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Startup to $15 Billion: Finding Your Life's Work with Shopify's Harley Finkelstein

Lesson 131 from: The Chase Jarvis LIVE Show

Chase Jarvis

Startup to $15 Billion: Finding Your Life's Work with Shopify's Harley Finkelstein

Lesson 131 from: The Chase Jarvis LIVE Show

Chase Jarvis

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131. Startup to $15 Billion: Finding Your Life's Work with Shopify's Harley Finkelstein


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Startup to $15 Billion: Finding Your Life's Work with Shopify's Harley Finkelstein


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Lesson Info

Startup to $15 Billion: Finding Your Life's Work with Shopify's Harley Finkelstein

every What's up? It's chase. Welcome. Another episode of the Chase Jarvis Live show here on creative life. You know this show. This is where I sit down with amazing humans and I unpacked their brains. Do everything I can to help you live your dreams and career in hobby and in life. My guest today is a lifelong entrepreneur. He is the c 00 The chief operating officer of the most badass company that I was probably friends with. The earliest Shopify. My guest is Harley Finkelstein. We love you. How many years in the making? A long time. Even trying to get me on the shows for a long time Way first. I think we met each other five years ago through the build A business competition. Yep, which is really fun. That was incredible. And that was you had, like, 100 plays. Then I think 1917 60 we have more than 3000. So it's been quite a journey. So that's obviously one of things I want to talk about today. The our origin story Be fun to trace back because I think the build a business competition. ...

Would you, uh you and launch with a bunch of peers and friends of ours that mutual acquaintances. I do want to talk about that, but I want to talk about the way back. Most of the folks who I know who built what's it like? I don't know what your market cap is. 15 billion or some create like crazy came on 16 plays, not $15 billion market cap, publicly traded company out of Ottawa. A tomato can, Um, but I I don't know your entrepreneurial journey, so I'm saving it for this very moment. There's no no no research because I know that most people who have built businesses like you have had this entrepreneurial like vein some something like goes way back to their childhood where they were, like washing cars or selling crowd ads or selling golf balls, which I used to like watch golfers hit the ball out of the water and go get it and saw it back home for like, five. That's a dangerous for Let's look at me. E had a couple times, plenty of times. So what's your entrepreneurial journey? Because you know that you know the show really well. Don't need to explain to you? Yeah. So my my journey kind of starts back when I was 13 years old. Um, I grew up in a sort of suburb of Montreal in Canada and around 13 years old. You start going apartments is no my friends, that my Jewish school friends, olive bar mitzvahs. And I remember seeing these DJs at these bar mitzvahs. And to me, they were just the coolest people in the whole world. They have headphones on and they were mixing and they were dancing and just look like a lot of fun. And so I decided I'm gonna be a deejay. And the problem was, I had absolutely no skills. I'm still pretty short, but I was like, four foot nothing at the time. And so on. YouTube wasn't around, so I could teach myself had a deejay. But it was I started calling around and seeing if someone hire me and turned and no one's gonna hire a 13 d j with no deejay skills. And soon it just wasn't was gonna happen. And so I decided I would start my deejay company and hire myself. And that was it. I just kind of decided it. My Dad actually has always been supportive with all my crazy ideas when it made me business cards, which gave me this great validation that maybe I could do this thing on, I wouldn't bought some D J equipment and taught myself how to beat Max. Just counting beats 1 to 8 and figuring out a fade and just kind of the basics of D. J. Did you go to the line and very I mean, what a library. I just kind of bought this equipment in my basement. Just just figured stuff out and again, I had to buy a lot of CDs because obviously that was only to do. There's no cerrado than our traditional music, but I bottle this stuff and borrowed money from my parents. And actually, my dad was great because he lent me the money, wasn't much money was like five or 600 bucks, But he taught me about interest. He's like, All right, well, I'm gonna let you this money, but on a weekly basis, I'm gonna come back and collect the interest that you owe me, and eventually you're gonna pay back the principal. And it was a great lesson for me. in finance but end up teach myself a deejay and then going around the neighborhood and trying to convince neighbors toe let me d j bar mitzvahs and birthday parties and weddings and barbecues and ended up doing like 500 parties between, like, 13 years old and years old. And by the time I was 1700 a year, it's a lot. Yeah, on and on every week, like the nine Oclock show, the midnight show that I was in school, I was in high school, right? I was. I was a kid and ended up doing a lot of these parties and actually falling in love with the business side of the business. Not necessarily the deejay the art side of and I loved sort of. A couple things I learned then was learn how to read the crowd, right? Like just because I want a hip hop, I know those guys want to listen to disco. I'm gonna disco. Also making sure that the client loved me before the party started was this easy way to ensure it. Things went well. My sort of philosophy was that they love him before the party, no matter how the party goes, it's gonna be good. Just making sure. Creating a good vibe, good energy with the clients. And that was kind of my first journey into entrepreneurship. And, um, I, I still known to embarrassed embarrassingly deejay Cem shop like Christmas parties to this day. Although last year my wife said, All right, this is it. You're like, You're not cool anymore. That's right, 3000 people. They actually want to have a good time. Yeah, it's kind of embarrassing. And old do Doesn't really know, like, good New music Way cool. So that was the opposite for me. It's a very common thread for people who've been in the show, and there's been some whoppers like You've built something from nothing. And that's a really common thread that there's this early, early sort of makings of a business person entrepreneur, a creator. Where did you get it? So do you Do you attribute it to anything in particular? Is that your parents, particularly entrepreneurial are not really mean, Like my dad was an entrepreneur? Uh, not a particularly good one at that, but, um, in the same way, So entrepreneurship solved the problem that I had, which is, I want to be a deejay and no one would hiring. And so I used entrepreneurship to solve my problem. And that was like a 94. Something like that in 95 95. But if you go back to like 56. 55 56 57 my grandparents came to Canada from Hungary. It was the hunger and revolution Canada had lead in, like 40,000 immigrants. And my grandfather had a problem, which was he survived to put food on the table. He had no money, no education. He didn't speak English, and so he started selling eggs at a farmer's market. And I think in some ways, in the same way that he used entrepreneurship to solve his problem, which was, frankly, poverty. And I used it to solve my problem, which was this passion for entrepreneurship. I sort of always Susan's passion for D. J. I always sort of assumed that entrepreneurship just may just be this thing. This catalyst problems off. Yeah, and actually, a couple years after that, um, I, uh, I was an undergrad, was in college. It was 2001 wins. McGill University, Montreal and my dad wasn't able support anymore, and I found myself another problem, which was I either had to move back to live with my parents and they were living in South Florida time or stay in Montreal and support myself and kind of take care of my tuition and ended up building a T shirt business then. And so once again, entrepreneurship was the solution. My problem in this case, it wasn't this passion for D. J and not be able to get hired. It was, um I need to make money and I needed to do it concurrently while being in class. And so I spent four years of my undergrad in college years studying a little bit of really building this T shirt business and making T shirts for about 50 universities across Canada. And again, I just was. It was another reminder that my life's work, no matter what I'm gonna do well, involve entrepreneurship in some way. Well, is there a So there's the theme than you presented that very clearly is solving problems, and I'm gonna fast forward to today, which is I think if you've been living under a rock and you don't know Shopify, his It's a company that basically provide. Well, I'll let you explain it. You explain what shop? I was actually curious here. You could explain it, but But I'll take take the lay up there. Um, so the roots of the company is that back in 2000 for we were trying to self snowboards on Internet, and I know four. There was basically two ways to sell a product online. One way was you paid a $1,000,000 to have some custom enterprise solution built, and that's what Wal Mart did, and all the big becomes like that did. And the other way was you would sell on a marketplace like Amazon or eBay or Etsy, and the first option was too expensive in the second option. Although it was less expensive, it didn't really lie to build your own brand. Yeah, and so this your eyes, someone else's mark. You're renting customers effectively from the marketplace, and there's and that's right. And in actuality, the success. Your business was tied to someone else's interest in helping you and eso this really, really smart programmer named Toby who you know, are CEO and founder Toby decided that he wanted self snowboards online and didn't find any good software. And so he wrote this piece of software to sell these noble It's and within a matter of a year or so, he started realizing there are people out there like me who wanted to use the software to sell their own products. And he decided, by 2005 that snowboards is maybe a good idea. But the software behind the online store business was a great idea. It's like during a gold rush. So Accel picks exactly. That's right. Yeah, actually, Levi's jeans, That's how they started. Rachel Nichols, Russia's Well on. And so we basically spent the next, you know, up until probably in 2013 becoming what I think is the leader in helping small businesses build great online stores. And we had tens of thousands or even 100,000 stores up until that point, use us to build great online businesses, and really, the tenants were making really easy. So if you had to use email, you can build a store on Shopify within like an hour, make it super scale. It'll make it easy to customize, and that really was the core of the business. And by 2013 it dawned on us that if we want to be relevant as retail and commerce develops, we have to sort of rethink what is the value that Shopify provides to our merchants. And it it looks like the future of retail wasn't gonna be necessarily just online Or was it going offline? That may be the future. Retail is going to retell everywhere. And if we want to be a company that can just a lead in Commerce retail, we have to provide a product that allows entrepreneurs and small business to sell everywhere they want online, offline on Facebook on instagram and Marketplaces ends. Uh, and that's kind of what we've been working on to date and many years in Esso. Now it's been about it's been about 13 years or so 14 years or so since we're working on this thing and we have more than 600,000 stores. And the interesting part is, even though Shopify was always built for small businesses and still that's who we care most about. We've seen companies like Procter and Gamble and Unilever and Pepsico on and Kanye and Kylie and Drake and all these big brands all build stores on Shopify. And what's fascinating is that we're seeing now some of these larger companies beginning to act really entrepreneurial. But the's 600,000 stores or so on our platform they've sold more than $60 billion on Shopify. And if you bought a really great product that you actually love in the last little while online and the experience was amazing, there's a really good chance that was shot. It's it's true and that's like No, not blowing smoke like it is a legit product. It is beautiful. It is fast. The back end is like I We are one of those folks at Creativelive. We built our store from the ground up only because we have a bunch of nuances to our platform. But obviously we're a community of tens of millions of creators and Spotify is far and away the leading platform for shocked by Not suppose Spotify is great terror Amazing, But Shopify is the leading the leading purveyor of the store. So one of the things that is handful the ways I want to take this now. So put a pin in how awesome Shopify is and what it stands for. How did you decide that SMB or like this? This market of independent creators and entrepreneurs and watchmakers? And like when I did the build the business competition with you, you guys will go there in a second. I was just shocked at the variety of of types of people who are selling stuff on your platform. It seems like that's but there's still a target. It's not. You're not for everybody's because as soon as you try and build something for everybody, you build it for nobody who do you serve? How did you choose them was a default. Because, you know honestly, when I look at the entrepreneur landscape, this is one of the biggest problems I see is people don't know who to build stuff for. I like giving to solve a problem that they have, because chances are there. Other people have that problem. But how are you focusing? So you've got 600,000 people now? I think I think you said it best, Which is that, um, Shopify is the software we ourselves were looking for and we kind of scratch around our own itch by building this great piece of software. And I think the reason that he was really meaningful, important to us to help these creators, these small businesses, the entrepreneurs is for a long time they just didn't have the same tools that the big companies were able to afford. Are the big companies were able to get It wasn't affordable, wasn't accessible to them. And in many ways I think the idea was, What if we gave creators and entrepreneurs the same tools the biggest companies use but make it really easy, really simple, scalable and super affordable? Yeah, What would happen? What if we effectively bent the learning curve for entrepreneurs around the world? What would end up happening? And so it was kind of this. It was obvious for us to always focus on the entrepreneurs. And even today, even though we have merchants that are doing, you know, hundreds of millions of dollars a year, our core focuses that long trip enters. And in fact, what's funny is a lot of big companies that use Shopify today. If you ask them why they use Shopify, they'd say, because we need to be a little more entrepreneurial and so they are actually now as opposed to small guys front emulate the big guys. The big guys were actually trying small guys because entrepreneurs now are kind of I kind of figured it out. Yeah, they're doing really amazing stuff. And so that was always really important to us. And actually, the problem, though with small businesses or entrepreneurs, is that there is this risk aversion that some half Yeah, and actually, that's the whole point of the build a business competition. So the story there is way back in, like, 92,010. A mutual friend of ours, Tim Ferriss now and I were talking. And until we were talking and we talked about Shopify where it was going on what was possible, and Tim had this really amazing piece of feedback, which was shoppers. Product is super easy. But most people believe starting a business is either expensive and complicated and that if shopping, I really want to be a company that changes the dynamic and really creates more entrepreneurs. Did that hurdle? You gotta do something. You gotta incentivize that. And the idea was what if we bribe people to start businesses and Tim at this crazy idea that we start this competition where people sort of brandy business on Shopify and the store with the highest sales after six months or eight months would win 100 grand. Great idea. The promise We didn't have money, But the cool part was we figured that if we launched in January 1st, by the time we actually have to pay the winner, which is like, June or August or September, we actually find find 100 grand. We can probably find out over the next over the next six months. And, uh and that wasn't relaunches Build a business competition in 2010 and we'd like 1300 people sign up. And the first winner was gonna call Dodo case at a San Francisco, which makes this beautiful mole skin like I Pakis it was amazing to us was thes air people that may have not started this business if it weren't for this proverbial kick in the butt like start right now and we're gonna incentivize you to do so. And over the course of the next 45 years or so, the build a business competition created tens of thousands of new businesses, and it turned out that giving them 100 grand wasn't good enough anymore because some of them were building multimillion dollar businesses. I don't know if I could go out of my way for that. Okay? Exactly. So we instead did was way said Okay, what if we incentivize them by? Giving the winners is great experience like spending an afternoon with you or spending going Teoh Richard Branson's Island for a week. Necker Island are spending time with these incredible mentors like Seth Godin, Tina Eisenberg and people that we really deeply respect. And on the show, I have that person, every school. So it's it's been this amazing thing ends. Uh, and actually this'll is Take it full circle. One of the winners of the year that you participated was a company called Mgmt Watches movement, movement. Gorgeous, great watches. And Jake and Cramer started this little company in their in their dorm room, signed up for the build a business competition and of being one of the winners. Got to spend some time with you and and actually their little John Exactly. Well, John was was was part of any Littlejohn. Gary Gary Vaynerchuk was there. Tim. Tina Rosenberg? Yeah, that was that was a super fun. It's pretty cool. We actually just saw a Facebook flashback in that whole that whole crew. And actually last week movement sold for $100 million to Nevada, won the largest watch companies, and so that is pretty cool and pretty meaningful, and that was not long enough for them to sell for 100 million. That was just like they just just started, right? But actually, that's what's happening right now is, is these brands the the pace of growth and the trajectory of some of these brands that we're seeing Starting Shopify are unlike anything that the business world has ever seen you talk about, you know, on the front page of Forbes cover of Forbes. Last month it was Kylie Jenner who started a little lipstick company on Shopify and and now has a $1,000,000,000 business. She was 100% by herself. These stories where this entrepreneur are competing with the biggest companies in the planet just really didn't exist 10 2030 years ago and 15 years ago. Even it's right and we're seeing a lot of those today. It's crazy how, how fast it seems to have flipped. All right. So that a lot of nice things to say about Shopify A lot of nice things to say about success. The entrepreneurs have found success. Uh, but let's go the other side, because I think if any anybody out there and the folks at home, they know they've they're largely on their path and they're realizing that Oh, man, this is hard. And so give me a couple would like to say Give me that The first biggest pain point that you had building shop. So let me take actually back before that, um, I talked about a deejay company and I talked about a T shirt company. What I didn't talk about is the 15 companies between, and actually shame on me for not talking with those failures. But actually, shame on us is an entrepreneurial community for not talking about failures. We gravitate to these success stories these sort of tales of incredible, you know, courage and success, and actually think you do a disservice, Teoh aspiring entrepreneurs because we sort of glamorized for sure. And it's kind of bullshit. Yeah, right. And I need to do a better job talking about some of those stories. We talk about Shopify growing so big and having all this merchant, We don't talk about the fact that it was really tough for us to raise any money as this little company and auto a candidate. He was really, I think a lot. And first of all, like, you don't have to do it. A lot of company that you just talked about, how much had, um, had movement watches? Very little. Very well. Yeah, I think so, yes. It sold 400 million raised 500 grand. Total get probably from friends and family was most family. That's right. So, just to be clear, to use Mark Cuban's advice, who is also part of the business? Uh, this the minute you raised money that your first loss because you should build the business or you don't have to raise money. Well, it's a promissory note that eventually gonna pay them back mawr than what you're taking for sure. And for some businesses, you know, if you can if you can rate if you know how to spend. If you don't take a dollar in turn to a dollar 80 and it's just this marketing machine, I can understand why more dollars equal, more dollars that could make sense. But for most of sores on Shopify, they're completely self finance. But there were some really, really tough times for us over the years. And just to be first roadblock, you like, need money. Can't raise money. Well, okay, so let's talk about, like, location. Geography. Okay, I know there's sort of this mean right now that business is become geographic agnostic. That is more true today than ever before, but it is certainly easier to raise since certain place and others. Ottawa, Canada, which is the capital of the country. It's a wonderful place, and we'll all live there. The rest my life. I really love it. It's one of those underrated cities North America, but there's no venture community. There isn't this group of angel investors that have made all this money in a previous startup, that air now paying it forward. There was nothing like that. In fact, it was the opposite. It's it's it's It's like D. C. There's a lot of people there, the work for the government. There is a bit of a risk aversion to it, and I think it was really difficult to convince people that actually, this is a company worth investing in. Did you think about moving? We did, in fact, a couple of investors. In the early days, pretty Silicon Valley investors were making their checks conditional on us moving into the Valley. And by that point, like, you know, we just we liked Ottawa like what was happening. There were families, were there. Was it hard to walk away from money and the check in the Silicon Valley thing? Of course it is because there's this this it's not just the money. It's also the validation that these great iconic investors that right blawg post about whatever I want to invest in you. And you just want you want that validation. And in the inaction, what happened was there was this white paper that came out called the 10 Laws of SAS Businesses, Software Services, our business model. And we basically memorizes white paper because it gave us the nomenclature that even today we're in our business with well, with the front page and on the front page. It said who the author was. There was a partner. Bessemer Venture Partners is in New York City eventually, and through that we just reached out to those to those investors and said, We'd like to talk to you and and come up to Canada and in the end, we actually found a really great investment in there. But I would have my best. Murky at best, your best numbers original. Our first major investor letter, Siri's A. But actually in Hind said, the best thing we ever did was staying in Canada, because in Sing in Ottawa there is something to be said about having a certain focus that I think we wouldn't have had in the Valley. Um, the people that work in Shopify typically work there for a very long time relative to our peers air in Silicon Valley. They have great contacts and stuff, and ultimately, I think it was the right decision. There's something there's something to be said with being the best in your area, and I'm not sure we would ever have been the best company in Silicon Valley just because we're competing with so many others. Yeah, and what you're competing with, it's just crazy. You guys have had insane like on the on par with the Airbnb ease and the Ubers, but but there's a lot of them. Yeah, there's a lot of theirs. So that was one. I would say the other struggle we really had nearly days was recruiting talent. Teoh a place where basically December through March or April, it's really fucking hold. Yes, you can. It's frozen. It's really cold, and we ski and ski has way. Embrace. Which Canadian? It's like it's It's not ice if you can't see fish and it's exactly yeah, So it's it's it's a difficult place to recruit from And it was tough to bring people there, and that's gotten easier over time, but also recurring. And so we did was we said Okay, well, if we can't recruit people that are highly experienced, what if we just bet on potential? What if we brought on people who were super high potential and just spend a disproportionate time coaching them and train them and mentioning them? And in the end, those people that still run Shopify today and so we tried to figure out what we had going for us, which was we had loyalty. We had really smart people that were full of potential. We necessarily have the big rock star names. We didn't have the big veces in town, but we leverage what we did have. And I think ultimately it led to a much more a better company. Long term specific pain points. Raising money was hard at first, but what allowed you to break through? Was it that you you achieve success? You had numbers that were so tantalizing that they couldn't ignore you anymore when you so good that couldn't ignore it. Looks having good numbers again. Metrics Certainly help are certainly help. I would actually say one of the biggest things we did to bring it back. It was built a business. People did not know what Shopify did, who we were. We just We were not a brand people that you shop if I knew who we were. But it was really difficult because we're not a consumer brand. What kind of a brand behind the brand. So many of the stores, all of the shop on our today are powered by shopping without even knowing it. But we just it was tough for us to tell. That story was tough for us to give its people to give us a shot because we weren't just fighting with getting customers first. Need to convince someone to try entrepreneurship, which in itself is really difficult. And then if you're gonna try to try with us and so I think they build a business. Competition was one of the ways where we sort of crossed the chasm from really adopter to the mainstream and island Kurt. And it wasn't gimmicky at this. I don't think it's gimmicky. Didn't really cost that much money in the short run. But just getting people to know we were was really, really challenging. I was probably The third thing was, we were told that our market was not big enough, which in hindsight, is absolute ridiculous because my retail, it's right. But at the time when investors were looking at our company looking the opportunity, ah, lot of them felt that it was e commerce, you know, SAS business model, physical products, sort of. If you kind of just look at the Venn diagram, it just was too small for some. And so when enough people tell you that your market is too small, you begin to believe in yourself, and I think Toby's credit. Actually, he just had the vision that no, like in the future, there's gonna be way more entrepreneurs and were more aspiring entrepreneurs. And we just have to stay, stay focused. But we made it out of those dark days and, yeah, let's talk a little bit more about that. Like the Jeff Bezos quote. As an entrepreneur, you need to be willing to be deeply misunderstood for a very long time. So how does you know, in this case you mentioned, Toby just said No, it's it's good enough and talk to me about win because again, if you're listening or watching right now, so many people are saying, Well, yeah, you know, my parents told me I couldn't do it. My art teacher, you know, during Crit tore me to pieces. I've been had an online Shopify store and I haven't sold anything, and it's been out there for a year like there's a lot of it is very easy to get discouraged. And part of what this show's about is helping people understand people at home that now you have a $15 billion business. But there are plenty of times where people told you sucked you were gonna make it wasn't good enough. Wasn't fast enough. Big enough all those things. So first and foremost like if you love what you're doing and way absolutely did level we were doing it makes a little bit unusual, right? Like our hobby is entrepreneurship. Our business helps entrepreneurs. It was it was easy to stay the course because we actually really enjoyed were doing but to sort of to get a little more specific part of the issue with entrepreneurship is that it's fairly lonely, particularly if your family doesn't believe in you. Your friends don't believe in you investors not giving you money. And so, uh, we were really lucky that Bo Toby I had this great pure birth defect is super cheesy. But we created our own peer group. We called ourselves the Fresh Founders Stupid name, but but it was a group. I love it who every Friday night or so we would go to a coffee shop in Ottawa and we would just commiserating with each other. And actually, in hindsight, that little pure group that we cultivated for for each other was a huge part of the reason why we were able to persevere through all those dark times and so I wouldn't. No matter what city you're in, there is a way for you to cultivate a bit of a community, and I think that's really, really important. The problem is, if you don't seek it out or search for, it's very difficult to find. Yeah, and so Or make a gonna make years. We're gonna make it yourself right. And also there is a con it. Some people don't even want to call themselves artist or call themselves an entrepreneur. And when you don't self identify by, it makes it even more difficult to find like minded people. Yeah, so I would say that that was really, really helpful for us in the early days of figuring out OK, like we need other people that are going to the same thing because otherwise it's just going to be way needed. More optimism, third party optimism in our lives. And one thing that was also helping was we used to go to the Valley probably once 1/4. Maybe even more often to do we would call recharging her batteries. Recharging are big vision batteries, and I would say that you know, if I was in fashion. I'd probably go to Milan or New York City every couple of months to sort of get inspired. If I was creating a car company, I'd probably go to Detroit or wherever to sort of get inspired L. A and the L A. Now, exactly, I do believe that it is really helpful to go and take some get out of your your own way for a little time. And even if its signal buddy's couch in some random city to go and find people, that number one you want emulate number one you want, you want to be like and and that was also really, really be close to the scene. Whenever this right, you don't have to be in it, but you have to tap into, and you can bring that back to wherever you are built my own photography business and creative life out of Seattle, which is neat. That's now. It's a hotbed for entrepreneurship, but it wasn't, you know, 10 15 20 years ago. Yeah, exactly. I mean to Seattle before it was cool. Now I think that that's a really, really salient point that it's true. You don't have to live where every where all of the scene is but connecting with it, understanding what's happening being a part of the culture in the community. And I have a philosophy that I call the other 50% that people think that 50% of your it's making this stuff is 100% of of how you are successful night. No, no, it's it's making it and sharing it. And I'm actually saying, you know, actually, the making it in sharing that's actually only half of the shit, and the other 50% is building community building mentors, building community around the things that you love and these air your first customers easier Beta testers. This is your fresh founders. This is like, if you're not constantly actively building community like you said, Not only is it lonely, but and that's very, very hard for entrepreneurs to sort of break through, and I've found that as well, but it's like there's literally it's your There's no pure group. There's no people to give you feedback because your mom are You know, God bless you, Mom, But Mom does not really know your mentor, right? Your mom can't be your mental, right? So That's the tweet from this. This episode you mentioned about making it and sharing it 11 of the posters we have up in Shopify that isn't just a sign. The weapon we believe is do things and tell people, Um, I think a lot of entrepreneurs spending time doing things but actually tell anyone about it because the fear of judgment or failure, I think in 2018 when the best part of being a creative entrepreneur in 2018 is, I think the cost of failure is right now is close to zero as possible. It won't be zero ever because there's an opportunity cost there for your time, Sure, but when you think about when I think of the greatest stores on Shopify, for example, almost all of them tried three or four different stores before landing on the one that actually worked really, really well on that one. That worked well. Was we better than the other stores as well, that opportunity to sort of to try a bunch of things that wasn't available to our parents or grandparents, but she had to mortgage their entire lives or start a business that may have failed, and I think that that is really, really important. The other piece of it is that I agree, sort of creating. I used to send Atmore emails than I care to remember people just asking for advice. I mean, that's originally how all these mentors from build a business from Richard Branson and Mark Cuban chased Arvis. Like the reason that we got this people. I just actually cold emailed most of you. And I just and I called you and I said, And I got one of you in And so I asked one of you to actually introduce me to another one of you and and I kind of just I outworked everyone else to make developed this thing and and then once one of you agreed, I made sure that your experience was just crest, right? Every aspect of it needed to be fantastic because you guys were then might my tool to get other people to come and do it, and, um and so I think I think it's actually never been more exciting or interesting of a time to be an artist or creator or an entrepreneur than it is right now. I think A lot of the reason is there is less. There's less baggage around it. There's less cost to it. There's more competition, cause a lot of people are trying it now. But there's something really special right now in sort of the way things were happening around entrepreneurs who were starting in their basement and building companies that are beating the crap out of hegemonic Fortune five hundreds. Yeah, which, frankly, I love it. I love it, too, and I think that's part of what you just said. Something. I want to talk for a second. So you listed a bunch of, like, um, attributes, and it's true. It is the best time because of the tools. Because of, um, availability of resource is it's more accepted, its cultural. We don't have the same stigma that our parents, our grandparents, had to go through the morning to the house to get the but the ability to test and learn and poke the audience and say, If they like it or not, it's it's instant. It's like you put something out and, you know, in, you know, 15 minutes if your photographer, if people liked your photograph and that cuts both ways because I think there's a little bit of a short term, potentially a short term win, but a long term loss. How do you use keep people focused on the things that they are supposed to be on this planet to do? And because it is so easy to test to not just run around willy nilly? Because I think there's, I believe, deeply in stamina. Like most successes come right after it is absolutely as dark as it can get. That's when something changes. So how do you in an area where you can build a store and start a business literally tomorrow on Shopify? How do you What? What advice would you give for people not to chase their tail and just do whatever they feel? So, um, I've been thinking about this, this idea of life's work for a long time, that if humans are gonna live longer than ever, what is gonna change? And I think one of the main things that's going to change is that for our for older generations, from my parents and my grandparents and great grandparents, this idea this kinds of life's work was just not accessible to them. You know, my grandfather would say It's very nice that your passion about what you're doing, but I have to put food on the table River and my dad kind of had to put a better roof over my head and a little bit better from the table. But I think, um, college, That's right. Exactly. So eso from you know it's It's a luxury that I get to think about this idea of. Can I do my life's work to write my entire life? I also think that there are so many people who have these hobbies where they go home from their 9 to 5 job, absolutely hates, and they tinker in their workshop in their basement. Or they make a little you know, this cool bracelets at their mom's kitchen table, And I would really encourage everyone that has a hobby to explore the hobby and sort of double click on it just a little bit. I don't mean go quit your job full time because we have responsibilities and and everyone has different things that have to sort of worry about, and frankly, they have to afford. But there is a period, a particular time when we all get this instinct, which is like, all right, I think I'm ready. I think I'm ready to quit my day job. Do thing actually loved doing. And I think that is a really critical juncture, and I think for nothing, it's for everyone. But for send people, I think that's when they actually decide. You know what? This 9 to 5 thing got me here, but it's now time for me to actually do my life's work. One. I think they're to be happier, longer term. But two, I think that I think you could do I think you have a much bigger impact, not just financially, but also when I was I was a lawyer for all of 10 months. I didn't know this. I went to Los. It's very have been friends for longer than five years. I'm gonna call it 10. It's not often, you know, some for years. You don't know that they know where I was a lawyer for all of 10 months and every Sunday night I would get this pit in my stomach because Monday morning was coming and I hated going to work. I hated being a lawyer. I want an entrepreneur and I told my girl from the time is not my wife I said, Um, whatever I do next, I want my Sunday night to feel like my Friday night, and if that happens, I'm good. No matter like that is all I actually want to do. And, um, years since I was 10 years ago, my Sunday night feels like my Friday. My Monday morning feels like my Saturday morning and that, I think, is something really special. I don't think that's unique to me. I think that that's what happens when you find your life's work. And again, not everyone can just quit their job and go pursue whatever that passion is. But there is a point where you have to make that choice and I think if you if you risk it and you mitigate the risks of you, mitigate that, you're not mortgaging your house and and putting your family in a state of peril. But your cat good in that risk. For most of us, that is the right time to jump, and if you do, you get to do really cool shit forever and forever and make money and make people happy and and contribute to the world and fuck. I don't really better than that. And so that is something that I feel very fortunate I can do, and as much as possible, I'm trying help other people find that same thing. All right, let's think about the, uh, a cross section of people that don't have the luxuries that we just talked about. I, um I constantly trying to remind myself that I was born white. I was born male this morning. United States of America. In what? You're what you're but and all of those things gave me a catapult and you were born on third base, born under and still middle lower middle class. I mean, I had upside down Nikes and leaves with four stripes. I didn't know I was clinchers editions. I don't know. I had Nikes with two eyes until I was like, fourth grade. I was like, Wait a minute, My Nikes have up right now anyway. But there is an entire cross section of the world that is, does not have the luxuries that were afforded. Yet there is a new emerging opportunity with put Internet. Plus, I'll just let's talk about Shopify in particular. What are you seeing? Where are markets growing quickly? Onda? What do you feel like it? What's the what is something that we can do to to minimize that gap for that cross section of the world? So I spent some time in the last couple of years. We have a small office in Bangor, in India, and I got a chance to go down there probably five or six years ago. For the first time, I have been going back and was on an annual basis, and what's amazing is 95%. I believe it's 90% of people. Indian people living in India self described themselves as small business owners. There comes the entrepreneurs but small business owners. And so you would think that inherently entrepreneurship would be something baked into the culture. And it is, but in a very different way. And what's interesting is that when we go to places like India, we go to places that are more sort of developing side of the world. What we see is we more creativity because capital is not existence, so they don't have money to spend on AdWords, instagram and Facebook ads. But What they do have is they're willing to just up what everybody else. And I actually think it's that work ethic that has made India, and actually some of these other developing countries just incredible from economy perspective. We've never seen growth like this we're trying to do now is we're trying to make it even easier for them. So, for example, in India there's a credit card. Penetration is just not as high as it is North Korea. So in order for us to be successful there, we have to figure out alternative payment times, whether it's using something like a T M or its cash on delivery. But they're sort of these nuances that we have to work there. But there is one common denominator that everyone, all these countries, wants to improve their life. They want to be. They want to go, works they want. They want to be in a better position than the previous generation. And actually, I think that gives them a ton of advantage over many of us that were born on third base because, I mean, I've been supporting me since I was a kid, and so but I still was born in North America is a white male, but frankly, I didn't necessarily have the same. I don't I didn't need to have the same work ethic of them had. And I think actually that gives them a huge advantage. And it's the reason why we're seeing entrepreneurs of exploding places like China and India and South America now will be interesting is where does North America who frankly is? We're all on third base. Where do we sit next, 10 or 20 years from now? We use, you know, most people North America, working 9 to 55 days a week in China, using special called 96 9 a.m. to 9 p.m. Six days a week. They're willing to outwork other countries, other other people, other cultures. And so my meeting with entrepreneurs there. I'm actually far important spider in many cases than and when I meet entrepreneurs elsewhere because they simply have no choice. And they're just gonna work everyone that is the ones variable that you know you can choose, right? It's how hard you work. That's exactly right. And you don't depend on your relationships or some sort of safety net. You have no choice, and I think that gives them a huge advantage as entrepreneur or even a creator of sorts. Now, I think if the best entrepreneurs I know, no matter where they live, they combine. They take the resource that they have available to them, and they can mind. That was just this this ability to outwork the rest. I was never the smartest person, any my classes on any of the businesses. I just tried to work harder than other people. And this idea of working smart versus working part that wasn't even I didn't I wasn't aware of that. At that point. I was just I was just working hard now, unable to sort of figure out how. How is my time best spent? But I do believe that we're living in a time where you can start a little tea company out of you know, Delhi, and it may be the biggest tea company on the planet in a couple of years, and that was not possible even five or 10 years ago. It's bridge from the opportunities or lack thereof in the emerging markets and talk about trends for a second. So retail is obviously experiencing massive disruption. You know Nikes now they don't have this distribution model. Now Nike is selling their own stuff, and they're they're trying to figure it out. And you look at Apple with today at Apple, completely transformed what it feels like to walk in a store that was trying to sell you something. They're getting training. You just sit down and learn like these air. Completely transformational seismic shifts in retail world. We're here in New York right now, but if you can hear any background noise, but just just again coming in from the airport is like God, there's so much retail, just blocks and blocks, and these everyone has huge flagship stores here. You have to be super tuned in to retail trends because you're in the business of transforming. So would get. Give us a little preview of what's happening, and you talked about physical digital. I'm sure you can cut it on a couple different axes, but just talk to me about what? Where is it going? I think there's a bit of a mean going around like retail struggling retail is dead, and I called emotional that. I think actually this is one of most exciting times of retail since John Wanamaker created Wanamaker's department store in Philly in 1976 18 76. That was the first time where you sort of had a modern retail shop, a bunch of brands and under one roof. It was actually the first store in America Wanamaker's that had electricity and telephone. Wow! And that was at the time, that was super exciting. But I think over the last years or so, you've seen a lot of the same thing, just kind of monetized. You've seen bigger malls, more lights, movie theaters and malls like, but it's been a lot of the same thing and actually think for the first time in in, ah, very long time Now I'm really excited. A retelling. There's some really cool things happening. So one is, um, this idea that a maker can create something and can actually sell it or give it directly to the person that's consuming at the end. Consumer, that is amazing. Yeah, this idea of direct to consumer, I don't believe is a trend. I think that is the way retail always should have been. And the reason it wasn't like that was because distribution was too difficult. Yeah, you lived in a like a shack and Pennsylvania. Exactly. Do you no choice, Right? There is not enough people who live near you to sell your stuff, right? And so your only choice was to go to give it to some large company to fly to bed Bill, Arkansas, and convince a retail buyer Walmart to please put on on their shelves, take a big cut of the margin and probably not going to sell it properly. And the fact today that all of us that create things or curate things can actually go direct to consumer, I think is amazing. So one consumer usually has less money to the maker, makes more money. And three experience is so much better when I buy a boosted board, which is the motor escape word that I ride most days and in the summertime, and I buy from booster board dot com, I get a little chat box that pops up in the right hand corner. I can ask any questions. I want the rains. The weights cannot take it on airplanes and get this amazing information right away. Yeah, but if I went to go buy it at a Best Buy, for example, some sales guy would have no idea what you know the answer to these questions. I think as a consumer director, consumers is so much better. I also think this idea that when I was when I was younger, days ago concerts, for example, if I wanted to support the artist, I was seeing, uh, that's it was a musician. I would go to the merch table merch stand, and I'd buy some crappy gilding T shirt with the tour dates on the back. Where is now? When I go to a concert, I go to a drink show. I see the most amazing winter coat, co branded with drinks brand in Canada Goose and and so that's telling me that I think anyone that has I think a lot of these celebrities are actually creating really great brands that are not promotional brands but truly are away for their fans and the people that care about them to to engage with them on a more deeper level, I think a lot about like, you know, Kylie, right Kylie Kylie Jenner, who's created this $1,000,000,000 brand she owns 100% of it on her own. And she's selling this amazing lipstick on Shopify. I think when I compare her to, like Michael Jordan, for example, who I think created this amazing brands, what with Jordan Brand, but he doesn't actually own it. Nike owns his brand. Yeah, right. And I think of Michael Jordan started today. What you would see is you'd see him opening his brand. You'd see Nike as a supply partner that you have with Kanye, for example, of the Adidas. And so I think one of the other trend that I think is really exciting is seeing more of these people celebrities, artists, wrappers, professional athletes figure out what their brand it is and then create really great products around it, not promotional products, but truly nights. Chachi, he's not. He's but actually great stuff. That's a second thing I'm saying. And probably the third and most important retail training I'm seeing is I think the future retail is just gonna be wherever shoppers want to buy and if you want to sell to you and I. But I have a great online store experience, maybe also have really good physical store experience If you want to sell to my sister, you better be selling something like Snapchat or Instagram Face because that's where she wants to buy. And my mom and dad still love walk into a brick and mortar store. Yeah, I don't believe those air different businesses. I think that's all part of retail. And I think the retailers and the merchants and the makers in the future that are gonna be really successful are gonna have a really deep understanding of what their customers want, how they want to purchase. And so, um, I think that's pretty amazing. I also think the fact that you have these thes niche friends, many of them are on Shopify who are building things that are just amazing and then selling them to the consumer and going back to the example I said earlier and actually taking a big chunk out of these big, emotionless companies and actually beating them at their own game. That's super inspiring. I love that so much. So let's talk about again. It's a little bit about trend, but it's you all see the money that flows through your pipelines and what sectors it comes from, and so a little bit of back story in context for the folks at home. Come. So I had an amazing time as a build a business mentor. Weirding it was myself. Cuban Ferris. Uh, Littlejohn, Gary V Tina Roth Eisenberg Stlead. Ebanks Um, Mr Selim forget it's basically it was basically chasing a bunch of Damon Damon, um, and we each men toward a different sector. So, uh, and we get to, you know, give your money away to them when they won on, then agreed to be their mentor for a year or the year. Six Monsters like that was really cool. And I know relative to some of the other businesses my photography and imaging, the people did not. They made a ton of money, but it wasn't like what some other genre of, uh of maker made. So just talk to us a little bit about like, who's making a lot whose, where they're great margins. And I don't advocate that you build your business on these principles unless you are an MBA who's looking to jump on board and operated company. If you're a creator and a founder at that, you should do something that you love first and foremost, and then hopefully there's some. You can create some good unit economics, but I'm just fascinated to know a little bit about these trends. And I don't want to read your public filings. I want to tell me so a couple things. First of all, I think I think the ones that sort of stand out from your the ones that, as you said, had a deep passion, what they were doing. They weren't selling widgets. They were selling something that they themselves really loved. I would also say a lot of them before they actually went all in, they kind of tiptoed into the water a little bit. So you may have someone that has, like a soccer blawg. Uh, and it's a cool blogging people reading it like, you know, maybe I can sell soccer balls or soccer products. They didn't necessarily go on by 1000 soccer balls and store inventory. They may have started with, you know, a drop shipping business. Let me see whether or not like again, you're not gonna make that much money drop shipping business because the margins are lower. But the experiment to figure out whether or not they have product market fit, and once they did, then they doubled down and said All right side by inventory. I would also say the ones that succeeded and have continued succeed over a very long period of time. Um, there was a real story behind what they were doing and this idea of storytelling as cliche as and it really does work really well because one you're able Teoh, particularly early purchasers of your product in it. Becoming your ambassadors, almost your marketing team. And I think if you don't necessarily have a compelling story and you don't really, you have this narrative of why you've done it and how you've done it. I don't actually works nearly as well. Probably the last thing that I think has been a common threat across all the winners of the business that, frankly, most of the Shopify success stories over time is that they really did fill a gap in the market. The whether it was Debbie Sterling Credit Goldieblox because she felt there were no toys to inspire little girls to become engineers, and she was one of very few female engineers or in her class. Or it's Tina, who before the convention grated tattling because she realized that her daughter, Ella, was coming home with a bunch of crappy temporary tattoos on her arms. And she's like, Why can't there be really nice, like Mama can making better That's right or even Dodo case. You said, like, Why can't I make a beautiful looking I bad case? It almost looks like an artisanal book, and I think that those are some of comment. Beyond that, we have merchants that that cell crazy things like boosted boards, which has a lot of R and D behind it. We also merciful sell one single T shirt and that's all they do, so I don't wouldn't necessarily. There's one particular type. I think actually, today it's It's, uh, in December, just 18 right now, a lot of them rather than spending money on digital ads, front paid adds, A lot of them are actually first finding a community online, whether it's on Reddit or Instagram or some random form, they are evangelizing in existing community in advance, actually going a market with it and so that when they hit that launch button, they already have people that are kind of interested in seeing where they go. And that's again, where capital is no longer the most important ingredient for success. It's really creativity and resourcefulness and in community and getting these people engaged, and it's I mean, it's not easy to do that, but it's not impossible. And it doesn't matter who you are. You're raising well, isn't raising money. And but it doesn't matter where your base of your Based in in Seattle Basin in Bangor, you can create and work with the community and add value to that community. We were talking earlier just about one of my favorite source in shop. We just fashion over his incredible story out of out of out of Los Angeles great entrepreneur Richard. But you know, Richard has been sending free clothing toe up, and coming musicians for his longest fashion over has existed, knowing that at some 0.1 of them may actually become the next big thing, and in this case, it was Cardi B. Yeah, and while everyone else now is trying to get Cardi B engaged in their brand because she's this huge celebrity that she shoes brand, she's loyal to fashion over because fashionable believed in her before anyone else did. And yes, it costs a little bit of money because he sent the free stuff, her free stuff. But that was that. That's really what it takes. I think that is. He did have a lot of money, many connections, but he kind of he was willing to place invests. This is just sad if I satisfies a weird place and I think people's minds out there right now and playing like what I don't think the weirdest thing that people like. We get any weird stories of people like making a ton. And if you probably can't disclose how much they mean Yes, yeah, but is there anybody who's made a ton of money selling someone something totally bizarre? Every now and then, I'll catch like a trend, for example, like, I'll see a fidgets bitter, you know, shopping stuff. We see some of those we're stores. I mean, instant part is on the Internet. Every niche has has, like has an actual mass market. That's sort of the beauty of digital commerce is that it's that again, every Mitch has a mass market, so you may think it's a small Nishi may think it's something that only you and your quirky friends care about. But the crazy part is online. You can actually curate that. Bring these people together and you can take a bunch of, you know, people I care about this small nation actually have a real market for it That I think is really great. I can't think of any anyone's that come to mind. Although, frankly, I've been wearing, uh, something. You're not a weird one, but I've been wearing the chubby. Chubby is the short company. No, I'm wearing those shorts, like all throughout the summer, and they're kind of short shorts kind of thing. I never thought I'd wear shorts that kind of go up to here, but they're amazing. And actually, my parents anniversary a couple two weeks ago and my dad snores horribly and I said, I want to get them something. Help with my dad story, but I think it will help my parents marriage and I got them. It's a Shoppers were called Nora in O R. A. It's this thing that goes on my dad's pillow, and every time he snores, it kind of a justice pillow just a little bit, and I don't like my father sleeping much, but he's not storing anything, so I think my mom super happy. But it's, uh that's that's the cool part of my perspective. Watching these hundreds and 100,000 stores on Shopify is that I know a lot of their origin stories, and all of them had doubting all of them, had insecure it all the more unsure what they were gonna make it. And it's amazing me to watch all of themselves. What's now? I think more than $60 billion worth of worth of products on Shopify. And it's not the's big store. It's the long tail. It's like it's all these hundreds of thousands of stores that well, that's the punchline here. I mean, the fact that you started the business is cool. I respect the hell out of you for building this insane business. But to me, like, what were these air messages for you, for the people who are listening and watching right now like you have to. If you've ever wondered if this stuff is actually happening like you, you are gonna definitely gonna make no money if you don't start a store or you're definitely if you don't go into business. You don't print business cards if you don't may be less relevant now. But if you don't start saying who you are, what you believe in and put it out there for people to participate in, to judge, to collaborate with, to build community around, Certainly nothing is gonna happen. So you have that, like, these air stories of entrepreneurs have put it out there and you don't have to. Not everybody is gonna be a movement watches that sells front. You don't have to be right right up on some of the merchants on our platform. They're just trying to make a living, right? They didn't want to work at some crappy job. Didn't like that where they had no passion. They wanted to find their life's work and the fact that can support themselves in their family. That is amazing and and frankly, like what technology has done. Forget Shopify for second. What tech is done is it truly has reduced the barrier for all of us to at least give our crazy ideas a shot. Yet it's 29 bucks. It's like a couple. Lottie's a month starving. That's right, Yeah, for that same amount of money you could actually see Whether or not you're crazy idea has legs, and I think that is worthwhile. I think it's a worthwhile better take on yourself. Let's we're gonna pivot here. So I'm gonna pivot towards right now. There are people who are trying to build companies and who are not yet to where you are with the company that you built, and they're trying to figure it out. And we were joking earlier when, Whatever. Five or 10 years ago, when we first started hanging out, you had 60 people and I have 4000. Okay, everyone says, like that's choir member. When Creativelive grew from 6 to 80 in months, I was like, Oh my God, this is crazy crazy And it everyone a patch on the back on the outside of the inside was total chaos. And because the person who's only worked here for four weeks is higher in the new person. And how did the core values get passed along? And there's like all kinds of problems with that growing from 62 in a handful of years is bonkers. How do you keep your company culture alive? So there's this, um, here's concept or this. His philosophy is called Dunbar's number 150. So I think effectively, biologically, humans gonna keep 150 names of people in their head at any one given time. And so I knew about that concept. I think Seth Godin writes about this a little bit, but, um, it actually wasn't like 100 to 1 50 That was tough. It was actually, uh, he was almost like going from to 60. That was the most difficult for us. For me? Yeah. And the reason is Shopify is deeply personal for me. It's This is not just my my business and my job. It's my life. It's everything to me. And I really took a lot of pride in knowing everyone at the company, not just knowing about who they were, but knowing with her family was when they were up to your dog's name. Exactly and tell me like I just wanted to other stories and it became really difficult me 60 people. So we sort of created something a couple things in the early days, I think have lasted of scale to 4000. So one is we do an AM a at least once a month, where the entire company can ask any questions they want using their name or anonymously and using a very simple read it stop foot damn boat system. We answer the 1st 10 or 20 questions so it really ill has allowed for. It was like a pressure valve release that whatever people are wondering about, it's a vehicle from task. So there's no sacred cows. There's no, you know, things that, like, if there's some of the people concerned about that, that is really helpful, that's one. The second seconding we've done is the company's structured in a way where we have were highly aligned with loosely coupled. And so what I mean by that is the company as a whole knows what direction we want to go in. Every group knows where they're going, but there's very little. There's little interdependency as possible on other teams, which the result of which is that one team is not blaming another team for not be able to get their work done in the same way that we give our partners AP eyes to build APS and themes and all types of stuff on top of we ourselves use AP eyes inside a shop flight from a technical perspective, but also from a philosophical perspective, which is that one business team can work another business team by effectively using, like, I sort of, um, business a p I. And so that also is really, really helpful. Third is, we've been really clear about our values, and I think a lot of people think your values are your culture is what you put on the wall, and we've always sort of felt that our values or our culture I think you're culture is what people do when there were no one else is looking when no one's looking. What what is your staff, your team? Your employees do when they're left to their own devices. That's what defines your culture. And so we've been. We've overinvestment as much as we possibly can. So much so that now Toby and have an internal podcast called Context. It comes in every two weeks is only for this only for our staff. But all it does is we take one topic and we just talk. We just give the context of the history of it while you made a decision. And so now when New people joined shop a fight, they're able to get up to speed almost like an archaeologist. Super rapidly. They listen to it on to x one point. I don't think I don't They could do that with me and text total, but already speak pretty fast. We also we default open so super. I mean a lot of company talk about transparency. We really do default open. So every quarter we have a board meeting and, uh, well, we tell the board in that meeting, we also submitted entire company. We believe it's really, really important. So we've I don't think we do it perfectly, but we've there's there, some scaffolding, and some there's there's There's a foundation of culture and Shopify that I think has been able to withstand the growth. And actually, now I think what we've what we're left with is a company that with every new hire, the average company, the average of the company actually gets better. So I don't think we have a perfect, but I think we're really honest with each other, honest about what works, what doesn't and we just we mean that we spend time on that stuff. It really matters and putting posters on your wall that says Whatever attitude, bullshit. If that's not what you're living in, if that's not what you are setting an example of, it doesn't matter. So we've talked, you know, it's a lot of our stories. They are designed for you to help us. As creators and entrepreneurs understand what the hundreds of thousands of creators entrepreneurs it on your platform are doing, it's like about you specifically hardly human. Um, with your biggest leadership challenge going from 60 toe 4000 I got a lot, but probably my biggest one is I have been, uh, ive been around here my whole life, and I've become quite accustomed to do everything on my own, not because I'm better, but because for a long time no one really want to help me. Yeah, and so I, you know, with teacher business I was the janitor and the receptionist in the head of sales and the CEO and manufacturing everything because no one else would help me. That transition Teoh letting go and not having to everything not defending myself and not micromanaging that has been super challenging. I'm still not good at it on, and I have been seeing a coach now for basis in ST one when I arrived at Shopify. But that is not the needs to transition. And so one of the concepts that has been really helpful for me on the way is the shop plays the idea of a trust battery. So the metaphor kind of works like this. Everybody that I work with and we all work with. They started about a 50% trust battery, and their goal is to get 100% trust as fast as they can. And the way they get there is by making good decisions in the face of ambiguity. And when they get 200% that's kind of what they want. And that's where you get autonomy. I trust them. They can run on their own autonomously and better for us. Better for me, Better for them, better for the company. And I don't necessarily say you're 88% or 82% but we can kind of figure it directionally how things were going. But the reverse is also true if they make a lot of bad decisions eventually the trust battery does deeply, deeply and like an old cell phone that you have in your drawer. There is a point where the trust batter cannot be charged again. It's just so depleted that no matter how many times you plug it in, it's not going anywhere. And so we're really honest about sort of this trust battery analogy, and I'm really honest about it with my team. And I say Look like this is going to really bad direction You need to know that I'm gonna probably a lot more involved now because this idea of trust but verify is now requiring me to verify a lot more than trusting. And Peter Drucker? Yeah, I think it was Drucker. Couple people started to, but But that has been trust matter. I've never heard that was like the trust. But verify that I think is really important. That's probably my biggest shop. The second challenge they have is come. My job changed the lots. Now Shopify is a multi $1,000,000, publicly traded company with a lot of people, a lot of different stakeholders, and, um, I actually I feel like I do recall for for my job every year, and that is really difficult cause my job gets more and more difficult every single year. And I have actually found it's been Mawr. It's been challenging to find people to learn from a zoo grow and whether it's I don't have that many Peters that are running public companies. Most of my friends were any coming that are private, and so I had to find new mentors and advisers. But it's been challenging to my job. Doesn't get easier over time. I actually find it gets a lot more challenging. I think it's what keeps me interested that keeps it compelling and keeps it being my life's work. Advice for someone who's thinking of starting but is afraid advice for someone who's thinking starting but is afraid, Um, well, first of first and foremost know that all of us are afraid. I'm still afraid I still lose sleep all the time. Uh, because now I actually feel like my God, it was like you needed to get successful. Another team to keep it. You got It was like, you know, now, now actually like like, I better keep doing this and I better get better and I get it. I better get faster and get better. Get smarter. And And I have less of, um, less excuses for why we're not gonna build $100 billion company that affects the lives of millions of entrepreneurs now. So first performance, I think it's important realize that all of us are scared. No one has their shit figured out. Some of us tend to put on a bit of a tougher smile or or or put up this sort of shell on top that makes you feel like, Well, they must have their stuff figured out. And actually, over time, I realized that the best people are actually fairly self aware itself, critical and honest with each other to say. Actually, you know what I'm doing. Um, the second thing I would say is, if you have this idea that you have been toying with for a little while, write it down, and every time you think about it, put a check next to it. And if you think about over the course of a month or two and there are 10 checks next to that that idea give it a try. Don't necessarily go all in. Started a little store, take a weekend stall at a farmer's market, go create something that you know, maybe during take a two day weekend and go and immerse yourself in it. Goto a hackathon or accelerated program for a couple days. But give that idea the respect that it obviously deserves it. It's taken a nomics mindshare, and it only has one check box after two or three or four weeks or months, cross it off and move on from there. But this idea that you're in this constant state of limbo and uncertainty, I think that is the worst thing for an entrepreneur, a creator, not all the time. But sometimes the wrong decision is better than indecision. And it's not always the case, but in the case of trying something, particularly now that the cost of failures is getting to be so low, I don't know. You may just figure out what your life's work is and like that is, that's amazing. It's been so fun watching you remember sitting in a campfire with you and Toby Top in late Tom and you were scheming to build a new widget is something. And then the next time I looked around. You guys were 10 times bigger. The next time I looked around, you were worth a $1,000,000,000. And then you went public. And it's just been so fun to watch you grow this from the grass roots in Canada, about Canada, of all places. And also can't Canadians in general like it's it's tough to kind of celebrate. Success in Canada were very well. What well done, E Yeah, but it just it's just a little bit more modest in a little more low key, but actually really proud that is, holding that that much. So it's, uh, well, thanks for Senate. And actually one of the greatest parts about knowing you chase it and and some of our mutual friends is that surround yourself with other people that are equally as ambitious and equally is positive and getting rid of all the energy vampires and your Frankly, that meant for me getting rid of people that were very close to me family again because they just didn't simply add to what I wanted. And they weren't necessarily making me better, and and they were making me doubt myself in ways that I just couldn't afford. But striding myself with really great positive people who were also on their own journey to find their life's work. That's been that's been really important, too. There's no substitute for that. I'm so happy that show that's it. Signing out for another episode. I'll see you again, hopefully tomorrow.

Ratings and Reviews

Dream Focus Studio

By far the best classes on Creative Live!! Thanks Chase Jarvis for bringing so much greatness to the table for discussion! Just LOVE it!

René Vidal

@ChaseJarvis - love chat with Gabby about hope and the "relentless optimism" you share at the end of Creative Calling. Many thanks. -- René Vidal McKendree Tennis


Excellent interview with thoughtful questions. Thanks!!

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