#478: Harley Finkelstein on Entrepreneurship

Harley Finkelstein is an entrepreneur, lawyer, and the President of Shopify In this conversation, we discuss Shopify, the expansion of the digital economy, competing with Amazon, how he spends his day, digital as default, and the role for Bitcoin and crypto moving forward. ======================= OKCoin.com is the leading crypto exchange for both beginners and experienced users. You can fund your account in under 2 minutes, and get access to the most advanced trading engine, all while paying the lowest trading fees in the industry (0.1%). Visit www.okcoin.com/pomp and open your account today. ======================= Own crypto in multiple exchanges and wallets? Sync them to CoinStats so you track and manage them from one place. Track 8000+ coins and 300+ exchanges all from the Coinstats platform. Try it for free or go to coinstats.app/pomp and get 40% off your premium subscription. ======================= Pomp writes a daily letter to over 120,000 investors about business, technology, and finance. He breaks down complex topics into easy to understand language, while sharing opinions on various aspects of each industry. You can subscribe at https://www.pompletter.com =======================

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

• 0:00Anthony Pompliano?

  What's up everyone, this is Anthony Pompliano. Most of you know me as Pomp. You're listening to the Pomp Podcast, simply the best podcast out there. Let's kick this thing off. Harley Finkelstein is an entrepreneur, lawyer, and the president of Shopify. In this conversation, we discuss Shopify, the expansion of the digital economy, competing with Amazon, how he spends his day, digital as default, and the role for Bitcoin and crypto moving forward. I really enjoyed this conversation with Harley, and I think you will as well. Before we get into this episode, though, I want to quickly talk about our sponsors. First up is OKCoin. They're a leading crypto exchange for both beginners and experienced users. You can fund your account in under two minutes and get access to the most advanced

• 0:45Anthony Pompliano?

  trading engine, all while paying the lowest trading fees in the industry, 0.1%. So if you want to use a regulated US-based exchange that is good for both beginners or experienced users and has the institutional trading engine that you're looking for, but is as easy as anything else to get your account funded and start trading today, head on over to okcoin.com/pomp. Again, okcoin.com/pomp and open your account today. OKCoin.com, a regulated US-based exchange that'll get you started in just minutes. OKCoin.com/pomp.

• 1:25Anthony Pompliano?

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• 2:10Anthony Pompliano?

  Go use CoinStats, coinstats.app/pomp, coinstats.app/pomp, and you can either use the product for free, or if you want to use the paid subscription features, you'll get 40% off that paid subscription. CoinStats.app/pomp, go check it out. Don't forget that I also write a daily letter to over 120,000 investors about business technology and finance. I break down complex topics in the easy to understand language while sharing my personal opinion on various aspects of each industry. You can subscribe at pompletter.com. Again, pompletter.com. So if you want to buy and sell crypto, go to okcoin.com. If you want to keep track of all the crypto that you own,

• 2:55Anthony Pompliano?

  go to coinstats.app/pomp, okcoin.com/pomp, coinstats.app/pomp, and pompletter.com. All right, let's get into this episode with Harley. I hope you guys enjoy this one.

• 3:07Speaker 01

  Anthony Pompliano is a partner at Morgan Creek Digital. All opinions expressed by Pomp or his guests on this podcast are solely their opinions and do not reflect the opinions of Morgan Creek Digital or Morgan Creek Capital Management. You should not treat any opinion expressed by Pomp as a specific inducement to make a particular investment or follow a particular strategy, but only as an expression of his opinion. This podcast is for informational purposes only.

• 3:33Anthony Pompliano?

  All right, guys, bang, bang. I've got Harley here with me. Thank you so much for doing this, sir.

• 3:36Speaker 02

  Thanks for having me, Pomp. It's great to be on the show.

• 3:39Anthony Pompliano?

  Absolutely. Let's jump right into your background. Obviously, you haven't been running Shopify forever. So let's just start kind of from the beginning. Where'd you grow up and how did you get to the president of business?

• 3:48Speaker 02

  So born in Montreal in Canada, grew up in South Florida, moved down there when I was a kid and ended up going to McGill University when I was 17, so I moved back to Canada in 2001 and had no plan on becoming an entrepreneur per se. I was always entrepreneurial, but never really planned to be an entrepreneur. 2001 September, I moved to Canada. My parents are still in Florida and unfortunately, stock market goes sideways. Everything goes really, really sideways for my family. My parents lose everything and mom calls and says, your dad's not around anymore. We have no money. You should come back down to South Florida. And I don't know if you've ever been to Montreal, but it's just this amazing city. It's sort of like, you know, it's, it's this European enclave in the middle of Canada.

• 4:32Speaker 02

  And it's just amazing and interesting. And I was 17, I want to be by my, I want to stay on my own. So I tried my hand at a couple of different jobs. I've been DJing since I was a kid, so I DJed on weekends and I tried to sell vacations. Nothing really allowed me to subsidize my income and help my mom and sisters. A friend of mine told me that McGill University spends a bunch of money selling T-shirts or giving away T-shirts and that I should go to the T-shirt business. I knew nothing about the T-shirt business, but I thought that was a really interesting idea. Montreal has this long history of T-shirts and the apparel industry. And I thought that I would be able to kind of navigate that. And ended up starting this little T-shirt business, making T-shirts for universities, sort of the promotional products that they sell in the bookstore and that they give out in the orientations.

• 5:16Speaker 02

  And, uh, and ran that business all throughout undergrad. A mentor of mine, I had mentors, I was small, we can talk about that later. Mentor of mine convinced me to go to law school, not to become a lawyer, but to become a better entrepreneur. And this particular mentor was teaching law at the University of Ottawa, which is the capital of Canada. And so I applied to one law school in Ottawa, moved here in 2005 and didn't have a friend or a family member, didn't know anybody here. I'd never even been to Ottawa, but I came here for school. And I started asking where the entrepreneurs hung out. Those were sort of my tribe. Those are the people that I always hung out with and I want to sort of meet other like-minded people. And I was directed to this random coffee shop in Ottawa where five entrepreneurs hung out every Friday night.

• 6:01Speaker 02

  And frankly, they just commiserated with each other. They shared best practices. They talked about things that they had discovered about their businesses. And, and I just joined up with that group. And one of the entrepreneurs that was part of that group was Toby. Now, this is 2005. So Toby, a year earlier, had wanted to sell snowboards on the internet. And so in 2004, there were two ways to sell something on the internet. One way was to sell on a marketplace like Amazon or eBay or something like that, which although it was inexpensive, it didn't allow you to build your own brand. You were effectively renting customers from those marketplaces. You didn't have a direct relationship with the end consumer. But the other way to build a beautiful, scalable, unique

• 6:44Speaker 02

  online store, it was really expensive at that time. And we're talking about like Magento, ATG, Hybris, WebSphere, these really big investments. And he didn't have that kind of money. So like any good entrepreneur, if you don't like the two options, you generate a new option. And his new option was to write a piece of software to sell these snowboards. And that was 2004. By 2005, he realized that people actually may really benefit and value the software to sell their own products. So that the the snowboard business was a good idea, but the software behind that snowboard business may be a great idea. And that's around the time that I met Toby in 2005, and I ended up becoming one of Shopify's first merchants. I took my B to B t-shirt business and turned into a B to C online t-shirt retailer. And after I finished law school and business school, I called Toby in 2009 and said,

• 7:29Speaker 02

  that piece of software that you had built, that you had written, gave me independence. It helped me find my life's work. It was effectively a superpower for an entrepreneur. And I wanted other people to have that same experience. And that was about 11 years ago.

• 7:44Anthony Pompliano?

  How did the t-shirt business turn out?

• 7:47Speaker 02

  We shut it down around this time I started at Shopify. I found that fulfilling t-shirt orders and in the early days of any company, as you know, it's you're kind of a Swiss Army knife. And so I was sort of the first non engineer at Shopify. And so my job was do effectively everything that the small handful of engineers don't want to do. And it just got too, it just got too busy. So it's actually, I'm not going to give it out because I know you have a big audience and I don't want everyone sort of DDoSing my t-shirt shop. But it is still there for nostalgic reasons. But I no longer sell t-shirts, although I am obsessed with t-shirts and hoodies, as you and I have discussed in the past.

• 8:21Anthony Pompliano?

  Absolutely. So where, what we discussed was you wear black t-shirts and black hoodies. I have a black hoodie on because I pretty much wear that every day as well. Where did your obsession with black t-shirts and black hoodies come from?

• 8:35Speaker 02

  I always felt, so I, after law school, I, I articulated for 10 months, which is effectively the, the, the process to get called to the bar to become officially a lawyer. And the dress code at this law firm, it was a law firm in, in Toronto, was obviously, you know, a suit, suit and tie every single day. And I always found it ironic that they, they were pushing this idea of wearing a suit and tie every day because most of the lawyers didn't look good. It looked like they were wearing their dad's jacket or the tie wasn't done up properly. The suit didn't fit well, but yet that's what they were dictating that lawyers wear, even though lawyers didn't look very good. And I remember when I got to Shopify, I, I just, I wanted, I wanted nothing to do with the suit anymore because the suit had this negative connotation for me.

• 9:19Speaker 02

  Uh, and I wanted something that I think to your point, I know you believe this, I wanted to reduce the cognitive load of selection every single morning. I wanted something that looks good, that feels good. And so, um, ended up discovering and actually meeting James Purse from James Purse, the brand. And what I loved about James Purse from a, a product perspective was I'm not a small size, I'm not a medium size, I'm kind of in the middle. And James Purse does this zero, one, two, three, four, five kind of sizing. Uh, so he has sort of these half sizing. And then I think a couple of years, maybe around 2013 or 14, I realized that wearing a T-shirt during Canadian winters just didn't work. I was just too cold. So I found these hoodies from a company called Blue Salt, which is a great entrepreneur,

• 9:59Speaker 02

  uh, Lindy, who's out of Malibu, and she created actually like machine washable cashmere hoodies. And, uh, so between James Purse T-shirts and machine washable hoodies from Blue Salt, that's my wardrobe.

• 10:10Anthony Pompliano?

  Uh, well, now you know where I'm going to go, uh, since we finished this up. Uh, let, let's talk a little bit about, uh, when you first started Shopify, um, you understand that you're building a business, you understand that you kind of have grand visions. Did you guys ever think you could build a hundred and plus billion dollar business and kind of have it grow into what it's become today?

• 10:30Speaker 02

  You know, I think Shopify was incredibly misunderstood for a very long time. I think we were underestimated certainly, but also misunderstood. You have to understand that the market, I remember some of the early VCs that we met with when we were first thinking of raising our series C, excuse me, our series A, well before our series C or series A, would tell us that the market's just not big enough, that the total addressable market for ecommerce software was very, very small. And I think what a lot of folks missed, forget about Shopify, but just the Shopify market, was that the pie itself, like we wanted a bigger piece of the pie, but we were also expanding the pie itself.

• 11:08Speaker 02

  And that the market for folks that wanted software that makes more than cost was far bigger than any spreadsheet would, would, would, would, would describe. So the idea initially was anyone that wants to sell something online can, and they can build a beautiful online store for $29, and it's going to be customized to their brand. It's going to be scalable. It's going to have all the things they, they, they need. But it wasn't until, I think around 2014, 2015, kind of, you know, a year or two before the IPO, that people began to realize, wait a second, this is, this is different. What, what Shopify is doing is they are trying to create new entrepreneurs. We're, we're giving software to existing entrepreneurs and making sure that they can run, scale, build businesses more effectively.

• 11:50Speaker 02

  But what we're also doing is we are expanding the definition and the pool of people that self-identify as entrepreneurs. And, and so, no, I, I don't think people understood it. I think we knew that there was something really special here. It's the reason why, certainly Toby and I, but our team, you know, this is our life's work, this idea, you know, every 52 seconds, this is interesting. Every 52 seconds, a brand new entrepreneur gets their first sale on Shopify.

• 12:16Speaker 02

  And the reason that I think is so interesting is not, I mean, you hear us talk about Kylie Jenner building a billion dollar brand on Shopify, right? Or Allbirds, or Bombas, or Tommy John, or Fashion Nova, or these, you know, Kit, these amazing companies that have built huge businesses from their mom's kitchen table all on Shopify and never, never had to leave and never will leave. But it's those, those merchants that make that, the first time entrepreneurs who commercialize their hobby, who need to make more money, especially during a pandemic, who hate their job and want to find a way to self-actualize and be creative. And I think this idea that Shopify is becoming the entrepreneurship company, that is something that people are just beginning to understand.

• 12:55Anthony Pompliano?

  So when you think of that, like, there's the what I'll call storefront, which is just, hey, we give you some software and you can set up a store, you can sell things on the internet. How else does that kind of manifest itself? Are there other things that you guys think go into that bucket of just, we're going to take individuals and help them transition to self identifying as an entrepreneur and how that will kind of show up in the software?

• 13:14Speaker 02

  Yeah. So if you sort of think of the product of Shopify in different chapters, chapter one was make it really easy to open up an online store and start selling to a global audience. And that was something that we knew was needed. We knew that folks couldn't do it. It was too expect. You either needed to be an engineer or you need a lot of money to build your own online store. There was some open source software when we got started, but it was very, very complicated. And I get it. While the marketplaces do play a role, you don't have a direct relationship with that marketplace. The marketplace effectively is renting you these customers. And, and, and so if you want to have a real brand, you want to build something, that's not a great solution either. So step one or chapter one was build an online store. And then one of the things we began

• 13:56Speaker 02

  to realize was that there are these things that every single merchant needed when they were starting an online store. So for example, payments. So we created Shopify payments, I think around 2012, 2013, so that anyone who's starting on Shopify would immediately have a merchant, a merchant gateway, a way to transact credit cards in real time. And, and the rates that they would get would, would be better because we would leverage our economies of scale. And then sort of the next chapter was, okay, where else are people selling? Well, people are selling offline as well. And so the next product we brought out was this Shopify point of sale, Shopify retail, so that you can sell in an online store and an offline store, and it all feeds back in one centralized back office. And then that has sort of evolved and expanded to what I, what I think is,

• 14:39Speaker 02

  and we don't really use this term much, but it's worthwhile mentioning, this idea of Shopify being a retail operating system. And where you have this centralized back office, where you have your inventory, and you have your marketing tools, and you have your shipping and fulfillment tools, and you have reporting and analytics, and everything you need to run the day to day. And one major channel, one major sort of spoke is online store, one other spoke may be offline, but maybe you also want to cross sell on Instagram, or Facebook, or Pinterest, or Walmart, or Amazon, who are also channels of ours. And then what you, if, when you zoom out, what you realize is

• 15:14Speaker 02

  The future of retail, if you believe it's retail everywhere, which we do, we think the future retail is where consumers want to purchase, then what we're trying to build is we want to connect merchants and brands with consumers wherever they might be. And along the way, we've added things like capital, we've given out about a billion dollars of capital to small businesses, we've added the Shopify fulfillment network, which I know you want to talk about later, which I'm happy to talk about as well. We've added things like Shopify balance, which makes things like cash management easier. And this just continues and continues. And so what you end up with is that every pain point that an entrepreneur may face, we're trying to reduce that. We're trying to level the playing field so that someone that has a great idea can become

• 15:55Speaker 02

  the next Allbirds, the next Bombas, and they can do so without ever having to leave Shopify.

• 16:01Anthony Pompliano?

  Yeah, one of my favorite parts about the entire company's story is just this idea that you guys continue to arm the rebels, right? And I know you guys talk about it and have really built it in the software. When you think through that, obviously, one of the elephants in the room is Amazon. And they're this, you know, big, massive business that seems to be dominating the world, and people read all these stats. And it was almost like, you know, Shopify was almost an afterthought for a while. But I think over the last couple of years, people have woken up. And to your point, maybe it was a misunderstanding of what you were going after. And then two was a size thing. And now that you're more than a hundred billion dollar business, people start to say, wait a second, like, this is a massive business, this market is way bigger than we thought.

• 16:43Anthony Pompliano?

  And also, the Shopify platform is very, very compelling when compared to some of its competitors. So how do you think about, you know, where you pick the battles to fight against competitors, whether it's Amazon's, you know, FBA, whether it's like delivery, fulfillment? There's just so many different things that go into this mission of arming the rebels and really helping them be successful entrepreneurs. How do you just prioritize and decide when to actually go and work on something versus when maybe it's just not a fight worth fighting?

• 17:13Speaker 02

  So right now, as we sit here, Shopify is the second largest online checkout in America. So Amazon is the first largest, the second would be Shopify. That's pretty cool. It's really cool. Yeah, I mean, it's, I mean, I'm sort of saying it like as if you like, as if it's so normal, but, but that is incredible. Now, the reason it's incredible is as follows. It is, it's not a flex. It isn't like, look how big we are. The reason that we're so proud of being the second largest checkout is because if you were to pretend for a second that we were a retailer, we were a store, when we would go to a payment company or a shipping company or any supplier in our, in our ecosystem, in our, in our universe, as a retailer, we would have this massive economy of scale.

• 17:55Speaker 02

  We would walk in with gusto and the confidence and frankly, the leverage that the second largest retailer in America would walk in with. But the difference is that we still do that, except we don't keep those economies of scale for ourselves. So when we talk to payment companies or capital companies or fulfillment companies, we, we, we want the same thing that they would give the second largest retailer. But rather than keeping those and using those, we give those to every business that starts on Shopify. And that means that the moment you start on Shopify, the access you have to all the different things you need to run your business, you were getting them at this incredible scale because you're part of this, you know, larger platform, this larger community of over a million Shopify stores.

• 18:37Speaker 02

  So the more scale we have, the better we can arm these rebels, the better those rebels can compete. And more of those, you know, what would have been insurgents can become really incredible incumbents. I mean, it's, I don't know this for a fact, but I assume at some point in the Nike boardroom, they're talking about Jim Shark and they're talking about Allbirds. That is amazing. Think about that, like those companies did not exist six years ago and now they are leaders in their category. That type of growth and scale never happened in retail. It took generations for you to get that sort of scale. And now that's happening very, very quickly. And we don't take any credit for Allbirds' success or Jim Shark's success, but we've given them the tools so they can do so really quickly, really effectively. And so that's sort of the first part. The second part is.

• 19:23Speaker 02

  All these marketplaces and just, you know, from Shopify as a merchant, you could cross sell directly from the admin on Walmart or on Amazon or on eBay or certainly on all the social media platforms because that's where consumers are. That's where they're hanging out. If this was 100 years ago, you would want to sell in a town square. That's where the baker sold bread and that's where the cobbler sold shoes. That's where people were hanging out. But because consumers are hanging out everywhere, the responsibility that Shopify has to our merchants is to make sure they can sell anywhere. But the reason that folks often sell on some of these marketplaces beyond just getting access to that audience is because they don't know how to get fulfillment on their own. So they can use FBA. They don't necessarily know exactly how to get great rates on payments.

• 20:07Speaker 02

  So they want to use, you know, pay with Amazon or they want to use the one click checkout. But all of that is now being made available without needing to ship your product with someone else's brand on the box like you would with FBA. If you use a Shopify fulfillment network, like let's say Hedonist for example, you now have Hedonist boxes that are going out. You still get economies of scale. We're still shipping it on your behalf, but now your brand is what the consumer is interacting with. And what we try to figure out is where do we have an unfair advantage? So capital is a great example. Small businesses notoriously have trouble getting capital. It's just banks don't like to lend small businesses. They don't have a lot of assets. They don't have a lot of collateral to put down. And a lot of the banks don't have access to information to make a smart underwriting decision.

• 20:52Speaker 02

  But we do, we understand the size, the value, the health of each of those businesses. And so we can make much better, more effective underwriting decisions, which then gives these merchants, these loans and cash advances they can spend on marketing and on inventory. And I think all of that in aggregate, in aggregated, what you, what you end up with is a much more fair playing ground for these DTC brands, these entrepreneurs to compete. And, and I think that that's what we're seeing. And as we sort of finished Black Friday Cyber Money 2020, what we saw is on the demand side, consumers also changed how they're playing now. Consumers voted with their wallets unequivocally in the, in Q4 of 2020. Of 2020, we saw this during Black Friday and Cyber Monday and throughout the holiday

• 21:37Speaker 02

  season that they would prefer to buy from independent businesses, assuming it's as convenient, as easy, as pleasurable. And it is. One click checkout is now is now offered on shop with shop pay. The ability to fulfill properly, we can help with that. The ability to have a beautiful online store, we can help with that as well. Or cross sell on Instagram, we can help with that too. And I think what we're what we're talking about here is probably some of the most exciting times of retail of the last 100 years are happening right now.

• 22:04Anthony Pompliano?

  Why do you think the consumer kind of trend has shifted? Is that something where these independent brands are getting better at marketing and kind of customer acquisition? And they're going where the consumers are? Is it something where consumers are almost kind of silently protesting and they don't want to go to some of the centralized marketplaces? And they want to go direct? Like, what's driving that shift? That's very interesting.

• 22:26Speaker 02

  I think part of it is that, you know, it just something like, you know, one click checkout, that a consumer may have been frustrated a couple of years ago, that if I'm buying off an independent store, the checkout takes, I don't know, 30 seconds or 60 seconds, takes a full minute. Whereas on some of the marketplaces with one click checkout, it's much more convenient. And so even though they know and they feel they want to support those those independent businesses, and I think the way a lot of them think about it is, when I buy something from an independent merchant and independent entrepreneur, I am voting with my wallet for that entrepreneur, for that brand, for that product to exist in the world. And I think we all, at our core, want small businesses to exist. In fact, you know, we're in the middle of a pandemic right now. And I think all of us agree that on the other side of

• 23:10Speaker 02

  the pandemic, for our communities, our cities, our places where we live, to be interesting, to have culture, we need independent businesses to exist. So we as humans, I think, and consumers want these things to happen. But if it's really inconvenient, we may not always make the right decision. We may decide to go buy it off a big department store or a big marketplace. But again, Shop Pay or Apple Pay or Android Pay, if you've ever used Shop Pay, but Shop Pay to me is the greatest way to check out on the internet. It's not only fast and convenient and safe, it just, it takes no time. It's a pleasure to use. It's quite unbelievable. And so as you begin to take away some of the value that those big department stores or big marketplaces have, and you replicate that and you give it to the hands of the rebels,

• 23:53Speaker 02

  you see consumers shifting their buying preferences. And the other thing is, from a, from a brand perspective, there is a tension between some of the marketplaces and the brands. They see a product that looks just like theirs, and it wasn't there a week ago. And why is it there now? Like, they just had some success in the marketplace and now they're being, you know, someone's competing with them. There is, we are merchant obsessed. All we care about is helping merchants. And I think a lot of the department stores or, or some of the marketplaces have a very different obsession. Maybe it's on the end consumer. And so they, not that they don't care about the merchant, but the, you know, the primary stakeholder for them is the end consumer. And I think we can still handle, make sure the end consumer has a great experience, but care about the merchant.

• 24:36Speaker 02

  And then I think probably the final point is, I don't want everyone wearing the exact same black hoodie. I like the fact that I can browse amazing direct to consumer brands and brands in general, and find something that is uniquely me, that fits me, that looks good on me, that, and I can support all the people behind that business. And that, I think is, I'm not sure COVID changed that, but something is different now, certainly from the consumer side, where if possible, I'm always going to buy directly from an independent business.

• 25:04Anthony Pompliano?

  Yeah, that's a great perspective. When you started, you literally did everything that was non-engineering, it sounds like. And today, you obviously have many, many more employees and kind of entire organizations. I'm a big believer that what you spend time on is kind of a prioritization or a proxy for that prioritization. How do you spend your day today? Like, what does a normal day look like for you across all of these different products and orgs and, you know, kind of the now versus what your guys are building in the future?

• 25:31Speaker 02

  Yeah. The neat part of Shopify is that it feels, so I've spent about a third of my life at Shopify. I'm in my mid 30s. I've been here for 11 years. It's a long time and I hope to stay here the rest of my life. It's just, it, the mission of Shopify, which is to democratize entrepreneurship, to arm the rebels, to make commerce better, is so, the Venn diagram overlap with my own personal interests is completely, you know, is completely overlapped. And part of it is, you know, I think entrepreneurship was always a way for folks to survive. And now I think it's a way for folks to survive and to do something that is really interesting and exciting to them. And so many of our, I mean, my grandparents immigrated to Canada in the 50s.

• 26:11Speaker 02

  They didn't call themselves entrepreneurs. My grandfather started a little egg stand selling eggs at a farmer's market because he needed to survive. And the idea that entrepreneurship should be accessible to everybody and anyone that has a hobby should consider commercializing that hobby and anyone that has a passion should consider about sharing that passion with the world. A lot of what I'm doing right now is trying to tell that story, is trying to ensure that more people consider entrepreneurship. And they may not try it with Shopify, although more and more people are, you know, using Shopify to start their entrepreneurial journey. But I, so right now, it's a lot, it's a lot of that. I want people to understand that entrepreneurship is not complicated

• 26:54Speaker 02

  and it is not expensive and it's not out of reach, that it is accessible. And whether you sell two products a day or two products a second, you know, or you take your, you know, your YouTube channel like Jeffrey Star did and turn that into a Shopify store and completely disrupt the cosmetic industry and you're competing against Sephora. That's what, that's what I'm excited about. I'm trying to spend a lot more of my time right now inviting more people into this idea that entrepreneurship is this great way to, to find your life's work and to find independence. In the past though, what's, because Shopify is growing so fast, it's a little bit like the Red Queen race. Are you familiar with that term?

• 27:32Anthony Pompliano?

  I am.

• 27:33Speaker 02

  Yeah. So the neat part about becoming like Shopify is because it's growing so fast, if you simply, as an individual, grow as fast as Shopify, there is no, there's no delta, there is no alpha, there is no way to continue to do your job and to re-qualify. And so what I love about Shopify is that over, over, over the years, There's always this big, interesting, new problem that I get to solve. In the early days, it was how can we invite larger merchants to come on to the platform with Shopify Plus? Then it was, okay, well Shopify's core offering does what most people need most of the time. How do we ensure our product has everything that any merchant might need, no matter what vertical they're in? And that created the App Store and the Shopify Partner Program.

• 28:14Speaker 02

  The IPO was something that was completely new to us, new to me. I'd never, obviously, taken a company public. I didn't even know what that was. And getting good at not only taking the company public, but then running a publicly traded company and not letting things like quarterly earnings be a distraction to the vision. There is no shortage of those big challenges. And the way that I sort of view these challenges is that I need to requalify for my job every year, which means that I have to run faster and grow faster than Shopify does. And that is incredibly difficult and incredibly rewarding.

• 28:47Anthony Pompliano?

  Talk a little bit about COVID, and maybe not so much in what changed for merchants and for consumers, but inside of the organization. My guess is that you had to go remote. And so there's all sorts of things around. How do you continue to scale the team? How do you continue to keep the company culture? Just talk through kind of how you as an operator and some of the obstacles and workarounds that you guys figured out to make sure that the company kind of stayed on the trajectory that it was during COVID.

• 29:16Speaker 02

  That's a tough one. It's a tough one. It's... When COVID hit, a couple of things were apparent to us. Even before COVID hit, right now, you and I are talking, and there's two squares. There's the Palm Square and the Harley Square, and we're next to each other. And it would be great if you and I were in the same room together. We would feel the energy, maybe I would notice particular body language or voice inflection, or I would, you know, there would be nuances of the conversation that would be difficult for me to pick up right now. But what was happening more and more was that when I was joining a meeting, there would be three or four squares, you know, Google Hangout or Zoom or whatever. And in one square, there'd be one person. The second square, there'd be

• 29:59Speaker 02

  a second person. Then another square, there'd be three people together. They'd be in the same location. That to me is the worst model. So best model, everyone's in the same room. Very difficult to do that, though, when you're, you know, five, six, seven thousand people across seventeen different locations. So the best case is everyone in the same room. The worst case is some of people are in the same room, some people are not in the same room. And so we had already been feeling a little bit like there, there needs to be a better model here, which allows us to continue growing, but scaling communication scale and the way we interact with each other. And then COVID hit and we said, look, we're going to go digital by default, which doesn't mean we're never going back to an office, but it means that Shopify's office centricity is over, that going forward, we will use offices and leverage

• 30:43Speaker 02

  offices for things like onboarding and planning. And when we need to get together to do something really difficult and, and where being in person really, really matters. But generally, we're going to be a digital by default company. And COVID sort of accelerated that. And as someone that is a, you know, a power extrovert, that was really difficult for me. I, I felt lonely. I felt my anxiety levels, I've had anxiety since I was a kid and I, I've gotten pretty good at managing that, but my anxiety levels were dramatically elevated because I didn't feel that energy. And my wife's an entrepreneur as well, and, and she was feeling that way too. And so it took a while to sort of recalibrate on a personal level, how I can still get energy, how I can still connect with people in a way that

• 31:28Speaker 02

  is meaningful, that is authentic, even though it may be digital. On the merchant side, we told everyone, I think it was like March seventeenth or March eighteenth, twenty twenty, throw out your plans for the year. Whatever you were planning to do, whatever your roadmap was, it doesn't matter. The only thing that matters is helping entrepreneurs that use Shopify survive and, and, and get through this thing. And so within a couple of days, we extended capital to, we were just doing capital in the US, we extended capital to small businesses in the UK and Canada. We added a gift card functionality. So service-based businesses can also use Shopify. We recreated, we, we added functionality to point of sale so that anyone that had us in their brick and mortar store can easily transition to local pickup and

• 32:13Speaker 02

  Curbs I pick up in local delivery. So a bunch of stuff we did really, really quickly to get to get to help small businesses. And what I hope, you know, the the Irish Prime Minister had this great, I think his Irish Prime Minister. He had said during COVID, he said, let the world see that when when the world was at its worst, we were at our best. And I hope, you know, the legacy of Shopify during COVID was that we really, you know, we not only put out new products and really developed functionality so that entrepreneurs and small businesses could survive this thing. But we showed up as the entrepreneurship company and that that's my hope of what, you know, what will be. When people look back on what we did, that's what they see.

• 32:53Anthony Pompliano?

  Yeah, I mean, you guys did a fantastic job from somebody who, you know, kind of watched from the sidelines. It was absolutely amazing to watch. So one, thank you, but also congratulations on all that success. I want to switch gears a little bit and talk about something that a lot of people who listen to this podcast will be interested in, which is digital currencies and kind of the digital economy. I've got this theory that, you know, every local economy or kind of nation state economy has their own commerce, their own currency, their own regulations. And you kind of just go through what makes an economy an economy, but it's all tied to a physical or analog space and a geographic boundary.

• 33:33Anthony Pompliano?

  We're obviously watching kind of the build out of a digital economy that necessarily isn't tied to those geographic spaces. And so if you think of what you guys have built, it's basically digital storefronts. And you could imagine kind of a main street and you guys have been a huge part of that. But there's also other elements to that digital economy, whether it's digital currencies or other types of technology. And so just how do you see kind of the world evolving? And is this something where you will continue not only to be, you know, digital as default internally? But also it's just how do we incorporate everything from digital currencies to decentralized technologies, privacy centric technologies, or just any thoughts there on that like digital economy thesis?

• 34:14Speaker 02

  So November 2013, plus or minus one month, but I'm pretty sure I'm close to that. Okay, the year 2013, we actually enabled, we enabled merchants to be able to accept Bitcoin. And this is

• 34:29Anthony Pompliano?

  That was early?

• 34:30Speaker 02

  Yeah, it was early. That was definitely early. And not just that, but I actually remember the first store that made a sale using crypto. And I don't know if the store still exists. I'm sure all of your listeners will be checking out, but it was actually SMS by 50. It was 50 cents headphone store. So this is around the time where Beats by Dre just came out. And I think there was a lot of attention around combining, you know, celebrity culture with hardware and stuff. And so Beats comes out, does really well. And then I think it was called SMS by 50. I mean, I think that's what the name was. And they enabled, they enabled Bitcoin. And so I don't look, it is not necessarily something that a lot of people are using, a lot of consumers.

• 35:11Speaker 02

  It's not as if a lot of consumers are using crypto or Bitcoin to buy stuff across all the Shopify stores. But our merchants can accept it if they want. And it's kind of neat trivia to know that 50 cent was one of the first guys to do that. But our view, like, you know, we're a member of the DM Association, which is, you know, sort of formerly known as Libra. We believe in a world with more choice, more entrepreneurs, not fewer. And, you know, I think our merchants data is not belong to Shopify. The way that we view data is our merchants data is their data, it belongs to them, they own it. The only thing that we can do is, is, is, is give them insights based on that data so they can make better decisions. And I think that, you know, this idea of trust is sort of at the core of everything that we do.

• 35:55Speaker 02

  And it's a filter for every decision that we make. But I think the rules of the internet are changing. I think whether you look at advertising or data collection or currencies, as you brought up, entrepreneurs need to be ready. And Shopify has a responsibility to make sure entrepreneurs have the very best tools to build relationships with customers. And so you're seeing this with Facebook's Novi and DM and Apple's changes to the advertising landscape. So part of our responsibility is sort of the guardians of the world's entrepreneurs is to make sure in the same way that, you know, as soon as Instagram was talking about commerce. We wanted to make sure that we were going to be the launch partner for that. Or when we heard that Walmart was going to open up their marketplace of third-party sellers, we want to make sure that that day merchants were able to go ahead

• 36:38Speaker 02

  and cross-sell on Walmart, or Apple Pay was available. We feel the responsibility and the weight on our shoulders that if merchants are going to put the trust in us and going to put their business on Shopify, then the onus and the responsibility is that we have to always show up with the most current ways to process, to do business, to interact with consumers. And I think crypto will play a role in that when it goes beyond just to store value. And I know you talk a lot about this, and I really like the way you think about decentralization and crypto in general. But our responsibility is not to say, here's how to do it, rather to give them the tools that they may want so they can make the best decisions. And that's the difference between being a real platform and being an aggregator.

• 37:20Anthony Pompliano?

  Yeah. And how does that play? Because I think that's a really interesting way to look at it. It's like, hey, we're going to basically build this toolbox. It's got a bunch of tools in it. You, as the operator, meaning the storefront or the business owner, you can choose to use whatever you want. You want to accept Bitcoin, knock yourself out. If you want to accept US dollars, you know, knock yourself out. It's kind of your choice. I think that that optionality is obviously very valuable for a lot of business owners. How do you think about some of the stuff that we're seeing? And I don't want to get into specific examples, but there's all these questions now about everything from privacy to data to deplatforming. And it just feels like, I'll say, the crowd. And really, that's just a blanket term for people outside of your company. Everyone has an opinion, right? And some of the opinions, maybe you agree with

• 38:04Anthony Pompliano?

  some of them, you don't. But just how do you think about hearing the opinion, maybe, but not necessarily always following what the opinion is, but also understanding that like listening is a key part of it. And it just feels like, as an operator of a large business, especially a platform business where other people are relying on you, some of these responsibilities are shifting a little bit. And so just any thoughts on kind of how that's evolved over the last, you know, maybe even two, three, four, five years?

• 38:32Speaker 02

  For us, the way we've always looked at it is that companies, company culture, company decisions are very much based on the people that are making those decisions. And one way to ensure that you are running a scalable company that makes good decisions is to systematize things. So years ago, you know, there may have been particular stores on Shopify that some people liked and some people didn't like, and some people thought were offensive, and some things weren't offensive. And one side loved these stores, and one side hated these stores, and vice versa.

• 39:05Anthony Pompliano?

  Welcome to the internet.

• 39:06Speaker 02

  That's exactly right. Welcome to the internet. I mean, just go to Twitter, anything, and post something that you think is completely non-controversial, and you'll see how quickly it is controversial. And so one of the things that we did early on in the last couple of years, not that early on, but the last couple of years, was we created this thing called the AUP. And it's a very simple document, but a very important document. It's the accessible use policy. And what it does is, it sets out a list of things, a list of terms that are prohibited, actions, products, connections to the owners of the store. It sets out what is prohibited on Shopify. And, you know, one example, it prohibits the promotion or the

• 39:47Speaker 02

  support of any organization, or any platform, or any person that threatens or condones violence. It's just an example of the AUP. And then we have a team, it's called Trust and Safety, and they both do it manually, but also using great software and using machine learning. They can go through a thorough and rigorous assessment to figure out which stores contravene the AUP. And it is not easy work by any means. And the team, I think, that team in particular, has a very unique expertise that is of critical value to Shopify. But when a particular merchant or store crosses that line, and we can say objectively, this contravenes the AUP, they're gone. And that's the end of it. And I think one thing that

• 40:28Speaker 02

  a lot of companies are trying to avoid is systematizing it. It is nuanced, and the AUP probably, you know, one example I'll give you is Ghost Guns. Ghost Guns, if your policy, your terms of service are effectively a proxy for legality.

• 40:48Speaker 02

  And you rely on the law to dictate what's allowed and what's not. The law doesn't catch up very quickly. The law is, there's legislation, there's common law, which is based on case law and precedent. So saying, well, you know, if it's legal, we're going to allow it is actually not that effective because something like ghost guns come out and all of a sudden there's this new category of weapons that is not technically against the law, but to us feels incredibly wrong. It contravenes our AEP. Systematizing these things make it easier. And it's, I'm not saying it's, we did it perfectly or our system is flawless, but it is the best way that we have learned how to govern these type of conversations, these decisions. And it's made it easier for us to be as objective as someone can be.

• 41:33Anthony Pompliano?

  Yeah, the one thing I'll add to this is I don't think many people who have, don't, haven't had the, both the pleasure and also the headache of working inside a large tech company that's scaling very quickly is there's this understanding like you're not going to get it 100% right 100% of the time, right? And so it's, you're going to try to do the best you possibly can in every single situation. But obviously there is going to be edge cases and nuance and all of that stuff. And so.

• 42:00Speaker 02

  But the answer is, the answer is don't not try. It's right. The answer is it's complicated, so don't like I'm doing nothing. No, the answer is to try to find the system with the fewest amount of trade offs, the system with the fewest amount of flaws. And it's never going to be perfect. And then to look at that as a dynamic system whereby you can add things that they come, you know, we had legalization of cannabis in Canada two years ago, far, well before most other countries, certainly before the US on a federal national level. That stuff is nuanced. And so there is a way to create systems that get better over time, where you learn from, you know, you learn and you watch how laws are evolving. And that's what we're doing. And I think it's, again, it's not a perfect system, but it gives us a framework for making decisions that I think are objective and people can criticize, but at least they understand

• 42:46Speaker 02

  why we decided to do something.

• 42:48Anthony Pompliano?

  I think that's, that's the best way to be. I've got five questions I want to kind of run through in a lightning round that you'll get to ask me one to finish up. The first two are Shopify related. First being, what is your favorite customer story? Like that one that just, for whatever reason, it's stuck with you over the years and you're like, you know, this is amazing. This really kind of embodies what we want to do at Shopify.

• 43:09Speaker 02

  So I have a bias because we have more than a million stores on the platform, but I personally know, and this is part of my job, I personally know a lot of our stores and I know their their origin story and and there are particular merchants that I met when they were just getting started and they just, I don't know, I it's it's it there's there's this paternal pride almost. And I mean, maybe that sounds patronizing, but it's not meant to be. And one of those stores is one of those entrepreneurs is Ben Francis. I met Ben in 2012. He was delivering pizza Pizza Hut in the UK in London and he's going to school and he didn't like that the apparel industry had not created something for just regular people going to the gym. Not talking with big dudes that really are, you know,

• 43:49Speaker 02

  benching 800 pounds. And he so he created a lot apparel brand called Gymshark. And Gymshark has now become one of the greatest brands on the planet in that industry. Gymshark has become an icon. They are sort of the the poster child for direct to consumer and for building a brand from scratch. And the best part is the thing that drives Ben today is the same thing that drove him then. And he did it with authenticity and he's done it with grit and he's done it with incredible sort of a commitment to not only being a better leader every year, but also making sure the company gets better. Even the way they do with influencers, I find incredibly sophisticated and smart. And so watching Ben's story all

• 44:31Speaker 02

  the way from, you know, literally dorm room to I just came out that Gymshark is now a billion, more than a billion dollar brand. That was in the that was in the media in November. So I can say that. That is like, there's a twinkle in my eye thinking about that story. I'm incredibly proud to watch to see that.

• 44:49Anthony Pompliano?

  So if I had to pick like one business that is super transparent, digital first, you know, kind of all the things that Shopify, I think, stands for, that probably would be near the top of the list. So it's pretty cool to hear you kind of talk about that one. And for those who haven't seen, I think it was in November when they made the announcement about their valuation, Ben put out like a pretty cool behind the scenes video really explaining, you know, all the way down to like, here's how much I own of the company. Here's why I made certain decisions, just the transparency. Is you know, off the charts. Yeah, it's really cool to see.

• 45:21Speaker 02

  But but something else, pump that I'd say to that is the amount of people don't really talk about this. And people talk about investment. Yes, I'm sure Ben may have invested in a bunch of different companies. But the amount of startups and brands that have been inspired by Ben's story that have now gone on to create their own stories. That flywheel effect of entrepreneurship. I mean, that's what I'm here for. That is is one of the most important things that is not really well documented or talked about. Because it's that that is the infinite game of all this, that more and more entrepreneurs are being created. And some of them are doing it for money. Some of them are doing it because they want to be famous. Some of them are doing it because they need to survive and put food on the table. Everyone on Shopify's definition of success is totally different.

• 46:00Speaker 02

  But the the the common thread is that they've all utilized entrepreneurship to find their version of success. And Ben exemplifies that.

• 46:09Anthony Pompliano?

  I love it. You've had the same business partners and people around you for a very long time. What's the importance of kind of long term partners in your opinion?

• 46:20Speaker 02

  Context, I think these companies like Shopify and many others, there are so many, there's so many parts to it. I mean, if you if Shopify was our capital business, for example, if it was, it's a standalone company. It would be one of the biggest capital businesses on the planet. Our point of sale company, if it was a standalone point of sale company, just for brick and mortar, it'd be one of the largest point of sale companies on the planet. So there's so many different moving parts to a business of our size. And we, you know, like Black Friday, I think we processed $2 billion worth of worth of GMV on one day. I mean, there was, I think, on a on a per minute basis, we were seeing about 1.1 or 1.2 million dollars a minute being processed on the platform. Having people that have very, very deep context is very, very valuable.

• 47:04Speaker 02

  However, the caveat to it is you need to also requalify for your job every year. And when you combine people that want to requalify and do requalify and also have very, very deep context. You end up with a very, very long tenure. And I used to sort of attribute that to the Canadian thing that we're in Canada and people are more loyal here. I actually don't think it's a Canadian thing. Maybe it is, but it's actually shop of, I think. The average tenure at Shopify is very, very long. And part of it is that we look at people's careers as jungle gyms and not ladders. And, and someone who's running a team may want to go be an individual contributor. And someone who's individual contributor may want to go ahead and run a fulfillment network. And, and we, as long as you re-qualify, um, I, we, we want, we want you to stick around.

• 47:48Speaker 02

  And that's been something that I'm really proud of about our company and our team.

• 47:53Anthony Pompliano?

  It's impressive. Three more questions. First up is the more serious one. What's the most important book that you've ever read?

• 47:59Speaker 02

  Ever read? Probably High Output Management by Andy Grove. I read it years ago, but I've read it probably again two years ago, but that would be, uh, that would be the most important book to run a company.

• 48:13Speaker 02

  And, um, what's another? Yeah, I would say that one is probably the way if you're going to give one book out, it'd be that one. Cause I think that is just so, um, it's prescient and it's so helpful to run a business at any stage. And probably the hard things of hard, about hard things is kind of the, the, the new, modern version of that. Because I think that Ben goes into detail about that stuff too. But I thought, um, High Output was just amazing.

• 48:37Anthony Pompliano?

  It's a classic for a reason.

• 48:39Speaker 02

  Exactly.

• 48:39Anthony Pompliano?

  It's classic. Second one is a little bit more personal. Uh, our friends over at Eight Sleep, um, they've got this thermoregulation bed that I've been sleeping on. And I've become fascinated with getting better sleep.

• 48:52Anthony Pompliano?

  What is your sleep routine? And how has that evolved over time? I'm sure when you were the only non-engineer employee, you were scrambling around, not sleeping that much. Has it gotten better or kind of, how do you think about sleep?

• 49:02Speaker 02

  I need to sleep seven or eight hours. I find that I'm a basket case when I don't. I, Lindsay and I, my wife and I have two young children. We have a two-year-old, uh, Zoe and a four-year-old Bailey, and, uh, they don't sleep that well. And so that is kind of tricky. So the last couple of weeks, they, the kids have been really tricky. And so, um, my wife and I have been taking turns waking up. And then if I know that I have not had a really good night's sleep, I try not to have back to back to back meetings during the morning. I try to sort of, you know, come into the day. But actually, you know, I have pretty high anxiety. And like I mentioned earlier, I've learned how to manage it. One thing that I've done, and it's become almost, you know, almost common practice in tech. And I think in sort of the entrepreneurship space, but meditation has been one of the greatest things I've ever done. And I'm religious about my calendar.

• 49:45Speaker 02

  I diarize everything in my calendar from a walk with my wife to a five or 10 minute meditation or mindfulness session. And I think sleep is incredibly important and I don't have any ritual. Then I need pitch black. One thing that I didn't have previously was we had blinds, but they never closed properly. And that all I didn't realize how much that affected me. And now I shut the blinds and it's pitch black. And that has been really helpful.

• 50:09Anthony Pompliano?

  Yeah, it's, it's crazy to hear. Once you learn that how important sleep is going backwards to not sleeping a lot.

• 50:15Speaker 02

  Crazy.

• 50:16Anthony Pompliano?

  Yeah, I was, I was the exact same way.

• 50:19Speaker 02

  Because you, because you, you think of like, you know, there's sort of this culture in the space that you and I are in where it's, you know, like work, work, work, work, work, and that's everything. And what I think you actually realize is if you want to do this over a longer period of time, again, like it's been a third of my life and I wanted the rest of my life. I need to find a way to do this in a sustainable way. That doesn't mean slowing down. That doesn't mean me getting lazy or lethargic. It just means, you know, I grabbed some, some, some tea before the session because I, it's, it's in the afternoon. It's almost 3:00 PM here Eastern time. I want to make sure that I bring my best to this, this discussion. And I know that if I drink coffee now, I won't sleep well at night. But if I have half a glass of matcha, it'll give me just this calm alertness that I'm looking for.

• 50:59Anthony Pompliano?

  I could not agree more. Last question you could ask me when to finish up is more fun aliens. Are you a believer or a non believer?

• 51:08Speaker 02

  What's, it's called the Fermi paradox, right? I think it's, that's what it's called. There's, it's gotta be something like, like where are they? I believe in the Fermi paradox. That to me is a paradox. I, I'm confused how we haven't find them. We haven't seen anybody. Where the hell is everybody is sort of the, so I, I think I subscribe to the Fermi paradox philosophy. And, and my question for you, because I'm going to flip this around is I, I'm certain that you've purchased off a ton of different DTC brands, whether they're Shopify or not. What is your favorite independent brand right now?

• 51:40Anthony Pompliano?

  Oof. I'm cheating because I know the founders and I know their story and like there's always this like emotional connection when you know somebody's stories. So like, you know, founders who are watching like, go tell your stories and you'll get more customers and they'll stay with you forever. But Adams shoots both Wacast and Sidra are two immigrants from Pakistan. And they just have this ridiculous story that like, you know, anyone born in the Western world can't imagine like they didn't know English. They didn't have access to the internet, you know, they met their parents were like, no, you can't hang out. And they come from these small villages in Pakistan and eventually not only kind of stay together, not only make it to the United States, but eventually start a company, get accepted into Y Combinator and you know, it's just like this crazy thing.

• 52:26Speaker 02

  And I always tell people. And they know who they are, right? I mean, I just read an article about them, I think a week ago where they put in an ad that says, we are, I think the ad is, we are not cheap. Something like that, right?

• 52:36Anthony Pompliano?

  Yes, yes, yes, yes.

• 52:37Speaker 02

  And like we are, we are, we are, we are not, we are not inexpensive or something like that. And I thought that was what a clever thing to say, because what you're basically saying is, look, this is not for everyone, but for the people that it is for, these will be great shoes. These will be shoes you will absolutely love. And yes, the sticker price is 150 bucks and yes, that's expensive for a pair of shoes. However, what you are buying is something that you are going to value. And I think that is so damn important. And I think they're a Shopify merchant as well. So it's cool to, cool for you to reference that.

• 53:05Anthony Pompliano?

  For sure. Well, listen, you're doing a fantastic job, kind of not only sharing, I think, I think the message of the business, but also just entrepreneurship in general. And, you know, it's a pretty interesting to have this conversation after we watched 2020 where I think a lot of people just got reminded, you know, that there's a lot of stuff outside your control, but I think the one thing that the United States, Canada, and many kind of capitalistic and democracy driven kind of areas in the world understand is like the people who want to kind of change their situation, they can do it through entrepreneurship. And that's kind of the beauty of, of living in this part of the world. So we'll just keep it up.

• 53:41Speaker 02

  Beautifully said. Thank you so much for having me, Pomp. I really appreciate it.

• 53:44Anthony Pompliano?

  For sure. Where can we send people to find you on the internet?

• 53:46Speaker 02

  Harley F on Twitter, at Harley on Instagram. Those are the best place to find me.

• 53:51Anthony Pompliano?

  Awesome. And well, so thank you so much for doing this. I'll do it again in the future.