Shopify President on How E-Commerce Is Changing in 2026 | Harley Finkelstein

Every 26 seconds, a brand new entrepreneur gets their first sale on Shopify. It is only in this particular era that you can go from mom's kitchen table to doing $3 billion of topline revenue inside of 3 years.

I remember standing at the New York Stock Exchange ringing the bell was truly one of those incredible moments. I don't think you can inherit that give a factor unless you are kind of a founder.

Thank you for having me. It's an honor to be here.

It's interesting. I think actually for a long time it was sort of that romantic version. I think ultimately if you go back 300 years, the baker really loved baking bread and the cobbler really loved making shoes. They were attracted to something that was like their craft and then they were able to kind of commercialize that craft. Pretty much for the industrial revolution, we kind of went away from that and it was like, okay, forget about what you love doing. Do the thing that's going to provide shelter and provide food for your family. And then people started to get a lot more kind of focused on like jobs and career and employment. And actually now for the first time I think like maybe since the days of the baker and the town square we're back to the point where we actually can do things that give us real purpose and real meaning. But I think there is this certainly for in my upbringing and for my family, entrepreneurship, which they never called it entrepreneurship. It was called small business, but that was a means of survival. It was my grandparents, immigrants come to Canada in '56 from Hungary. Holocaust survivors. They escaped the Hungarian revolution, immigrate as refugees to Canada. No one's going to hire my grandfather or my grandmother. No one's going to give them a chance. They don't speak the language. They have no money. So entrepreneurship was like the only thing they could do. And in the case of my grandfather, he found out that there was an opportunity to sell eggs at a local farmers market. And he spent literally 75 of the next 75 years selling eggs at this little farmers market in Montreal. Was he an entrepreneur? Unequivocally. Did he call himself that? Certainly not. But he was doing it because he had no other choice. And I think there's an entire generation, certainly for, you know, I'm in my early 40s and I think for those of us that are in our kind of 30s, 40s, a lot of our parents and grandparents that were entrepreneurs or small business owners, it wasn't out of passion. It was because they had no choice. And many of them got really good at it. They actually became truly exceptional at a world-class level at their craft. But it wasn't sparked by passion. It was sparked by I have no choice. I've actually had both those experiences in my life. One is when I was 13, I wanted to be a DJ because I just thought DJing was cool. Nobody would hire me. So, I started my own DJ company. So, that was very much passion based. And then as a freshman in college at McGill, my dad was no longer around. Had to support myself. I started selling t-shirts because I was a forced entrepreneur. And I actually think whether you come to entrepreneurship because you are passionate about something or because you have no choice, I think the lesson there is that entrepreneurship remains one of the greatest tools for humans to self-actualize, to find their thing, to solve problems. And I wish more people knew that. Not every problem of course, but for a lot of the problems that anyone who's listening have, starting a business, getting deeper into entrepreneurship may be the exact ticket to solve that issue.

Exactly. That's what I mean. Ultimately the best entrepreneurs I know, they are going on their own personal growth journey and the vehicle they're using for that journey just happens to be business creation, scaling a business, running a business. But it's very personal and I think that's the cool part of entrepreneurship is that it looks different for everybody. And for some people the goal of their entrepreneurial venture is they want to become a billionaire, that's it, they want to make a billion dollars and they want to like buy a private jet or buy some sort of big house or mansion. But for others, the goal is literally just to put food on their table or they want to be able to afford, you know, ballet lessons for their daughters and they can't. And I think that is the universality of it is that whatever your version of success is, you can find it through this thing called entrepreneurship. The thing that I think people miss right now sitting here in, you know, 2026 is that it is probably the greatest time in the history of the world to be an entrepreneur literally right now.

I think most people what they want for their children, my wife and I, Lindsay and I, have two daughters, Bailey and Zoe, and I can see this a little bit. I can see where my parents were coming from and where their parents are coming from, that the idea of having some stability, professional stability is quite appealing. Knowing you're going to get a paycheck, knowing that you're going to have this thing that can last as long as you want it to last from a career perspective. I can see the appeal of that. But I was never searching for that. The idea of having a safe job or a steady career was never in my DNA. As you mentioned, I'd been starting these little companies since I was a kid. I loved entrepreneurship. And actually, the reason I went to law school, believe it or not, was not to appease my Jewish mother or my Jewish grandmother, although they were very proud of the fact that their grandson, their son was becoming a lawyer. I did it because a mentor of mine had convinced me that I should look at education as the acquisition of skills rather than the acquisition of a diploma. And that is a very different tactic to take when you're going through school. Most people start school whether it's undergrad or college or graduate school or professional schools like medicine or law or accounting, whatever, engineering, they do it because at the end of it they get this piece of paper called the diploma and there is some intrinsic value to that diploma. That was not what I was doing. This mentor of mine said, at the time I was finishing college, I was 21, I had a t-shirt business that was going okay, he said, look, you do not have the sophistication yet to fully understand entrepreneurship at the scale that equates to your level of ambition. Meaning my ambition was so high but my skill set was so low there was this massive gap in that. And he said that, you know, I teach law at the University of Ottawa. He's a lawyer but he was a law professor that year, took a year off to teach law. He said law school could be an exceptional proxy or a finishing school for entrepreneurship. You will learn how to write, how to think, how to negotiate, how to be more articulate. You will learn how to read 4,000 pages and pick up the one single line that matters in those 4,000 pages. Because I was young and impressionable and this mentor of mine was someone I trusted, I said, you know what? That sounds great. I'm going to go and apply to this law school. And I ended up getting in. And so I moved to Ottawa in 2005, which is the capital of Canada. I'd never been there before. I only moved there because I wanted to go to law school to get a law degree to become a better entrepreneur. I always knew that my tribe was entrepreneurs. So I asked where were the entrepreneurs hanging out in Ottawa and I was directed to a coffee shop and I met a group of entrepreneurs that we ended up hanging out every Friday night. We called ourselves the Young Entrepreneurs Club. Stupid name. We would hang out every Friday night and we would share advice and insights and tactics and commiserate and talk just about business and entrepreneurship ad nauseam. And one of the entrepreneurs that I met there was Toby who had just moved to Canada about a year earlier. He met a girl who's living in Canada, Fiona, became his wife and he moved there and he was selling snowboards on the internet and this is now a pretty well-known story but he wrote this piece of software to sell those snowboards and realized very quickly that the snowboard business was a good idea. But the software that he'd wrote to sell those snowboards was a great idea. I ended up becoming one of the first people to use what would become Shopify selling these t-shirts, selling my own t-shirts. The experience that I had with Shopify, this is like 2006, so like 20 years ago, it was a superpower for somebody who has ambition because ultimately if you think about the history of business, generally you were always limited by your TAM, your total addressable market. So, for example, here in New York City, if you set up a coffee shop in Chelsea, your customer base, your potential customer base is anyone that walks by that coffee shop. Maybe you do some good marketing and someone comes from Soho to Chelsea because they love your coffee, but generally you are rate limited by the surrounding geography of the coffee shop. But that was not the case with modern online commerce. The internet changed that. It made distribution everywhere. And what I loved about moving my t-shirt business from a wholesale t-shirt business to this online store was when I hit the launch button in 2006, my business had a global TAM that anyone from any country in the world was a potential customer for my business. And I didn't have experience. I didn't have a lot of money. I hate this term, but I'm going to use it anyway because it's the perfect term here. It felt so democratizing that it didn't matter that I wasn't experienced. It didn't matter that I didn't have a last name that people knew. What mattered was my product of value to the people I was selling it to. I fell in love with that idea of my t-shirt business being global. But even more so in that moment, I fell in love with this tool called Shopify that I felt like this was kind of what I was always searching for: a mission, a product, a journey that would allow me to find my life's work. And 20 years later, I think what I found through that journey was my life's work is actually all about entrepreneurship. And specifically, how do I encourage more people who may not otherwise think about entrepreneurship to do so? How do I reduce the risk for them? How do I make it so that the cost of failure is as close to zero as possible? How do I make it so that people that have an idea in the shower in the morning, instead of forgetting about that idea and going to their job they hate, they actually go to their mom's kitchen table and they get started? I ended up finishing law school and my online t-shirt store continued to grow. And then in 2009, I called Toby and said, I do not think there's any better place for me to spend my time, to build a career, to do my life's work than helping you build this company called Shopify. At the time, I think we probably had, I don't know, a couple hundred merchants on the platform. Today, we have many millions. It was a very simple product, e-commerce for small businesses. Now, I think we're about 14% of all US e-commerce. And pretty much anyone who's watching, if you go to an online store that has a great experience, that looks good, is fast, is well-designed, it is most likely a Shopify store. And the partnership that I've had with Toby over the last, you know, two decades has been incredible.

Well, maybe I'll start with a personal one and then I'll start with more of a Shopify one. One of the greatest moments I think for any entrepreneur, and I hope this isn't for everyone, but for some of us, standing at the New York Stock Exchange ringing the bell to take Shopify public was truly one of those incredible moments. I mean that is where Henry Ford stood when he took Ford public. It is just, you know, the New York Stock Exchange or NASDAQ, like this is the capital of capital and to stand there and ring the bell. I think at the time Shopify had about a billion dollar market cap. So I mean we're talking about a long time ago but it wasn't even about the market cap. It wasn't about market itself or the liquidity. It was just it felt like a moment where Shopify really arrived and it really felt to me like okay we were going to build a generational company here. On a personal level that was a very special moment for me personally but I think in terms of like there were a couple periods or a couple things that happened in Shopify's journey that I think have shaped the company. The first one was that I mentioned a little earlier that the initial product was built to help small businesses build beautiful scalable online stores. What happened around the time of the IPO was fascinating. We started seeing that some of these very small stores that started again at their mom's kitchen table started to get really really big. Gymshark for example, Ben Francis starts this in his dorm room in 2012. And by the time of the IPO, these guys were cranking. And so we were watching these seemingly small businesses just grow huge on Shopify and never leave the platform, which is unique in software. Usually for most software customers, as you grow, you tend to hit the ceiling of the product you're using and you have to sort of migrate to the next larger one. You know, eventually you go like from small business to medium business to large business, then eventually you go to like some enterprise platform. But that wasn't happening at Shopify. We were watching these people get started and then grow without any type of ceiling whatsoever. And so that gave us the insight that maybe we can also help much larger companies, established companies also use Shopify. And so in the last decade or so we've seen like Mattel or Hunter Douglas or On Running or, you know, these brands, staples, Estee Lauder, these iconic brands in some cases that have been around for hundreds of years are now coming to Shopify as well. So that was sort of one inflection point. Maybe the second one was around point of sale. I mean like the point of sale terminal you have in like your brick-and-mortar store. It doesn't seem like, you know, such a mind-blowing thing, but the reason that's important is because I think when we began to introduce Point of Sale to the market, Shopify transitioned from being an e-commerce company to being a commerce company. And that subtlety is really important because what that means is that we were no longer just helping merchants and brands and retailers sell on one particular channel, online store. At that point, we didn't know it then because this is like 2016, but at that point, we put ourselves on a journey and a trajectory whereby no matter where consumers are spending their time, online, offline, on social media, on agentic applications, on marketplaces, third party marketplaces, that our job is to make it really easy for merchants on Shopify to sell on every surface area that exists now and some don't even exist now, but will exist in the future. And in many ways that is the moment where we became agnostic to the channel and we began to think more about Shopify like a retail operating system whereby you basically have this beautiful hub in the middle that has all your information, your inventory, your products, your marketing, your analytics, that's where you go to have all your customer data and that hub is like it's the back office, it's the system of record, retail operating system, and then one spoke is the online store, one spoke is your offline store if you have one, spoke may be social media, another spoke may be agentic, another spoke maybe augmented reality, but the idea is that no matter where your consumers are spending their time, you now can sell directly to them. And I think both the first example of growing really large and then also the point of sale example that has sort of made Shopify where we are today, which is that it is the very best place to go and start a business. In fact, best stat in the world to me. Every 26 seconds, a brand new entrepreneur gets their first sale on Shopify.

So the best place to start, but as they grow and they become Alo Yoga or Vuori or On Running or they become Figs or they become all these incredible brands, Supreme or Elevant or the brands, James Purse, my favorite brand on Shopify, that means that they never have to worry about do they have the right partner, that wherever commerce goes in the future, they are future-proofed. They are set up for the highest likelihood of success. And I think those moments, you know, when you're in them, it doesn't always seem that profound. It's like, well, just add a new, now we're doing point of sale or now we're helping big. It doesn't seem so profound, but as you kind of zoom out and you have the perspective of a decade or more, you begin to kind of, you know, draw these little lines, you're like, oh, that led to this, that led to this thing as well. And it's an amazing thing building a company like that.

There are some where it is so obvious. Sarah and Aaron Foster. Yes. Okay. So, I think they're incredible entrepreneurs. Sarah's become a friend. I think Sarah and Aaron are incredible entrepreneurs. I can't figure out where their brand, which is Favorite Daughter, ends and where their TV show starts and where their podcast, like it's kind of like it's all one. Right. Like if you watch Nobody Wants This, which is their hit Netflix show, they're wearing Favorite Daughter clothing. And if you listen to the podcast, we're talking about building Favorite Daughter. And if you walk into their store, you know, you're like it just it all kind of fits together. So there are some who have done it so organically that you almost don't know where it all fits and it doesn't matter. It's not supposed to, like it's not made so that you can understand the segments of their business. It's all one and the same. More people watch the show, therefore more people buy their clothing, therefore more people listen to podcasts. And it's this like wonderful flywheel of growth and entrepreneurship. And it's beautiful to watch because it's just like it's so interesting. In other cases, you have these brands that are not native media companies that have had to figure out their own voice. And some of them do it really well and some miss the mark in truth. You know, there was a period of time in the late '90s, so like '96 to '99 or so, I was in high school in South Florida, and I remember there's this incredible shopping center in South Florida near my house called the Boca Raton Town Center. And it's a really beautiful mall. And I remember walking through the mall with some friends when I was in high school, maybe 10th grade. And we walked into a couple stores. It was like Lucky Brand store next to a J. Crew and next to an Abercrombie & Fitch. And all of them kind of like they all had a DJ for some reason that morning. They all were serving coffee. All of them had kind of the same aesthetic. They were all, I don't know if they were copying Abercrombie or they were like it was all kind of mixed up and everyone was trying to effectively emulate everybody else but it wasn't authentically their own. It was well everyone now needs a DJ so let's put a DJ there. I think about that analogy and that metaphor for like modern-day brands that no one else can do what Aaron and Sarah did. It is so uniquely theirs. So don't try to create a show like theirs or a podcast like theirs. It's just like the way that Kibbitz on the podcast, it's just it's uniquely their own authentic selves. But if you look at a company, for example, like Figs, for example, do you know Figs? They make these amazing scrubs for doctors and healthcare workers. I remember during Black Friday, Cyber Monday 2025, they set up these pop-up stores near hospitals. Why? Because they know their demographics are near work in hospitals and those facilities and so they want to make it convenient to drop in. So they have deep empathy for the people they're serving and so they're building products, experience, content, media for that particular customer. And I think the companies that do it well win. I think the companies that don't do it well that effectively see someone else doing something and say, I'm going to do it the same way, it comes off inauthentic and people know that. Like I can walk in blindfolded to a James Purse store and know it's a James Purse store. Why? Because there's a smell. And I've asked James 100 times about that smell. He's like, there's no smell. I was like, there's a smell. He's, I was like, it's the wood or it's something. Are you lighting a candle? No, no, it's just, he's like, we're not doing any scents. Somehow there is something to that. Same thing when you walk into a Glossier store or you walk into an On Running store. Like you can almost sense it even blindfolded. So, do I think that every brand has to become a media company? Not necessarily. But I do think though that media and your ability as a brand and brand owner to connect directly with your consumer is so much easier now than it's ever been. You don't need intermediaries. So, if you want to tell a story to your audience, you can do through a podcast, through social media, through an ad campaign. You can do it in person. There's a store in Soho that I love called Tecovas. Do you know Tecovas? Yeah. The Cowboys. Company. They're out of Austin, Texas, but you walk into their store in Soho that they opened I think a year ago. It feels like you're in Austin. Not like some copy of Austin, but like a version of like Tecovas in Soho with an Austin vibe. Like they have a bar set up there. And they have a saloon there and you can just kind of hang out there and you can buy boots if you want or you can just hang out and have like a bourbon if you want. So there are these brands that I watch and everyone's like, well, they do it so well. It's because they're really authentic doing it. And then I watch some other brands and people are like, well, what's wrong? Why does that not feel right? It's because they're copying somebody else. And I think today though, if you are building a brand, no matter whether you're a big brand or a small brand, you have to figure out the right message, the right medium, and the right messenger for your story. It may be a podcast or it may be the in-store experience. It may be the story about the authenticity of the boots and how they're made. It may, I mean James Purse, if for anyone who's watching who's ever met James, he is fanatical about making black t-shirts. You can make a version of a James Purse black but it's not going to be that because no one cares more about GSM counts or ribs the way James does. He's obsessed with this thing and because if you know, you know, people want to spend, are happy to spend a little bit more on a James Purse t-shirt than another brand because of that deep storytelling authentic connection. And I think it's easier now to do than ever before in the history of business.

Yeah, that was kind of fun, by the way, of me kind of showing you something as it was happening in real time. You can sort of see the Shopify product release cycle happening in real time, which is, it ended with ship it. That's right. Exactly. That's right.

So the announcement we just made literally while we're sitting here talking is that there are now millions of stores that are live Shopify stores that are alive right now on ChatGPT. Let's first talk from the consumer side because there are more consumers in the world than there are entrepreneurs. I say that begrudgingly, I wish there were more entrepreneurs but there's still more consumers. Years ago I remember meeting someone, I must have been 16 or 17 years old and it was a friend of a friend. And it was a very fancy older lady. And she told me this kind of the story of her personal shopper. And I was curious by this idea of a personal shopper. I didn't grow up with a lot of money. My parents certainly didn't have that. But I was like, explain to me what a personal shopper is. And she's like, oh, it's a very wonderful experience. You walk into, I think it was actually Nordstrom's, at least in the heyday of Nordstrom's, they were famous for having these personal shoppers. And it was all over the US. I think Neiman Marcus had it as well. Barney's probably in New York. But this particular woman in Boca Raton, Florida, had a personal shopper at Nordstrom's. And she said, well, I go in every Saturday and I go into this beautiful room and there's all these things that are laid out based on my specific preference, based on my size, color-coded based on everything else I have in my closet. It's all kind of put together for me and it's curated and I don't have to browse. It is pushed to me rather than me having to pull it. And based on what I decide to purchase on that particular day, the next round of personal shopping experiences, she'll have a different set. If I buy all black, maybe the next one is mostly white clothing. And if I buy some summer stuff, maybe the next one will be winter stuff. But this idea that a personal shopper knows everything about you, knows your preferences, your tastes, knows your size, was something that I think was limited to a very select few people in the world, people that could really afford it. One of the greatest parts of what we call agentic commerce, which is effectively having a conversation with a chatbot, whichever application you use, who knows a lot about you because it has all your search history as context. And then you saying, I'm looking for a product. Here's my price point. I need to deliver the next couple of days. What should I purchase? And then to have these agents, these incredible piece of technology go out in the world and look across all these Shopify stores to say that's the one. And that's the one not based on because that particular product is paying more for an ad, but based on this incredible thing called merit, that that product objectively has merit to that consumer. That's what makes us so exciting. That we're all getting personal shoppers that know everything about us and they're not showing stuff because the agent's getting a commission like probably some of these personal shoppers we're getting I suppose, but rather because it knows that I don't want to wear sandals. I've done research that I really like light hiking boots so don't show me heavy hiking boots. It knows that I prefer these colors because I've had thousands of these conversations with my ChatGPT or with any of my chat applications or with my Gemini applications. So, it knows so much about me and now it can curate and suggest things that it knows I want to buy. And then right from the chat, I can click it and this incredible in-app browser pops up and you're literally, it looks exactly like the Shopify store of that brand and you as a consumer never have to leave the chat and you can click buy and have it shipped to you. So from a consumer perspective, this is really exciting because we are all going to have much richer, deeper, more interesting experiences shopping, but we also can have great convenience. So the example I love to use is for Zoe's 7th birthday, Zoe's really into, my seven-year-old, she's really into rainbows and she's really into unicorns. Not surprising, she's a seven-year-old. So like everything we do is like rainbows and unicorns. When we want to have a birthday party for her, what I'll typically do is I'll go to one of the chat applications and I'll type in having a birthday party for Zoe. It already knows that Zoe loves these things. What do I need? And it'll be like you need tablecloths, you need decorations, you need streamers, you need countless things. And it'll say all these things are available to ship to Canada, which is where we live, and click here and you can purchase the whole thing. So, it's not just about discovering new brands, it's also about this incredible convenience. So, on the consumer side, I think shopping is about to become way more interesting. I also think you're going to be able to find brands that

Historically, you may never have found before. Typically, most consumers do digital shopping or e-commerce shopping through some sort of search engine. The search engine will show you things that are relevant, but often it will be big stores because they have higher trust signals. They know that if they show you Foot Locker, you're probably going to end up buying something, and therefore that's a good trust signal that you're going to complete a purchase. Some of my favorite sneakers are not from brands sold in these big retailers. They're more niche brands. It's something from Kith, for example, or it's something from 11y, or it's a pair of sneakers from James Purse, which most people don't even know James Purse makes sneakers, but they do. They make amazing sneakers. In fact, everyone's big on the Zenya trend and the triple stitches. Well, actually, if you look at the James Purse sneakers, they were running that style well before Zenya was.