. But I will say, yeah, I mean, to me, law school was full of people like myself who are fundamentally safety seekers. They are the opposite of entrepreneurs in terms of their like risk tolerance, right?

29:15Like these are people who are looking for tried and true career trajectories. And those that did have a different kind of relationship with risk got worn down, right? So people come in, everybody's like, I'm not doing the law firm thing. I'm gonna do the nonprofit thing or I'm gonna be a DA or a prosecutor. Then the loans start to add up and they're like, well, maybe just for a year. I did the summer associateship. Everyone seemed nice and they took me out to nice restaurants. Maybe it's not so bad. I'll do a year or two. And once you're in, it's very difficult to get out. and I don't know anybody from my law school class who became an entrepreneur.

29:55So yeah, it's interesting. I do think you learn skills that are certainly valuable and applicable in an entrepreneurship context. And you did it, in fairness, you did like a joint MBA also, right? So it wasn't just JD. Which actually I didn't, if I had to do it all over again, there's not many things I would have changed about sort of my background. But one thing that I would have changed is I probably wouldn't, I didn't think business school is nearly as valuable. I actually think the skillset that I learned in law school was far more valuable than business school. Business school was mostly case study-based learning or, you know, pedagogy.

30:27But law school was read 4 ,000 pages and pick out the one line that matters most. I mean, that is a very difficult task. It is case study-based also, but you have to find, yeah, it teaches you a different way of thinking, a certain way of, you know, analyzing arguments to come up with your own argument and then like stress testing your ability to like tell a compelling story. I actually felt that I really didn't learn how to write very well until I got to law school where I was forced to write a ton. I mean, memos and, you know, just case breakdowns. But also it was things like the Socratic method in class.

31:02I don't know if that was how it was in law school, but in our law school, they would just yell out, Harley Finkelstein, like, please tell us about this particular case. And you only had a few minutes and you have to explain a very long case, a very complicated case in a matter of minutes. that in itself, I think was, was really, really valuable. I think most people on the law school point, most people, I get people messaging me all the time to ask me about law school, if they should go. I think that most people today look at education as simply a stepping stone for the, for, for the next stage of their life.

31:32So they go to medical school to become a doctor, they go to law school, become a lawyer. I think if you take a different approach education where you look at it almost like a transaction where you pay tuition and you need to receive this same amount of information, of knowledge, insight in return, like that's the contract you have with the academic institution. And I think if you walk in with that attitude and you're truly like, like be selfish about it. You're like, I'm giving you, in Canada, it's cheaper than US, but I'm giving you$15 ,000, which is what law school costs a year in Canada. I demand you give me$15 ,000 of insight and knowledge and experience back.

32:09And you're not as worried about exams because you don't need a job at a big law firm, you actually look at your day-to-day course load very, very differently. You begin to pick courses and professors who are much more interesting and inspire you. And you're less concerned about, you know, the famous Maxman College for me was like, you know, basket weaving classes or there was a famous class in McGill called the Art of Listening, which effectively everyone got straight A's in. Why did you take it? You took it because you got straight A's. I would never have done something like that because that wasn't actually a valuable exchange.

32:41I wasn't looking for the A or the grade. I was looking for selfishly to derive as much insight as I possibly could. And I actually think a lot of the things I use today on a day-to-day basis, you know, leading a large company, I got from law school. I did not get from business school. But you went into it with a conviction and a sense of self and, you know, kind of an understanding of where you wanted to go. I think most young people don't have that level of self-understanding or conviction. It is very helpful to know what you want earlier in life. Yeah, yeah, yeah. There's no doubt about that.

33:13I mean, it's a gift. It's like, you can't make yourself that, you know, like that just, some people have that, some people don't by dint of circumstance or experience. And I think law school is a place where a lot of people, myself included, kind of go when they're not really sure what they wanna do, right? Hopeful that they'll figure it out along the way. You know, it's a career purgatory. Yeah, you're sort of being warehoused while you figure out these other things. And the good news is that if you want, you can go and make, you know,$250 ,000 a year out of school after school, right? Like, it's purgatory, but there is like, there is a default next step.

33:46And that default next step is like by all - The safety net is very high. It's very, very high there. And it'll just continue on.

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39:13I like what you said about this transactional kind of relationship with the academic institution. And on some level, I think that is perhaps a function of the world being very different from when I went to these schools because of the internet. Like now the aperture is so wide, like you can see what all these other people are doing and you can listen to podcasts about how they did it and why they went to law school. And the number of paths is infinite. Whereas when I went to school, that didn't exist. It's sort of these very, you know, kind of well-defined tracks. and anybody who stepped outside of it was sort of not a pariah, but like a little bit weird.

39:56You know, like when I was growing up as a kid, I don't think I ever heard the word entrepreneurship once. There was no such thing as entrepreneurship. I mean, there was, but it wasn't like a word that people were saying out loud. Basically it was business, right? And if you wanted to go into business, you go to college, maybe you get an MBA and then hopefully you get a job at General Foods or General Motors or Procter and Gamble or Boston Consulting or Morgan Stanley or someplace like that. There was no kind of thinking or incentivization around the idea of like striking out. If you were gonna strike out on your own and start your own business, that was like, oh, you're gonna have a sandwich shop.

40:34Or you failed, you didn't get the job. So this is sort of your backup plan. And the internet didn't exist. So the capacity to like scale anything was impossible without capital and all the things now that has been democratized in no small part because of Shopify and the tools that you make available to people, which has changed everything. And, you know, I was so myopic. I was at Stanford in the late 1980s when all of this was being born around me. Right there. And I was disinterested. Like it never occurred to me while I had classmates dropping out to go start their businesses, I thought they were insane.

41:03You know, it's like, I'm very late to this party and somebody who became an entrepreneur, you know, in the later decades, but the world is very different now. And now being an entrepreneur is sort of this aspirational kind of rockstar thing. It's very cool. I do think there's one exception to this sort of philosophy or theory that we're talking about, which is immigrants. My father was an immigrant. And obviously his parents were immigrants also. He came to Canada when he was very young. He was, you know, five or six years old. They came from Hungary to Canada in 1956. My grandparents were Holocaust survivors.

41:36They came. My grandfather was effectively an entrepreneur. He didn't call himself an entrepreneur. He never articulated that as his life's work. He sold eggs at a local farmer's market in Montreal, which still exists today. It's called Le Capitain. My uncle currently runs it. He did that because he had no choice. And so this idea of forced entrepreneurship is something that I've been thinking a lot about more recently, which is that a lot of immigrants have to become entrepreneurs because they don't have a job. They don't have the sort of skill set. They don't speak the language. And so no one gives them an opportunity.

42:06They must go into it. And then ironically, what tends to happen on the next generation that I've noticed is that a lot of them want their kids to become doctors, lawyers, accountants. Yeah. So the people who actually have the most amount of entrepreneurial role models, which are children of immigrants like me, are pushed into like law school and medical school and engineering and accounting because they believe that they want a better life for their kids than they have for themselves. And I actually think that there was something to be said about like being forced into a particular direction, especially as an immigrant.

42:38Like you just you get very resourceful. You tend to be anti-fragile to use a Nassim Taleb, you know, sort of line. I think that more people need to experience or know people that are entrepreneurs in order for them themselves to consider entrepreneurship. My father made me the business cards, not because he thought I'd be a good DJ, but because to him starting a business was not that foreign. And it wasn't because he was sophisticated or inspiring or this, you know, this, this entrepreneur group, not at all. It's that in his upbringing, he saw people start businesses. And so if his son wants to start a business, that doesn't seem so crazy.

43:14And I don't know how to sort of bring more of that back. Actually, I recently just wrote a kid's book about entrepreneurship because my kids are in third grade and kindergarten and they're, they, they're both doing these projects called what do you want to be when you grow up, which is a very common project for children to do. And they brought home their assignment and it was literally like circle what you want to be when you grow up. And I had two major issues with this. One was entrepreneurship was not on the list, which I was devastated to see. And second, it was all about what you want to do later in life.

43:47And I think that I was fortunate that no one put that in front of me when I was their age, because if they did, I probably would have pushed out this idea of being a DJ until I was quote unquote grown up. And so I wrote a kid's book effectively about me becoming a DJ at 13 years old. And I used a couple of examples of Shopify merchants. One was 10, one was 12, started what would become multimillion dollar companies in their garages when fashion, the other is an artist. I think role modeling is really important. And the original role models for entrepreneurship, I think are immigrants. And that's what it was for me.

44:21100%, that's so true and very insightful. And it's always for us as a parent myself, when in school they're meant to do some exercise. And by definition, it's like a limiting exercise, whether it's art class and you gotta draw within the lines or whatever it is, anything that is an imposition on a child's creativity and expansive kind of perspective of what's possible is infuriating me. And so it's full circle, but I took an entrepreneurial solution there. I met with the administration of her school. I met with the teachers. I met with the principal and I said, I think you need to have more entrepreneurial curriculum.

45:00And I got a bunch of hand wavy stuff. My kids are at a different school now, but I got a bunch of, that's true. But I got a bunch of hand wavy stuff. And the reason I wrote the book was I needed a Trojan horse. I knew that convincing them to create a curriculum, they would say, we have to go to the school board and all that stuff. but I knew that if I said, hey, I wrote a book and I'm gonna pay for these books, if you like the book and you agree it's a good book, I'm gonna pay to have the books distributed in your school. They would read the book and perhaps someone would take the initiative and create an entrepreneurial program.

45:32And that's what I did. I wrote this book. I mean, I really like it. I read it to my kids all the time now. But I created a Trojan horse. I took an entrepreneurial approach that they weren't gonna listen to me otherwise. So here's a book about entrepreneurship that I think your teacher should read to the students. Tell me what you think. and it, at least in this particular school, it worked. What are you gonna do when your kids wanna be doctors and lawyers? Good question. You know, my wife, who's much smarter, much more thoughtful of a parenting than I am, she's also a psychotherapist, has often reminded me that as much as, you know, we are the entrepreneurs and my wife's a psychotherapist, she's also an ice cream entrepreneur, like entrepreneurship is, like, our house is full of ideas.

46:11We're always talking about new ideas, new projects, new cool things that we were excited about, that there is a chance that one of our kids or both may decide to be professionals, the thing that I loathe. And I think that's okay. I think what matters to me more is like, I want them to be people that really give a shit about being lawyers or being doctors. I didn't care about being a lawyer. And that I give a shit about the thing, that's actually what I want from them more than I want them to take a particular path. Sure. Do you think that everybody can be an entrepreneur? You're certainly wired that way.

46:50But do you think everybody can have that inclination as somebody who's kind of democratizing this world? I have two thoughts on this, and they're somewhat contradictory. One is that the cost of failure has never been lower for entrepreneurship. Going back to my grandfather's story, selling eggs, he comes to Canada from Hungary, has no money, eventually makes a little bit of money just working odd jobs, and gets a little egg stall. if that egg stall would have failed he wouldn't have just lost the egg stall he would have lost his house and he would have not been able to put food on the table like the cost of failure in the 50s of entrepreneurship was massive today it's not today if you you know this is not a pitch for shopify but for 39 a month like price of a couple cups of coffee you can start a business and you and i were talking just before we started recording about you know being here in los angeles in meeting some of these merchants.

47:43Some of these merchants that I met with the last 24 hours here, they're some of our largest merchants. They started this business at their mom's kitchen table less than a decade ago. And today, those are billion dollar companies. So the cost of failure, I think, has never been lower. And the velocity of business growth has never been higher. I don't know the Nike board. I'm sure they're nice people. But I suspect at some point inside of a Nike board meeting, the name Gymshark has come up. someone said who is Gymshark how did they get so big so prolific so important so quickly Ben Francis started that at his college dorm room in the UK 2012 we've never seen companies grow this fast this quickly and as prominently ever before so cost of failure is low and the ability to scale has never been higher like the internet sort of democratized scale in some ways okay that's one side.

48:36On the other side, I get criticized fairly regularly that I believe that everyone should commercialize everything about their lives, that every hobby should be commercialized. So I don't think that every hobby should be commercialized. I think if you make beautiful blankets for your grandkids and you're listening to this right now, maybe you should just keep making beautiful blankets for your grandkids. But if you really love making those blankets and you're finding yourselves running out of grandkids to make it for, maybe you should set up, you know, bubbysblankets.com. And maybe you should just, you know, go to a, yeah, go on, if you're a grandmother, maybe go to Facebook and you go to Facebook group and you look up a bunch of forums where people are looking for beautiful hand knit products.

49:19And maybe you should just put a link there and say, here's an idea. What do you think? Here's a product. What do you think? And let the world gauge whether or not there's a there there. I want to be careful because I don't think everyone's hobby should be commercialized. Some hobbies should stay hobbies. But I do think that there's a lot of people out there that have these ideas in the shower consistently and perpetually. And for some reason or another, they're scared of the cost or they're scared of the lack of understanding. And they don't do anything with that idea. And that idea may have the potential to be a billion dollar company or maybe just, you know, a company that makes$10 ,000 a year and that's all you want because that pays for ballet lessons for your granddaughter.

50:03I don't think everyone should be an entrepreneur, but I think there are still too few people that are considering entrepreneurship as a meaningful life's work pursuit. And, you know, I've said this a lot and I really believe, I think this is the golden age of entrepreneurship. And I think it's the golden age of entrepreneurship because the cost has never been lower and the distribution channels have never been higher. One of those first stores on Shopify in 2006, I was selling t-shirts. At that point, even 2006, so not that long ago, less than 20 years ago, the key ingredient for success on Shopify was who can spend more on AdWords.

50:38Right. And I couldn't outspend Walmart. So no matter how good I was at entrepreneuring, I was never going to build something that would compete with Walmart in this particular vertical of licensed T-shirts. That's different now. Now, I met a company, Rocky's Matcha, a Los Angeles company. I met him yesterday on Venice Beach just to hear his story. And he's telling me his story. And he said this publicly, so I don't think he'd mind me sharing this. But he's never spent a dollar, not one dollar on paid advertising. And he's built one of the most important modern matcha companies, like in America, simply by hustle and grit and great product and being at the right coffee shops.

51:19And that's why I think right now is such a great time to do it. And so to answer your question more directly, no, I don't think everyone should be an entrepreneur, but I do think that there is a lack of people that are trying it, who I think could be very successful at it. There's something generative about it. Obviously you create something, you offer it to other people. And if other people enjoy that, there's a connection, there's a sort of community building piece to it. And it's very self-affirming. There's a sense of agency over your life because if you're in a corporation or go to a more kind of typical nine to five job, you can perform your job well and you can be well-reviewed and all that sort of stuff and feel good about the work that you're doing, but it's always on behalf of somebody else's mission, right?

52:02And when it's your own mission, there is something just incredibly uplifting about that. I'm interested in this thing that you said that stuck out to me, which is entrepreneurship is the greatest tool to self-actualize, to solve a problem, to find success, and to find ourselves. So what I gather from that quote, and please tell me, is that it's like this lever for personal development on some level. Like it's more than just business, you know, creating some independence for yourself, whether it's a side hustle or your main thing. So earlier we talked about balance. We talked about this idea of enough and side quest and main quest and all that.

52:45The flip side of it is that I don't necessarily think this idea like that your work life and your life life need to be disconnected. And I think one of the best ways to merge those two things is through entrepreneurship. Now, again, the caveat is I'm not suggesting that every hobby should be commercialized, although I think a lot of people's hobbies could be their incredible ventures. And some of the best businesses on Shopify started as someone's hobby became a business that eventually became Figs. because Trina's company, FIGS, now publicly traded billion dollar company making hospital scrubs, which is amazing business.

53:18So I see that very, very often. But I think the greatest way for humans that I've seen to find their thing, to be more creative, to solve their problem, but also just to like enjoy their day-to-day is through entrepreneurship. And it's not to say it's easy. In fact, you know, I think I often may glamorize entrepreneurship and often may neglect the fact that most businesses do fail. Yeah. Even those hobbies that become giant companies, I mean, there's a trail of tears. For sure there are. These things are - They're not always going to be successful. That's exactly right. And in fact, you have to keep almost like reinventing your business as time progresses.

53:59But I do think though that access to entrepreneurship as a tool to find your thing was not possible to the extent that it is today, even 15 years ago. And it wasn't just Shopify. I mean, the internet, technology, a lot of these things are sort of creating this as well. Consumers. Consumers today are voting with their wallets to buy from brands that they love. You and I talked about a bunch of brands before we got on today. Those brands, when you buy from some of those brands, when you buy from Viore, for example, at least when I buy from Viore, one of my favorite brands, I'm not trying just to buy a pair of shorts or a t-shirt.

54:32I'm also voting with my wallet to say, I want more of those companies, those brands to exist in the world. Yes, I like the more traditional big box brands too, but I think what Viore is doing is fantastic. The way that I can support them as a consumer is by buying from them as well. So I think consumer choice for a long time, it was, I will buy direct from the brand or the merchant if it's really convenient. And now I think it's actually gone past that, which is consumers actually prefer to buy direct from the brand or the merchant whenever possible. And that's a switch that only happened the last decade.

55:08Part of it was, even though you could buy from, you know, a direct brand, an independent brand, it was less convenience. You went to a big box store, returns, you know, the cash register was right there. They had your information on file. But now, you know, using a term we both learned in law school, sederies, parabas, all things being equal, I think consumers prefer to buy direct from the brands that they love. And so when you line up all these things, technology, distribution becoming democratized, and consumers' preferences and how they purchase changing, you end up with this incredible surface area of opportunity.

55:45I have a pretty good purview of entrepreneurship, I think, from the seat that I sit in. And the people that I speak to that have left the job they didn't like or found success using entrepreneurship, they're pretty damn happy about it. Yeah. I've noticed that in my own personal life. Like most of the things that I buy, like apparel stuff that I buy is based on what I see on Instagram. Like the algorithms figured me out and it sends me cool stuff that I'm like into from companies I've never heard of before. And I'm like, I'll try that. I don't know if it's, it looks cool. We'll see, you know, I'll take a flyer and thanks to you, like it's one button.

56:23Yeah. Shopping is pretty good. Pretty easy. You have, you have, you've been instrumental in helping me with all the money in my wallet. That's right. But I love the shop app and then it, it, it tracks everything. So you know exactly where everything is and when everything's coming, which makes me feel more comfortable about like, oh, I didn't, I forgot about that thing that I ordered and who knows what happened to it. Yeah. But even in terms of your, I love these little brands that, that, that show up and I'm like, that looks really cool. I would have never known about this. And now I've become loyal to certain tiny little brands because they over-delivered and I love their stuff and I continue to buy from them.

56:58And those little brands that over-deliver, that over-delivering is often something that the large companies cannot do. They can't do it. Because it doesn't scale well. There's a great brand on Shopify called Tecovis, which makes beautiful, beautiful boots, like boots, like cowboy boots. I'm not a cowboy, I'm a sneaker guy, but they make beautiful boots. And one of the coolest parts is they have about 40 stores across America right now, great online store. And I've got to know this team really, really well. They have a bar in every store. and not like an unironic bar. You know, a lot of retail stores added DJs and coffee bars and they have like an actual cocktail bar and it just, it fits perfectly in there.

57:31And one of the things they are able to do is they're able to get to know their customers so they know your drink. That is something that works with 40 stores. It doesn't work with 4 ,000 stores. So the brands that are over-delivering, part of the reason they can over-deliver is because they're able to have this one-to-one relationship with the consumer, but it's also reciprocated by the consumer. The consumer is now saying, if I need another pair of boots, I'm going to go back to this particular store. I have a relationship. And I don't think we as humans have historically, like, you know, hundreds of years ago, you bought the bread from the baker and you bought your shoes from the cobbler and you went direct to consumer.

58:06And then you had this like this 200 year period of intermediation. And actually the person who caused that was a guy named John Wanamaker. 1876 created Wanamaker's department stores in Philadelphia. That was the first time that a bunch of stores were under one roof in America, sort of the origin of the department store. And if you sort of track, essentially from that point until 10 years ago, retail was pretty much the same. Bigger stores, they added, you know, bigger food courts. Some of them had like, you know, go-carts or they had, you know, water parks. But it was basically the same thing.

58:40And it's only been the last 10 years or so that retail feels really exciting again. And why? It's because people that care about the things that they use. I care about this pen. I think it's a really great pen. I really love this Moleskine notebook. These things matter to me. I selected this intentionally and this intentionally. The people that care about that stuff, we are finding more joy and more delight from brands that tend to be independent modern brands. And that's what's creating all of this, which means that if you have an idea and you want to create something that doesn't exist yet, you will likely have an audience somewhere in the world for your particular product.

59:14And it's easier now to find than ever before. And when those customers feel well taken care of, they become the evangelists of that brand. Totally. Where is your head in terms of the future of retail? Like we're in a really interesting moment right now. It's cyclical, obviously. We went through the pandemic and I know that was a sort of a crucial moment for Shopify, but we saw the retraction of retail, everything closed down. And now we're seeing the reemergence of retail, but retail seems to only work when they've eventized the experience. Like there has to be like going to a movie, like there has to be something more than I'm just going to the shop to get my thing.

59:58It has to be an experience that's been cultivated. And that seems like what works best. So even the most ardent like digital direct-to-consumer brands are now opening flagship stores in fancy parts of metropolitan cities across the world. those are capital intensive things, right? So where's your head at in terms of like where retail is headed and what the future of retail looks like for those smaller, cool brands that are doing well on Instagram, but aren't gonna be opening up an Apple store type experience on Broadway. Yeah. There are these brands that just really, really understand their consumer.

1:00:39The best example I can give you is Shopify Merchant that was one of my like, I have a bunch of these like Moby Dick's, these like big brands that I really want to get on Shopify. One of my big brands that I really want on Shopify was Supreme. I think what Supreme has done, not just for skateboard culture, but just from retail is nothing short of remarkable. Here's a company that every Thursday at 11 a.m. Eastern Standard Time, they have a flash sale, Supreme.com. When you go to the flash sale, like you go to their online store, it's not easy to navigate. It's sort of a puzzle. You see little slivers of the different products, a skateboard, a t-shirt, a hoodie, whatever.

1:01:19And the loyalty and the connection that the consumers, the fans of Supreme have to them is enduring. I mean, Supreme's not a new company, right? They've been sold a bunch of times. I think VF Corp just sold them to private equity, but they have a really good understanding of what they do very well. If you've been to a Supreme physical store, it's not that nice of a store inside. It's kind of a warehouse, but they have a really good understanding of it. And there's always a line. On Lafayette Street in New York City, every time you go by there, there's like 50 to 100 people in line waiting. That's exactly right.

1:01:50Right down the street from there is Kith, who also has a line, but very different experience. Inside, it's like a beautiful museum. There's Kith Treats, beautiful ice cream bar. There's a lot of art. I know you're into bare brick. There's bare bricks everywhere, right? The like, cause dolls. It's an amazing experience. They're a streetwear brand that just did a collaboration with Giorgio Armani. And Martin Scorsese is sort of one of the, like, was the model there. Those videos, I've seen those videos with Scorsese. So you have that on one side. On the other side, you have brands that... I mentioned, I'll mention this brand again, Figs, who realized that doctors and frontline workers and nurses in the hospital, in doctor's offices, in the clinics, they were all wearing these kind of shitty scrubs.

1:02:37They didn't look good. They didn't fit well. It's just, it was basic. And we can do this better. And they completely disrupted that market. And they have figured out a way to really tap into frontline workers. They work with hospitals. They figure out a way. During the pandemic, they actually put up a job site to help frontline workers find new work. If their particular clinic shut down, there'd be another clinic. I think there's a timelessness to this strategy, which is deep empathy for your customer. And if you really understand your customer, you do really, really well. A couple of years ago, this isn't a strike against Starbucks, but I remember talking to my niece about Starbucks and her telling me that she no longer goes to Starbucks.

1:03:16I said, why? And it was something to do with, they changed their points program. and my niece wasn't really into coffee per se, but she loved her Starbucks point card. It was this point of pride for her, this like special card she had. What Starbucks missed in that transaction was the people that were coming in there, some of them really loved coffee. They were coffee stumps, but a lot of them were simply like, they believe in this loyalty program so much. When you changed it, it was almost as if they kind of forgot about who they were serving. When you look across the millions of stores on Shopify, the ones that are most successful are the ones that have deep empathy.

1:03:51From a sales channel perspective, what that also means is Kyle Leahy's CEO of a company called Glossier, amazing cosmetic company. If you ask Kyle, during the pandemic, the reason I bring this up is during the pandemic, while everyone was shutting down their physical retailers, Glossier was opening new stores, physical stores, making beautiful stores. So in anticipation that when the pandemic lifts, they are going to have these amazing in-store experiences. But if you ask Kyle about, is Glossier predominantly online or offline? she'll tell you that's the wrong question. She'll say that we are everywhere our consumer wants us to be.

1:04:23And right now, the consumer for Glossier wants to go in store, but they also want to buy online. And they also want to shop on Instagram and on TikTok. And so as their commerce partner, we have to be in all those places. We just announced a commerce partnership with Roblox two weeks ago. Why? Because some brands, some of the time, are going to want to sell inside of Roblox because that's where their customers are. That doesn't mean that Kith should sell in Roblox. It means that some other brands that really have an empathy for their customers and those customers spend time there should sell there too.

1:04:52So my belief is that the future of retail is not online or offline, it's retail everywhere. And every single surface area that exists where consumers and humans spend their time should be a potential place to have a transaction. Not because we need to commercialize the world, but because it's more convenient that way. And one of my favorite brands is James Purse. I wear a black t-shirt, usually made by James. James is also a good friend. I think he's one of the best entrepreneurs on the planet. I had lunch with him before coming here. Tell him to lower the prices on those T-shirts. It's quite expensive.

1:05:24But it is insane. But I mean, I'm wearing, it's my suit. I have a few, but it's like, it's very expensive. I can't justify this. So James has a bunch of James House, James Purse villas in Cabo. And these villas are fascinating, not because they're villas and Cabo is a nice place too. But when you rent these houses, anyone can rent them. You're in the James Purse universe. Like it's an experience. It's sort of like Armani, right? Like it's all curated. Like the aesthetic is consistent. Except he goes one step further. He knows your sizes. He knows what you've bought because he's got a great CRM.

1:05:56He knows everything about your purchase history with their brand. So when you go into your bedroom and you open up the closet, there are stuff there in your size, presumably stuff you don't already have that may actually match well with the stuff you do already have. And you can simply take a photo of it or you can scan it and you can easily transact. On hangers that are all like exactly. Exactly one inch apart from each other. And, you know, I kind of love that. Yeah, yeah, yeah. So if another brand went ahead and did that, it wouldn't make any sense. But if you know the James Purse brand, you know that it's very.

1:06:27It's consistent with. Design, architecture. James makes the playlist for all his stores. He picks a sense of all the stores. The floorboards in his stores are perfect. Not perfect for any store, for James Purse stores. And I think that is something that is a timeless strategy around empathy and authenticity. And I don't think that's going away.

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1:08:30What's distinctive and interesting about Shopify is at the beginning, you identified a need in the marketplace. Like nobody is doing e-commerce software that's consumer-friendly and available. There's enterprise software, super expensive, but there wasn't really a solution for the average person or the hobbyist, et cetera. You would think with that, okay, we're gonna fulfill that need. And then that is our customer base that we're gonna serve, the people that can't afford the high end. But today you're serving everybody. You've got Fortune 500 companies, these gigantic legacy companies, but you're still serving the mom and pop shops, right?

1:09:11Like walk me through like how you've been able to kind of serve all masters in that regard without like losing focus. And whether at some point there was a conversation like, hey, listen, we need to choose here. Like we can't be everything to everybody, but somehow you figured out how to kind of do that. We went public May 2015. and in February 2014, we introduced effectively our enterprise plan called the Shopify Plus. And the reason we did that was what happened around that time was a bunch of these really small businesses got really big on the platform. So those stores that started their mom's kitchen table, which frankly, no one really knew what's going to happen.

1:09:51Some of them started to do like a hundred million bucks a year,$200 million a year. I was like, wow, these are big businesses now. They didn't leave the platform. There wasn't this graduation off the platform. So let's use email marketing. With most software like email marketing, you'll start with like the BCC line is what you'll use. And then eventually you'll upgrade to like, I don't know, MailChimp and eventually Constant Contact. And eventually you'll upgrade to like ExactTarget. There's like enterprise software line for email marketing. Same thing with accounting, right? Maybe you start with QuickBooks and eventually you end up with like Oracle Financial or NetSuite or something like that.

1:10:23In most software verticals, there is this natural graduation as you get larger because the things you need when you're starting, which is like, you know, you like very simple, you use it sort of consumer friendly. It's exactly the right term. The UI has to be simple. You can't overload the features. Otherwise you get sort of the paradox of choice and you spin. You need things that are very, very simple to use and not intimidating, especially if you're starting a new business. But when you're Supreme and you're doing massive flash sales, the requirements you have are totally different. Or if you're Mattel, for example, which is another one of our stores.

1:10:58So 2014, we create this plan to allow small merchants that get really large to graduate to with additional functionality, with additional, you know, API call limits and additional throughput in case during a flash sale, things like that. And that's sort of where we were sort of sitting for a while. It was the best place to start a brand new business. And in the case that your business gets really big and really successful, you never have to leave the platform. IPO happens. The IPO, most people don't talk about it this way, but the IPO is not just an interesting event internally, but it also provides, I think, it's almost like an external branding moment.

1:11:35Like all of a sudden, people that are not in e-commerce started hearing about Shopify. We started to get phone calls from more traditional companies, companies like Staples, for example, or Mattel, for example, or Procter & Gamble. And they were interested in looking at Shopify. And we were fascinated by this. We're like, you know, most of them have custom stacks or they're using some sort of big enterprise software. Why would they think about Shopify? Well, it turned out that even though Shopify was software built for entrepreneurs, that in these companies, there were these entrepreneurial people.

1:12:05I hate the term intrapreneurs. I'm not gonna use that. But there's these very entrepreneurial people in these companies. And they were sick of having to do service calls every time they want to add a SKU. They're like, it doesn't make any sense. We just want to change something. We have to call some big enterprise software company. It's ridiculous. The cost was insane. And so what happened was a lot of these very large brands began to act like entrepreneurs. And in many ways, they sort of stretched us up, Mark. They said, well, we know you don't have everything, but we think we can do everything we need as long as you...

1:12:34What they said to us was, as long as you make the important things easy and everything else possible, we can use Shopify. And so that was sort of the philosophy we used. make the important things really easy. So setting up a payment account, getting a domain configured, picking a theme, adding products, doing basic order fulfillment, doing basic marketing on AdWords or Instagram ads. That stuff has to be incredible, whether you're small or big. But then all the other stuff, I want to sell internationally. I want to do B2B wholesale. I want to add a point of sale terminal so I can sell in my physical stores too.

1:13:07We made all that possible for them. And the real trick to this whole thing was the complexity of the software needs to reveal itself only at the time that the merchant requires it. Because if it reveals the complexity too early - It's disorienting. It's the worst thing in the world. You're gonna confuse them. And so we made a very conscious decision. We're not going to shift up market, but rather we're gonna stretch up market. And we wanna be the place where everyone goes to start a business, but we also wanna be the place that modern brands, it doesn't mean they have to be like new, but modern thinking, modern like entrepreneurial brands that are even very large ones, can also go to run their entire stack.

1:13:47And that's the reason why we have such a large cohort now, a very large enterprise business, because as they grow, they can do all that with Shopify. The other thing that's important that we got criticized for on the IPO, but now things seem to change a little bit as sort of commerce evolves, is that we don't just want to be e-commerce. We want to make it easy to sell across every single surface area, as I mentioned. So what ShopLite really is today is more of a retail operating system than an e-commerce platform. And why does that matter? It matters because there's going to be a time in the future that someone comes supposed to sell a product and the only place they want to sell it on is augmented reality.

1:14:29They're not going to have an online store. They're not going to have a physical retail store. They're just going to be powered inside of like, you know, some sort of goggles. Apple Vision Pro situation. Or the Orion glasses from Med or something like that. Or within some video game. Correct. No one is looking for that right now, but Shopify has to build stuff like that in anticipation that when they're ready, they simply go to the admin and click AR channel and it activates. And so that's kind of how we're trying to think about this idea of modern retail and modern commerce, which is whatever size you're at, if you want to do, if you want to sell across any platform in any country, if you want to be default global, if you want to scale, do massive flash sales, you can do so with us.

1:15:07And that's been a huge challenge from a product and technology perspective. Every company has a life cycle, seasons, things change. You were at Shopify in the very beginning when it was, you know, Tobias and you and everything was very exciting. And perhaps that leveraged the best of what you could offer as an entrepreneur. But as companies grow and scale, then they become institutions, right? And you're faced with the prospect of doing all sorts of things or being responsible for doing things that are outside of your core skill set or your passion. You got to manage people. You got to deal with spreadsheets and account, like all this admin stuff and everything that gets packed into it.

1:15:47So how have you navigated that for yourself as an entrepreneur to stay fresh and make sure that you're leveraging the best of what you have to offer for the benefit of the organization, while also simultaneously making sure that your employees and your staff are well-situated? We all know the story of, you know, people who do really well at their job and then they get promoted, they get a better salary, but suddenly, you know, they're doing a job that they're ill-suited towards or one that, you know, doesn't give them the level of satisfaction and fulfillment. It's called the Peter Principle. There's a term for it.

1:16:20Yeah. Peter Principle is eventually getting - See, if I went to, if I went, if I got my MBA, maybe I'd know that. You would have known that. Yeah. It's a silly term. I don't know who Peter is, but - They didn't teach that in law school, so. Yeah, unfortunately they did not. I think at the early stages of most companies, especially when you have a small team, there are no, you know, dedicated roles. It's the only question you should ask yourself is how do I have the most amount of value? And when I came to Shopify 15 years ago, it was a group of engineers, very, very smart. And the only thing that the only thing that I had to do is figure out a way to do the things that no one else was doing.

1:16:55We didn't have a CFO when we raised our series A. We didn't have a chief marketing officer. we were a scrappy bunch. And so I played this sort of, you know, what's now known as like the Swiss army knife role. How can I help? How can I be most valuable? How can I have the biggest impact? I think that's the only way to get through those first couple of years. I think if you begin to self-identify of a particular role or give yourself a particular title, you end up in a box. And that's not what early startups need. Early startups need people that are just doing a lot of different things and just trying to keep your head above water.

1:17:24There's no room for, um, for selective roles. You just, you kind of have to just get it done. Unfortunately, what ends up happening, as you sort of articulate, is that as you sort of get bigger, that doesn't, there's no, there's no like threshold where you're like, okay, now I'm going to specialize. On a very personal level, there were people that I admired at other very large companies, much larger than Shopify, who sort of played these, the role that of sort of business leader or, you know, They were like really good at a lot of things. They were good at like operations, good at finance, good at marketing, good at product, good at engineering, kind of good at everything.

1:18:03And I was like, wow, like that's kind of what I think I have to be. With the benefit of time and hindsight, I realized I made some, that was a mistake that I ended up, there was a period of time where I was the chief operating officer of Shopify, COO of Shopify for about five years. And I care so much about Shopify and I care about impact and performance that I figured it up to the best of my ability, but there was no way, absolutely no way I was ever going to be the best in the world at that particular role. It wasn't what I was thinking about in the shower. It wasn't my ground state. It was only in the pandemic where things got a little crazy at Shopify.

1:18:44We ended up divesting a fulfillment business. We ended up having to do some layoffs from 14 ,000 people to about eight or 9 ,000 people. We effectively turned over our leadership team and brought in some new people. It was this great opportunity for us to sort of rethink how we want to run the business. You know, the credit goes to Toby on this that he was really thoughtful, but he's like, we don't all have to be good at everything. However, the thing that we are doing, we have to believe that at some point we can be the best at the world at it. And what that meant was he was going to be the chief product officer.

1:19:16He was, he believed like, and he's correct on this, that there was no one that was going to build a better product for the company at the highest level than he would. and we would find someone to actually take on the role of COO who loved operations, who loved those details, making sure the trains run on time. And there happened to be someone in our company, Kaz, who was very much like that. He's been our COO since that time. And I really wanted to be the storyteller. I wanted to be the person that told the whole world about Shopify, investors, media, the public, merchants, entrepreneurs, everyone, partners.

1:19:49and internally I want to be the person that story tells culture onboarding making sure that that we are all pointing the right direction and I think for a long time I didn't know if that was good enough that if that was enough and it was only when Toby said look like this thing that that you love doing this storytelling thing like that is super valuable do you think one day you potentially could be one of the best in the world at this thing. I was like, I think I can, I'm not there yet, but I think I can do this really well. And he's like, well, then stop being well-rounded and start being a very pointy object.

1:20:27Don't worry about the well-rounded. Be self-aware enough to know what you're not good at. Hire the best people in the world for that stuff too, but keep sharpening your point. And the metaphor that I like to use for this is like, when companies get larger, you put these beautiful, like spiky rocks in the riverbed and over a long period of time, they become smooth and they become like river stones. And that's what I think happens with corporate inertia that we all could become well-rounded because I know it's not your job, but just try this on. And I know you're not really good at that, but just take this like we have no, it's a holding pattern, but let's just do that for now.

1:21:01And eventually you end up with these roles that are, you have to kind of be well-rounded. And I don't think there's any real alpha in that. And one of the terms right now that's very current, very kind of like the cool term in tech is - Founder mode. Founder mode, right? Yeah, everyone's talking about founder mode. I had that written down as something to - Founder mode. Well, it's not, there's - There's sort of like alpha male, like virtue signaling or something. It's holy, right? Yeah. But also, all it means is like, you need to be in the details. You actually like, founder mode, and I'm sure there's, I'm sure people are gonna be using it to excuse a ton of bad behavior as well.

1:21:37But ultimately, what I think it, what it describes is this idea that there is this trust battery of legitimacy that founders and early people and leaders get when they've been around for a long time. And you can deploy that legitimacy. You can deploy that trust battery and say, look, like this thing really, really matters. We have to do it this way. I'm certain of it. And I'm certain of it because I have 15 years worth of precedent that suggests that this is the way we have to do it. And I think it also speaks to this idea of micromanagement, which has a connotation of being a very negative thing.

1:22:12And I'm certain, at least today in my role in the storytelling side of Shopify, I probably micromanage. I don't think that's a bad thing. I think the people that work with me don't think it's a bad thing either. If I care that much about a particular, you know, sequence of words on an earnings call or in a press release or on a tweet or an ex post that we put out there, it's not because I don't trust them. It's because I really give a shit. I really want this to be really fantastic and really impactful. But I think this idea of moving from well-rounded objects into pointy, like sharp points around a particular skill set, first, I think it's more impactful, but also it means that I think you get more longevity.

1:22:58You get more longer tenure from the people that are really fantastic at your company. If you can identify what, and that's really what Toby did for me. He identified this thing that I didn't have a name for and said, storytelling. You are really good at that. That is super impactful. No one else can do that like you can. Just do that, but do it better than anyone else on the planet can do it. And that's the requirement. That's sort of the exchange. That's the agreement we make. And then every year, you must requalify. Now, that's really difficult because if you think about law two of ecology is that for a species to survive in any environment, the species must grow at an equal to or greater pace than the environment changing itself.

1:23:37It's kind of like that at companies. And at a company like Shopify that is growing, you know, last year, last quarter, our, you know, let's use revenue, for example, our revenue grew above 20 % year on year. Shopify is growing 20 % year on year. I have to grow at an equal rate or greater rate to that. That gets really, really difficult. I think that's incredibly motivating. I think that is like, I'm here for that. I find it uncomfortable, I find it challenging, I find it exhilarating, and it means that it doesn't get stale or boring for me. But also, how do you know, like, yes, okay, I need to grow and my growth has to outpace the growth of this behemoth that I'm in charge of, but what does that actually mean?

1:24:20Like, what do you mean? Like, how am I supposed to do that? In which ways? And like, where is the growth that awaits me that I need most in order to, you know, be able to interface with the growth that's coming up behind me right here. Like there's an uncertainty. It's really difficult because quantifying Shopify's growth is very objective. Quantifying my growth as a leader is very subjective. Part of it is, do I believe I'm doing a better job than I did a year ago? If I watch an interview that I did or a call that I did or a partnership deal that I did, if I did it now, would I do it differently?

1:24:55Would I do it better? What did I learn from that? So some of it is just sort of like internally motivated. And some of it is we have a board, we have investors. What do they think? How do they think I'm doing? And it's also where, you know, having really good mentors is really helpful because if you have a really good mentor, they don't just teach you stuff. They also call you out and stuff. Sure, they're gonna be like, you've gotta have those people around. You need those truth tellers. But that I think, that's sort of how we run the company today. Shopify is not a group of well-rounded people.

1:25:28Shopify is a group of spiky objects that all are very committed to their particular craft and are committed to being some of the best people in the world at doing it. And it certainly makes for more, you know, colorful meetings and offsites, but, you know, we're not here for second place. Yeah, I like what you said about the sort of conundrum or tension between ideas like founder mode. You have to be granular about everything. You gotta have your, you know, roll up your sleeves and you're in the details on every single thing or you're not worthy of the founder status, right? Just relentlessness.

1:26:05But you can't grow unless you delegate and trust those people to do their job. And both of those things are true, right? And so the job really is how do you reconcile those on a case-by-case, minute-by-minute, individual-by-individual basis. There's a great metaphor that I love, which is the trust battery metaphor. We talk about this a lot inside of ShopPly, but basically everyone that starts at the company starts at 50 % trust battery. Again, the trust battery is a metaphor. So you're not gonna go up by 1%. You get a certain level of trust, but then you gotta earn the rest. Exactly. And how do you earn it?

1:26:35You earn it by doing what you say you're gonna do in a consistent basis. And eventually, if you can get to that 100 % mark or get close to that, again, it's not exact, but you begin to have more of a trust but verify relationship with that person as opposed to verify it and verify. Does everybody have a little icon on their office door with how much their battery is charged? Although that'd be, that would be amazing. I think Ray Dalio talks about a little bit of that in principles of what they've done at Bridgewater, where you effectively have a trustworthiness score. So he's really actually done it like, like he's, he's, you know, objectively quantified it.

1:27:11But the opposite is also true. And, you know, if you don't do what you're saying you're going to do on a consistent basis, then eventually your trust battery goes down and down. And then eventually like an old cell phone battery, it's impossible to recharge. And that's what I think you have to say goodbye. Mm-hmm. I want to talk about the storytelling piece here. I feel like story is everything. You're a very good storyteller. You are like the public-facing persona of Shopify. You are Shopify when you go and you do interviews and you're on television, et cetera. And that role really is vital. I feel like it's underestimated, like the power of a story well told.

1:27:49And I was at an event recently a couple of weeks ago And I saw a presentation, a really compelling presentation by two guys who are former Chiat Day executives who created this agency called Founder, FNDR. They're here in LA. And it was a whole presentation on story and how critical story is in terms of understanding the mission that your company is on and then effectively communicating that mission to the public, to the investors, to the market, etc. They deconstructed the whole thing. And these are guys who worked with Steve Jobs intimately. They worked with Brian Chesky at Airbnb. They worked with Evan Spiegel at Snap.

1:28:34Like, they're high-level dudes, right? And the way they broke it down, like you've got to understand your story from top to bottom, but from bottom up. And like there's a whole like science and art to drilling down on exactly how you articulate what you're doing that brings clarity to the people who have signed up for this mission and the people who are running it. It is from that which all these decisions get made when you say yes, when you say no. Like all of that stems from truly, you know, understanding this concrete story, much like when you're creating a synopsis for a movie, like there's an efficiency to it.

1:29:11How few words can you use? How do you get to the absolute essence of what it is that you're doing and what you're trying to achieve? In my view, my perspective, the best companies don't just have great product. They also have a great story around that product. And I think we are fortunate because the story around, I think our product is truly world class, but the story around it is all about. success, your own version of success. It's about opportunity. It's about democratizing your thing, uh, distributing something that really matters to you. But I also think it is easier to be, to tell a good story.

1:29:46If you have tenure, if you have longevity, if you really believe in this thing, um, many years ago, I met a, um, I'm a very well-known, very senior executive is now in his 80s. And he'd worked at something like eight of the largest, 50 largest companies in America. And I asked him about the different products and what compelled him to go work at this company versus that company. And he's like, it was all just widgets to me. And he wasn't saying that in a pejorative way. He wasn't saying that in a pokey way of like that company. It was all widgets to me. And he's like, I use the same tactics and the same strategy at company A as I at a company H.

1:30:25And I said, that sucks. It sucks. He's like, I made a fortune of mine. I was like, that is the opposite of what I'm trying to cultivate both from Shopify, but also in my own life. That I think when the company and the product and the mission is more, is deeply personal to you, you tell a better story, you work harder, you build better products, you have more empathy for the people using it. I think the days of company leaders and business leaders selling widgets is over. And, you know, the best example of that is Elon. I mean, Elon, say what you want about certain proclivities he has, but who could run Tesla or SpaceX better than him?

1:31:02He just, he lives this stuff. He dreams about this stuff. And I think for a long time, there was this really, really dangerous version of business evolution where at some point the founders or the early people are swapped out for professional managers. In some cases it works great. I think - But you hear it all the time. You hear it all the time, private equity comes in or whatever, they replace the founder. I'm gonna put in McKinsey, BCG. Yeah, like we're gonna put in operators, these people, this guy, was it Pepsi or whatever, Coca-Cola, I mean, Nike's going through the right now, right? As we speak, they're bringing someone - It's a reckoning.

1:31:36That's right, it's a reckoning. And the person that is going in - Because the vision exited. Right, exactly. And, you know, without that, like the entire mission capsizes. So even if you have the greatest infrastructure, they do. Even if you have the greatest operational excellence, and they do. If you lose the soul, you lose the story, I don't think you can build multi-generational companies that are lasting. So I think story is important. I think it's always been important. But it does feel more authentic now when you have someone telling the story of a company who like who really like who bleeds green in our case or who bleeds whatever Nike the swoosh in Nike's case.

1:32:14And it'll be fascinating because I think the person that just became CEO had been there for like 30 years or something. Right. Started as an intern. Yeah. And worked his way up into this role. I mean, it's kind of an. Which is interesting. Very interesting. Yeah. Because usually that person comes from the outside. That's right. Well, you know, the previous CEO of Nike was from the outside and came from consulting. And now the new one was an intern who sort of worked his way up over 30 years and now became CEO. Like, it's just an amazing, I mean, it feels very Phil Knight, Shoe Dog-esque. But here's the button on this whole thing.

1:32:42You guys work with On, right? Yeah, here we go. They're our favorite brand partner. Talk about Visionary, you know, like they're truly innovating the space. It's super exciting to be affiliated with them. They're an amazing company. Amazing company. But so, you know, when I hear the On founders, the three of them speak about On, they don't, it doesn't feel like they're speaking about widgets. It feels like they're speaking about their children. And you can say, well, is that healthy? Is that good? I think it is. I think when you are bought as a consumer, whether it's B2B software or it's whatever you're purchasing or it's pens, when you know that the person creating it, the person in charge of this thing cares so much about this thing, it changes the dynamic of transaction.

1:33:26It goes back to that. I'm not just giving you money for this pen. I'm voting with my wallet for these types of this craftsmanship to exist. It's that, you know, back to Steve Jobs talking about the, um, what was it? The carpenter who cared about the back of the, uh, of the bookshelf as much to the front. A professional manager, some may, there's some really good person may care about the back of the bookshelf, but the founder definitely cares about the back of the bookshelf. They care about the commons. They care about the way it feels. They care about the delight, the little je ne sais quoi of the whole thing.

1:33:59And it's the reason why I wear James Purse t-shirts. It's the reason why I like on running shoes. Because the people that are responsible for design and the actual production of it, both in on and with James Purse, it's the founders. And in both cases, just to say the thing, they don't have to work anymore. A lot of these people don't have to work anymore. but they still choose to do so because it's their life's work. And I think that is the best part about brands and businesses in 2024. It doesn't feel transactional anymore as the way it does. It feels more personal, more intimate in the best way possible.

1:34:38And that intimacy can be maintained at the onds who are growing at astronomical rates all the way down to the creator economy, right? You've built these tools that now allow so many digital creators to connect with their audience by dint of like, you know, really authentic offerings that they care about. Like I saw that you just, I think it was today, maybe it was yesterday or the day. Yeah, I think it was today. You posted about Tom Holland, who just announced the launch of Bureau, his non-alcoholic drink. Which I've tried, it's delicious. It's good. He was here a couple months ago and we recorded a podcast to help him tell that whole story.

1:35:17That one's going up this weekend because now it's public. But we were, yeah, he was here a while ago. It's up, it's up, it's up. Doing, yeah. So two years sober, part of his journey was - And it's authentically who he is, right? Like this is an outgrowth of his own kind of, you know, personal development in this space. And, you know, going alcohol-free changed his life. Now he wants to be able to offer that to the millions of people who, you know, love what he does and care about who he is. And now he's able to connect those dots. Speaking about the creator economy, just for a moment, One thing that I think is fascinating is that I spent some time in the last couple of days with the person that was running Feastables.

1:35:55His name is Reed for Jimmy. For Mr. Beast. For Mr. Beast. They created Feastables. And Reed was running it. Now there's a new CEO. But Reed sort of helped Jimmy create it and they did it together. And they couldn't find a CEO initially. So Reed took the job. And we were talking about Feastables. And in his office right behind his desk, he has the original Feastables. And we were just sort of joking about Hershey's. and we were like looking up the Hershey's market cap. I think Hershey's is like a$30 million, $30 billion market cap. And we were sort of laughing at one day Confucius ever buy Hershey's.

1:36:24And at some point the conversation sort of got to Jimmy, to Mr. Beast. And I was like, tell me about like his understanding of this industry in chocolate. And Reed's like - It's deep, yeah. There's no one on the planet that knows more about chocolate right now than Jimmy does. That Jimmy knows so much about like the ratios of ingredients and forget the marketing, because Mr. B's is a genius marketer, but the actual manufacturing of this particular chocolate bar, so it has certain ingredients that he really wants to have in it. And then we talked about Beast Burger that he put out there and the quality, Beast Burger was sort of this like ghost kitchen type product where on Uber Eats, you can order a Beast Burger in like, I don't know, 75 cities in America.

1:37:08But the quality of it, because it was distributed and because they were relying on third parties to actually make them, there was inconsistencies between a Beesburg or in LA versus Milwaukee. They shut it down. That's a big business to shut down. Like go back 20 years, talk to some, you know, professional corporate business person. Never in a million years, they've shut down the business, but they did because it wasn't the level of care, the level of quality that they demand from their products. That is very different than the days of, I was a kid at the time, but I've heard stories about like, you know, Brad Pitt launching a toothpaste company at some point in the eighties, apparently.

1:37:50And I don't know who we did a collaboration with, but it was like, basically it was the Brad Pitt, like putting his like logo, his face on some product. That to me was promotional products where, you know, you went to a concert and it was a great concert and you went to the merch booth and like, you got this like shitty t-shirt on the back of all the tour dates. Now you go to the, like a Drake concert and you have like an OVO, which says brand and a Canada goose collaboration you can buy. Or, you know, Fenty with Rihanna, or I was with the sacred people, which is Beyonce's company, um, a cosmetics company, which is on Shopify.

1:38:28These people that are building these brands that are celebrities or content creators, this is not promotional product. These people really, really care. Skims is another good example. Kylie Cosmetics. There's so many of them that are so authentically connected to Tom Holland, to their story, their care. Tom Holland did not just go to some random brewery and try something and say - No, no, no. He spent a lot of time on it. The packaging is spectacular. So this idea that if you think about like, you know, where business comes from, usually you build a product first and then you go and build an audience.

1:39:04And what is happening right now in sort of creator entrepreneurship land, which I love, is that these are people that have audiences first and they're thinking about the things that they love, that their audience might love and they're building products after they already have an audience. And that is almost swapping of like the sequence of events of how business is built has been swapped. But these are not promotional products. These are not, you know, like one-offs that will be gone in a year from now. These companies have staying power and it's really exciting to see that. They also understand that if the offering isn't authentic to who they are, it's not gonna work, right?

1:39:38These are people who have built their audiences over time and understand what these people want and audiences can be very unforgiving, right? Like a misstep and they'll let you know. So they're already so finely attuned to that. And to your point about Jimmy and like pulling the burger line off, that speaks to transparency also, right? Like you can't get away with trying to, you know, put something out there that isn't real or is slapshot, right? Like that will get rooted out. And in business shit happens, but now like there's almost an expectation that you're gonna tell the customers like, hey, look, this went wrong or we made this mistake.

1:40:19And I think people are very forgiving if they feel like there's integrity and honesty in that exchange. Yeah, I mean, the same way that you like right now you have sort of this go direct model of transactions where, you know, there's no intermediary, you as a brand sell direct to the consumer, I think your communications also have to go direct. I think that for earnings calls now, I mean, I do the CNBC thing, but then I post a video directly on Instagram and on X of me talking to my phone saying, all right, everyone want to tell you about how we did in the quarter. Here's about highlights. Here's what I'm excited about.

1:40:50Even the fact that like corporate earnings are being done in that way, I think it's much better. I think it's more authentic. But if you do something wrong, you also have to. Yeah. I mean, you're a publicly a traded company, you gotta be pretty judicious in what you say and don't say. I know like the other day you were taking Canadian businesses to task saying they need to be more aggressive. And there was like a 4 % jump in your stock as a result of that, like talking about the power of story. Right, like what you say to the media has an impact that reverberates, you know, well across like what you might think or whatever.

1:41:24Like there's real ramifications of that. But it also means even for your show, Rich, with your podcast, you don't have to ask permission to anyone. The rich role of 10 years ago had to ask permission. You would have had to have a distribution channel that likely was owned by not you. This idea that you can actually put out the content you want with the guests you want, with the conversations you want, you can edit the way you want. I mean, in many ways, I think this whole direct thing is actually making more all of us more entrepreneurial. Yeah, I never thought I would be an entrepreneur. I still don't even, that feels weird to say that, but I guess, you know, I'm running a business.

1:42:01You're a great entrepreneur. It's amazing. Yeah. I've always been the law school safety kind of security guy. This was born out of a very different thing. It came later in life. But to your point - It's authentic and it's yours. But the tools are available. That's the thing that removes the middleman and allows you to do things without the capital infusion and all those other things that were barriers previously. The metaphor that I find fascinating is this mic we're using right here is an SM7B. Yeah, very famous microphone. For a very long time. And this is, it's unchanged for decades. It's one of the only piece of technology that's been unchanged, but there is something different.

1:42:36People like you, like a content creator, a podcaster didn't have their own Shure SM7Bs 10 years ago. You used to go to studios to rent Shure SM7Bs. I have Shure SM7, I have it at my home office. This is like at my desk, when I go on Skype or Zoom or Google Meet, I'm using a Shure SM7B. In many ways, that to me is like a proxy for what is happening here. That like we've literally taken the tools that weren't accessible to us and we've brought them in front of us and we're putting out better content, building better products, building bigger businesses because like the Shure, the SM7Bs now belong to us.

1:43:12And that's the entrepreneurial, that's the technology change that has happened. I wanna switch gears a little bit and talk about mental health. You mentioned issues with anxiety over the years. You turned 40, Masogi, 2 ,9029. You're thinking about - I'm following your footsteps. I'm just reading. Your own personal, except you didn't have to go through some kind of crisis and for it. Like you just volunteered for it, like God bless you. But mental health is something that you talk about a lot. Why have you decided to speak about this publicly? And what is it that you want people to understand about the importance of mental health in the context of business or entrepreneurship?

1:43:51When I was in grade school, a teacher of mine, I think it was in sixth or seventh grade, said to me that people that have depression often look backwards and people that have anxiety often look forwards. And that was the quote. It's a very simple quote. But are you stuck in the past or are you stuck in the future? I'm stuck in the future. I'm always in the future. But when I heard that particular teacher say that to me, I was like, that's it. I have anxiety. It was this thing that I didn't know that I had, but I learned about when I was a kid. I was like, I'm constantly thinking about what is next.

1:44:21And so I just kind of had that in my mind. It was sort of a bookmark in my brain for a while. And then at a certain point, I'm like, I don't have to be stuck in the future. Like, I get to decide this on my own. And then this is only something I've sort of discovered in the last couple of years, five years or so. I was like, I don't have to be stuck. Like, anxiety is me projecting something that may not exist. But I get to choose this sort of stuff. And I began to sort of learn about mindfulness and meditation practices and all those things have been really, really helpful for me. And I never really talked about it.

1:44:53I always thought that it was a very personal, very vulnerable, just not my style. Like same way I told you, you know, I, when I cried at the end of, of Everest, I was like, why am I crying like this? But as I began to tell more people, Hey, and this is in a very personal, you know, very one-on-one sitting, have anxiety. here's what's working for me. I find the easiest way, you know, for me to just tone it down is to do very simple box breathing and sort of activates my parasympathetic nervous system. And here's a really good blog post on it, or here's a good podcast episode on it. The more that I kind of shared that, the more people sort of got closer to me, people that I weren't necessarily close with began to, we just had a different relationship after the disclosure of my anxiety.

1:45:36And so I began to do it again. I was like, okay, well, um, you know, sometimes I wake up in the middle of the night and like my mind is racing like a lot of people have. And someone said to me, like that teacher, this is more recently said, when you wake up in the middle of the night, often what happens is your amygdala, your fight or flight response, part of your brain is activated, but your free prefrontal cortex is asleep. So there's no rationality happening. And so for a while, when I wake up in the middle of the night, thinking about something that is never going to happen, I would just remind myself, I was like, yeah, remember, you're not being rational right now.

1:46:06So go back to sleep. And in the morning, prefrontal, you know, Mr. and Ms. Prefrontal Cortex will be, will be awake. And we can have a rational discussion in my own mind about whether or not this is a thing or this is totally ridiculous. And again, I began to share, hey, I heard this really cool thing about prefrontal cortex and amygdala is being asleep when I'm, when, when you wake up in the middle of the night. And people are like, like people that were in their 60s and 70s and 80s who were really thoughtful about this stuff would tell me like, huh, I didn't think about it. I never thought about it in that way.

1:46:35and so I just made a decision a couple years ago to start sharing more about this sort of journey that I do have anxiety I my self-identity is not based on anxiety but when we get into a conversation around mental health I'll say you know I've had anxiety for quite some time and here's what helps me and and here's what I've discovered here a couple things that I think about and I guess one of the better parts of getting older is that I just feel less scared to just say the thing about here's how I'm feeling, or here's the thing that's bothering me right now, or here's the insecurity at this current moment.

1:47:09And so that's the reason why I've continued to share it. And I, I find it to be, um, I've, I've now been able to build sort of this toolbox of, of, of tactics. Um, I mentioned to you earlier that, you know, I'm part of this longevity league of these people that really care about longevity. And, um, we do this longevity weekend, uh, every year in Muskoka and it happened a couple of weeks ago. And I actually brought my, my mindfulness coach with me and we did a presentation and we talked about this. It's, I know it sounds super cheesy, but - Sure you don't live in LA? I don't live in LA, I live in Canada.

1:47:39It's a very un-Canadian thing. I know there are a bunch of LA people in this group. But I know some of those Muskoka folks. They're very LA-esque. Yeah. But I brought my coach and I actually, I explained what this toolbox was that, you know, if I'm about to do something and I'm feeling really anxious and I only have like three minutes, here's a tool that I'll use. It'll probably be a box breathing. and if I actually have a little more time, I may do like a full eight minute or 12 minute sit and here's what it would look like and I began to unpack this box and it was remarkable because some of the people in this longevity league are like some of the most, you know, unbelievable people in the world, famous astronauts and artists and business titans, people that are way, way more successful than I am and they came up to me, these like, some of these guys are like tough guys, like Harley, that was really great, I'm gonna use some of that stuff.

1:48:25I was like, dude, you're 75 years old, Like, like I look up to you in every aspect of your life. Like, there's no way I'm just teaching you that. And it's because I think there was this generation of, in particular, business leaders who simply locked that aspect of their life away in a box. And they didn't talk about it with their spouse or their kids or their business partners. It was a sign of weakness. And I think for whatever reason, something has changed that it's now okay to talk about those things and invite people in to participate in what your issues are because they probably have similar issues.

1:48:59So many things I want to tease out of that. I mean, first of all, like obviously vulnerability is connective tissue. It makes you feel closer to people and people feel closer to you. It sounds like you've learned that and realize and appreciate that. But to your point about this instinct or compulsion to compartmentalize whatever our dysfunction is and say, well, that's our weakness and I'm going to put it over here. I think conversely, and perhaps even more common, especially with high performers, the relationship with that dysfunction is not that it is a weakness, but actually a strength, right?

1:49:36Like your anxiety is what fueled your drive to be relentless or the bond trader who convinces himself that his gambling addiction is actually making him a better trader or the heroin addict who thinks that's why they're able to write great songs or whatever it is. It is those mental health issues that we mistake as superpowers because on some level, if we're being honest, they are fuel for what it is that we're trying to create but it's a short-term unsustainable fuel, right? And you're either gonna crash and burn, you're gonna hit the wall with it and realize you're gonna have to find a different way.

1:50:17Or it sounds like with you, like you were able to kind of recognize that early enough and course correct and find new and healthier strategies. And also, I don't wanna lose that. I don't wanna, I don't wanna, I was sort of worried a little bit about - If you were completely a quantumist, yeah, how are you, are you gonna be able to get up in the morning? And this is the dilemma, right? Correct. So let me share something happened this morning, more than I was planning on sharing, but in the interest of full disclosure, I woke up this morning, I've seen a ton of your podcasts, some of your interviews, but I had not watched Alex that you had, Free Solo.

1:50:52And I think it came out last week. It just came out. Yeah. Okay. I had not watched it. And I was like, I need to watch this right away. Now it's quite a long podcast. And I woke up early, like 3.30 in the morning, which is a little different. I'm still on ESC time zone, but I woke up and I went for a run and then a walk and, and, but I listened to the entire episode. Partially I was interested in, I think he's super fascinating guy, but also I, I didn't feel right about coming on your show today with having heard your most recent podcast, because I think that's like, you are the best at what you do.

1:51:26And the, the, this incredible opportunity for me to come on your show is an honor for me. And I take those things very seriously. That instinct to listen to your most recent episode before I showed up here today may have been partially driven and sourced through anxiety. I don't really care. It did something really great for me. I now, I believe I had, when I walked in the door today, the most current version of how you were seeing the world because, and again, ironically, it may have been filmed six months ago. I didn't know that, but I felt that I owed it to myself and to you, but, but mostly to myself to know what is Rich's most current version of the world, his, his, his most current perspectives on things.

1:52:09And there was no way that I was going to walk in here today without having listened to that. That matters. And that's where I think anxiety is a fucking superpower. But that choice can be generated from something else other than anxiety. Could be, but for me it's anxiety. And so I'm not going to say like, I wish I wouldn't, I wish I would have slept in longer. No, that's, that happened when I go on, you know, Kramer, Squatbox or Mad Money. And I know he's going to ask me some, you know, random metric about, you know, I don't know, contribution margin of some particular of our business. The reason I know it is because of anxiety.

1:52:44I don't think that's necessarily a bad thing. I think it could, like, it's not getting the better of me. Like I wasn't going to wake up at midnight or something and not sleep last night because I wanted to listen to Alex's episode. I woke up at a time where I probably would have woken up around that time anyway, but I focus on it because I thought it was very important. I wish it wasn't only anxiety-based, but if that's the reason that I'm able to be good at the things that I do or better things I do that I wouldn't otherwise, I'll take it. Yeah, I suppose if it's working for you and not against you on some level, but understanding where you are on that spectrum, because if you're so anxious about what's happening tomorrow that you can't be present with your family or, you know, that kind of stuff.

1:53:27So there is, again, there is a threshold to this, which is that, is it actually making my life better or worse? And for the most part, I've been able to channel in a way that I think it makes my life better. But there are times where I will say to Lindsay, I'll say to my wife, like, I know we're at dinner right now. I don't want to be that husband who's like staring at his phone the whole time, but I'm dealing with something right now, like on the business, I need to take care of this. And Lindsay has said to me, like, she much prefers me to say that than to pretend like I'm present with her when I'm not.

1:53:57And so I'll say, give me 10 minutes, time me if you want, I'm going to go outside the restaurant and, and, and Lindsay, if you want to leave, like, you don't want to sit here by yourself, no problem. But I need 10 minutes. And Lindsay's like, no problem, take 10 minutes. But when you come back here, it's, we're on date night, right? And I was like, yeah, we are. And I'll come back and I'll turn my phone off and I'll put it away. so even that type of thing 24 months ago I would not have done that I would have pretended that I can do it all so what changed uh is it this mystical 40 me I don't know 40 yeah no it's not mystical I think 40 is just it's just a bookmark in your life and it's like okay how much more time do I have when my kids are young in the early days of having kids my kids would come into our bedroom to our bed every night and I used to like wake up and be like Like, I just want a good night's sleep.

1:54:45And now they're coming to our bed less and less. And every now and then I kind of miss them coming to our bed at night. You know, snuggling up and waking up with our two daughters in the bed. I don't know, maybe it's just getting older. Maybe it's meeting more people who explain to me, people that I thought I admire, back to that vertical mentors that I really admire in one particular area. And when I say to them, you know, what's something that I don't know that I should know about your life? And they'll say, I didn't do date nights. I wish I did. And so I think, yeah, having more of those people in my life, plus just getting older, dropping a little bit of the ego, it's a very helpful mechanism.

1:55:24Yeah, you're at where you're at. You've been there for a while. So how can you take this intense intentionality that you have devoted to your business, to the other areas of your life that are important, right? Because listen, you've scaled a huge mountain. There's always more mountains to climb, but what is that really going to do for you? And I want to enjoy this mountain for a moment, right? The flip side of the anxiety sort of as superpower is that there's also this consistent perpetual, um, not dissatisfaction, but like neutral satisfaction that like, okay, I'm here. What's next. And that goes back to the topic of even enough.

1:56:00Am I doing enough? Do I have enough? Do I feel like I am enough? I haven't figured it out yet, but at least now I have language for it. And I think like naming things back to the sort of founder mode thing, I think this idea of having language for this to be like, oh, this is me just playing this enough game. Like, I'll never have enough. Like, you know, a lot of entrepreneurs that I've met that are very successful, they talk about their magic number of how much money they've made. Yeah, but they never, when they get it, they never retire. Literally zero. I have great mentors. Like, I've had over my life dozens of incredible people.

1:56:29Not a single one of them has said, I hit my magic number and I was good. So, like, having a magic number is totally stupid. it. Because if someone that, you know, I interviewed, I have this podcast called Big Shot, where I created an archive of Jewish entrepreneurs. And most of them are quite, you know, in their 70s, 80s and 90s. I interviewed Izzy Sharpe, who created the Four Seasons recently. And I asked him about when did he know that he made it? I mean, he created the Four Seasons Hotel. So the Four Seasons is amazing for two reasons. One, it's, I think, one of the nicest hotels on the planet.

1:56:59But two, the business model is very unique because the real estate is owned privately, but the services inside the actual staff is owned by the Four Seasons. So he not only created like the Four Seasons hotel chain, but he also created a brand new business model. A novel model. A very novel model. And Four Seasons is incredibly successful everywhere they are. And I asked Izzy, you know, when did you know you made it? Izzy's 93 years old. And he said, I still don't know. And in that moment, I felt two things. One, wow, like what an amazing like thing to say, like he's Izzy Sharp, um, storied entrepreneur.

1:57:38I, and I put four seasons in the same class as like Apple from a brand perspective. Um, but also like, I'm not sure I want to say that when I'm 93. It's sort of sad. Like what is making it mean and what is driving the desire to quote unquote quote, make it however you define that, right? And I think if you're mission-based and that mission is tied to serving people and making the world a better place and that mission has no end, like there will never be a destination where all the work is complete. There's something beautiful and laudable about that to devote your time and your energy and your life to something like that.

1:58:18But if making it or just climbing this endless mountain is about filling this hole in your spirit because you're detached from anything more meaningful in your life. Like you're gonna end up alone and sad, right? So what are you chasing? And on some level, it's back to story. Like, what are you doing? Like, what is this thing that you're spending all your time, what is it for, right? What are you chasing? And getting really clear on that. On some level, like we're all victims of our ego living in the material world, like chasing shiny things and running around like, you know, with our heads cut off.

1:58:58But on some level, like I clearly, you know, what comes across with you is you're on a mission and that mission is very important. And you have a lot of clarity around what that means. Where's the caution around not getting caught in that trap? That's right. And there's this fine tension because the people that are most successful sort of in my view of that, a lot of them are hard driving. It's never enough type people. So the benefit that I have is I'm, you know, 50 years younger than some of these people that I'm interviewing for Big Shot. And I can learn from their successes, but I could also learn from their mistakes.

1:59:33And I like, there's this great sort of, there's a guy named Alexander Chalmers who wrote a book in, I think it was 1700s, Scottish guy. And it was about the secret to life, secret to happiness. It was very simple. I remember this, like, I don't have any tattoos, but this would probably be the tattoo that I would get, which is like someone to love, something to do and something to look forward to. And whenever I'm sort of struggling, I always sort of go back to the things like someone to love, like I'm, I'm deeply and madly in love with my wife and my, and my children. And the thing that I do 90 % of my time is, is help build this great company that is deeply personal to me.

2:00:09Check. And someone to look forward to, I always try to find something that like I've been on the road for the last couple of weeks and I'm going home, um, uh, on Friday, uh, back to Canada. And I'm just like, I know exactly like what I want to do Friday night. Like I, there's a particular bottle of wine that I want to drink with my wife in a particular room in our house. And we're going to watch a particular movie and I'm really looking forward to that. It's not like some major trip or some big event. It's just, I'm really looking forward to Friday night going home and having this, this evening with Lindsay and So I just kind of keep going back to that like it's so simple.

2:00:42someone to do, someone to love and someone to look forward to. Like, it's just, if you have that, you kind of have it all. I believe you. I believe what you just said, but, uh, I also think this, are you ready for this? Let's go. I bet you're terrible at vacations. Terrible vacations. Yeah. Terrible vacations. You can't turn it off. Can you? No, but on vacations, what I realized is that I'm actually really good at like one week vacations. I'm really about a two-week vacations. So what does that mean? It means that I really love, like my weekends are really fun. I really enjoy my weekends. I work a little bit in the morning, Saturday morning, and Sunday morning, but generally I try not to do any deep work on the weekends.

2:01:21I have two young kids. I want to spend time with them. So my weekends are sort of like friends of mine want to take larger trips, three-week weekends. And I was like, and I cannot do that right now. I don't think I have the, I don't, I don't. But let's say just as a thought experiment, let's say you could trust and have confidence that whatever obligations that you're responsible for are being taken care of. Let's assume that everything is fine at Shopify and you have these three weeks and you've got buddies, they wanna ride mountain bikes across Vietnam or whatever, right? You have an opportunity to do this.

2:01:59Do you feel the anxiety? Yes. Right, so the question then becomes like, Like, what's behind that? Like, what is the discomfort with sitting still with yourself, right? And I think that's the teacher, right? If you can go, I'm saying this as somebody who has the same, you know, I have the same thing. How are you on vacation? A lot better, but I'm older, you know, I'm older than you, but yeah, like, if it's like, oh, I need to be busy. I need to be doing things all the time. I don't know what to do with myself if I'm not. Like, there's something there. Like one thing that works. to examine. My favorite beach in the world is Turks and Caicos.

2:02:36I just think it's a beautiful beach. It's really lovely. I get together with my family every year. And when I'm there, I try to like, you know, first couple of days I'll sit around the beach and play and then I'll go take a kiteboarding lesson or I'll go take my daughter kayaking. And so I'm finding things now that like I want to be more present. And so I now realize actually I'm more of an activity kind of guy. I can't just sit on a beach endlessly and listen to like music. I'll go for a long walk with my wife and we'll have a great conversation or I'll run on the beach with myself and listen to a podcast.

2:03:06But I'm beginning to, rather than pretend, and that's, I think what I used to do. I think my, the old version pretended to be good at vacation. I'm not. Okay. So let's figure out a way to like, at least for now to create vacations where I can be present and also be self-aware to say like, what, like ask myself this questions. Why can't, why can't I just sit on the beach? What is preventing that from happening. And I don't have that answer yet, but I'm for the first time in my life, I'm asking those questions. I never did that. Like I would never ask those questions before. So if Lindsay, your wife is sitting across from me right now and I asked her like, what is Harley's major malfunction?

2:03:44Or like, what is the thing that comes up in your marriage that that is the biggest challenge for her? She would say I can't sit still. Yeah. And sometimes that affects her. Yeah. That's what I thought. Yeah. It's that same thing. Like, well, that's, that's the same energy that makes me successful. You don't get one with the other. You can't have it both ways, right? I don't know. I'd like to try. Yeah, so I'm not saying I have an answer to that, but I just think it's interesting and worth investigating. What has happened to you that has actually created the most amount of self-tolerance to allow you to do a vacation?

2:04:16Has there been something that, other than just sort of getting older? Well, all of these things for me are the result of doing it the wrong way for so long that it creates sufficient amount of chaos and pain that I'm forced to do something different. I took a month off for the first time right before the pandemic because I was teetering on burnout, and I was incredibly just like sort of uncomfortable in that. And now I do it proactively every year as like a prophylactic, like it's built into my year. And every year that I do it, I untether a little bit more. Like, at first I was like, I was still checking my email all the time or like the last time that I did it, which was almost a year ago, like I didn't look at my email once and like everything was, it was great, you know?

2:04:57So I'm learning, like I'm not perfect at this. And I mean, this is a very privileged, you know, thing, right? Like I recognize that, but the point being like finding a way to have a relationship with yourself outside of the context of what you do so that your identity is not so, you know, completely embedded in, you know, like Shopify president, right? there is a harley outside of that there is worthy of of honoring there is this um back to law school friends i met with a law school uh classmate of mine a couple years ago probably five years ago and he was just about to become partner at a big law firm like a big white shoot law firm with all the accoutrements and all things that comes with it and um uh we were talking about something and he's like oh yeah well sunday night i was like sunday night he's like yeah well that's you know the worst time of the week i was like what do you mean he's like i hate sunday nights I was like, well, why is like, because Monday's coming the next day.

2:05:54And I'm like, huh? Anyways, let it go. I didn't think much about it. I called him back a couple of weeks later. This isn't probably five years old now, um, uh, five years ago at this point. And I called him back. I was like, you know, thinking about your comment about Sunday nights. And I, I know there's like these sort of memes around Sunday scaries, but part of the reason that I don't, I don't know if I don't love vacations or don't need vacations or struggle with it a little bit is because like my Sunday night feels like my, my Friday nights. That's a gift though. And I realize that's not most people's experiences.

2:06:24And I acknowledge that. I actually acknowledge the fact that that is incredible privilege that my Saturday morning, that feeling Saturday morning, I feel like that Monday mornings, you know, too, not all the time. Sometimes I can have a bad day or something like that, but generally that's how I feel. And I think that privilege comes with a great amount of responsibility. And I feel that responsibility. Now, the key for me is not to mistake responsibility with avoidance of like some issue I'm not dealing with. I'm not at that stage of evolution. I'll come back in five years. I'll report back of how I'm doing.

2:06:53Well, before we kind of close this down, maybe we can end this with a few thoughts around what you've learned in your journey of entrepreneurship that are relevant to, like, I don't run an entrepreneur podcast. Like, you know, this is not a business podcast. Most people listening to this, maybe, you know, a bunch of them have side hustles or they're Shopify clients, but most of them probably aren't entrepreneurs. So how is this relevant to the average everyday person who's tuning in, looking for a little insight on how to level up their life a little bit? We talked a little bit about this idea of like, you know, the thing you already do is like that you do personally is could be the thing you also do professionally.

2:07:33And so I think we've covered that this idea that like if you make the greatest minestrone soup for your family, like imagine you started a minestrone soup company. The example I'm going to give you, though, is fascinating. So I mentioned this sort of tea company. So my best friend, David, who's like the king of tea, not just in North America, on a global scale, he has built the largest tea company of the last couple of decades. He left David's Tea after the IPO. Since 2016, he left a year after the IPO. And as he was thinking about what he wanted to do next, remember, this is like the tea guy.

2:08:06He constantly was bringing me tea. He was constantly talking about tea, but he himself didn't actually realize that his next thing should also be tea-related. The reason I bring up this particular story but David is because if the king of tea, like his name on Instagram is literally Tea Maverick. It's all he talks about. If he himself is somewhat blind to the thing that's in front of him, that I had to give him a kick in the butt to say, dude, you gotta start another tea company. This is like your thing. It tells me that so many people have something in front of them that they simply are not acknowledging that could be their thing.

2:08:38And so the first thing I'll say to you is for those listening that wanna start a business, likely the business that you're going to start that you will be most successful at is right in front of you. And it may be literally staring you in the face right now on your desk, you know, on your walk right now. So one, like look around, figure out what that is. The second thing is this imposter syndrome of entrepreneurship, it's only in your own head. Almost every merchant on Shopify that has started on the platform at their mom's kitchen table that has made a billion dollars still says that they're still trying to figure it out.

2:09:14that there is this assumption or presumption, I should say, that at a certain level of success, you haven't figured out. One of the greatest aha moments I've had through these interviews through Big Shot that has been so comforting to me is even the most successful entrepreneurs in the planet that I've met are still trying to figure it out. They still don't know exactly what they're doing, but they've gotten better at being okay with that. That true confidence isn't actually knowing what to do. it's knowing that whatever comes your way, you'll be able to figure it out. Second thing, the third thing is back to the cost of failure.

2:09:48Like it is scary to start a business. It is very scary to put yourself out there. It is very scary to fail. The cool part is the safety net right now for most people listening most of the time, especially like, you know, in this part of the world is you start something that doesn't work. And so you pivot and try something different. And a lot of the companies that you admire, it didn't just start with, It didn't start with Shopify. It was first a snowboard shop. And it didn't start with Slack. It was a gaming company. And it didn't start with like, you know, Supreme started as like a single like deck, like a skateboard deck.

2:10:25And I think that there is this thing we do to ourselves that I'm still doing at this stage, but I can, you know, do as I say, not as I do. You just get over that and try and put it out there and see what happens. And then in terms of your concern about how do I compete with those incumbents that are out there, those incumbents cannot do what you can do. Those incumbents cannot write personal letters to the first 10 customers because they have to do everything that scales. And they can't learn the birthdays of the people that are buying from them so they can send a little email and say, I think it's your birthday today, happy birthday.

2:10:55If you were thinking of starting a business, those are the things that I would think about today. And I'd love to help in any way I can. I pray at the altar of entrepreneurship. Shopify prays the altar of entrepreneurship. And we want more of those to exist in the world. Yeah, that was awesome, man. Thank you. Thank you. I really appreciate you coming here to share today. Thanks for having me on. It's great honor. I love the mission that you're on. You know, the democratization of all of this, like making these tools accessible for just everyday average folks to create something unique and special.

2:11:29I think it's awesome, man. Yeah, and despite you not thinking you're an entrepreneur, you're an incredible entrepreneur, and this is really fun. Yeah, thanks, man. We did it. How do you feel? You feel good? It's great. Yeah, I can do this all. I can just all day. Keep going. Well, come on back. I'd love to. Yeah. With less anxiety. Yeah. Good.

2:11:59That's it for today. Thank you for listening. I truly hope you enjoyed the conversation. To learn more about today's guest, including links and resources related to everything discussed today, visit the episode page at richroll.com where you can find the entire podcast archive, my books, Finding Ultra, Voicing Change and The Plant Power Way, as well as the Plant Power Meal Planner at meals.richroll.com. If you'd like to support the podcast, the easiest and most impactful thing you can do is to subscribe to the show on Apple Podcasts, on Spotify and on YouTube and leave a review and or comment.

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