Harley Finkelstein - Becoming The COO of Shopify & Adapting To The New Economy

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That's more than a present. What is going on, everyone? Casey Adams here. Welcome back to the Rise of the Young podcast. On today's episode, we have the COO of Shopify, Harley Finkelstein, here with us. Harley Finkelstein has been with Shopify for almost 10 years. And on today's episode, we talk about what he's learned from Shopify, how he got involved with Shopify and what they've been doing to adapt to this pandemic and much, much more. So before we get started, I want you to take a moment to share this episode with an entrepreneur who is in the E commerce business. Because this episode will add so much value to not only their life, but but to their business as well. So that being said, thank you so much for listening to today's episode of Rise of the Young. I hope you enjoy. Let's get into the episode. What is going on, everyone? Kasey Adams here. Welcome back to the Rise of the Young podcast. Today I am very excited to announce that we have the COO of Shopify, Harley Finkelstein. Thanks so much for coming on, Harley.

Hey there, Casey. Good to have, good to be on the show. Thanks for inviting me. I was actually thinking, how did we connect here? I'm actually drawing a blank here. Was this cold reach out? How did it happen?

I DMed you on Instagram and I was just like, hey, man, it'd be an absolute honor to have you on the show. And it's funny, all the guests that I've had on my show, it's been through Instagram DMs and that's been my tactic. But yeah, I reached out a couple.

Weeks ago and what's your name on Instagram? It's just Casey.

Casey.

It's funny. So I'm Harley, right. And I wonder if there's actually if one of your unfair advantages besides you being very interesting, is that you actually have Casey because the first name thing is very coveted. Right? Like, I love that I have Harley. I've worked hard to get AD, Harley. I just. And I worked hard to get it. I was early about that. I was just early to get it. But that being said, it's interesting that you're using that because actually, I wonder if that is sort of a virtual. Kind of a virtual flex. Instant credibility.

Yeah, I'm so glad you brought that up because literally that happened. I got my name changed about a week and a half ago. So you're the first person to say that. So I'm glad that you noticed that.

Dude, it worked. It totally worked. I didn't think about this situation, but in most situations you sort of think, man, someone had to work really hard to get their first name on Instagram. Either they hustled someone inside of Instagram or they have a connection or they knew someone, or they convinced someone to transfer the name. So that's neat, man. Good for you.

I appreciate you bringing it up, man. It was like a three year process of connecting with the guy. But yeah, man, I'm super excited about this, man. Obviously, I'm a huge advocate and fan of Shopify. All my good friends and people that have been on the show, such as Iconic that we were talking about, Shopify is not only a massive company, but you guys have truly changed the landscape of E commerce over the last decade. And I know that you guys had a huge announcement the last couple of days with rolling out, you know, new features and just everything happening with this pandemic. But I want to ask you, Harley, when did you get involved with Shopify? And how did Shopify come into your life?

Yeah, that's cool. It's a great question and I think it's a cool story. Hopefully you and your listeners do too. So I was born in Montreal in Canada, and I grew up when I was really young, we moved down to the states, to South Florida. And then when I was 17 years old, it was time to go to college. And because I was born in Canada, going to university up in the north was actually very inexpensive. My parents didn't have a lot of money and so their ability to afford a US University was basically out of the question. But because I was born in Canada, I was effectively given this equivalent of like in state tuition. And so I moved up to Montreal to go to McGill in 2001.

And.

2001, obviously 9, 11 happens. Stock market crashes. My parents lose whatever they didn't have very much. Whatever they did have, they lose. And so I was immediately thrown into this dilemma or this decision, which was either I move back down to South Florida, live with my parents or I stay in Montreal and fend for myself. And obviously if you've ever been to Montreal or any listeners have been to Montreal, you know how incredible it is there. It's a wonderful, wonderful place. And being separate, 17 years old there is, it's kind of a fun, fun thing to do. So I tried my head at a bunch of different jobs, things like selling, you know, being a travel agent I had, I was DJing nights and weekends to kind of pay the bills, but it wasn't really paying the bills the way it needed to. And anything that I. That allowed me to make more money unfortunately also came with a much longer time commitment. So I couldn't also go to school. I would have to sort of extend my four year undergrad to six years or I'd have to do part time courses. And I didn't want to do that. I was kind of always been in a rush. I want to kind of get undergrad done. So I ended up starting a business thinking that hey, maybe that's a really good way for me to supplement my income, make some money while going to school. And started the T shirt business, made T shirts for universities. So any of you listening? If you went to school and on the first day of school you got a T shirt, a bag and a hat, kind of a promotional product. My little business made that for about half the universities in Canada and worked really hard. Very small operation, but we ended up building a really nice business. By 2004 or so I was finishing undergrad and a mentor of mine told me that my T shirt business was effectively bullshit. I don't know if I can say that on the show, but it wasn't that. It did not have any unfair advantage, it had no moat around it, it had no the bar to entry for other competitors to do what I was doing was very, very low. So anyone can compete with me. And he had actually convinced me that to be a better entrepreneur I should consider going to law school. And he happened to be teaching law at the University of Ottawa, which is the capital of Canada. And he said, hey, why don't you move to Ottawa, go to law school here, become a better entrepreneur. I'm teaching there. And So I was 21, I didn't know very much. I made a little bit of money with T shirts, but beyond that was quite green as an entrepreneur. So I moved to Ottawa 2005, had no friends, no family, didn't know anyone in the city except this one, this one mentor, his name is Phil. And I Decided that I wanted to make some friends. And so I started asking around, hey, where do all the entrepreneurs hang out? And there was sort of an entrepreneurial organization in town that said, well, there's a bunch of entrepreneurs that hang out at this local coffee shop every Friday night. And so I showed up at the coffee shop and I met four or five entrepreneurs. And one of those entrepreneurs was Toby, and he's the founder of Shopify. And he was just transitioning from. He'd moved to Canada a couple years earlier from Germany, and he was just transitioning at that point from having a snowboard business to having a software business. And the story very quickly is that he wants to sell snowboards online to make some money, didn't find good software, wrote a piece of software to sell his own snowboards, and then people began asking him if they can use his software to sell their own products. And so that's sort of when I met him. And he explained to me what the software did, and. And that was sort of the early iterations of Shopify. And I thought, oh, this is a really cool thing. Maybe I can migrate from being a wholesale B2B T shirt business to being a retail B2C T shirt business. Which was awesome because it meant that I was able to finish law school in the right time. But while I was in class, the business was able to run concurrently and virtually. And so I became one of Shopify's first merchants in 2006, I guess, and then finished law school, went to business school. I did sort of this joint law MBA thing and went to go practice law as a. As a very young junior lawyer in Toronto. This is 2009, and, man, I hated it. I thought it was like the worst thing in the world. Whereas entrepreneurship was all about meritocracy and all was about, it doesn't matter who you are and what your last name is or how old you are. It's about your impact, your value creation. The legal profession seemed to be the exact opposite of that, and I just hated it. And so I called Toby in 2009 and said, hey, I'm done with being a lawyer, but I love what you do with Shopify. I love my own experience. I love the fact that I was able to create independence for myself. I was able to build a real business sitting in tax law class in three hours that would go on to compete with Walmart and some of the big retailers that sold T shirts. And so later on that year, I moved from Toronto back to Ottawa and became really one of the first sort of business people, non engineers at Shopify. And that was about. That was about 10 years ago, about a decade ago. And it's been the ride of a lifetime.

Absolutely. So Shopify back in 2009, what was it back then? A couple thousand merchants were on it. Because when you first connected with Toby, just where was it during that time? And when you got involved, what was the vision? Because like I said when we started the show, you guys have changed the way e commerce businesses run. So going back to the blueprint of Shopify, what were you guys doing back in 2009 because you guys saw something so massive before a lot of other companies and completely changed an industry. So I'd love for you to take us back to that moment where you came on board as the first businessman that's not the developer. Just take us back to 2009.

Yeah, so I think around that time we had maybe a thousand or a couple thousand merchants. But let me zoom out for a second. At a macro level. In the mid 2000s, if you want to sell a product on the Internet, you had two options. Option one was you would go and pay something in the neighborhood of a couple million dollars to have Hybris or ATG or demandware or. Or Magento, someone build you some iteration, some version of that. And that was really expensive, very complicated, not very flexible. So that was option one. So if you didn't have the money, the capital, there's no way you can take down that option. The second option was you can cross sell on a marketplace like ebay, for example, which although it was not expensive, you were effectively renting customers from that marketplace, which meant that you did not have a direct relationship. It was not direct to consumer. There was an intermediary who was effectively brokering or leasing you their customers at a premium. There's a fee for that. So that was the landscape. So the idea that we were able to have, and Toby's able to build a product that gave people the scalability and the functionality of some of the enterprise platforms, but were cost effective and affordable in the way that ebay was or some of the other marketplaces were, that was very, very disruptive. And then on top of that, another layer, Toby was one of the Ruby core members. So part of the group that really got Ruby on Rails going. And it was like Shopify using it at the time. It was 37 signals using it. And I think Twitter at the time was using it as well as sort of the first software company, SaaS, companies that were being built on this coding language. So a lot of the early customers and merchants on Shopify were sort of these Ruby on Rail fans, these people that were kind of in the Ruby on Rail community. And I think that gave us a little bit of an early start. And then when I got there, you know, it was very specific. It was E commerce only for only small businesses that were new businesses in a very limited geography, effectively the United States. And at the time, you know, if you wanted to sell a product online, a lot of people were still going the ebay route. A lot of people that were big companies, the Walmart or the Best Buys were still going on the enterprise route. But I think we were focused and I think we were disciplined about saying we think we can do this better. At that point, we were not cross channel. It was just E commerce. There was no physical commerce at that time. It was focused on really, really small businesses. But I think we were thoughtful about things. One example of that is this is something that anyone that's building a software company listening should think about is when you're building software, you can build software in sort of one of two ways. You can either say, I'm going to be everything to everyone, or I'm going to be very selective about who I'm working with. And in the case of Shopify, we said, we're going to build a piece of software that most people need most of the time. And for anything that goes beyond that definition, any features or functionality, we're going to build a set of APIs and let third parties build on top of our APIs. And this way, if Shopify gives you 80% or 85% of exactly what you need, that additional 15%, which is very specific to your business that other business may not need, you can go to the App Store and you can download and install these apps to get more functionality. It meant that we didn't have to build everything ourselves. But everyone using Shopify then and today has 100% product market fit for what they need because of these extensions. And that's kind of what things looked like. Then we began to build up the app program, the theme store, the referral program, and those were exciting days. I think we were probably eight to 12 people at that point, maybe a couple more than that. But it was fun.

Absolutely. I just saw your Instagram post about how five years ago you guys went public, correct?

Yesterday to the day. Yeah, yesterday. Five years ago yesterday, we were standing on stage at the New York Stock Exchange ringing the bell, which for an entrepreneur is it's like Mecca. It's such a wonderful experience. That's when you look down, you see I have two daughters now and. But my. So we didn't have kids at that point. But my wife was there and Toby's wife was there and his kids were there. And it's just our investors were there. The people that first believed us, Tim Ferriss was there. Like people that never. That really believed in us before anyone else that never doubted us for a second, they were there supporting us. And that was a very special moment.

Very cool, man. Do you remember just like, because the journey from, you know, I just want, we're jumping around but 2009, you guys are just getting started to going public five years ago to now, 10 to today. I mean you guys, like I said, have changed the landscape of E commerce. And I want to touch on just over the last two, three months with what's been happening with this pandemic. I know that you guys have been making a lot of changes, but I'd love to ask you how have you guys been able to adapt during a time like this? And what have you guys learned through this pandemic?

Yeah, I'll take the second part first. Cause it's easier. What I have learned and I think what we have learned as a company, which is also incredibly inspiring, is that fundamentally entrepreneurs are some of the most resilient humans on the planet. That adaptability, that perseverance, that the idea of a pivot is so baked into the entrepreneurial DNA that there is no making light of what is happening here. It is a bad situation. 40 million Americans are unemployed right now. And that's just in one country. But there's this resiliency and this adaptability that has really been inspiring. We're watching entrepreneurs become very resilient. We're watching restaurateurs who don't can't have anyone in the restaurant turn into wine shops. And we're watching kombucha online stores turn into farmers market, online farmers markets. We're watching grocery stores do this whole cash in, you know, this meal kit sort of thing. We're watching stores like, you know, I did, I did an interview with one of my favorite brands on Shopley, Birdwell, which makes these iconic surf shorts. I mean 50 year old company that now are making masks. And so we've learned that entrepreneurs are adaptable. But it's also been incredibly inspiring in terms of the first part, what we have done. Within a week of the crisis hitting, we called for hack days across the whole company. We said everyone stop what they're doing, let's figure out what we can do over the next three days whereby we can temporarily lower the minimum bar, but ship fast. Ship products very quickly in a way that helps some businesses survive. So even if it's not exactly as polished as we typically would like, that is okay right now because the MO Is help entrepreneurs and small business survive. So we called this hack days, and out of that, we got curbside delivery and local pickup for anyone using Shopify point of sale in a physical location. We got gift cards out for everyone. So if you're a barber shop or you're a hair salon or you're a cafe or you're a yoga studio, who doesn't have a physical product to sell? Now you can set up a store, Shopify, and easily sell these gift cards and get cash flow in immediately so you can pay your bills and then your, you know, your most loyal customers can go ahead and. And they can redeem at a later time. So we got this stuff out there very, very quickly, and that's sort of what week one looked like, and then week two and week three sort of like, okay, what now needs to be high quality bar, but we should reallocate resources to make sure it goes out quickly. So Shopify email felt very important. The new Shopify point of sale felt very important. The shop app felt very important because it not just allows you as a consumer to track all your packages, but now you can discover other local businesses. And so that's kind of how we've been operating since the crisis hit is operate under the assumption that products that we put out now, maybe if they're good products and they have been good and they continue to be good products, that they may be the difference between an entrepreneur or small business surviving and not surviving. And so we very much are. It feels a little bit like our mission to make commerce better for everyone, to spread entrepreneurship, to support small businesses. Feels like it's never been more important than it is right now at this very moment.

Absolutely no 100%. What would you say? Just, you know, people that are out there listening to this podcast, you're someone that understands building team culture, right? You guys, going from 2009 to going public to where you guys are today, you guys have scaled in such a, such a big way. How have you guys at Shopify been able to keep the culture dialed in, really just build leadership within the company? Because I think that's what, you know, a lot of young entrepreneurs that are listening, that's something they may struggle with. Where it's like building teams and building culture and building community within their organization. So how have you guys at Shopify been able to do that so effectively?

Yeah, well, a couple things. First of all, I think a lot of companies get culture wrong because they sort of set culture and they're like, this is it. And everyone that comes on needs to adopt this culture. We don't believe that. I don't believe that. I don't think our company believes that. I think culture is dynamic. It's evolving. It should evolve. It's a living thing. And with every new person that comes to the company, the culture should change. In some cases slightly, in other cases in a much more meaningful way. That's a good thing. If you hire really well and the culture evolves into something better than it once was, better than maybe anything you ever anticipated, that's a win. So that's one aspect. The second aspect is culture is not. I love your posters. I told you that when we got on the call behind you. And I love the folks that are doing great, beautiful visuals for offices, home offices, especially right now. But culture is not like putting something on the wall that says leadership with an eagle on it. Culture is what people do when no one is watching. How do they act? What happens when someone is left on their own to make the right decision? Do they do that? And that, to me, is what culture is. And so we cultivate that. So one of the things we've changed certainly during the crisis is we've always been a default to open company. We've always been a company that did a lot of AMAs, a lot of town halls, but we were doing it out every single week. Every Friday, myself and a few of us, we jump on a hangout, we'd do an ama, we talk to the company, we share what we learned that week or we learned that day. It feels like the cadence now of communication is happening, like hyper real time. And so having monthly AMAs or monthly town halls, that just doesn't do the trick right now. We've had to modify that based on what we are seeing happening in the world. And that's been really, really helpful. But in terms of the leadership thing, there's this great anecdote, sort of. It may actually not even be a real thing, but I've always enjoyed this story, which is some university was building a new campus, and someone asked, some architects said, hey, where should we put the paths between all the different buildings? And someone else said, well, don't put paths anywhere. Leave it to grass. Wait a few weeks or a few months and see where the grass is missing, see where organically and naturally and authentically people want, what paths they want to take. And then where the grass is missing, that's probably the right place to put the cement or put down those walkways. I think leadership can be like that sometimes, especially in a startup where you can tell someone, hey, you're in charge. Or you can just carefully watch in a very thoughtful way who's picking up the ball, who is already doing it, who is creating those paths, who is finding new areas of the business and problems to fix. And then you promote those people. It doesn't matter how long they've been around or what their experience is or how old they are. You promote the people that have the impact, the people that say, I see a problem, I'm gonna fix this right now. And that I think is probably one of the most important ways to build a really strong team.

I love that. That's a very in depth, quality answer. I appreciate it. Something I want to touch on is if you were to give a piece of advice to somebody launching a Shopify store today for the first time, what would you tell them?

So when I launched my Shopify store in 2006, whenever that was one of those first stores, I remember thinking that the most important thing I'm going to need is going to be capital because I can build a beautiful store. I have access to great shirts because I had a bit of a. I had some experience in the T shirt industry, but I realized that the problem that I was going to face was how do I get people to my store? And capital was the main ingredient. So every single penny that I had, I spent on marketing, digital marketing, and on inventory. Today I'm not sure I would worry the same way about marketing today. I would say that creativity is probably a lot more important than capital. What I mean by that is I don't know if you know Ben Francis from Gymshark, one of my favorite stores. Ben's a good friend of mine, someone I spent a lot of time with talking about entrepreneurship and retail and e commerce. Gymshark, one of the greatest success stories on the planet from DTC brand perspective, with sales in the tens or hundreds of millions of dollars, just incredible company. Their business was built on content, creating quality content, giving it away for free, not paying big influencers. And they may do that now. But at the beginning it was just finding people that already had a following and just connecting with these people, like sort of dot connecting. And Ben also tried a bunch of other Things that didn't necessarily work as well, but he tried enough things to be like, I think I'm gonna try three things or five things. I'm measure which one works best and then I'm double down on that stuff. Also, I think if you were starting an E commerce business or any business in 2020, figure out who your total addressable market is, your audience, and figure out where they're hanging out. And they're hanging out on Twitter, spend more time on Twitter, they're hanging out on Reddit. That's where you spend more time. They're hanging on TikTok. You should be. That's where you should be putting. That's where you should be spending your time and your energy. But what you should not be doing is simply trying to. Don't be lazy, don't think, well, no one cares about my store. No one's coming here. It must be because I'm not spending enough money on Facebook ads or Instagram. No, it's because you actually don't. Either you don't know who your target audience is or you do and you haven't actually found where they hang out. And I think what's neat about building a business in 2020 is the cost of failure is trending towards zero right now. Never been less expensive now to build a business. And you don't need a lot of capital again, you just need a lot of creativity. You need to figure out who you're selling to, where they're hanging out. And you have figure out a way to get in front of them and engage them. And so I would say that it's really, really important more than ever now to know who you're selling to and know the behavioral trends of that demographic. And I think everything else kind of works itself out after that. Yes, you probably need better supply chain management. Maybe you need a better deal. You can work all that stuff out too. But if you have a product and an audience that people like and you can connect supply and you can connect demand on that, then you get some momentum of this flywheel. And once the flywheel starts going, it needs kicks. And so you kick it with a couple different campaigns and a couple different promotions, and you kick it with a couple different deals, and you kick it with talking about it on different podcasts, and you talk, you get that flywheel spinning and then eventually get some momentum and some real traction. And that's when you can get through the really cool stuff. That's when you get to go big and build the next gymshark or Kylie Cosmetics or Allbirds or Fashion Nova or. I saw Jeffree Star just launched his new Flash sale on Shopify about an hour ago. I think he sold out within, like, 20 minutes and probably sold more than Sephora did all week. He did in 20 minutes. But to use Jeffree Star as an example, Jeffrey started is doing these incredible YouTube videos, doing makeup tutorials, figured out who his audience was, where they spend their time, and what is considered and defined as value to them. And he just gave them a ton of value. And then he said, hey, if you like my videos, I'm actually creating my own line of makeup. And so here's a connection. I'm gonna connect the audience that I already have with a product that I'm about to build. And I think that's those stories, they're all gonna be Jeffree Stars. But there's a lot. Like, there's more than a million success stories on Shopify. I think that's really cool.

Absolutely not. I love that. And I know Rich from Fashion Nova, they absolutely crush it. And I wanted to touch on, you know, these. Because there's so much massive brands that are on Shopify that you just mentioned, whether that's Cali Cosmetics or Fashion Nova to anything from us. You know, someone that's doing one sale a day and that blows their mind, and they're, you know, getting their business off the ground. You guys have made the playing field. You know, anything from a individual who's starting a very small business to a massive brand. So I want to ask you, just Moving forward into 2020, what are you excited about when it comes to these different verticals of businesses? Anything from the small business to the massive businesses? What are you excited about personally? And what should people expect from Shopify moving into 2020?

So, I mean, I talked about this in the earnings call last week. We had our Q1 earnings. It is really cool to me that a brand like Heinz, Heinz ketchup, which is 150-year-old brand, decided during this crisis, we got to have an online store and go direct to consumer with our condiments, ketchup, mustard, relish, whatever the stuff is. And within five days or seven days I think it was, they signed up for Shopify and they launched their store. That's a really cool story. Lindt Chocolate did the same thing. A bunch of Procter Gamble companies and Unilever companies. And I love that. I think that's really neat. But what I love the most is those stories of entrepreneurs who start at their mom's kitchen table or who Start in class because they're bored like I was or something like that, and then turn out to be category leaders. And that is the Allbird story, and that is the Gymshark story, and that's the Fashion Nova story, and that's the Bomba story, and that's even, to some extent, Kylie story. These are brands that started from nothing and have become complete, that have completely challenged these industries. And they don't necessarily resemble the incumbents of even five or 10 years ago. That feels like business and entrepreneurship and retail is becoming democratized. That's what we're like. That is it. That's the leveling of the playing field that Jake and Kramer can start movement in 2013. Those guys. Yeah, those are great guys. So, I mean, I've known them since day one. Start in their dorm room MVMT watches, and a couple years later they get acquired for over $100 million by Movado. Why did they get acquired? They haven't said this, but I can say this because Movado needs a really great direct to consumer brand. And they cannot create the authenticity the brand and frankly, just the energy that movement created for the market. And so they acquire them. Those are the stories that I. Those are the most meaningful stories to me because that means that entrepreneurship is different today than it ever was before. That entrepreneurship is not just a toy. It actually allows you to build the largest, most important companies on the planet. So what am I most excited about? More of those stories, Those homegrown success stories. I love the fact that we have Staples and I love the fact that we have these big, you know, big massive companies. Budweiser and, you know, companies that are, you know, P and G, Unilever, like PepsiCo, like these hegemonic companies.

I love.

They're using Shopify because it shows the scalability of the platform. But the ones that I, you know, smile to myself when I'm going to bed at night about are the ones that are these homegrown success stories. And I think that is. There's nothing for me cooler in the world than those stories. Yeah, what I'm really excited about from what's coming is we started with E commerce, and then we realized that the future retail is going to be retail everywhere. So the retailers that are going to be successful will need to sell online, offline, on Instagram, Facebook, on Amazon, ebay, on every possible channel out there. But it all feeds back into one centralized place, which is the Shopify admin. And that is one place to go to run your business. Your retail Operating system is sort of what I've been. The term that I've been using. So we have this thing you can sell anywhere. And then a couple years ago we realized something, which is that, okay, there are other things, other solutions, other tools that entrepreneurs and small business and even big businesses need as well, where if they themselves try to get it, they would not necessarily be competitive with the largest retailers on the planet. So let's say shipping costs, if you go to USPS or you go to Canada Post or Royal Mail or FedEx, as a small business, you were to say, hey, I need some, I need pricing on shipping labels. You'll get pricing, but the pricing is going to be effectively 100% retail rates. Well, what if I went on your behalf or anyone, Shopify went. What if we went and said, hey, think of us as, think of us as one retailer. And actually, if we were one retailer, if we were one single brand or one single store, we would be the second largest online retailer in America. Amazon would be first, Shopify would be second, and then after below us in aggregate would be Best Buy and Walmart and Target. So what if we went across all those different categories of the things merchants need, entrepreneurs need, but on their own, they would not be able to get access to them. Not at the pricing, not at the levels that we can get together. And so we began to build out all these merchant solutions. And again, we announced balance just a couple days ago, which is this way for merchants to monitor the entirety of their financial world. Whether it's the sales, their expenses, give them a card they can take out cash or they can spend on with a real thoughtful rewards program. It doesn't give them discounts on stuff they don't need, but rather give them discounts on things like marketing and shipping services and things like that. What would happen? And so what I'm most excited about is not just the fact that we have this retail operating system to allow and enable merchants sell anywhere, but the fact that we are going step by step and checking off all the things that every entrepreneur, every merchant needs and giving it to them in a way that allows them to compete with the biggest companies in the world. That to me, is the leveling of the playing field. That to me is why I get up every morning, why I've committed my life to Shopify and to helping entrepreneurs. Because I do think once we level the playing field, the rebels we've been talking about, army and the rebels, the rebels are going to win, and the rebels are the entrepreneurs. And I can see no Higher calling than that in the world, at least for me.

Yep, I love that. I have two more quick questions before we wrap up. Harley and I know that you guys had that big announcement with Shopify Reunite 2020. And speaking about just two entrepreneurs and empowering entrepreneurs, there's a lot of young entrepreneurs that listen to this show and I'm 19 myself. A lot of 18 to 25 year olds that are out there starting their businesses today. If you were to go back in time and give yourself one piece of advice, after all the experience you have of, you know, growing with Shopify, what would you tell yourself and why?

I think one of the best, most important lessons that I've learned is to get really, really comfortable with being uncomfortable. I really struggled with that partially because my upbringing was I didn't ever feel a lot of financial security growing up. Certainly when I was 17, I was, you know, supporting myself and my mom and sisters. My dad wasn't around then. That was really, really difficult. So I never felt real security. And so I was always seeking security as much as possible. Actually, one of the reasons I went to law school, I haven't really admitted this very, very publicly before, but I will say one of the reasons went to law school was not just to become a better entrepreneur, but I think I was looking for a bit of a security around, oh, now I have a profession. I'm a lawyer. Isn't that cool?

Yeah.

But what I've realized, I turned. I'm 36 now. And what I've realized is the magic happens when you get out of that comfort zone, when you do get comfortable with being uncomfortable. And actually it's a muscle, you have to put yourself in those situations, whether it's someone who's not technical, learning, you know, learning how to code, or whether it's someone who's not great at running or athletics, learning how to run, or whether it's someone who isn't great at languages, learning a new language, all those things. Like, I started running last year because I realized that I needed a way to manage my own anxiety. I've always had really high anxiety. Meditation has been incredibly helpful coaching as well. But I needed something else and running has been really helpful. Am I ever going to run a marathon or like win a marathon? Probably not. But I really like the idea of training as if I were, because it makes me so damn uncomfortable. And the challenging of trying to run at a particular pace, it's like working out that uncomfortable muscle. And I really wish at an earlier point I would have become more comfortable Being uncomfortable, that'd be the first thing. The second thing I would say is I felt that in hindsight, I felt I was really insecure when I was 17 and 18. I've always been sort of. I'm fairly short. I've always been kind of the shortest kid in my group of friends in my classes. And for some reason that always. It didn't bother me per se, but I think there was something about it that made me a bit insecure. And one of the things I think I've learned over the years is that I think with that insecurity, what it led to was I was intimidated by surrounding myself with people that are so much better than me. I don't think you have this problem because part of your life is bringing on people that you like onto your show and talking to really interesting people around the world. But I now surround myself with people, friends, mentors, peers, people that I work with that are better, smarter, faster than me. In fact, probably unequivocal. All of them are. And I don't know, that's a really wonderful thing that's made me a better human. It's made me a better father, better husband, a better leader, a better entrepreneur. But a lot of us want to resist that because it feels a little bit like it makes us feel worse by being around someone who's better than us. And that's not the case. That's just our self speak, our self doubt. And I think if you can create a dynamic, whether it's at work or at school or at home with your peer group, even if it's in a remote way, like we are right now, working from home, create a group of people that you truly admire, that every time you speak to them, you're just like, wow, like, they are better than me. And that's okay because they're going to make me better. That's been really helpful to me.

Love that. Last question before I let you go, Harley. I know that early on in this podcast you talked about, you know, running into Toby at the coffee shop and the value of networking with entrepreneurs. That's been a value of mine that I've tried to pursue since I was 16. Over the last four years of, you know, talking to high quality people. Can you talk to me about the value of networking in your life? Because I know we're talking about all these stories and we were talking about the mutual friends we have. Just how have you been able to build such a high quality network in your life? And what has been the value of networking and just what does it mean to you?

My mother uses this term. It's sort of a Jewish, Yiddish term called chutzpah. I don't know if you know the term. Basically, that's how what I've always had, it's. It's. Chutzpah can be defined as audacity. I am okay with sending out a hundred emails even today. And if 99 people don't respond to me but one does tomorrow, I'm still gonna send out a hundred emails.

Yep.

And there's work involved in that. I need to figure out of those hundred people, what can I do for each of them? Because they're busy, they have thoughts going on. They have a lot. You know, they have their own stuff they're trying to do. What can I offer them that is of value to them? And the reason we've built this network. We talked about some of the people that we brought into Shopify for the build a business competition in the early days. People like Gary Vaynerchuk or Tim Ferriss or Seth Godin or Richard Branson. The way that we connected with them then. The way that I connected with them then when no one knew Shopify was, I found something that was valuable to them, and I made the opportunity for them to engage with us either equally as beneficial for them as it was for us, or even more so, more beneficial for them than it was for us. And that has been really, really helpful. And then when the build the business competition was over and we didn't need them anymore, I still tried to deliver value to them. And what happens is, over time, if you have this audacity or you have what my mother would call this chutzpah, and you're putting yourself out there and you're adding value and you're giving people things and not asking anything in return, you actually end up with people that genuinely like you. And when people like you, they're willing to. They want to help you. And that's just been a huge part of my life. I have always had been. I'm sort of religious about mentorship. Meaning even when I got married, 2013, I called the three or four people that I felt may not be great entrepreneurs, may not be even great, you know, at anything, but they were great partners, great spouses, great husbands. And I said, look, I'm about to get married. I want to know if everything you know about being a great spouse, same thing with parenting. What are the books that they were reading? How do you be a great dad? I wanted to. You know, I wanted to Be a great father. So I've used these mentors and advisors in a really critical way. And sometimes you outgrow some of these mentors and you grad students, advisors, sometimes you outgrow people in your life. But generally, I think if you have the audacity and you know what they're into, I mean, again, I wish I can almost reread the message you sent to me to get on this podcast, but it must have been something around helping entrepreneurs, something around talking to entrepreneurs in their late teens, early 20s, something like that. And I'm like, of course I'm gonna do that, because when I was that age, I would have loved to know what I now know now. And if I can disseminate all that for everyone listening, fuck, that's cool. And yes, I should do that. So I think that's really, really important. And by the way, I actually think that with us moving away from more sort of in person, proximity type social environments where you gotta be in Silicon Valley to meet the right people or you gotta be in New York City, that I think that's over. I think it's been over for a while. But Covid has really, you know, put this, put the stamp on that. I think now you can be anywhere in the world and you can create the most incredible network without ever leaving your home or leaving your town. That also feels democratizing.

Absolutely. Well, Harley, I just want to say thank you so much for coming on this show today, man. It's been such a pleasure. Where is the best place for the listeners to follow you and stay up to date with everything you have going on in your personal life? But also at Shopify.

Yeah. I mean, obviously on Instagram, Arley. As we talked about on Twitter, arleyF. I, I wasn't able to get a Harley in that. That's usually where I spend most of my time, publicly and socially and otherwise. If you're thinking about starting a business or you're trying to pivot your business or expand it, or adapt your business to this new climate, check out Shopify. I think it's a wonderful product and it's a great way for you to accomplish what may become your life's word.

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