Harley Finkelstein joined Shopify in 2010. Originally as a merchant selling t-shirts on the platform. Today he serves as President of the company and his passion for entrepreneurship is as alive as ever. As president of Shopify, Harley's life mission is to empower as many entrepreneurs as he can and remove every barrier to entrepreneurship possible.
What exactly does Harley do on an average day at the office? What are the big challenges Shopify is working on now, and what's in store for Shopify in the future?
In this episode we dive into all that, and more!
Harley Finkelstein is an entrepreneur, lawyer, and the President of Shopify. He founded his first company at age 17 while a student at McGill. Harley completed his law degree as well as his MBA at the University of Ottawa, where he co-founded the JD/MBA Student Society and the Canadian MBA Oath. Harley is an Advisor to Felicis Ventures, and one of the “Dragons” on CBC’s Next Gen Den. Recently, he received the Canadian Angel Investor of the Year Award, Canada’s Top 40 Under 40 Award, and was inducted into the Order of Ottawa. From 2014 to 2017 Harley was on the Board of the C100, and from 2017 to 2020 he was on to the Board of Directors of the Canadian Broadcasting Corporation (CBC). Harley is currently starring on Discovery Channel’s I Quit, a television series about hopeful entrepreneurs who decide to quit their 9-5 jobs to focus full-time on their side hustles.
Jay: Harley, thank you so much for coming on the podcast, man. It’s really good to have you here.
Jay: Harley, thank you so much for coming on the podcast, man. It’s really good to have you here.
Harley: Hey, Jay, it’s a real honor and a pleasure for me to be on. Our history goes back a very long time, so it’s really cool to think about where we started together on this journey as partners and where we’re at today. It’s amazing, and, I have to say, I know it’s your podcast and you’re going to lead the conversation, but let me just take a moment to say how incredibly proud we all are of what you and your partners have built at Bold, and just, Bold to me is this huge success story that in many ways has followed the Shopify success story. And as we’ve grown, you’ve grown too, and it feels like we are both passengers on a similar journey, and it’s been a great honor and pleasure for me to watch you folks do so well.
Jay: Well, thank you, that means a lot. Shopify has been an absolutely amazing partner. I had my first store on Shopify in 2010, so I don’t know where that fits in, in the timeline.
Harley: What store was it? What was it?
Jay: The first one I launched was called Supreme Archery. So I don’t know, like when did you start with Shopify?
Jay: So I launched it in, I want to say, like April, 2010,
Harley: I was at Shopify. I was just starting Shopify at that point.
Jay: So it was probably right around the same time.
Harley: Yes, that’s so cool.
Jay: So, I was a merchant for a couple of years and then obviously started doing the whole app thing and became a partner. But yeah, no, it’s 11 years. I guess now we’ve been either on the merchant side or the partner side with Shopify.
Harley: So cool.
Jay: Awesome. Well, I want to start with a weird question. What did you eat for breakfast today, Harley?
Harley: Nothing, I don’t eat breakfast. I have not had breakfast, I swear, I have not had breakfast in probably, I don’t know, 20 years.
Jay: Are you intermittent faster?
Harley: I guess. By the definition that I probably don’t eat solid foods for 18 hours. I have my dinner, we have small kids, so we dinner fairly early. So, I’m usually done there by about seven or so, and my next meal is usually lunch the next day. So I’m not trying to, like, biohack or anything like that, or sort of have weird tech guy flex, but I’m not hungry in the morning, and for a long time I was always sort of told that, you’ve heard this famous maxim, that the most important meal of the day is breakfast. But when I used to eat breakfast in high school, because my parents were like, you have to eat breakfast, I always felt sluggish, and then when I went to university, I guess 21 years ago at this point, 20 years ago, at this point I just stopped eating breakfast and I felt I had way more energy, and so I eat a pretty healthy lunch. I tend to have larger dinners, but I skip breakfast.
Jay: Yeah, interesting. Okay, then my last weird question is, this weekend are you going to fat bike or ski?
Harley: Oh dude, both, definitely.
Jay: I saw you’re into fat biking recently.
Harley: I am, I am really into fat biking. Fat biking is so much fun in the wintertime, and what’s neat about it is at this little ski resort where my family and I ski at, skiing is great, but it’s not a big resort. It’s nothing like Whistler, or Aspen, or Tramla, it’s a very small sort of country ski resort. It’s a lovely place, but the infrastructure is not really up there, and so by the afternoon, the skiing just, it just gets skied out and they sort of, they call that break a leg weather or break a leg skiing because it just skied out. So in the mornings and on the weekends, I ski with my kids, and actually tomorrow will be the first time ever in my life that I’m going to ski with my wife. My wife was not a skier. She’s never skied, and about a month ago, she just decided now that I’m skiing and our kids are skiing that you want to ski too. So she’s been taking lessons, and tomorrow her and I get to ski together, which I’m really looking forward to, and then in the afternoon I get to go fat biking, which is a fun activity.
Jay: That’s amazing. I have like three different fat bikes in carts on different stores right now and I’m right about to pull the trigger on one, but I think I’m going to go the e-bike, e-fat bike route.
Harley: So that’s what I ride, the e-fat bike. There’s a company called Moose Dash. It’s a French company that I really like. The reason that those are great is because those fat bikes tend to be lighter. So when I really want to get a good workout in, I can just turn sort of the assist to zero, and it’s just a regular fat bike, and I can just, I sweat it out, and then when I’m with a group and we’re really climbing a lot, and we want to be out there for a couple of hours, I can turn the e-bike on, but it is quite amazing. And actually, I know this is not a podcast about e-biking or fat biking, but one thing that is also really great is I got studded tires and I don’t know what it’s like, where you ride, but where I ride, it gets really, really icy. I mean, the ski resort is in Quebec, and Quebec in February, and March, and January gets really cold. So having studded tires has made a huge difference.
Jay: Good tip. Okay. Well, yeah, this is not a podcast about fat biking, but it’s about you. It’s about Shopify. I actually want to break this into, I think, three kind of sections. So actually the first section is about you, the second bit is about Shopify, and then a little bit about ecommerce and your thoughts and predictions and kind of go where it goes. But I think most people know who you are. We don’t have to spend a ton of time on that, but your whole history, if you Google Harley, you’ll find lots of fun facts of how he got to where he is today. I’m curious what a day in your life looks like today at Shopify. What keeps you busy right now?
Harley: One of the best parts of Shopify for me, I sometimes think about Shopify as sort of the greatest place environment for me, and part of that is the Venn diagram of my personal interest, which is entrepreneurship, as a hobby, overlaps with my professional job, my career, which is as president of Shopify, which is all about empowering entrepreneurship and entrepreneurs. So the fact that my hobby and my profession are almost the exact same thing is absolutely amazing, and that means there’s only a couple of companies on the planet that would even be the right venue for me, and Shopify is absolutely that. But what’s neat about Shopify, in the early days, and I think it has continued and certainly is the case today, is there’s always really new, interesting problems. A lot of my job is storytelling, making sure the world knows that what we’re doing and why we’re doing is so important. In some other cases, it’s spending time with stakeholders, whether it’s partners like you, or it’s a new channel integration we may have, or it’s 45,000 agencies that we work with every year, or it may be doing media press and PR and in getting our story out there.
In other cases, it’s working with some of our teams. I’m spending a lot of time right now with our ecosystem team and our shipping, our fulfillment team, the SFN team as well. Previously, I was spending a lot of time with our Shopify Plus team. So the neat part about Shopify is, I’ve said this publicly before, but it’s worthwhile mentioning that at Shopify, you absolutely have to requalify for your job every year, no matter what your job is, whether you’re Toby or anyone else at the company, you have to requalify. It is not a given that just because you’re there, it means you’re going to continue to have that job, and that creates this incredible motivation to keep growing. The personal growth that Shopify creates for the people that work there is unlike anything I’ve ever seen. I’m sure I know that at Bold, you guys think a lot about personal growth and the journeys of the people that work there, but I’ve never seen, because I’m at Shopify my perspective is that of our company, I’ve never seen a place where you really can get 10 years worth of career development every single year, and I feel that and so Shopify, I’m in year 11 now, and so I guess it’s a hundred years of career development in a decade, but no day ever looks the same, and I think that is absolutely amazing.
Now, part of what I think any good leader has to do is to figure out pretty quickly what they’re good at and what they’re not good at, and I think at a lot of companies, what tends to happen, is leaders tend to be, there’s a pull to be this well-rounded object. And Toby refers to this as river stones: you put a stone in a river, a spiky stone, and after a long time that stone is going to be smooth and it’s going to be well-rounded, but it loses that spike. And at Shopify, we really try to make sure that the people that are spiky, that have those incredible spikes, that actually those spikes get better and to really make sure I’m clear on this, if you have a particular skillset and you have a superpower at Shopify, we want you to get better. We want you to sharpen that edge to get better at that particular thing, and the stuff that you’re not good at, it doesn’t mean you shouldn’t mitigate those weaknesses, but there are people out there that are really good, like world-class at the things that you may not be so good at. And so if you sort of think of two different paradigms of growth as a leader, one is to get good at everything and get well-rounded, the other way to do it, and I think Shopify does as well as sort of become more T-shaped where you have a breadth across a lot of different areas of the business, across a lot of different disciplines, but you’re able to go really, really, really deep on one discipline. And for me, that discipline that I’m trying to go really, really deep on is that storytelling aspect. I want Shopify to become synonymous with entrepreneurship, and I’m devoting my life to make that happen. And I feel grateful. So back to that first comment, that Shopify is sort of the perfect company for me to work at because it allows me to do the thing that I would have done anyway, except with incredible leverage and scale.
Jay: Well, it’s working. I think a lot of people would say that Shopify and entrepreneurship are almost a synonymous word. A couple of things you touched on there that I really liked, the spiked pebble, I’ve heard Toby mention that before too. I think he was saying at one time with compromises a stone put in the water rounded to nothing over time.
Harley: Exactly, yes.
Jay: I thought that was really good.
Harley: Yes, and then the same thing as is right about leaders, a lot of leaders go into an organization with some spikiness and they come out of the organization well-rounded, and I’m sure for some companies, that’s great, that’s what they want, that’s what their objective is. That’s not our objective, our objective is to help you hone your superpower, for you to sharpen that edge, for you to double down on what you’re really, really good at so you can become world-class at it, and that means that there are some things I’m just not going to be good at. I’m probably not the best person in a product review meeting. I understand product because I was a merchant. I understand product on a deep level, but there is no better product visionary on the planet, in my opinion, than Toby, and that’s the reason why Toby is running product now. He is the Chief Product Officer as well as the CEO. That is really unique at Shopify, and I don’t know too many companies that operate with that type of philosophy.
Jay: Yeah. So on the entrepreneurship topic, why are you so passionate about entrepreneurship? And I guess what does it mean to you to be an entrepreneur? Why do you care about it so much?
Harley: I think that entrepreneurship is the great equalizer. I think entrepreneurship is the greatest vehicle for equality and independence, and whatever your unique definition of success might be, and that is not a unique or a novel idea. My dad’s an immigrant. My dad immigrated to Canada in 1956 when he was just a little boy, and it was during the Hungarian revolution, came from Hungary, and his parents, they used entrepreneurship when they got to Canada because they had no money, and they didn’t speak English, and they had no education, and entrepreneurship, which they didn’t call it that, but the way that it manifested itself for my family, for my dad and his parents and his siblings, was my grandfather opened a little stall at a farmer’s market selling eggs, and he spent the next 72 years, I believe, selling eggs at a farmer’s market until he passed away. So for him, entrepreneurship was a way to survive, it was a survival technique and it allowed him to put a roof over the head of my dad and his siblings and my grandma and put food on the table.
Fast forward from 1956 to 1996, four decades later, entrepreneurship for me — I started my first company in 1996, so I was about 13 — was I wanted to be a DJ, no one would hire me. I really wanted to be a DJ. I loved the idea of creating this atmosphere of joy and taking a sleepy event, where people are sitting at some hall eating rubber chicken, and five minutes later, getting every single person on the dance floor, with the men taking off their ties and putting their ties around their heads, and everyone’s just dancing and everyone’s having a great time. I love that idea.
Jay: Holding up the chair.
Harley: Exactly yeah, doing the Hora. But no one would hire me because I was 13, I knew nothing. And so entrepreneurship was my way to solve that problem. I can start my own business, whatever that meant. I didn’t have any money, but I can call myself a DJ company, and I can hire myself, and then a couple of years later, I came back to Montreal, back to Canada, from South Florida, where I was living with my parents, to go to McGill. Mom and Dad lose everything, Dad is no longer around, and I’m forced to help support myself, but also help support my mom and two much younger sisters. And once again, I pulled out that tool that is entrepreneurship and started selling t-shirts at universities. So my own personal experience with entrepreneurship, is that it’s the greatest tool to solve problems with. If you think of it that way, I’m not trying to name-drop, but literally right before jumping on with you, Jay, I was on a call with Rebecca Minkoff, the person, Rebecca, not the brand. And so Rebecca and I were talking, same thing. Rebecca had this idea for an “I love New York” t-shirt, and then a purse called the morning after purse, and she wanted to, she had this great idea, and she wanted to, number one, see if that idea was possible. One, If she can manufacture, and create that, and make that, and two, would people want to buy that.
She could have gone to work at some big company, and she could’ve gone to work at some big fashion house — she’s always been very talented — but it just wasn’t working in that way. No one knew who Rebecca Minkoff was, and so she pulled out that tool called entrepreneurship, and she started Rebecca Minkoff, and she created what is now the famous, incredibly famous purse, this bag, which is called the morning after bag, and everything changed for her from that. This idea that you, as a human being, can solve a problem entirely on your own, without any capital, any resources, for the most part, and that can turn out to be the next Bold, or the next Shopify, or the next Rebecca Minkoff, or just putting food on your family’s table. That is what entrepreneurship is and that’s why it’s so important. And I think the problem with it is that it still feels inaccessible to most people. Entrepreneurship, even to those who are around it, take my wife, for example, Lindsay, for a long time, Lindsay would not self identify as an entrepreneur. Even though she lives in a house with me, and she’s married to me, and all I talk about is entrepreneurship and all day long, every day for her, she’s like, well, this doesn’t feel like me. Like I don’t look like what I think an entrepreneur looks like.
So the reason it’s important is, because I think it’s the greatest equalizer, and it’s the greatest way for human beings to self-actualize, and it’s the greatest way to find your own path in the world. But it’s also even with great software, and great applications, and great functionality, and technology like Bold is doing, and Shopify is doing, it still feels out of reach to most people. So if I can connect, and this is frankly, my life’s work, I will spend, I’m 37 years old and I will spend the next hundred years of my life working on this thing. If I can connect people who want to solve a problem with the tools to do so, and convince them that they can use entrepreneurship as a vehicle to find their thing, to solve their problem, to create something that they want to share with the world, that feels like a really good way to spend my life.
Jay: Would you say every entrepreneur is a business owner and every business owner is an entrepreneur, or are they not the same?
Harley: I think they’re the same. I know a lot of people that work at companies, I know people that work at Shopify. I work at Shopify. I mean, I am a business owner. I have sort of side businesses with my wife, we have an ice cream shop together, but no, I think those are very different. I know people that don’t own any businesses at all, in terms of equity, who are entrepreneurs. I think in many ways, entrepreneurship is a mindset and some people manifest that mindset through the creation of product and some people manifest that mindset by solving really tough problems in a very creative way, and I know lots of business owners who are not necessarily entrepreneurs, it is more about the dollars and cents to them. It’s more about, it’s more of a math equation than it is an entrepreneurial venture, and it’s not that one is more important than the other, it’s just, I think when you start using the term business ownership, you’ve already lost so many people, but when you start using the term entrepreneurship, and you make it accessible with technology, and you make it available with great products, and you make it affordable, and you inspire people with other, other entrepreneurs, like to go on a podcast like this, it invites more people into this thing that we call entrepreneurship, but I don’t necessarily think entrepreneurship and business ownership are the same.
Jay: I couldn’t agree more, and I know a number of business owners that are not entrepreneurial at all, and there’s nothing more frustrating than, basically, they’ve created their own job, but that’s what it is. It’s not, yeah.
Harley: You see this often in multi-generational businesses, like family businesses that go back a couple of generations, and if you read about the Bronfman family or you read about some of the, in Canada, at least some of the multi-generational business families, which you realize is the first generation were very entrepreneurial. Old man Bronfman was a bootlegger. He was bootlegging during prohibition. He was hustling hard and he was able to turn that into Seagrams, and he was able to acquire Universal, and he was able to acquire Tropicana, and like to build this thing, and then the second generation comes in and maybe they’re a little bit less entrepreneurial, but that is a good example, by the third generation, not always, but sometimes, you end up having business ownership as opposed to entrepreneurs, and I don’t think those two are the same thing.
Jay: Yeah. Cool. I want to get into Shopify a little bit. I have lots of questions on the Harley side, but well, actually, one last thing I want to ask on the Harley side, is I’ve heard you talk a lot about, and you’ve always been passionate about mentorship and having mentors in your life, I wanted to ask you, do you still have a personal mentor? What would you recommend to most of our listeners who are merchants, partners, what are your thoughts around that?
Harley: Mentorship is really important to me because, but first of all, let me redefine mentor. I don’t think you have, like, one mentor. I have a really great mentor in my life who helps me better understand how to be a great spouse and partner to Lindsey. It’s someone whose relationship with their spouse is just quite incredible, but I’m not sure I would go to that particular person who may be listening to this and ask about business mentorship, and I have business mentors or leadership mentors who are wonderful at that particular aspect of life, and I’m not sure I’d go and ask them how to be a great parent, and when we had Bailey in 2016, our eldest daughter, who’s now almost five years old, I was nervous about being a first time dad, as most first-time parents are, and I looked around and I just sort of noted over the years that there were a couple of people in my life, friends, family members, family friends, just kind of people in my orbit that I was like, they’re doing parenting really well. I don’t know what it is about it, and so I would call up these people and say, “hey, look, I’m about to have my first child, and I’m scared shitless, and I’m sure a lot of people are, but there’s something about the way that you handle parenting that I really admire. I’d love to ask you some questions,” and then I’d prepare because these people don’t, in some cases they don’t even really know me that well, I’d prepare and I’d say, “look, I only want 20 minutes and here are five questions I want to go over with you.”
I’ve been doing that same thing since I was a kid, just trying to acquire a set of personal board members, effectively, in my life, and if you think about it like a board of directors, I know you have a board of the sub-committees on a board, you have audit committee, you have compensation committee, you have governance committees, you have county, whatever, all the different committees you might have. So everything about my board of directors, I have a sub-committee for my relationship with my wife, and I have a sub-committee for parenting, and a sub-committee for my job, and I have a subcommittee for leadership, and I’ve been able to develop these very deep relationships with people over many years, and what’s neat about it is, over time, the relationships in many cases get a lot deeper, and go beyond that. I mean, I used to talk to Seth Goden all the time about business and branding and marketing. I mean, Seth Goden is probably the greatest marketer that existed and is alive today, and now when I talk to him, it’s mostly about parenting, actually. He has two kids, I have two kids. His kids are much older. I’m curious how he’s dealt with that.
So mentorship is really, really important, and I think most people, the mistake they make, is they sort of try this, like, “that is my mentor. I’m going to learn everything about that person. Well, the truth is, if you came to me, there’s a couple of things I think I can probably help guide you on, just based on my own experiences, but there’s a lot of stuff that you can teach me about, and that I’ve no idea what I’m doing, and, I have a mentor now, his name is Pierre, who’s just sort of my mindfulness mentor. I have high anxiety, mindfulness and meditation has been very valuable to me. I think Pierre is amazing at this mindfulness thing, and at being in the moment, being present, being thoughtful about that, I’m not sure I would ask them about running a hundred billion dollar plus public company.
Jay: And I think that board of directors analogy is a great example, and I think everyone has it, whether you pick it or not, it’s your closest five friends, it’s someone you spend time with. It might be a toxic board, but everyone has it, and so you’ve been very deliberate about who gets to sit in those seats, which I think that’s the big takeaway.
Harley: There could be a point where you have to swap one of them out. There is a shelf life to some of these mentors, and some of these mentors, because their own experiences, may actually stop being as valuable. There could be diminishing marginal returns. I had a mentor years ago who was a great mentor in a couple of aspects of my life, particularly as I was navigating law school, and realized that he was going through his own stuff in his life, and at some point, the advice that I was getting was so subjective and so biased towards his own experiences that it stopped being valuable to me, and I very politely said, “this is great, but I think I’m good for now.” And that’s a tough conversation to have, but that idea of having a dynamic set of mentors that come in and out of your life, based on what you require at this particular moment, is really, really important, and the cool part about it is, like, I think the idea of sending out a thousand emails saying, “can I buy you coffee?” It’s probably not the way to do it, but finding out what those people are doing, what they’re up to, that’s something that I’ve always used as if there is a mentor, or someone that I want to get in touch with, someone that I want to build a mentorship relationship with, who has a book coming out, figure out a way you can make their book launch more successful.
If nothing else, they’re going to feel an appetite, or an interest in you, help them, maybe they’ll help you, and if they say, “hey, well, you’ve been really kind to me and very generous with me, what can I do for you?” Like, I don’t need anything other than, would you mind if I asked you these five questions.
Jay: And someone can be a mentor that you don’t even ever speak to, you just absorb their content and their material, and they’re still a mentor.
Harley: Totally, exactly right.
Jay: So speaking of books, I think it was you one time who referred to Shopify as a book with many chapters. I wanted to say, or ask was that you, did you recall?
Harley: I think so.
Jay: It might be something that, like, everyone says about their business.
Harley: I’ve talked about Shopify in the context of chapters in a book, I suppose.
Jay: It’d be important to know, like, what chapter you’re in. So I guess my question is, what is the title of that book? What chapters have been written? What chapters are you writing now? And when is the book complete, or is it never complete?
Harley: Alright, so I’m going to unpack in a couple different levels. I don’t know, maybe the name of the book is “Arm the Rebels” or “Arming the Rebels,” I think that’d be a really cool thing. And it’s interesting because, well, first of all, I would say that we are maybe just starting chapter two right now. That’s kind of what it feels like. It feels like chapter one, and I just finished it. How many chapters, I hope there’s going to be an unlimited amount of chapters, probably chapter one was really ecommerce, and helping people sell stuff through their online store, and the reason I think we’re probably on the next chapter now, early chapter two, or maybe late chapter one, is because if you think now about what people, the relationship Shopify has in the lives of the 1.7 million merchants that use Shopify, many of them, most of them use us as an ecommerce, but we’re also in some cases, their capital provider or their payment provider or their fulfillment provider or their shipping provider. In other cases where the retail operating system.
For a lot of our merchants, they would say that Shopify is their business’s central nervous system. It’s what they refer to as work in the morning when they open, when they go to work, they open up their laptop or their desktop, and they log in to Shopify as admin, and that’s where they spend their day. So I think chapter one was us sort of getting set up, making sure we have a great product, making sure we add a lot of value, and now, I think now we’re sort of getting into this next chapter. Shopify right now, if you think of us as a retailer, pretend we are a retailer for a second, we’d be the second-largest online retailer in America after Amazon, but 9% of total ecommerce in the United States is not on Shopify, and that’s cool, and it’s a really neat little factoid, but why is that important? Because Shopify, and you know this more than almost anyone, Jay, like, Shopify is very much a proxy for independent retail, for small business retail. The majority of merchants on Shopify are independent brands and small brands. Some of them will become bigger brands, but they’re all sort of owner-operated entrepreneurs, and the fact that we are growing at the pace that we are means that independent retail is also growing at the pace that we are.
So, I think this next chapter is really about how do we add more value? How do we continue to break down some of those barriers to success, level the playing field? And I think the cool part is that we’ve been working on the supply side, the tools, the education, the resources, so that you can start great businesses on Shopify; but the demand side, which is the consumer side, that’s now catching up, and now as we sit here in 2021, we are seeing consumer preferences shift towards buying and supporting and voting with their wallets for these independent brands in a way that we’ve never seen before, and it almost feels like the olden days where if you wanted bread, you bought from the Baker, and if you wanted shoes, you bought it from the Cobbler, and you bought it in the town square direct from the people that made those products, and that is what I think is so interesting about right now, what’s happening in retail and commerce, and what’s going to happen in the next decade or so, but in terms of how many chapters, we use a hundred-year perspective on Shopify. We’re 15 years in, we get 85 years left to go. We got lots of chapters left to go, and I like the fact that our relationship with the people that use our product is so different than most software providers.
If you’re a CMS or you’re a blog provider, something like that, or you are, I don’t know, check any of the apps on your phone, if it goes down for a day or two, it’s going to be annoying. But if Shopify goes down for a day or two, you lose your livelihood. Now, that is incredible, incredible responsibility, and we take that very seriously.
Jay: Yeah. I think from the outside, it looks, I would say chapter one seems to be removing all the friction. I remember one Shopify Unite, Toby talking about the, I can’t remember the terminology, it was like the barriers to, it used to be to get a merchant account, it took 45 days to be able to process a credit card, and what do you call those?
Harley: You have to fax your passport or you have to ship a copy of your passport to Utah.
Jay: I had to sign my house as collateral to be able to use Moneris.
Harley: You’re right, I was there, I’ve been there too.
Jay: So it’s leveling, that seems like that was chapter one. What was the terminology used at Unite when he was talking about that? I can’t remember, but you remember the talk, removing all those down levels. Chapter two from the outside really seems to be now, how do we help those brands really succeed? I feel like the challenge of making it easy to start an online store, like you’ve kind of solved that, now it’s with Shopify fulfillment, it’s with Shop App and different tools that make it easier now for these brands to grow. I don’t know if that’s an observation from the outside.
Harley: I mentioned that 9% of US ecommerce is on Shopify, and that’s great. But the other side of that is every 28 seconds a new entrepreneur, a new store, gets their first sale on Shopify, and the reason that those two data points are important together is because not only are the stores that are starting on Shopify growing really fast and succeeding in a way that, frankly, we’ve never seen independent brands succeed before and grow. I mean, who would have thought a shoe company starting in 2015 would grow to be Allbirds and be more valuable than Reebok, or that an athletic apparel company out of the UK started in a dorm room by a pizza delivery boy, and Ben Francis would become Gymshark. I mean this pace of growth, it’s unbelievable. So at the same time that the successful stores are getting bigger, and they’re taking more market share, and they’re becoming the leaders in their verticals, there’s also more people trying their hand at entrepreneurship, and that I think is really the key to the entire Shopify. I hope the Shopify story, the Shopify book, is that we not only grew our piece of the pie and made it easier for existing brands to become successful, but at the same time we created brand new businesses and we help facilitate the creation of more entrepreneurial activity, and that together, I think, is sort of what makes the story in the book so compelling.
Jay: Well, today we’re recording this, it’s March 12th. I’m not sure exactly when this episode will air, but today’s an interesting day. I don’t know when did you, at Bold, I think March 12th was our last day in the office. With Shopify, do you remember yours?
Harley: I think it’s almost 12 months ago to the day.
Jay: To the day, yeah, because I remember you guys announced you were going all from home, and I think we were a day or two, anyways give or take. So happy pandemi-versary, I guess.
Harley: I guess, geez, what a time it’s been.
Jay: What has the pandemic done to Shopify to you guys? I guess, like, from product and company?
Harley: When the pandemic hit, we told the whole company to throw out their plans for 2020 and to focus on what we can do to help businesses and small businesses, in particular, survive. And so you saw us do things like a 14-day trial became a 90-day trial. Our point of sale product for physical stores now has pickup options or local delivery options, curbside pickup options. We created a gift card product so that service-based businesses like restaurants can also get some money in, get some cashflow happening, and so those are sort of the things that we did immediately just to kind of help small businesses. But actually, I think Shopify, in many ways, I’m really proud of how Shopify showed up. I’m really proud of how we came to the table when things were at their worst. I think Shopify was at its best, the people at Shopify were at their best, and part of it is that the deep empathy and care we have for small businesses, we watched our local small businesses in our communities and our towns and our cities really, really struggle, and so we mourned what we lost with COVID. We mourned the loss of going to the office every day in a physical environment with our colleagues, and we immediately focused on how we can be valuable. And I hope Shopify is looked upon through the pandemic as a company that really, that stepped up, that helped small businesses survive. We were really lucky, a couple of days ago, we were awarded the third most innovative company by Fast Company.
Jay: And the two ahead of you were the makers of the vaccine.
Harley: Yeah. I mean, number one was tied to Moderna and Pfizer, and then Shopify. And if you read, do you have it up there? Do you see what it says in terms of why we received it?
Jay: Actually here it, it comes on. I liked how they had the quotes. It was a Shopify for giving small shops a lifeline.
Harley: For giving small shops a lifeline. That to me is one of the most amazing, I’m so proud of that. It truly is, this isn’t a hyperbole, it’s one of my most proud moments is seeing that, that, I mean, Pfizer and Moderna, what they did was unbelievable. I mean, they created a vaccine inside of six months.
Jay: You beat Space X, Netflix.
Harley: It’s unbelievable, and it’s because rather than focusing on Shopify, we focused on how — if you want to be the entrepreneurship company, you don’t just say it. You don’t just go on TV. You don’t just write blog posts about it. You actually need to do it and I’m proud of how we did that, and I think that there’s more to do. I think we’ve done some really good things in certain geographies. I think in other geographies, there’s a lot more work to do. I think there are certain types of businesses that we can do a much better job with. We’re spending a lot more time now on physical retail with our point of sale product. We think there’s a real opportunity on the other side of the pandemic where physical retail will not only make a comeback, but will be a part of the larger retail strategy for brands. And so, yeah, so I’m proud of us. I don’t say that patting ourselves on the back or anything, but it was a year, it was really trying on a personal level. You know me, Jay, like I’m a power extrovert. I’ve been sitting in my home office here for 12 months by myself, and it’s been really trying, and I think that rather than focusing internally, we focus externally on how we can help. And I know Bold did the same thing. I think that’s one of the reasons that this ecosystem of ours, this incredible community that the Shopify partner program has and has created, the reason it is so deep and so rich and so authentic, is because in many ways, our objectives are very much aligned. We care about businesses. We care about entrepreneurship.
Jay: What would you say is the most valuable part of Shopify, like either feature, or most valuable part of it that people don’t know about or don’t really understand?
Harley: I think it’s the ease of use. I know that sounds obvious, but it’s not obvious. You and I are both tech entrepreneurs. We live in this sort of tech world. Our days are spent on our laptops and playing with software and technology. Most people are not like that, and so the fact that Shopify — it’s not easy to be an entrepreneur. Entrepreneurship is tough. I don’t want to glamorize it and it should not be glamorous. It is very, very difficult, but the fact that it’s a little bit less difficult because we were able to develop software and you’re able to have software as well. That makes it a little bit easier so that you don’t necessarily need to hire someone. You don’t necessarily need to be an engineer. You don’t necessarily have to have a deep technical background to build a business, that, I think, is probably one of the most important parts of Shopify.
So I guess on the front side, it’s the approachability, the ease of use, and then I think on the other side of it, there is very few pieces of software that exist in the world where it’s easy to start and then when you scale, when you get really big, to get a hundred million dollars or a billion dollars a year, you never have to leave the platform. That idea of being able to go from cradle to scale, that idea of going from your dorm room to the biggest brand, in your category, and doing it all on the same software stack, that is really, really challenging. It’s not an easy thing to do, and the cool part about Shopify is that in many ways, Shopify under the hood is so rich and so deep, has so much functionality, and it’s made only better by having great partners like Bold, who build on top of the platform, build extra functionality and new features and make sure that everyone finds product-market fit, but the complexity and the depth of Shopify only reveals itself when you need it. Which means that while it’s very technical, if you want it to be, it’s also very approachable when you need it to be.
Jay: Yeah, there’s so many. I remember when I thought about this question, I was curious where you would go, because I think there’s like Shopify capital, and Shopify balance that people probably hardly know about, I think one of the biggest values is, and I might be biased, but I think it’s the ecosystem as well, too. Like of all the partners, like that’s hard, you can’t replicate that.
Harley: Well let’s shift gears, right? I mean, I was really like, on the merchant side, as you and I sit here right now, there are thousands, tens of thousands of people right now thinking about how to make the lives of merchants better using the Shopify platform. There are some of the smartest people in the world right now sitting there thinking about how do we help this cause of making entrepreneurship more accessible, and that partner ecosystem that we have is, I think the reason we have it is because of, it’s not even like we’re colleagues or anything like that, it’s actually we’re on this mission together, and we all participate in advancing the mission in different ways, whether it’s building apps or building themes or referring merchants, or it’s building new software, or it’s creating some sort of new partnership, or whatever it may be, this idea that we all have alignment on what is important, and how do we help each other advance that, that mission, that creates a community.
I mean, you see it on social media, you see it on Twitter. I mean, you and I have been on text messages for a decade together talking about everything under the sun around how do we help entrepreneurs? How do we help brands be more successful? And that collective passion, that collective journey that we’re on together with people that we actually really like because we really like each other. I mean, yes, we have a professional relationship. Yes, we have a financial, economic relationship and partnership, beyond that, the people that we work with, we really quite like, and that makes all of it so much better.
Jay: There are lifelong friends that have been made along the journey as well, too.
Harley: I mean, look what happens pre-pandemic every time since we started Unite, you and I see each other, we see each other, we hug, we’re not hugging because we want the photo op, like, we genuinely want to give each other a hug because we know when we see each other at Shopify Unite, our partner conference every year, we both look at each other and we’re like, remember last year we made a lot of progress? Let’s keep going. Let’s keep going. Let’s keep going together, and let’s bring each other along for the journey together, and that I think is so cool.
Jay: I want to be respectful of time here. I had a couple last quick questions because I want to make sure I get to a couple of really good ones here, but what does the future look like for Shopify? I know there’s no such thing as winning. I don’t believe you guys are playing a finite game. I think you’re always asking questions and you’re curious and exploring paths. Where do you think Shopify is exploring in five years?
Harley: There’s still a lot of areas of starting a business, and running a business and scaling a business that remains very difficult. I mentioned earlier, I was on a call with one of our merchants, with Rebecca Minkoff earlier today, and Rebecca’s got one of the greatest fashion houses in modern history. I mean, she is the American example of what a fashion brand, a designer, can do, and it’s incredible the scale she has. But you sort of say, so where are your struggles now? And how are you thinking about these sort of things, and entrepreneurship to start is difficult, and as you scale, it’s also really, really difficult. So there’s so much we can be doing, but there are some things that just should not be the way they are. A great example is Shopify Balance. Shopify Balance, which we announced last year in Unite, which is in early beta in the US now, it’s our way of, we took a look at how business banking is done for small businesses and so many small businesses still use their personal bank account. Why is that the case?
As we began, sort of, to explore this idea of cash flow management, and money transfer, and banking in general, you realize that the traditional banking institutions were just not, have no empathy, and have no understanding of what small businesses need. And so can we take a crack at that and make that easier? And so five years ago, we never would have thought that we’d be creating a cash flow management account sort of thing. But we realized, actually, that is an impediment to success, and so I think what you’ll see over the next five years is you’ll see us go into areas where you may not necessarily think we were going into, but the larger theme across all these areas is that they are impediments to merchant success. They’re impediments to scale, they’re impediments to people getting started, and we started the conversation with talking about payment gateways. You no longer have to think about a payment gateway anymore on Shopify, you start with Shopify, and by default, we provision a merchant account on your behalf and you can start accepting payments right away. That means that that whole issue that you and I faced when I was starting my Shopify store in 2006…
Jay: People will never know the pain.
Harley: Exactly, you were saying in 2010, no one will ever know the pain of that. There are so many other areas where we can help and we continue to do so. Now remember also, if you agree with me that the future of retail is retail everywhere, and I think you do agree with me in that there’s a consumer choice where they want to buy, and that brands need to sell where their consumers want them to sell, full-stop, then where you go with that, is we also have to make sure that every surface, digital or physical, and anywhere in between, where consumers are spending their time, the digital main streets, or the actual main streets in the world, we need to make it really easy so that merchants can easily sell on those digital or physical main streets, and that’s the reason why you see us announce things in the last year with Walmart, because a lot of consumers are going to walmart.com, and so now, from Shopify, you can push your products to walmart.com, or Tik Tok, or deeper relationship with things like Instagram, where now, not only can you sell something on Instagram, but you can use Shop Pay to do so, which is much faster to use, four times the speed on checkout, and almost two times the conversion rate. I mean, these sort of things on their own are really important, but when you aggregate them, what you do is, you see this incredible tidal wave of making commerce better for everybody.
Jay: And the pandemic is only going to speed that up. The concept of having to buy something in a store is not gone forever.
Harley: It’s not gone forever, but I do think there’s a role for physical stores. I think that some people, my favorite grocery store in Ottawa is a local Italian grocery store called La Bottega, I think, the greatest sort of Italian product source from Italy, and just delicious stuff. I look forward to going in there because that experience of being in that store and asking questions to the owner is wonderful. I want that back, but if I know what I want to buy, I know exactly what the product is. I want to go to LaBottega.com and just buy it.
Jay: Yeah, yeah. I hear ya. Well, we’re almost out of time. I just want to ask you one last question for everyone listening, they’re entrepreneurs, you’re an entrepreneur. Do you have any favorite quotes or piece of advice or something that has really meant a lot to you, whether it’s a saying or something over the years that you would like to leave our listeners with?
Harley: I’m not sure if it’s a quote or saying or inspirational. I’m not sure it’s something you can put on a poster, but I want to remind everyone that the cost of failure right now in entrepreneurship is about as low as it’s ever been, ever. The accessibility, put another way, entrepreneurship has been more democratized in the last five years than the last 500 years, and if you’re not sure if you’re an entrepreneur or not, and you don’t know what to sell, maybe you make, I’m really into tea these days, I’m sort of moving away from coffee into really great green tea. One of my best friends is David Siegel, who was the founder of David’s Tea, and so he’s really got me into, and it’s delicious, and a neighbor of mine actually likes doing pottery, sort of a la Seth Rogan, and I knew that I was like, “hey, can you make me a bunch of really cool tea cups,” and that neighbor did that. And the next week I spoke to him, and I was like, “are you going to sell that stuff?” And he’s like, “what do you mean?” I was like, you set up a Shopify store, your stuff is amazing, you should share that with the world and now we’re setting up his little teacup store cause he’s into pottery.
My grandmother, she makes beautiful blankets for her great-grandchildren, my daughters. I want my grandmother to share that gift with the world if she wants. This idea of commercializing your hobby, this idea of taking something you already love and sharing it with the world. I think that is such a wonderful way to spend time, to find your life’s work, to find something you’re really passionate about, and entrepreneurship can be this great vehicle to do that. So I don’t know if that’s a short quote, but there’s never, ever been a better time to be an entrepreneur, and if you start something and it fails, that’s okay, try it again, or try something different. And if it works, scale it and share that thing that you love with the whole world, because frankly, our parents and our grandparents, and our great grandparents, they never had that opportunity that we have right now, and in many ways it is the greatest time ever for entrepreneurship. It’s still not accessible enough. It’s still not available to most people. It still feels out of reach to so many, but it’s better than it’s ever been in that respect. I’m incredibly optimistic
Jay: For the cost, it’s almost equal to getting a job somewhere and going out and buying a new suit for your first day at the job. You could start a store and take a swing at that ball. Well, Harley, that was great. Thank you so much. Obviously everyone knows where to find you guys, shopify.com. We’ll leave everything in the show notes that we talked about. Really appreciate your time and keep on with your life’s work. You’re doing a great job. There are millions of entrepreneurs on the merchant and on the partner side that have built businesses on top of Shopify, and keep doing what you’re doing, man.
Harley: Well, look to get together with you Jay and everyone at Bold and all of our partners, we are the guardian of the world’s entrepreneurs. We have been tasked whether we want it to or not. I think we didn’t want to, but we’ve been tasked with not only protecting the world’s entrepreneurs, but helping create new ones. We want more entrepreneurs to exist, we want more voices in retail, and together with great people like you and everyone at Bold, we’re doing that. So thank you so much.
Harley: Thank you.