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At this altitude I can run flat out for a half mile before my hands start shaking. Can I ask you a personal question? I would like to be. Cybernetic organisms living tissue over the embryos go to Paris, so. Hello, boys and girls, ladies and germs, this is Tim Ferriss. Welcome to another episode of the Tim Ferris 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 Finklestein on Twitter at Harley F.. Harley is an entrepreneur, lawyer and the chief operating officer that's CEO of Shopify. He founded his first company at age 17 while a student at McGill Harley is an advisor to Felice's Ventures and he is one of the Dragons on CBC's Next Gen Den. In twenty seventeen, he received the Canadian Angel Investor of the Year award and Canada's Top 40 under 40 award. And in twenty sixteen he was inducted into the Order of Ottawa.

From 2014 to 2017, Harley was on the board of the sea one hundred and from twenty seventeen to twenty twenty. 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. It's him. 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 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 is obviously grown considerably over the last couple of years, certainly post IPO in twenty. Fifteen 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. Mm hmm.

And if we wanted to take some numbers to that, any kind of stats or numbers, what can you share that would give people maybe an info graphic 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 there, commerce on Shopify. The majority of those brands would self identify small businesses and some of them that we're small growing to be really, really big businesses. The Albats of the world or the bomb business of the world, or the Jim shirks of the world of the fashion novas. But for the most part, we've 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 shop, if I 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 and help level the playing field and 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 way you look or publicly traded company. Our market cap is about one hundred billion, which still sounds unbelievable to say. And something is kind of amazing. We have about six thousand employees across seventeen offices all over the world and in Q2 of this year. So this past quarter we're talking twenty twenty. Our merchants sold about 30 billion dollars 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 and your business journey with Shopify end 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 up in management and which is the Andy Grove book from who obviously built Intel.

And it did an amazing job. And one of the reasons that it was recommended to me was it seemed to cut through a lot of the books 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 do go to business school and the business books that that they naturally give out.

I just 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 by far one of the greatest books in then. Actually, I think Ben Horowitz's book Hard Things About Hard Things. It's almost like the modern. Iteration of High at 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're that you know about is Tellabs 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 in 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 for and anticipating when normalcy will return.

But then there's this whole other cohort of people and a whole 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 to Leyb introduces the 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 to 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 is I'm actually reading this is shocking, but I'm reading my first fiction book ever in my whole life. I just 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 a business book or just generally fascinating book about an interesting, true story. And I'm actually reading The Alchemist right now. And I know and it's a book. 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 it the most, it's probably the book. But in the early days of Shopify, I probably gave out one hundred copies of the four hour work week and I say not to flatter you and I 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 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 that was an important book in my life, but also in Shopify as well.

You've alluded to something we will spend time on, which is the current state of affairs and the future of retail, because in some ways it seems like many trends that may have 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 No.

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 six thousand and grow over 6000 employees and market cap is, I don't know, one hundred and something billion depending on the day. I think it's around 120, 130 billion.

OK, and when we first met, how many employees were there and what was the market cap. So 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 there had just raised or about to raise our series, just about to raise. I think we were just about to raise our series. And I think our series was I mean, it was sub 50 million.

I 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 you 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 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. I really feel that way. And I just want to congratulate you. It's been it's been awesome to watch in the very literal sense of awesome. So.

Well, I appreciate you saying that. It's 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 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, the 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 a Sharpei 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, has made for a much more meaningful journey when you deal with people and you grow together. Now, obviously, the flipside of that is in order to do that, every single person particular on the on the leadership team has to requalify for their job every single year. And that is difficult in year one. In year two, it becomes incredibly difficult in year 10, year 11 and you're 15, where the stakes, the challenges, the opportunities are all so much bigger.

But I think for the most part, we've we've all focused on qualifying for a job and also keeping our I don't want to say modesty, but just being grounded in this whole thing and realizing that there is like we're the same folks who started who were there at the beginning. And I don't know in that way. It's 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 want to be nice because we're Canadian. And I can tell you that 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 and you do feel that from time to time. But for the most part, building a company outside a tech company outside of Silicon Valley, I think it's 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 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.

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 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 Phillip Rimer.

Is that his name? Well, you've done your research. Jesus, I have got I've got a full dossier. I've got a full dossier. So who who is Phillip Rymer and why is why is he relevant?

Yeah. So I was born in Montreal, in Canada, Lipshutz. I was thirteen when I was thirteen. There was a referendum in Canada, in Quebec where I lived, where Quebec as a province want 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. Do for a second. Sure, 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 it's like it feels European almost. But it's in Canada, which is a wonderful country, but it's cold as hell. And Februaries and Montreal are notoriously bad because it gets dark very, very early. The number of sunlight hours is very small. And it's not just shabby. 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 it was going to be somewhere warm.

And so it was a combination of staying on the East Coast 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 we have moved down. And this is 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 U.S. 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 eighteen hundred dollars a year. And there was just I loved Montreal. McGill is a great school and I was 18 bucks a year. And so my parents are like, you got to go to McGill, get some Egill in September. Twenty one. And you know, eleven days later, September eleventh happens, stock market crashes, things get really, really bad.

And my parents lose everything. I mean, we lost our house, we lost everything. We'd never a penny to our name wise. That's because of the equity markets.

Yeah, my, my, my my dad was just over leveraged for the most part, and he was doing things he probably shouldn't have been doing. And and he just he just did stuff that 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 can't we just just come back down here and and we'll figure it all out. And I was 17 years old when I started, maybe a bit younger than my peers. I loved Montreal. I love 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 can also try, if I can, to help the family out as well.

I have too much younger sister, so I thought, OK, 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 deejay since I was a kid. So I was a DJ parties and events and weddings and anything that that and Bartletts and lots and lots of our mixes of like three hundred bar mitzvahs. As you know, we've talked about that a lot.

And I decided 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 twenty five thousand dollars every semester on promotional T-shirts.

The stuff that you see at 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 incredible sort of they call the shots of business, but it's basically apparel industry. You have companies like Buffalo and American Apparel and Paris. Suko 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, OK, cool. Well, let me just ask, what was the colloquial name for it?

Schmetzer business, which which is Yiddish? Yeah. Yeah. It's a Yiddish term that basically means clothing. And and part of it was Montreal was an absolute immigrant town. My family came to Montreal from Hungary in fifty six, but it's an immigrant city. And so the neat part about the apparel industry, the Schmetzer business, was that it had a low barrier to entry. So you can start a business without with the 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. So it was Canada. So it worked to some extent. It worked that it allowed me to pay my tuition.

It allowed me to help my mom and and my 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 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. And I called them and said, hey, tell me about being a great spouse and did the same thing for being a dad. I did the same thing and 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 just 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. And he would explain 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, OK, 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 that was it. And his his proposal or his idea was, have you thought about going to law school and was like, no, I don't want to be a lawyer. Why in heck would I go to law school anyways? He 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 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 is kind of.

Yeah, like he would teach you how to write, how to think critically, how to debate, how to argue. It would teach you how to read four thousand pages and pick out the one line. They call it the the ratio. That's identi. The one line that matters in a court case, you'd be able to pick that out out of four thousand 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 Rymer, and I got in the city of Ottawa and I moved here in twenty five.

Now you, I suppose, hinted at what you gained from your law education. What would you say? You mentioned a few things that that he speculated you would learn were the most valuable things you learned. Those were they. Other capabilities were a 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 Krosoczka, both billionaires who have been on the podcast among them.

That is one common thread that shows up now and again. What were the most valuable things in retrospect that you gained from that experience?

Are you familiar with the Socratic method? Have you heard that term? Do you have some familiar with the Socratic method? But if you could explain it, if that's going to be part of the you've studied Socrates and some of his work. So I assume there's those 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 they would ask the professor at the front of the class, would ask a question and would randomly collect 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 so is such a strange take away 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 of assigned work because by the nature of law school, the 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 twelve hundred pages and I can read that in twenty four 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 stand 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 is one of the most valuable things. So I will say that in the second thing is writing in Montreal, I went to sort of a Jewish private school in the States.

I went to a very large public high school and there was a really good public high school. But I got school. I went to McGill for undergrad, and I never really learned how to write really well. And I only realized that in law school I only rose 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 pedagogy. It was super practical that it taught me how to very quickly reply and quickly think on my feet or 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. Then I want to 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.

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That's LinkedIn. Dotcom tagged him to get fifty dollars 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 twelve hundred 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, which is part of a series of books that are 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 here's what it says. The Socratic dialogues are particular form of dialectic, known as the method of in here. You can probably correct pronunciation, but a Linkous, Ellie and us, 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 statement are explored in 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 twelve hundred pages, what 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 and 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, 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 it's unforced errors as opposed to forcing them to 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. Finklestein, 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. OK, well, why is this controversial? Well, the reason is the property that they fell on wasn't actually the homeowner's property was city property. Well, OK. 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, OK, this case, you know, 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 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 you do have not everyone got to be the greatest professor of law in every single school.

And so I 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. Mm hmm.

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.

There's a there's a book called The Elements of Style. I think that's what the book is called here. Yes, exactly. That's right. Certainly. 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, I did.

Twenty three small. Very of it's like 60 pages or something from forty three pages, forty three pages. I mean, it's nineteen eighteen. Wow. Yeah. So if I didn't go to law school, but I want to replicate some of those learning 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 in 2005. YouTube is 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, 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 this part of the book that they loved writing the most.

And that tends to be not always, but that tends to be the the major takeaway. And so if there's 12 chapters, usually the writer, the author in this case, a legal text books, the legal scholar on the topic, will very quickly get to forget all of 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 podcast and great interviews and and just really high quality conversation.

And probably a third thing is, would you you'd sort of said this earlier, but we didn't moot court Mozote, which is effectively like debate. It's your pretending like you're in court. There's a judge, there's a jury. There's you know, there's 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 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 SC. Ah, it's a classics bit longer. Three hundred 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. Yes. No, no, totally. That's here to support free.

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. So or toning in the realm of exercise like that, that does not have any physiological meaning whatsoever. And to help clean up the clutter 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 to 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.

Right. And if you need something to be defensible or to withstand scrutiny of the court, you've got to ferret that shit out right away. Yeah, and it's super, super helpful.

It's funny. I'm just reading 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 eighty five pages, much shorter than this one.

I'll tell you right now that every aspiring writer should read 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. Yeah.

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 Paltos been on the podcast. I want to make one fiction recommendation to you, and that is done by Frank Herbert.

And I think it will go right up there next to the Horowitz book and also to Andy Grove in terms of maybe not management, but leadership books. I think I think you'll be very impressed with it. Let's come back to your job, what 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 earlier about this idea of qualifying 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, the early days of any company, and actually it's super important as the company ages, but certainly in the early days where you don't have six thousand people is to figure out one of 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 a Shopify for more than a decade and I'm thirty five.

So like almost a third of my life, I've spent in a shop, 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 story tell 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 but 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 Goose you, but that's truly how I spend my time.

That's a great adjective. I'm going to use Mother Goose you in the future. So storytelling storytelling is important. Persuading is important. That's another skill you are able to practice in law school and that applies in the building 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 two thousand five. I moved to Ottawa on the advice of of this guy, Phil Rimer. And when I got here, I did not know a soul. I had never even been to Ottawa before. Ottawa was the capital of Canada. It's kind of between Montreal and Toronto, which were two or two of the major cities in Canada.

So I arrive here and starting law school and I have no friends, family here. One of the things that was really valuable to me in Montreal when I was 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 my for me to find my 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 Auto Up. 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 the Club Bridgehead. And it's like the Parisian, I guess.

Yeah. I mean, it's it's far less sophisticated than that and certainly far less glamorous.

But 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 those people was it was Luke Levak created Travel Pod, who then went and built messenger kids at Facebook. He actually just recently joined Shopify. It was Sam Zade from Getaround, which is a San Francisco startup. IDN Mizrahi did fluid surveys. He's now doing fellow and it was Toby and Toby was an immigrant to Canada.

He moved here a couple years prior to that from Germany. He moved here because a few and he met a girl who's now his wife, and he moved to to Canada. And he initially, because he couldn't work, he couldn't get a job. Someone told him that without you know, without having your social insurance number in Canada, you couldn't get a job, but you could start a business. And 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, just some sort of enterprise 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 ecommerce. 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 own 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. 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 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 stoneware business. So 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 he had built for Snowville 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, like the snowbirds were a good idea.

But he really believed the software side of it was a great idea. And he created a Shopify. And the 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 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 in my in my classes in law school and I became store one hundred thirty six, built a little store called Spoofer Escoffier.

Yeah, that's true. What the hell is this thing.

Thing. It was, it was, it was, it was in the.

This was 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. Right. Sort of like the next iteration was the Afie vintage and the next iteration was the IO vintage. And but this vintage when I started was it was just a lot about finding random words and the early dot coms were available.

So I started this filter business called Spoofer. 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 you and and just started selling these t shirts on Shopify. And more importantly or equally as important, the same time, I really started to develop this wonderful friendship with Toby. He, you know, was both really well, he is him 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 prefer to me or extrovert, a little bit less extroverted than me.

The way that he sees the world is very different, the way I see the world. And in many ways, we just 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 sitting up spoofer, 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 in the way of the fees.

And I think eventually he got so annoyed that he just made my store completely free. And years later, of course, when I decide to join, he would say that, you know, I was just kind of this monster and he made me his monster as opposed to sort of be on the outside. But we became really good friends. And we throughout law school and business school, we just I was a Shopify merchant. I fell in love with his shop.

If I thought how incredibly democratizing it is it that me some twenty two 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 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 Walmart at 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. The software was just magic to me. Let me hit pause for a quick second.

We'll 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 license or who has the rights. 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 on to it. And but then you have these things called sub licenses and what was needed. But 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. 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 no one really wanted the license for it, and my thinking at the time was that one of the licenses, one of the shirts did really well was when the Batman Dark Knight movie first came out.

So I think it's around twenty six thousand seven 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, was getting a lot of attention. And I knew I was only able to afford to have that in particular cities that 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 keyword in that particular geography because no one else was doing it at the time. And Google AdWords is 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 hundred thousand 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 an hour, two years or so before some big company came and bought all of these licenses. And I was able to sell it anyway. But that's that's kind of how I did it.

And actually, in hindsight, I 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 recognized 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 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? Like, what was the conversation or the email with?

What was what was the what was the actual process?

So now you're now you're winding me up. So after after after 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 ten month program. You have to work at a big 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 ten months, you write the bar exam and you get called to the bar in the near 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 lifetime, 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 deejaying or selling T-shirts or it was sort of, you know, hustling through school, plus also having an online store, my relationship with work was always that of one great passion, but also great love and great fun.

And I just I loved working. I just I found it very satisfying and I like the challenges of it. I'd like to satisfy 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 sort of big companies like that or industries like that, they're 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 want 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 students do. And because I was a first year lawyer, because I didn't 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. I was 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, month five or six of work in this law firm, I call Toby and said, I really want to join you.

And at the time it was 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, you know, Toby, Daniel and Cody are three of the most brilliant humans I've ever met. They're certainly on the technology side, in the R&D side. And I felt I can come in sort of help on the business side. And that was that first call.

And I think after I had to meet our original angel investor 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 and I think after, you know, 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 shopping as a customer shopping wise, in early 2010, I joined the company and I think my original title was VP Biz Dev and Legal Counsel or General Counsel or something like that.

And and that was those about 11 years ago. Well, it 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 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 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 or any particular any particular items or memories stick out to you?

You know, we decided to raise our series a I guess around midday around the summer of 2010. We decided that it was time for us to raise our series. And that interest or that appetite to 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 the company how to spend a dollar here to make a dollar eighty on the other side.

And so, therefore, the more dollars we had on the left side, the more dollars 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 who we are already working with indirectly, whose counsel are already taking without even sort of 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 SACE Businesses and the White Paper. It was it was great. It was 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 ARPA and customer lifetime value. And it provide us with a set of calculations and formulas that allow us to know whether or not our business was healthy or not.

And just a quick pause just for acronyms for those who might not know. So SAS software as a service is a service, our average revenue per user, is that right?

I get there and then customer lifetime value is as LTV our customer, our customer lifetime value LTV and. It was it was instructive, it was it was valuable, so funny enough, we were already kind of working with Bessemer, even though we 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 our business at a very deep, sophisticated level. And so we knew that Bessemer, we wanted them around and they ended up leading the series. But there were two others that a bunch of other people had heard we were raising. And we got some inbound interest, which is 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 to I didn't actually know the story until this morning, but at one point in the middle of the fundraiser, in the middle of deciding what the round was going to look like and who were the investors going to be and what the terms of the deal is going to be like. Someone showed up at our door in Ottawa.

We were in this area called the Byford market in Ottawa, right above a restaurant, wasn't a necessary fancy office, but someone showed up and his name was I didn't think it from Felice's 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, you know, cut his teeth as an early employee at Google and had this great reputation.

But I didn't show up. And part of I mean, once you talk to him, you realize how smart this man is and how intelligent he is and how experienced he is.

But just him showing up with such a wonderful him. And I talk about the 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, which I think and hope it did. It was a really good investment for him. And first Mark, also first Mark out of New York also join the same type of dynamic.

They simply should first Mark really just showed up and helped us the second we encountered them. And that was our series. It was a seven million dollar round. I think it was a twenty five billion dollar valuation, maybe twenty five post. And that was our series in 2010.

So IDN for people wondering, is a white guy and last name since it Seun Kuti. So on Twitter is a sinked and he's an investor. Lots of stuff. So you've got Schupp five Fitbit plural site, Rovio, Knowshon and many, many others. Very successful. Very nice guy.

Now so here's a huge story about him. In the early days after he invested, one of the things we needed was we needed some 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 I didn't heard this and immediately connected us with Rovio and so on, if you remember this, but Angry Birds was just a major hit as Angry Birds. Angry Birds was like flying.

And I think it's 2011 or something like that. And the brand, I think they were from Finland, if I'm not mistaken. The brand just blew up like 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. And Shopify IDN connected us directly with Rovio people and within like 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 blow outs in terms of demonstrating the scalability of Shopify.

And that's the investor he is.

I have to wonder what his pitch was to them. I'm pretty sure it wasn't.

They want to see if their software is, you know, I assume it was a lot more of these guys are amazing, the best platform ever. They, of course, they have lots of at scale stores. And so you don't have to worry about them. But what's interesting was I didn't had come to you because of our existing relationship and you had made the intro to us from IDN. And I actually didn't know that until this morning.

It's pretty it's pretty wild. And just to this background context, for people who don't know, Toby and I had met in 2009 at something called a Rales. You mentioned Ruby on rails. And for simplicity, let's just call Rails Comfort Developers Conference. Why I was there was I mean, I think I was largely there is 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 meeting the backstage. Room or a 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 adviser to Shopify. And so from that point forward was along for the ride.

And and you actually gave us one of the best piece of advice as an advisor, kind of remember. You remember this and I'm going to I'm going to butcher the exact quote you gave us. 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, 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 piece of insight, certainly in the early days we ever had received in that came. That was from you. And we're internally grateful for that.

I appreciate you saying that the bill, the 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 Francisco, back and forth, back and forth, past like the bodega on the corner. And having this conversation, the very first conversation about what would later be the bill, the 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 sign ups. 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 Crossing the Chasm? Yes. So fundamentally, if you were asking would 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 general is we 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 of any of us. It just it just there was unknown to them. And so your comment that. Hey, you guys have the right software for anyone who is already decided they want to be an entrepreneur using Shopify as a great idea, but what about people that have not yet made a decision? Because for ninety nine point nine, nine percent of the world, entrepreneurship is out of reach.

If you don't know one 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 in this idea that what if we created a competition as the proverbial kick in the butt to convince folks to try entrepreneurship? And you, Shopify and the store with the highest sales would win ten thousand dollars. And I distinctly remember you saying, yeah, that's bullshit. Ten thousand dollars is nothing.

You got to give out one hundred thousand dollars, which was most certainly more money than we had in our accounts, certainly more money than any of us had and combined. You could have said a billion dollars and it would have been the same thing to us. That's how much a hundred thousand dollars 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 in entrepreneurship and. In the same way, you know, one of the amazing marketing hacks that Nike did, and this is they deserve all the credit in the world for this is 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 and ran track and field.

But they convinced the whole world, if you have a body, you are absolutely. An athlete, and I think what we began to do throughout 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 one hundred thousand dollar prize to the store that that sold the most. 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 got one hundred thousand dollar 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's something like a startup creates their own startup competition. And it was a really meaningful thing for us. And to build a business competition ran 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 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 us both internally and externally as a company that thinks differently about entrepreneurship in retrospect and also at the time the saw the logic behind pushing for the hundred K is there's psychologically a very big difference between five figures, six figure and seven figure, and also for those people who are thinking about how to differentiate themselves in business or otherwise. But let's just look at it in the context of entrepreneurship. If let's just say 50000 dollars puts you in the category of amusing that arbitrarily, but like ten thousand or fifty thousand dollars puts you in the category of business competition.

And there are other business competitions that have done sixty thousand, seventy thousand.

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, 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 that 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 one hundred thousand dollar 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 hundred thousand dollar loss if it's a failure. And if you shoot high, I think it's Larry Page is fond of saying there's something like this. 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 yet The New York Times coverage and you were extremely newsworthy 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 is that what you we didn't realize at the time, you only have to pay it out at the end of the competition. So you don't actually need one hundred thousand dollars 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 and that was that was sort of an interesting rate. Like 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. And you and I talked about competition law before in advance of it. So we actually couldn't necessarily offer it everywhere because of some what they call sort of gaming law. But absolutely, it was bold. It was ballsy.

It was it was an interesting thing that a small company was doing. And we had thirteen hundred contestants sign up or build a business on 2010. And the winner was a company called Datto Case, which made the most beautiful iPad cases and ended up Obama was using one at the time. He was photographed using his dodo case. And they also did some really cool stuff, like they completely rejuvenated the bookbinding industry, which had been effectively shut down in San Francisco.

And they they brought these book binders together and started making iPad cases. But the neat part was the big take away from year one was some of these businesses were growing so big at the hundred thousand dollars or frankly, any amount of money, unless it was something absurd, was not going to be enough of an incentive. And so, as you recall, on year two, we changed the pricing 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 and wanted to kind of help out, and we brought on people like Seth Godin and we brought in people like Gary V. We brought on people like Richard Branson and Tony Robbins and before Leo and Debbie Sterling and and Eisenberg. And we brought these incredible mentors aboard and. Instead of giving him one hundred thousand dollars, we said, hey, the winner is going to spend a week with us and bunch of really interesting people on Richard Branson's private island in Necker and the Beavis.

And I think last year we did it. We had over 10000 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 10, 20 acts. And one of the winners of the last one was Jim Shahak, who as of last week is now a billion dollar brand.

Now, these businesses may have started regardless. And despite all the business competition, I mean, then from Jim Shahak, 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 bringing us that, because our trajectory has been forever changed, because we've built a business.

It's been so much fun and such a pleasure. You know, I'd 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 because we haven't talked about it is that I remember when shop I went public and spending time there in New York, Wall Street 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 steak 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 adviser, blah, blah, blah. 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. To the extent that you can what has happened in the last few months and the future of retail, we're like, what are the things that people are missing? What are some of the sort of 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, for that matter, who is who is handling type 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 and intelligible way. So how would you talk to what's happening, what has happened in the last few months and the future of retail?

Yes, first of all, you said this earlier, but this idea that the year 20, 30 has been pulled into twenty twenty, that's a real thing. And what I mean by that when I say it, is that the retail dynamic would have existed, meaning percentage of total retail that was done online, laggers that have began to digitalize their business from a commerce perspective that is all happening 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 five percent, something like that. And last year, this is these are US numbers. Last year, e-commerce was about 15 percent of total retail. So we've grown about 10 percent in like 10 years. We're now at close to twenty five percent. So since March, the amount of acceleration in shifting total retail to online retail has been has been dramatic.

One is. I'm 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 now, I mentioned in 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 Barneys or 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 the fact that their e-commerce efforts was hurting their offline commerce efforts, which is ridiculous. And you talk to any of the guys at Albats, for example, they couldn't care less if you buy an in-store, online or on on social media.

They just want you to buy their shoes and their online store, maybe a catalog for their offline store or their offline store or maybe 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 to a gym shark earlier in context of build the business. The day that covid hit their base in the UK, they were told the gyms where people workout were going to be closed. They rebranded their homepage as home shark to the gym shark. They immediately changed their content and their distribution and their influencers. And everything about that company changed within twenty four 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 you see restauranteurs that are doing meal kits and they're turning in their their restaurants into wine shops. If you can't go in there, you're seeing grocery stores that historically never even came close to shop if it wasn't a vertical of hours are now setting up shop online, doing the top 12 most popular items and have a beautiful store.

Chappellet has a store on Shopify right now where they're connecting Chappellet consumers with the farmers who are there are their suppliers. They're basically creating a Chappellet farmer's market for consumers on Shopify. So on both sides of the coin, you see totally different stories. And I want to focus on the resilience side because frankly, that's the real story here. The real story is that consumers generally have now decided and this 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 Branson direct to consumer. And so you have this new retail model and it's not necessarily just going to be online or is going offline. The future of retail will likely be retail everywhere.

And it's going to be about consumer preference, which is so different than think of when you were a kid and you wanted something, you wanted a videogame, you would be forced to line up.

On a Saturday morning at some GameStop in the mall at nine o'clock in the morning and the doors open, you ran in to grab the video game and 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, like 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 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 or 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, 150 years. It is a tale of two world. And I 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 gym sharks, the fashion Jova as the bomb bosses, the Tommy John underwear's like these amazing, incredible iconic brands.

But we've seen Heinz ketchup go direct to consumer during the pandemic. We've seen Lindt chocolate, Snickers, Schwinn bicycles. Some of these brands are brands that I have personally been calling for five or ten 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 quo, to an old version of retail. And I just I don't think is going to happen.

Yeah, I don't think it's going to revert to at least what the previous normal would be any time soon. And I remember the night that, you know, I decided to jump back in to bed with you guys. And it was is very specific to a couple of things that happened. A, you guys have been unfairly well, as far as I'm concerned, unfairly punished in when you suspended guidance. And then the second thing that happened is I tried to order coffee filters on Amazon and I'm also 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, right. You'd 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, you know, 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, we're 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 they couldn't contact directly. And I thought, OK, at the very least, this is going to be a 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 at least need a Plan B.

so that there is a Google discoverable a 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 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. But if you look at vertically integrated, but if you look at other shops, that might only represent one layer of the stack, so to speak. Right. Facebook or whoever it might be, their options are pretty limited. I mean, they can build in-house or they can partner with with someone who's who's already built out the infrastructure. And the neat part about that is we actually don't like we don't 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 houses or so do any of these things. The neat part about our positioning is that we simply encourage more people to try their hand in entrepreneurship and to 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 why don't we all are?

I mean, our communities are now becoming far more important because frankly, like I spent one hundred nights on the road in twenty nineteen, I'm going to spend five nights on the road in twenty twenty. My community here in Ottawa has become incredibly 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, that the money that we're using to buy stuff which 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 many, not the few.

Which is why we talk about this idea of like 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.

If it's easy, if it's if it's easy and that's 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 was aware of, but that you have coaches internal at Shopify available to folks. The story I read talks about Cody Forcer. I guess it is so correct and his experience with coaching. But how do you use coaches and how are coaches used at shapefile?

Yeah, so Cody Cody was our original CTO and one of the 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 is 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 coding apologist and Trump.

But since this has come up a couple of times, what does it mean to requalify for a job? You're getting effectively hired each year. A new what is it? Is that metaphorical? It's more of a loose philosophical guidance or is it 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, 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 operating 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 of Shopify is growing at. It has been growing every single year since since I joined.

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 a billion dollar capital business. We have a fulfillment business now. We're cross platform 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 going over 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 CFO, I need to know that I am still the right choice. And this idea of requalified for your job from a philosophical perspective has just been incredibly valuable because it means that if I grow at the same pace of shop, if I still may not necessarily be the right person for next year. So I have to almost outpace Shopify as growth, which puts the onus on me and all of our leaders to grow with 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. 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 an 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 CODI. So take us back to code. And it seems like it seems like coaches are one of the tools in the toolkit for staying ahead or frontrunning.

Yeah, 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 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 these coaches around more often. So we ended up hiring our first coach. His name is Cam and bringing him out full time.

And he really helped coach the exact team and Shopify and then quickly explained.

So I'm going to keep interrupting. It's my job. What is this coach doing? Because there are coaches kind of like teacher, right? There are a million and one different ways to be a teacher, a bad teacher, a mediocre teacher, a good teacher, 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 cert, 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. 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 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 a 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 of 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 camp 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 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 that 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 will have a group coach. They can sort of interview a few of these coach 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 develop with their coach. But by bringing them into the company, it allows them to have a 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 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 the 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 there may be interested in trying coaching what happens in that hour every two weeks. And it could be just personal examples, but any specifics would be super helpful. I like what actually happens.

Is there like 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 that the coaches that I have seen have one of the things that they have done, which I found very valuable, is this is a metaphor. So for me, this is I'll just tell you what a metaphor is, because I think it's valuable for 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 go in the right direction, but that inevitably they will get there on their own. 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 is completely ridiculous. And now I see that. And so I had to work on some of that, some sort of personal issues. I had to work on the fact 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 fifty percent trust battering through their actions.

We we watch them hopefully get to 100 percent, 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. And that's not necessarily something that all coaches use the coach. 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, an hourly basis walking through.

OK, give me some examples of how you've demonstrated more of that sensate type of thinking and less of the method 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 Masad commander, a man that has been so, so helpful.

It also feels like when you do bring them in, 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 do just they 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? 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 what I suck at and please call me out of my oh 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, you know, if I had to distill down one of the things that allowed me to get to where I am at this point with my career and certainly help me lead Shopify coaching is up there in the top three or four things that I've done.

What else would be up there and the others come to mind that are in the the sort of 80, 20 distillation of things that have really moved the needle. The other items come to mind. This is a maybe a personal thing, but even as a kid, I always had anxiety I never had a term for and I never understood exactly what 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 looking for some sort of quick fix that if after ten minutes of meditating I didn't find enlightenment, I thought I was broken. I thought I wasn't working for me. And which sounds absolutely ridiculous, of course. But meditation is also been something that I have committed to or less probably since 2014. So going on six years now, every single morning, it's either ten or 15 minutes to depending how much time I have.

And it is made me I'm by no means you can hear from the tone, 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 spend 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 men like I mean, I know you talk a lot about mindfulness practices and and meditation on the podcast, but I am someone who for years just 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 like badminton, there's curling, of course, not to be forgotten. Are you there because you've got me, 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 consistently?

So it's funny. I had been historically using just inside 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, extroverted ness, I've found that this pandemic has been kind of lonely for me. And I don't mean that in a severe way. Like, you know, 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 Incyte timer just because I kind of just wanted to hear someone 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 mentioned you've talked about Jack Kornfield, Sharon Salzberg, David Gandelman. There's some starting to look at who else?

Sarah Blondin. There's just some amazing guided meditation coaches on inciter. Frankly, I mean, you can probably do it on YouTube as well, and I actually have found that guide, it 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 set. And I always end up on the other side so much better. And so I started with counting breaths from now, trying to do a little more Montera 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 just take it easier on myself around my own version of what a successful set looks like.

And I think today's success will sit for me is really just the ability to sit for 50 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, but it's the consistency and I think blocking out that time that is the prerequisite for almost everything that follows, because by blocking at 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 a compulsion as much as it 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, insomuch as you are not rushing yourself. And that has many downstream effects, even if you're just thinking about your to do list and staring at the ceiling is sitting there and you're not on a keyboard, you're not staring at a screen, you're not checking your phone.

Yeah, I totally agree, which is actually one of the thing that has been very valuable to me is the the value of scheduling and being fairly meticulous about my calendar. This is going to sound totally lame. But, you know, I have family time blocked out on my calendar. I have walks with my wife blocked out of my calendar, which again, sounds completely lame and unnecessary. But what it does do is, is that pop up comes up on the right hand top rate screen of a side of my screen and suggests, hey, like it's family time or hey, it's a walk, you know.

But my wife Lindsay, who, you know, is also an entrepreneur, we're just we're very busy. We have two little kids and like so. Scheduling a walk together, 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 if we skip 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.

I could not agree more.

And only in the last six to nine months have have I been using with my girlfriend a shared calendar just for the two. Oh, 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 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 can bring this round one to a close. I'm curious what contemporary CEOs or CEOs, sort of C Suite execs do you most admire or admire greatly if that takes the pressure off a little bit? I'm just wondering what modern day current day folks do you look at and say, that's someone who I'd like to I could emulate a little bit or that's someone I could learn from or that's a good person to watch, etc.

?

Yeah, I mean, there are some obvious ones. I think one of the cool parts of being in my position 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 was that's brand new to me. Months. That's not a it'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. And so I've thought a lot about that. The truth is, a lot of the people that I admire, I sort of admire from I admire from afar, like Bob Iger and I've never met Bob Iger. I just 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 kind of the Shopify ecosystem. People we work with. Obviously, we're quite close to the folks at Stripe. You mentioned them earlier, Patrick and John. I mean, they are they're absolutely driven to do incredible things but also build an incredible company.

I think Pinterest is doing an amazing job as it was.

Well, in that way, a lot of the people that I really look up to, though, are not necessarily in tech persay. It's people that I just think, you know, one of the people that I really like, it's a mutual friend. I love talking to Chase Jarvis. I know you chase a good friend of yours as well. Every time I talk to Chase, I learned something completely new or Daymond John when I was also a mutual friend.

These I mean, Damon build Fubuki and 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 we got a shirt on L.L. Cool J for a music video and it just from these what seems like random stories and anecdotes, I'm able to find such great value in 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 not really. I'm trying to before I have I had Bailey, our four year old daughter. I want 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 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 a and type general theme right now, certainly in Silicon Valley, but I don't purport to be well-rounded, but I am trying to be well-rounded.

But 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 Pretending to be a studio controlled by 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 and how do you prepare and what kind of advice 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 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 am 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 they do email 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.

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 is before anyone even heard of Shopify. It's been a really important part of my life.

Seth is amazing. Seth Godin, there are people who are curious. 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 today.

There's a 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. I'm not planning on hiring more folks. But if people look up the name Charlie Hone In and my name, he's written about the experience that we had. You also wrote about the four hour body launch.

If that's cool, it should be the one thing that I've always found valuable in especially the early days of shop. If I was if I want to connect with someone who I knew was incredibly busy and there's 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 some random city, 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 three thousand 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. Hardly. Let me ask you, because we're talking about these various leaders, are there any biographies that you 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 a couple of years ago is a dog and I'm sure.

Have you read to Dog Sitting? 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.

It is awesome. It's awesome for anyone who wants to know who's building a company and when as an entrepreneur or frankly, anyone who's just interested in the idea of ambition. One of the reasons that I've 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, most lose ambition.

And the story of Shoe Dog and how Phil Knight was so determined. I just I think it was 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 proved anyone anymore, he was able to be incredibly candid. One of the problems I find particularly about autobiographies is that you end up seeing sort of the highlight reel of people's lives, especially people that are not sort of 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 loved about Dog is there's this incredible modesty and humbleness about the story, which is this was not pretty. And there were like twelve 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 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. That is that it's it was written, we could say cowritten, but in reality, written by one of my favorite authors whose name people will not recognize, and that is J.R. Moehringer. So he is the collaborator, so to speak, who wrote.

Phil Knight's memoir, Shuto, and for people who want to look him up, you can find him on Wikipedia, J.R., Moehringer, Moae H.R.H. and G.R., John Joseph, J.R. Moehringer and I came to know him because even as a non tennis player, I read Open, which is the autobiography of Andre Agassi. Yeah, Agassi. And it blew my mind. It was so good, so engrossing.

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 to write that down to you. So now, you know, it's it was in effect written by the same person at school and for that reason alone, patinated.

Let's go and leave that he did.

So J.R. Moehringer won the Pulitzer Prize for newspaper feature writing in 2000. Also, he's a hell of a writer. If I could if I could collaborate with 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 of hours of refinement and practice.

If that makes sense, that school shooting it's on the list will swap.

Since I've read open but have not read chuda, is there anything else that you would like to say, any closing comments, any thing 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, little past that. Twenty twenty.

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 for us in our story is having not really mentors, necessarily advisors, but people along for the ride that are our fans. Our supporters are catalysts for those days that are challenging. And I remember this particular moment. We were it was it was 2015 is 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, 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 a friend, maybe a 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 and some tech conference like like rails covid in your case. But these are the people in the story that are super valuable to have.

And I just I want to say just for a moment of gushing of emotion for a second, that it's just 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 find your group of supporters however you can. It changes everything. It allows you to it enables you to do things that you couldn't otherwise do, whether it's I'm going to give away ten thousand dollars for competition.

And that supporter says, no, that's stupid. Give away one hundred thousand dollars. 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 helped make magic. And you certainly have been that for us. And I'm just I'm very grateful for that. Thank you so much, Harley. It's wish you could see my my smile right now. 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 companion on the path.

That's a good thing. I like that term. That's a good companion on the path. That's a nice one. That's how I look at it.

And it's 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.

So at least with the sentiment with which I intend to. But those people, those companions, in many ways, they are the difference makers. They are the ones that it's not even those that 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 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 you show up at tech conferences and go to the greater room and try to find find out. 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. Say, hey, I'm thinking about this other thing, I mean, like I said earlier, as early as this morning, I paid you on something totally different 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 that advice. And it's just it's just this amazing thing that you can find. And it just you don't hear about these stories very much 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 frickin 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 kindness.

And, of course, you're going to be effective competitors. 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 or. It does. And actually, because we are playing the long game, we want Shopify to be one hundred year company and we ourselves want to be doing this for a very, very long time. And if you use a lens, a very long term perspective, whether it's a hundred 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 R a Y 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 this connotation or this 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 do 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 the the flywheel. That's that's where stuff gets really good.

Yeah, absolutely. And people can check out finite and infinite games by cars, as is also a good meditation on a lot of this stuff.

Harley, always so much fun. This was at the very 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 Harly s, Instagram at Harly website, half.com, obviously Shopify dot com. And we'll link to the build a business and past videos of the trip to Fiji and gasp Castle. All of this craziness.

I forget the gas while I was a fun one which people will get a kick out of.

That's really cool. Tembo. 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 this is really fun.

Absolutely. And I hope 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 one. Thanks to him and to everybody listening, we will have show notes, as always, links to everything that we have discussed at Timko blog for its podcast. Just Search Harly and it will pop right up and until next time.

Thank you for listening. Just a few important disclaimers. I own Stock and Shopify. I became an advisor to Shopify way back in the day when they had something like ten or twelve, 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 an investment advisor.

All opinions are mine alone. There are risks involved in placing an investment in any company, and 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.

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