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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. My guest today is Harley Finkelstein on Twitter, 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 adviser 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. And in 2016, he 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 Harley F, Instagram 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 gives me an excuse to do a deep dive and interrogate in a way that would just be totally abnormal and maybe sociopathic over the dinner table. And I thought we would start with describing or explaining what Shopify is for those who may not know.
Yeah, it's interesting. I mean, Shopify has obviously grown considerably over the last couple 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 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 idea 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 really, really big businesses. The Allbirds of the world or the Bombas of the world or the Gymsharks of the world or the Fashion Novas, 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 mention 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. And in terms of the company 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.
All right. So we're going to stay on the present tense for a little bit and then we're going to zoom past tense. Present tense or I suppose this encapsulates any period of time really, but 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. 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 from who had 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 just thought were full of platitudes and full of things that I just didn't find very wise. Whereas I found High Output Management to be by far one of the greatest books. And then actually I think Ben Horowitz's book The Hard Thing About Hard Things is almost like the modern iteration of High Output 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 and I know that you know about is Taleb's book Antifragile. 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 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 Antifragile is it talks about obviously the two main systems being robustness and fragility. But then Taleb introduces this third system of course which is antifragile 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 in right now that you can take two people in the same circumstances and one just resists 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 is I'm actually reading, this is shocking, but I'm reading my first fiction book ever. And I've never read a fiction book in my whole life. I just, I haven't, 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 about an interesting true story. And I'm actually reading The Alchemist right now. And I know and it's a 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. 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 a hundred copies of The 4-Hour Workweek. And I'm not saying that to flatter you and I already friends. I don't need to flatter you. 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 I knew that if we encouraged 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.
Well, you've alluded to something we will spend time on which is the current state of affairs and the future of retail, right? Because in some ways it seems like 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. 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, something billion depending on the day. I think it's around 120, 130 billion.
Okay. And when we first met, how many employees were there and what was the market cap, so to speak?
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.
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, 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 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, I think 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. 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 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 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 as they grow and especially historically if you study, you know, if you study founders going back, you know, hundred 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 do that every single person particular on the leadership team has to re-qualify for their job every single year and that is difficult in year 1 and year 2. 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 re-qualifying 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, you know, we're the same folks who started 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.
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, but for the most part, building a company outside of, 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 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 will 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 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 Rhyr, is that his name?
Wow. You've done your research. Jesus.
I have got a full dossier. I've got a full dossier. So, who is Philip Rhyr and why is he relevant?
Yeah. So, I was born in Montreal in Canada. Lived here till I was 13. When I was 13, there was a referendum in Canada and 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?
Absolutely. 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 feels European almost, but it's in Canada, which is a wonderful country, but it's cold as hell. And Februaries 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 already. And so they just decided, let's go somewhere hot. And so yeah, moved down in, this is probably 1996, moved down to South Florida. And then after in 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 is a great school and it was 1,800 bucks a year. And so my parents are like, 'You got to go to McGill.' Get to McGill in September 2001. And you know, 11 days later, 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 overleveraged for the most part and he was doing things he probably shouldn't have been doing. And I got it. 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. You can't, you know, we just, 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 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 two 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 lots and lots of bar mitzvah, like 300 bar mitzvah as you know. We talked about that a lot. And so I DJed, I was working at a travel agency trying to go to McGill and it just wasn't working. There was no way for me to make enough money that I didn't, 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 at, you know, in the bookstore, the stuff you get in your orientation bag that says, you know, faculty of science or faculty of arts or whatever it is, hey, if you want to start something, that might be an interesting thing to start.' And Montreal has historically had this incredible, they sort of call it the schmata business, but it's basically the apparel industry. You have companies like Buffalo and American Apparel and Pariso 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. Let me just...
What was the colloquial name for it?
Schmata business, which is, yeah, it's Yiddish. Yeah, it's a Yiddish term that basically means clothing. 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 apparel industry, the schmata business was that it had a low barrier 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 also a student there, how could they not give me the order? And I spent the next, you know, two to four years, I guess two years until it sort of took off and then 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 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 Rhyr 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 about 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 6 months prior to getting married, there were three people that just seemed to have the greatest relationship to their spouse. 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 Rhyr, who was just a friend of my parents, who it turns out wasn't even that close to my parents, but he just 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 and he would explain it in just this very simplistic digestible way and I just, throughout my undergrad years I called Phil towards the end of my undergrad and said okay I had 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 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 the 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 at a 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.
Kind of. Yeah. Like that 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 decidendi, the one line that matters in any 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 Rhyr 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 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 Sacca, 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.
I, you've studied Socrates and some of his work. So I assume there's origins there. But law school uses the Socratic method which at least the iteration of it in the law school that I went to was it would ask, 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 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 that and the second thing is writing. In Montreal, I went to a sort of a Jewish private school. And then in the States, I went to a very large public high school. And it was a really good public high school. But I, you know, 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. 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 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 sell 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, you know, 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.
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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. I'm actually in luck with this conversation because about a week and a half ago I read Socrates in 90 Minutes 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 elenchus. I don't know if that is from Latin or elsewhere. Literally refutation or scrutiny whereby a series of questions clarifies a more precise statement of a vague belief. Logical consequences of that 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 you 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, because most people come into battle, so to speak, if we're talking about debates, with very unclear assumptions. 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.
Totally does. And actually, it's the best way to defeat them because then actually, it's basically unforced errors 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. 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. 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 you know X versus Y here fundamentally the professor wants to get to the point where we can have a discussion about you know city land. And so how do I go from the overview of the case to a discussion about 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 carefully about what the lesson was. Not all professors are at the same level. Some are bad professors, frankly, at every school. You know, not everyone's going to be the greatest professor of law at every single school. And so I had figured out that this is where the professor wants to get to. Let me simply reverse engineer the line of questioning 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 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 in like the 1920s. Yeah, 1923.
Very small, very short book.
I think it's like 60 pages or something.
43 pages. I mean, it's that's 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. 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. 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, which is effectively like debate. It's 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. And I loved 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. 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. 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, right? 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. So or toning, right, in the realm of exercise, that does not have any physiological meaning whatsoever. 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, 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 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, right? And if you need something to be defensible or to withstand scrutiny of the court, you got to ferret that out right away.
Yeah. Interesting. 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 his 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 Number Four by John McPhee on the writing process which if you really are a nerd and want to study structuring how you structure a piece 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. And from a sort of divide the world and conquer perspective, I look after it's more the business side of Shopify, the commercial side of the business. But actually, we talked a bit about earlier about this idea of re-qualifying for your job. Part of that annual re-qualification 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 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 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 like 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 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 let's go way back. 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 Rhyr. 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. It's kind of between Montreal and Toronto which you know two of the major cities in Canada. So I arrived here and starting 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, 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 sort of business incubator type organizations. One was called Invest Ottawa. And I just asked around where the entrepreneurs 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.
I guess. Yeah. I mean, it's far less sophisticated than that. And certainly far less glamorous, but I just 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 the people was, you know, it was Luke LeClerc, created Travel Pod, who then went and built Messenger Kids at Facebook. He actually just recently joined Shopify. There was Sam Zade from Getaround, which is a San Francisco startup. Idan Senkut who did Fluid Surveys, he's now doing Felicis. 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 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 Snow Devil 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 enterprisey 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. 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, you know, software product genius. And I say that, you know him so you know that that's completely accurate.
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 to sell these snowboards. And he had a really good snowboard business, Snow Devil. It was a really cool business. But eventually, as the summer came and people were 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 Snow Devil 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. You know, like the snowboards were a good idea, but he really believed that 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 little store called Smoofer.
What the hell is Smoofer?
It was this sort of the time like Zappos and Google and like a lot of the company names of that vintage were kind of made-up words. Sort of like the next iteration was the Ephy vintage and the next iteration was the io vintage. But this vintage when I started was 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 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. He, you know us both really well. He and I are polar opposites in most ways. He is cerebral. I am incredibly extroverted. He's a little bit less extroverted. I know you've referred to me as our extrovert.