20VC: Building Shopify From $5m To IPO, Why The Future Of Retail Is Not Online vs Offline & Why Law School Is Like Finishing School For Entrepreneurs with Harley Finkelstein, COO @ Shopify

Harley Finkelstein is the COO @ Shopify, the e-commerce platform that has allowed a generation of people to become entrepreneurs and business owners. Harley joined the business with revenues of $5m, today the company has targeted this year for over $600m with over 400,000 merchants on the platform. They have raised over $120m in VC funding from very good friends of the show including Aydin @ Felicis, Jeremy @ Bessemer and Amish @ Firstmark. In May 2015, Shopify went public with a valuation north of $1bn. In Today’s Episode You Will Learn: 1.) How did Harley make the move from laywer to COO @ Shopify? 2.) Question from Aydin @ Felicis: What have been some strategic inflection points that at the time did not seem like a big deal? How have Harley and Shopify produced and maintained such consistent revenue growth? What is the secret? 3.) Why does Harley believe that the future of retail is not online vs offline? How does Harley react to the suggestion that retail stores need to transition from transaction based, to experience based? 4.) How does Harley view the rise of personal brand in today's technological world? How has this allowed previously non-monetized channels to be monetized? What are some good examples of this? 5.) Why did Harley and Shopify choose to IPO in 2015? How was the roadshow? What was the key learnings for Harley both pre and post-IPO? What does Harley believe it means to be a trusted public company? Items Mentioned In Today’s Show: Harley’s Fave Book: High Output Management Harley’s Fave Blog: Wait But Why Harley's Fave Shopify Store: Boosted Boards As always you can follow Harry, The Twenty Minute VC and Harley on Twitter here! Likewise, you can follow Harry on Snapchat here for mojito madness and all things 20VC. Eight is a sleep innovation company. With their latest product, the Eight Smart Mattress, being a bed that literally tells you how well you slept last night, paired with an intelligent sensor cover that measures the quality of your sleep and delivers a daily sleep report. In order to bring you the best product, Eight used anonymized sleep data and feedback from over 10,000 people, to understand which materials and types of mattresses give customers the best sleep resulting in their unique blend of four responsive and high-density foam layers plus one layer of proprietary technology that helps people track and improve their sleep. You can check it out on Eightsleep.com – and if you use the code 20VC you will get a whopping 20% discount! FullContact provides the ability to organize your contacts, gain rich insights into them and therefore build deep relationships. With features like automatically identifying and merging duplicate contacts to the ability to snap a photo of a business card and FullContact will transcribe them for you, so no more lost and loose business cards at events. It is with these features just being the tip of the iceberg, FullContact really is the best all in one solution for contact management and you can check them out on fullcontact.com.

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

• 0:00Harry Stebbings?

  This is the 20 minute VC and Founders Friday with your host Harry Stebbings and please do add me on Snapchat at H Stebbings with two Bs if you have not already. It would be a pleasure to see you there. However, to the show today, and I have to say, I've been very excited about this one for a while. What many of you do not know, and I don't think even the guest today knows, is that I used our guest today's company to allow me to build my first business and pay for college. So without giving more hints away, I'm thrilled to welcome Harley Finkelstein to the show today. Now Harley is the COO at Shopify, the ecommerce platform that's allowed a generation of people to become entrepreneurs and business owners. Harley joined the business with revenues of $5 million. Today, the company has targeted this year for over $600 million with over 400,000 merchants on the platform.

• 0:41Harry Stebbings?

  They've raised over $120 million in VC funding from very good friends of the show, including Iden at Felicis, Jeremy at Bessemer and Amish at First Mark. In May 2015, due to their incredible success, Shopify went public with a valuation north of $1 billion. I do also want to say a special thank you to Iden at Felicis for the intro to Harley today, without which this episode would not have been possible. But before we dive into the show today, I really want to talk to you about a company that's really changed the way I sleep and operate. Eight is a sleep innovation company with their latest product, the Eight Smart Mattress, being a bed that literally tells you how well you slept last night, paired with an intelligent sensor cover that measures the quality of your sleep and delivers a daily sleep report.

• 1:21Harry Stebbings?

  In order to bring you the best product, Eight used anonymized sleep data and feedback from over 10,000 people to understand which materials and types of mattresses give customers the best sleep, resulting in their unique blend of four responsive and high-density foam layers, plus one layer of proprietary technology that helps people track and improve their sleep. This is perfect for people like me, people who want to be more productive during the day, who use or have used a fitness tracker and want to take care of their health and fitness and sleep. And if that is you, honestly, you have to check it out on eightsleep.com. And if you use the promo code 20VC, that's 2-0-VC, you'll get a whopping 20% discount. And with Eight keeping me productive with a home product, Full Contact is keeping 20VC team on top form.

• 2:04Harry Stebbings?

  With Full Contact, they provide the ability to organize your contacts, gain rich insights into them and their Or build deep relationships with features like automatically identifying and merging duplicate contacts to the ability to snap a photo of a business card and full contact will transcribe them for you. So no more lost and loose business cards at events like I always suffer from. It's with these features just being the tip of the iceberg that full contact really is the best all in one solution for contact management. And it truly has changed the way I not only manage my contacts, but engage with my contacts. And you can check them out on fullcontact.com. However, enough from me, so I'm now delighted to hand over to Harley Finkelstein, COO at Shopify.

• 2:48Speaker 01

  You have now arrived at your destination.

• 2:51Harry Stebbings?

  Harley, it's such a pleasure to have you on the show today. A huge thanks to Aiden at Felicis for the intro, but thank you so much for joining me, Stay Harley.

• 2:59Speaker 02

  Thanks for having me. I really appreciate it.

• 3:00Harry Stebbings?

  Now, I'd love to get started though, Stay, with a question from Aydin himself. And he asks, tell us about your transformation from a Shopify merchant to one of the most important key execs at Shopify.

• 3:12Speaker 02

  That's such an Aiden question. Aiden's a mutual friend of ours and he's wonderful. So my story sort of begins probably a couple of decades ago. I've been an entrepreneur for most of my life. I became an entrepreneur when I was 13 years old. I wanted to be a DJ in those days and no one would hire a 13 year old kid that had no DJ skills.

• 3:31Harry Stebbings?

  Outrageous.

• 3:32Speaker 02

  Totally outrageous. So I created my own DJ company and hired myself, which I thought was kind of the best way to become a DJ. And that obviously was a little bit of a gimmick. There wasn't really much to that business, but it just, it kind of opened my eyes to the fact that, hey, I can start things on my own. And so I think I always wanted to be an entrepreneur. When I was an undergrad at McGill University, when I was 17 years old, I started my second company. That was a little T-shirt business, making promotional products for different universities. So the T-shirt, the bag, the hat that you get on the first day of school. We made that for a bunch of different schools and around Canada. So that was sort of, I think that's when I decided, well, no matter what I do, a long term, my life's work will be very closely tied to entrepreneurship in some way. I moved to Ottawa, Canada in 2005 to attend law school.

• 4:15Speaker 02

  And the only reason I did that was I had a mentor of mine who was teaching law at the University of Ottawa. And he convinced me that a law degree might be very helpful for for an entrepreneur and some of them wants to, you know, build companies. And he was absolutely right.

• 4:28Harry Stebbings?

  I got the same advice too. I'm a law school student as well.

• 4:31Speaker 02

  It's interesting. In many ways, I think law school was a little bit like finishing school or etiquette school for entrepreneurs. It teaches you how to write really well, which of course is really important if you're running a company. It teaches you how to be articulate and teaches you how to read 4,000 pages, but select the one line that's most relevant. When I moved to Ottawa, the little t-shirt business that I had previously wasn't going to last. And the reason was it necessitated my in-person salesmanship. I had to go to these universities in person and sell them on buying t-shirts and promotional products from me. And in law school, they used to call the Socratic method, which effectively means that someone's going to call out a question and the professor's going to say, hey Harley, you need to answer this question. If you're not in class, there's a good chance he's going to fail you or she's going to fail you. So I needed a business that was a little bit more virtual and a little bit less brick

• 5:13Speaker 02

  and mortar or a little bit, it didn't necessitate my selling in person. And when I moved to Ottawa, I didn't really have any friends or family here, didn't know anyone here other than this one particular mentor of mine. But I did hear about a group of people that started hanging out at this local coffee shop every Friday night. And it was a group of entrepreneurs. They called themselves the Young Entrepreneurs Club, the Y E C. And I just showed up and started talking to these people and in many ways, kind of found my tribe. These were, these were sort of my people. They were, these were young, ambitious entrepreneurs and I learned a lot from them. And one of the entrepreneurs that I met through, through that, at that coffee shop was this brilliant engineer and programmer named Toby. And Toby, at the time, he had moved here to Ottawa a couple of years prior to that because he met a girl and he moved to Canada to sort of be with that girl who's now his wife and the mother of his three children.

• 5:55Speaker 02

  And he had moved here and needed to start something or wants to start something, I should say. And he wanted to sell snowboards on the internet. And at the time, in 2004, 2005, there really were two ways to sell a product online. One way was you would pay some agency, a million bucks to do some sort of IBM Web Store integration or some sort of Magento or, you know, some sort of hybrid integration. These, these big enterprise software packages that required a ton of work and a lot of upfront costs. And that wasn't possible. That was simply too expensive. The other way, obviously, that you were able to sell a product online in those days was to use a marketplace like eBay or Etsy or Amazon. Although that was inexpensive, that really didn't provide you with your own brand, your own site. You were sort of renting customers from these marketplaces.

• 6:36Harry Stebbings?

  Absolutely.

• 6:36Speaker 02

  And so Toby, being this really brilliant programmer, decided he would write his own piece of software to sell these snowboards and built a really nice snowboard business, online snowboard store called Snow Devil. And he'd realized fairly quickly that although the snowboards, selling snowboards was a good idea, perhaps the software behind the snowboard business may be a great idea. And he'd sort of stopped selling snowboards and really could focus on the software. And that's around the time where I met him and I ended up signing up for Shopify as one of their first customers. I think I was store number 137 or something like that. And I became an early merchant on Shopify's and spent the next couple of years finishing a law degree and MBA while selling T-shirts online. And after law school, I'm not sure how it worked where, I'm not sure how it worked in your school,

• 7:18Speaker 02

  but in order to get called to the bar in Canada, you have to do 10 months of articling, meaning you have to go work for a law firm for 10 months. And I moved to Toronto to work for a fairly large law firm and I just hated it. It was the most, it was the worst year of my life, to be quite honest. Unlike entrepreneurship, which I felt was all about, was really a meritocracy. I felt the law firm environment, the law firm culture was very much about legacy. It mattered how long you've been there, who you knew, who your parents were, what golf club you went to. And just, it was the antithesis of everything that I loved about entrepreneurship. And so in 2008, as I was realizing that I was never going to practice law and trying to figure out what my next move was, I gave Toby a call and said, look, I'm a massive fan of the product, I love Shopify.

• 7:58Speaker 02

  I feel like what we can do here is dramatic and I would love to come and help build out the business side of Shopify. And about a year later, I moved to, with my then girlfriend, who's now my wife, we moved to Ottawa. And I sort of became the first non-programmer to join Shopify and started basically playing the role of a Swiss Army knife. My job was to figure out what wasn't being looked after here and work on that stuff. And about eight years later, I feel pretty damn lucky and pretty fortunate that Toby invited me or allowed me to come and work with him here and we built a really wonderful company together. And it's been a dream come true.

• 8:29Harry Stebbings?

  Well, I'm going to dig into one word you said there and you said luck because you've gone from 5 million to north of 600 million, I think it is this year. But the interesting thing that I didn't point out. Was the element of consistent revenue growth, something that's not attributable to luck, Harley. But what are the key decisions or unique strategy behind the outstanding consistent revenue growth? Do you think when you look back at the journey?

• 8:54Speaker 02

  So to be clear, we are first and foremost a product company and we believe product comes first and having a great product revenue follows after that. We don't chase revenue. In fact, if you read Toby's letter to shareholders when we filed our IPO, we made it very clear that if you're looking for sort of quick wins, you're looking for a company that is going to chase revenue. We're probably not the right company to invest in. We've always been really product focused. I think the reason is we were Shopify was the product that we were selling, we're looking for. When I was trying to sell T-shirts and Toby was trying to sell snowboards. And I think we come to this with a lot of empathy for what entrepreneurs need and require and how they how they sort of think about things. I think part of the reason that you've seen, I think I didn't describe the term he uses consistent is we've been very deliberate in the things that we've done. And so we were deliberate in building software that we felt most people needed most can use most of the time.

• 9:39Speaker 02

  It was very easy to use, it was very easy to customize, but it was also very scalable. So whether you're starting a store on Shopify at your mom's kitchen table, or you're selling hundreds of millions of dollars of products, which we do have merchants that do that on our platform. You would never have to leave the platform that Shopify can provide you everything that you need. I think by being deliberate on the product side, we've been able to, the revenue has followed that. I think the other thing that has worked well for us is product market fit is one thing, but also timing is really important. And in the last couple of years, entrepreneurship, the concept of it has dramatically changed. It's no longer what you do when you don't get into law school or when you don't get the job at the big I bank or consulting firm. Entrepreneurship is actually has become, the connotation has just changed dramatically. And there's a term obviously now that is kind of pop culture called side hustle.

• 10:24Speaker 02

  But the idea of side hustle, I mean, it's certainly not a unique term, but it is something that's kind of new to the world. For a very long time, people were squarely focused on their nine to five and they even called it their nine to five. And I think what's happened more recently is people are self-actualizing by creating products and brands that are really unique to their individual personality and their individual taste and the things that they really care about. Maybe they work on nine to five, you know, to. To put food on their table and put a roof over their head. But what we would love them to do is to focus on the thing that makes them happiest. And for a lot of these people, what makes them happiest is really self-actualizing with their own business and being an entrepreneur. And I think we've created a product where the learning curve to start a business on Shopify continues to get more shallow and less steep

• 11:09Speaker 02

  and makes it easier and easier. And so I think we've just been consistent in our thinking around that.

• 11:14Harry Stebbings?

  I mean, one very interesting question that, again, I have to admit, Aidan did give me. And it was talking about kind of big decisions and strategic moves that at the time didn't seem like a big deal, but in hindsight were actually game changers. Are there any that come to mind with that respect?

• 11:29Speaker 02

  I mean, probably the biggest one, you know, if you were to walk outside in any major street, at least I hope so, in any major street in the world, and you were to say to ten random people, you'd ask them what Shopify does, nine out of the ten would say that Shopify enables e-commerce. And I think that's what we're best known for. But around 2013, 2014, it became increasingly clear to us that the future of retail is not binary. It's not online versus offline. Despite what you may hear from the CEOs of major malls and major retailers, the Best Fies and the, excuse me, the J C Penney's of the world, we didn't believe that these things were separate. And so we felt very passionately that the future retail is likely retail everywhere. That if you want to sell to a certain demographic, you have to have a great integration to Facebook or Instagram or Pinterest.

• 12:13Speaker 02

  And if you want to sell to a different demographic, you better have a great integration or you better have a great point-of-sale in-store experience. And another demographic may really want a great online experience, but maybe they also want a showroom. And the idea is that merchants and entrepreneurs, they need to sell wherever their customers or their potential customers are hanging out. And customers and potential customers are hanging out everywhere. And so we felt strongly that if the future retail is retail everywhere, then we needed to evolve our product offering to allow for that. And so around 2013 or so, you started seeing us put out new things like announcing our Shopify point-of-sale. Started seeing Shopify mobile, which allows you to accept payment in person at a farmer's market or a trade show. You started seeing us move beyond just e-commerce into a bunch of different channels.

• 12:56Speaker 02

  And our view is that that's sort of where the future of retail is going. I think now, I mean, the term omnichommer is, you know, you hear it in every keynote of every major retail conference. So omnichommer is sort of pretty top of mind these days. But go back three or four years ago and it wasn't as top of mind, it wasn't as popular. But we made a bet and our bet was that we think this is where the future retail is going. And I think makes us really unique. And so, you know, you can, if you don't use Shopify and you don't want to use our platform to sell in all these different places, you can bundle up a bunch of different single point solutions. You can do just e-commerce plus just going to sale plus, you know, maybe a card reader from like a company like Square. And you can bundle those all together, but what we think is you then create a bit of a Frankenstein

• 13:38Speaker 02

  and you become a bit of a human synchronization tool going back and forth where you're allocating inventory to some places and you're reporting lives in five different, you know, tabs in your inner browser. And we just don't think that's what entrepreneurs want. We don't think that's what is very efficient or productive for them. And we don't think that's what retail looks like. And so I think we've been somewhat courageous in some of these bets that some don't, not all of them have worked, but the ones that have worked have worked, we think really well.

• 14:03Harry Stebbings?

  You mentioned it potentially not being the end of brick and mortar like many suggest. A lot of VCs that I speak to suggest that we're going to see retail transition from a transactional location to a experience that consumers can enjoy. What's your thoughts on that and the need for retail to make the transition from transaction to experience?

• 14:22Speaker 02

  I think physical retail is probably going through its largest shift. And part of it is that there's a couple of big macro trends happening here. So one macro trend I think that's driving it is this idea of direct to consumer or disintermediation is another way to put it. So I ride a boosted board most days to work in the summertime, which is this amazing motorized skateboard from my home to the office. If I were to walk into a big department store or a big electronics store that sells a ton of different brands and I were to ask them, tell me about the boosted board. Tell me about this new boosted board two that just came out. What's the range of it? You know, what's the battery life of it? How fast does it go? I would probably get some sort of weird look from the salesperson

• 15:04Speaker 02

  because I'm not actually sure that that person knows more about the board than I do as a very typical consumer. When I go to boostedboards.com, which is online store on Shopify, a little chat box pops up in the bottom right corner and I can ask all these questions. I can get answers in real time from the people that are making the product, that care a lot about the product, that have a real understanding about the R and D behind this new Boosted Board 2 that has just come out. So from a consumer perspective, I and I think many others are now, a lot of us prefer to go direct to consumer because I get a better experience as a consumer. In many cases, I pay less because they're not kicking off a margin to the third-party retailer or to the retailer who's buying these products wholesale and retailing them. And I think from a maker perspective, manufacturer perspective,

• 15:49Speaker 02

  Boosted Board can now make more money because whatever I pay goes directly to them. And so there's so much value add in that stream and in that flow. I think that's really important. So where I think retailers provided value years ago was that they had distribution. The fact that Best Buy had stores all over the world in different cities, that was enough to justify their margin. And the fact that they didn't know much about the products didn't almost matter because there was nowhere else to buy a boosted board. But what's happened is the internet now provides distribution on its own, which means that all these manufacturers can go direct to consumer. And so the question, going back to your question was, so what exactly is the future of brick and mortar retail? And I know experience is something that is quite popular. I think the reason that it's popular is because that is another way of saying,

• 16:33Speaker 02

  brick and mortar retailers need to find another way to add value in the chain from the manufacturer to the consumer. And if they provide a great in-store experience, so for example, you know, if I want to buy a bespoke suit, that's still kind of difficult to do online sometimes. But I can go into a store and I can have my measurements taken. Even if I don't complete the purchase in that store, but I complete the purchase on their website, that physical retail is still adding value in the entire transaction of that bespoke suit that I purchased. And so I think that retailers, the brick and mortar retailers, I think there's still a real place for them. But I think they need to be a little bit more open-minded about, it's all retail and maybe all you're really doing is with your brick and mortar store, maybe it's just a retargeting campaign sort of thing, where I'm just reminded of the value of this brand

• 17:17Speaker 02

  or I'm reminded of why I want this particular. But I think the reason you're hearing so much about experience is because these physical retailers fundamentally need to understand that they have to add value and just being there, just having a store on its own is not enough because distribution is no longer, it's commoditized now and the internet did that.

• 17:34Harry Stebbings?

  You you mentioned the element of brand there. I'm intrigued. How do you believe we're seeing the world of consumer brand evolve with the technological advancements that we're seeing alongside it?

• 17:44Speaker 02

  I mean, brand is an interesting one because it means different things to different people, but I think the fact that.

• 17:48Harry Stebbings?

  What does it mean to you?

• 17:49Speaker 02

  Brand is what people think about when they hear the word, for me at least. So when people hear Shopify, what do they think about that to me is the brand. And my hope is that when people, most people hear Shopify, they think about entrepreneurship because that's really what we're all about. We want to spread entrepreneurship around the world. We want to, we want to make it easier to to start a business and we want to fundamentally take the path that leads to more entrepreneurs. We think that's really great for the world. I think that if I look at two Shopify stores, so I look at Drake's store, for example, or I look at Kanye's store, for example, what's fascinating is that if you go back 10 or 20 years, you had these celebrities that had massive followings. They obviously, the followings weren't on social media, but they had a fan base.

• 18:26Speaker 02

  And when they wanted to monetize that fan base, they would do it through record sales and they would do it through concerts. And if you went to one of those concerts and you want to buy a T-shirt with the band, a band's name on it, or had some sort of product that that incorporate the band's brand, they were kind of these crappy T-shirts that had the band logo on the front and all the different cities on the back.

• 18:45Harry Stebbings?

  Yeah.

• 18:46Speaker 02

  And that's kind of what these concert T-shirts look like. If you go to OVO, which is Drake's brand, Drake's store, the products that are coming out from these celebrities are so, so different. They're incredibly unique. They're really quite, quite incredible. Drake has created a brand of clothing that I think rivals any major clothing brands. I think Kanye has done a similar thing with Yeezys and with Yeezy Supply. And so I'm fascinated by that. I'm fascinated that not only are these artists and these influencers and whatever term you want to use there are able now to engage differently because of the internet with their fan base, but they're able to create a totally different brand around what they're doing beyond just their music. And it's not just a crappy T-shirt. If you, if you look at OVO or you look at Yeezy, this is really.

• 19:30Speaker 02

  High quality stuff that rivals the likes of the best fashion companies on the planet. So I think that is happening and I think because frankly, anyone now can have a brand online. It's really interesting to figure out, well, if I have a brand and I have an audience, what does my audience want? I can actually figure a way to deliver more value to the audience by creating products. In many cases, those products get sold on Shopify. So that's a long answer to a short question, but that's, I think that's fascinating.

• 19:54Harry Stebbings?

  No, it absolutely is, but you mentioned obviously the brand and the mission of entrepreneurship and delivering that to the world. And you've done this with outstanding success. You IPO'd in May 2015. I'd love to talk about this and the decision to IPO at that time, when there were potentially fewer tech IPOs than we've seen in the last couple of weeks for sure. So what was the process like for you and why did you decide to do it at that time?

• 20:16Speaker 02

  A couple of things. We have very big ambitions here at Shopify. We've always had very big ambitions. We felt that at the time, the company was ready. We felt the team was ready. We felt our product was ready. And there was no reason not to do it. We want to stay a large, independent business for a very long time. We want to build a hundred year company. And at some point, being a publicly traded business, it makes it easier to be a long-term company. And so it just made sense for us. We had raised three rounds of financing, our Series C, I believe, was around 2014, raised a hundred million dollar round. And we felt that the company and the team here was just, was just ready for it. And so we went and did it. And honestly, it's been a wonderful experience. Our goal then is, it's still today, is not just to be a public company, but really to be a trusted public company.

• 21:00Speaker 02

  And I think we've done a good job of getting, of moving towards that.

• 21:03Harry Stebbings?

  Can I ask, what do you, what do you think makes a trusted public company? Is it a lack of volatility? Is it a united team? Is it a fantastic culture that's embodied in the brand? What is it for you that embodies that trusted public company to the wider market?

• 21:18Speaker 02

  Yeah, I think it's simpler than that. I think it's you do what you say. And we've now, we just announced our last earnings for Q1 2017, past Tuesday. And so we've been public now for eight quarters and I think, I think really trust is built on consistency and doing what we say time and time again. We're going to make mistakes and I think all companies do that. We learn from those mistakes and, and there's going to be things that don't always work here, but I think we're. Candid, I think we're quite transparent and we do what we say. And so that I think is really the key. But you know, myself and Toby, we've never ran a publicly traded company before, even our CFO, who has a lot of experience as a CFO, he's never really ran a public company either. So we tried to really learn as much about the process as we possibly can. We had some great mentors and great advisors, people that had either gone public or who understood the capital markets and the IPO process.

• 22:03Speaker 02

  But it's been a really, it was a great experience. And I don't know, I have to say, the roadshow for me was one of the most interesting and exciting two weeks probably of my life. I got to fly around the world and meet incredible investors and great, really smart people. And I got to tell the story that is my favorite story, which is that of Shopify.

• 22:18Harry Stebbings?

  Can I ask, what was the biggest learning in either the roadshow leading up to the IPO or the IPO itself? You mentioned the great mentors and the incredible investors that you met. Are there any kind of really tangible learnings that you took from the process, either pre or post?

• 22:31Speaker 02

  There's a couple of things that stick with me about that process. I mean, one thing is I think we took for granted people's understanding of our business. And so we really had to spend a lot of time, in fact, you may have seen this, but we sort of created a mini documentary of Shopify with the IPO package.

• 22:46Harry Stebbings?

  I did, yeah, fantastic.

• 22:47Speaker 02

  You know, we thought it was a neat way to do that. Most companies sort of turn their camera on and some executive reads a script. We actually created a real documentary to tell the story of Shopify. And I think I took for granted that people understood what we did. And so, you know, there were still people around the IPO point who really weren't sure, are we a marketplace, how do we function? And I may have, you know, when you're so heads down like we are and we're focused and certainly, you know, located in Canada has a lot of benefits, but perhaps we're sort of outside the bubble of Silicon Valley where a lot of these companies are based. It was important that we told the story really well. So we tried to do that. We also just really just tried to learn as much about that process as we possibly can. And so we stranded ourselves with people that are far smarter than we are. And it was a great process. I enjoyed it.

• 23:31Harry Stebbings?

  I'd love to finish this day with a quick fire round. It's my favorite part of any interview. So I say a short statement and then you give me your immediate thoughts in 60 seconds or less. How does that sound?

• 23:41Speaker 02

  Sounds great.

• 23:41Harry Stebbings?

  So you mentioned being in Canada. How was it building such a huge business outside of a traditional tech hub?

• 23:48Speaker 02

  Wonderful. I think business today in particular- Particularly technology companies are geographically agnostic. I don't think it matters where you're based. I think what's most important is that you have access to great talent and we certainly have great talent here in Ottawa, but across Canada. And we get something that I think some of our peers in the valley may not get, which is incredible loyalty. People come to Shopify to do their life's work and they stay here for a very long time.

• 24:09Harry Stebbings?

  What's your favorite book and why?

• 24:11Speaker 02

  So I'm not, I'm not a huge fan. I'm just thinking about the listeners in your audience. I'm not a massive fan of all business books. I find a lot of them are repetitive, but probably the, the book that I, I, I found the most beneficial from a business perspective was High Open Management, which is Andy Grove's book.

• 24:25Harry Stebbings?

  Oh, it is fantastic.

• 24:26Speaker 02

  It's an old book, but it's, it's a classic and I, you know, I, uh, most of my team, if not all of them have read it. I just, I think it's quite fantastic. But I'm always trying to, I'm, I'm reading a book right now called The Talent Code by Daniel Coyle. I'm always trying to learn as much as I can. I find, uh, yeah, but, but High Open Management to me is sort of in a, a category of its own.

• 24:42Harry Stebbings?

  What's been the biggest challenge you've faced since joining Shopify?

• 24:46Speaker 02

  Figuring out what I'm good at and what I'm not good at. Like I said, when I first joined, I was a bit of a Swiss Army knife. I kind of did everything that, that Toby didn't want to do or wasn't interested in doing. And I, as, as time goes on, I, I had to sort of figure out, okay, well, these are the things I, I think I'm, I can be world class at and I can get there. But these things I'm really not good at and hire for that. I think there are some people that are born natural leaders. You sort of have these innate leadership abilities. I don't think anybody is born a natural manager or, or an innate manager. I think management is something that is really, really tough. It's, it's, it's something that I'm, I'm trying to get really good at, but it's, uh, those leadership management are very different things and I spent a lot of time working on management. So that's, um, that's been a challenge to me.

• 25:24Harry Stebbings?

  What's your favorite blog or newsletter? What, when they come in through the ether of online, are you absolutely entranced by?

• 25:31Speaker 02

  So, I mean, frankly, frankly, I, I think what's amazing about Medium is that I'm able to sort of peruse all different types of categories. So, and then maybe that's a bit of a cop out because it's not really a blog.

• 25:40Harry Stebbings?

  It's absolutely a cop out.

• 25:42Speaker 02

  Uh, but I, I would say, uh, I would say probably the one that's most interesting is Wait But Why. I just find that's just so compelling. I love the, the, the amount of time and attention that the writer puts into it. Uh, I think Wait But Why is just really killer.

• 25:53Harry Stebbings?

  Okay. Penultimate question, and don't kill me for this one, Harley. What's your favorite Shopify store and why?

• 25:58Speaker 02

  I think I may have hinted to that because I'm. I'm just so into boosted boards and I'm so into skateboard.

• 26:02Harry Stebbings?

  Oh, really?

• 26:03Speaker 02

  So that's probably one of them. I really, we have a 10 month old daughter now and so I've been, I really like Goldie Blocks, which is a store out of California.

• 26:10Harry Stebbings?

  They did the, they did the Super Bowl, didn't they? Advert.

• 26:13Speaker 02

  Exactly, yeah. They got, they had a commercial for, for Goldie Blocks. It's, it's this incredible toy that encourages girls to, to sort of think about, you know, engineering projects as opposed to just playing with dolls. And I just find Debbie's, what Debbie has created is just absolutely incredible. So I'd probably put that in, in the category as well. And then trying to think of the third one that I'm, I'm really excited about. I mean, one of, you know, one of the best parts of Shopify is that we have, we have about 400,000 stores on our platform. And so I'm often on, on random stores and I'm just checking out. I'm like, this chicken looks really familiar. And it's sort of, it's a Shopify store. So I, I get to, I, I love when that happens. I love when I have a great online, you know, experience, even a great in-store experience. And I look behind the counter and I see Shopify point of sale, or I see it's an online store powered by Shopify.

• 26:54Speaker 02

  That's, that's super exciting to me. But that's the best part is that I get to see all these incredible projects. And some of these projects grow really big and become, you know, a hundred million dollar a year businesses on our platform. And some stay quite small and, and they're kind of these lifestyle businesses. And so there's this great variety.

• 27:09Harry Stebbings?

  And then I want to finish today by hearing the next five years for you and the Shopify road ahead.

• 27:14Speaker 02

  I think that, I think for Shopify, we're just focused on what does the future of commerce look like? The channels that we've recently announced is a really exciting thing for us because again, we just want entrepreneurs to be able to find customers wherever those customers are hanging out. And if it was 10 years ago, we'd probably have a MySpace channel. And in a couple of years from now, we may have a channel that, that's completely, that we haven't even heard about yet. So we're just going to continue to think about the future of retail and future of commerce and build it for that. On a personal level, I'm, I'm trying to become the best manager that, that the people that, that work with me have ever had. And that's something that I'm, I'm working really hard on. But I'm, I've never been more excited about our business. And, and certainly, as I said at the beginning of our chat today, I feel very fortunate that I get to do my life's work at, at a fairly young age, which is quite unique.

• 27:56Harry Stebbings?

  Well, Harley, I've so enjoyed chatting to you today. I'm not sure if it's a mutual law school connection, but it's been so much fun. So thank you so much for joining me.

• 28:04Speaker 02

  Thanks, Harry. Appreciate having me on.

• 28:07Harry Stebbings?

  So fantastic to have Harley on the show there and incredible to hear his learnings from first hand experiencing the incredible trajectory of Shopify from $5 million to north of $600 million a year. And again, a big thank you to Iden at Felicis for making the introduction without which this episode would not have been possible. And if you'd like to see more from us, then you can follow Harley on Twitter at Harley F or you can follow me on Snapchat at H Stebbings with two Bs. It would be fantastic to see you on those respective platforms. But before we leave you today, I really want to talk to you about a company that's really changed the way I sleep and operate. Eight is a sleep innovation company with their latest product, the Eight Smart Mattress, being a bed that literally tells you how well you slept last night, paired with an intelligent sensor cover that measures the quality of your sleep and delivers a daily sleep report. In order

• 28:51Harry Stebbings?

  to bring you the best product, Eight used anonymized sleep data and feedback from over 10,000 people to understand which materials and types of mattresses give customers the best sleep, resulting in their unique blend of four responsive and high-density foam layers, plus one layer of proprietary technology that helps people track and improve their sleep. This is perfect for people like me, people who want to be more productive during the day, who use or have used a fitness tracker and want to take care of their health and fitness and sleep. And if that is you, honestly, you have to check it out on eightsleep.com. And if you use the promo code 20VC, that's two zero VC, you'll get a whopping 20% discount. And with Eight keeping me productive with a home product, Full Contact is keeping 20VC

• 29:33Harry Stebbings?

  team on top form. With Full Contact, they provide the ability to organize your contacts, gain rich insights into them, and therefore build deep relationships with features like automatically identifying and merging duplicate contacts, to the ability to snap a photo of a business card and Full Contact will transcribe them for you. So no more lost and loose business cards at events like I always suffer from. It's with these features just being the tip of the iceberg that Full Contact really is the best all-in-one solution for contact management. And it truly has changed the way I not only manage my contacts, but engage with my contacts. And you can check them out on fullcontact.com. As always, I so appreciate all your support and I cannot wait to bring you next Monday's episode with Keith Rabois at Coastal Ventures.