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

Harley Finkelstein is Shopify’s President and an entrepreneur who started his first company at 13. This conversation explores the intersection of commerce and personal growth through Harley’s iconoclastic lens. We discuss democratizing entrepreneurship, the role of anxiety as fuel for achievement, and why this might be the most generative moment in history to start a business. Harley challenges my self-perception as an entrepreneur, forcing me to untether from limiting beliefs about what it means to build something meaningful. Sharp, vulnerable, and endlessly optimistic—this exchange offers a fresh take on modern entrepreneurship. Enjoy! Show notes + MORE Watch on YouTube Newsletter Sign-Up Today’s Sponsors: Roka: Unlock 20% OFF your order with code RICHROLL 👉ROKA.com/RICHROLL Aura Frames: Exclusive $35-off Carver Mat 👉AuraFrames.com Use code RICHROLL at checkout to save! Eight Sleep: Use code RICHROLL to get $350 OFF your Pod 4 Ultra 👉eightsleep.com/richroll AG1: New subscribers a FREE $76 gift: Welcome Kit, a bottle of D3K2 AND 5 free travel packs 👉drinkAG1.com/richroll Airbnb: Your home might be worth more than you think. Find out how much 👉airbnb.com/host This episode is brought to you by Better Help: Listeners get 10% off their first month 👉BetterHelp.com/RICHROLL Check out all of the amazing discounts from our Sponsors 👉 richroll.com/sponsors Find out more about Voicing Change Media at voicingchange.media and follow us @voicingchange Learn more about your ad choices. Visit podcastchoices.com/adchoices

Speaker names marked ? are inferred from speaking time and the show’s known hosts — they are not voice-verified.

• 0:00Rich Roll?

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• 1:05Speaker 01

  It is scary to start a business. It is very scary to put yourself out there. It is very scary to fail. The cost of failure in the 50s of entrepreneurship was massive. Today, it's not.

• 1:17Rich Roll?

  Harley Finkelstein is democratizing entrepreneurship for the digital age. As the president of Shopify, Harley has helped transform a small snowboard equipment retailer into a global e-commerce giant that now powers over 10% of all online retail in the United States. But Harley is more than just a tech executive. He's a serial entrepreneur who started his first business at 17. He's a lawyer. He's a dragon on CBC's Next Gen Den, and a champion for mental health awareness in the high-pressure world of startups.

• 1:53Speaker 01

  This imposter syndrome of entrepreneurship, it's only in your own head. 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.

• 2:03Rich Roll?

  Harley embodies the spirit of modern entrepreneurship. He's curious, he's resilient, always innovating.

• 2:10Rich Roll?

  And this is a conversation about all of that. It's about seizing opportunities, embracing challenges, and the transformative power of technology in both business and life.

• 2:20Speaker 01

  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.

• 2:29Rich Roll?

  Do you think that everybody can be an entrepreneur?

• 2:39Rich Roll?

  Great to have you here. So nice to meet you.

• 2:40Speaker 01

  Yeah, you as well.

• 2:41Rich Roll?

  The first thing I wanted to ask you about, I saw this on your Instagram. You recently did the 29029 event, right?

• 2:47Speaker 01

  Crazy.

• 2:47Rich Roll?

  Like five weeks ago or something like that? Which one did you do?

• 2:50Speaker 01

  I did Trommla. I think there's two. There's one in Whistler in Canada. This is the second one in Canada.

• 2:55Rich Roll?

  Are you friends with Mark and Jesse and those guys?

• 2:57Speaker 01

  I'm now friends with Mark. I didn't know them before, but I ended up doing a bunch of the hikes with Mark. And when you're doing something like that, you sort of bond with the people you do it with.

• 3:06Rich Roll?

  You definitely get to know people well.

• 3:07Speaker 01

  I knew the concept. I know you sort of had a bit of a turning point when you turned 40. I kind of had a similar thing, which is I was like, I want to start thinking a little bit more about our family motto in my house with my wife and my kids is, my kids are five and eight, so I'm not sure they really understand the family motto. But my wife and I's family motto is the way you do anything is the way you do everything. And it's just a proxy for intentionality. And I sort of felt like every aspect of my life, especially my work life with Shopify, was very intentional. But I wasn't necessarily sure that my health side of things were as, I was being as intentional. And I heard about the concept of Misoji, this idea that do something every year that I think that, I mean, this is my version. That scares the shit out of you. But also has been the bookmarked the year. And so I turned forward and I want to find something.

• 3:52Speaker 01

  And then I read about this idea of Everesting, which is climbing the equivalent of Mount Everest, 29,000 feet. And they just happen to have one like an hour away from Montreal, where I live. And so I did it. It was awesome.

• 4:04Rich Roll?

  That's cool, man. That adventure is a little sneaky, right? Because on paper, it's like, how bad can it be? Like you hike up with your friends and you take the chairlift down. It sounds actually quite pleasant.

• 4:15Speaker 01

  Yeah, it's nice.

• 4:16Rich Roll?

  And then inch by inch, it starts to, you know, become a thing. Thing, right? And you're like, wow, it's a little bit harder. And what's great about that event is it sounds like you're not coming from like an endurance background, you're not like running marathons and stuff like that. So it feels very doable. And I think it brings in people who haven't done something hard before, because it feels like a nice starting point.

• 4:36Speaker 01

  Yeah.

• 4:37Rich Roll?

  But it's actually quite hard. And what's so cool and fulfilling about not just participating, but getting to know the other, you know, sort of people that are doing it, is seeing those people who've never done anything like this before, but then becoming determined to finish it, you know? And literally, it's like, you're into the second day, and you get to decide whether you're going to go to sleep or not, and for how long. And when those people finish, like, this is way more than doing a 5K or a 10K, or you know, this is very difficult.

• 5:05Speaker 01

  It turns out it's like 50K.

• 5:06Rich Roll?

  Yeah.

• 5:07Speaker 01

  Right?

• 5:07Rich Roll?

  And when they finish, like, it's life changing.

• 5:09Speaker 01

  Yeah.

• 5:10Rich Roll?

  You know, for a lot of them.

• 5:11Speaker 01

  There was a rumor that I heard that you actually finished early, so you did an extra one. Is that true?

• 5:14Rich Roll?

  You did your homework. Yeah. No, I don't, I don't talk about that publicly.

• 5:17Speaker 01

  So you did an extra one?

• 5:18Rich Roll?

  I get a lot of shit for that.

• 5:19Speaker 01

  Which is the most sort of, you know, ambitious, type A thing I've ever heard in my life.

• 5:24Rich Roll?

  That was not the plan. I just was struggling with trying to sleep.

• 5:27Speaker 01

  Yeah.

• 5:27Rich Roll?

  Because when you're doing something hard, it's disruptive to your sleep. And I was just awake. So I was just like, I'm gonna get up and do it. And my buddies were like, oh, you snuck out? And like, you know, that was not the case at all.

• 5:37Speaker 01

  Right, okay.

• 5:38Rich Roll?

  And they're much, much better athletes than I.

• 5:40Speaker 01

  It's a very subtle flex, but I, but I really loved it. I loved it for a few reasons. One is, I love the idea of the training up to it, that because I'd never done a marathon, I'd never done an endurance race, I was scared. And one of the things that 29 does really well is, you do these sort of, these like Zoom calls with coaches. And so I got a chance to meet the coaches, and one of the Zoom calls are like, write down what you're most scared of as it relates to the race. And I only had one thing written down, which, and this is, you know, I'll be vulnerable here. I wrote down, I'm scared of not completing because of being embarrassed.

• 6:14Speaker 01

  And then, and so next call, they're like, take that one thing you're scared of and break it down more. I was like, okay, who am I embarrassed like? And honestly, I did it with a group of guys. We all trained together and it was, I didn't want to fail because I didn't want to be the guy in the group that didn't complete it. That if I'm so intentional with every aspect of my life, I gotta finish this thing. And so actually, our little group text was dead or done. That like, no matter what, come hell or high water, we're completed. What I did not anticipate is the mental exhaustion of being up for 36 hours straight. And you hear these stories about, you know, after hour 26, you're gonna start hallucinating. And I was like, there's no way. I'm gonna be fine. And at hour 26 or so, I took, went

• 6:57Speaker 01

  to go take a 60 minute nap because I just, my brain was mush. You can sort of feel those proverbial demons came out saying, well, you already did 10. I think the 10 was the equivalent of Kilimanjaro. So I'd already climbed the equivalent of Kilimanjaro. Do I really have to do Everest?

• 7:13Rich Roll?

  You start making those deals.

• 7:15Speaker 01

  You start making those deals with yourself, or deals with the devil, as they say. And so I took a 90 minute nap, came back, finished it. It's this wonderful experience that you cross the line with your red hat, with the guys you've been training with. And it was awesome.

• 7:29Rich Roll?

  How many guys did you do it with?

• 7:31Speaker 01

  We were four total. Yeah, me plus three.

• 7:32Rich Roll?

  And in those Zoom calls with the coaches, was one of those coaches Chris Hout?

• 7:36Speaker 01

  Definitely.

• 7:37Rich Roll?

  Yeah. So when I was 40, he was my guy. Like, he's been my coach from day one through all my endurance challenges. Yeah. So Chris now works closely with Jesse on a number of things. But back in the day, when we first started working together, he was purely like an Ironman triathlon coach and an ultra endurance coach. And he's the one who kind of shepherded me through like, everything that I did back, back in the day.

• 8:02Speaker 01

  They're amazing. And the other thing I think was, for me at least, what was remarkable is that it was one of the first times in my life that I really felt like I did not check my phone. I did not check my email. I was like, fully focused on this one specific task. And I try to be a bit of a master multitasker in general in my life. There's just no way to do multiple things when you're doing something really, really difficult. And I would do it again for no other reason than simply to have a singular focus for an extended period of time. And across the finish line, my wife and my daughters were waiting for me and I just like welled up and started to cry. And I don't even know why I was starting to cry. It was hard, but it wasn't that emotional for most of it.

• 8:45Speaker 01

  And I think this idea of doing something that scares you becomes less and less common as you get older. This idea of like comfort zone stuff kind of creeps in and I actually think like what I've learned from it is like this idea of getting really comfortable with being uncomfortable. I'd like that to be my operating model if I can for the next 40 years.

• 9:07Rich Roll?

  Well, Masogi, box checked, yes. I think the interesting kind of ripple in the whole like comfort zone, out of your comfort zone thing, particularly with high performers like yourself, is that being a public person, you're sort of celebrated as somebody who has prevailed in the game of being outside of your comfort zone. And that celebration can actually keep you stuck because what people don't understand is that thing that appears to be so uncomfortable for so many people is your comfort zone. You know what I mean? Like the hard thing that everyone's so scared of that you've spent many years mastering, everybody thinks that you're way outside your comfort zone, but that actually becomes your comfort zone.

• 9:51Rich Roll?

  And then you have to exert a lot more kind of effort to figure out how you're going to step outside of that. And you're so used to being celebrated in this one area that like for you to say, you know, the embarrassment thing, like I get that because you're seen as a successful person, right? So what does it mean if you fail in this other thing? As somebody who also talks a lot about failure and embracing failure and all of that.

• 10:15Speaker 01

  And I don't have to do it. I can just sort of, I can cruise from this point, right? And I don't want to cruise. I actually think that ultimately that sort of family motto of how you do anything is how you do everything is about not cruising. I say it's about intentionality and my wife and I try to put the same thought into like making like a dinner like on a Sunday night for our kids as we do by planning a trip as I do by preparing for an earnings call for a quarter end.

• 10:37Rich Roll?

  It feels like a lot of pressure though, too, especially for little kids. You're inculcating them with that.

• 10:42Speaker 01

  For sure. And not just that, now am I actually focused on... Spending time on perfecting some version of a meal for my children. And that's actually where the balance comes in is that I want to make the best pancakes. But if I spend all my time thinking about the ingredients to the pancakes and less time about sitting with my kids while they enjoy it, I didn't really win this thing. In fact, I lost this thing. But it's tough to sort of turn off this like, whatever the alpha energy is, the type A energy is, and say, this actually, what matters here is like, spending time with my children, not making the greatest pancakes on the planet.

• 11:15Rich Roll?

  And how are you doing with that?

• 11:16Speaker 01

  Not very well.

• 11:16Rich Roll?

  Yeah.

• 11:17Speaker 01

  Not well.

• 11:18Rich Roll?

  I heard you talk about that a little bit with Stephen Bartlett, like your ambition to be a great dad and being honest about where you might have some, you know, room to grow in that area. I don't know when you recorded that, but you know, it wasn't yesterday.

• 11:34Speaker 01

  No, it was a while ago. I think I've made some progress. I think what I have realized is that this idea of mentorship, which is something I know you talk a lot about on your show, I don't think you can carbon copy any one particular mentor. I think you need mentors across different verticals. And I don't necessarily think I've surrounded myself historically with people that were the best parenting mentors in my life. I didn't gravitate to them the way I gravitated towards business mentors, successful people in like, from a commercial perspective. And part of it is that you can quantify business success, money, market cap, size, growth, whatever metric you want to use.

• 12:15Speaker 01

  It's very difficult to figure out who's a really great father and then say, actually, I'd like to learn from that person. Paradoxically, almost, it's way easier for me to find mentors in business than I can find mentors for parenting, even though parenting is probably where I need the most amount of help right now.

• 12:33Rich Roll?

  Interesting. Yeah, I mean. I've had people on this show who will look me in the eye and say, I know I'm a great dad. And I thought the same thing, like, how do you measure that? But there is a knowingness for those individuals because that's where their energy is, right? And for somebody who has a lot of responsibility in the real world, in the business world like you do, for me, it conjures up a conversation around balance and this idea of pursuing, not necessarily greatness, but like, you know, trying to be a master of your craft. And the idea that you can be great at several things, but perhaps not at the same time. And when you have important values in your life that come into conflict

• 13:18Rich Roll?

  in terms of your bandwidth and ability to attend to them, that's a very real problem. So how do you manage that, knowing like, hey, you know, my marriage, my family life is super important. What I do with Shopify and the impact that I'm having in the world and my philanthropy and all of these things are all very important, like, but you know, it's a little bit like whack a mole, right? So how do you make sure that everybody's attended to in the manner in which you want to make sure that they are?

• 13:49Speaker 01

  When I was younger, I'm not really a big video game guy now, but I used to play video games when I was a kid. And one of the video games I loved was Street Fighter. And one of the things I always thought was funny about Street Fighter was prior to starting the game, you picked your character. And if you played Street Fighter, you'll sort of visualize a character screen. And each character, you sort of see different levels. So like defense, offense, jump, whatever, kicking, punching. But no character had everything, right? Like if they were really good at jumping, they were really bad at like punching or something like that. Based on my skill set in playing this video game, I would select the character that was the most appropriately designed for what I was good at the video game. I think about it a little bit like that, where I don't think I can be great at everything. Not that I even try to do so.

• 14:32Speaker 01

  So I try to pick the things that like really matter to me. Shopify is not. A job for me, it is very much my life's work. We can get into a little bit about what that means to me because I think the concept of life's work is a very contemporary term. I don't think my grandparents or my parents even ever use that term because for them, employment was a means to put foot on the table. And this idea of actually having a personal Venn diagram overlap with a professional Venn diagram, like your personal interests and your professional interests like are kind of the same thing, that's what Shopify is for me. So it's a, it's a very much, for better or for worse, a very personal pursuit as much as it is a large company.

• 15:14Speaker 01

  So that's important and I've, I think the second you, you raise money, you take your company public, you're basically committing that this is going to be like your main quest. So I try not to have any side quests. So that's a main quest. Lindsay, my wife, and my daughters, Bailey and Zoe, they're a main quest. And I probably have a little bit of room for some sort of hobby type thing, but that's kind of it. That means that I can't join a recreational, I don't know, tennis league. It means I can't take the trips that my friends take summertime where they go off to Europe and, you know, gallivant for the summer. Sometimes it feels like if I'm working this hard, shouldn't I be able to do all those things also? I feel the responsibility of the 8,000 people that work at Shopify, the millions of stores that use Shopify.

• 15:58Speaker 01

  I feel that every single day in a very positive way, but that drives me. But that also requires me to say these other things, I'm sorry, I just cannot do them.

• 16:07Rich Roll?

  How do you square that with also understanding that widening your aperture to the world actually makes you better as the steward of Shopify? Like, I know that you're somebody who understands and appreciates the importance of how unlikely influences can impact your entrepreneurship skills, like the obvious example, of course, Steve Jobs, you know, understanding design and Eastern philosophy and all of these things contributing to what made him so compelling and unique. And I'm reminded of David Epstein's book, Range, you know, the idea that, that having a confluence of, of interests and influences can actually make you. You know, uniquely suited to your job and better than you might imagine.

• 16:51Rich Roll?

  With, on the other hand, the idea of like blinders on, focused, getting the job done, all of that, right? Like, you can't be a Renaissance man.

• 17:00Speaker 01

  Yes.

• 17:01Rich Roll?

  And be the president of Shopify, but you also understand like, hey, it might be good if I read some books and, you know, meet some interesting people that are outside of my field to become not just a well-rounded person, but actually, you know, better, better at my job.

• 17:16Speaker 01

  I pick selectively, so I, I, I wish I can have more of those inputs from different areas of the world in which I can sort of, I can synthesize and then use it to do my job better. But I can't do it all, so I'm selective about it. I'll give you a good example. During the pandemic, I felt that I had a pretty good sense of Shopify's product at an enterprise broad level. But for a brand new business starting on Shopify, I built a store on Shopify as one of the first merchants in 2006 or so. So 2020 or 2021, it had been, you know, it had been 14 years since I started a brand new store on Shopify. And I felt that I may have been somewhat out of touch in terms of what are some of the

• 18:01Speaker 01

  trials and tribulations of a brand new entrepreneur getting their first sale on Shopify? So I wanted to, I wanted to start a brand new store. At the same time, I have anxiety, I've had anxiety most of my life. I was switching away from coffee and spending more time drinking, looking for good tea. My best friend, serendipitously, is a guy named David Siegel, who's the founder of David's Tea, built a, probably the only billion-dollar tea company on the planet, took it public, same year as Shopify. And so David was sort of giving me really good tea to try because I was getting off coffee. And at the same time, I also want to experiment with Shopify. And so we built a tea company called firebelletee.com. I've learned more about Shopify's product being sort of a silent partner in Firebelly Tea than I have.

• 18:42Speaker 01

  Being on the road 300 days a year, talking about Shopify's product, talking about Shopify's business. That to me was the perfect example of, that feels like a hobby, uh, cause I get to literally, I had to like register a domain name. I had to figure out like Google AdWords.

• 18:56Rich Roll?

  You're doing the same thing every soccer mom has to do.

• 18:59Speaker 01

  Precisely.

• 18:59Rich Roll?

  Every photographer and it's, you know.

• 19:01Speaker 01

  Yeah, product photography, right? Like, should I take overhead or should I do a 360? Should I use this new augmented reality application? Should I use AI to, to write a, a product description? Should I write it myself? So where I can find something that is going to make my, my role leading Shopify more valuable. And at the same time, I can pull from something unique that is outside of my normal day to day. That's the ideal situation. I actually think 29029 was also like that because what I realized is, um, it was a good reminder that we're about to celebrate our 10 year anniversary since the IPO. So we've done, I've done 38 earnings calls. 39 will be coming up in November and then the 40th will be, uh,

• 19:42Speaker 01

  in 20, early 2025. At a particular point, when you do something for 40 times, you begin to get into a rhythm. And often that rhythm allows you to not go on autopilot, but you begin to kind of like, you get some swagger to the whole thing. On the drive home from the Everesting Race, I remember thinking to myself like, how can I do that totally different? I don't want to get caught in this routine of any of my daily activity at Shopify. Now, again, it's sort of a bit of a, of a cognitive dissonance, you know, mindfuck that like this climbing mountain has brought me to a point where I'm now thinking about doing my job differently at Shopify. But it did because it was a reminder that I can do things

• 20:25Speaker 01

  that are outside my comfort zone, that I can get good pretty quickly, that I can be, I don't have to get into a routine. And I think we as humans, when we get into the routine, it feels really good. We have swagger. We have confidence. We like to kind of stay there. And I think you need someone or something to kind of pull you into that next box. And, and at the bottom of the next box, you're going to feel insecure. You're going to feel out of touch. And so now with my team, I'm trying to figure out, how do we actually rethink the way we do earnings calls? Um, which. You can sort of debate whether there's real value in redoing it. If it like, you know, if it if it ain't broke, why fix it? Actually, I think there is a way for us to do earnings calls much better. Who's the demographic listening to it? What information are they looking for?

• 21:10Speaker 01

  Are we making it as easy as possible? And you will see me try to implement new tactics on subsequent earnings calls that are different than what I did in the past because of what I learned in this everest ing race. That I think is very positive. What I don't think I can do, and this is sort of where the, to use your term, the enough thing comes in, is I don't think I can go and spend four weeks, you know, on safari, right? It's just, maybe at some point I can. I feel a deep responsibility to this business and to the people that have given me this opportunity to not flake for four, four weeks, even if it's going to bring me back very interesting new ideas.

• 21:48Rich Roll?

  Sure. Well, let's go back to the beginning. I, you know, I think of you as a, as a born entrepreneur. I mean, this started quite early for you. So like, walk us through, you know, the, the childhood and your, your first flirtation with entrepreneurship.

• 22:04Speaker 01

  Thirteen years old, Jewish kid, goes through a lot of bar mitzvahs, almost every weekend. There's some other bar mitzvah or bat mitzvah. And I see at all these parties, these, these DJs that are performing. And I think they're like magicians. You know, minute one, you have 300 people sitting down in some like banquet hall or some hotel or some temple, eating chicken dinner. And 30 seconds later, a minute later, you have a conga line happening with people's ties around their heads and light shows. And I just, I thought that these DJs were these incredible magicians. And so I really wanted to be a DJ. I called around, tried to get a job as a DJ when I was 13. Nobody would hire me. So my dad, and this has been sort of a theme with my parents from my life, they didn't

• 22:50Speaker 01

  have a lot of money, but they've always sort of gave me this confidence, this chutzpah to like, just try stuff. So my dad sort of suggested, hey, if no one's going to hire you to be a DJ, why don't you start your own DJ company and hire yourself? And while he didn't give me capital or DJ equipment, he made me a business card and it said Harley Finkelstein, DJ. I actually still have the business card in my home office today.

• 23:17Speaker 01

  And I started a DJ company and initially I didn't make any money because I was like 13 years old, didn't know how to DJ, but eventually I got pretty good at this thing. And I DJed about 500 parties between the ages of like 13 and 19 years old. Mostly Bar Mitzvahs, weddings, that type of thing, private events. By the time I was in college, I realized that whatever I did, entrepreneurship is 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, this really cool tool in a tool belt.

• 23:59Speaker 01

  But where, where things really got serious for me from an entrepreneurship perspective was we moved to South Florida when I was a kid. And 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 move 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 use entrepreneurship to solve that problem.

• 24:44Speaker 01

  This 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, with rent. And so entrepreneurship started as this.

• 25:07Speaker 01

  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.

• 25:20Rich Roll?

  Survival practice, right? Like you learned what you learned when you were younger and when in your moment of need, you realize you could figure your way forward through this experience that you had had previously.

• 25:32Speaker 01

  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. And 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, wasn't my life's work. But this idea of using entrepreneurship to solve the problem became very real for me.

• 26:17Speaker 01

  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. And 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.

• 27:01Speaker 01

  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 met a girl, who's now his wife. And this incredible programmer couldn't get a job because he was a new immigrant. But 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.

• 27:45Speaker 01

  And he would change his business model to focus on helping others build similar online businesses. And I met Toby around that time and became one of the first merchants to Shopify and started selling t-shirts.

• 27:57Rich Roll?

  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.

• 28:07Speaker 01

  Yeah.

• 28:07Rich Roll?

  That was not my experience at all.

• 28:09Speaker 01

  But you actually practiced them.

• 28:09Rich Roll?

  And, uh, yeah. Well, you did for a year, right?

• 28:12Speaker 01

  Yeah, for a year.

• 28:12Rich Roll?

  You did for a year.

• 28:12Speaker 01

  But you were like, you were real litigated.

• 28:13Rich Roll?

  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, their like, risk tolerance, right? Like, 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, you know? I'm gonna do the nonprofit thing, or I'm gonna be a DA or a prosecutor. Then the loans, you know, start to add up and they're like, well.

• 28:54Speaker 01

  Maybe just for a year.

• 28:55Rich Roll?

  I did the summer associate ship. 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, you know, 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. So, yeah, it's interesting.

• 29:12Speaker 01

  I was not.

• 29:13Rich Roll?

  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.

• 29:24Speaker 01

  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 would, I didn't think business school was nearly as valuable. I actually think the skill set 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. But law school was. Read 4,000 pages and pick out the one line that matters most. I mean, that is a very difficult task.

• 29:49Rich Roll?

  It is case study based also, but you have to find, yeah. It teaches you a different way of thinking.

• 29:55Speaker 01

  Yeah.

• 29:55Rich Roll?

  A certain way of analyzing arguments to come up with your own argument. And then like stress testing your ability to like tell a compelling story.

• 30:05Speaker 01

  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 just case breakdowns. But also it was things like the Socratic method in class. I don't know if that was how it was in law school, but at 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 really, really valuable. I think most people on the law school point, most people, I get people messaging me all the time now asking me about law school, if they should go. I think that most people today look at education as simply a stepping stone for the next stage of their life. So they go to medical school to become a doctor, they go to law school to become a lawyer.

• 30:51Speaker 01

  I think if you take a different approach to 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, 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. And 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.

• 31:35Speaker 01

  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. I 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.

• 32:13Rich Roll?

  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.

• 32:25Speaker 01

  It is very helpful to know what you want earlier in life. There's no doubt about that.

• 32:29Rich Roll?

  Yeah, yeah, yeah. For sure. I 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 want to do, right? Hopeful that they'll figure it out along the way.

• 32:46Speaker 01

  It's purgatory. You know, it's like career purgatory a little bit.

• 32:48Rich Roll?

  Yeah, you're sort of being warehoused while you figure out these other things.

• 32:51Speaker 01

  And the good news is that if you want, you can go and make, you know, $250,000 a year out of school after law school, right? Like, it's purgatory, but there is like, there is a default next step.

• 33:02Rich Roll?

  Yeah, yeah, yeah.

• 33:02Speaker 01

  And that default next step is like, by all...

• 33:04Rich Roll?

  The safety net is very high.

• 33:06Speaker 01

  It's very, very high there. And it'll just continue on.

• 33:22Rich Roll?

  I 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.

• 33:52Speaker 01

  Yeah.

• 33:52Rich Roll?

  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. You know, like, when I was growing up as a kid...

• 34:07Rich Roll?

  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 some, or, you know, Morgan Stanley or someplace like that. There was no kind of thinking or incentivization around the idea of like striking out. If you were going to strike out on your own and start your own business, that was like, oh, you're gonna have a sandwich shop or something.

• 34:42Speaker 01

  Or you failed, you didn't get the job. So this is sort of your backup plan.

• 34:44Rich Roll?

  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.

• 35:04Speaker 01

  Right there.

• 35:04Rich Roll?

  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, you 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's very different now. And now being an entrepreneur is sort of this aspirational kind of rock star thing, right?

• 35:24Speaker 01

  Yeah, it's very cool. I do think there is 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 are 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. They came, my grandfather was effectively an entrepreneur. He didn't call himself an entrepreneur. He never articulated that as his like life's work. He sold eggs at a farmer's market, a local farmer's market in Montreal, which still exists today. It's called La Capitan. My uncle currently runs it. He did that because he had no choice. And so this idea forced entrepreneurship, something that I've been thinking a lot about more recently, which is that a lot of immigrants have to become entrepreneurs because they

• 36:09Speaker 01

  don't have a job, they don't have sort of skill set, they don't speak the language. And so no one gives them an opportunity. They 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.

• 36:22Rich Roll?

  Yeah.

• 36:22Speaker 01

  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 had for themselves. And I actually think that there was so many to be said about like being forced into a particular direction, especially as an immigrant, like 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.

• 37:07Speaker 01

  And it wasn't because he was sophisticated or inspiring or this, you know, this entrepreneurial 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. And 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're both doing these projects called, what do you want to be when you grow up? Which is a very common project for, 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.

• 37:51Speaker 01

  And second, it was all about what you want to do later in life. And 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, one in fashion, the other as an artist. I think role modeling is really important and the the original, you know, role models for entrepreneurship, I think are immigrants. And that's what it was for me.

• 38:29Rich Roll?

  A hundred percent. That's so true and very insightful. And it's always frustrating as a parent myself when in school they're meant to do some exercise and by definition, it's like, it's like a limiting exercise, whether it's art class and you got to 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.

• 38:57Speaker 01

  And so, 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. And 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 going to pay for these books. If you like the book and you agree it's a good book, I'm going to 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. And that's what I did. I wrote this book.

• 39:41Speaker 01

  I mean, I really like, 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 going to 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.

• 39:57Rich Roll?

  What are you going to do when your kids want to be doctors and lawyers?

• 40:02Speaker 01

  Good question. You know, my wife, who's much smarter, much more thoughtful of 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. We'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

• 40:46Speaker 01

  more than I want them to take a particular path.

• 40:48Rich Roll?

  Sure. Do you think that, that everybody can be an entrepreneur? You're, you're certainly wired that way. But do you think everybody can have that inclination? As somebody who's, you know, kind of democratizing this world?

• 41:06Speaker 01

  I have two thoughts on this, and, 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 here from, 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 and meeting some of these

• 41:51Speaker 01

  merchants. Some of these merchants that I met with the last 24 hours here, that are 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, 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 Jim Shark has come up. Someone said, who is Jim Shark? 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.

• 42:32Speaker 01

  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 has sort of democratized scale in some ways. Okay, that's on one side. On 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, Bubby'sBlankets.com.

• 43:16Speaker 01

  And maybe you should just, you know, go to a, you know, go on, if you're a grandmother, maybe go on Facebook and you go to Facebook group and you look up a bunch of forums where people are looking for beautiful hand-knit products. And 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.

• 43:59Speaker 01

  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. I 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 Shoplight in 2006 was selling t-shirts. At that point, even 2006, so not that long ago, less than 20 years ago,

• 44:41Speaker 01

  the key ingredient for success on Shopify was who can spend more on AdWords.

• 44:46Rich Roll?

  Right.

• 44:47Speaker 01

  And I couldn't outspend Walmart. So no matter how good I was at entrepreneur-ing, 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 in 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 $1, 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. And that's why I think, right now, is such a great time to do it.

• 45:30Speaker 01

  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.

• 45:39Rich Roll?

  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, you know, 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? And when it's your own mission, there is something, you know, just incredibly uplifting about that. And, you know, I'm interested in this thing that you said that stuck out to me, which

• 46:22Rich Roll?

  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.

• 46:47Speaker 01

  So earlier, we talked about balance. We talked about this idea of enough, and side quest and main quest and all that. The flip side of it is that I don't necessarily think this idea like that your work life and your lifelife 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, Trina's company Figs, now publicly traded, billion dollar company making hospital scrubs, which is amazing business. So I see that very, very often. But I think the greatest way for humans that

• 47:31Speaker 01

  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, I think I often may glamorize entrepreneurship and often may neglect the fact that most businesses do fail.

• 47:53Rich Roll?

  Yeah, even those hobbies that become giant companies. I mean, there's a trail of tears. Like, these things are

• 48:00Speaker 01

  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. But 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 Viori, for example, at least when I buy from Viori, one of my favorite brands, I'm not trying just to buy a pair of shorts or a t-shirt. I'm also voting with my wallet to say, I want more of those companies, those brands

• 48:45Speaker 01

  to exist in the world. Yes, I like the more traditional, you know, big box brands too. But I think what Viori 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. Part of it was even though you could buy from a direct brand, an independent brand, it was less convenient. You went to a big box store, returns, the cash register is right there, they had your information on file.

• 49:30Speaker 01

  But now, using a term we both learned in law school, ceteris paribus, 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 in how they purchase changing, you end up with this incredible surface area of opportunity. I 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.

• 50:07Rich Roll?

  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 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. I'll take a flyer. And thanks to you, like, it's one button.

• 50:31Speaker 01

  Yeah, Shop Pay is pretty good. Shop Pay is pretty good, pretty easy.

• 50:34Rich Roll?

  You've been instrumental in helping me part ways with all the money in my wallet.

• 50:40Speaker 01

  That's right.

• 50:40Rich Roll?

  But I love the Shop app, and then it tracks everything, so you know exactly where everything is and when everything's coming, which makes me feel more comfortable about, like, I forgot about that thing that I ordered, and who knows what happened to it.

• 50:52Speaker 01

  Yeah.

• 50:52Rich Roll?

  But even in terms of your And I love these little brands 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.

• 51:07Speaker 01

  And those little brands that over-deliver, that over-delivering is often something that the large companies cannot do.

• 51:12Rich Roll?

  They can't do it, yeah.

• 51:12Speaker 01

  Because it doesn't scale well. There's a great brand on Shopify called Tacovus, which makes beautiful, beautiful boots, like, boots, 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. And one of the things they are able to do is they're able to get to know their customers. 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

• 51:52Speaker 01

  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. And 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.

• 52:32Speaker 01

  And if you sort of track essentially from that point until 10 years ago, retail was pretty was pretty much the same. Bigger stores, they added, you know, bigger food courts, some of them had like, you know, go karts or they had, you know, water parks, but it was basically the same thing. And 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

• 53:16Speaker 01

  to create something that doesn't exist yet, you will likely have an audience somewhere in the world for your particular product and it's easier now to find than ever before.

• 53:24Rich Roll?

  And when those customers feel well taken care of, they become the evangelists of that brand.

• 53:31Speaker 01

  Totally.

• 53:32Rich Roll?

  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 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. There has to be, like going to a movie, there has to be something more than I'm just going to the shop to get my thing. It has to be an experience that's been cultivated and that seems like what works best.

• 54:12Rich Roll?

  So even the most ardent 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 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 going to be opening up an Apple Store-type experience on Broadway?

• 54:43Speaker 01

  Yeah. There are these brands that just really, really understand their consumer. The 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 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 11:00 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, skateboard, a t-shirt, a hoodie, whatever. And...

• 55:29Speaker 01

  The loyalty and the connection that the consumers, the fans of Serene have to them, is enduring. I mean, Serene is 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.

• 55:51Rich Roll?

  And there's always a line.

• 55:52Speaker 01

  And there's always a line.

• 55:52Rich Roll?

  On Lafayette Street in New York City, every time you go by there, there's like 50 to 100 people in line waiting to get in.

• 55:57Speaker 01

  That's exactly right. Right down the street from there is Kith, who also has a line, but a 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 Bearbrick. Like, there's Bearbricks everywhere, right? The Cause dolls. It's like, 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.

• 56:24Rich Roll?

  Yeah, those videos, I've seen those videos with Scorsese.

• 56:27Speaker 01

  It was unbelievable. So you have that on one side. On the other side, you have brands that, I'll mention this brand again, Figs, who realized that doctors and frontline workers and nurses in the hospital, in doctors' offices, in the clinics, they were all wearing these kind of shitty scrubs. They didn't look good, they didn't fit well. It was basic. And they're like, "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, to this strategy, which is deep empathy

• 57:12Speaker 01

  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. And I 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 believed 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,

• 57:56Speaker 01

  the ones that are most successful are the ones that have deep empathy. From a sales channel perspective, what that also means is Kyle Leahy is 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. And 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.

• 58:38Speaker 01

  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. So 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.

• 59:21Speaker 01

  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.

• 59:29Rich Roll?

  Tell them to lower the prices on those t-shirts. It's insane.

• 59:32Speaker 01

  It's quite expensive, but it is insane. But I mean, I'm wearing it, it's my suit.

• 59:35Rich Roll?

  I have a few, but it's like, it's, it's very expensive. I can't, I can't justify this.

• 59:39Speaker 01

  So James has a bunch of James Purse villas in Cabo.

• 59:47Speaker 01

  These villas are fascinating, not because they're villas and they're a nice place too, but when you rent these houses, anyone can rent them.

• 59:54Rich Roll?

  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.

• 1:00:01Speaker 01

  He goes one step further. He knows your sizes. He knows what you've bought because he's got a great CRM. He 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.

• 1:00:20Rich Roll?

  On hangers that are all like exactly one inch apart from each other and you know, meticulously.

• 1:00:27Speaker 01

  Someone's a little bit OCD, like I kind of love that.

• 1:00:29Rich Roll?

  Yeah, yeah, yeah.

• 1:00:29Speaker 01

  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.

• 1:00:35Rich Roll?

  It's consistent with.

• 1:00:36Speaker 01

  Design, architecture. James makes the playlist for all the 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.

• 1:01:06Rich Roll?

  What'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 going to fulfill that need and then, and then that is our customer base that we're going to 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?

• 1:01:47Rich Roll?

  Like, 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.

• 1:02:04Speaker 01

  We went public May 2015 and in February 2014, we introduced effectively our enterprise plan, we called it 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 start their mom's kitchen table, which frankly, no one really knew was going to happen, some 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

• 1:02:47Speaker 01

  Constant Contact, and eventually you'll upgrade to like Exact Target. There's like enterprise software line for email marketing. Same thing with accounting, right? Maybe you start with QuickBooks, then eventually you end up with like Oracle Financial or NetSuite or something like that. In 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 simply, you use it for a 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.

• 1:03:31Speaker 01

  Or if you're Mattel, for example, which is another one of our stores. So 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 this way, but IPO is not just an interesting event internally, but it also provides, I think, it's almost like an external branding moment. Like all of a sudden, people that are not in e-commerce started hearing about Shopify.

• 1:04:15Speaker 01

  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, I hate the term intrapreneurs, I'm not going to use that, but there are these very entrepreneurial people in these companies, and they were sick of having to do service calls every time they wanted to add a SKU. They're like, it doesn't make any sense, we just want to, we want to change something, we have to like, 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

• 1:04:58Speaker 01

  very large brands began to act like entrepreneurs, and in many ways, they sort of, they sort of stretched us up market, they said, well, we know you don't have everything, but we think we can, we can do everything we need, as long as you, what 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, you know, 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

• 1:05:40Speaker 01

  a point-of-sale terminal, so I can sell in my physical stores too. We 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, it's the worst thing in the world, you're going to confuse them. And, and so we made a very conscious decision, we're not going to shift up market, but rather, we're going to stretch up market. And we want to be the place where everyone goes to start a business, but we also want to be the place that modern brands, 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. And, and that's the reason

• 1:06:24Speaker 01

  why we have such a large, you know, cohort now of very large enterprise businesses, 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, you know, things seem to change a little bit as sort of commerce evolves, is that- We don't just want to be ecommerce. We want to make it easy to sell across every single surface areas, as I mentioned. So what Shopify really is today is more of a retail operating system and ecommerce platform. And why does that matter? It matters because there's going to be a time in the future that someone comes to sell a product and the only place they want to sell it on is augmented reality. They're not going to have an online store. They're not going to have a physical retail store.

• 1:07:08Speaker 01

  They're just going to be powered inside of like, you know, some sort of goggles.

• 1:07:11Rich Roll?

  Apple Vision.

• 1:07:12Speaker 01

  Apple Vision or the Orion glasses from Met or something like that.

• 1:07:16Rich Roll?

  Or within some video game.

• 1:07:18Speaker 01

  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, 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. And that's been a huge challenge from a product and technology perspective.

• 1:07:47Rich Roll?

  Every company has a life cycle, seasons, things change. You were at Shopify in the very beginning when it was 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 like all this, all this admin stuff and everything that gets packed into it. So how have you navigated that for yourself as an entrepreneur to stay fresh and make

• 1:08:30Rich Roll?

  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 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.

• 1:08:55Speaker 01

  It's called the Peter Principle. There's a term for it. Peter Principle is if you eventually get.

• 1:08:58Rich Roll?

  If I went to, if I went, if I got my MBA, maybe I'd know that.

• 1:09:00Speaker 01

  You would have known that, yeah. It's a silly term. I don't know who Peter is.

• 1:09:03Rich Roll?

  They didn't teach that in law school.

• 1:09:04Speaker 01

  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 add 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 my, the only thing that I had to do was figure out a way to do the things that no one else was doing. We 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.

• 1:09:47Speaker 01

  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. There's no room for, 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, 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, chief business officer type people.

• 1:10:32Speaker 01

  They were so well-rounded. 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, they kind of good at everything. And 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 out 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, at that particular role. It wasn't. It wasn't what I was thinking about in the shower. It wasn't my ground state.

• 1:11:16Speaker 01

  It was only in the pandemic where things got a little crazy at Shopify. We ended up divesting a fulfillment business. We ended up having to do some layoffs. It went from 14,000 people to about 8,000 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. The credit goes to Toby on this, that he was really thoughtful. He's like, "We don't 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. 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

• 1:11:59Speaker 01

  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. And internally, I want to be the person that story tells, culture, onboarding, making sure that we are all pointing in the right direction. And I think for a long time, I didn't know if that was good enough, if that was enough. And it was only when Toby

• 1:12:44Speaker 01

  said, "Look, like this thing 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. Don't worry about they'll run it. 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."

• 1:13:13Speaker 01

  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 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, it's, you know, it's a holding pattern, but let's just, just do that for now. And 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, you know, 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, I had that written down as something to Founder mode. Ask you about.

• 1:13:58Speaker 01

  Well, it's not, there's There's sort of like alpha male, like virtue signaling or something? Totally, right? 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 going to be using it to excuse a ton of bad behavior as well, but, but 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.

• 1:14:42Speaker 01

  And I think it also speaks to this idea of micromanagement, which has a connotation of being a very negative thing. And I'm certain, at least today in my role, in the storytelling side of Shopify, I probably micromanage. I don't think it'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, in a press release, or on a tweet, or an X 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

• 1:15:25Speaker 01

  a particular skillset, first, I think it's more impactful, but also it means that

• 1:15:33Speaker 01

  I think you get more longevity, you 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. It's kind of like that at companies. And at a company like Shopify that is growing, you

• 1:16:18Speaker 01

  know, last year, last quarter, our, you know, let's use revenue for example, our revenue grew just above 20% year on year. Shopify is growing 20% year on year. I have to grow at an equal rate or a 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.

• 1:16:46Rich Roll?

  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? Like, what do you mean? Like, what, 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, you know, behind me right here? Like, there's an uncertainty to that, right?

• 1:17:10Speaker 01

  It's really difficult because, you know, quantifying Shopify's growth is very objective. Quantifying my growth as a leader is very subjective. Part of it is, is do I believe I'm doing a better job than I did a year ago? If I watch, you know, an interview that I did, or a call that I did, or, you know, a deal, a partnership deal that I did. If I did it now, would I do it differently? Would 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.

• 1:17:52Rich Roll?

  Sure, they're gonna, they're gonna, you've gotta have those people around.

• 1:17:55Speaker 01

  You need, you need those truth tellers. But that, that I think, that's sort of how we run the company today. Shopify is not a group of well-rounded people. Shopify 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.

• 1:18:21Rich Roll?

  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, you're not worthy of the founder status, right? Just relentlessness. But you can't grow unless you delegate and trust those people to do their job. And both of those things are true.

• 1:18:48Speaker 01

  Yeah.

• 1:18:48Rich Roll?

  Right? And so the job really is how do you reconcile those on a case by case, minute by minute, individual by individual basis?

• 1:18:55Speaker 01

  There's a great metaphor that, that I love, which is the trust battery metaphor. We talked about this a lot inside of Shopify, but basically everyone that starts a company starts at 50% trust battery. Again, the trust battery is a metaphor, so you're not gonna go by 1%.

• 1:19:07Rich Roll?

  You get a certain level of trust, but then you gotta earn the rest.

• 1:19:10Speaker 01

  Exactly. And how do you earn it? You 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.

• 1:19:27Rich Roll?

  Does everybody have a little icon on their office door with how much their battery is charged?

• 1:19:32Speaker 01

  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. But 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 battery goes down and down. And then eventually, like an old cellphone battery, it's impossible to recharge. And that's what I think you have to say goodbye.

• 1:20:01Rich Roll?

  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, you know, 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. And I was at an event recently, a couple of weeks ago, and I saw a presentation by a really compelling presentation by two guys who are former Chiat Day executives who created this agency called Founder, F N D R. They're here in L.A.

• 1:20:43Rich Roll?

  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, et cetera. 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. Like, 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

• 1:21:24Rich Roll?

  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. How 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?

• 1:21:54Speaker 01

  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 is success. It's about opportunity. It's about democratizing.

• 1:22:14Speaker 01

  Your thing, distributing something that really matters to you. But I also think it is easier to be, to tell a good story if you have tenure, if you have longevity, if you really believe in this thing. Many years ago, I met a very well-known, very senior executive who's now in his 80s. And he'd worked at seemingly 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 or was at 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's just, it was all widgets to me. And he's like, I use the same tactics and the same strategy at company A as I did at

• 1:22:58Speaker 01

  company H. And I said, that sucks. He's like, 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 for 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 preclivities he has, but who could run Tesla or SpaceX better than him? He just, he lives this stuff. He dreams about this stuff.

• 1:23:42Speaker 01

  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.

• 1:23:57Rich Roll?

  You hear it all the time.

• 1:23:58Speaker 01

  Yeah.

• 1:23:59Rich Roll?

  You hear it all the time. Private equity comes in or whatever.

• 1:24:01Speaker 01

  I'm gonna put in McKinsey, BCG.

• 1:24:03Rich Roll?

  Yeah, like, we're gonna, we're gonna put in operators. These people, this guy, was it Pepsi or whatever, Coca-Cola?

• 1:24:09Speaker 01

  I mean, McKinsey's right there right now, right? As we speak.

• 1:24:11Rich Roll?

  Yeah, it's a reckoning.

• 1:24:12Speaker 01

  That's right. It's a reckoning. And the person that is going in.

• 1:24:15Rich Roll?

  Because the vision exited.

• 1:24:18Speaker 01

  Exactly.

• 1:24:19Rich Roll?

  And, you know, without that, like, the entire mission capsizes.

• 1:24:23Speaker 01

  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. And 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.

• 1:24:56Rich Roll?

  Yeah.

• 1:24:56Speaker 01

  And worked his way up into this role. I mean, it's kind of in a...

• 1:24:58Rich Roll?

  Which is interesting.

• 1:24:59Speaker 01

  Very interesting.

• 1:25:00Rich Roll?

  Yeah, because usually that person comes from the outside.

• 1:25:03Speaker 01

  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. It's just an amazing... I mean, it feels very Phil Knight, Shoe Dog-esque.

• 1:25:17Rich Roll?

  But here's the button on this whole thing. You guys work with ON, right?

• 1:25:20Speaker 01

  Mm-hmm.

• 1:25:20Rich Roll?

  Yeah, here we go.

• 1:25:21Speaker 01

  Great company.

• 1:25:22Rich Roll?

  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.

• 1:25:30Speaker 01

  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, 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. It 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?

• 1:26:14Speaker 01

  The carpenter who cared about the back of the, of the bookshelf as much as the front? A professional manager, some may, there's some really good professionals, 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's of the whole thing. And... 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.

• 1:26:55Speaker 01

  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.

• 1:27:14Rich Roll?

  And that intimacy can be maintained at the Ons, 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, was it yesterday? Yeah, I think it was today. You posted about Tom Holland, who just announced the launch of Bureau, his non-alcoholic drink.

• 1:27:47Speaker 01

  Which I've tried, it's delicious.

• 1:27:48Rich Roll?

  It's good. He was here a couple of months ago and we recorded a podcast to help him tell that whole story. That one's going up this weekend because now it's public. But we were, yeah, he was here a while ago.

• 1:27:59Speaker 01

  It's unbelievable.

• 1:28:00Rich Roll?

  Doing, yeah.

• 1:28:01Speaker 01

  So two years sober, part of his journey was...

• 1:28:02Rich Roll?

  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.

• 1:28:22Speaker 01

  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. His name is Reed, with Jimmy.

• 1:28:33Rich Roll?

  For Mr. Beast.

• 1:28:34Speaker 01

  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 billion market cap and we were sort of laughing at, one day can Feastables ever buy Hershey's? And 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 Reid's like, "There's no one on the planet that knows more about chocolate right now than Jimmy does."

• 1:29:15Speaker 01

  That Jimmy knows so much about like the ratios of ingredients and forget the marketing, because he, you know, Mr. Beast 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. But 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 Beast Burger in LA versus Milwaukee. They shut it down.

• 1:29:59Speaker 01

  It'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 80s, apparently. And I don't know who he 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

• 1:30:42Speaker 01

  and you went to the merch booth and like you got this like shitty t-shirt on the back at 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, a cosmetics company which is on Shopify. These 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-

• 1:31:26Rich Roll?

  No, no, no. He spent a lot of, a lot of time on it.

• 1:31:29Speaker 01

  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 ahead and build an audience. And what, what is happening right now is 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, 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, it's really exciting to see that.

• 1:32:08Rich Roll?

  They also understand that if the offering isn't authentic to who they are, it's not going to work, right? These are people who have built their audiences over time and understand what these people want. And, 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, 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, that will get rooted out. And in business, shit happens. But now like, there's almost an expectation that you're going to tell the customers like,

• 1:32:53Rich Roll?

  hey, look, this went wrong or we made this mistake. And I think people are very forgiving if they feel like there's integrity and honesty in that exchange.

• 1:33:02Speaker 01

  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-

• 1:33:14Speaker 01

  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, I want to tell you about how we did in the quarter, here's about highlights, here's what I'm excited about. Even 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 implement that way.

• 1:33:34Rich Roll?

  Yeah, I mean, you're a publicly traded company, you gotta be pretty judicious in what you say.

• 1:33:38Speaker 01

  For sure.

• 1:33:39Rich Roll?

  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, like there's real ramifications of that.

• 1:34:02Speaker 01

  But it also means, even for your show, Rich, like for what you're doing here with your podcast, you don't have to ask permission for any, 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.

• 1:34:30Rich Roll?

  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, so, you know.

• 1:34:38Speaker 01

  You're a great entrepreneur, it's amazing.

• 1:34:39Rich Roll?

  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, like-

• 1:34:48Speaker 01

  It's authentic and it's yours.

• 1:34:49Rich Roll?

  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.

• 1:34:58Speaker 01

  The metaphor that I find fascinating is, this mic we're using right here is an SM7B. Yeah, very famous microphone.

• 1:35:05Rich Roll?

  Been using it for a very long time and this is, it's unchanged for decades.

• 1:35:09Speaker 01

  It's one of the only piece of technology that's been unchanged, but there is something different. People like you, like a content creator, a podcaster, didn't have their own Sure SM7Bs 10 years ago. You used to go to studios to rent Sure SM7Bs. I have Sure SM7, I have it at my home office. This is like at my desk where I go on Skype or Zoom or Google Meet, I'm using a Sure SM7B. In many ways, that to me is like a proxy for what is happening here. That like we've, we've, we've literally taken the tools that didn't, 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 Sure, the SM7Bs now belong to us. And that's the entrepreneurial, that's the technology change that has happened.

• 1:35:52Rich Roll?

  Hmm. I want to switch gears a little bit and talk about mental health. You mentioned issues with anxiety over the years. You turned 40, Masogi, 29029, you're thinking about...

• 1:36:03Speaker 01

  I'm following your footsteps.

• 1:36:04Rich Roll?

  Your own, your own personal, except you didn't have to go through some kind of crisis for it. Like you just volunteered for it? Like God bless you. But mental health is something that, that, 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?

• 1:36:26Speaker 01

  When I was in grade school, a teacher of mine, I think it was in the 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...

• 1:36:41Rich Roll?

  Are you stuck in the past or are you stuck in the future?

• 1:36:44Speaker 01

  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 learnt about when I was a kid. I was like, I'm constantly thinking about what is next. And 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 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.

• 1:37:29Speaker 01

  I always thought that it was a very personal, very vulnerable, just not my style. Like, same way I told you, you know, when I cried at the end of Everest Stank, 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 thing to 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. And so I began to do it again.

• 1:38:13Speaker 01

  I was like, okay, well, um, you know, sometimes I wake up in the middle of the night and like my, 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 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 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. So go back to sleep and in the morning, prefront, you know, Mr. and Miss 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.

• 1:38:54Speaker 01

  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 you wake up in the night. And people are like, like people that were in their sixties and seventies and eighties who were really thoughtful about this stuff would tell me like, huh, I didn't think about, I never thought about it in that way. And so I just made a decision a couple of 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 and here are a couple of 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

• 1:39:39Speaker 01

  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. And so that's the reason why I've continued to share it. And I find it to be, I've now been able to build sort of this toolbox of tactics. I mentioned to you earlier that, you know, I'm part of this longevity league of these people that really care about longevity. And we do this longevity weekend every year in Muskoka, and it happened a couple of weeks ago. And I actually brought my mindfulness coach with me, and we did a presentation, and we talked about this, it's, I know, it sounds super cheesy, but-

• 1:40:12Rich Roll?

  Sure you don't live in LA?

• 1:40:13Speaker 01

  I don't live in LA. I live in Canada.

• 1:40:15Rich Roll?

  It's a very un-Canadian thing.

• 1:40:16Speaker 01

  I know. There are a bunch of LA people in this group, as you know.

• 1:40:19Rich Roll?

  But I know some of those Muskoka folks.

• 1:40:21Speaker 01

  Yeah, they're very LA-esque. But I brought my coach, and I actually 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. I was like, dude, you're 75 years old. Like, I look up to you in every aspect of your life. Like, there's no way

• 1:41:06Speaker 01

  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.

• 1:41:35Rich Roll?

  So 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, this instinct or compulsion to compartmentalize whatever our dysfunction is and, and, 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? Like, your anxiety is what fueled your, your drive to be relentless.

• 1:42:17Rich Roll?

  Or, you know, the bond trader who convinces himself that his gambling addiction is actually making him a better trader. Or, you know, the heroin addict who thinks they, you know, that's why they're able to write great songs, you know, 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, but it's a short-term unsustainable fuel, right? And you're either going to crash and burn, you're going to, you know, hit the wall with it and realize you're going to have to find a different way. Or, 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.

• 1:43:01Speaker 01

  And also, I don't want to lose that. I don't want to, I don't want to, I was sort of worried a little bit about

• 1:43:06Rich Roll?

  If you were completely equanimous, yeah, how are you, are you going to be able to get up in the morning? And this is the dilemma, right?

• 1:43:13Speaker 01

  Correct. So let me share something that happened this morning, more than I was planning on sharing, but, 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. And I think it came out last week.

• 1:43:29Rich Roll?

  It just came out, yeah.

• 1:43:30Speaker 01

  Yeah. I had not watched it. And I was like, I need to watch this right away. Now, it's quite a long podcast. And, 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 a super fascinating guy, but also 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 and the this incredible opportunity for me to come on your show is an honor for me and I take those things very seriously.

• 1:44:09Speaker 01

  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, to you, but mostly to myself, to know what is Rich's most current version of the world, his most current perspectives on things. And 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.

• 1:44:54Rich Roll?

  But that choice can be generated from something else other than anxiety.

• 1:44:57Speaker 01

  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, Squawk Box, 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. I 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 focused on it because it was, I thought it was very important. I wish it wasn't only anxiety based, but if that's the reason that

• 1:45:41Speaker 01

  I'm able to be good at the things that I do, or better things I do that I would, that I wouldn't otherwise, I'll take it.

• 1:45:47Rich Roll?

  Hmm. 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.

• 1:46:02Speaker 01

  That's not okay. Yeah. So 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 it 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. And so I'll say, give me 10 minutes, time me if you want, I'm gonna go outside the restaurant. And, and Lynn, if you want to leave, like, you don't want to sit 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

• 1:46:47Speaker 01

  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.

• 1:46:56Rich Roll?

  So what changed? Ah, is it this mystical 40?

• 1:47:01Speaker 01

  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. And 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 nights, you know, snuggling up and waking up with the, with the two, with our two daughters in the bed. I don't know, maybe it's just getting older. Maybe it's meeting more people who explained to me, people that I thought I admire, back to that, like, 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

• 1:47:45Speaker 01

  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.

• 1:47:59Rich Roll?

  Yeah, 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?

• 1:48:11Speaker 01

  Yeah.

• 1:48:12Rich Roll?

  Because, listen, you've, you've scaled a huge mountain. There's always more mountains to climb, but what is that really gonna do for you?

• 1:48:18Speaker 01

  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, 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. Am 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.

• 1:48:57Rich Roll?

  Yeah, but they never, when they get it, they never retire.

• 1:48:59Speaker 01

  Literally zero. I had, I have great mentors. Like, I've had over my life, dozens of incredible people. Not 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. 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 seventies, eighties and nineties. I interviewed Izzy Sharp, 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. But two, the business model is very unique because the real estate is owned privately.

• 1:49:39Speaker 01

  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.

• 1:49:51Rich Roll?

  Novel model.

• 1:49:52Speaker 01

  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, a storied entrepreneur. And I put Four Seasons in the same class as like Apple from a brand perspective. But also, like, I'm not sure I want to say that when I'm 93.

• 1:50:21Rich Roll?

  Yeah. It's sort of sad. Like, what is making it mean? And what is driving the desire to quote unquote, make it however you define that, right? And I think if you're mission based and, and that mission is tied to serving people and making the world a better place. And, and that mission has no end. Like, there, there will never be, you know, 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. But. If making it or just, you know, climbing this endless mountain is about filling,

• 1:51:01Rich Roll?

  you know, 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.

• 1:51:11Speaker 01

  Yeah.

• 1:51:11Rich Roll?

  Right? So what are you chasing? And on some level, it's back to story. Like, what are you doing? Like, what is, what is, 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, you know, victims of our ego, living in the material world, like chasing shiny things and running around like, you know, with our, with our heads cut off. But 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?

• 1:51:48Speaker 01

  That's right. And there's this fine tension because the people that are, 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. And 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.

• 1:52:31Speaker 01

  And whenever I'm sort of struggling, I always sort of go back to this thing, it's 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, check. 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 on Friday, back to Canada. And I'm just, like, I know exactly, like, what I want to do Friday night. Like, 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 gonna watch a particular movie, and I'm really looking forward to it. 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-

• 1:53:15Speaker 01

  I just kind of keep going back to that, like it's so simple. Someone 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.

• 1:53:24Rich Roll?

  I believe you, I believe what you just said, but I also think this. Are you ready for this?

• 1:53:31Speaker 01

  Let's go.

• 1:53:31Rich Roll?

  I bet you're terrible at vacations.

• 1:53:34Speaker 01

  Terrible vacations.

• 1:53:35Rich Roll?

  Yeah.

• 1:53:35Speaker 01

  Terrible vacations.

• 1:53:36Rich Roll?

  You can't turn it off, can you?

• 1:53:38Speaker 01

  No, but on vacations, what I realize is that I'm actually really good at like one week vacations. I'm really bad at two week vacations. So what that, what does that mean? It means that I, I really love, like my weekends are really fun. I really enjoy my weekends. I, 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. I 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. And I was like, and I cannot do that right now. I don't think I have the, I don't, I don't.

• 1:54:07Rich Roll?

  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 want to do, they want to ride mountain bikes across Vietnam or something, whatever, right? You have an opportunity to do this. Do you feel the anxiety?

• 1:54:37Speaker 01

  Yes.

• 1:54:37Rich Roll?

  Right, so, so the question then becomes like.

• 1:54:40Speaker 01

  I can lie and say.

• 1:54:41Rich Roll?

  What's behind that? Like what is the discomfort with, with sitting still with yourself, right? And I think that's the teacher, right? If you can go, I'm, I'm saying this as somebody who has the same, you know, I'm, I have the same thing.

• 1:54:54Speaker 01

  How are you vacations?

• 1:54:56Rich Roll?

  A lot better.

• 1:54:56Speaker 01

  Yeah.

• 1:54:56Rich Roll?

  But I'm older, you know, I'm older than you. But yeah, like.

• 1:54:59Speaker 01

  Does it get easier?

• 1:55:00Rich Roll?

  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's something there to examine.

• 1:55:10Speaker 01

  My favorite beach in the world is Turks and Caicos. I just think it's a beautiful beach. It's really lovely. I get to go there with my family every year. And when I'm there, I try to like, you know, the first couple of days, I'll sit around the beach and play. And then I'll go take a kite boarding 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 by myself and listen to a podcast. But I'm beginning to, rather than pretend, and that's the thing what I used to do. I think my, the old version pretended to be good at vacation.

• 1:55:50Speaker 01

  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, ask myself those questions. Why can't, why can't I just sit on the beach? What is preventing that from happening? And I, 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.

• 1:56:14Rich Roll?

  So if Lindsay, your wife, is sitting across from me right now and I asked her like, what is Harley's major malfunction? Or like, what is the thing that comes up in your marriage that, that is the biggest challenge for her?

• 1:56:25Speaker 01

  She would say, I can't sit still. And sometimes that, that affects her.

• 1:56:27Rich Roll?

  Yeah, that's what I thought.

• 1:56:29Speaker 01

  Yeah.

• 1:56:29Rich Roll?

  It's that same thing, like, well, that's, that's the same energy that makes me successful. You don't, you don't get one without the other. You can't have, you can't have it both ways, right?

• 1:56:38Speaker 01

  I don't know. I, I'd like, I'd like to try.

• 1:56:40Rich Roll?

  Yeah, so I'm not saying I have an answer to that, but I just think it's interesting and worth investigating.

• 1:56:45Speaker 01

  What, what has happened to you that has actually created the most amount of self-tolerance to allow you to do a vacation? Has there been something that, other than just sort of getting older?

• 1:56:55Rich Roll?

  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.

• 1:57:03Speaker 01

  Right.

• 1:57:04Rich Roll?

  I took a month off for the first time right before the pandemic because I was teetering on burnout, you know? And I was incredibly just like, sort of uncomfortable in that. And now I do it proactively every year. It's like a prophylactic, like it's built into my year.

• 1:57:17Speaker 01

  Yeah.

• 1:57:17Rich Roll?

  And every year that I do it, I untether a little bit more. Like, you know, 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, I didn't look at my email once. And like, everything was, it was great, you know? So 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?

• 1:57:59Rich Roll?

  There is a Harley outside of that that is worthy of honoring.

• 1:58:03Speaker 01

  There is this, back to law school friends, I met with a law school classmate of mine a couple of years ago, probably five years ago, and he was just supposed to become a partner at a big law firm, like a big white shoe law firm with all the accoutrements and all the things that comes with it. And 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 the worst time of the week. I was like, what do you mean? He's like, I hate Sunday nights. I was like, why? He's like, because Monday's coming the next day. And I'm like, huh. And I was like, let it go, didn't think much about it. I called him back a couple of weeks later. This is probably five years old now, 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 know there's like these sort of memes around Sunday scaries, but part of the reason

• 1:58:46Speaker 01

  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 Friday nights.

• 1:58:56Rich Roll?

  That's a gift, though. And that's not, that's not most people's experiences.

• 1:59:00Speaker 01

  And I acknowledge that, and I actually acknowledge the fact that that is incredible privilege, that my Saturday morning, that feeling of 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.

• 1:59:26Rich Roll?

  Okay, yeah, come, report back.

• 1:59:28Speaker 01

  I'll report back of how I'm doing.

• 1:59:29Rich Roll?

  Well, before we, we kind of close this down, maybe we can, you know, 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, it's not, this isn't Not a business podcast. Most people listening to this, maybe, you know, a bunch of them have side hustles or their 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?

• 2:00:04Speaker 01

  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. And 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, 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. He constantly was bringing me tea. He was constantly was talking about tea, but he himself didn't actually realize

• 2:00:48Speaker 01

  that like his next thing should also be tea related. The reason I bring up this particular story about David is because if the king of tea, like his name on Instagram is literally T 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. And so the first thing I'll say to you is for those listening that want to 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 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

• 2:01:34Speaker 01

  this imposter syndrome of, of entrepreneurship, it's, it's only in your own head. Almost every merchant on Shopify that has started on the, 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. That there is this, there is this assumption or presumption, I should say, that at a certain level of success, you haven't figured it 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 on 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

• 2:02:17Speaker 01

  isn't actually knowing what to do. It's knowing that whatever comes your way, you'll be able to figure it out. The second thing. The third thing is back to the cost of failure. Like, 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 and it 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,

• 2:02:59Speaker 01

  like a skateboard deck. And I think that there is this, 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, to, to the first 10 customers because they have to have in 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. If you were thinking of starting a business, those are the things that I would think about today. And I would, I'd love to help in any way I can. I am, I pray at the altar of entrepreneurship.

• 2:03:41Speaker 01

  Shopify prays the altar of entrepreneurship. And we want more of those to exist in the world.

• 2:03:47Rich Roll?

  Yeah. That was awesome, man. Thank you.

• 2:03:49Speaker 01

  Thank you.

• 2:03:50Rich Roll?

  I really appreciate you coming here to share today.

• 2:03:52Speaker 01

  Thanks for having me on. It's great on.

• 2:03:53Rich Roll?

  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, you know, create something unique and special. Like, I think it's awesome.

• 2:04:06Speaker 01

  Yeah. And despite you not thinking you're an entrepreneur, you're an incredible entrepreneur. And this is really fun.

• 2:04:12Rich Roll?

  Yeah. Thanks, man. We did it. How do you feel? You feel good?

• 2:04:15Speaker 01

  It's great. Yeah. I can do this all, I can do this all day. Keep going.

• 2:04:17Rich Roll?

  Well, come on back.

• 2:04:18Speaker 01

  I'd love to. Yeah. With less anxiety.

• 2:04:35Rich Roll?

  That's it for today. Thank you for listening. I truly hope you enjoyed the conversation. To learn more about today's guests, 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. This show just wouldn't be possible without the help of our amazing

• 2:05:17Rich Roll?

  sponsors who keep this podcast running wild and free. To check out all their amazing offers, head to richroll.com/sponsors. And sharing the show or your favorite episode with friends or on social media is of course, awesome and very helpful. And finally, for podcast updates, special offers on books, the meal planner, and other subjects, please subscribe to our newsletter, which you can find on the footer of any page at richroll.com. Today's show was produced and engineered by Jason Camiolo. The video edition of the podcast was created by Blake Curtis with assistance by our creative director, Dan Drake. Portraits by Davy Greenberg. Graphic and social media assets courtesy of Daniel Solis. And thank you Georgia Whaley for

• 2:06:02Rich Roll?

  copywriting and website management. And of course, our theme music was created by Tyler Pyatt, Trapper Pyatt, and Harry Mathis. Appreciate the love, love the support. See you back here soon. Peace. Plants.

• 2:06:16Speaker 01

  Namaste.