The Tim Ferriss Show - #486: Harley Finkelstein — Tactics and Strategies from Shopify, The Future of Retail, and More

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Starting point is 00:06:34 Hello, boys and girls, ladies and germs. This is Tim Ferriss. Welcome to another episode of The Tim Ferriss Show, where it is my job to deconstruct world-class performers of all different types to tease out the habits, routines, favorite books, and so on that you can use. Cereal, maybe. Who knows? Morning routines. My guest today is Harley Finkelstein on Twitter, at Harley F. Harley is an entrepreneur, lawyer, and the chief operating officer, that's COO, of Shopify. He founded his first company at age 17 while a student at McGill. Harley is an entrepreneur, lawyer, and the chief operating officer, that's COO, of Shopify. He founded his first company at age 17 while a student at McGill. Harley is an advisor to Felicis Ventures, and he is one of the dragons on CBC's Next Gen Den. In 2017, he received the Canadian Angel Investor of the Year Award and Canada's Top 40 Under 40 Award.

Starting point is 00:07:20 And in 2016, he was inducted into the Order of Ottawa. From 2014 to 2017, Harley was inducted into the Order of Ottawa. From 2014 to 2017, Harley was on the board of the C100, and from 2017 to 2020, he was on the board of directors of the Canadian broadcasting company CBC, in other words. Twitter, at Harley F. Instagram, at Harley. Harley, welcome to the show. Hey, Tim. Thanks for having me. It's a real honor to be on the show. I love interviewing my friends because it me. It's a real honor to be on the show. I love interviewing my friends because it gives me an excuse to do a deep dive and interrogate in a way that would just be totally abnormal and maybe sociopathic over a dinner table. And I thought we would start with describing or explaining what Shopify is for those who may not

Starting point is 00:08:03 know. Yeah. It's interesting. I mean, Shopify has obviously grown considerably over the last couple of years, certainly post IPO in 2015. People read about us more often, but I think most people know us as an e-commerce provider, an e-commerce platform, the place you go to build an online store. My version though of what Shopify is, is really a bit different than that. I think Shopify is the world's first retail operating system. And we can get into what that means at a deeper level. But fundamentally, I think what we do is we enable anyone that wants to sell a product to do so, whether that's online or offline or anywhere else. And I think from a vision perspective,

Starting point is 00:08:40 where I'd like us to get to is I want Shopify to be the entrepreneurship company. I don't think there's been a company that's ever been created that has been the entrepreneurship company. And I think we probably have the best shot at that. So that's a bit how I see Shopify. And if we wanted to peg some numbers to that, any kind of stats or numbers, what can you share that would give people maybe an infographic of the mind, sort of an ideal of the scale and scope of what we're talking about? Yeah. So we currently have over a million stores on Shopify. So a million businesses, a million brands host their commerce on Shopify. The majority of those brands would self-identify as small businesses. And some of them that were small grew into be

Starting point is 00:09:21 really, really big businesses, the Allbirds of the world or the Bombases of the world or the Gymsharks of the world or the Fashionovas. But for the most part, we have a million stores on the platform. And if you were to pretend for a second, we're not a retailer, but if you were to pretend just for a moment that Shopify was a retailer, we would be the second largest online retailer in America after Amazon. And the reason I mentioned that is because one of the things that has happened over the last couple of years as we've grown and have become, for a lot of people, the default commerce platform, we've been able to aggregate a ton of these stores to get economies of scale, which we then give to entrepreneurs and help level the playing field. And you and I have spent countless hours talking about what it means to level the playing field for entrepreneurs.

Starting point is 00:10:05 And in terms of the company, it depends on the day you look. We're a publicly traded company. Our market cap is above $100 billion, which still sounds unbelievable to say and something that's kind of amazing. We have about 6,000 employees across 17 offices all over the world. And in Q2 of this year, so this past quarter, we're talking 2020, our merchants sold about $30 billion worth of products on Shopify. So that's sort of some of the high-level stuff. What books have been most formative for you in your business journey with Shopify? And or what have you gifted the most to other people? What books? Yeah.

Starting point is 00:10:53 One of the books that was suggested to me early on in my Shopify journey was High Output Management, which is the Andy Grove book, who obviously built Intel and had done an amazing job. And one of the reasons that it was recommended to me was it seemed to cut through a lot of the BS of most business books. For better or for worse, I went to business school. And we can talk about education stuff. I actually found law school to be 10x more valuable and instrumental for my journey as an entrepreneur and running a big company. But I did go to business school. The business books that they naturally give out, I thought, was just full of platitudes and full of things that I just didn't find very wise. Whereas I found High Up in Management to be

Starting point is 00:11:33 by far one of the greatest books. And then actually, I think Ben Horowitz's book, Hard Things About Hard Things, is almost like the modern iteration of High Up in Management as well. And that's been another big part of things that have been valuable to me in my own career. That said, we are in the middle of a global pandemic. And one book that I recently reread that I know you know about is Taleb's book, Anti-Fragile. And the reason I found it incredibly valuable to reread it is it feels like we're in a time of great breakage, of great change. And it feels to me like what is emerging through this global pandemic are two types of people and two types of entrepreneurs and two types of individuals, which is those that are resistant, that are kind of waiting for things to go back to the status quo, that are looking forward and anticipating when

Starting point is 00:12:21 normalcy will return. But then there's this whole other cohort of people, a whole other cohort of businesses even, who are resilient, who are not waiting for the status quo to return, but rather are thinking about how they can use what is happening as this incredible catalyst to change everything and to pivot and to adapt. And the neat part about anti-fragile is it talks about, obviously, the two main systems being robustness and fragility. But then Taleb introduces the third system, of course, which is anti-fragile, where things actually get better, stronger as they break, like the immune system, for example. And I've just found that to be an amazing book for the current time we're living

Starting point is 00:13:02 in right now, that you can take two people in the same circumstances and one just resist and the other simply is resilient about it. And that book just encompasses that. In terms of the book that I'm reading right now, I'm actually reading, this is shocking, but I'm reading my first fiction book ever. I've never read a fiction book in my whole life. I just wasn't into it. And I know it sounds so crazy, but I just, you know, it's not where I get, I usually read in order to get smarter or to understand a particular thing better, whether it's biographies or it's, you know, a business book or just generally a fascinating book

Starting point is 00:13:35 about an interesting true story. And I'm actually reading The Alchemist right now. And I know in this book, you know well. And it's amazing because the relationship that I have with reading The Alchemist relative to reading a book where I'm highlighting, I'm trying to digest, I'm trying to reflect on it, is just completely different. And it's actually a lot more enjoyable.

Starting point is 00:13:54 Actually, one of the books that I've given out the most, it's probably not the book, but in the early days of Shopify, I probably gave out 100 copies of The 4-Hour Workweek. And I'm not saying that to flatter you and I are already friends. I don't need to flatter you. But what I would say, though, is the reason that book was so important was because in 2010, the idea of a side hustle or the idea of a hobby project that eventually gets commercialized was just not in the ether. It was just not in the atmosphere. And this idea that you can actually build systems to allow you to run a business concurrently with doing anything else you're doing, whether you're in school or you have another job, that was somewhat foreign. And yet,

Starting point is 00:14:36 I knew that if we encourage more people to experiment with side hustles, it would lead to entrepreneurship and hopefully would eventually lead to them using Shopify. So certainly that was an important book in my life, but also in Shopify's life. many trends that may have been projected for 2030 have been pushed to the front of the line very, very quickly. So things have been compressed. So I want to ask you about the future of retail. But before we do, I want to talk about the past of Shopify. And I thought maybe a useful way to frame that or just a fun way to frame that would be, number one, can you repeat the number of employees and market cap of the company right now, depending on the day, obviously, but give or take? About 6,000. I think we're over 6,000 employees and market cap is, I don't know, a hundred and something billion, depending on the day. I think it's around 120, 130 billion.

Starting point is 00:15:40 Okay. And when we first met, how many employees were there and what was the market cap? We first met in sort of mid-2010. We had probably, I would say, around a dozen people at the company total. And I think we had just either had just raised or about to raise our Series A. Just about to raise. I think we were just about to raise our Series A. And I think our Series A was, I mean, it was sub 50 million. I don't remember the exact number, but it was definitely sub 50 million. So yeah, I guess a lot has changed from our original encounter, Tim, to now. Wow. Yeah. I think when you put it in that perspective with that type of

Starting point is 00:16:20 delta, it does seem quite incredible. And so I think this is a good time to just say, and of course, I've said this before, and you and I have shared a lot of tacos and not a small quantity of tequila on occasion. But I just want to say publicly that it has been such a joy to see you and your family and obviously your close friends like Toby and so on, the entire team. But since I know you personally, just to see you do so well has been so fun and such a joy for me. And just like you're not blowing smoke up my ass, you know this isn't me blowing smoke up yours, although I do wonder where that expression comes from, but not losing my train of thought, it couldn't have happened to just a nicer group of people.

Starting point is 00:17:13 I really feel that way. And I just want to congratulate you. It's been awesome to watch in the very literal sense of awesome. So well done. I appreciate you saying that. It's been the journey of a lifetime and there is not a second that goes by

Starting point is 00:17:30 that I take any of it for granted. I think that part of the story is that we've built something special and meaningful and valuable to the world, but also we've done it, you know, Toby likes to say that we are on a journey doing difficult things with friends.

Starting point is 00:17:42 And I think there's nothing better in the world of doing things that are difficult and challenging with people that you deeply like and you deeply respect. And the cool part about it is a lot of the friends we had in the early days, like you, for example, you're still part of the story today. I mean, you and I talked earlier today, unrelated to this podcast, but something totally different related to your business and our business and finding a connection point and helping each other. That type of community, people talk a lot about their group of friends or their group of their community, the people they spend the most amount of time with. But there's also sort of a peer group at a company level. I think that tends to get lost because most companies,

Starting point is 00:18:17 as they grow, and especially historically, if you study founders going back 100 years, at some point, there is this natural graduation where someone decides it's time to bring in the quote-unquote adult supervision or something like that. And you sort of lose the connection with the founding story. But because for the most part, those of us that are still at Shopify today are still the same group that were there in the early days, we've brought each other along with us and we've brought our friends along with us also. And it's made for a much richer experience. It's made for a much more meaningful journey when you do it with people and you grow together. Now, obviously, the flip side of that is in order to

Starting point is 00:18:54 do that, every single person, particularly on the leadership team, has to requalify for their job every single year. And that is difficult in year one and year two. It becomes incredibly difficult in year 10, year 11, and year 15, where the stakes, the challenges, the opportunities are all so much bigger. But I think for the most part, we've all focused on requalifying for our job and also keeping our, I don't want to say modesty, but just staying grounded in this whole thing and realizing that we're the same folks who were there at the beginning. And I don't know, in that way, it's just been a really awesome experience for us. Well, you guys are still nice Canadian boys.

Starting point is 00:19:38 Maybe it's a Canadian thing. Maybe the only reason we're nice is because we're Canadian. And frankly, I can tell you that there are some challenges that come with the Canadian thing as well. There's a lot of great advantages. There's something called the tall poppy syndrome here in Canada, which is you don't want to grow too tall because someone's going to chop you down. And you do feel that from time to time.

Starting point is 00:19:57 But for the most part, building a tech company outside of Silicon Valley, I think, has been incredibly valuable to us. I'm going to bookmark a bunch of things here. So I'm going to bookmark outside of Silicon Valley, I think has been incredibly valuable to us. I'm going to bookmark a bunch of things here. So I'm going to bookmark outside of Silicon Valley because most people do not think Ottawa when they think one of the largest tech companies in the world, for instance. And then I'm going to bookmark tall poppy syndrome. We'll probably not come back to that. So it's more of a note for myself, but I didn't realize it was an issue in Canada as well. It's an issue throughout the entire Commonwealth, right? This is an issue

Starting point is 00:20:28 and an expression that you hear in New Zealand, a little bit less so in Australia, but certainly tall poppy syndrome you hear about quite a lot in places like New Zealand. Let's also bookmark re-qualifying for the job. We're going to come back to what that means. And I'm going to go further back to law school. You said something about law school. Now, I'm going to get the pronunciation incorrect, possibly. Philip Reimer, is that his name? Wow, you've done your research. Jesus. I have. I've got a full dossier. I've got a full dossier. So who is Philip Reimer and why is he relevant? Yeah. So I was born in Montreal in Canada, lived here until I was 13. When I was 13,

Starting point is 00:21:12 there was a referendum in Canada, in Quebec, where I lived, where Quebec as a province wanted to separate from Canada. And the referendum never resulted in a separation of Quebec from the rest of Canada, but it created a really tense environment, particularly for Anglophones living in Quebec. And so when I was 13, my family decided to move down to South Florida. And so I went to high school in South Florida. And then after high school, I- Can I pause you for a second? Sure. Absolutely.

Starting point is 00:21:41 I actually didn't know this piece of the puzzle. How on earth do you choose South Florida? If you've ever been to Montreal, it's the most amazing city in the world. It's sort of, you know, it's like, it feels European almost, but it's in Canada, which is a wonderful country, but it's cold as hell. And February's in Montreal are notoriously bad because it gets dark very, very early. The number of sunlight hours is very small. And it's not just February. I mean, it's basically January till the end of March. And I think my parents, as they were deciding where they possibly could move to, I think it was going to be somewhere warm. And so it was a combination of staying on the East Coast, EST time zone, and the fact that we had some friends and family that had been living there

Starting point is 00:22:18 already. And so they just decided, let's go somewhere hot. And so we moved down in, this is probably 1996, moved down to South Florida. And then after high school, it was time for me to consider where to go to college. And my parents didn't have very much money. And so if I were to go to a US school, it would have required me to take out some sort of student debt. But because I was born in Montreal, McGill University, which is a great school, had offered basically me in-state tuition. And it was like $1,800 a year. And there was just... I loved Montreal. McGill was a great school and it was $1,800 a year. And so my parents were like, you got to go to McGill. I get to McGill in September 2001. And 11 days later,

Starting point is 00:22:58 September 11th happens, stock market crashes, things get really, really bad. And my parents lose everything. I mean, we lost our house, We lost everything. We didn't have a penny to our name. Why is that? That's because of the equity markets? Yeah. My dad was just over leveraged for the most part. And he was doing things he probably shouldn't have been doing. And he just did stuff that was just highly correlated to the equity markets doing well. And when the equity markets fell apart, things fell apart for us. And my mom called me and said, hey, you got to move back down to Florida because there's no way you can stay in Montreal. We can't give you money. We just come back down here and we'll figure it all out. And I was 17 years old when I started McGill. I was a bit

Starting point is 00:23:40 younger than my peers. I loved Montreal. I loved being on my own. And so I basically told my parents, hey, I'm going to stay here. I'm going to figure this out on my own. And I'm actually going to also try, if I can, to help the family out as well. I have too much younger sisters. So I thought, okay, I'll figure this out on my own. And I tried my hand at a bunch of stuff. I worked at a travel agency. I've been a DJ since I was a kid. So I DJed parties and events and weddings and anything that- And bar mitzvahs. Lots and lots of bar mitz weddings and anything that- And bar mitzvahs. Lots and lots of bar mitzvahs, like 300 bar mitzvahs, as you know. We've talked about that a lot. And so I DJed, I was working in a travel agency trying to go to McGill,

Starting point is 00:24:12 and it just wasn't working. There was no way for me to make enough money that I can still have a full-time class load and curriculum and also help my mom and dad and sisters, and also pay my bills and stuff. And a friend of mine just was on student council at McGill and said, hey, just so you know, if you're looking to start a business, one business that is kind of interesting is that McGill University spends like $25,000 every semester on promotional t-shirts. The stuff that you see in the bookstore, the stuff you get in your orientation bag that says faculty of science or faculty of arts or whatever it is. Hey, if you want to start something, that may be an interesting thing to start. And Montreal has historically had this

Starting point is 00:24:56 incredible, they call it the schmata business, but it's basically the apparel industry. You have companies like Buffalo and American Apparel and Parasuco and countless other companies have all been created from Montreal. There's a very well-known and well-developed clothing business and clothing industry. And I thought, okay, cool. Well, let me just- What was the colloquial name for it? Schmatte Business, which is- Is that Yiddish? Yeah, it's Yiddish. Yeah, it's a Yiddish term that basically means clothing.

Starting point is 00:25:22 And part of it was Montreal was an absolute immigrant town. My family came to Montreal from Hungary in 56, but it's an immigrant city. And so the neat part about the peril industry, the schmata business was that it had a low barrier to entry. So you can start a business with little capital. And I had little capital, but I had this one piece of insight, which is McGill University, where I go to school, needs t-shirts every semester. And my feeling was, if I presented them with a compelling proposal, good prices, and I was sort of took off, but four years in total, selling t-shirts all through undergrad to almost every university across Canada. So it worked. Well, it worked to some extent. It worked that it allowed me to pay my tuition. It allowed me to

Starting point is 00:26:16 help my mom and my dad and my siblings. It helped sustain me so I can finish undergrad and not have to move to part-time classes. What it didn't do though, and this is where Phil Reimer enters the picture, one thing that has been really valuable to me growing up was I was always able to have this group of mentors in my life. And I know you talk a lot about mentors and we've talked a lot of mentorship, but I've always had these groups of people in my life who I just really admire for totally different reasons. And I've taken this pretty far. Lindsay and I got married in 2013. Basically, six months prior to getting married, there were three people that just seemed to have the greatest relationship to their spouse.

Starting point is 00:26:54 And I called them and said, hey, tell me about being a great spouse. And I did the same thing for being a dad. I did the same thing in a bunch of different aspects of my life. But when I was starting out in entrepreneurship at McGill, one of the people that I contacted was this guy, Phil Reimer, who was just a friend of my parents who, it turns out, wasn't even that close to my parents. But he always seemed to, every time I met him or encountered him, we always had these really interesting conversations about business. And he would teach me things like the difference between the debt side and the equity side of a balance sheet. And he would teach me the idea of investment and taught me about equity markets and stocks.

Starting point is 00:27:32 And he would explain it in just this very simplistic, digestible way. And I just, like I did throughout my undergrad years, I called Phil towards the end of my undergrad and said, okay, I have this little business. It does well. I think I'm just going to continue building this business. And his insight was, in the same way that you were able to disrupt a bunch of existing incumbents selling universities t-shirts across Canada, anyone can disrupt you. You do not have what Buffett would call a moat around the business. There is no competitive advantage here. And so eventually, this business will not become anything. It won't become that big. And it's going to be a grind for you time and time again, because there is nothing that you have that is proprietary. And there is

Starting point is 00:28:15 nothing that you have that is special other than the fact that the people buying t-shirts from you are students and you're a student. So you kind of have that connection with them, but that was it. And his proposal or his idea was, have you thought about going to law school? And I was like, no, I don't want to be a lawyer. Why in heck would I go to law school? Anyways, what he did was he said, look, next year I'm teaching law at the University of Ottawa. And he's doing it part-time. He's sort of a big partner to big law firm here in Canada. And he said, I think law school would be like finishing school for you. It would be like etiquette school for you to be a better entrepreneur. The Downton Abbey of entrepreneurship.

Starting point is 00:28:55 Kind of, yeah. It would teach you how to write, how to think critically, how to debate, how to argue. It would teach you how to read 4,000 pages and pick out the one line. They call it the ratio decedenti, the one line that matters in a court case. You'd be able to pick that out out of 4,000 pages. And he convinced me that that actually would be an incredible advantage in my career to become an entrepreneur. And so I applied to one law school on the advice of this guy, Phil Reimer, and I got in the University of Ottawa and I moved here in 2005. Now you, I suppose, hinted at what you gained from your law education. What would you say, you mentioned a few things that he speculated you would learn. Were the most valuable things you learned those? Were they other capabilities or skill sets? What

Starting point is 00:29:44 were the main things you took away from that? And I should say also as a side note that many, many successful entrepreneurs have law degrees, but didn't practice law. Peter Thiel, Chris Saka, both billionaires who have been on the podcast among them. That is one common thread that shows up now and again. But what were the most valuable things in retrospect that you gained from that experience? Are you familiar with the Socratic method? Have you heard, do you know that term? I do have some familiarity with the Socratic method, but if you could explain it, if that's going to be part of the answer. You've studied Socrates and some of his work, so I assume there's origins there. But

Starting point is 00:30:19 law school uses the Socratic method, which at least the iteration of it in the law school that I went to was, the professor at the front of the class would ask a question and would randomly call out somebody's name. If you answered it correctly, you did well. And if you didn't answer correctly or you weren't present, you would do poorly. Attendance mattered, which was very different than my undergrad. And one of the things that, this is such a strange takeaway from law school, but the Socratic method made me really, really good at thinking on my toes. It forced me to, you couldn't read every single piece of assigned work because by the nature of law school, a lot of the intention is to overwhelm you with content and readings and work so that, one, you can get ready for the practice of law in the corporate world, I suppose, but also they wanted you to be able to start making good decisions about how to acquire information in the most effective way. The Socratic method for me was incredibly valuable because it meant that if I was given three cases to read, and one of the cases was 1,200 pages, and I can't read that in

Starting point is 00:31:23 24 hours, I would have to understand how to get the information, how one of the cases was 1,200 pages, and I can't read that in 24 hours, I would have to understand how to get the information, how to acquire the information in such a way that I could regurgitate it or I can repeat it if I was called on, but not know enough about it that if I didn't get called on, it would prevent me from doing well in another class who also used the Socratic method. And that ability to quickly stay on my toes and be ready at any moment to answer a question in a way that provides the professor with the information or to substantiate that I know what I'm talking about, but didn't necessarily require me to spend all of my time perpetually studying, that actually was one of the most valuable things. So I would say

Starting point is 00:32:01 that. And the second thing is writing. In Montreal, I went to a Jewish private school. And in the States, I went to a very large public high school. And it was a really good public high school. But I got to school. I went to McGill for undergrad. And I had never really learned how to write really well. And I only realized that in law school. I only realized in law school that I was able to write a lot, but it took me a long time just to get to the point. And that actually was another major piece of... It was shaped as a pedagogical learning, but it wasn't actually pedagogical. It was super practical that it taught me how to very quickly reply and quickly think on my feet or on my toes. But it also taught me how to write

Starting point is 00:32:38 really, really well. And for those things alone, I wouldn't change it for anything in the world, which is very, very different than, I don't want to slam MBAs, but I did a joint law MBA, so I also went to business school. Whereas the MBA was entirely case study based. Most of the case studies I felt were not even steeped in any type of reality. I did not find that to be at all valuable relative to my law degree to run a company like Shopify today. Just a quick thanks to one of our sponsors, and we'll be right back to the show. relative to my law degree to run a company like Shopify today. for the new year, LinkedIn Jobs will be there ready to help. And getting started is easier than ever with new features to help you find qualified candidates from their active community of professionals with more than 722 million members worldwide. Post a job with targeted

Starting point is 00:33:34 screening questions that will quickly get your role in front of more qualified candidates. Manage job posts and contact candidates from a single view on the familiar linkedin.com website where functions are streamlined onto one simple screen. And now you can do all of this from your mobile device, no matter where you are. That's how LinkedIn jobs can help you hire the right person faster. Visit linkedin.com slash Tim to get $50 off of your first job post. That's linkedin.com slash Tim to get $50 off of your first job post. Terms and conditions apply. I want to follow up on the Socratic method or acquiring the information that you need without digesting the 1200-word tome. And there are different aspects to the Socratic method. So I'm actually in luck with this conversation because about a week and a half ago, I read Socrates in 90 Minutes,

Starting point is 00:34:26 which is part of a series of books. They're very fun, very opinionated. So you have Wittgenstein in 90 Minutes, Plato in 90 Minutes, and I think there are somewhere between 10 and 20 of these volumes. And they're very quick to digest as the titles would imply. But I'm going to read just briefly for folks a description of dialectic from Wikipedia. And here's what it says. The Socratic dialogues are a particular form of dialectic known as the method of, and here you can probably correct my pronunciation, but elencus, E-L-E-N-C-H-U-S. I don't know if that is from Latin or elsewhere. Literally, refutations or scrutiny whereby a series of questions clarifies a more precise statement of a vague belief, logical consequences of that

Starting point is 00:35:10 statement are explored and a contradiction is discovered. So this is, I think, a different aspect than what you're talking about. So I'd love to hear you perhaps give an example of how you would tackle fixing that impossibility of reading the 1200 pages, what approach you might take. But I want to point out for people listening also, if they haven't done any type of debate, which by the way, is something that if you ever see Peter Thiel on stage, he will realize he has a lot of training in even if he is not able to review a lot of materials beforehand. And part of how you can be effective in debate is by asking people to very clearly define the words that they're using, very clearly give examples or definitions of their positions. So you can effectively, in the realm of debate, lead someone to defeat themselves before you ever take a counter position, if that makes any sense.

Starting point is 00:36:10 Totally does. And actually, it's the best way to defeat them because then actually, it's basically, it's unforced errors. Exactly. As opposed to forcing them to make an error or to make some sort of mistake. The way that it worked, at least in my law school, but I think this is the case in most law schools, is the teacher would ask a question randomly to a student and say, you know, Mr. Finkelstein, tell us about this particular case. And then what he or she would do is they would ask question after question, which helped them substantiate whether or not I understood the case itself. So for example, hey, what's this case about? I would say, well, this is a tort case, for example, and someone fell on someone else's property. Okay, well, why is this controversial? Well, the reason is the property that they fell on wasn't actually the homeowner's property,

Starting point is 00:36:55 it was city property. Well, okay. And I always tried to kind of work backwards from what is the actual thing that the teacher wants to teach right now. It's not necessarily about the property. It's not about the fall. It's not even about the tort itself. It's about some other thing that the professor believes will be valuable for these students to go off with after this. And usually, it's something that is far more universal and far-reaching than just, well, this is how the case ended. And so what I tried to do constantly was, okay, this case, X versus Y here, fundamentally, the professor wants to get to the point where we can have a discussion about city land. And so how do I go from the overview of the case to a discussion

Starting point is 00:37:37 with city land? And through that questioning and through that critical reasoning and critical debate, I was sort of able to draw some sort of almost like literally a map between that initial question to the final question. If I was able to get that, none of the other details really mattered. The problem was not all teachers were consistent in that way. And some professors didn't actually think critically about what the lesson was. Not all professors are at the same level. Some are bad professors, frankly, at every school. Not everyone's going to be the greatest professor of law at every single school. And so I'd figured out that this is where the professor wants to get to. Let me simply reverse engineer the line of question to get there. And if I knew that, I satisfied myself that that was a sufficient amount of studying to not get called out or

Starting point is 00:38:25 not to get a bad grade. So let's say that you are designing a curriculum or giving assignments, could be reading books, could be resources, could be any type of homework assignments for someone who wants to acquire some of the most valuable skill sets you were able to develop through law school without going to law school. Yeah. There's a book called The Elements of Style. I think that's what the book is called here. Yes. Yeah. Strunk and White. Exactly. That's right. Strunk and White. Yeah. I mean, frankly, everything I learned in law school from a writing perspective, The Elements of Style would have taught me already. And I think it was written like the 1920s. Yeah. 1923. Very small, very short book. I think it was written in the 1920s. Yeah, 1923.

Starting point is 00:39:06 Very small, very short book. I think it's like 60 pages or something. 43 pages. 43 pages. I mean, it's incredible. Published in 1918. Wow. Yeah. So if I didn't go to law school, but I want to replicate some of those learnings, some of those lessons, The Elements of Style was a big one. That would be first. The second thing that actually it did was we had a lot of guest lecturers in law school.

Starting point is 00:39:28 And I went to law school in 2005. YouTube was probably around. It wasn't necessarily as popular as it was now. But one of the things that the professors did, and I think a lot of law schools do have this type of dynamic where they bring in guest lecturers. When you bring in someone, this is why I love podcasts so much or interviews for that matter so much, is because when you bring in someone who's written a book and you give him or her an hour of their time and you ask questions about the book, you tend to very quickly get to the part of the book that they loved writing the most. And that tends to be, not always, but that tends to be the major takeaway.

Starting point is 00:40:05 And so if there's 12 chapters, usually the writer, the author, in this case, legal textbooks, the legal scholar on the topic will very quickly get to, okay, forget all that. Here's what I want to talk about today. And that I think you can replicate without going to law school simply by watching great podcasts and great interviews and just really high-quality conversation. And probably the third thing is, which you sort of said this earlier, but we did moot court, M-O-O-T, which is effectively like debate. You're pretending like you're in court. There's a judge. There's a jury. There's two sides of a particular argument. And whether it's debate or it's moot court, that has been instrumental in my life.

Starting point is 00:40:47 And I love moot court. I did quite well. I was able to compete with other schools and people in different countries. So whether it's debate or it's moot court or it's any way that you actually can get into difficult discussion where the other party is not only looking to be right, he or she is looking to prove that you are wrong, man, I think that is incredibly instrumental. Yeah, for sure. To build on a few things you said, so along with The Elements of Style, there's a great book called On Writing Well by William Zinsser, Z-I-N-S-S-E-R. It's a classic. It's a bit longer, 300 and some odd pages, but I found it incredibly helpful for removing ambiguity and what one might call in the legal profession puffery.

Starting point is 00:41:32 Maybe not in Canada, but in the US. Yeah, no, no, totally. That's here too. So puffery, I'll give an example. If you have ever bought a shampoo that says increase vitality or hair volumizer. These are words that have no meaning. They can't have a meaning because that would then be a structure or function claim, and it would require all sorts of other regulatory hurdles for an over-the-counter product like that. Or toning in the realm of exercise. That does not have any physiological meaning whatsoever.

Starting point is 00:42:05 And to help clean up, declutter your mind of these types of words or any type of bloat, these types of books are super helpful. Furthermore, one thing you can do, and I've done this before with my own writing, is to ask friends or to hire someone like a star law student, they don't have to be a lawyer, to edit your writing. And they could be arbitrary writing assignments. It doesn't matter, right? Make it an assignment for yourself if you have the budget or the access or the ability. Three pages a week. You have a three-page assignment every week, and you have someone with legal training go through it to redline the shit out of it because they will identify anything that were in a contract, let's just say, would immediately get spotted by one side or the other because it's unclear. And if you need something to be defensible or to withstand scrutiny of the court, you got to ferret that

Starting point is 00:43:05 shit out right away. And it's super, super helpful. It's funny. I'm just reading. So Stephen King wrote a review of Elements of Style. And this is a funny review that he wrote. He said, there's little or no detectable bullshit in that book. Of course, it's short. It's 85 pages, much shorter than this one. I'll tell you right now that every aspiring writer should read Elements of Style. Rule 17 in the chapter titled Principle of Composition is omit needless words. And I will try to do that here. That's this entire review of the book. Yeah, I have another one next to me just for nerds who want to really go crazy. Literally a book that I have with me today called Draft No. 4 by John McPhee, M-C-P-H-E-E, on the writing process, which if you really are a nerd and want to study structuring, how you structure a piece,

Starting point is 00:43:54 that's a really excellent book as well. Before we move on from books, real quick, you mentioned the alchemist Paulo Coelho. So two things on that. Number one, for people who don't realize, yes, that book has sold something like 100 million plus copies in many languages. It was a complete failure in the beginning. It was rejected. It was pulled from circulation. And Paulo has been on the podcast. I want to make one fiction recommendation to you. And that is Dune by Frank Herbert. And I think it will go right up there next to the Horowitz book and next to Andy Grove in terms of maybe not management, but leadership books. I think you'll be very impressed with it. Let's come back to your job. What do you do at Shopify, Harley? My official title is Chief Operating Officer.

Starting point is 00:44:51 And from a sort of divide the world and conquer perspective, I look after more of the business side of Shopify, the commercial side of the business. But actually, we talked a bit earlier about this idea of requalifying for your job. Part of that annual requalification that I'm trying to do each and every year is to also understand how to add the most amount of value. And one of the things that I think is really important in the early days of any company, and actually, it's super important as a company ages, but certainly in the early days where you don't have 6,000 people, is to figure out, okay, what are the ways I can add value? Things that only I can do, things that have the

Starting point is 00:45:29 greatest impact, things that I enjoy doing. And the one common thread or common theme in my... I've been at Shopify for more than a decade and I'm 35. So almost a third of my life I've spent at Shopify, which is kind of crazy, but those are the numbers, has been, how do I get more people to understand what we are doing? How do I properly storytell why Shopify is so damn special? And obviously, it's much easier for me to do that today than it was for me to do in the early days. Although we should talk about build a business because probably the first real storytelling opportunity that we did as a company was build a business. And you were sort of the co-founder of Build a Business. We can get to that later. But I would say today, my job is, besides the storytelling thing, it's bringing on some of the brightest, sharpest humans on the planet to Shopify, and then making sure they

Starting point is 00:46:19 absolutely have no roadblocks or constraints in their way so that they can do their life's work with us together. That sounds a little bit mother goosey, but that's truly how I spend my time. That's a great adjective. I am going to use Mother Goosey in the future. So storytelling. Storytelling is important. Persuading is important. That's another skill you were able to practice in law school. And that applies in the Build a Business competition, which we'll get to. Also applies in fundraising. Also applies in perhaps telling your own story to other people you meet along the way. and I would love to hear you describe how you first met Toby. So who is Toby? How did you guys first meet? And how did you become involved with this whole shebang? So I mentioned earlier, 2005, I moved to Ottawa on advice of this guy, Phil Reimer. And when I got here, I did not know a soul. I had never even been to Ottawa before. Ottawa is the capital of Canada.

Starting point is 00:47:29 It's kind of between Montreal and Toronto, which are two of the major cities in Canada. So I arrived here and started law school. And I have no friends. I have no family here. One of the things that was really valuable to me in Montreal when I was going to McGill was my tribe, the people that were sort of my people, my community, the people that I hung out with, were also entrepreneurs. And that happened sort of organically, that I just met other entrepreneurs and we became really good friends. And so it just worked. And I began to believe that in order for me to find my new tribe, my new group of people in Ottawa, I needed to figure out where the entrepreneurs were. And I just called a bunch of random business incubator type organizations. One was called Invest Ottawa. And I just asked around where the entrepreneurs

Starting point is 00:48:12 hung out. And someone said, there's a group of entrepreneurs that hang out every Friday night in this coffee shop in Ottawa called Bridgehead. It's like the Parisian poets. I guess, yeah. I mean, it's far less sophisticated than that. And certainly far less glamorous. But I was told that these guys hang out at the coffee shop. And I walk into this coffee shop, and it was a group of five or six people. And some of those people was, you know, it was Luke Levesque, created TravelPod, who then went and built Messenger Kids at Facebook. He actually just recently joined Shopify. It was Sam Zaid from Getaround, which is a San Francisco startup. Aydin Mizrahi, who did Fluid Surveys. He's now doing Fellow. And it was Toby. And Toby was an immigrant to Canada. He'd moved here a couple years prior to that from Germany. He moved here because of Fiona. He met a girl who's now his wife, and he moved to Canada. And he initially, because he couldn't work, he couldn't get a job, someone told him that without having your social insurance number in Canada, you couldn't get a job, but you could start a business. That entrepreneurship was a thing that you can do

Starting point is 00:49:15 without having any type of permits to be living here, any type of permanent residency. And so he sought out to try to sell snowboards on the internet, built a company called Snowdevil. And at the time, this is like 2004, there were two ways to sell something on the internet. The first way was you paid a million dollars to some sort of enterprise-y type of company, Oracle or IBM or SAP or just these big enterprise companies. And they would do this big, massive installation for you for e-commerce. But it was really expensive. On the other side, you could use and sell your stuff on a marketplace like eBay or any marketplace that allowed third-party sellers at the time.

Starting point is 00:49:56 And even though that was inexpensive, it effectively meant you were renting customers from that marketplace. You never actually owned your own set of customers. And so Toby being Toby and being this incredible software product genius, and I say that you know him, so you know that that's completely accurate. Yeah, that's not an exaggeration at all. He didn't like those two options. And so he created a third option. And he wrote this piece of software. He was using a new coding language that at the time was incredibly contemporary called Ruby on Rails. He was one of the core members of Ruby on Rails. And he wrote this piece of software. He was using a new coding language that at the time was incredibly contemporary called Ruby on Rails. He was one of the core members of Ruby on Rails. And he wrote this piece of software to sell these snowboards. And he had a really good snowboard business, Snowdevil. It was a really cool business. But eventually, as the summer came and people were

Starting point is 00:50:39 not buying snowboards anymore, he had a decision to make. Either he would start selling skateboards or something for the summer, surfboards, or he would take the thing that he had built for Snowdevil and allow other people to use it to build their own online stores. And he decided to do the latter and focus on the software side. The snowboards were a good idea, but he really believed the software side of it was a great idea. And he created Shopify. And this idea was anyone that had a product to sell was able to use Shopify and very easily set up a beautiful online store. And I was one of the first people that used Shopify. I met him at this coffee shop. I told him that I was looking to move my t-shirt business from a wholesale promotional business, which required face-to-face engagement, into more of a virtual business that would run while I was sitting in tax law and in my classes in law school. And I became store 136. I built a

Starting point is 00:51:37 little store called Smoofer, S-M-O-O-F-E-R. Yep, that's true. What the hell is sleuthing? This was sort of the time like Zappos and Google, a lot of the company names of that vintage were kind of made up words. The next iteration was theify vintage, and the next iteration was the.io vintage. But this vintage, when I started, it was just a lot about finding random words and the URLs and.coms were available. So I started this little t-shirt business called Smoofer. It was a licensed t-shirt business. So I owned the rights to some of the Marvel comics

Starting point is 00:52:16 and DC comics and some of the rock bands licensing. And just started selling these t-shirts on Shopify. And more importantly, or equally as important, at the same time, I really started to develop this wonderful friendship with Toby. You know us both really well. Him and I are polar opposites in most ways. He is cerebral. I am incredibly extroverted. He's a little bit less extroverted.

Starting point is 00:52:40 I know you've referred to me as a power extrovert. A little bit less extroverted. He's a little bit less extroverted than me. The way that he sees the world is very different than the way I see the world. And in many ways, we really connected on a mutual admiration and mutual love of entrepreneurship and company building and commerce. But we also enjoyed each other's, the differences of each other. When I was first setting up Smoofer, I wanted him to waive the fees because he was a friend of mine and I thought he should waive the fees for Shopify. And so I would basically call him every single week and ask him to waive the fees. And I think eventually he got so annoyed that he just made my store completely free.

Starting point is 00:53:18 And years later, of course, when I decided to join, he would say that I was this monster and he made me his monster as opposed to be on the outside. But we became really good friends. And throughout law school and business school, I was a Shopify merchant. I fell in love with Shopify. I thought, how incredibly democratizing is it that me, I was probably 22 years old at the time, some punk kid, I didn't have that much money. I had enough that I was able to start a store, but not enough that I was able to do anything meaningful, that I was able to build a beautiful business while sitting in tax law class that was able to compete against the largest companies on the planet. I mean, the other folks that had the Batman Dark Knight license was

Starting point is 00:53:59 Walmart in Canada. So I mean, literally, I was sitting in tax law class as a complete nobody. And I was competing against one of the largest companies in the world. And I was only able to do it because of this piece of software. This software was just magic to me. Let me hit pause for a quick second. We're going to come back to the magic of the software. I want to talk about how the hell you got the licensing agreement. If you're selling faculty of law, faculty of this, that, and the other thing, t-shirts, how did you go about getting the other license aside from Walmart to sell these? So the licensing world is really interesting because what happens is you have what's called a master licensor who has the rights.

Starting point is 00:54:43 And it's not always DC or Marvel or even some big company. It's sometimes maybe based on some sort of legacy or some sort of, yeah, like a legacy deal. Someone acquired the licenses a long time ago and has held onto it. But then you have these things called sub-licenses. And what was neat about that was there was no way that I was able to afford the license for any of these t-shirts or any of these logos in Toronto or Vancouver or Montreal. They were just too big of a city and they were too expensive. But there were all these, not even secondary cities, these sort of tertiary cities or tertiary regions where no one had the license for it. No one really wanted the license for it. And my thinking at the time was, one of the shirts that did really well was when the Batman Dark

Starting point is 00:55:25 Knight movie first came out. So I think it's around 2006 or 2007 at this time. I knew that I was able to acquire for a limited period of time the license for the Dark Knight Batman logo, which was sort of the new franchise and was getting a lot of attention. And I knew I was only able to afford to have that in particular cities and no one wanted it. So what I tried to do is I tried to find cities where there was a movie theater, but there was no shopping mall. My hypothesis at the time was kids and young people are going to go out and watch this movie and they're going to come home. They're going to say, hey, I want a t-shirt with Dark Knight on it. Where am I going to go to buy it? Likely they'll go to Google, they'll type in Dark Knight t-shirt, and I can simply bid on the

Starting point is 00:56:03 keyword in that particular geography because no one else was doing it at the time, and Google AdWords was still fairly new. And it would result in them eventually coming to my online store. So I did not have the rights to sell this in any major city, and frankly, any city with more than 100,000 people. But I had lots of small areas, geographies across Canada, where I was able to sell it to a very small demographic. And it only lasted like, I don't know, two years or so before some big company came and bought all of these licenses and I wasn't able to sell it anyway. But that's kind of how I did it. And actually, in hindsight, I've never even thought of it in this way, but it was almost like licensing arbitrage, where no one wants it here, but there's value to it, but no one actually

Starting point is 00:56:43 recognizes the value to it because they're using a physical retail business case or business model for it. But if actually, if I'm selling it online, then who cares where they're based? And that's kind of how it happened. That's amazing. When did you, or I should say rather how, when is also pertinent, but how did you end up joining Shopify? What was the conversation or the email? What was the actual process? So now you're winding me up. So after grad school, I moved to Toronto. So I think this is how it works in the US as well. But after law school, in order to get called to the bar and officially be a lawyer, you have to do this thing called articles, which is a 10-month program. You have to work at a big

Starting point is 00:57:28 law firm or any law firm for that matter, but you have to work at an accredited law firm. You have to work as an articling student. And then after those 10 months, you write the bar exam and you get called to the bar and then you're a lawyer. And that's all. That process is finished. I moved to Toronto in 2008 to article at a fairly large law firm in Toronto. And for the first time in my entire life, Tim, I realized what people were talking about when they were using expressions like a case of the Mondays or TGIF or living for the weekend, that my entire life, my relationship with work, whether it was DJing or selling t-shirts or it was sort of hustling through school plus also having an online store. My relationship with work was always that of one, great passion, but also

Starting point is 00:58:13 great love and great fun. And I loved working. I found it very satisfying. And I liked the challenges of it. I liked the satisfaction of learning new skills. And that all went away at this law firm. Whereas entrepreneurship to me felt like a true meritocracy. Law firms, and probably accounting firms too, and some other big companies like that, or industries like that, they all probably have this as well. It felt a lot more like it was all about legacy. They wanted to know who I knew. They wanted to know how many years I'd been there. Because I was a first-year lawyer, I was being given work that was appropriate for a first-year lawyer as opposed to being given work based on my capacity. I was told to do things in a certain way because that is what articling

Starting point is 00:58:59 students do. And because I was a first-year lawyer, because I didn't come from some fancy last-name family, I didn't necessarily understand how to do well in that environment. In fact, it completely depressed me. I thought I didn't like what work was becoming for me. My Sunday nights were the worst period of the week. I would get this knot in my stomach. And what I loved about entrepreneurship was my Sunday nights always felt like my Friday nights. And I love that about it, that Saturday morning or Monday morning, it all kind of feels the same. And so probably halfway into the article, so month five or six of working at this law firm, I called Toby and said, I really want to join you. And at the time it was Cody and Daniel as well. And I really want to join you guys and help you build something big and meaningful and important. And it was mostly

Starting point is 00:59:50 Toby, Daniel, and Cody are three of the most brilliant humans I've ever met. They're certainly on the technology side and the R&D side. And I felt I can come in and help on the business side. And that was that first call. And I think after I had to meet our original angel investor, it was a guy named John Phillips, who's still on our board now. And I had to meet John in Toronto for coffee and had to convince John that I was the right person for this. And I think after trying to convince everyone over a matter of months, coupled to the fact that Toby had already known me well, both as a friend, but also as a merchant on Shopify, as a customer of Shopify's, in early 2010, I joined the company. And I think my original title was VP, in early 2010, I joined the company.

Starting point is 01:00:30 And I think my original title was VP, BizDev, and Legal Counsel or General Counsel or something like that. And that was about 11 years ago. Wow. Seems like a lifetime ago. And we were talking about storytelling earlier. Let's go back to some of the early fundraising. Because fundraising is a dance. And the entrepreneurs make their pitch and then depending on the dynamics of the deal, how

Starting point is 01:00:53 many investors want in or not, the investors also have to make their own pitch as to why they should be part of the deal. I'm just curious to know if you have, we spoke in brief about one before we began recording. That is how certain investors were able to get on your cap table, as they call it, becoming part of the equity structure of the company. Do you have any memories from the early fundraising days, whether it's from the Shopify side of things, from the investor side of things, any particular items or memories stick out to you? Yeah. We decided to raise our Series A, I guess, around the summer of 2010. We decided that it was time for us to raise our Series A.

Starting point is 01:01:42 And that interest or that appetite to raise some money was based on the fact that we began to understand our business, not completely, but at a deeper level than I think we previously did. We understood what were some of the puts and takes of the company, how to spend a dollar here to make $1.80 on the other side. And so therefore, the more dollars we had on the left side, the more $1.80s we get on the right side. We also realized that we were kind of doing this alone. We didn't necessarily have too many folks around the table that understood our business and understood software as a service, as a business model, that understood retail and commerce. And it just felt like the timing was right for us to raise around. The first thing we did was we had asked ourselves,

Starting point is 01:02:24 who are we already working with indirectly? Whose counsel are we already taking without even realizing it? And I think around the time, maybe a year earlier, Bessemer Venture Partners had written this white paper, which I think is still available online. It's called The 10 Laws of SaaS Businesses. And the white paper, it was great. It was important for a couple of reasons. One, it gave us the nomenclature that even today we still run the business with, things like monthly recurring revenue and ARPU and customer lifetime value. And it provided us with a set of calculations and formulas that allowed us to know whether or not our business was healthy or not.

Starting point is 01:02:59 And just a quick pause, just for acronyms for those who might not know. So SaaS is software as a service. ARPU, average revenue per user. Is that right? Am I getting that right? Yeah. And then customer lifetime value is LTV. Our customer lifetime value is LTV. And it was instructive. It was valuable. So funny enough, we were already kind of working with Bessemer, even though Bessemer had no idea that we were doing this. Now, maybe this is an entire pitch for... You see so much content coming out from the investment community, whether it's white papers or blogs or podcasts. But in this case, it absolutely worked for us. It was incredibly effective because it showed us, wait a second, there is a venture firm out there. There are a bunch of partners out there who really understand

Starting point is 01:03:42 our business at a very deep, sophisticated level. And so we knew that Bessemer, we wanted Bessemer around, and they ended up leading the Series A. But there were two others that, I mean, a bunch of other people had heard we were raising, and we got some inbound interest, which was really great. But there were two others in particular that really kind of set themselves apart. And one, I found out earlier today from you, actually, you have a connection too. I didn't actually know this story until this morning. But at one point in the middle of the fundraise, in the middle of deciding what the round was going to look like and who were the investors

Starting point is 01:04:15 going to be and what the terms of the deal was going to be like, someone showed up at our door in Ottawa. We were in this area called the Byward Market in Ottawa, right above a restaurant. It wasn't necessarily a fancy office, but someone showed up and his name was Aydin Senkit, door in Ottawa. We were in this area called the Byward Market in Ottawa, right above a restaurant. It wasn't necessarily a fancy office, but someone showed up and his name was Aydin Senkit from Felices. And he showed up. And I know now it's like, well, I mean, if you want to do a deal, you show up. But at the time, no one had really ever shown up at our door. Certainly not some well-known, highly respected investor from Silicon Valley who cut his teeth as an early employee at Google and had this great reputation. But I didn't show up. And once you talk to him, you realize how smart this man is and how intelligent he is and how

Starting point is 01:04:56 experienced he is. But just him showing up was such a wonderful... Him and I talk about this story all the time now because it's just a great story. But that's in a nutshell where others would write an email or phone you or want to do a video conference. His style is you show up. And he ended up coming to the Series A, which I think and hope it was a really good investment for him. And Firstmark also, Firstmark Capital from New York, also joined. Same type of dynamic. They simply, Amish at FirstMark really just showed up and helped us the second we encountered them. And that was our series A. It was a $7 million round. I think it was a $25 million evaluation, maybe 25 post. And that was our series A in 2010. So Aydin, for people wondering, is A-Y-D-I-N. Last name Sankut, S-E-N-K-U-T. So on Twitter,

Starting point is 01:05:43 he's A-Sankut. And he's an investor in lots of stuff. So you've got Shopify, Fitbit, Pluralsight, Rovio, Notion, and many, many others. Very successful. Very nice guy also. Here's a story about him. In the early days after he invested, one of the things we needed was we needed a merchant that was going to sell at scale because we needed to test the resiliency, but also the scalability of Shopify. And Aydin heard this and immediately connected us with Rovio. And so I don't know if you remember this, but Angry Birds was just... Rovio's major hit is Angry Birds. Angry Birds was flying in, I think it was 2011 or something like that.

Starting point is 01:06:22 And the brand, I think they were from Finland, if I'm not mistaken. The brand just blew up. They had Angry Birds Cola and they had Angry Birds clothing. But their plush toys was one of the most hottest selling items of the season. And hearing that we needed to test the scalability, but also to show that you can sell at scale on Shopify, Iden connected us directly with the Rovio people. And within a matter of a week or so, they had launched the Angry Birds store on Shopify. And that really was one of our first major blowouts in terms of demonstrating the scalability of Shopify. And that's the type of investor he is. I have to wonder what his pitch was to them. I'm pretty sure it wasn't,

Starting point is 01:07:01 they want to see if their software will break. I can't imagine. I assume it was a lot more of, hey, these guys are amazing, the best platform ever. Of course, they have lots of at-scale stores, and so you don't have to worry about them. But what was interesting was Aydin had come to you because of our existing relationship, and you had made the intro to us from Aydin. And I actually didn't know that until this morning. Yeah, it's pretty wild. And just for this background context for people who don't know, Toby and I had met in 2009 at something called a Rails Conf. You mentioned Ruby on Rails. And for simplicity, let's just call Rails Conf a

Starting point is 01:07:36 developer's conference. Why I was there was, I mean, I think I was largely there as kind of a sideshow curiosity, but that was two years after the four-hour work week, and it had struck a chord in Silicon Valley. And rightly or wrongly, there I was in the green room, meaning the backstage room or location where speakers kind of hang out before they go on stage. And that is where Toby and I had our first meaningful conversation. Then later, I was lucky enough to become an advisor to Shopify. And so from that point forward, it was along for the ride. And you actually gave us one of the best pieces of advice as an advisor. I don't know if you remember this. And I'm going to butcher the exact quote you gave us because I'm sure it was far more eloquent than what I'm about to say or articulate. But you said, what you guys are building is great. The problem is that most people that think about entrepreneurship immediately think it's either too complicated or too expensive or too difficult.

Starting point is 01:08:37 And that if Shopify was going to be something important in the world, we not only had to build great software, we also had to convince the world to try their hand in entrepreneurship. And that was one of the biggest pieces of insight, certainly in the early days, we ever had received. And that came, that was from you, and we're internally grateful for that. I appreciate you saying that. The build a business competition, I would love to know how you think about it when you're remembering it. Because I remember the conversations very early on with you, with Toby. I remember walking past, up and down the sidewalk next to this Thai restaurant in San Francisco. I remember exactly where it was, on Diamond Street in San

Starting point is 01:09:19 Francisco, back and forth, back and forth, past the bodega on the corner and having this conversation, the very first conversation about what would later be the Build a Business competition. But how would you like to contextualize this for people? Because it is a good example of a way to differentiate yourself and generate both attention for brand purposes and user signups that might be instructive for folks who are trying to find a way to stand out from the noise. Yeah. Are you familiar with the Jeffrey Moore book,

Starting point is 01:09:55 Crossing the Chasm? Yes. Okay. So fundamentally, if you were asking what Build a Business did for Shopify, it allowed us to cross the chasm from early adopters that were using it. And this is sort of, I mean, the neat part about Toby writing the software in Ruby on Rails is we

Starting point is 01:10:10 got some early traction from that Ruby on Rails crowd. And that was great. But the mainstream had never heard of Shopify, had never heard of any of us. It just, it was unknown to them. And so your comment that, hey, you guys have the right software for anyone who has already decided they want to be an entrepreneur, using Shopify is a great idea. But what about people that have not yet made the decision? Because for 99.99% of the world, entrepreneurship is out of reach. If you don't know an entrepreneur, if you have never started a business yourself, it does feel intimidating. It does feel out of reach. And through this conversation, somehow we landed on this idea that what if we created a competition as a proverbial kick in the butt to convince folks to try entrepreneurship and use Shopify. And the store with the highest sales would win

Starting point is 01:11:06 $10,000. And I distinctly remember you saying, yeah, that's bullshit. $10,000 is nothing. You got to give out $100,000, which was most certainly more money than we had in our accounts. Certainly more money than any of us had combined. You could have said a billion dollars and it would have been the same thing to us. That's how much $100,000 was. But this idea that, and frankly, I now realize how much foreshadowing that was in terms of the company that we are trying to become, which is the world's entrepreneurship company. We wanted Shopify to be more than a software company. We wanted to create a movement. We feel that the world is better with more entrepreneurs. How do we get more people to try their hand at entrepreneurship? And in the same way, one of the amazing marketing hacks that Nike did, and they deserve all the credit in the world for this,

Starting point is 01:11:56 they convinced the world that anyone that has a body is an athlete or can be an athlete. That was completely different than the previous iteration of who wore those early iterations of Nike shoes, of running shoes. It was for people that lived in Oregon and went to Oregon State and ran track and field. But they convinced the whole world that if you have a body, you are absolutely an athlete. And I think what we began to do through this Build a Business competition was try to convince people that if you have ambition, you can be an entrepreneur. And we did that by virtue of, frankly, bribing them to start a business by offering a $100,000 prize to the store that sold the most.

Starting point is 01:12:41 And it was a very simple competition. You start up on day one. Six months later, we evaluate who did the most sales, and they a very simple competition. You start up on day one. Six months later, we evaluate who did the most sales, and they got a $100,000 check. And what was neat about it was we got a lot of attention. We were in the New York Times, and that was a really, really big deal for us at that time. I don't know the headlines offhand, but it was something like, a startup creates their own startup competition. And it was a really meaningful thing for us. And the Build a Business competition ran for five years after that. And frankly was a really meaningful thing for us. And the Build a Business competition ran

Starting point is 01:13:06 for five years after that. And frankly, we're now actually thinking about what the new iteration of it is for next year. But it ran because it became such a big part of our story. And some of the greatest direct-to-consumer brands on the planet were created through Build a Business. And so it's a part of our story. It seems like it was just a campaign, but it was so much more than that. It defined, but let's just look at it in the context of entrepreneurship. Let's just say $50,000 puts you in the category of, I'm using that arbitrarily, but $10,000 or $50,000 puts you in the category of business competition. And there are other business competitions that have done $60,000, $70,000. There is a day and night binary difference between that and being in the category of one, which is the largest X ever or the first Y ever. And sometimes it's really just an incremental difference,

Starting point is 01:14:27 even though at the time it might seem overwhelming. You pretty quickly realize, it's kind of like the book I mentioned earlier, the draft number four. Until you have a first draft, the whole thing seems overwhelming and unwieldy because there's nothing to refine. But as soon as, and I remember this, as soon as the sort of parameter as a draft became, not could we, but what would it look like to have $100,000 prize and this competition? Then you start to find ways to mitigate risk. You start to find ways to look at it as an expenditure over time. And you realize that it's certainly not going to be a $100,000 loss if it's a failure. And if you shoot high, I think it's Larry Page who's fond of saying something like this,

Starting point is 01:15:19 but what a lot of people miss is that if you aim really high, it's very hard to fail completely, right? And then you guys did it, right? And you had the New York Times coverage and you were extremely newsworthy, right? Because you were doing sort of, you had the biggest ambition and you were also breaking ground as a first. Yeah, it was ballsy. But the thing that actually is super interesting

Starting point is 01:15:42 is that what you, we didn't necessarily realize at the time, you only have to pay it out at the end of the competition. So you don't actually need $100,000 when you get started. You just have to be able to acquire enough revenue over the period of six months to actually pay that out eventually. And that was sort of an interesting, oh, right, we don't actually need the money right now. Funny enough, there are certain states and certain Canadian provinces that require you to post a bond in the amount of the prize in advance. I think you and I have talked about competition law before, in advance of it. So we actually couldn't necessarily offer it everywhere because of

Starting point is 01:16:19 some what they call sort of gaming law. But absolutely, it was bold. It was ballsy. It was an interesting thing that a small company was doing. And we had 1,300 contestants sign up for Build a Business in 2010. And the winner was a company called Dodo Case, which made the most beautiful iPad cases and ended up... Obama was using one at the time and he was photographed using his Dodo Case. And they also did some really cool stuff. They completely rejuvenated the bookbinding industry, which had been effectively shut down in San Francisco. And they brought these bookbiners together and started making iPad cases. But the neat part was the big takeaway from year one was some of these businesses were growing so big that the $100,000 or frankly, any amount of money, unless it was something absurd, was not

Starting point is 01:17:06 going to be enough of an incentive. And so as you recall, on year two, we changed the prizing to be once-in-a-lifetime opportunities, to be things that basically money can't buy. And a lot of that was connecting the winners with some of the most interesting people in the world who were incredibly generous with their time and wanted to kind of help out. And we brought on people like Seth Godin, and we brought on people like Gary Vee, and we brought on people like Richard Branson, and Tony Robbins, and Marie Forleo, and Debbie Sterling, and Tina Eisenberg. And we brought these incredible mentors aboard. And instead of giving out $100,000, we said, hey, the winner's going to spend a week with us and a bunch of really interesting people

Starting point is 01:17:51 on Richard Branson's private island in Necker, in the BVIs. And I think the last year we did it, we had over 10,000 contestants. And we've actually since then have done a build a bigger business competition, which is million-dollar businesses who can actually grow the fastest, 10x, 20x. And one of the winners of the last one was Gymshark, who as of last week is now a billion-dollar brand. Now, these businesses may have started regardless and despite build a business competition. Ben from Gymshark probably would have started no matter what. But what the competition fundamentally did was it provided this catalyst to get started right now. And that is why I think it was such a powerful initiative and movement for Shopify. And we are forever grateful to you, Tim, for really

Starting point is 01:18:36 bringing us that because our trajectory has been forever changed because of Build a Business. It's been so much fun and such a pleasure. You know, I love to talk about the future of retail. And I'll tell you something I don't think you know, which maybe you do. I don't think so, though, because we haven't talked about it, is that I remember when Shopify went public and spending time there in New York on Wall Street

Starting point is 01:19:02 and hanging out with you and everyone's families and so on. And then not too long after the IPO, realizing that it was a life-changing sum of money for me at the time, having not lost any confidence whatsoever in you guys as a team or a product, but I took my stake off the table. And it's always been this huge source of guilt and shame for me. And so I was eyes wide open when in, let's say, late March, early August, I decided to come back in and put the Shopify jersey back on and buy back into the company. So I am as bullish as I've ever been. Obviously, I'm not a registered investment advisor, blah, blah, blah.

Starting point is 01:19:50 I'm not giving investment advice. But I feel like that sort of psychic load of guilt and shame has been lifted, which I'm thrilled about. And I wonder if you could talk to the extent that you can, what has happened in the last few months and the future of retail? What are the things that people are missing? What are some of the maybe assumptions that you have or things you think are coming down the pike? You have such a unique vantage point because you're not only seeing Shopify, right? Much like a Stripe is not just seeing Stripe internal finance. It's like they get to see who is growing fastest or any payment processor for that matter who is handling

Starting point is 01:20:37 this type of stuff. So you get this incredible perspective on the ecosystem of a million or a million plus companies, not just Shopify itself, if I'm phrasing that in an intelligible way. So how would you talk to what's happening, what has happened in the last few months and the future of retail? Yeah. So first of all, you said this earlier, but this idea that the year 2030 has been pulled into 2020, that's a real thing. And what I mean by that, when I say it is that the retail dynamic that would have existed, meaning percentage of total retail that was done online, laggards that have began to digitalize their business from a commerce

Starting point is 01:21:17 perspective, that has all happened rapidly in three months. And so if you look at e-commerce as a percentage of total retail, when I joined Shopify, it was approximately 5%, something like that. And last year, these are US numbers, last year, e-commerce was about 15% of total retail. So we've grown about 10% in 10 years. We're now at close to 25%. So since March, the amount of acceleration in shifting total retail to online retail has been dramatic. One is, I'm surprised by how quickly that happened. I'm not surprised where we ended up because I think we would have ended up here anyway. Two things have happened. The first thing that has happened is you see two types of entrepreneurs existing right

Starting point is 01:22:08 now. I mentioned these terms earlier, but it's worth repeating. You have these resistant retailers and entrepreneurs and brands who simply did not adapt and pivot fast enough. And they are suffering. I mean, you're seeing iconic brands, whether it's Barney's or it's J.Crew, name your pick, that have gone out of business because, frankly, they simply didn't see the future retail coming in the way that it has materialized. So, for example, a lot of these brands that went out of business, they lamented

Starting point is 01:22:36 the fact that their e-commerce efforts was hurting their offline commerce efforts, which is ridiculous. You talk to any of the guys at Allbirds, for example, they couldn't care less if you buy it in-store, online, or on social media. They just want you to buy their shoes. And their online store may be a catalog for their offline store, or their offline store may be a showroom for their online store. They are completely channel agnostic. They just want you to have a great experience and buy a great pair of shoes from them. But a lot of the big brands didn't, and they resisted this change. They fought it. But then you have this other category, these resilient retailers. We talked about Gymshark earlier in context of Build a Business. The day that COVID hit, they're based in the UK, they were told that gyms where people work out

Starting point is 01:23:19 were going to be closed. They rebranded their homepage as HomeShark instead of Gymshark. They immediately changed their content and their distribution and their influencers. And everything about that company changed within 24 hours because the world changed. Immediately, people were not doing the same thing as they once were. And you see that across a whole bunch of different categories across Shopify, these great brands that have just completely pivoted. You've seen restauranteurs that are doing meal kits and they're turning their restaurants into wine shops if you can't go in there. You're seeing grocery stores that historically never even came close to Shopify, it wasn't

Starting point is 01:23:57 a vertical of ours, are now signing up for Shopify and doing their top 12 most popular items and setting up a beautiful store. Chipotle has a store on Shopify right now where they're connecting Chipotle consumers with the farmers who are their suppliers. They're basically creating a Chipotle farmers market for consumers on Shopify. So on both sides of the coin, you see totally different stories. And I want to focus on the resilient side because, frankly, that's the real story here. The real story is that consumers generally have now decided,

Starting point is 01:24:31 and this is consumer behavior, that they would prefer to buy products from independent brands, from actual entrepreneurs, from the makers of the products, if they can. But for a long time, the supply wasn't there. So consumers had to buy through intermediaries. Well, the cool part about all this is that the supply side is now caught up. So now you have on the demand side, you have consumers who want to buy directly from the brands. And now you have the brand selling direct to the consumer. And so you have this new retail model. And it's not necessarily just going to be online or it's going to be offline. The future of retail will likely be retail everywhere. And it's going to be about consumer

Starting point is 01:25:08 preference, which is so different than, think of when you were a kid and you wanted something, you wanted a video game. You would be forced to line up on a Saturday morning at some game stop in the mall at nine o'clock in the morning, and the doors open, you ran in to grab the video game and then you left. That's how it worked. The retailers have historically always dictated to the consumer how, when to purchase. And what's happened now is consumers are saying, no, no, no, I want to purchase in the way that is most convenient for me. And a lot of that is online, but it's also offline. And it's also across marketplaces and social media. Fundamentally, commerce has been changed forever. Now, will the growth rate of e-commerce continue to grow at this pace? Probably not. It got pulled forward. It'll

Starting point is 01:25:55 probably stay around where it is right now. But fundamentally, consumers who never bought online before and have been forced to buy online over the last three, four months, there's no going back to the way it was. There's no way my grandparents are going to go out in February in Montreal to buy groceries when they know that they can now use their iPad to easily buy off one of the grocery stores, online stores. And I actually think this is one of the most exciting times for retail of the last, I don't know, call it 150 years. It is a tale of two worlds. And I hope some of these resistant retailers begin to simply wake up and realize that everything has changed and they don't have to be left behind. Here's a cool example. When you think about these resilient retailers, you often think of the Gymsharks, the Fashionovas,

Starting point is 01:26:44 the Bombases, the Tommy John Underwears, these amazing, incredible, iconic DTC brands. But we've seen Heinz ketchup go direct to consumer during the pandemic. We've seen Lindt chocolate, Snickers, shoe and bicycles. Some of these brands are brands that I have personally been calling for five or 10 years to try to convince them to come on to Shopify to sell direct to consumer. And they just never did it. And now they are because they have no choice. So it's a really interesting time for retail and commerce. And those brands that have been able to pivot and adapt, they are doing incredibly well. But there are those that simply haven't made it. And I think a lot of them were just waiting for things to go back to the status

Starting point is 01:27:25 quo, to an old version of retail. And I just don't think it's going to happen. Yeah. I don't think it's going to revert to at least what the previous normal would be anytime soon. And I remember the night that I decided to jump back in to bed with you guys. And it was very specific. A couple of things that happened. A, you guys have been unfairly, well, as far as I'm concerned an investor in Amazon, but I had gone to order some coffee filters and I couldn't order coffee filters or I could, but rather than get it through prime in one to three days, it was a three to four week lead time because it was not categorized as essential, which is exactly what Amazon should have done, I think. But I thought about it, not from the perspective of customer inconvenience. I thought about it from the perspective of cash flow and survivability from the perspective of the person who's selling those coffee filters.

Starting point is 01:28:38 You had mentioned renting customers. And I have friends who run very large e-commerce brands and small, medium, and large brands everyone would recognize. And a lot of them have bought Amazon stock once they saw a double-digit percentage of their sales move to Amazon, whether they liked it or not. And to me, what that says is a lot of people having that experience with the coffee filters, a lot of companies were going to get caught between a rock and a hard place where they couldn't email their customers and say, hey, come over to this other store if they had one, because you'll have to wait a month on Amazon otherwise. And they were dependent on that rented customer base

Starting point is 01:29:27 they couldn't contact directly. And I thought, okay, at the very least, this could be a fatal shot, like a headshot for a lot of companies. But for a lot of them, it's going to be a flesh wound. It'll be like a shot in the leg, and they're going to say, holy shit, we at least need a plan B so that there

Starting point is 01:29:47 is a Google discoverable storefront for our products if this ever happens again. And that was sort of the assumption that, not to mention the fact that if anybody, this is just sort of me reading stuff on the internet, if anyone from a large tech perspective wants to integrate some type of e-commerce capability, there just aren't that many viable players. So Amazon is completely fully integrated, vertically integrated. But if you look at other shops that might only represent one layer of the stack, so to speak, Facebook or whoever it might be, their options are pretty limited. I mean, they can build in-house or they can partner with someone who's already built out the infrastructure. And the neat part about that is we actually don't

Starting point is 01:30:37 want to sell ads, right? So we don't want to be a social media platform. We don't necessarily want to be a place where you're able to scrapbook your favorite products like Pinterest does or to organize your home furnishings desires like Houzz or to do any of these things. The neat part about our positioning is that we simply want to encourage more people to try their hand in entrepreneurship and to become retailers. And the idea that, to your point earlier on the pandemic, I think a lot of consumers are thinking about their local small businesses. And I think we all are. I mean, our communities are now becoming far more important because frankly, I spent 100 nights on the road in 2019. I'm going to spend five nights on the road in 2020. My community here in Ottawa is becoming incredibly

Starting point is 01:31:21 important. So whenever possible, I want to support my local stores, my local restaurants, my local cafes as much as I possibly can. And one of the things that I think will remain after this is the importance that what gives our cities and our towns and our communities character are the small businesses. But in order for the small business to survive, in some cases, they have razor sharp margins. In other cases, they have larger margins. But we want, as consumers, to make sure that our money that we're buying, the money that we're using to buy stuff with, is going to the people that actually are behind those companies. That in order for retail and commerce to thrive long term, it needs to be in the hands of the

Starting point is 01:32:01 many, not the few, which is why we talk about this idea of Shopify wants to arm the rebels. We want anyone that has some idea, some passion, some vision to build something to be able to do so and to own their business themselves as opposed to renting their business from somebody else. And actually, I think one of the great things that will come out of this is this consumer trend to support independent business as much as possible. I don't think that's going away after this. Yeah. If it's easy, right? If it's easy. And that's a super key component of all this. Let me ask you about mentors and actually mentors in a different capacity than we've been referring to them. And that is coaches. So it seems like, and this is something I wasn't aware of, but that you have coaches internal at Shopify available to folks. The story I read talks about Cody Fowler, I guess it is. Is that correct? And his experience with coaching.

Starting point is 01:32:59 But how do you use coaches and how are coaches used at Shopify? Yeah. So Cody was our original CTO and one of the first guys of the company and certainly someone who's been a big part of the Shopify origin story. At a particular point, he was running engineering and he realized that his team was getting bigger and bigger and he didn't necessarily have all the tools he needed to be the right leader. But in this sort of theme, in this sort of lens of we always requalify for our jobs every year if we want to keep our jobs. Cody, I apologize to interrupt, but since this

Starting point is 01:33:30 has come up a couple of times, what does it mean to requalify for a job? You're getting effectively hired each year anew. I mean, is that metaphorical? It's more of a loose philosophical guidance, or is there actually a process for evaluating whether you qualify or don't qualify? What does that mean? We think it's a very valuable personal growth sort of philosophy that this idea, and I can't speak for everyone, but I certainly speak for myself, and I know Toby feels the same way in his role. Every single year, I still have to be the best possible chief officer for Shopify. And if I'm not, that means that someone else should take my role. And the reason that's important is because the pace that Shopify

Starting point is 01:34:11 is growing at, and has been growing every single year since I joined it, certainly, I have to keep up with it, but I also have to keep up pacing it. And so there's a lot in that. I mean, Shopify, again, went from being an e-commerce provider for small businesses to being a retail operating system. We have a billion-dollar capital business. We have a fulfillment business now. We're cross-platform. We're publicly traded. And so it's a really, really wonderful model of which to gauge whether or not you are growing at the pace. Because if you say, well, are you growing every year? Most people say, yes, I'm growing. I'm learning new skills every single year. But if I use the lens that if the greatest chief operating officer in the world walked in to see the board of Shopify and said, hey, I want to be your COO, I need to know

Starting point is 01:34:54 that I am still the right choice. And this idea of requalifying for your job from a philosophical perspective has just been incredibly valuable because it means that if I grow at the same pace of Shopify, I still may not necessarily be the right person for next year. So I have to almost outpace Shopify's growth, which puts the onus on me and all of our leaders

Starting point is 01:35:15 to grow at this incredible rate. And whether you call it requalification or you call it disproportionate personal growth, that is something that is baked into the culture of Shopify unequivocally. And it's actually made for a really interesting environment to be at because you have people who so badly want to keep growing. And Shopify makes it difficult to keep up because it grows so fast on its own as its own entity. But that requalification thing I find is

Starting point is 01:35:40 important for me in my own career, has been incredibly valuable in using as a bit of a litmus for my own path. I interrupted you. You were talking about Cody. So I want to take us back to Cody. And it seems like coaches are one of the tools in the toolkit for staying ahead or front running. Yeah, right. I mean, coaching is not anything new. I mean, a lot of leaders have coaches, but Cody kind of discovered this idea of a coach. And then he introduced Toby and I to it. And we really started getting a lot of value from it. And at a certain point, it became clear that we wanted to have

Starting point is 01:36:14 these coaches around more often. So we ended up hiring our first coach. His name was Cam and bringing him on full time. And he really helped coach the exec team at Shopify. And then really quickly- Can you explain? Sorry, I'm going to keep interrupting. I apologize. Please, go ahead. It's my job. What is this coach doing? Because there are, coach is kind of like teacher,

Starting point is 01:36:32 right? There are a million and one different ways to be a teacher, a bad teacher, a mediocre teacher, a good teacher, or a great teacher. And then there are different subjects. What did this coach do with you guys? What you're saying is correct, which is that not every coach is the same. And frankly, a good teacher or a great teacher, and then there are different subjects. What did this coach do with you guys? What you're saying is correct, which is that not every coach is the same. And frankly, one of the problems with coaches in general is that nomenclature, that it doesn't take very much to call yourself a coach. There is no medical school for coaching. I mean, you can take a program or get a certificate, but generally, not all coaches are going to be the right fit, the right match. They're not all going to be of great value. But generally, not all coaches are going to be the right fit, the right match.

Starting point is 01:37:05 They're not all going to be of great value. In fact, I had initially seen a coach I just didn't connect with. He was a very smart person. I just didn't connect with him. But for Cody in particular, he needed a way to scale his ability to manage a team at scale. And so his coach actually happened to be someone who ran a very large engineering team at IBM. And that was specifically the thing he wanted to acquire. For me, I'd spent my entire life, as we've been talking about, as an entrepreneur doing everything myself. And I had a real tough time transitioning from being this entrepreneur, getting deeply into the weeds, doing everything myself, to being really good at hiring and onboarding and managing people, in many cases, that are much

Starting point is 01:37:47 smarter, faster, more experienced than I was. And so one of the things that we had figured out was if we were to bring coaches into the company full-time, it would allow us to provide the coach with far more context for what is the coaching curriculum or the coaching journey that we all want to go on. That if we only see these coaches one hour every two weeks, and they don't deeply understand the Shopify culture, the Shopify company, the people involved, it would put them at a disadvantage for actually helping us achieve this development that we were looking for. And so we ended up just hiring this one particular coach, Cam, full-time, and he was coaching a few of us. And the epiphany there, I suppose, was that by having him much closer to the business as opposed to on the periphery, we immediately got

Starting point is 01:38:36 far better advice and we were able to grow faster. And that eventually led to us saying, hey, what if we actually created a team of coaches at Shopify so that anyone who wants to, or frankly, needs to have a coach can do so. And the onus isn't necessarily on them to find a coach. We'll have a group of coach. They can sort of interview a few of these coaches that we have on staff, but that they work full-time at Shopify. And I don't know, eight years later, I think we have over a dozen coaches on staff at Shopify full-time. Everyone has their own coaching curriculum. Everyone has their own version of progress and development with their coach. But by bringing them into the company, it allows them to have a

Starting point is 01:39:15 much richer understanding of the type of place Shopify is and the type of development that is required. And it's been amazing. And to this day, I still see, I have a new coach now. Her name is Deb. And it's been an amazing journey for me. And in fact, I kind of can't understand, I mean, I talked to a lot of peers who are running companies like Shopify. And coaching, as much as I think it's just obvious that why wouldn't you have a coach, it's not something that is universally accepted. And I'm not really sure why. I think it harkens back to the quality assurance and the difficulty of vetting in part. So let's talk about just to give people who aren't going to be able to hire full-time because there are a lot of companies or people who won't be able to do that, but they're maybe interested in trying

Starting point is 01:40:00 coaching. What happens in that hour every two weeks? And it could be just personal examples, but any specifics would be super helpful. What actually happens? Is there a scorecard? Is there communication in between? What does it look like? And I'm most interested in what it looked like before you hired them. I understand the reasons for hiring them, but at some point, you guys thought to yourselves, this is so valuable, it could be even better. Let's hire them. So they were already demonstrating value. What did the format or what might the format look like? One thing that the coaches that I have seen, one of the things that they have done, which I found very valuable, is they use a metaphor. So for me, I'll just tell you what

Starting point is 01:40:40 the metaphor is because I think it's valuable for the listeners. My metaphor was I wanted to develop from a Mossad commander who's always doing everything all the time and kind of a jack of all trades into more of a sensei whereby I can work with really, really talented people. I can explain to them what destination they need to get to. But in terms of the journey to get there, I can rely on them. I can trust but verify. I can provide them with some breadcrumbs to make sure they're going in the right direction, but that inevitably they will get there on their own.

Starting point is 01:41:15 And that may seem like an easy transition to make. It was almost impossible for me. I found that to be incredibly challenging simply on the basis that, one, I think in the early days, I was really insecure about hiring people better than me. I thought that if they were better than me, what role was I going to play, which was completely ridiculous. And now I see that. And so I had to work on some of that this idea of trust but verify, what do I verify? What do I trust? You've talked to Toby about the trust battery metaphor at Shopify, where everyone starts at 50% trust battery. And through their actions, we watch them hopefully get to 100%, which is where they get autonomy. But these metaphors that our coaches use have been incredibly instructive so that you don't actually know. I'm probably still not at the sensei level yet, but I know that directionally, I'm going in the right direction here.

Starting point is 01:42:09 And that's not necessarily something that all coaches use. The coaching style that our coaches use is called the integral method, which is a bit of a hybrid of a bunch of different coaching styles. But that metaphor to know where I am right now, to know where I want to get to, and then every two weeks on an hourly basis walking through, okay, give me some examples of how you've demonstrated more of that sensei-type thinking and less of the Mossad commander thinking, holding me accountable to that when I provide them with something that is challenging to me, having them workshop with me the right way to do it as a sensei as opposed to a Mossad commander,

Starting point is 01:42:46 man, that has been so, so helpful. It also feels like when you do bring them in, and I'm not suggesting everyone needs to hire a coach full-time because actually, I have a lot of friends who have third-party coaches who just see each other every two weeks. The important part that I have seen is to be really transparent and incredibly clear about, here is the development I'm looking for. Here's what I want to work on. If you just go in with, I want to get better, I want to grow. Is that a personal thing? Do you want to get better in terms of leading? Do you want to get better in terms of your craft? I find the ambiguity that most people bring into coaching is not helpful at all. And if you were clear about, here's what I want to work on, here's

Starting point is 01:43:26 what I suck at, and please call me out on my bullshit with this stuff or hold me accountable to these things, that I think is where you get the most successful dynamic with coaches. And frankly, you may outgrow your coach. Every couple of years, it may be time to get a new coach who has a different skill set. But I have to say, if I had to distill down one of the things that has allowed me to get to where I am at this point with my career and certainly helped me lead Shopify, coaching is up there in the top three or four things that I've done. What else would be up there? Any others come to mind that are in the sort of 80-20 distillation of things that have really moved the needle?

Starting point is 01:44:02 Yeah. Any other items come to mind? This is maybe a personal thing, but even as a kid, I always had anxiety. I never had a term for it. I never understood exactly what it was. I just knew that I had this thing. And I knew it was anxiety because I was always thinking about what's next, the future, as opposed to what people often talk about, a depressive state, which is looking backwards. I was always looking forward. And I had experimented with some mindfulness practices and some meditation in the past, but because I was anxious, in general, I was anxious about meditating, meaning I was always

Starting point is 01:44:35 looking for some sort of quick fix, that if after 10 minutes of meditating, I didn't find enlightenment, I thought it was broken. I thought it wasn't working for me. And which sounds absolutely ridiculous, right? Of course. But meditation has also been something that I've committed to or last probably since 2014. So going on six years now, every single morning, it's either 10 or 15 minutes, depending on how much time I have. And it has made me, I'm by no means, as you can hear from the tone of my voice, I'm by no means laid back or a chill kind of person, quote unquote, but it has made me more thoughtful about how I want to expend my energy. And it has allowed me to focus on the things that are most important, both on my personal life, but also with our business. And man, like, I mean, I know you talk a lot about mindfulness practices and meditation on the podcast, but I am someone

Starting point is 01:45:24 who for years just did not subscribe to it. And it was because I was looking for some sort of quick fix and never came. And once I began to think more long-term about it, to be patient with it, everything changed. And it's been wonderful for me. Meditation is a lot like sports in the sense that there are many different flavors, right? There's badminton, there's curling, of course, not to be forgotten. You've got MMA, you've got hockey, you've got all sorts of different sports, darts. And meditation similarly has many, many, many different approaches. What do your sessions look like? Do you use an app? Do you use transcendental meditation? Do you use open awareness? What flavor of meditation do you use most app? Do you use transcendental meditation? Do you use open awareness? What flavor of

Starting point is 01:46:06 meditation do you use most consistently? So it's funny. I had been historically using just insight timer and just doing like a 50 minute counter with a little bit of white noise to block out whatever's happening around me. But going back to my power extrovertedness, I have found that this pandemic has been kind of lonely for me. And I don't mean that in a severe way. I'm home now with my amazing wife and my two amazing kids, and I have my family around me, but there's a certain lack of social interaction that is missing from me. And so early in March, for the first time ever, I ended up just going to the guided meditation tab in Insight Timer, just because I kind of just wanted to hear someone

Starting point is 01:46:50 else's voice. And I've actually been doing these guided meditations almost consistently since March now. And they range from courses. I know you've talked about Jack Kornfield, Sharon Salzberg, David Gandelman. There's some just trying to look at who else, Sarah Blondin. There's just some amazing guided meditation coaches on Insider, frankly. I mean, you can probably do it on YouTube as well. And I actually have found that guided has been, it's like a warm hug for me in the morning where I hear this really wonderful, calm voice taking me through a 10 or 15 minute sit. And I always end up on the

Starting point is 01:47:25 other side so much better. And so I started with counting breaths. I'm now trying to do a little more mantra-based TM-style stuff. But the truth is, it really depends on the day. And I'm trying not to be too hard on myself about that experience. That if on a Monday, I had this great sit and I come out completely mindful and relaxed and focused, on Tuesday, if I don't have that same experience, I don't want to forego Wednesday. And the way that I'm able to have consistency is just to take it easier on myself around my own version of what a successful sit looks like. And I think today a successful sit for me is really just the ability to sit for 15 minutes consistently every single day, no matter what I feel afterwards. It's a very important point. And I'm by no means a mindfulness expert,

Starting point is 01:48:16 but it's the consistency. And I think blocking out that time, that is the prerequisite for almost everything that follows. Because by blocking out that time, especially if you've operated in sixth gear for a very long time, which you and I both have, it's very easy to try to cram as much as possible into your waking hours. It's easy to do. And it's compulsion as much as it is anything else. And by blocking out 10, 15, 20 minutes to do nothing, you build in, I think, a sense of luxury in so much as you are not rushing yourself. And that has many downstream effects, even if you're just like thinking about your to-do list and staring at the ceiling for 20 minutes. Yeah, totally. I totally agree with that. Sitting there and you're not on a keyboard, you're not staring at a screen, you're not checking your phone. Yeah, totally. I totally agree with my wife blocked out of my calendar, which again, sounds completely lame and unnecessary. But what it does do is that pop-up comes up on the top right side of my screen and suggests, hey, it's family time. Or hey, it's a walk. My wife, Lindsay, who you know, is also an entrepreneur. We're very busy. We have two little kids. So scheduling a walk together,

Starting point is 01:49:42 as ridiculous and silly as it sounds, is incredibly valuable. Because also, if we don't take that walk, it's staring ourselves in the face that we skipped this walk to do something else. So the question is, was the thing we skipped that walk for as valuable as the walk would have been? And the answer is, most times, no, they're not. So actually being meticulous with our calendars and our schedules, especially with two entrepreneurs in the house and two younger kids, that has been amazingly valuable to us.

Starting point is 01:50:11 I could not agree more. And only in the last six to nine months have I been using, with my girlfriend, a shared calendar just for the two of us. Totally, yeah. And it has been such a stress reliever because she is also an entrepreneur. And if you somehow, at least in my case, delude yourself into thinking that you're going to figure it out when you get there, it's probably going to slip through your fingers. And having it in the calendar just prevents forgetting and then overbooking or fill in the blank with half a dozen things or a dozen or a thousand things that could crowd out that recovery time and that family time and these various self-care practices that are so important for everything else to work smoothly. Just a couple more questions for you and then we can bring this round one to a close. I'm curious, what contemporary CEOs or COOs or C-suite execs do you most admire or say, that's someone who I'd like to,

Starting point is 01:51:26 I could emulate a little bit, or that's someone I could learn from, or that's a good person to watch, et cetera? Yeah. I mean, there's some obvious ones. I think one of the cool parts of being in my position, this is a new thing for me, but one of the cool parts is using my email address. If there's someone interesting, I can actually get in touch with them. That's brand new to me. That's not a flex or some sort of humble brag. That was never the case. I mean, I would send out emails, 100 emails a day sometimes in the early days to connect with different executives and leaders just to pick their brain, just to get to know them better. And most of the time, they never responded. And one of the great things now that I really do not take for granted, I'm really fortunate to have, is that I usually get a reply back, which is so damn cool.

Starting point is 01:52:12 And so I've thought a lot about that. The truth is, a lot of the people that I admire, I admire from afar, like Bob Iger. I've never met Bob Iger. I think he's incredible. Or Phil Knight, I think these are incredible humans. But there are some companies that I think are just run by people that I really like, I really think are doing it for all the right reasons. A lot of them are people that are in the Shopify ecosystem, people we work with. Obviously, we're quite close to the folks at Stripe. You mentioned them earlier, Patrick and John. They're absolutely driven to do incredible things, but also build an incredible company. I think Ben at Pinterest is doing an amazing job as well in that way.

Starting point is 01:52:50 A lot of the people that I really look up to, though, are not necessarily in tech per se. It's people that I just think, you know, one of the people that I really like is a mutual friend. I love talking to Chase Jarvis. I know you, Chase, is a good friend of yours as well. Every time I talk to Chase, I learn something completely new. Or Damon John, who I know is also a mutual friend. I mean, Damon built FUBU. He didn't build a tech company. But every time I talk to him about something unique and different, he tells me a story, an anecdote about how he got his shirt on

Starting point is 01:53:17 LL Cool J for a music video. And it's just from these, what seems like random stories and anecdotes, I'm able to find such great value and such great motivation to think about things in a completely different way. But is there someone in particular that I'm trying to emulate entirely? Not really. I'm trying to, before I had Bailey, our four-year-old daughter, I wanted to talk to people that I really felt were great, great dads and great parents, or someone who was a great spouse before I got married. I'm trying as much as possible to take a bit of an approach that I can have as many mentors as I can handle, and I can pick one thing

Starting point is 01:53:50 from each of them. The interesting part is when you find people that are really, really good at one particular thing, they tend to be fairly spiky, meaning they may have an incredible strength, but also have a whole bunch of weaknesses. And so the model that I'm trying to create now with mentors and advisors and people in my life are to take something special from each particular person and use that in my own day-to-day. I try to be a bit of a generalist as much as possible as opposed to specialize in one thing. I think that there's a little bit of an anti-generalist theme right now, certainly in Silicon Valley, but I don't purport to be well-rounded. But I am trying

Starting point is 01:54:24 to be well-rounded about the I am trying to be well-rounded about the stuff that really matters to me, whether it's leading, whether it's the business, whether it's inspiring the future entrepreneurs of the world, or it's about... I'll give you a quick story. We have this new show that we just launched on Discovery called I Quit. And we have a studio called Shopify Studios with the single mandate to create the most inspiring and authentic content about entrepreneurship in the world. And you'll never hear us mention Shopify on the show because that's not what it's about. It's about entrepreneurship. And before I got on the show, I sat down with Damon and said, walk me through what it's like to be on a show like Shark Tank. And how do you show up?

Starting point is 01:54:59 How do you prepare? And what kind of advice do you give, which is digestible, but also doesn't come off as overly obvious? That's the way that I tend to do things. When there's something that I want to get really, really good at, I'll find the three or four people who may not be the obvious experts in it, but I understand there's an angle to them that I really want to emulate. And then I'll just ask them. And it's pretty cool that I can do that now. That was something that, for those of you listening that do email a hundred people and you're always trying to get more advice and you're always trying to find someone who will give you some of their time or quote unquote, so you can pick their brain. The neat part about doing that is if you send out enough of those, you eventually get a yes.

Starting point is 01:55:37 And that's how I connected with you. And that's how I connected with Seth, who's a big part of my life. And it was just, this was before anyone even heard of Shopify. It's been a really important part of my life. Seth is amazing. Seth Godin for people who are curious. I'll also just want to say as a public service announcement that the success rate with may I take you to coffee and pick your brain is pretty low. I would say it's pretty low. There is a, what you might consider doing is a bunch of free work for somebody and just sending it to them. And that's actually how I've ended up hiring a bunch of people. I'm not saying do that to me, by the way, because I'm not planning on hiring more folks. But if people look up the name Charlie Hone, H-O-E-H-N, and my name, he's written about the experience that we had. He also wrote

Starting point is 01:56:23 about the four-hour body launch. That's cool. People are interested in that. Yeah, one thing that I've always found valuable, especially in the early days of Shopify, was if I want to connect with someone who I knew was incredibly busy and the likelihood of them responding was very, very low, I would figure out what is the thing that is most important to them right then. And in the case of, let's say it's an author, obviously they have a book release coming up. I would figure out how I can be valuable to them. So asking someone, I live in, name some random city,

Starting point is 01:56:49 I want to host a book reading or a chapter reading in my community, and I'll buy 30 books or 50 books. Even if it's not 3,000 books, I find that if you can add some value to something that is so damn important to them right then and there, and with social media, it's easy to figure out who cares about what at what time, man, is that an effective way to spend some time. Yeah, totally. And there's a book called The Third Door I would recommend people check out as well, which has some very funny stories and very effective advice in it, which is about taking the path less traveled when it comes to contacts of that type. Harley, let me ask you, because we're talking about these various leaders, are there any biographies that you,

Starting point is 01:57:30 I don't know if you read biographies, but are there any biographies that you've read and found particularly impactful or influential? Yeah, I'm not sure it's a biography, but one of the best books I've read, I read it a couple of years ago, is Shoe Dog. And I'm not sure if you, have you read Shoe Dog? I have it sitting.

Starting point is 01:57:45 I was sent a copy, a hardcover. I like using Kindle because I take notes a lot or highlights, but I have not read it yet. It's been recommended many times. It is awesome. It's awesome for anyone who's building a company, anyone who's an entrepreneur, or frankly, anyone who's just interested in the idea of ambition.

Starting point is 01:58:02 One of the reasons that I have fallen in love with entrepreneurship and one of the reasons that I have fallen in love with entrepreneurship and one of the reasons that I've dedicated my life to creating more entrepreneurs with Shopify as the vehicle to do so is because I'm fascinated with ambition. I'm fascinated with how people find ambition, keep ambition, increase ambition, and unfortunately sometimes lose ambition. And the story of Shoe Dog and how Phil Knight was so determined. I think it's such an amazing story. And the cool part about it is, I think because Phil is where he is right now and has really nothing to prove to anyone anymore, he was able to be incredibly candid. One of the problems I find

Starting point is 01:58:35 particularly about autobiographies is that you end up seeing the highlight reel of people's lives, especially people that are not at the end of their life or close to the end of their life, where they feel like they still have to flex a little bit. They still have to kind of show off about how great they are. What I love about Shoe Dog is there's this incredible modesty and humbleness about the story, which is this was not pretty. And there were like 12 different opportunities for this whole Nike thing to fall apart. And he goes into the details and tells the stories that, I don't know, I found it to be so fascinating. It's a great book. And you can get through it in like five days if you're interested in it, because it's just, you can't put it down. But that's probably

Starting point is 01:59:11 the best one that I've read recently on that topic. I have to read it, and I'll tell you why, which is not a reason that most people would probably cite. And that is that it was written, we could say co-written, but in reality written by one of my favorite authors whose name people will not recognize, and that is J.R. Moringer. So he is the collaborator, so to speak, who wrote Phil Knight's memoir, Shoe Dog. And for people who want to look him up, you can find him on Wikipedia, J.R. Moringer, M-O-E-H-R-I-N-G-E-R, John Joseph, J.R. Moringer. And I came to know him because even as a non-tennis player, I read Open, which is the autobiography of- Andre Agassi, yeah. Andre Agassi, and it blew my mind. It was so good. So engrossing.

Starting point is 02:00:05 You're the third person to recommend that to me. I've actually, I love tennis. I play tennis, but I have not read that. I'm actually gonna write that down too. So now you know it was in effect written by the same person. That's cool. And for that reason alone, I believe that he did. So J.R. Moringer won the Pulitzer Prize for newspaper feature writing in 2000 also. He's a hell of a writer. If I could collaborate with anyone on that side of things, he's at the very, very top of the list. He's so good. Just incredibly, incredibly, not just gifted, but talented in a way that you know, in a fashion that you know is the output of hundreds of thousands

Starting point is 02:00:47 of hours of refinement and practice, if that makes sense. That's cool. Shoe Dog, it's on the list. We'll swap since I've read Open, but I've not read Shoe Dog. Harley, is there anything else that you would like to say? Any closing comments, anything at all that you would like to add before we wrap up for this round one? Probably the full circle comment is that you and I are sitting here sort of midway through the year, a little past that, 2020. One of the things that we talked about mentorship on this in the last hour or so, we've talked about people in our lives that have helped us. And certainly we've talked a lot about entrepreneurship. But one of the biggest things for us in our story is having not really mentors, not necessarily advisors, but people along for the ride that are our fans, our supporters,

Starting point is 02:01:37 our catalysts for those days that are challenging. And I remember this particular moment. We were, it was, it was 2015. It was May 2015. We were at the New York Stock Exchange. We were about to take the company public. And I remember looking down and our families were there and you were there as well at the Stock Exchange. And I remember thinking, what an incredible journey it's been, not just for Shopify, but also to have people like you, Tim, in our lives, helping to support us, helping to lift us up when we thought things were a little bit tough and we weren't necessarily sure what direction to go into. I don't know if there's a term for that. Maybe it's just friend,

Starting point is 02:02:15 maybe it's just supporter. But for those listening, you find these people throughout your own journeys, whether personal or professional, that in some ways will change the trajectory of where you're going, that there may not be a term for it. It may not be obvious where you're going to meet them, like a green room at some tech conference, like RailsConf in your case. But these are the people in the story that are super valuable to have. And I want to say, just for a moment of gushiness or of emotion for a second that it's been an incredible honor and privilege to have you as one of our supporters the entire time, and certainly in the last decade or so, Tim. It's been amazing for us. And anyone out there,

Starting point is 02:02:54 find your group of supporters however you can. It changes everything. It allows you to and enables you to do things that you couldn't otherwise do, whether it's, I'm going to give away $10,000 for a competition. And that supporter says, no, that's stupid. Give away $100,000. They push you to be better. They see a better version of yourself than you see. And I think those are the people that they help make magic. And you certainly have been that for us. And I'm very grateful for that. Thank you so much, Harley. I wish you could see my my smile right now i've i've had such an incredible journey with you and toby and the gang and i view you as a brother i have a lot of love for you and your family which i hope is super clear and has been super clear and i view you as a

Starting point is 02:03:44 companion on the path that's a good i like that And I view you as a companion on the path. I like that term. That's a good one. Companion on the path. That's a nice one. That's how I look at it. And that companionship and camaraderie is rare. It is rare. And not everyone you spend a lot of time with, not everyone you know for a long time will fit that description necessarily, at least with the sentiment with which I intend it. But those people, those companions, in many ways, they are the difference makers. They are the ones that, it's not even those that raise the bar for you, although they certainly play that role too. But we have a few people, not very many, but we have a few people who have been these companions

Starting point is 02:04:18 on our journey with us. And I'm not sure we'd be here without those companions. So I don't know how you're going to find those companions. I'm not suggesting that'd be here without those companions. So I don't know how you're going to find those companions. I'm not suggesting that you show up at tech conferences and go to the green room and try to find them. But I am suggesting that when you do find them, that you marinate that relationship, that you work on it, that you continuously leverage and connect with them to say, hey, I'm thinking about this other thing. I mean, like I said, as early as this morning, I pinged you on something totally different

Starting point is 02:04:45 about some development thing we're doing at Shopify on the leadership side and got your advice. Use that stuff because I think as much as I get value from it, at least from my perspective, you seem to really enjoy also providing that context and that advice. And it's just this amazing thing that you can find. And you don't hear about these stories very much

Starting point is 02:05:03 because everyone wants to, frankly, pattern match of, oh, that's a mentor. Oh, that's an advisor. That's a board member. That's a friend. But there's this other thing, which is a hybrid of all those things, that is so freaking powerful. Yeah, I couldn't agree more. And I also want to really emphasize something for people who are listening to this conversation. And that is the expression, nice guys finish last is not a truism. It is absolutely not required that you become a ruthless predator to win in the game of business and certainly in the game of life that backfires more often than not. And I really view you, Toby, and others as exemplars of the opposite, which is leading with a kindness. And of course, you're going to be effective competitors.

Starting point is 02:05:58 I'm not trying to imply that you're going to let people steamroll you in any capacity because you guys are very good at short and long-term planning. But what really sticks out to me that may not be obvious from the conversation is that you guys are incredibly generous in spirit. So you have helped many, many, many, many, many people. You've reached out and offered to help many, many, many, many people without any expectation of a payback, without any tit-for-tat expectation. Does that make sense? Totally. It does. And actually, because we are playing the long game, we want Shopify to be a 100-year company, and we ourselves want to be doing this for a very, very long time. And if you use a lens of a very long-term perspective, whether it's 100

Starting point is 02:06:42 years or 50 years, you begin to reinterpret and reevaluate how you engage with people. You begin to think about things in totally different terms. Even if I'm not going to get an immediate ROI next year, who cares? If I can help someone now who eventually may or may not want to help me back later on, that's good enough. But I absolutely agree with you. This connotation or this idea that you have to doggy dog is the way to win. I don't think that's the case. In fact, I would actually say entrepreneurship is the opposite of that. The cool part about entrepreneurship is the more entrepreneurs that you help, the more people that want to help you. It creates this incredible virtuous cycle. And that's where things get really, really, that's the flywheel. That's where stuff gets really good. Yeah, absolutely. And people can check out Finite and Infinite Games by Kars as also a good meditation on a lot of this stuff. Harley, always so much fun. This was at the very least a good excuse just to catch up and jam and talk for a couple of hours. And people can find you on Twitter at Harley F, Instagram at Harley, website harleyf.com, obviously shopify.com. And we'll link to the

Starting point is 02:07:53 build a business and past videos of the trip to Fiji and Gatsby Castle and all this craziness. Oh yeah, I forgot about Gatsby. Yeah, that was a fun one. Yeah, which people will get a real kick out of. That's really cool. Timbo, thank you for this. I really enjoyed catching up as well. And hopefully for your listeners, they got some value from this, but this was really fun. Absolutely. And I hope we are hanging out 50 years hence. I'll keep eating my veggies and fasting on occasion to try to keep me standing for that long, but it's really fun to have companions on the path. So thank you for being

Starting point is 02:08:25 one. Thanks, Tim. And to everybody listening, we will have show notes, as always, links to everything that we have discussed at tim.blog forward slash podcast. Just search Harley and it will pop right up. And until next time, thank you for listening. Just a few important disclaimers. I own stock in Shopify. I became an advisor to Shopify way back in the day when they had something like 10 or 12, certainly fewer than 20 employees. I was not compensated in any way to have Shopify represented on this program or to talk about my reasons for investing in Shopify. Of course, I am a big fan. I may benefit financially if Shopify stock goes up in value, but I'm not

Starting point is 02:09:05 an investment advisor. All opinions are mine alone. There are risks involved in placing an investment in any company. None of the information presented today is intended to form the basis of any offer recommendation or have any regard to the investment objectives, financial situation, or needs of any specific person. I think that pretty much covers it. So you got it. All right. Thanks for listening, folks. Hey, guys. This is Tim again. Just a few more things before you take off.

Starting point is 02:09:32 Number one, this is Five Bullet Friday. Do you want to get a short email from me? Would you enjoy getting a short email from me every Friday that provides a little morsel of fun for the weekend? And Five Bullet Friday is a very short email where I share the coolest things I've found or that I've been pondering over the week. That could include favorite new albums that I've discovered. It could include gizmos and gadgets and all sorts of weird shit that I've somehow dug up in the world of the esoteric as I do. It could include favorite articles that I've read and that I've shared with my close friends,

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Starting point is 02:11:48 computer science background to do that, which scares the hell out of me. So if you don't want to be a victim of that, you can use ExpressVPN. Or if you're traveling and need to access something that's only available in another country, well, lickety split, ExpressVPN has you covered. ExpressVPN is useful not only for entrepreneurs and remote workers and travelers like yours truly, but really for anyone who wants protection from being snooped on or having their personal data stolen. You just use the internet like you normally would, but with ExpressVPN encrypting all of your network traffic to safeguard your data. So check it out. Visit my special link at expressvpn.com slash Tim, and you'll get an extra three months

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The Tim Ferriss Show - #486: Harley Finkelstein — Tactics and Strategies from Shopify, The Future of Retail, and More

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The Tim Ferriss Show - #486: Harley Finkelstein — Tactics and Strategies from Shopify, The Future of Retail, and More

There aren't comments yet for this episode. Click on any sentence in the transcript to leave a comment.